KR20030082984A - 레불린산으로부터 5-메틸부티로락톤의 제조 방법 - Google Patents
레불린산으로부터 5-메틸부티로락톤의 제조 방법 Download PDFInfo
- Publication number
- KR20030082984A KR20030082984A KR10-2003-7011976A KR20037011976A KR20030082984A KR 20030082984 A KR20030082984 A KR 20030082984A KR 20037011976 A KR20037011976 A KR 20037011976A KR 20030082984 A KR20030082984 A KR 20030082984A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- catalyst
- carbon
- metal catalyst
- levulinic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 229940040102 levulinic acid Drugs 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 40
- 229910052751 metal Inorganic materials 0.000 claims abstract description 24
- 239000002184 metal Substances 0.000 claims abstract description 24
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 5
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- 239000010948 rhodium Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- -1 silica Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27658101P | 2001-03-16 | 2001-03-16 | |
| US60/276,581 | 2001-03-16 | ||
| PCT/US2002/007878 WO2002074760A1 (en) | 2001-03-16 | 2002-03-14 | Production of 5-methylbutyrolactone from levulinic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20030082984A true KR20030082984A (ko) | 2003-10-23 |
Family
ID=23057217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2003-7011976A Ceased KR20030082984A (ko) | 2001-03-16 | 2002-03-14 | 레불린산으로부터 5-메틸부티로락톤의 제조 방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6617464B2 (https=) |
| EP (1) | EP1368333A1 (https=) |
| JP (1) | JP2005500987A (https=) |
| KR (1) | KR20030082984A (https=) |
| CN (1) | CN1498215A (https=) |
| BR (1) | BR0208248A (https=) |
| CA (1) | CA2437740A1 (https=) |
| WO (1) | WO2002074760A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011031023A3 (ko) * | 2009-09-11 | 2011-07-14 | 한국화학연구원 | 탄소수 4 내지 6의 유기산으로부터 고리화된 화합물을 제조하는 방법 |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6946563B2 (en) * | 2003-06-16 | 2005-09-20 | E. I. Du Pont De Nemours And Company | Production of 5-methyl-dihydro-furan-2-one from levulinic acid in supercritical media |
| US20060100449A1 (en) * | 2004-11-10 | 2006-05-11 | Manzer Leo E | Integrated two-step process for the production of gamma-methyl-alpha-methylene-gamma-butyrolactone from levulinic acid and hydrogen |
| US20060100448A1 (en) * | 2004-11-10 | 2006-05-11 | Manzer Leo E | Process for the production of Y-methyl-A-methylene-Y-butyrolactone from reaction of levulinic acid and hydrogen in the liquid phase followed by reaction of crude-Y-valerolactone and formaldehyde |
| US20060100447A1 (en) * | 2004-11-10 | 2006-05-11 | Manzer Leo E | Process for the production of y-methyl-a-methylene-y-butyrolactone from reaction of levulinic acid and hydrogen with recycle of unreacted levulinic acid followed by reaction of crude y-valerolactone and formaldehyde, both reactions being carried out in the supercritical or near-critical fluid phase |
| US20060100450A1 (en) * | 2004-11-10 | 2006-05-11 | Manzer Leo E | Process for the production of y-methyl-a-methylene-y-butyrolactone from reaction of levulinic acid and hydrogen followed by reaction of crude y-valerolactone and formaldehyde, both reactions being carried out in the supercritical or near-critical fluid phase |
| EP1828095B1 (en) | 2004-12-23 | 2011-10-05 | Shell Internationale Research Maatschappij B.V. | A process for the hydrogenation of a lactone or of a carboxylic acid or an ester having a gamma-carbonyl group |
| CN101679183A (zh) * | 2007-05-22 | 2010-03-24 | 国际壳牌研究有限公司 | 将乙酰丙酸转化为戊酸的方法 |
| US20090069452A1 (en) * | 2007-09-07 | 2009-03-12 | Range Fuels, Inc | Methods and apparatus for producing ethanol from syngas with high carbon efficiency |
| US7923405B2 (en) * | 2007-09-07 | 2011-04-12 | Range Fuels, Inc. | Cobalt-molybdenum sulfide catalyst materials and methods for ethanol production from syngas |
| US20090156392A1 (en) * | 2007-12-14 | 2009-06-18 | Range Fuels, Inc. | Catalyst compositions and methods for alcohol production from synthesis gas |
| US8354357B2 (en) * | 2008-09-04 | 2013-01-15 | Albemarle Corporation | Cobalt-molybdenum sulfide catalyst materials and methods for stable alcohol production from syngas |
| US8586801B2 (en) | 2008-09-04 | 2013-11-19 | Albemarle Corporation | Cobalt-molybdenum sulfide catalyst materials and methods for stable alcohol production from syngas |
| US8383691B2 (en) * | 2009-06-30 | 2013-02-26 | Albemarle Corporation | Methods of making improved cobalt-molybdenum-sulfide catalyst compositions for higher alcohol synthesis |
| US8580978B2 (en) | 2009-08-07 | 2013-11-12 | Shell Oil Company | Process for preparing a hydroxyacid or hydroxyester |
| US9012680B2 (en) | 2009-08-07 | 2015-04-21 | Shell Oil Company | Process for preparing an ester |
| US20110112326A1 (en) * | 2009-08-07 | 2011-05-12 | Jean-Paul Lange | Process for hydrogenation |
| EP2462100A1 (en) | 2009-08-07 | 2012-06-13 | Shell Internationale Research Maatschappij B.V. | Process for hydrogenation |
| CN101805316A (zh) * | 2010-04-22 | 2010-08-18 | 复旦大学 | 一种用负载型铱催化剂制备γ-戊内酯的方法 |
| PL2537840T3 (pl) | 2011-06-21 | 2013-12-31 | Dsm Ip Assets Bv | Sposób wytwarzania walerolaktonu z kwasu lewulinowego |
| PL2573064T3 (pl) * | 2011-09-23 | 2014-04-30 | Dsm Ip Assets Bv | Sposób wytwarzania estrów kwasu alkenowego z laktonów |
| CN102558108B (zh) * | 2011-12-22 | 2014-07-16 | 南开大学 | 用铱-钳形配体络合物催化剂制备γ-戊内酯的方法 |
| CN102617519B (zh) * | 2012-03-05 | 2014-08-13 | 中国石油大学(华东) | 由乙酰丙酸加氢制备γ-戊内酯的方法 |
| EP2970166A4 (en) | 2013-03-15 | 2016-11-23 | Gfbiochemicals Ltd | PROCESS FOR PRODUCING OCTANE DIOIC ACID, PRECURSORS AND DERIVATIVES |
| KR101333055B1 (ko) | 2013-04-26 | 2013-11-27 | 박유성 | 발전기 및 그 제조방법 |
| FR3008970B1 (fr) * | 2013-07-25 | 2015-08-21 | IFP Energies Nouvelles | Procede de production d'alcools par hydrogenation catalytique d'acide levulinique en une etape |
| EP3204366B1 (en) | 2014-10-08 | 2020-01-08 | Council of Scientific and Industrial Research | A process for the preparation of gamma-valerolactone by catalytic hydrogenation of levulinic acid using ru-based catalysts |
| CN104496945B (zh) * | 2015-01-08 | 2016-06-22 | 山西大学 | 一种γ-戊内酯的制备方法 |
| US10144718B2 (en) | 2015-02-18 | 2018-12-04 | Dsm Ip Assets B.V. | Continuous hydrogenation of levulinic acid |
| WO2017061865A1 (en) | 2015-10-06 | 2017-04-13 | Avantium Knowledge Centre B.V. | Process for the preparation of gamma-valerolactone |
| JP6558446B2 (ja) * | 2015-11-16 | 2019-08-14 | 宇部興産株式会社 | γ−バレロラクトンの製造方法 |
| FI127020B (en) | 2015-12-23 | 2017-09-29 | Neste Oyj | Selective method for the conversion of levulinic acid to gamma valerolactone |
| FI127191B (en) | 2015-12-23 | 2018-01-15 | Neste Oyj | Combined production of levulinic acid and furfural from biomass |
| US9878967B2 (en) | 2015-12-23 | 2018-01-30 | Iowa State University Research Foundation, Inc. | Method of converting levulinic acid or a derivative thereof to hydrocarbons and hydrogen, and methods of the production of hydrocarbons and hydrogen |
| CN108014798B (zh) * | 2016-11-04 | 2020-10-30 | 中国石油化工股份有限公司 | 加氢制备2-甲基四氢呋喃的催化剂及其使用方法 |
| CN109395723B (zh) * | 2018-12-10 | 2021-08-31 | 郑州师范学院 | 一种乙酰丙酸加氢制γ-戊内酯Ru-Al催化体系及其制备方法和应用 |
| CN110548505A (zh) * | 2019-08-20 | 2019-12-10 | 青岛科技大学 | 核壳型催化剂及其合成方法、以及其催化乙酰丙酸制备γ-戊内酯的方法 |
| SE546822C2 (en) * | 2023-02-01 | 2025-02-25 | Eco Oil Miljoebraenslen I Sverige Ab | Process for continuous hydrogenation of aqueous levulinic acid to y-valerolactone and its tandem conversion to high octane gasoline range hydrocarbons |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2368366A (en) * | 1942-08-21 | 1945-01-30 | Monsanto Chemicals | Process for the production of lactones |
| US2786852A (en) * | 1953-08-19 | 1957-03-26 | Quaker Oats Co | Process of preparing gammavalerolactone |
| GB896949A (en) * | 1957-12-14 | 1962-05-23 | Basf Ag | Improvements in the production of proto-anemonin and its homologues |
| NL8103173A (nl) * | 1981-07-02 | 1983-02-01 | Stamicarbon | Werkwijze voor de bereiding van een 5-alkyl-butyrolacton. |
| US5883266A (en) * | 1998-01-16 | 1999-03-16 | Battelle Memorial Institute | Hydrogenated 5-carbon compound and method of making |
-
2002
- 2002-03-14 KR KR10-2003-7011976A patent/KR20030082984A/ko not_active Ceased
- 2002-03-14 CA CA002437740A patent/CA2437740A1/en not_active Abandoned
- 2002-03-14 BR BR0208248-9A patent/BR0208248A/pt not_active IP Right Cessation
- 2002-03-14 CN CNA028067231A patent/CN1498215A/zh active Pending
- 2002-03-14 EP EP02725171A patent/EP1368333A1/en not_active Withdrawn
- 2002-03-14 WO PCT/US2002/007878 patent/WO2002074760A1/en not_active Ceased
- 2002-03-14 JP JP2002573769A patent/JP2005500987A/ja not_active Withdrawn
- 2002-03-15 US US10/099,354 patent/US6617464B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011031023A3 (ko) * | 2009-09-11 | 2011-07-14 | 한국화학연구원 | 탄소수 4 내지 6의 유기산으로부터 고리화된 화합물을 제조하는 방법 |
| KR101231615B1 (ko) * | 2009-09-11 | 2013-02-08 | 한국화학연구원 | 탄소수 4 내지 6의 유기산으로부터 고리화된 화합물을 제조하는 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2437740A1 (en) | 2002-09-26 |
| US6617464B2 (en) | 2003-09-09 |
| CN1498215A (zh) | 2004-05-19 |
| EP1368333A1 (en) | 2003-12-10 |
| US20030055270A1 (en) | 2003-03-20 |
| JP2005500987A (ja) | 2005-01-13 |
| BR0208248A (pt) | 2004-03-02 |
| WO2002074760A1 (en) | 2002-09-26 |
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