Natural gas composition. Source: Own elaboration from literature.
\r\n\tA number of advanced combustion technologies have been introduced to improve performance, fuel economy and emissions levels. Research in combustion technology has highlighted the importance of new fuels in reducing the petroleum dependence and achieving high efficiency with low pollutant formation.
\r\n\tThe purpose of this book is to collect interesting and original studies on combustion methods, advanced combustion strategies and new fuels able to achieve efficiency improvements and environment compliance.
\r\n\tContributions in which experimental, theoretical and computation approaches are applied to explore how fuel properties and composition affect advanced combustion systems and how advanced combustion technology can maximize engine efficiency and be environment-friendly are invited and appreciated.
In an energy transition scenario, setting the target date for the year 2050, for which the master lines are established to achieve a 100% renewable energy generation system (both stationary, thermal and mobility and transportation), all the revised studies indicate that energy sector will be based on the so-called renewable energy mix. In the meantime, biomethane and hydrogen (from renewable energy) could represent an effective strategy to move towards the targets set by the Renewable Energy Directive [1].
\nWith regard to energy sources for transport, a coexistence of fossil energies is foreseen (natural gas and liquefied petroleum gases (LPG) or autogas), to the detriment in favour of other fuels and energies from renewable sources, such as electricity (batteries) and gases of renewable origin (biomethane, hydrogen and synthesis gas).
\nThis chapter will focus on those energy sources based on gas in its different types and origins: natural gas, renewable natural gas or biomethane, hydrogen and synthesis gas. It has been decided not to include the autogas or LPG, because it is a fuel directly derived from petroleum, whose engine and distribution technology, unlike natural gas, is not compatible with gas fuels that could be renewable.
\nThe main support levers that renewable gases have, beyond the significant reductions in pollutant emissions, is the complementarity they have with renewable energy sources such as solar and biogas, as will be seen later in the sections dedicated to the generation and production technologies of each of these fuels, where renewable energy sources play a fundamental role. In some scenarios, renewable resources for mobility could be considered a ‘drop-in’ fuel, which means they are interchangeable with a particular petroleum derived fuel. In this sense, the inclusion of these resources contributes to the gradual replacement of the fossil fuels without considerable investment in infrastructure.
\nNatural gas is a mixture of different hydrocarbons, usually gaseous, that occurs naturally in the subsurface [2]. It usually appears next to oil, at the top of the same deposits, and the composition, like that of crude oil, varies depending on where it comes from.
\nThe origin of the natural gas comes from the decomposition of organic matter, which took place between 240 and 70 million years ago, during the time when large reptiles and dinosaurs inhabited the planet (Mesozoic Era). This organic matter came from planktonic organisms that accumulated on the seabed of coastal platforms or in shallow basins of ponds and were buried under successive layers of land by the action of natural phenomena.
\nMost oil fields usually contain liquid and gaseous hydrocarbons [3]. Normally, gases, being less dense than liquid, tend to occupy the upper part of the porous rock, held by the impermeable rock that acts as a seal. Below is oil and below it, large saltwater deposits.
\nThe discovery of natural gas dates back to ancient times in the Middle East. Thousands of years ago, it was found that there were natural gas leaks that set fire when they ignited, giving rise to the so-called ‘burning sources’. In Persia, Greece or India, temples were erected for religious practices around these ‘eternal flames’ [4].
\nNatural gas was not known in Europe until it was discovered in Britain in 1659, although it was not commercialized until 1790. In 1821, the inhabitants of Fredonia (United States) observed gas bubbles that traced to the surface in a stream. William Hart, considered the ‘father of natural gas’, excavated the first American natural gas well.
\nDuring the nineteenth century, natural gas was almost exclusively used as a source of light. Its consumption remained very localized due to the lack of transport infrastructure that hindered the transfer of large quantities of natural gas over long distances. In 1890, there was an important change with the invention of leakproof joints in gas pipelines.
\nIt was after the Second World War when the use of natural gas grew rapidly as a result of the development of gas pipeline networks and storage systems [5].
\nAlthough its composition varies depending on the reservoir, its main chemical species is 79–97% methane (in molar or volumetric composition), commonly exceeding 90–95%. It also contains other gases such as ethane (0.1–11.4%), propane (0.1–3.7%), butane (<0.7%), nitrogen (0.5–6.5%), carbon dioxide (<1.5%), impurities (water vapour, sulphur derivatives) and traces of heavier hydrocarbons, mercaptans, noble gases and other gases (Table 1) [6].
\nNatural gas composition. Source: Own elaboration from literature.
During the extraction, some gases that are part of its natural composition are treated and separated for different reasons among others: by their low calorific value (such as nitrogen or carbon dioxide), by their dew point in the gas pipelines (by having a low saturation temperature) or by their resistance of liquefaction of gases (such as carbon dioxide, which solidifies when producing liquefied natural gas or LNG).
\nPropane, butane and other heavier hydrocarbons are separated in order to have an efficient and safe gas combustion. In the same sense, water (steam) is eliminated in order to avoid clogging gas pipelines because at high pressures methane hydrates could be formed. So, sulphur derivatives are purified to very low concentrations to prevent corrosion, odour formation and sulphur dioxide emissions (causing acid rain) after combustion.
\nFinally, and for security reasons, traces of mercaptans (including methyl mercaptan, CH4S), which allow olfactory detection in case of leakage, are added for domestic use.
\nNatural gas reservoirs are usually found at high depths, either on land (‘onshore’) or under the sea (‘offshore’). Natural gas may be found in reservoirs in two states; ‘free’ or ‘associated’. In the ‘free’ state, the gas is extracted independently, not together with other compounds, and when it is ‘associated’, it is mixed with hydrocarbons or other gases from the reservoir.
\nA natural gas reserve becomes a ‘proven reserve’ when determining the quantity and quality of the natural gas contained in said deposit, its duration being calculated based on the amount of gas it has and an estimate of the expected consumption. Since carrying out this research and resource calculation process in its entirety implies significant investments, it is common that certain reserves are only geographically located and their potential is estimated, but they have not been subjected to such precise calculation studies until they are subjected to exploitation. However, gas-producing companies must have demonstrable reserves to guarantee the extraction and supply contracts they incur.
\nFigure 1 shows the distribution of proven natural gas reserves in the world by geographical area. The highest concentrations of gas are in the Middle East (41% of the world total), followed by the set of CIS countries (Commonwealth of Independent States) representing 31%. European reserves in a downtrend represent 2.7% of total reserves. In the industrial sector, the consumption of natural gas has increased at a faster rate than oil or coal in recent decades; it is estimated that natural gas and electricity will represent about two thirds of the energy used in the industry by 2040 [7].
\nProven world reserves of natural gas (source: CEDIGAZ y Oil and Gas Journal. Own elaboration).
Following recent research studies and obtaining new extraction technologies and despite the increase in global natural gas consumption, the amount of gas reserves has been increasing. However, new discoveries and the significance of new extraction technologies will have less and less weight, so it is essential to become aware of the efficient use of this resource as well as the research and development of alternative energy sources.
\nBiogas is a gas composed mainly of methane (CH4) and carbon dioxide (CO2), in varying proportions depending on the composition of the organic matter from which it was generated. The main sources of biogas are livestock and industrial agro waste, sludge from urban wastewater treatment plants (WWTPs) and the organic fraction of domestic waste. Biogas production through anaerobic digestion can utilise all kinds of organic material except lignin (Table 2) [8].
\nBiogas composition. Source: Ref. [9].
Purified biogas provides reductions in GHG emissions as well as several other environmental benefits when used as a vehicle fuel. Biogas emits less nitrogen oxide, hydrocarbon and carbon monoxide than gasoline or diesel, and engines fuelled by purified biogas are quieter than diesel engines [10].
\nBiogas is generated from the processes of biological decomposition in the absence of oxygen (anaerobes), which allow biogas to be produced from organic matter, which occur in landfills or in closed reactors commonly known as anaerobic digesters [10]. The degassing of landfills through the capture of the generated biogas allows to improve the safety conditions of exploitation of said landfills, also taking place in many cases an energy use of the biogas collected. In the case of anaerobic digesters, organic matter (substrates) is fed, and certain operating conditions (residence time, temperature, etc.) are maintained. In order to maximize the production of biogas in digesters, it is usual to mix different types of substrates (co-digestion), allowing for the sufficient nutrient concentration required by anaerobic microorganisms. Using the co-digestion strategy, special care must be devoted to chosen mixtures that allow biological processes without inhibitions.
\nAnaerobic reactors. Anaerobic reactors consist of containers (usually cylindrical in shape), in which the organic matter called substrate is introduced, which will be digested by the action of anaerobic bacteria. Anaerobic digestion facilities also incorporate a gas container, which can be incorporated into the biodigester itself or independently of it as a gasometer.
\nOther additional elements that are part of the biodigestion facilities are:
Premix containers: function is to homogenize and stabilize input mixtures, prior to entering the biodigester.
Sanitation systems: certain ‘inputs’, such as animal by-products (not intended for human consumption category), must be sanitized through pasteurization processes, prior to entering biodigesters.
Biogas cleaning and upgrading treatments: the cleaning process involves the passage of biogas through a series of filters, in which certain contaminant components are trapped (sulfur substances, siloxanes) that can damage the mechanical elements used in their subsequent valorization (engines, boilers). The biogas upgrading is the treatment of capture of the CO2 contained in the biogas, so that the concentration of CH4 is increased, transforming the raw biogas into biomethane, reusable as renewable natural gas.
Energy recovery of biogas: depending on the final use of the biogas produced, in those cases in which the biogas is not going to be treated for conversion into biomethane, the biogas can be used for energy recovery in cogeneration engines or turbines, to produce electrical and thermal energy, or directly in boiler for production of thermal energy.
Digestate treatment: the input inputs to the biodigester, after passing through the biodigesters, can be processed for later use as a fertilizer. For this, the digestate is subjected to a series of processes (solid-liquid separation, extraction of mineral components, etc.), through which different fertilizer products are obtained such as solid biofertilizer, nitrogen and phosphorus.
Figure 2 shows the different components of an anaerobic biodigestion plant.
\nAnaerobic biodigestion plant (source: BIOTIM®).
Stages of the anaerobic digestion process. During the anaerobic digestion processes, many types of bacteria are produced, which act during the different stages that make up the methanogenesis process, as described below (Figure 3).
\nStages of the anaerobic biodigestion process [11].
Disintegration. Initially large particles of biomaterials are disaggregated, and polymers are dissolved as action of the continuous mixture and moderate temperature.
\nHydrolysis. Hydrolysis consists in the process of breaking the longer chains of polymeric organic matter, through the action of enzymes secreted by hydrolytic bacteria. The complexity of this process will depend on the complexity of the organic matter entering the digester as well as the conditions in which the process occurs such as temperature, pH, retention time, the biochemical composition of the substrate, the size of particles, NH4+ concentration and the concentration of the hydrolysis products.
\nFermentation or acidogenic stage. During this stage the fermentation of the soluble organic molecules takes place in compounds that can be used directly by the methanogenic bacteria (acetic, formic, H2) and smaller organic compounds (propionic, butyric, valeric, lactic and ethanol mainly) that have to be oxidized by acetogenic bacteria in the next stage of the process.
\nAcetogenic stage. While some fermentation products can be directly metabolized by methanogenic organisms (H2 and acetic), others (ethanol, volatile fatty acids and some aromatic compounds) must be transformed into simpler products, such as acetate (CH3 COO−) and hydrogen (H2), through acetogenic bacteria.
\nAt this stage of the process, most anaerobic bacteria have extracted all the food from the biomass and, as a result of their metabolism, eliminate their own waste products from their cells. These products, simple volatile acids, are the ones that will use as a substrate the methanogenic bacteria in the next stage.
\nMethanogenic stage. At this stage, a broad group of strict anaerobic bacteria acts on the products resulting from the previous stages. Methanogenic microorganisms can be considered as the most important within the consortium of anaerobic microorganisms, since they are responsible for the formation of methane and the elimination of the medium from the products of the previous groups, being, in addition, those that give name to the general biomethanization process.
\nCharacterization of raw materials. To ensure a good yield in the production of biogas, it is necessary to make a correct selection of the raw materials that are going to be introduced into the biodigester.
\nFor this, it is necessary to carry out previous tests (at laboratory scale), during which the suitability of each of the materials in terms of their methane production potential will be determined.
\nBiochemical oxygen demand. Biochemical oxygen demand (BOD) provides a measure of biodegradable organics present in a sludge and, in turn, can be used as a metric for the overall effectiveness of an anaerobic digester.
\nBOD is defined as the amount of oxygen, divided by the volume of the system, taken up through the respiratory activity of microorganisms growing on the organic compounds present in the sample (e.g. water or sludge) when incubated at a specified temperature (usually 20°C) for a fixed period (usually 5 days, BOD5) [12]. This parameter may be used to quantify the concentration of biodegradable organics present in sludge.
\nThe measurement of this parameter provides information on the amount of biodegradable organic matter by the bacteria contained in the biodigester and therefore on the amount of methane that can be produced.
\nChemical oxygen demand (COD). Chemical oxygen demand (COD) indicates the amount of oxygen needed to degrade a certain amount of organic matter. In COD tests, a sludge is refluxed in excess with a solution of potassium dichromate and sulphuric acid. As COD measures all organics in a sludge, its value is understandably higher than that of BOD. Thus, the ratio of BOD to COD can be used to represent the biodegradable fraction of a sludge.
\nAmount of dry matter and volatile solids. Dry matter or total solids are a parameter which indicates the concentration of organic matter that contributed in the feeding of the biodigester. On the other hand, volatile solids inform about the amount of organic matter that ours contains. Depending on the dry matter contained in the digester’s input material, the type of digestion to be carried out will be determined, and therefore the type of digester that will be necessary to use for the process. Thus, in those cases where the dry matter concentration is less than 20% of the total, we will be talking about wet digestion and dry digestion when the amount of dry matter is greater than 20% of the total.
\nCarbon and nitrogen ratio. This is a determining parameter when evaluating the viability and potential performance of an anaerobic digestion process, so it must be considered during the selection process of the raw materials that will be used as inputs of the process. Thus C/N concentrations of 20/1 or 30/1 will give optimal results in digestion [13, 14]. However, low proportions of this ratio may be indicative of high concentrations of ammonium that are detrimental to the process, given the inhibitory nature of the nitrogen compounds process.
\nProcess conditions. In addition to the type and characteristics of the raw material, the state of the same and its composition, the environmental conditions of the process inside the biodigester will largely determine the correct development of the process and the biogas production yield.
\nTemperature and pH, which are key parameters. Temperature (T) of the process will depend on the type of bacteria used in the process. Depending on the bacteria and the temperature conditions, we can distinguish between different types of processes:
Mesophilic processes, which take place in a temperature range between 25 and 45°C, typically 35°C.
Thermophilic processes are those that take place in temperature conditions above 45°C, typically 55°C.
Psychrophilic processes are the least developed so far, in which the work of bacterias at temperatures around 20°C. Normally the psychrophilic conditions are referred for systems without any heat supply.
As for pH, in ideal conditions it must be in terms of neutrality, avoiding acidic and basic conditions. Excessive acidity (much less than 7) or a medium that is too caustic (much greater than 7) can reduce the metabolism of bacteria or even kill them.
\nHydraulic retention time. The hydraulic retention time (HRT). It is the time that passes a flow in the digester from entering until leaving it. It can be referred to the liquid flow rate, the MS it contains or the time that the biomass (bacteria) resides inside the reactor before leaving with the sludge. HRT is an important operational parameter for the anaerobic reactors which can affect the conversion of volatile solids (VS) into biogas. HRT is one of the main parameters to consider when designing the size of the digester [15], and in turn this will depend on the type and conditions of the raw materials used as inputs in the process.
\nUpgrading from biogas to biomethane or renewable natural gas. It is known as biogas upgrading, the treatment process through which the biogas obtained through anaerobic digestion is transformed into a renewable gas with a quality grade like fossil natural gas [16].
\nFor the biogas to be transformed into renewable natural gas thus increasing its specific caloric value, it is necessary that a series of components such as CO2, H2O, sulphur compounds (H2S), siloxanes, NH4, O2 and N2 be removed from the initial gas stream [17]. For this there are currently different technologies, among which the following stand out. These technologies can be classified in two principal groups:
Sorption technologies: adsorption and absorption
Separation: membranes and cryogenic
Pressure swing adsorption (PSA). In this case, carbon dioxide is separated from the biogas by adsorption on a surface under elevated pressure. Molecular sieve materials such as zeolites and activated carbon are commonly used as adsorptive materials for biogas upgrading. The adsorbing material is regenerated by a sequential decrease in pressure before the column is reloaded again, hence the name of the technique.
\nSome of its advantages are the compactness of the equipment, low energy requirements, low capital investment and simplicity [18]. On the other hand, if hydrogen sulphide is present in the raw gas, it will be irreversibly adsorbed on the adsorbing material. In addition, water present in the raw gas can destroy the structure of the material. Therefore, hydrogen sulphide and water need to be removed before the PSA column.
\nPhysical scrubbing (absorption). In an upgrading plant using the absorption technique, the raw biogas meets a counter flow of liquid in a column which is filled with plastic packing (in order to increase the contact area between the gas and the liquid phase). The principal behind the absorption technique is that carbon dioxide is more soluble than methane. The liquid leaving the column will thus contain increased concentration of carbon dioxide, while the gas leaving the column will have an increased concentration of methane.
\nTypically, either water or organic solvent (e.g. methanol, N-methyl pyrrolidone and polyethylene glycol ethers) are used to absorb CO2 in physical absorption plants, whereas amine scrubbing is widely used for chemical absorption. Nowadays, water scrubbing accounts for ~41% of the biogas upgrading market [19].
\nWater scrubbing. The driving force of the process is the difference of solubility for CH4 and CO2 in water. CO2 is more soluble in water than CH4 [20]. With the increase in process pressure, this difference becomes higher, and the CO2 is absorbed more quickly and to a larger quantity. In the scrubber column carbon dioxide is dissolved in the water, while the methane concentration in the gas phase increases. The gas leaving the scrubber has therefore an increased concentration of methane. The water leaving the absorption column is transferred to a flash tank where the dissolved gas, which contains some methane but mainly carbon dioxide, is released and transferred back to the raw gas inlet.
\nMembrane separation. It is based on the selective permeability property of membranes [21]. Dry membranes for biogas upgrading are made of materials that are permeable to carbon dioxide, water and ammonia. Hydrogen sulphide and oxygen permeate through the membrane to some extent, while nitrogen and methane only pass to a very low extent. Usually membranes are in the form of hollow fibres bundled together. The process is often performed in two stages. Before the gas enters the hollow fibres, it passes through a filter that retains water and oil droplets and aerosols, which would otherwise negatively affect the membrane performance. Additionally, hydrogen sulphide is usually removed by cleaning with activated carbon before the membrane [22].
\nOn the market, three types of membranes are typically used: polymeric, inorganic and mixed matrix membranes. Inorganic membranes have several advantages compared to polymeric, mainly due to their higher mechanical strength, chemical resistance and thermal stability. The current trend in industrial applications is to use mixed matrix membranes [17].
\nCryogenic separation. This technique involves subjecting the biogas to high pressures and low temperatures, so that the CO2 goes into its liquid state, while the methane remains in the gaseous state. Prior to subjecting the raw biogas to the cryogenization process, it must be pretreated to remove the sulphur compounds (H2S) contained “in the gas”, since H2S could damage heat exchangers [23]. On the other hand, volatile organic compounds (VOC) and siloxanes are efficiently removed during the cooling and condensation process, which is a natural part of the cryogenic improvement process.
\nHydrogen is currently one of the energy vectors that have the greatest potential for medium-term application, within the range of new alternative fuels to conventional petroleum products. The most important characteristic of hydrogen as an energy vector is that the energy yield of hydrogen is about 122 kJ/g, which is 2.75 times greater than hydrocarbon fuels [24].
\nHydrogen is a clean fuel without toxic emissions and can easily be applied in fuel cells for electricity generation [25]. It may be stored as a gas under pressure or in a liquid state, or distributed through natural gas networks, thus representing an alternative with a high potential for long-term replacement of natural gas and as a gas compatible with natural gas in the short and medium terms [26].
\nAlthough hydrocarbons and coal are currently the main feedstock used for H2 production [27], the need to increase the integration of renewable technologies will become unavoidable. Thus, this section will focus on the development of hydrogen production technologies compatible with renewable sources.
\nThe hydrogen production will depend on two main variables: the feedstock (water or organic materials such as natural gas, biomass, coal or oil) and the origin of the energy to be used in the production process (conventional or renewable energy). If a water disponibility is possible, the main cost of hydrogen production by electrolysis is an electricity cost.
\nThermolysis. It involves the application of heat (high temperatures) that causes the water molecule to rupture, resulting in hydrogen and oxygen. The direct decomposition of the water molecule, by thermal processes, requires temperatures around 2.500°K [28]. To reach these temperatures, it is necessary to use solar concentration technologies. However, the application of solar concentrators, to produce hydrogen by direct water thermolysis, leads to material problems and an increase in losses due to re-radiation, reducing absorption efficiency. An effective technique of separation of hydrogen and oxygen is necessary, to avoid an explosive mixture. These handicaps are the reason why there is currently no pilot plant in which the direct decomposition of water takes place, which makes it unfeasible today [29].
\nAs an alternative technique to direct thermolysis, solar thermochemical technology is proposed, based on the reduction of metal oxides [30]. These processes occur in two phases. The first phase consists in the reduction by means of the application of solar energy of the metallic oxide. The second phase, in which the application of heat is not necessary, consists in the exothermic hydrolysis of water, accompanied by the oxidation of the metal, to form hydrogen and the corresponding metal oxide [31].
\nElectrolysis. Electrolysis involves the breakdown of the water molecule through the application of electrical energy, resulting in hydrogen and oxygen. Traditionally, water electrolysis has been carried out in electrolytic cells formed by two electrodes immersed in an aqueous solution (electrolyte) [32]. Through the application of direct current, the dissociation of the water molecule occurred. The chemical reaction produced during the water electrolysis process is shown below:
\nAs already mentioned, the electrolysis process occurs in systems called electrolysers. Next, the main existing electrolyzer technologies are descriptively presented.
\nPolymeric membrane electrolyzers (PEM). In a polymer electrolyte membrane (PEM) electrolyzer, the electrolyte is a special solid plastic material. Water reacts at the anode to form oxygen and positively charged hydrogen ions (protons). Electrons flow through an external circuit, and hydrogen ions selectively move through the EMP to the cathode. In the cathode, hydrogen ions combine with the electrons in the external circuit to form gaseous hydrogen [33] (Figure 4).
\nScheme of a polymeric membrane electrolyzer (PEM). Source: Green Power Co. Ltd.
Polymeric membrane electrifiers (PEM) are formed by a polymeric membrane, generally manufactured by a commercial polymer perfluorosulfonated acid (brand name of Nafion®) and by two carbon electrodes attached to both sides of the membrane (MEA) [33].
\nDue to its acidic nature, expensive noble metal catalysts such as platinum at the hydrogen and iridium-oxide at the oxygen evolving electrode must be used. Catalyst substances are applied on the electrodes, which favours the processes of electron transfer and therefore increasing the yield of hydrogen production reactions [34].
\nThe MEAs are installed between the so-called bipolar plates. These bipolar plates are responsible for the conduction of water inside the electrolyzer as well as the transport of the gases generated to the exit. In addition, they are responsible for providing mechanical stability to the system, ensuring electrical conductivity and evacuating the heat generated [33].
\nAlkaline electrolyzers. Alkaline electrolyzers are based on classical technology in which two electrodes are submerged in a solution or electrolyte. In the case of alkaline electrolyzers, the electrolyte consists of a solution of potassium hydroxide (KOH), in concentrations of 30–35%. In these electrolyzers, normally both the electrodes and the tank are made of nickel or a steel alloy with chrome and nickel, materials that can withstand the corrosive power of alkali solutions [35].
\nIn these electrolyzers each of the cells is separated by a diaphragm that prevents the mixing of hydrogen and oxygen produced. These diaphragms are made of ceramic oxides coated with a metallic material. In addition to the membrane, the electrolyzers are formed by a current and voltage adjustment system, a supply water deionization unit and a gas separation device [36] (Figure 5).
\nScheme of an alkaline electrolyzer. Source: Smolinka-Fraunhofer Institute für Solare Enegiesysteme ISE.
Alkaline electrolyzers are more economical and durable, are recognized for their mature technology, are safe and can work with pressures up to 25 bars. It is the most mature technology, and due to its development, it is the most economical. Its effectiveness is around 62–82%, being it higher when more larger is the size of the electrolyzer [37].
\nChemical conversion processes: reforming and gasification. Another of the technologies for the generation of hydrogen are those based on the processing of organic materials through two technologies called reforming and gasification.
\nReforming. The reforming processes are the most common today for obtaining hydrogen. The reforming technology consists of the combination of a combination of hydrocarbons (natural gas, LPG, liquid hydrocarbons) and alcohols with water vapour, resulting in the generation of hydrogens from various chemical reactions [38].
\nWater steam reforming. Water reforming is based on the reaction of a fuel with water vapour on a catalyst [39]. The water vapour reforming process (known by the acronym SMR, steam methane reforming) may be applied to a wide variety of hydrocarbons (natural gas, LPG, liquid hydrocarbons, etc.) and alcohols. Of all of them, the most used for its availability and ease of handling is natural gas.
\nThis reaction that is verified in the first phase is that of reforming itself, taking place at temperatures around 900°C in tubes through which methane and water vapour circulate through nickel-based catalyst beds. At the end of the process, the gas is directed towards a CO displacement unit in which the following reaction on copper catalysts is verified.
\nThe gas produced as a result of the two previous reactions passes through a condenser in which the water vapour is removed and finally reaches the third stage of the process, the purification process. The gas that reaches this unit is rich in hydrogen with carbon dioxide, water debris, carbon monoxide and methane. This gaseous stream is purified in a membrane separator or adsorption-desorption system (PSA: pressure swing adsorption.) From which, hydrogen is obtained with a purity of 99.999% [38].
\nGasification. This technology produces synthesis gas (CO + H2) by controlled heating of an organic waste at temperatures between 800 and 1000°C in an O2 atmosphere or H2O vapour. The synthesis gas obtained can be used as a direct fuel, as a source of H2 or as a chemical raw material to prepare gasoline or diesel by means of the Fischer-Tropsch process. The use of water vapour in the feed allows to increase the production of hydrogen by reducing the production of tars and CO. Gasification, given the severity of the treatment, is particularly indicated for the treatment of plant residues that are difficult to use in other ways.
\nAmong all the reactions involved, the steam reforming and the water-gas reaction should be noted for their importance in determining the degree of gasification and composition of the gaseous products obtained.
\nFermentative hydrogen. Biological hydrogen production is possible under anaerobic conditions [40]. Some enzymes, called hydrogenases, are able to create H2 molecules from H+, which is released as consequence of the anaerobic degradation of simple organic molecules, as sugars, into small fatty acids (mainly acetic acid). Digesters, with the same configuration as that of the ones used for biomethane production, can produce H2 from different organic wastes. Shorter hydraulic retention times must be applied in order to avoid H2 consumption by other groups of organism.
\nPhotosynthetic hydrogen. Some species of microalgae contain hydrogenases that transform H+ to H2 under the absence of oxygen and solar illumination [41]. This process is a consequence of continuous electron motion in the light-related reactions. These electrons are used to reduce H+ resulting in the creation of H2 molecules.
\nOne of the main challenges that currently arise, to make viable the introduction of alternative fuels for vehicular use, is the logistics and supply of these fuels, from origin to the different points of supply.
\nCurrently the only gas (not derived from petroleum), marketed for vehicular use, is natural gas. The supply of vehicular natural gas (NGV) is supplied through service stations or gas stations, to which natural gas arrives through road transport (in cryogenic or pressure tanks) and through the connection to networks of gas transportation.
\nThe introduction of other alternative gases such as renewable natural gas (biomethane) and hydrogen is posing important challenges for gas companies, since the characteristics of these gases, although compatible with pre-existing natural gas networks, present a series of differences that will make the adaptation of the current infrastructure necessary and the need to create new distribution and distributed generation models.
\nBiomethane. Biogas generated in anaerobic digestion plants from agro-food waste, sewage treatment plants, landfills, etc. once purified and transformed into biomethane, with a quality equivalent to natural gas, might be injected into natural gas grids. For this, it will be necessary that the continuous measurement equipment is available at the injection point, which certifies the quality of the gas. There is a European regulation, UNE-EN 16726 Gas infrastructure, to standardize gas quality and the main parameters and their limits for the gases to be transported and/or injected into the natural gas network.
\nThe control by the managers of the natural gas distribution networks and of the distribution of this new gas and the necessary quality and safety problems, to ensure that the distributed gas maintains the necessary conditions, implies an important technological update, which will require the implementation of new management and control tools, from the injection points to the supply.
\nTo keep track of this valuable characteristic after having been mixed with fossil natural gas, a tracking mechanism is needed. Mass or energy balances serve reliable and complete retracing of biomethane from its production site to the final consumer.
\nBiomethane trade predominantly takes place in the country of its production. There are only a few examples of physical cross-border biomethane trade, e.g. from Germany to Sweden and to the Netherlands as well as from the UK to the Netherlands. If the market is not balanced, meaning demand exceeds supply or vice versa, cross-border trade is able to increase flexibility and transfer biomethane where it is needed. Barriers are often created by the different national regulatory frameworks, but they can be removed by harmonizing the national tracking systems which means that two different biogas registers are able to exchange biomethane amounts from the country of production to the country of final consumption.
\nHydrogen. Being considered an energy vector this is a compatible gas with natural gas networks. However, this compatibility does not mean that H2 can be transported as such in the same network; since it is a different molecule, it will be necessary to look for ways to be combined with natural gas or biomethane, obtaining a final gas with greater energy potential.
\nThus, two main formulas are planned: injection of H2 into the network (P2G), both in different % of H2 injected into natural gas (power to gas—H2), and the methane of H2 for injection as synthetic natural gas.
\nThe production of hydrogen, from the surplus of electricity, is an optimal way to absorb the excess (renewable) energy produced at times of demand, as an alternative form of storage [42]. Thus the energy ‘stored’ in the generated hydrogen (acting as an energy vector) can be combined with natural gas or biomethane transported in the gas network.
\nAlternatively, the H2 produced can be recovered through CO2 methane (discarded in the biogas to biomethane upgrade process), resulting in methane of renewable origin.
\nIn economic terms, if connected to the grid, hydrogen can be produced subject to short-timescale variations in the power market or under flat rates through power purchase agreement (PPA) contracts. In the first case, production will happen especially at moments of low- and medium-power prices. There will be a certain number of operating hours at higher prices, causing hydrogen costs to increase. Electrolyzers may be operated as demand response assets to support energy balance over the grid [43], making profits from balancing or ancillary services (IRENA, 2018c). In the second case, hydrogen is produced at flat power rates under PPA contracts. In this case, operation can be continuous, which can improve the overall efficiency of the process—the higher the number of operating hours, the lower the hydrogen production costs. However, such baseload operation reduces the flexibility of the power system.
\nOther options to transport renewable fuels. For those cases where the transport of large volumes of gas, whether biomethane or hydrogen, is not required, they can be transported as compressed or liquefied gases in the cryogenic state. The choice of another method will depend on the amount of gas as well as the destination of the gas. Transport in the gaseous state does not allow the accumulation of large volumes of gas, unlike liquefaction (high pressure and low temperature) that will allow the storage of larger volumes.
\nBoth liquefaction and gas compression will lead to important energy requirements, which will influence the final cost of gas distribution. The decision on the form of gas transportation will be linked to the other factors that affect the gas logistics chain, including the form of production (centralized or distributed), supply chain as well as access to the point of use.
\nAs for transport methods, renewable gases, like other gases, can be distributed by ship, train and tank trucks. However, contrary to what happens with other gases of non-renewable origin such as natural gas, one of the main advantages of renewable gases is that these can be generated at points close to those of use, avoiding the need to carry out transportation on large routes, which involves the intensive use of energy.
\nAs an alternative to the injection of biomethane and hydrogen in the natural gas distribution network, an alternative form of supply to end users is proposed, avoiding the use of the gas network. In those cases, in which the green gas generation location (biomethane or hydrogen) is far from the gas network, an isolated model or diffuse model is proposed.
\nRegarding biomethane as an alternative to the large biogas production facilities, linked to centralized biogas agro-livestock plants, or sewage treatment plants or urban waste plants, a model that has gained strength in recent years is the implantation of small-/medium-size biogas production plants with by-products of agricultural origin. These installations are mostly located in places far from large population centres and therefore without the possibility of connection to the gas network. To solve this handicap, these biogas production plants (and biomethane), if they can be close to communication roads (roads), with a large transit of livestock vehicles (tractors and other machinery) and trucks. Therefore, the production of biomethane in these plants, and the installation of dispensing stations for this renewable gas (gas stations), could be an important alternative to the transport of renewable gas through the gas network.
\nAn alternative solution for isolated hydrogen generation and distributed supply would be through the development and implementation of so-called hydrogenators, or hydrogen production stations from renewable energy (photovoltaic and/or wind), which is stored in batteries being used on demand for the production of hydrogen through the use of electrolyzers. In this way, this new fuel could be given access, in areas or road networks far from the main population centres.
\nIn recent years there has been a great controversy between detractors and defenders in relation to the environmental benefits of natural gas in general and renewable natural gas, against the use of conventional fossil fuels (diesel and gasoline) for vehicular use.
\nAmong the detractors, various environmental groups and associations are used as main arguments against the benefits attributed to the use of gas as an alternative fuel, in that combustion of this in engines generates similar concentrations and even higher pollutant gases than fossil fuels. On the contrary, the studies that defend the environmental advantages of the use of gas as fuel defend the low emissions (mainly of particles) of the gas against other fossil fuels.
\nIn this chapter, different alternative fuels to conventional fuels have been highlighted. In this sense, although it is true that CO2 emissions from both natural gas and renewable natural gas will be very similar to those produced by conventional fuels, since both types of fuels have an organic (carbon) origin, it is important to highlight the other environmental advantages that alternative gas fuels have compared to conventional ones.
\nAs already mentioned, the intention of presenting natural gas as a fuel has not been so much for its direct environmental benefits (which as it has already been described in a certain way if it has them) but for the importance that this can mean as a bridge to greater use of renewable natural gas.
\nSome of the environmental (and socio-economic) advantages that the deployment of renewable natural gas can present in a future scenario in which other energy sources such as electricity coexist could be the following.
\nHowever, as already said, the combustion of renewable natural gas (and biogas), if it would generate CO2 emissions, given the renewable origin of the gas, these emissions would count as neutral in a global balance, given that the origin of the biogas is from organic materials, which in their origin have already absorbed atmospheric CO2.
\nIn addition to this advantage (neutrality), the management of organic waste for the production of biogas, if carried out in a controlled manner, avoids the bad or nonmanagement of organic waste (household waste, animal waste, other organic waste) that would entail the emission of CH4 (uncontrolled natural digestion), with the important effect that this gas supposes in terms of atmospheric heating.
\nAlthough it is true that the use of biogas and biomethane as alternative fuels will not have a great impact on the global balance of CO2 emissions if it will be a significant reduction in other emissions such as sulphur compounds and the suspended particles.
\nSpecifically, it has been shown that in heavy vehicles, natural gas reduces NOx emissions up to 86% and particles 75%. In the case of buses, natural gas reduces NOx emissions up to 90% and particle emissions up to 69% compared to diesel. Additionally, natural gas does not have sulphur in its composition, so unlike diesel, it eliminates SOx emissions (Foundation for the Promotion of Industrial Innovation of the Higher Technical School of Industrial Engineers of the Polytechnic University of Madrid).
\nIn addition to the direct environmental advantages, it is necessary to highlight other advantages implicit in the use of biogas and biomethane, such as those linked to the new circular economy scenario and the much needed revitalization of rural areas.
\nThe management of organic waste for the production of biogas for automotive and transportation allows to contribute to the so-called circular economy, whose purpose is the use of all waste generated, so that these are transformed into resources and thus close the productive circle, avoiding the demand for new resources and wasting on raw materials useful for other uses.
\nAs for the different formats of production and management of renewable natural gas, as mentioned in the previous sections, a possible scenario for the development of an economy based on the use of waste and by-products for the generation of biogas could be based in a distributed generation model, in which the biogas generation points are directly linked to the production centres of the by-products. In this way, a broad framework of development possibilities could be opened at the local level, which would allow establishing a development path for those rural areas most in need of alternatives.
\nIt is presented in a very different scenario from that of biogas, since both its origin and its use as an alternative fuel are presented in a scenario with large differences compared to other alternative gases.
\nHydrogen, as explained in the previous sections, originates from different processes that involve the use of external energy to cause the dissociation of the water molecule, releasing the hydrogen atoms. To carry out this process, depending on the origin of the energy source, it may be considered an environmentally sustainable process or not. In the case of hydrogen production, from renewable electricity (photovoltaic, wind or hydroelectric solar), the hydrogen thus produced if it can be considered a renewable fuel with zero emissions.
\nHydrogen, in its use as a fuel in transport, is generally used to feed fuel cells, which generate electricity that is supplied to an electric motor, obtaining as its only residual gas water vapour, which is a completely free energy source of emissions. Also, hydrogen, in combination with residual CO2 (e.g. from biogas upgrading processes), through a process known as power to gas, would lead to the production of methane that can be used, for example, in vehicles powered by renewable natural gas.
\nAdditionally, neither atmospheric emissions nor CO2 emissions are a problem for the use of hydrogen. In addition, the great advantage of using this technology, since as the only exhaust gas, water vapor is obtained, from the use of hydrogen as an energy source. With this, the cycle would be closed because hydrogen produced with water is returned to the environment.
\nButadiene-1,3 (BD) is diolefin containing two conjugated double bonds. In oxidation, BD exhibits properties inherent to all olefins, but higher reactivity was compared to but-1-ene and but-2-ene. Both BD and C4-olefins can be a feedstock for producing valuable chemicals by gas-phase oxidation [1, 2]. The oxidation on oxide catalysts in gas phase results in the formation of maleic anhydride together with crotonaldehyde and 2,5-dihydrofuran. Centy and Trifiro suggested a simple consecutive pathway for BD oxidation over V-P-oxide catalysts [3, 4], whereas Honicke et al. proposed multiple pathways from BD to crotonaldehyde, 2,5-dihydrofuran, 2-butene-1,4-dial, 2(5H)-furanone and furan, and finally to maleic anhydride over V2O5 catalysts [5]. Schroeder specified the oxidation pathway on V-Mo-oxide catalysts, including 3,4-epoxy-1-butene as a primary oxidation product [6]. Epoxidation of BD occurs over Ag catalysts [7, 8, 9, 10] used in industry for the production of ethylene oxide and intensively investigated in the oxidation of other olefins (e.g., [11, 12]). 3,4-Epoxy-1-butene is further converted into 2,3-dihydrofuran followed by hydrolysis to form 4-hydroxybutyraldehyde. The secondary transformations occur directly under epoxidation conditions on Ag catalysts promoted with B-P [13], Mo [14], and Mo-P-Sb [15] or by subsequent treatments of 3,4-epoxy-1-butene.
In the early 1980s, oxidation of n-butane has become the preferred method for manufacturing maleic anhydride [16, 17]. The invented synthesis of maleic anhydride from butane creates a competition for the gas-phase oxidation of BD since hydrogenation of maleic anhydride opens a possibility of producing various oxygenates, which produced from BD earlier. At the same time, the gas-phase oxidation of BD still suffers from formation of polymer resins, which leads to excessive consumption of raw materials and catalyst deactivation. This problem and large power consumption inherent to all gas-phase reactions are absent in the liquid-phase oxidation since the low temperature and application of appropriate solvents prevent the formation of the resins. The liquid-phase low-temperature oxidative reactions, in particular the oxidation of olefins, were intensively studied at the end of the last century [18, 19, 20, 21, 22, 23]. A renewed interest in this area is growing now [24, 25, 26, 27] and can be expected to be strengthened in the nearest future as a response to modern requirements of green chemistry to minimize power and materials consumption. In addition, the liquid-phase reactions are well applicable for the oxidation of various olefins and BD because of high reactivity of these hydrocarbons that allows the oxidation at low temperature. At the same time, BD becomes more affordable owing to permanent improvements in its manufacturing.
The title of this chapter concerns the application of green oxygen (air and hydrogen peroxide) in liquid-phase conditions. The liquid-phase oxidative reactions are an important part in chemistry of all olefins and, in particular, of the simplest representative of conjugated diolefins as they open many routes for the conversion of the hydrocarbons. We represent here an analysis of literature information concerning the oxidation of BD in liquids and references to the related reactions of olefins. In detail, we described the catalytic systems in the study of which we acquired our own experience.
Olefins readily interact with radical species. The most susceptible to radical attack is allyl position to produce allyl oxygenates [28, 29]. In the absence of an allylic carbon atom, one of the double bonds of BD is involved in the oxidation. Neat or dissolved in a nonpolar solvent, BD interacts with oxygen at moderate temperature according to radical chain mechanism to form oligomeric butadiene polyperoxide, C4H6O2 [30]. The reaction is accelerated by increasing the temperature or adding free radical initiators and inhibited by adding acids. From the NMR analysis, molecular structure of the polyperoxide formed at 50°C in the presence of 37 Torr of oxygen was composed of equal amounts of 1,4- and 1,2-butadiene units separated by peroxide units [31]. The structure of the polyperoxide (the ratio of 1,4- to 1,2-butadiene units) does not depend on the reaction temperature, whereas the content of bound oxygen in the polyperoxide varies with oxygen pressure. The ratio of peroxide to hydrocarbon units is below 1 at a low oxygen partial pressure. Thermal decomposition as well as hydrogenation of polyperoxide leads to the formation of 3-butene-1,2-diol and 2-butene-1,4-diol or corresponding saturated diols, preferably 1,4-derivatives (Scheme 1) [30, 32, 33, 34, 35].
Formation and reductive decomposition of the polyperoxide [30].
Decomposition of the polyperoxide forms not only 3-butene-1,2-diol and 2-butene-1,4-diol but also side products such as formaldehyde, acrolein (from 1,2-units), and resinous insoluble material (presumably resulting from the reaction of the 1,4-units with aldehydes) [31]. Therefore, the preferred formation of 1,4-oxygenates from the thermal decomposition of polyperoxide is not a strong support of predominance of 1,4-units in the polyperoxide structure.
The rate of decomposition of the polyperoxide increases with increasing temperature, addition of bases (amines) [36], or metal ions as radical initiators. Butadienyl polyperoxide is readily decomposed in the presence of metal ions of variable oxidation state. Therefore, the transition metal compounds participate as catalysts in the radical chain oxidation of BD with oxygen. The oxidation products are similar to those obtained under the decomposition of the polyperoxide. 3-Butene-1,2-diol and 2-butene-1,4-diol can be obtained with the selectivity sufficiently high for the chain radical process, especially if one considers the low stability of these products with respect to secondary oxidation. Thus, a mixture of 3-butene-1,2-diol and 2-butene-1,4-diol has been prepared by oxidative dihydroxylation of BD with oxygen in acetic acid solution of Pd(OAc)2. From a practical point of view, the most valuable 2-butene-1,4-diol has been formed with selectivity of 25% [37].
We tested Pd and Au catalysts in the radical chain oxidation of BD in polar media. Both soluble palladium acetate and insoluble supported metals caused the formation of the products, the most part of which appeared from decomposition of the intermediate butadienyl polyperoxide [32] (Scheme 2). The main products are 3-butene-1,2-diol and 2-butene-1,4-diol. 4-Hydroxybut-2-enal can be formed in the decomposition of polyperoxide and in oxidation of 2-butene-1,4-diol. Oxidative dehydration of 2-butene-1,4-diol produces furan. Both butanediols can be esterified to form corresponding diacetates, but only 2-butene-1,4-diol diacetate has been found in the reaction solution. Acrolein occurs from breaking C─C bond under decomposition of polyperoxide or, possibly, from secondary conversion of 3-butene-1,2-diol. C8 oxygenates originate from polyperoxide fragments containing less than 1:1 ratio of butadiene to oxygen units. In addition, there are impurities of C6 cyclic oxygenates occurring from cyclodimerization of BD (Diels-Alder reaction) followed by oxidation of 4-vinylcyclohexene. The amount of the products is given in Table 1.
GC-detected products of the radical chain oxidation of BD.
Catalyst (mg) | BD (mmol) | Solvent | T (°C) | Time (h) | Products (mmol) | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|
1 + 2 | 3 | 4 | 5 | 6 | Others1 | Peroxide2 | |||||
Pd(OAc)2 2.5 | 70 | HOAc/H2O 88/12 | 70 | 2 | 2.5 | 0.6 | 0.1 | <0.1 | 1.3 | 0.2 | 8.5 |
Pd(OAc)2 2.5 | 70 | HOAc/dioxane/H2O 19/75/6 | 80 | 2 | 4.6 | 3.1 | <0.1 | 0.4 | 7.8 | 0.1 | 9.4 |
0.5%Au/SiO2 120 | 70 | HOAc/dioxane/H2O 44/50/6 | 80 | 4 | 4.7 | 3.2 | <0.1 | 0.1 | 8.9 | 2.0 | 9.1 |
0.5%Au/SiO2 120 | 70 | HOAc/dioxane/H2O 44/50/6 | 80 | 6 | 8.5 | 5.3 | 0.4 | 1.3 | 10.7 | 7.1 | 7.0 |
5%Pd/C 3000 | 100 | DMA/H2O 94/6 | 90 | 3 | 10.3 | 0.4 | 0 | 4.8 | 2.2 | 0.73 | 0.8 |
5%Pd0.5%Te/C 3000 | 100 | DMA/H2O 94/6 | 90 | 3 | 0.5 | 0.1 | 0 | 0.1 | 0.1 | 0.84 | 0.2 |
GC detected products from oxidation of BD (70 mmol) by oxygen (O2/N2 = 10/90, 60 atm) in a solvent (100mL).
C8 diols and acetates, and C6 cyclic oxygenates.
Iodometric titration.
0.1mmol сrotonaldehyde and methyl vinyl ketone.
0.4 mmol сrotonaldehyde and methyl vinyl ketone.
In addition to the stable compounds, a large amount of peroxide compounds have been iodometrically detected in acetic acid and acetic acid/dioxane solutions (Table 1). Peroxide oxygen refers to butadienyl polyperoxide since the addition of Ph3P reducer to the solution results in disappearance of the peroxide and formation of 2-butene-1,4-diol together with minor amounts of furan and 3-butene-1,2-diol. The polyperoxide exhibited sufficient stability in several oxidation tests but almost completely decomposed with a large amount of Pd/C catalysts. As a result, enhanced formation of 2-butene-1,4-diol and 4-hydroxybut-2-enal is achieved in this case (fifth row inTable 1).
The addition of Te to Pd/C catalyst lowers the production of all oxidation products. Bottom row in Table 1 shows the inhibitory effect of Te on the chain radical oxidation reaction. At the same time, more noticeable becomes formation of the oxidation products non typical for the chain radical mechanism. These are crotonaldehyde and methyl vinyl ketone, which show the possibility of a nonradical heterolytic mechanism of oxidation on the PdTe/C catalyst.
Palladium catalysts are widely used in the liquid-phase heterolytic oxidation of olefins [38]. The most significant mechanisms for practice are acetoxylation of ethylene to vinyl acetate and Wacker oxidation of olefins converting ethylene to acetaldehyde and but-1-ene to methyl ethyl ketone. A mechanism of olefin oxygenation under the action of Pd(II) complexes established by Moiseev et al. and Henry et al. [39, 40] is now described in numerous publications (e.g., chapter by Reinhard Jira in book [24]). The mechanism includes the formation of Pd(II) complex with olefin and inner sphere transformations resulting in the reduction of Pd2+ to form carbonyl compound and Pd0 black. Assisted by Cu(II) chloride or other intermediate oxidant, reoxidation of Pd0 with oxygen closes the catalytic cycle, allowing the use of oxygen as a stoichiometric oxidant.
Analogous to light olefins, BD reacts under homogeneous conditions in an aqueous solution of PdCl2 catalyst and CuCl2 oxidant. The oxygenation is directed to one of the double bonds with the retention of the second double bond to produce crotonaldehyde [41, 42]. The oxidation conditions are identical to those applied for oxidation of ethylene to acetaldehyde and 1-butene to methyl ethyl ketone (Wacker-type oxidation), but the kinetics is different [43], in particular the order of reaction with respect to Cl− and H+ ions. Unlike the oxidation of ethylene and other olefins, the oxidation of BD is zero-order with respect to the hydrocarbon. The kinetic parameters of BD oxidation are determined by high reactivity of the conjugated π-bonds, in particular by a strong BD to Pd2+ bonding in the intermediate complex. Unlike propylene, the oxygenation of the BD double bond is directed at the terminal rather than inner carbon atom to form crotonaldehyde. This is probably due to the stabilizing effect of the second double bond. In the presence of Pd2+ ions and another strong oxidizing agents of P-Mo-V heteropolyacids, BD is converted to furan in the similar conditions [44]. It seems like crotonaldehyde was initially formed and then converted under oxidizing conditions to furan, as in a similar homogeneous system [45]. Oxygen is a final stoichiometric oxidant, but the strong intermediate oxidant (Cu2+ or heteropolyacid) is necessary for easy regeneration of the ionic palladium in the oxidation of BD and olefins, as well.
We have observed catalysis by PdCl2 when the radical chain oxidation of BD to diols, furan, and acrolein proceeds along with nonradical oxidation to form mainly crotonaldehyde together with small amounts of methyl vinyl ketone and furan (Scheme 3) (first row in Table 2). It is interesting that the system does not contain an oxidizing agent, except oxygen. There is no need of any intermediate oxidant since reoxidation of Pd0 to Pd2+ is provided by peroxide intermediates generated in a radical process. Telluric acid inhibits the radical process but does not operate as an oxidant for Pd0 to maintain the nonradical oxidation by Pd2+. As a result, the PdCl2 with H6TeO6 solution is inactive in oxidation of BD (second row in Table 2). By contrast, the heterogeneous 5%Pd2%Te/C catalyst is able to provide nonradical oxidation, with the radical chain oxidation being inhibited by Te. As a result of inhibiting action of Te, the large amount of the catalyst and low concentration of BD appear unfavorable for the development of the chain process. The oxidation on the 5%Pd2%Te/C catalyst in aqueous dimethylacetamide (DMA) has been observed to give crotonaldehyde and methyl vinyl ketone as main products (third row in Table 2). Interestingly, crotonaldehyde is a predominant product of heterolytic oxidation with PdCl2, but nearly equal amounts of crotonaldehyde and methyl vinyl ketone are produced on the 5%Pd2%Te/C catalyst in the same conditions.
Nonradical reaction of BD on PdTe/C catalyst in polar solvents.
Catalyst(mg) | BD (mmol) | Time (h) | Products (mmol) | ||||||
---|---|---|---|---|---|---|---|---|---|
Furan | Acrolein | Methyl vinyl ketone | Croton-aldehyde | 3-Butene-1,2-diol | 2-Butene-1,4-diol, 4-hydroxybut-2-enal | Others | |||
PdCl2 120 | 43 | 3 | 0.4 | 1.1 | 0.3 | 1.6 | 3.2 | 3.9 | 0.2 |
PdCl2 120, H6TeO6 800 | 43 | 3 | 0.2 | 0.5 | <0.1 | 0.4 | <0.1 | 0.5 | 0.1 |
5% Pd 2% Te/C 2000 | 22 | 6 | 0.1 | <0.1 | 0.8 | 0.6 | — | 0.2 | 0.3 |
GC detected products from oxidation of BD by oxygen (O2/N2 = 10/90, 60 atm) in DMA (30 mL, 3% H2O), T 90°C.
Besides DMA, other polar solvents can be used in this oxidation. The presence of proton additive is required in the solvent (Table 3). No reaction has been observed in anhydrous acetonitrile.
Solvent (g) | Catalyst (g) | Н2О (%) | H2SO4 (mmol/L) | Time (h) | Products (mmol) | ||
---|---|---|---|---|---|---|---|
Furan | Methyl vinyl ketone | Croton aldehyde1 | |||||
DMA | 1 | 17 | — | 4 | 0.2 | 1.4 | 1.2 |
Dioxane | 0.5 | — | 5 | 6 | 0.5 | 1.0 | 0.7 |
Acetonitrile | 1 | 17 | — | 5 | <0.1 | 1.0 | 0.8 |
Acetonitrile | 1 | 17 | 8 | 5 | 0.3 | 1.7 | 0.9 |
Acetonitrile | 0.5 | — | 2 | 4 | 0.8 | 2.0 | 1.2 |
Acetonitrile | 0.5 | — | — | 3 | 0 | 0 | 0 |
GC detected products from oxidation of BD (4.5 mmol) by oxygen (O2/N2 = 10/90, 40 atm) on 5% Pd 2%Te/C catalyst in a solvent (35 mL), T 100°C.
Crotonaldehyde can be partly subjected to further oxidation to crotonic acid.
According to XPS analysis, the 5%Pd2%Te/C catalyst contains both reduced Pd0 and ionic Pd2+, and two oxidation states of tellurium Te0 and Te4+ [46]. The Pd2+ to Pd0 ratio on the catalyst surface becomes larger with an increase in tellurium content that indicates an oxidizing influence of TeO2. It can be expected that the oxidation state of the surface is enhanced under the reaction conditions. Nevertheless, dissolution of Pd and Te during reaction does not exceed 1% of the content of both components in the solid catalyst, the solution exhibiting no catalytic activity. Therefore, activity of the catalyst refers to the active components on the surface of carrier and is associated with their reversible redox transformations. Based on the known mechanisms of homogeneous oxidation of olefin, one can propose two possibilities for oxidation of BD by oxygen on the PdTe species, both assuming a nonradical heterolytic interaction. Perhaps the mechanism is in general similar to that postulated for the oxidation of BD and olefins in the presence of Pd2+ complexes, oxygen, and intermediate oxidant (Scheme 4, Route 1). It involves surface Pd2+ ions and TeO2 oxidant providing regeneration of Pd2+.
Tentative routes for nonradical oxidation of BD on PdTe/C catalyst.
However, there is a difference in products composition. Crotonaldehyde and furan are produced in above-mentioned oxidations of BD with homogeneous Pd2+ catalysts [41, 42], whereas methyl vinyl ketone is the second product formed in our oxidation on the PdTe catalyst. To explain this difference, one can consider an oxidation of BD by hydrogen peroxide as an alternative or parallel reaction (Route 2 in Scheme 4). Hydrogen peroxide is generated from oxygen on Pd0 species. The high reactivity of olefins with respect to peroxide compounds is known [47]. It is known that hydrogen peroxide does not accumulate during reaction. But it is found in trace amounts in the reaction solution and can form a reactive peroxide compound of Te4+ on the surface of the catalyst. In both mechanisms proposed, Te serves as a carrier of molecular or peroxide oxygen, and the surface of Pd2+/Pd0 activates reagents due to the adsorption of O2 and BD. Thus, the PdTe/C catalyst opens the possibility of oxidation of BD by a nonradical heterolytic mechanism due to the combined effect of the two active components.
Wacker-type oxidation of olefins and analogous Pd-catalyzed nonradical oxidation of BD produce usually carbonyl compounds, but special additives are required for obtaining dioxygenates. Nevertheless, the oxidative 1,2-addition to olefins is known to occur under the action of Pd2+ complex and oxoanion strong oxidants, such as periodate [48] or nitrate anions, in acetic acid solution to form glycol derivatives [49, 50, 51]. Mechanism of the oxidation is based on a nonradical inner sphere interaction of olefin with oxidant in Pd2+ complex. Similar interaction is probably realized in oxidation of BD in the presence of palladium as the catalyst of nonradical heterolytic olefin oxidation and Sb, Bi, Te, or Se promoters. Heterogeneous catalysts containing these active components have shown unique catalytic properties in oxidation of BD selectively to 2-butene-1,4-diol diacetate (Scheme 5) [52, 53].
Oxidative 1,4-addition to BD.
XPS analysis of the Pd and PdTe catalysts indicates that Te-oxide is able to increase positive charge on Pd surface [46], thus being an oxidation promoter for palladium. The ionic state of surface palladium is responsible for heterolytic oxidation. Acetic acid is used as a solvent for this reaction. The mechanism of formation of 2-butene-1,4-diol diacetate is proposed by Takehira et al. for PdTe catalyst (Scheme 6) [54], and fundamentally identical one is proposed for the RhTe catalyst [55]. The details in intermediate structures explain the preferential formation of trans-2-butene-1,4-diol in the case of Pd-containing catalyst and cis-isomer in the case of Rh.
Mechanism of 1,4-oxidative addition to BD [54].
Exceptionally high selectivity of BD to 2-butene-1,4-diol diacetate conversion is explained by a concert interaction of BD with surface Pd and with acetate anions. Adsorbed on Pd, BD forms π-allyl-type intermediate that undergoes acetoxylation on the terminal carbon atom. Resulting monoacetoxyl reacts with the second acetate to give 2-butene-1,4-diol diacetates and 3-butene-1,2-diol diacetate in amounts proportional to the reactivity of carbon atoms 1 and 2 (Scheme 6). In fact, only 2-butene-1,4-diol diacetates are produced. Analogous mechanisms are realized in homogeneous oxidation of various dienes in the presence of Pd complexes and p-benzoquinone oxidizing agent, instead of Te. Oxidation of diene alcohols [56] and substituted conjugated diolefins [57] proceed effectively, but BD reacts with low yield and selectivity.
As noted earlier, Te-oxide is able to inhibit radical chain oxidation of BD, the selectivity of which is lower than the selectivity of the heterolytic process. Besides, Te operates as an inhibitor of radical polymerization of BD and oxidation products, thus preventing the formation of side high-boiling products. Acetic acid (possibly, other carboxylic acids) also contributes to the achievement of high selectivity in BD oxidation. Being not only solvent but also reagent (OAc− anions), it is involved in an intermediate interaction with olefin to form the surface Pd intermediate, and finally stabilizes the product as ester, preventing its secondary transformations. Based on the unique properties of the PdTe/C-HOAc catalytic systems, the industrial process for the production of 2-butene-1,4-diol diacetate has been developed by Mitsubishi Chemical. BD is oxidized to 2-butene-1,4-diol diacetate with selectivity of 98%. Possible further improvements of the process can be connected with the application of other platinum metals (Pt, Rh, and Ir) combined with various promotors.
If acetic acid is replaced by alcohol, 1,4-dialkoxylation of conjugated dienes was developed in Pd(OAc)2 solution. p-Benzoquinone was used as the oxidant and methanesulfonic acid as a promoter [58]. The oxidation is suggested to follow mechanism including the formation of the (π-allyl)palladium(benzoquinone) intermediate (Scheme 7).
1,4-Dialkoxylation of conjugated dienes [38].
In other case, dialkoxybutenes are prepared by reacting BD in the presence of carbon-supported Group VIII noble metals with Te or Se additives. Similar to diacetates, the formation of ethers in alcohol solvent increased the stability of dioxygenated products against secondary oxidation. However, the formation of 3,4-dimethoxy-1-butene and 1,4-dimethoxy-2-butene in comparable amounts is in contrast with Scheme 6 and indicates a radical mechanism of BD oxidation, when 2-butene-1,4-diol and 3-butene-1,2-diol are formed as primary products and then converted to ethers in the alcohol medium [59].
We have prepared PdTe/C catalysts by hydrolytic deposition of palladium under the reductive conditions, followed by treatment with H6TeO6. The procedure is similar to one often described for the synthesis of PdTe catalysts. No evidences for the occurrence of binary Pd–Te phases have been provided by XRD, and XPS analysis evidences Pd0, PdO, Te0, and TeO2 [60]. The absence of the Pd-Te phase and the partially oxidized state of the active metals have also been reported by Takehira [54] for Pd-Te-C catalysts. As assumed, Te is located in the outer layer of supported particles. The characteristics of the PdTe/C catalysts were detailed by HAADF-STEM analysis of the surface and line EDX analysis of composition of the supported particles [60]. The results represent an unusual distribution of components on the surface, where Te does not form an individual crystalline phase but is located on the surface of Pd particles in a highly dispersed state. These data explain properties of the PdTe catalysts. In particular, the ability of Te to inhibit the radical reactions is in part due to the coverage of the palladium surface, which normally tends to initiate radical chains.
The primary products in BD oxidation on PdTe/C catalyst in methanol and further conversion of them under the oxidation conditions are shown in Scheme 8, and the amounts are given in Table 4.
Products of BD oxidation on PdTe/C catalyst in methyl alcohol.
Catalyst, conditions | Products (mmol) | |||||||
---|---|---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | |
5%Pd0.5%Te/C, 10 mmol BD, 100°C, 3 h | 0.54 | 1.16 | 0.35 | 1.58 | 0.17 | 1.48 | 0 | 0.73 |
5%Pd0.5%Te/C, H2SO4, 10 mmol BD, 100°C, 3 h | 0.45 | 2.02 | 0.08 | 0.12 | 1.42 | 2.30 | 0 | 1.81 |
5%Pd2.7Te/C, H2SO4, 10 mmol BD, 120°C, 2 h | 0.24 | 0.06 | 0 | 0.06 | 0.66 | 2.80 | 2.0 | 0 |
5%Pd2.7Te/C, H2SO4, 40 mmol BD, 120°C, 2 h | 0.23 | 0.06 | 0 | 0.07 | 0.78 | 6.70 | 3.90 | 0 |
Products of BD oxidation in solvent CH3OH (10% H2O) (30 mL), H2SO4 (0.1 mmol where indicated).
As well as in DMA, nonradical heterolytic oxidation of BD in alcohol medium leads to the formation of crotonaldehyde (1) and methyl vinyl ketone (4). Besides, 1,4-dimethoxy-2-butene (6) is produced analogously to 2-butene-1,4-diol diacetate in acetic acid. The primary products undergo further transformations depending on the reaction conditions. Sulfuric acid promotes oxidation, especially toward 1,4-oxidative addition (comparison of first and second rows in Table 4). An increase in Te content lowers the reaction rate but increases proportion of products formed through 1,4-addition (third row in Table 4). Composition of oxidation products obtained in the presence of the Pd0.5Te/C catalyst and H2SO4 is differed from the one in the radical chain oxidation (compare data given in Tables 1 and 4). 3,4-Dimethoxy-1-butene and acrolein that indicate nonradical oxidation do not appear. Peroxide compounds were also not detected in the solution after the reaction. The chain process does not develop due to the presence of Te and low concentration of BD used to eliminate the formation of the radical chains. Moreover, the radical products do not appear even at increased concentration of BD (fourth row in Table 4). Similarly to acetic acid, methyl alcohol in a mixture with sulfuric acid converts the oxidation products to methyl esters. However, oxidation in the alcohol medium is slower than in acetic acid, and further improvement of the selectivity of the formation of 1,4-addition products is required.
Two competitive methods for direct epoxidation of olefins are gas-phase oxidation with oxygen over silver catalyst and liquid-phase reactions with organic hydroperoxides or hydrogen peroxide in the presence of soluble or supported W, Mo, Ti complexes. The gas-phase epoxidation is typical for obtaining light epoxides, whereas epoxidation with peroxide compounds in liquid is applicable for a wide range of substrates containing double bonds. Both type reactions are based on interaction of olefin with electrophilic oxygen species. Under liquid-phase epoxidation, catalytically active metal complexes react with peroxides to attach the reactive oxygen as ligand which attack the double bond of olefin. Hydrogen peroxide is effective oxygen donor and has an advantage of low-temperature reaction giving environmentally benign water as a by-product [61, 62].
The liquid-phase epoxidation of BD with H2O2 is known to occur over titanium silicates in CH3OH [63] and in CH3CN solution of heteropoly compounds [64, 65]. The data for these reactions are given in Table 5.
Catalyst1 | H2O21 (mmol) | BD (bar) | Time (h) | Epoxide (mmol) | Sel.BD (%) | H2O2 efficiency (%) | Reference |
---|---|---|---|---|---|---|---|
TS-1(6 mg)2 | 0.5 | 1.5 | 1 | 0.25 | n.d. | 52 | [63] |
TBA4[γ-SiW10O34(H2O)2] (3 μmol)3 | 0.3 | 2.5 | 9 | 0.30 | 99 | 99 | [64] |
TBA-PW11(10 μmol)4 | 0.9 | 1 | 5.5 | 0.51 | 88 | 88 | [65] |
EMIm-PW11(10 μmol)4 | 0.9 | 1 | 5 | 0.65 | 91 | 90 | [65] |
EMIm-PW11(2.3 μmol)5 | 1.0 | 1 | 5 | 0.20 | 97 | 100 | [65] |
Epoxidation of BD with H2O2 in solvents.
Catalyst, H2O2 and epoxide produced were normalized to 2 mL of the reaction mixture.
CH3OH solvent, room temperature.
CH3CN solvent, room temperature.
CH3CN solvent, 60 °C.
CH3CN solvent, 50 °C.
Both catalysts are activators of hydrogen peroxide, capable of forming peroxide complexes. Thoroughly investigated for various olefins, the mechanism of epoxidation is realized for the conversion of BD to 3,4-epoxy-1-butene. Coordinated on metal ion, the electrophilic oxygen interacts with one of the equivalent double bonds of BD leaving intact the second C═C bond. Oxygen transfer from peroxide ligand to double bond of olefin has been proved using isotopic reagents [64]. The addition of oxygen to the second bond of BD is more difficult; therefore, the formation of a diepoxide is not detected in reactions with hydrogen peroxide.
Lacunary polyoxotungstates are effective catalysts for epoxidation of olefins with H2O2 [66]. Besides olefins, [HPW11O39]6−and [γ-SiW10O34(H2O)2]4− anions catalyze epoxidation of BD with diluted aqueous H2O2 in acetonitrile solution. Epoxidation of BD has been shown to proceed with high selectivity for 3,4-epoxy-1-butene. Appearance of small admixtures of furan, 3-butene-1,2-diol, and 2-butene-1,4-oxygenates is associated with isomerization and hydrolysis of 3,4-epoxy-1-butene. The unproductive radical decomposition of H2O2 is minimal or absent when the reaction is carried out at a low temperature and at a low concentration of hydrogen peroxide. This is favorable for maintaining high selectivity for 3,4-epoxy-1-butene, because the secondary oxidation of 3,4-epoxy-1-butene by radical intermediates is prevented. As a result, only negligible amount of acrolein appears in the product. Moreover, small additives of EMImBr have been found to inhibit radical decomposition of H2O2, thus increasing the selectivity of BD to 3,4-epoxy-1-butene conversion and efficiency of H2O2 consumption. As a result, the efficiency of H2O2 consumption for producing 3,4-epoxy-1-butene is extremely high, it approaches to 100% under favorable conditions. Both Si- and P-centered heteropolytungstates exhibit equally effective catalysis.
Under reaction conditions, the catalytically active anions are generated from starting lacunary polyoxotungstate anion. It has been shown by NMR that [HPW11O39]6− anion is a precursor of tungsten-depleted anions [PW4] and [PW2], which operate as the most effective activators of hydrogen peroxide and are responsible for epoxidation (Scheme 9) [65]. This is confirmed by the high reactivity of a specially synthesized anion {PO4[WO(O2)2]4}3− in epoxidation of olefins [67].
Transformations of heteropolytungstates in oxidation of BD to 3,4-epoxy-1-butene (EpB) [65].
Despite the limited use of 3,4-epoxy-1-butene itself, it is nevertheless a raw material for the synthesis of various C4-oxygenates such as 1,4-butanediol [68], 3-butene-1,2-diol and 2-butene-1,4-diol [69, 70, 71], and 2,5-dihydrofuran [72]. Therefore, low-temperature and selective epoxidation of BD can be considered as a principal stage of alternative synthesis of demanded and valuable chemicals.
Close nature of BD and light olefins is manifested in similar reaction properties, so that liquid-phase oxidation reactions of BD and olefins have similar mechanisms in many features. The oxidation of olefins and BD in liquid medium enables realization of several routes and obtaining a wide range of products, which are more diverse if compared with gas-phase oxidation. We have considered here the radical chain oxidative conversion of BD realized through the stable polyperoxide intermediate, the formation of which is, to a certain extent, inherent to many olefins. Palladium is able to catalyze homolytic (radical) and heterolytic (Wacker-type) oxidation of olefins. Very close to olefins, the properties of BD are manifested in reactions assisted by homogeneous and more often heterogeneous Pd-containing catalysts. (Note that the tendency to heterogenization of soluble catalysts is observed in liquid-phase reactions.) We observe an interesting phenomenon when the mechanism and products of the Pd-catalyzed oxidation are controlled by promoters. In dependence on other components, the catalytic action of Pd is switched from radical oxidation to nonradical oxygenation directed to one carbon atom or 1,4-position of BD when Pd is promoted with Te or related metals. The effect of Te as an oxidation promoter of palladium and a radical inhibitor allows PdTe catalysts to show substantial efficiency in the well-known industrial synthesis of 1,4-diacetoxybutene in acetic acid and also in other oxidations of BD such as formation of crotonaldehyde and methyl ethyl ketone in aqueous media. The reaction medium and concentration of reagents are also important factors to vary the mechanism of oxidation. Low concentration of BD in the reaction mixture reduces the development of the chain process and makes it possible to realize the oxidation by the heterolytic mechanism. Polar organics are conventional solvents for various oxidations, but acetic acid and methanol exhibit special properties creating conditions for preferable formation of esters of 1,4-butanediol. The identity in mechanisms is also observed in epoxidation of olefins and BD with hydrogen peroxide, where the same catalytically active Ti silicates and polyoxometalates are successfully used to attain highly selective conversion of hydrocarbon and H2O2. All this shows that liquid-phase oxidation have a great potential in converting the BD into valuable oxygenates. To develop this area, extremely productive can be appeal to analogy in chemistry of BD and olefins. A large body of information relating to the oxidation of olefins can be productively applied to understand the mechanisms in oxidation of BD and to develop a strategy for synthesis of purposed oxidation products.
This work was conducted within the framework of budget project No 0303-2016-0006 for Boreskov Institute of Catalysis.
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