Ethyl Levulinate
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Ethyl Levulinate
Ethyl levulinate is an organic compound with the formula CH3C(O)CH2CH2C(O)OC2H5. It is an ester derived from the keto acid levulinic acid. Ethyl levulinate can also be obtained by reaction between ethanol and furfuryl alcohol. These two synthesis options make ethyl levulinate a viable biofuel option, since both precursors can be obtained from biomass: levulinic acid from 6-carbon polymerized sugars such as cellulose, and furfural from 5-carbon polymerized sugars such as xylan Xylan (; ) ( CAS number: 9014-63-5) is a type of hemicellulose, a polysaccharide consisting mainly of xylose residues. It is found in plants, in the secondary cell walls of dicots and all cell walls of grasses. Xylan is the third most abundan ... and arabinan. References Carboxylate esters Ethyl esters {{ester-stub ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Keto Acid
In organic chemistry, keto acids or ketoacids (also called oxo acids or oxoacids) are organic compounds that contain a carboxylic acid group () and a ketone group ().Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. In several cases, the keto group is hydrated. The alpha-keto acids are especially important in biology as they are involved in the Krebs citric acid cycle and in glycolysis. Common types of keto acids include: *Alpha-keto acids, alpha-ketoacids, or 2-oxoacids have the keto group adjacent to the carboxylic acid. They often arise by oxidative deamination of amino acids, and reciprocally, they are precursors to the same. Alpha-keto acids possesses extensive chemistry as acylation agents. Furthermore, alpha-keto acids such as phenylpyruvic acid are endogenous sources for carbon monoxide (as a gasotransmitter) and pharmaceutical prodrug scaffold. Important representatives: ** ...
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Levulinic Acid
Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH3C(O)CH2CH2CO2H. It is classified as a keto acid. This white crystalline solid is soluble in water and polar organic solvents. It is derived from degradation of cellulose and is a potential precursor to biofuels, such as ethyl levulinate. Synthesis Levulinic acid was first prepared in 1840 by Dutch chemist Gerardus Johannes Mulder by heating fructose with hydrochloric acid. The first commercial production of levulinic acid began as a batchwise process in an autoclave by starch manufacturer A. E. Staley in the 1940s. In 1953 Quaker Oats developed a continuous process for the production of levulinic acid. In 1956 it was identified as a platform chemical with high potential. and in 2004 the US Department of Energy (U.S. DoE) identified levulinic acid as one of the 12 potential platform chemicals in the biorefinery concept. The synthesis of levulinic acid from hexoses (glucose, fructose) or starch in ...
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Ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a hydroxyl group). Ethanol is a Volatility (chemistry), volatile, Combustibility and flammability, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, the active ingredient in alcoholic drinks. Ethanol is naturally produced by the fermentation process of Carbohydrate, sugars by yeasts or via Petrochemistry, petrochemical processes such as ethylene hydration. It has medical applications as an antiseptic and disinfectant. It is used as a chemical solvent and in the Chemical synthesis, synthesis of organic compounds, and as a Alcohol fuel, fuel source. Ethanol also can be dehydrated to make ethylene, an important chemical feedstock. As of 2006, world produ ...
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Furfuryl Alcohol
Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents. Synthesis Furfuryl alcohol is manufactured industrially by hydrogenation of furfural, which is itself typically produced from waste bio-mass such as corncobs or sugar cane bagasse. As such furfuryl alcohol may be considered a green chemical. One-pot systems have been investigated to produce furfuryl alcohol directly from xylose using solid acid catalysts. Reactions It undergoes many reactions including Diels-Alder additions to electrophilic alkenes and alkynes. Hydroxymethylation gives 1,5-bis(hydroxymethyl)furan. Hydrolysis gives levulinic acid. Upon treatment with acids, heat and/or catalysts, furfuryl alcohol can be made to polymerize into a resin, poly(furfuryl alcohol). Hydrog ...
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Biofuel
Biofuel is a fuel that is produced over a short time span from biomass, rather than by the very slow natural processes involved in the formation of fossil fuels, such as oil. According to the United States Energy Information Administration (EIA), biofuels are mostly used for transportation, but can also be used for heating and electricity. Biofuel can be produced from plants or from agricultural, domestic or industrial biowaste. The greenhouse gas mitigation potential of biofuel varies considerably, from emission levels comparable to fossil fuels in some scenarios to negative emissions in others. See the biomass article for more on this particular subject. The two most common types of biofuel are bioethanol and biodiesel. The U.S. is the largest producer of bioethanol, while the EU is the largest producer of biodiesel. The energy content in the global production of bioethanol and biodiesel is 2.2 and 1.8 EJ per year, respectively. * Bioethanol is an alcohol made by fermen ...
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Biomass
Biomass is plant-based material used as a fuel for heat or electricity production. It can be in the form of wood, wood residues, energy crops, agricultural residues, and waste from industry, farms, and households. Some people use the terms biomass and biofuel interchangeably, while others consider biofuel to be a ''liquid'' or ''gaseous'' fuel used for transportation, as defined by government authorities in the US and EU. The European Union's Joint Research Centre defines solid biofuel as raw or processed organic matter of biological origin used for energy, such as firewood, wood chips, and wood pellets. In 2019, biomass was used to produce 57 EJ (exajoules) of energy, compared to 190 EJ from crude oil, 168 EJ from coal, 144 EJ from natural gas, 30 EJ from nuclear, 15 EJ from hydro and 13 EJ from wind, solar and geothermal combined. Approximately 86% of modern bioenergy is used for heating applications, with 9% used for transport and 5% for electricity. Most of the global b ...
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Cellulose
Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wall of green plants, many forms of algae and the oomycetes. Some species of bacteria secrete it to form biofilms. Cellulose is the most abundant organic polymer on Earth. The cellulose content of cotton fiber is 90%, that of wood is 40–50%, and that of dried hemp is approximately 57%. Cellulose is mainly used to produce paperboard and paper. Smaller quantities are converted into a wide variety of derivative products such as cellophane and rayon. Conversion of cellulose from energy crops into biofuels such as cellulosic ethanol is under development as a renewable fuel source. Cellulose for industrial use is mainly obtained from wood pulp and cotton. Some animals, particularly ruminants and termites, can digest cellulose with the help of ...
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Furfural
Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name ''furfural'' comes from the Latin word , meaning bran, referring to its usual source. Furfural is only derived from lignocellulosic biomass, i.e., its origin is non-food or non-coal/oil based. Aside from ethanol, acetic acid, and sugar, it is one of the oldest renewable chemicals. It is also found in many processed foods and beverages. History Furfural was first isolated in 1821 (published in 1832) by the German chemist Johann Wolfgang Döbereiner, who produced a small sample as a byproduct of formic acid synthesis. In 1840, the Scottish chemist John Stenhouse found that the same chemical could be produced by distilling a wide variety of ...
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Xylan
Xylan (; ) (CAS number: 9014-63-5) is a type of hemicellulose, a polysaccharide consisting mainly of xylose residues. It is found in plants, in the secondary cell walls of dicots and all cell walls of grasses. Xylan is the third most abundant biopolymer on Earth, after cellulose and chitin. Composition Xylans are polysaccharides made up of β-1,4-linked xylose (a pentose sugar) residues with side branches of α-arabinofuranose and/or α-glucuronic acids. On the basis of substituted groups xylan can be categorized into three classes i) glucuronoxylan (GX) ii) neutral arabinoxylan (AX) and iii) glucuronoarabinoxylan (GAX). In some cases contribute to cross-linking of cellulose microfibrils and lignin through ferulic acid residues. Occurrence Plant cell structure Xylans play an important role in the integrity of the plant cell wall and increase cell wall recalcitrance to enzymatic digestion; thus, they help plants to defend against herbivores and pathogens (biotic stress). ...
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Hemicellulose
A hemicellulose (also known as polyose) is one of a number of heteropolymer, heteropolymers (matrix polysaccharides), such as arabinoxylans, present along with cellulose in almost all embryophyte, terrestrial plant cell walls.Scheller HV, Ulvskov Hemicelluloses.// Annu Rev Plant Biol. 2010;61:263-89. doi: 10.1146/annurev-arplant-042809-112315. Cellulose is crystalline, strong, and resistant to hydrolysis. Hemicelluloses are branched, shorter in length than cellulose, and also show a propensity to crystallize. They can be hydrolyzed by dilute acid or Base (chemistry), base as well as a myriad of Cellulase, hemicellulase enzymes. Composition Diverse kinds of hemicelluloses are known. Important examples include xylan, glucuronoxylan, arabinoxylan, glucomannan, and xyloglucan. Hemicelluloses are polysaccharides often associated with cellulose, but with distinct compositions and structures. Whereas cellulose is derived exclusively from glucose, hemicelluloses are composed of diverse ...
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Carboxylate Esters
In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, (or ). It is an ion with negative charge. Carboxylate salts are salts that have the general formula , where M is a metal and ''n'' is 1, 2,...; ''carboxylate esters'' have the general formula (or ). R and R′ are organic groups; R′ ≠ H. Synthesis Carboxylate ions can be formed by deprotonation of carboxylic acids. Such acids typically have p''K''a of less than 5, meaning that they can be deprotonated by many bases, such as sodium hydroxide or sodium bicarbonate. :RCOOH + NaOH -> RCOONa + H2O Resonance stabilization of the carboxylate ion Carboxylic acids easily dissociate into a carboxylate anion and a positively charged hydrogen ion (proton), much more readily than alcohols do (into an alkoxide ion and a proton), because the carboxylate ion is stabilized by resonance. The negative charge that is left after deprotonation of the carboxyl group is delocalized between the ...
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