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Gamma-Valerolactone

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gamma-Valerolactone[1]
Skeletal formula of γ-valerolactone
Ball-and-stick model of the γ-valerolactone molecule
Names
IUPAC name
5-Methyloxolan-2-one
Other names
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  • 5-Methyldihydrofuran-2(3H)-one,
  • 4-Pentanolide,
  • 4-Valerolactone,
  • 4-Pentalactone,
  • 4-Hydroxypentanoic acid lactone
Identifiers
CAS Number
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3D model (JSmol)
 Page Àtụ:Plainlist/styles.css has no content.
Beilstein Reference
 80420
ChEBI Page Àtụ:Plainlist/styles.css has no content.
ChEMBL Page Àtụ:Plainlist/styles.css has no content.
ChemSpider Page Àtụ:Plainlist/styles.css has no content.
<span title="echa.europa.eu">ECHA InfoCard</span> 100.003.245 Edit this at Wikidata
<span title="European Community number (chemical identifier)">EC Number</span> Page Àtụ:Plainlist/styles.css has no content.
  • 203-569-5
PubChem <abbr title="<nowiki>Compound ID</nowiki>">CID
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UNII Page Àtụ:Plainlist/styles.css has no content.
UN number 1224
CompTox Dashboard (<abbr title="<nowiki>U.S. Environmental Protection Agency</nowiki>">EPA)
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InChI
  • InChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3 checkY
    Key: GAEKPEKOJKCEMS-UHFFFAOYSA-N checkY
  • InChI=1/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3
    Key: GAEKPEKOJKCEMS-UHFFFAOYAX
SMILES
  • CC1CCC(=O)O1
Properties
Chemical formula
 C5H8O2
Molar mass 100.116
Appearance colorless liquid
Density 1.0546 g/mL (20 °C) [2]
Melting point −31 °C (−24 °F; 242 K)
Boiling point 205 °C (401 °F; 478 K)[2]
Solubility in water
 >=100 mg/mL
Refractive index (nD)
 1.4333 (20 °C)
Thermochemistry
Std enthalpy of<br><br>formation (ΔfH⦵298)
 -461.3 kJ·mol−1
Std enthalpy of<br><br>combustion (ΔcH⦵298)
 -2649.6 kJ·mol−1
Hazards
<b>GHS</b> labelling:
Pictograms
 GHS07: Exclamation mark
Signal word
 Warning
Hazard statements
 H319
<b>NFPA 704</b> (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
<span style="color:black;" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform">2</span>
<span style="color:black;" title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel">2</span>
<span style="color:black;" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen">0</span>
Flash point 81 °C (178 °F; 354 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

γ-Valerolactone (GVL) bụ ihe na-emepụta ihe na usoro C5H8O2. Mmiri a na-enweghị ụcha bụ otu n'ime lactones a na-ahụkarị. GVL bụ chiral mana a na-ejikarị ya eme ihe dị ka racemate. A na-enweta ya n'ụzọ dị mfe site na cellulosic biomass ndị na ma bụrụ ihe nwere ike ịgba ọkụ na ihe na-agbanye mmiri.

GVL na-akpa àgwà dị ka ọgwụ na-emepụta γ-hydroxyvaleric acid (GHV), ọgwụ nwere mmetụta yiri nke γ-hydrexybutyric acid (GHB), ọ bụ ezie na ọ nwere ike dị ala ma e jiri ya tụnyere.[3] N'ihi na a na-achịkwa GHB n'ọtụtụ akụkụ nke abụọ ahụ na ihe niile nke obodo ụwa, ebe GVL abụghị, GVL enwetala ewu ewu dị ka onye na-anọchi GHB.[3][4]

Nchịkọta

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A na-emepụta GVL site na levulinic acid, nke a na-enweta site na hexoses. N'ime usoro a na-ahụkarị ndị mmadụ na nke ukwu nke ụwa họrọ site na ndi isi, cellulosic biomasses, dị ka ọka stover, sawgrass, ma ọ bụ osisi, na-agbanye na glucose na shuga ndị ọzọ site na iji acid catalysts. Enwere ike imebi glucose a na-enweta site na hydroxymethylfurfural iji mepụta formic acid na levulinic acid, nke na-agbagharị na mgbanaka mgbanaka mgbagwoju anya, nke enwere ike hydrogenated na gamma-valerolactone, nke nwere ike itinye ya dịka mmanụ mmiri.[5]

Ihe ndị nwere ike itinye n'ọrụ

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A chọpụtala GVL dị ka ihe nwere ike ịgbaze ndị na eme ka anyị si e akwụkwọ ndụ akwụkwọ ndụ. N'ihi ísì ahịhịa ya, a na-eji ya eme ihe na ụlọ ọrụ na-esi ísì ụtọ.[6] Ọ bụ isomer nke δ-valerolactone.

Ihe ndị nwere ike ime ka ọ bụrụ mmanụ

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Ebe ọ bụ na a na-enweta ya n'ụzọ dị mfe site na glucose, a chọpụtala GVL dị ka "ihe na-acha akwụkwọ ndụ akwụkwọ ndụ".[7] GVL na-ejigide 97% nke ike nke glucose ma nwee ike ịgwakọta ya n'onwe ya na gasoline ebe ọ na-arụ ọrụ dịka ethanol / gasoline mixtures.[8][9] Otú ọ dị, n'ihi oke ngwakọta maka iji ya na injin ọkụ, ọ nwere ike ịdị irè karị iji gbanwee GVL ka ọ bụrụ alkenes mmiri na eme ka ndị mmadụ na ímé ihe ọ bụla (ma ọ bụ alkanes). Nzọụkwụ mbụ na usoro a bụ mmeghe mgbanaka nke GVL iji mepụta ngwakọta nke pentenoic acid. Enwere ike decarboxylated acid ndị a iji mepụta butene na CO2. Enwere ike iji zeolite catalysts mee mgbanwe ndị a.[10] Mgbe mmiri gwụsịrị iyi a, enwere ike oligomerized ngwaahịa ndị ahụ na nrụgide dị elu na ọnụnọ nkè ikike asụsụ obodo acid-catalyst iji mepụta alkenes nwere ịdị arọ dị elu, maka gasoline na ngwa mmanụ ndị ọzọ.[11]

Otu n'ime uru ndị bụ isi na-enye ohere ka GVL bụrụ ihe na-eme ka ihe dị ndụ bụrụ ihe bara uru bụ na ọ dị ọnụ ala iji mepụta. N'iji ihe oriri dị ọnụ ala, enwere ike ịmepụta mmanụ a na ọnụahịa ọnọdụ na akụkọ ụra akpa nwa dị n'etiti 2-3 US $ / galọn.[8] Mgbanwe nke GVL na alkenes nwere ike ibugharị mmanụ chọrọ naanị usoro nwere reactors abụọ, ndị na-ekewa akụkụ abụọ, na ndokwa mgbapụta dị mfe maka nnyefe nri GVL mmiri. Ebe ọ bụ na a chọghị iji ihe ndị na-akpali akpali dị oké ọnụ ahịa, nke a na-ebelata ọnụahịa niile nke mmepụta mmanụ.[10]

Mmetụta nke ihe ndị sitere na biomass

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Ewezuga uru ya dị ka ihe nwere ike ịba ụba n'onwe ya, gamma-valerolactone egosila nkwa na mmepụta thermocatalytic nke ụlọ nyocha nke carbohydrates soluble site na stover ọka na osisi na nnukwu ihe. Biomass na-emeghachi omume na ngwakọta mmiri, sulfuric acid, na gamma-valerolactone, n'onwe ya sitere na biomass. Gamma-valerolactone na-akwalite thermocatalytic hydrolysis n'ime monosaccharides site na solubilization zuru oke nke ihe a na-emepụta, gụnyere lignins. Enwere ike iweghachite ngwaahịa saccharide site na lactone n'ime mmiri site na mgbakwunye anti-solvent nke nnu ma ọ bụ mmiri carbon dioxide. Enwere ike iji ngwaahịa ahụ mee ihe dị ka ihe oriri maka ịmepụta furans ma ọ bụ ethanol na nnukwu mmepụta, ebe a na-eweghachi gamma-valerolactone na okirikiri catalytic.[12]

Nhazi nke Membrane

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A mụọla Gamma-Valerolactone ma gosipụta ikike ịkwadebe ngwọta ọgwụ maka imepụta polymer membranes. N'ihi nsị nke solvents ọdịnala, a nyochara solvents akwụkwọ ndụ akwụkwọ ndụ n'afọ ndị na-adịbeghị anya na ọ ga eme.[13] N'ihi ọdịdị ya na-ahụ maka gburugburu ebe obibi, Gamma-Valerolactone gosipụtara ikike ịmepụta polysulfone membranes dị ka co-solvent.

Hụkwa

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  • δ-Valerolactone
  • Valeric acid
  • 1,4-Butanediol (1,4-BD)
  • γ-Butyrolactone (GBL)

Ntụaka

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  1. ↑ NIH National Toxicology Program
  2. ↑ 2.0 2.1 Kpọpụta njehie: Invalid <ref> tag; no text was provided for refs named Baird2019
  3. ↑ 3.0 3.1 (2013) "Uptake of gamma-valerolactone--detection of gamma-hydroxyvaleric acid in human urine samples". J Anal Toxicol 37 (4): 250–4. DOI:10.1093/jat/bkt013. PMID 23486087. 
  4. ↑ Fred Smith (31 December 2004). Handbook of Forensic Drug Analysis. Academic Press, 462–. ISBN 978-0-08-047289-8. 
  5. ↑ Huber (2006). "Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering". Chemical Reviews 106 (9): 4044–4098. DOI:10.1021/cr068360d. PMID 16967928. 
  6. ↑ GoodScentsCompany.com
  7. ↑ Huber (2007). "Synergies between Bio- and Oil Refineries for the Production of Fuels from Biomass". Angewandte Chemie International Edition 46 (38): 7184–7201. DOI:10.1002/anie.200604504. PMID 17610226. 
  8. ↑ 8.0 8.1 Savage (2011). "Fuel Options: The Ideal Biofuel". Nature 474 (7352): S9–S11. DOI:10.1038/474S09a. PMID 21697843. 
  9. ↑ Horváth (2008). "γ-Valerolactone—a sustainable liquid for energy and carbon-based chemicals". Green Chemistry 10 (2): 238–242. DOI:10.1039/b712863k. 
  10. ↑ 10.0 10.1 Bond (2010). "Integrated Catalytic Conversion of γ-Valerolactone to Liquid Alkenes for Transportation Fuels". Science 327 (5969): 1110–1114. DOI:10.1126/science.1184362. PMID 20185721. 
  11. ↑ Mantilla, A. (2005). "Oligomerization of isobutene on sulfated titania: Effect of reaction conditions on selectivity". Catalysis Today 107–108: 707–712. DOI:10.1016/j.cattod.2005.07.153. 
  12. ↑ Luterbacher (2014). "Nonenzymatic Sugar Production from Biomass Using Biomass-Derived gamma-Valerolactone". Science 343 (6168): 277–280. DOI:10.1126/science.1246748. PMID 24436415. 
  13. ↑ Figoli (2014-07-03). "Towards non-toxic solvents for membrane preparation: a review" (in en). Green Chemistry 16 (9): 4034. DOI:10.1039/c4gc00613e. ISSN 1463-9262. 
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