Gamma-Valerolactone
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| Names | |
|---|---|
| IUPAC name
5-Methyloxolan-2-one | |
Other names
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| Identifiers | |
CAS Number |
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3D model (JSmol) |
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Beilstein Reference |
80420 |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| <span title="echa.europa.eu">ECHA InfoCard</span> | 100.003.245 |
| <span title="European Community number (chemical identifier)">EC Number</span> |
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PubChem <abbr title="<nowiki>Compound ID</nowiki>">CID |
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| UNII | |
| UN number | 1224 |
CompTox Dashboard (<abbr title="<nowiki>U.S. Environmental Protection Agency</nowiki>">EPA) |
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InChI
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SMILES
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| 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 |
 |
Signal word |
Warning |
Hazard statements |
H319 |
| <b>NFPA 704</b> (fire diamond) | 
<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).
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
[dezie | dezie ebe o si]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
[dezie | dezie ebe o si]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
[dezie | dezie ebe o si]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
[dezie | dezie ebe o si]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
[dezie | dezie ebe o si]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
[dezie | dezie ebe o si]- δ-Valerolactone
- Valeric acid
- 1,4-Butanediol (1,4-BD)
- γ-Butyrolactone (GBL)
Ntụaka
[dezie | dezie ebe o si]- ↑ NIH National Toxicology Program
- 1 2 Baird, Zachariah Steven; Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Pedegert, Emilie; Alopaeus, Ville (6 Nov 2019). "Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds". International Journal of Thermophysics. 40 (11): 102. Bibcode:2019IJT....40..102B. doi:10.1007/s10765-019-2570-9.
- 1 2 "Uptake of gamma-valerolactone--detection of gamma-hydroxyvaleric acid in human urine samples". J Anal Toxicol. 37 (4): 250–4. 2013. doi:10.1093/jat/bkt013. PMID 23486087.
- ↑ Fred Smith (31 December 2004). Handbook of Forensic Drug Analysis. Academic Press. pp. 462–. ISBN 978-0-08-047289-8.
- ↑ Huber, George W. (2006). "Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering". Chemical Reviews. 106 (9): 4044–4098. doi:10.1021/cr068360d. PMID 16967928.
- ↑ GoodScentsCompany.com
- ↑ Huber, G. W. (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.
- 1 2 Savage, Neil (2011). "Fuel Options: The Ideal Biofuel". Nature. 474 (7352): S9–S11. doi:10.1038/474S09a. PMID 21697843.
- ↑ Horváth, I. T. (2008). "γ-Valerolactone—a sustainable liquid for energy and carbon-based chemicals". Green Chemistry. 10 (2): 238–242. doi:10.1039/b712863k.
- 1 2 Bond, Jesse Q. (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.
- ↑ 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.
- ↑ Luterbacher, Jeremy S. (2014). "Nonenzymatic Sugar Production from Biomass Using Biomass-Derived gamma-Valerolactone". Science. 343 (6168): 277–280. doi:10.1126/science.1246748. PMID 24436415.
- ↑ Figoli, A. (2014-07-03). "Towards non-toxic solvents for membrane preparation: a review". Green Chemistry (in Bekee). 16 (9): 4034. doi:10.1039/c4gc00613e. ISSN 1463-9262.