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Levoglucosan

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
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
  • 498-07-7 Y
3D model (JSmol)
  • Interactive image
80998
ChEBI
  • CHEBI:30997
ChemSpider
  • 9587432 Y
ECHA InfoCard 100.007.142
EC Number
  • 207-855-0
MeSH 1,6-Anhydro-beta-glucopyranose
  • 2724705
UNII
  • 5132N17FSD Y
  • DTXSID90904321
  • InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2 Y
    Key: TWNIBLMWSKIRAT-UHFFFAOYSA-N Y
  • OC1C2COC(O2)C(O)C1O
Properties
C6H10O5
Molar mass 162.141 g·mol−1
Appearance Colorless 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 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.

References edit

  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.

levoglucosan, c6h10o5, organic, compound, with, carbon, ring, structure, formed, from, pyrolysis, carbohydrates, such, starch, cellulose, result, levoglucosan, often, used, chemical, tracer, biomass, burning, atmospheric, chemistry, studies, particularly, with. 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 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 glucopyranoseLeucoglucosan Identifiers CAS Number 498 07 7 Y 3D model JSmol Interactive image Beilstein Reference 80998 ChEBI CHEBI 30997 ChemSpider 9587432 Y ECHA InfoCard 100 007 142 EC Number 207 855 0 MeSH 1 6 Anhydro beta glucopyranose PubChem CID 2724705 UNII 5132N17FSD Y CompTox Dashboard EPA DTXSID90904321 InChI InChI 1S C6H10O5 c7 3 2 1 10 6 11 2 5 9 4 3 8 h2 9H 1H2 YKey TWNIBLMWSKIRAT UHFFFAOYSA N Y SMILES OC1C2COC O2 C O C1O Properties Chemical formula C 6H 10O 5 Molar mass 162 141 g mol 1 Appearance Colorless 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 mPa 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 Infobox references 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 References edit Lakshmanan Chambra M Hoelscher Harold E 1970 Production of Levoglucosan by Pyrolysis of Carbohydrates Pyrolysis in Hot Inert Gas Stream Industrial amp Engineering Chemistry Product Research and Development 9 57 59 doi 10 1021 i360033a011 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 Identification of biomass burning tracers PDF Euro Milestone Survey Retrieved 20 March 2015 Harrison Roy M Beddows David C S Jones Alan M Calvo Ana Alves Celia 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 Yan Caiqing Zheng Mei Sullivan Amy P Shen Guofeng Chen Yingjun Wang Shuxiao Zhao Bin Cai Siyi Desyaterik Yury Li Xiaoying Zhou Tian Gustafsson Orjan Collett Jeffrey L 2018 Residential Coal Combustion as a Source of Levoglucosan in China Environmental Science amp Technology 52 3 1665 1674 Bibcode 2018EnST 52 1665Y doi 10 1021 acs est 7b05858 PMID 29244948 Retrieved from https en wikipedia org w index php title Levoglucosan amp oldid 1170346096, wikipedia, wiki, book, books, library,

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