CA2223600C - Production of levulinic acid from carbohydrate-containing materials - Google Patents
Production of levulinic acid from carbohydrate-containing materials Download PDFInfo
- Publication number
- CA2223600C CA2223600C CA002223600A CA2223600A CA2223600C CA 2223600 C CA2223600 C CA 2223600C CA 002223600 A CA002223600 A CA 002223600A CA 2223600 A CA2223600 A CA 2223600A CA 2223600 C CA2223600 C CA 2223600C
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- carbohydrate
- levulinic acid
- containing material
- seconds
- 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.)
- Expired - Lifetime
Links
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 title claims abstract description 112
- 229940040102 levulinic acid Drugs 0.000 title claims abstract description 56
- 150000001720 carbohydrates Chemical class 0.000 title claims abstract description 28
- 239000000463 material Substances 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000002253 acid Substances 0.000 claims abstract description 26
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims abstract description 17
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 13
- 239000011707 mineral Substances 0.000 claims abstract description 13
- 238000010924 continuous production Methods 0.000 claims abstract description 4
- 239000010802 sludge Substances 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 20
- 239000001913 cellulose Substances 0.000 claims description 12
- 229920002678 cellulose Polymers 0.000 claims description 12
- 239000000543 intermediate Substances 0.000 claims description 11
- 239000000123 paper Substances 0.000 claims description 11
- 239000007806 chemical reaction intermediate Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 9
- 239000002655 kraft paper Substances 0.000 claims description 8
- 239000002023 wood Substances 0.000 claims description 6
- 239000010893 paper waste Substances 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 235000013312 flour Nutrition 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 150000002402 hexoses Chemical class 0.000 abstract description 10
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 235000014633 carbohydrates Nutrition 0.000 description 13
- 239000002002 slurry Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 6
- 239000012263 liquid product Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 238000004537 pulping Methods 0.000 description 4
- 210000000988 bone and bone Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002972 pentoses Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000005523 4-oxopentanoic acid group Chemical group 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000021029 Ramphia Species 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010909 process residue Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008016 vaporization Effects 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
- C07D307/50—Preparation from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/475,630 | 1995-06-07 | ||
| US08/475,630 US5608105A (en) | 1995-06-07 | 1995-06-07 | Production of levulinic acid from carbohydrate-containing materials |
| PCT/US1996/007231 WO1996040609A1 (en) | 1995-06-07 | 1996-05-17 | Production of levulinic acid from carbohydrate-containing materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2223600A1 CA2223600A1 (en) | 1996-12-19 |
| CA2223600C true CA2223600C (en) | 2004-02-10 |
Family
ID=23888434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002223600A Expired - Lifetime CA2223600C (en) | 1995-06-07 | 1996-05-17 | Production of levulinic acid from carbohydrate-containing materials |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5608105A (en0) |
| EP (1) | EP0873294B1 (en0) |
| AU (1) | AU5798596A (en0) |
| CA (1) | CA2223600C (en0) |
| DE (1) | DE69620240T2 (en0) |
| IN (1) | IN185298B (en0) |
| NO (1) | NO308464B1 (en0) |
| WO (1) | WO1996040609A1 (en0) |
Families Citing this family (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030058107A1 (en) * | 2001-09-25 | 2003-03-27 | Ferrier Joseph A. | Personal item locator system |
| KR20040105819A (ko) * | 2002-04-01 | 2004-12-16 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 생물 자원 및 올레핀으로부터 레불린산 에스테르 및포름산 에스테르의 제조 방법 |
| CN1894230A (zh) * | 2003-12-15 | 2007-01-10 | 国际壳牌研究有限公司 | 液化木素纤维素材料的方法 |
| US7378549B2 (en) | 2004-01-26 | 2008-05-27 | Shell Oil Company | Process for the reactive extractive extraction of levulinic acid |
| US7393963B2 (en) * | 2004-12-10 | 2008-07-01 | Archer-Daniels-Midland Company | Conversion of 2,5-(hydroxymethyl)furaldehyde to industrial derivatives, purification of the derivatives, and industrial uses therefor |
| US7317116B2 (en) * | 2004-12-10 | 2008-01-08 | Archer-Daniels-Midland-Company | Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives |
| CN101087749B (zh) * | 2004-12-23 | 2010-06-09 | 国际壳牌研究有限公司 | 内酯或羧酸或具有γ-羰基的酯的加氢方法 |
| US7501062B2 (en) | 2005-02-22 | 2009-03-10 | Shell Oil Company | Process for permeation enhanced reactive extraction of levulinic acid |
| WO2007038362A1 (en) * | 2005-09-22 | 2007-04-05 | E. I. Du Pont De Nemours And Company | Preparation of polytrimethylene ether glycol and copolymers thereof |
| US7625941B2 (en) * | 2005-09-22 | 2009-12-01 | E.I. Du Pont De Nemours And Company | Ionic liquids |
| US7402711B2 (en) | 2005-09-22 | 2008-07-22 | E.I. Du Pont De Nemours And Company | Preparation of poly(tetramethylene) glycol |
| US20070100192A1 (en) * | 2005-10-27 | 2007-05-03 | Harmer Mark A | Olefin isomerization |
| IN262459B (en0) | 2005-11-22 | 2014-08-29 | Segetis Inc | |
| CA2630744C (en) | 2005-11-22 | 2011-05-03 | Aromagen Corporation | Glycerol levulinate ketals and their use |
| US7520905B1 (en) | 2006-02-06 | 2009-04-21 | Gene E Lightner | Additives derived from biomass extracted by biodiesel fuel oil |
| US7700788B2 (en) * | 2006-10-31 | 2010-04-20 | Battelle Memorial Institute | Hydroxymethyl furfural oxidation methods |
| US7815741B2 (en) * | 2006-11-03 | 2010-10-19 | Olson David A | Reactor pump for catalyzed hydrolytic splitting of cellulose |
| US7815876B2 (en) | 2006-11-03 | 2010-10-19 | Olson David A | Reactor pump for catalyzed hydrolytic splitting of cellulose |
| WO2008137639A1 (en) * | 2007-05-02 | 2008-11-13 | Mascoma Corporation | Two-stage method for pretreatment of lignocellulosic biomass |
| RU2339612C1 (ru) * | 2007-07-25 | 2008-11-27 | Институт химии и химической технологии СО РАН | Способ получения левулиновой кислоты кислотно-каталитической конверсией сахарозы |
| FI121541B (fi) | 2008-04-21 | 2010-12-31 | Kemira Oyj | Menetelmä muurahaishapon talteenottamiseksi |
| US8575367B2 (en) * | 2008-09-25 | 2013-11-05 | Segetis, Inc. | Ketal ester derivatives |
| US8119818B2 (en) * | 2008-12-04 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Functionalized N-substituted pyrrolidonium ionic liquids |
| US8138354B2 (en) * | 2008-12-04 | 2012-03-20 | E. I. Du Pont De Nemours And Company | N-substituted pyrrolidonium ionic liquids |
| KR20110098934A (ko) | 2008-12-04 | 2011-09-02 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 이산화탄소 제거 및 이에 유용한 이온성 액체 화합물 |
| KR20110096563A (ko) | 2008-12-04 | 2011-08-30 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 확장된 연결기를 갖는 ｎ-치환된 피롤리도늄 이온성 액체 |
| US8350056B2 (en) * | 2008-12-04 | 2013-01-08 | E I Du Pont De Nemours And Company | Functionalized N-substituted pyrrolidonium ionic liquids |
| US8138371B2 (en) * | 2009-03-11 | 2012-03-20 | Biofine Technologies Llc | Production of formic acid |
| CN102449118A (zh) * | 2009-06-05 | 2012-05-09 | 能源与环境研究中心机构 | 用于由木质纤维素通过乙酰丙酸酯缩合合成燃料组分和化学品的多产物生物精炼系统 |
| US20100312006A1 (en) * | 2009-06-09 | 2010-12-09 | Meadwestvaco Corporation | Production of levulinic acid and levulinate esters from biomass |
| US20110112326A1 (en) * | 2009-08-07 | 2011-05-12 | Jean-Paul Lange | Process for hydrogenation |
| US8580978B2 (en) * | 2009-08-07 | 2013-11-12 | Shell Oil Company | Process for preparing a hydroxyacid or hydroxyester |
| US8362306B2 (en) * | 2009-10-26 | 2013-01-29 | University Of Maine System Board Of Trustees | Energy densification of biomass-derived organic acids |
| US20110173877A1 (en) * | 2009-12-24 | 2011-07-21 | Jeroen Van Buijtenen | Process for preparing a hydrocarbon or mixture of hydrocarbons |
| US7960592B1 (en) | 2010-01-12 | 2011-06-14 | Wisconsin Alumni Research Foundation | Production of methyl-vinyl ketone from levulinic acid |
| CA2796883A1 (en) | 2010-05-10 | 2011-11-17 | Segetis, Inc. | Personal care formulations containing alkyl ketal esters and methods of manufacture |
| AU2011251966B2 (en) | 2010-05-12 | 2014-04-17 | Shell Internationale Research Maatschappij B.V. | Process for liquefying a cellulosic material |
| CN102892864B (zh) | 2010-05-12 | 2015-01-07 | 国际壳牌研究有限公司 | 液化纤维素材料的方法 |
| CN102030646B (zh) * | 2010-11-18 | 2013-09-04 | 郑州大学 | 一种纤维素类物质水解直接转化生成乙酰丙酸乙酯的工艺 |
| AR088124A1 (es) | 2011-04-01 | 2014-05-14 | Dsm Ip Assets Bv | Proceso para la preparacion de esteres de acido alcanoico en un proceso de carbonilacion utilizando ligandos de bifosfato bidentados de paladio |
| AR085717A1 (es) | 2011-04-01 | 2013-10-23 | Dsm Ip Assets Bv | Proceso para producir acido adipico y diesteres del mismo en un proceso de carbonilacion utilizando ligandos bifosfato bidentados de paladio |
| US8389749B2 (en) | 2011-05-25 | 2013-03-05 | Wisconsin Alumni Research Foundation | Method to produce, recover and convert furan derivatives from aqueous solutions using alkylphenol extraction |
| US8399688B2 (en) | 2011-05-25 | 2013-03-19 | Wisconsin Alumni Research Foundation | Production of levulinic acid, furfural, and gamma valerolactone from C5 and C6 carbohydrates in mono- and biphasic systems using gamma-valerolactone as a solvent |
| US8962867B2 (en) | 2011-05-25 | 2015-02-24 | Wisconsin Alumni Research Foundation | Solute-enhanced production of gamma-valerolactone (GVL) from aqueous solutions of levulinic acid |
| US8389761B2 (en) | 2011-05-25 | 2013-03-05 | Wisconsin Alumni Research Foundation | Method to produce and recover levulinic acid and/or gamma-valerolactone from aqueous solutions using alkylphenols |
| WO2012175439A1 (en) | 2011-06-21 | 2012-12-27 | Dsm Ip Assets B.V. | Process to produce valerolactone from levulinic acid |
| EP2537841B1 (en) | 2011-06-22 | 2013-09-25 | DSM IP Assets B.V. | Continuous production of furfural and levulininc acid |
| PL2573064T3 (pl) | 2011-09-23 | 2014-04-30 | Dsm Ip Assets Bv | Sposób wytwarzania estrów kwasu alkenowego z laktonów |
| US20130079566A1 (en) * | 2011-09-27 | 2013-03-28 | Nevada, | Catalytic process for conversion of biomass into hydrocarbon fuels |
| BR112014011672A2 (pt) * | 2011-11-23 | 2017-05-30 | Segetis Inc | processo para preparar ácido levulínico |
| CN102558106B (zh) * | 2011-12-15 | 2014-12-17 | 北京金骄生物质化工有限公司 | 一种利用废弃生物质制备2-甲基四氢呋喃的方法 |
| WO2013092408A1 (en) | 2011-12-20 | 2013-06-27 | Dsm Ip Assets B.V. | Process to produce alkenoic acid esters from lactones |
| US20130168227A1 (en) * | 2011-12-28 | 2013-07-04 | E I Du Pont De Nemours And Company | Process for the production of furfural |
| EP2797906A4 (en) | 2011-12-28 | 2015-06-03 | Du Pont | PROCESS FOR THE PREPARATION OF FURFURAL |
| WO2013102002A1 (en) | 2011-12-28 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Processes for making furfurals |
| WO2013102027A1 (en) | 2011-12-28 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Process for the production of furfural |
| IN2014DN06493A (en0) * | 2012-01-10 | 2015-06-12 | Archer Daniels Midland Co | |
| WO2013107904A1 (en) | 2012-01-19 | 2013-07-25 | Dsm Ip Assets B.V. | Process to produce alkanoic acid esters in a carbonylation process using lewis acids as acid promotor |
| US9174909B2 (en) * | 2012-02-02 | 2015-11-03 | Wisconsin Alumni Research Foundation | Two-stage, acid-catalyzed conversion of carbohydrates into levulinic acid |
| CA2864911A1 (en) | 2012-02-16 | 2013-08-22 | Karl A. Seck | Biorefinery for conversion of carbohydrates and lignocellulosics via primary hydrolysate cmf to liquid fuels |
| AU2013232364B2 (en) | 2012-03-12 | 2017-10-12 | Georgia-Pacific LLC | Method for producing levulinic acid from lignocellulosic biomass |
| US20150057349A1 (en) * | 2012-03-30 | 2015-02-26 | Nestec S.A. | 4-oxo-2-pentenoic acid and the health of the digestive tract |
| CA2874559A1 (en) * | 2012-07-13 | 2014-01-16 | Dsm Ip Assets B.V. | Process for the production of furfural and levulinic acid from lignocellulosic biomass |
| WO2014037560A1 (en) | 2012-09-10 | 2014-03-13 | Dsm Ip Assets B.V. | Process for the separation of levulinic acid from biomass |
| US9073841B2 (en) * | 2012-11-05 | 2015-07-07 | Segetis, Inc. | Process to prepare levulinic acid |
| BR112015012471B1 (pt) | 2012-11-29 | 2020-05-19 | Segetis Inc | cetais de carbóxi éster , métodos de fabricação e uso dos mesmos. |
| EP2928856B1 (en) * | 2012-12-07 | 2019-09-11 | Georgia-Pacific LLC | Process for the production of a biomass hydrolysate |
| KR20160007533A (ko) | 2013-05-16 | 2016-01-20 | 디에스엠 아이피 어셋츠 비.브이. | 메틸테트라하이드로퓨란으로부터의 폼산의 분리 방법 |
| US20160122278A1 (en) * | 2013-05-22 | 2016-05-05 | Segetis, Inc. | Process to prepare levulinic acid |
| EP3047029B1 (en) * | 2013-09-18 | 2019-10-23 | Georgia-Pacific LLC | Method for producing organic acids and organic acid degradation compounds from biomass |
| EP3046900B1 (en) * | 2013-09-18 | 2019-07-31 | Georgia-Pacific LLC | Method for producing levulinic acid from sludge and lignocellulosic biomass |
| WO2015063033A1 (en) | 2013-11-01 | 2015-05-07 | Dsm Ip Assets B.V. | Process for the separation of levulinic acid |
| EP2924097B1 (en) | 2014-03-26 | 2019-10-16 | Neste Oyj | Method for catalytic conversion of ketoacids and hydrotreatment to hydrocarbons |
| PL3132005T3 (pl) | 2014-03-26 | 2022-03-28 | Neste Oyj | Sposób konwersji termicznej ketokwasów i hydrorafinacji do węglowodorów |
| CN104292193B (zh) * | 2014-09-05 | 2017-01-11 | 中国科学院广州能源研究所 | 一种生物质分级处理后制备糠醛和两步制备乙酰丙酸的方法 |
| CN104292195B (zh) * | 2014-09-05 | 2016-10-12 | 中国科学院广州能源研究所 | 一种生物质分级处理后制备糠醛和调变流量制备乙酰丙酸的方法 |
| CN104292194B (zh) * | 2014-09-05 | 2016-10-12 | 中国科学院广州能源研究所 | 一种生物质分级处理后制备糠醛和快速变温法制备乙酰丙酸的方法 |
| CN104311411B (zh) * | 2014-09-15 | 2015-12-02 | 淮阴师范学院 | 多级酸水解制备乙酰丙酸的方法 |
| EP3050867B1 (en) | 2015-01-30 | 2019-11-13 | Neste Oyj | Method for catalytic conversion of ketoacids via ketoacid dimer intermediate and hydrotreament to hydrocarbons |
| EP3050868B1 (en) | 2015-01-30 | 2019-11-13 | Neste Oyj | Method for catalytic conversion of ketoacids and hydrotreament to hydrocarbons |
| US10150726B2 (en) | 2015-02-13 | 2018-12-11 | Ube Industries, Ltd. | Method for producing levulinic acid ester |
| KR20170118719A (ko) | 2015-02-18 | 2017-10-25 | 디에스엠 아이피 어셋츠 비.브이. | 물 중 수소로 전처리된 루테늄(ru) 촉매를 사용하는 레불린산(la)의 감마-발레로락톤(gvl)으로의 수소화 |
| CN104945446B (zh) * | 2015-05-20 | 2017-11-14 | 中国科学院广州能源研究所 | 一种利用秸秆类生物质制备甲酸酯、乙酸酯、乙酰丙酸酯的方法 |
| EP3115353A1 (en) | 2015-07-10 | 2017-01-11 | GFBiochemicals Ltd. | Process for the isolation of levulinic acid |
| EP3115352A1 (en) | 2015-07-10 | 2017-01-11 | GFBiochemicals Ltd. | Process for the isolation of levulinic acid |
| EP3115351A1 (en) | 2015-07-10 | 2017-01-11 | GFBiochemicals Ltd. | Levulinic acid compositions |
| EP3156389A1 (en) | 2015-10-12 | 2017-04-19 | GFBiochemicals Ltd | Process for the purification of levulinic acid |
| FI127191B (en) | 2015-12-23 | 2018-01-15 | Neste Oyj | Combined production of levulinic acid and furfural from biomass |
| FI127020B (en) | 2015-12-23 | 2017-09-29 | Neste Oyj | Selective method for the conversion of levulinic acid to gamma valerolactone |
| EP3187567B1 (en) | 2015-12-29 | 2021-03-31 | Neste Oyj | Method for producing renewable middle-distillate composition, use of the composition and fuel containing the same |
| EP3187482A1 (en) | 2015-12-29 | 2017-07-05 | Neste Oyj | Renewable hydrocarbons, method for producing the same and use thereof |
| ES2767369T3 (es) | 2015-12-29 | 2020-06-17 | Neste Oyj | Método para producir una mezcla de combustible |
| CN105642204B (zh) * | 2016-02-26 | 2016-10-26 | 河南省科学院能源研究所有限公司 | 一种生物质水解装置 |
| CN106748711B (zh) * | 2016-12-08 | 2019-07-09 | 农业部环境保护科研监测所 | 一种乙酰丙酸的制备方法 |
| CN114315554B (zh) * | 2021-12-23 | 2024-05-28 | 山东理工大学 | 水合物熔盐中甲酸和乙酰丙酸的分离方法 |
| EP4265592A1 (en) | 2022-04-22 | 2023-10-25 | Indian Oil Corporation Limited | Method for producing levulinic acid |
| WO2025093348A1 (en) | 2023-10-30 | 2025-05-08 | Basf Se | Water-emulsifiable isocyanates with improved properties |
| US12227486B1 (en) | 2024-07-29 | 2025-02-18 | Biofine Technology, Llc | Systems and methods for the production of levulinic acid, furfural, and formic acid |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3258481A (en) * | 1962-03-21 | 1966-06-28 | Crown Zellerbach Corp | Preparation of levulinic acid from hexose-containing material |
| US3701789A (en) * | 1970-10-15 | 1972-10-31 | Commw Of Puerto Rico | Process for jointly producing furfural and levulinic acid from bagasse and other lignocellulosic materials |
| US4237226A (en) * | 1979-02-23 | 1980-12-02 | Trustees Of Dartmouth College | Process for pretreating cellulosic substrates and for producing sugar therefrom |
| SE452327B (sv) * | 1979-08-28 | 1987-11-23 | St Lawrence Tech Ltd | Kemisk reaktor for framstellning av modifierad sterkelse och sterkelsederivat i homogen flytande form |
| US4497896A (en) * | 1982-07-19 | 1985-02-05 | St. Lawrence Technologies Limited | Fermentation of glucose with recycle of non-fermented components |
| US4578353A (en) * | 1982-07-19 | 1986-03-25 | St. Lawrence Reactors Limited | Fermentation of glucose with recycle of non-fermented components |
| US4897497A (en) * | 1988-04-26 | 1990-01-30 | Biofine Incorporated | Lignocellulose degradation to furfural and levulinic acid |
-
1995
- 1995-06-07 US US08/475,630 patent/US5608105A/en not_active Expired - Lifetime
-
1996
- 1996-05-17 WO PCT/US1996/007231 patent/WO1996040609A1/en not_active Ceased
- 1996-05-17 EP EP96914708A patent/EP0873294B1/en not_active Expired - Lifetime
- 1996-05-17 CA CA002223600A patent/CA2223600C/en not_active Expired - Lifetime
- 1996-05-17 DE DE69620240T patent/DE69620240T2/de not_active Expired - Lifetime
- 1996-05-17 AU AU57985/96A patent/AU5798596A/en not_active Abandoned
- 1996-06-05 IN IN1230DE1996 patent/IN185298B/en unknown
-
1997
- 1997-12-05 NO NO975727A patent/NO308464B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0873294A4 (en) | 1999-05-26 |
| NO308464B1 (no) | 2000-09-18 |
| NO975727D0 (no) | 1997-12-05 |
| CA2223600A1 (en) | 1996-12-19 |
| NO975727L (no) | 1998-02-04 |
| AU5798596A (en) | 1996-12-30 |
| WO1996040609A1 (en) | 1996-12-19 |
| DE69620240D1 (de) | 2002-05-02 |
| EP0873294A1 (en) | 1998-10-28 |
| IN185298B (en0) | 2000-12-23 |
| US5608105A (en) | 1997-03-04 |
| EP0873294B1 (en) | 2002-03-27 |
| DE69620240T2 (de) | 2002-11-14 |
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