CN1041822C - 连续生产高级脂肪酸的c1－4烷基酯的方法 - Google Patents
连续生产高级脂肪酸的c1－4烷基酯的方法 Download PDFInfo
- Publication number
- CN1041822C CN1041822C CN93103664A CN93103664A CN1041822C CN 1041822 C CN1041822 C CN 1041822C CN 93103664 A CN93103664 A CN 93103664A CN 93103664 A CN93103664 A CN 93103664A CN 1041822 C CN1041822 C CN 1041822C
- Authority
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- China
- Prior art keywords
- reaction mixture
- transesterification
- catalyst
- reactor
- separator
- 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
- 238000000034 method Methods 0.000 title claims abstract description 38
- 239000000194 fatty acid Substances 0.000 title claims abstract description 8
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 7
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 7
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 6
- 150000002148 esters Chemical class 0.000 title claims description 8
- 238000010924 continuous production Methods 0.000 title description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 80
- 235000011187 glycerol Nutrition 0.000 claims abstract description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 33
- 239000011541 reaction mixture Substances 0.000 claims abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims abstract description 12
- 239000000344 soap Substances 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 10
- 238000000605 extraction Methods 0.000 claims abstract description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 150000001298 alcohols Chemical class 0.000 claims abstract 4
- 230000003197 catalytic effect Effects 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 6
- 230000003068 static effect Effects 0.000 claims description 3
- 235000021588 free fatty acids Nutrition 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 3
- 239000007853 buffer solution Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 9
- 239000011536 extraction buffer Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 238000002156 mixing Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- -1 fatty acid ester Chemical class 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 206010020852 Hypertonia Diseases 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4209779A DE4209779C1 (enExample) | 1992-03-26 | 1992-03-26 | |
| DEP4209779.7 | 1992-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1076687A CN1076687A (zh) | 1993-09-29 |
| CN1041822C true CN1041822C (zh) | 1999-01-27 |
Family
ID=6455033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93103664A Expired - Lifetime CN1041822C (zh) | 1992-03-26 | 1993-03-26 | 连续生产高级脂肪酸的c1－4烷基酯的方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5354878A (enExample) |
| EP (1) | EP0562504B1 (enExample) |
| CN (1) | CN1041822C (enExample) |
| AT (1) | ATE129695T1 (enExample) |
| BR (1) | BR9301318A (enExample) |
| CA (1) | CA2092470C (enExample) |
| DE (2) | DE4209779C1 (enExample) |
| DK (1) | DK0562504T3 (enExample) |
| ES (1) | ES2081152T3 (enExample) |
| MY (1) | MY115277A (enExample) |
| PL (1) | PL171878B1 (enExample) |
Families Citing this family (106)
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| FR2748490B1 (fr) * | 1996-05-07 | 1998-06-19 | Inst Francais Du Petrole | Procede de fabrication d'esters ethyliques |
| DE19702989A1 (de) * | 1997-01-28 | 1998-07-30 | Clariant Gmbh | Umweltfreundlicher Dieseltreibstoff |
| DE19742097C1 (de) * | 1997-09-24 | 1998-12-10 | Henkel Kgaa | Verfahren zur Gewinnung von hellfarbigen Fettsäureniedrigalkylestern mit vermindertem Gehalt an freiem und gebundenem Glycerin |
| DE19925871A1 (de) | 1999-06-07 | 2000-12-21 | At Agrar Technik Gmbh | Verfahren zur Herstellung von Fettsäureestern einwertiger Alkylalkohole und deren Verwendung |
| DE10132842C1 (de) * | 2001-07-06 | 2002-11-28 | Siegfried Peter | Verfahren zur Umesterung von Fett und/oder Öl mittels Alkoholyse |
| DE10138822A1 (de) * | 2001-08-14 | 2003-03-06 | Bruno Berger | Umesterungsvorrichtung mit Schrägrohrreaktor |
| US20050081435A1 (en) * | 2001-09-09 | 2005-04-21 | Lastella Joseph P. | Continuous flow method and apparatus for making biodiesel fuel |
| HU0104786D0 (en) | 2001-11-08 | 2002-01-28 | Kovacs Andras Dr | Method for producing of vegetable oil-methyl-esther |
| AU2002347198B2 (en) * | 2001-12-13 | 2008-04-17 | Jott Australia Pty Ltd | Process for production of fatty acid esters |
| AUPR946201A0 (en) * | 2001-12-13 | 2002-01-24 | Jott Australia Pty. Ltd. | Process for production of fatty acid esters |
| ES2201894B2 (es) * | 2002-01-18 | 2005-03-01 | Industrial Management, S.A | Procedimiento para producir combustibles biodiesel con propiedades mejoradas a baja temperatura. |
| KR100556337B1 (ko) * | 2002-02-05 | 2006-03-03 | 주식회사 가야에너지 | 단일단계 연속공정을 통한 고순도 지방산 알킬에스테르의제조방법 |
| RU2475520C2 (ru) | 2002-11-13 | 2013-02-20 | Лангсесс Дойчланд ГмбХ | Способ повышения стабильности дизельного биотоплива при хранении |
| TWI324592B (en) * | 2002-11-28 | 2010-05-11 | Sulzer Chemtech Ag | A method for the esterification of a fatty acid |
| US9725397B2 (en) | 2003-01-27 | 2017-08-08 | REG Seneca, LLC | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| US8088183B2 (en) | 2003-01-27 | 2012-01-03 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| US7871448B2 (en) * | 2003-01-27 | 2011-01-18 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| US7806945B2 (en) * | 2003-01-27 | 2010-10-05 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| KR100566106B1 (ko) * | 2003-03-28 | 2006-03-30 | 한국에너지기술연구원 | 바이오디젤유의 제조방법 |
| US6822105B1 (en) * | 2003-08-12 | 2004-11-23 | Stepan Company | Method of making alkyl esters using glycerin |
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| JP4567961B2 (ja) * | 2003-11-27 | 2010-10-27 | 株式会社レボインターナショナル | 油脂からのデイーゼル燃料油製造プロセス |
| MD2958C2 (ro) * | 2004-04-22 | 2006-11-30 | Валериу ДОМИНАС | Instalaţie pentru obţinerea combustibilului biodiesel din uleiuri vegetale |
| US7619104B2 (en) * | 2005-04-04 | 2009-11-17 | Renewable Products Development Laboratories, Inc. | Process for producing biodiesel or fatty acid esters from multiple triglyceride feedstocks |
| BRPI0503631B1 (pt) * | 2005-08-19 | 2015-07-21 | Petróleo Brasileiro S.A. - Petrobras | Processo para a produção de biodiesel |
| US20070048848A1 (en) * | 2005-08-25 | 2007-03-01 | Sunsource Industries | Method, apparatus and system for biodiesel production from algae |
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| US20150232885A1 (en) | 2012-08-13 | 2015-08-20 | Hyperthermics Holding As | Production of biokerosene with hyperthermophilic organisms |
| US9090862B2 (en) | 2012-12-21 | 2015-07-28 | Ductor Oy | System and method for processing biological material |
| US10098371B2 (en) | 2013-01-28 | 2018-10-16 | Solazyme Roquette Nutritionals, LLC | Microalgal flour |
| US9249252B2 (en) | 2013-04-26 | 2016-02-02 | Solazyme, Inc. | Low polyunsaturated fatty acid oils and uses thereof |
| WO2014201001A1 (en) | 2013-06-11 | 2014-12-18 | Renewable Energy Group, Inc. | Production of biodiesel and products obtained therefrom |
| FR3009619B1 (fr) | 2013-08-07 | 2017-12-29 | Roquette Freres | Compositions de biomasse de microalgues riches en proteines de qualite sensorielle optimisee |
| US9328054B1 (en) | 2013-09-27 | 2016-05-03 | Travis Danner | Method of alcoholisis of fatty acids and fatty acid gyicerides |
| EP3052636A2 (en) | 2013-10-04 | 2016-08-10 | Solazyme, Inc. | Tailored oils |
| WO2015149026A1 (en) | 2014-03-28 | 2015-10-01 | Solazyme, Inc. | Lauric ester compositions |
| ES2764273T3 (es) | 2014-07-10 | 2020-06-02 | Corbion Biotech Inc | Nuevos genes de cetoacil ACP sintasa y uso de los mismos |
| EP4071226A1 (en) | 2021-04-08 | 2022-10-12 | AT Agrar-Technik Int. GmbH | Process for producing fatty acid alkyl esters |
| KR20250044700A (ko) | 2022-07-21 | 2025-04-01 | 바스프 에스이 | 바이오디젤 생산을 위한 혼합 알콕시화물 촉매 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0198243A2 (de) * | 1985-04-06 | 1986-10-22 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von Carbonsäurealkylestern, insbesondere Fettsäurealkylestern |
| EP0391485A1 (en) * | 1989-04-05 | 1990-10-10 | Unilever N.V. | Process for producing fatty-acid lower-alkyl monoesters |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA517818A (en) * | 1955-10-25 | H. Kuhrt Noel | Process for substantially complete conversion of fatty material to partial ester | |
| JPS5665097A (en) * | 1979-05-30 | 1981-06-02 | Lion Corp | Manufacture of fatty acid lower alcohol ester |
| DE3444893A1 (de) * | 1984-12-08 | 1986-06-12 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von fettsaeuremethylestern |
| DE3727081A1 (de) * | 1987-08-14 | 1989-02-23 | Merck Patent Gmbh | Beschichtungen |
| DE3932514A1 (de) * | 1989-09-29 | 1991-04-18 | Henkel Kgaa | Kontinuierliches verfahren zum herstellen niederer alkylester |
-
1992
- 1992-03-26 DE DE4209779A patent/DE4209779C1/de not_active Expired - Fee Related
-
1993
- 1993-02-18 MY MYPI93000275A patent/MY115277A/en unknown
- 1993-03-22 EP EP93104625A patent/EP0562504B1/de not_active Expired - Lifetime
- 1993-03-22 DE DE59300838T patent/DE59300838D1/de not_active Expired - Lifetime
- 1993-03-22 DK DK93104625.4T patent/DK0562504T3/da active
- 1993-03-22 ES ES93104625T patent/ES2081152T3/es not_active Expired - Lifetime
- 1993-03-22 AT AT93104625T patent/ATE129695T1/de active
- 1993-03-24 PL PL93298214A patent/PL171878B1/pl unknown
- 1993-03-25 CA CA002092470A patent/CA2092470C/en not_active Expired - Lifetime
- 1993-03-25 BR BR9301318A patent/BR9301318A/pt not_active IP Right Cessation
- 1993-03-26 CN CN93103664A patent/CN1041822C/zh not_active Expired - Lifetime
- 1993-03-26 US US08/037,224 patent/US5354878A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0198243A2 (de) * | 1985-04-06 | 1986-10-22 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von Carbonsäurealkylestern, insbesondere Fettsäurealkylestern |
| EP0391485A1 (en) * | 1989-04-05 | 1990-10-10 | Unilever N.V. | Process for producing fatty-acid lower-alkyl monoesters |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4209779C1 (enExample) | 1993-07-15 |
| EP0562504A3 (en) | 1993-10-27 |
| ES2081152T3 (es) | 1996-02-16 |
| CN1076687A (zh) | 1993-09-29 |
| ATE129695T1 (de) | 1995-11-15 |
| PL298214A1 (en) | 1994-01-24 |
| MY115277A (en) | 2003-05-31 |
| DK0562504T3 (da) | 1996-03-04 |
| EP0562504B1 (de) | 1995-11-02 |
| PL171878B1 (pl) | 1997-06-30 |
| BR9301318A (pt) | 1993-09-28 |
| EP0562504A2 (de) | 1993-09-29 |
| DE59300838D1 (de) | 1995-12-07 |
| CA2092470C (en) | 1999-01-26 |
| US5354878A (en) | 1994-10-11 |
| CA2092470A1 (en) | 1993-09-27 |
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