Names | |
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Preferred IUPAC name 2,6-Dimethoxyphenol | |
Other names Syringol 2-Hydroxy-1,3-dimethoxybenzene Pyrogallol 1,3-dimethyl ether | |
Identifiers | |
3D model (JSmol) | |
1526871 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.856 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C8H10O3 | |
Molar mass | 154.16 g/mol |
Appearance | Gray to light brown solid |
Density | 1.15857 g/cm3 (60 °C) [2] |
Melting point | 50 to 57 °C (122 to 135 °F; 323 to 330 K) |
Boiling point | 262 °C (504 °F; 535 K) [2] |
Slightly soluble | |
Vapor pressure | 15.8 Pa (60 °C) [2] |
Hazards [1] | |
Flash point | 140 °C (284 °F; 413 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Syringol is the organic compound with the formula HO(CH3O)2C6H3. The molecule is a phenol, with methoxy groups in the flanking (2 and 6) positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, although typical samples are brown owing to air-oxidized impurities. Together with guaiacol, syringol and its derivatives are produced by the pyrolysis of lignin. Specifically, syringol is derived from the thermal decomposition of the sinapyl alcohol component. As such, syringol is an important component of wood smoke.
Lignin, comprising a major fraction of biomass, is sometimes classified according to the syringyl component. Pyrolysis of lignin derived from sinapyl alcohol affords syringol. The conversion involves replacement of the propenyl alcohol substituent of the sinapyl alcohol by hydrogen. A high syringyl (or S) content is indicative of lignin from angiosperms. In contrast, pyrolysis of lignin from gymnosperms gives more guaiacol, resulting from conversion of coniferyl alcohol. These lignins have a high guaiacyl (or G) content. [3]
In preparation of food by smoking, syringol is the main chemical responsible for the smoky aroma, while guaiacol contributes mainly to taste. Artificial liquid or solid smoke flavorings also contain these chemicals, on average composing 13.73% and 13.42% of those products by mass respectively. [4]
Pyrolysis oil, a biofuel derived from woody biomass, can be optimized to yield syringol as a byproduct, potentially competing with petroleum-derived phenols. [5] Some studies indicate that syringol can substitute for phenol formaldehyde resin, a commonly used, water resistant adhesive for plywood. [6]
Cellulose is an organic compound with the formula (C
6H
10O
5)
n, 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%.
Lignin is a class of complex organic polymers that form key structural materials in the support tissues of most plants. Lignins are particularly important in the formation of cell walls, especially in wood and bark, because they lend rigidity and do not rot easily. Chemically, lignins are polymers made by cross-linking phenolic precursors.
Thermal depolymerization (TDP) is the process of converting a polymer into a monomer or a mixture of monomers, by predominantly thermal means. It may be catalysed or un-catalysed and is distinct from other forms of depolymerisation which may rely on the use of chemicals or biological action. This process is associated with an increase in entropy.
The pyrolysis process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. Temperature can be understood as thermal vibration. At high temperatures, excessive vibration causes long chain molecules to break into smaller molecules. The word is coined from the Greek-derived elements pyro "fire", "heat", "fever" and lysis "separating".
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 furfur, 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. In addition to ethanol, acetic acid, and sugar, furfural is one of the oldest organic chemicals available readily purified from natural precursors.
A biorefinery is a refinery that converts biomass to energy and other beneficial byproducts. The International Energy Agency Bioenergy Task 42 defined biorefining as "the sustainable processing of biomass into a spectrum of bio-based products and bioenergy ". As refineries, biorefineries can provide multiple chemicals by fractioning an initial raw material (biomass) into multiple intermediates that can be further converted into value-added products. Each refining phase is also referred to as a "cascading phase". The use of biomass as feedstock can provide a benefit by reducing the impacts on the environment, as lower pollutants emissions and reduction in the emissions of hazard products. In addition, biorefineries are intended to achieve the following goals:
Guaiacol is an organic compound with the formula C6H4(OH)(OCH3). It is a phenolic compound containing a methoxy functional group. Guaiacol appears as a viscous colorless oil, although aged or impure samples are often yellowish. It occurs widely in nature and is a common product of the pyrolysis of wood.
The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.
4-Ethylguaiacol, often abbreviated to 4-EG, is a phenolic compound with the molecular formula C9H12O2. It can be produced in wine and beer by Brettanomyces. It is also frequently present in bio-oil produced by pyrolysis of lignocellulosic biomass.
Pyrolysis oil, sometimes also known as bio-crude or bio-oil, is a synthetic fuel under investigation as substitute for petroleum. It is obtained by heating dried biomass without oxygen in a reactor at a temperature of about 500 °C (900 °F) with subsequent cooling. Pyrolysis oil is a kind of tar and normally contains levels of oxygen too high to be considered a pure hydrocarbon. This high oxygen content results in non-volatility, corrosiveness, immiscibility with fossil fuels, thermal instability, and a tendency to polymerize when exposed to air. As such, it is distinctly different from petroleum products. Removing oxygen from bio-oil or nitrogen from algal bio-oil is known as upgrading.
Lignocellulose refers to plant dry matter (biomass), so called lignocellulosic biomass. It is the most abundantly available raw material on the Earth for the production of biofuels. It is composed of two kinds of carbohydrate polymers, cellulose and hemicellulose, and an aromatic-rich polymer called lignin. Any biomass rich in cellulose, hemicelluloses, and lignin are commonly referred to as lignocellulosic biomass. Each component has a distinct chemical behavior. Being a composite of three very different components makes the processing of lignocellulose challenging. The evolved resistance to degradation or even separation is referred to as recalcitrance. Overcoming this recalcitrance to produce useful, high value products requires a combination of heat, chemicals, enzymes, and microorganisms. These carbohydrate-containing polymers contain different sugar monomers and they are covalently bound to lignin.
Renewable Fuels are fuels produced from renewable resources. Examples include: biofuels, Hydrogen fuel, and fully synthetic fuel produced from ambient carbon dioxide and water. This is in contrast to non-renewable fuels such as natural gas, LPG (propane), petroleum and other fossil fuels and nuclear energy. Renewable fuels can include fuels that are synthesized from renewable energy sources, such as wind and solar. Renewable fuels have gained in popularity due to their sustainability, low contributions to the carbon cycle, and in some cases lower amounts of greenhouse gases. The geo-political ramifications of these fuels are also of interest, particularly to industrialized economies which desire independence from Middle Eastern oil.
Second-generation biofuels, also known as advanced biofuels, are fuels that can be manufactured from various types of non-food biomass. Biomass in this context means plant materials and animal waste used especially as a source of fuel.
Reactive flash volatilization (RFV) is a chemical process that rapidly converts nonvolatile solids and liquids to volatile compounds by thermal decomposition for integration with catalytic chemistries.
Sinapaldehyde is an organic compound with the formula HO(CH3O)2C6H2CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol, a lignol that is a major precursor to lignin.
Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.
Coniferyl aldehyde is an organic compound with the formula HO(CH3O)C6H3CH=CHCHO. It is a derivative of cinnamaldehyde, featuring 4-hydroxy and 3-methoxy substituents. It is a major precursor to lignin.
Hydrothermal liquefaction (HTL) is a thermal depolymerization process used to convert wet biomass, and other macromolecules, into crude-like oil under moderate temperature and high pressure. The crude-like oil has high energy density with a lower heating value of 33.8-36.9 MJ/kg and 5-20 wt% oxygen and renewable chemicals. The process has also been called hydrous pyrolysis.
The term "lignin characterization" refers to a group of activities within lignin research aiming at describing the characteristics of a lignin by determination of its most important properties. Most often, this term is used to describe the characterization of technical lignins by means of chemical or thermo-chemical analysis. Technical lignins are lignins isolated from various biomasses during various kinds of technical processes such as wood pulping. The most common technical lignins include lignosulphonates, kraft lignins, organosolv lignins, soda lignins and lignin residue after enzymatic treatment of biomass.
Levoglucosenone is an organic compound with the formula [OCH2(CH)4CO2]. A pale yellow liquid, it is an unsaturated bicyclic ketone-diether formed from levoglucosan by loss of two molecules of water. As a product of the acid-catalysed pyrolysis of cellulose, D-glucose, and levoglucosan, this liquid hydrocarbon is of interest as a biofuel and biofeedstock.