Levoglucosan

Last updated
Levoglucosan
Levoglucosan.png
Levoglucosan-3D-vdW.png
Names
Preferred IUPAC name
(1R,2S,3S,4R,5R)-6,8-Dioxabicyclo[3.2.1]octane-2,3,4-triol
Other names
1,6-Anhydro-beta-glucopyranose
Leucoglucosan
Identifiers
3D model (JSmol)
80998
ChEBI
ChemSpider
ECHA InfoCard 100.007.142 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-855-0
MeSH 1,6-Anhydro-beta-glucopyranose
PubChem CID
UNII
  • InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2 Yes check.svgY
    Key: TWNIBLMWSKIRAT-UHFFFAOYSA-N Yes check.svgY
  • OC1C2COC(O2)C(O)C1O
Properties
C6H10O5
Molar mass 162.141 g·mol−1
AppearanceColorless crystals
Density 1.688 g·cm−3 (predicted)
Melting point 182 to 184 °C (360 to 363 °F; 455 to 457 K)
Boiling point 384 °C (723 °F; 657 K) predicted
log P -0.04 (predicted)
Vapor pressure 24.1 μPa (predicted)
Hazards
Flash point 185.9 °C (366.6 °F; 459.0 K) (predicted)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Levoglucosan (C6H10O5) is an organic compound with a six-carbon ring structure formed from the pyrolysis of carbohydrates, such as starch and cellulose. [1] As a result, levoglucosan is often used as a chemical tracer for biomass burning in atmospheric chemistry studies, particularly with respect to airborne particulate matter. Along with other tracers such as potassium, oxalate, and gaseous acetonitrile, [2] levoglucosan has been shown to be highly correlated with regional fires. This is because the gas emitted by the pyrolysis of wood (biomass) contains significant amounts of levoglucosan.

Levoglucosan has been described as "an unequivocal biomass burning tracer" in the context of forest and brush fires. [3] But the anhydrosugar has only been found detectable in low temperature samples (150-350 °C), meaning that its value as an indicator for smoke from controlled biomass combustion in, for instance, modern domestic wood stoves which operate at temperatures above 500 °C, is "very doubtful". [4] Levoglucosan is a marker for coal combustion as well as wood. [5]

The hydrolysis of levoglucosan generates the fermentable sugar glucose. Levoglucosan can be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers.

Related Research Articles

<span class="mw-page-title-main">Combustion</span> Chemical reaction

Combustion, or burning, is a high-temperature exothermic redox chemical reaction between a fuel and an oxidant, usually atmospheric oxygen, that produces oxidized, often gaseous products, in a mixture termed as smoke. Combustion does not always result in fire, because a flame is only visible when substances undergoing combustion vaporize, but when it does, a flame is a characteristic indicator of the reaction. While activation energy must be supplied to initiate combustion, the heat from a flame may provide enough energy to make the reaction self-sustaining.

<span class="mw-page-title-main">Cellulose</span> Polymer of glucose and structural component of cell wall of plants and green algae

Cellulose is an organic compound with the formula (C
6
H
10
O
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%.

<span class="mw-page-title-main">Smoke</span> Mass of airborne particulates and gases

Smoke is a suspension of airborne particulates and gases emitted when a material undergoes combustion or pyrolysis, together with the quantity of air that is entrained or otherwise mixed into the mass. It is commonly an unwanted by-product of fires, but may also be used for pest control (fumigation), communication, defensive and offensive capabilities in the military, cooking, or smoking. It is used in rituals where incense, sage, or resin is burned to produce a smell for spiritual or magical purposes. It can also be a flavoring agent and preservative.

<span class="mw-page-title-main">Pyrolysis</span> Thermal decomposition of materials at elevated temperatures in an inert atmosphere

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".

<span class="mw-page-title-main">Soot</span> Impure carbon particles resulting from the incomplete combustion of hydrocarbons

Soot is a mass of impure carbon particles resulting from the incomplete combustion of hydrocarbons. It is more properly restricted to the product of the gas-phase combustion process but is commonly extended to include the residual pyrolysed fuel particles such as coal, cenospheres, charred wood, and petroleum coke that may become airborne during pyrolysis and that are more properly identified as cokes or char.

<span class="mw-page-title-main">Solid fuel</span>

Solid fuel refers to various forms of solid material that can be burnt to release energy, providing heat and light through the process of combustion. Solid fuels can be contrasted with liquid fuels and gaseous fuels. Common examples of solid fuels include wood, charcoal, peat, coal, hexamine fuel tablets, dry dung, wood pellets, corn, wheat, rye, and other grains. Solid fuels are extensively used in rocketry as solid propellants. Solid fuels have been used throughout human history to create fire and solid fuel is still in widespread use throughout the world in the present day.

<span class="mw-page-title-main">Wood fuel</span> Wood used as fuel for combustion

Wood fuel is a fuel such as firewood, charcoal, chips, sheets, pellets, and sawdust. The particular form used depends upon factors such as source, quantity, quality and application. In many areas, wood is the most easily available form of fuel, requiring no tools in the case of picking up dead wood, or few tools, although as in any industry, specialized tools, such as skidders and hydraulic wood splitters, have been developed to mechanize production. Sawmill waste and construction industry by-products also include various forms of lumber tailings.

<span class="mw-page-title-main">Thermogravimetric analysis</span> Thermal method of analysis

Thermogravimetric analysis or thermal gravimetric analysis (TGA) is a method of thermal analysis in which the mass of a sample is measured over time as the temperature changes. This measurement provides information about physical phenomena, such as phase transitions, absorption, adsorption and desorption; as well as chemical phenomena including chemisorptions, thermal decomposition, and solid-gas reactions.

<span class="mw-page-title-main">Black carbon</span> Component of fine particulate matter

Chemically, black carbon (BC) is a component of fine particulate matter. Black carbon consists of pure carbon in several linked forms. It is formed through the incomplete combustion of fossil fuels, biofuel, and biomass, and is one of the main types of particle in both anthropogenic and naturally occurring soot. Black carbon causes human morbidity and premature mortality. Because of these human health impacts, many countries have worked to reduce their emissions, making it an easy pollutant to abate in anthropogenic sources.

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.

<span class="mw-page-title-main">Lignocellulosic biomass</span>

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.

<span class="mw-page-title-main">Biochar</span> Lightweight black residue, made of carbon and ashes, after pyrolysis of biomass

Biochar is the lightweight black residue, made of carbon and ashes, remaining after the pyrolysis of biomass, and is a form of charcoal. Biochar is defined by the International Biochar Initiative as "the solid material obtained from the thermochemical conversion of biomass in an oxygen-limited environment". Biochar is a stable solid that is rich in pyrogenic carbon and can endure in soil for thousands of years.

<i>gamma</i>-Valerolactone Chemical compound

γ-Valerolactone (GVL) is an organic compound with the formula C5H8O2. This colourless liquid is one of the more common lactones. GVL is chiral but is usually used as the racemate. It is readily obtained from cellulosic biomass and is a potential fuel and green solvent.

<span class="mw-page-title-main">Biomass briquettes</span>

Biomass briquettes are a biofuel substitute made of biodegradable green waste with lower emissions of greenhouses gases and carbon dioxide then traditional fuel sources. This fuel source is used as an alternative for harmful biofuels. Briquettes are used for heating, cooking fuel, and electricity generation usually in developing countries that do not have access to more traditional fuel sources. Biomass briquettes have become popular in developed countries due to the accessibility, and eco-friendly impact. The briquettes can be used in the developed countries for producing electricity from steam power by heating water in boilers.

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.

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.

<span class="mw-page-title-main">Aethalometer</span> Instrument for measuring particle concentration

An aethalometer is an instrument for measuring the concentration of optically absorbing (‘black’) suspended particulates in a gas colloid stream; commonly visualized as smoke or haze, often seen in ambient air under polluted conditions. The word aethalometer is derived from the Classical Greek verb aethaloun, meaning "to blacken with soot". The aethalometer, a device used for measuring black carbon in atmospheric aerosols, was initially deployed in 1980 and was first commercialized by Magee Scientific.

In chemistry, brown carbon (Cbrown/BrC) is brown smoke released by the combustion of organic matter. It coexists with black carbon when released in the atmosphere.

Joyce Penner is an atmospheric scientist known for her research on climate change, especially on the impact of aerosols and clouds.

Particulate pollution is pollution of an environment that consists of particles suspended in some medium. There are three primary forms: atmospheric particulate matter, marine debris, and space debris. Some particles are released directly from a specific source, while others form in chemical reactions in the atmosphere. Particulate pollution can be derived from either natural sources or anthropogenic processes.

References

  1. Lakshmanan, Chambra M.; Hoelscher, Harold E. (1970). "Production of Levoglucosan by Pyrolysis of Carbohydrates. Pyrolysis in Hot Inert Gas Stream". Industrial & Engineering Chemistry Product Research and Development. 9: 57–59. doi:10.1021/i360033a011.
  2. Aiken, A. C.; De Foy, B.; Wiedinmyer, C.; Decarlo, P. F.; Ulbrich, I. M.; Wehrli, M. N.; Szidat, S.; Prevot, A. S. H.; et al. (2010). "Mexico city aerosol analysis during MILAGRO using high resolution aerosol mass spectrometry at the urban supersite (T0) – Part 2: Analysis of the biomass burning contribution and the non-fossil carbon fraction" (PDF). Atmospheric Chemistry and Physics. 10 (12): 5315. Bibcode:2010ACP....10.5315A. doi: 10.5194/acp-10-5315-2010 .
  3. "Identification of biomass burning tracers" (PDF). Euro 'Milestone' Survey. Retrieved 20 March 2015.
  4. Harrison, Roy M.; Beddows, David C.S.; Jones, Alan M.; Calvo, Ana; Alves, Célia; Pio, Casimiro (2013). "An evaluation of some issues regarding the use of aethalometers to measure woodsmoke concentrations" (PDF). Atmospheric Environment. 80: 540–548. Bibcode:2013AtmEn..80..540H. doi:10.1016/j.atmosenv.2013.08.026.
  5. Yan, Caiqing; Zheng, Mei; Sullivan, Amy P.; Shen, Guofeng; Chen, Yingjun; Wang, Shuxiao; Zhao, Bin; Cai, Siyi; Desyaterik, Yury; Li, Xiaoying; Zhou, Tian; Gustafsson, Örjan; Collett, Jeffrey L. (2018). "Residential Coal Combustion as a Source of Levoglucosan in China". Environmental Science & Technology. 52 (3): 1665–1674. Bibcode:2018EnST...52.1665Y. doi:10.1021/acs.est.7b05858. PMID   29244948.