AU2008318001A1 - Continuous method for the heterogenically catalyzed esterification of fatty acids - Google Patents
Continuous method for the heterogenically catalyzed esterification of fatty acids Download PDFInfo
- Publication number
- AU2008318001A1 AU2008318001A1 AU2008318001A AU2008318001A AU2008318001A1 AU 2008318001 A1 AU2008318001 A1 AU 2008318001A1 AU 2008318001 A AU2008318001 A AU 2008318001A AU 2008318001 A AU2008318001 A AU 2008318001A AU 2008318001 A1 AU2008318001 A1 AU 2008318001A1
- Authority
- AU
- Australia
- Prior art keywords
- process according
- catalyst
- fatty acids
- free fatty
- alcohol
- 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.)
- Abandoned
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 27
- 229930195729 fatty acid Natural products 0.000 title claims description 27
- 239000000194 fatty acid Substances 0.000 title claims description 27
- 238000005886 esterification reaction Methods 0.000 title claims description 20
- 150000004665 fatty acids Chemical class 0.000 title claims description 12
- 230000032050 esterification Effects 0.000 title description 16
- 238000011437 continuous method Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 86
- 239000003054 catalyst Substances 0.000 claims description 63
- 235000021588 free fatty acids Nutrition 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 239000007858 starting material Substances 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 230000002378 acidificating effect Effects 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 238000005809 transesterification reaction Methods 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 9
- 239000003225 biodiesel Substances 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000003925 fat Substances 0.000 description 12
- 235000019197 fats Nutrition 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- -1 C 5 alcohols Chemical class 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000221089 Jatropha Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007052065A DE102007052065A1 (de) | 2007-10-30 | 2007-10-30 | Kontinuierliches Verfahren zur heterogen katalysierten Veresterung von Fettsäuren |
| DE102007052065.6 | 2007-10-30 | ||
| PCT/EP2008/008763 WO2009056231A1 (de) | 2007-10-30 | 2008-10-16 | Kontinuierliches verfahren zur heterogen katalysierten veresterung von fettsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2008318001A1 true AU2008318001A1 (en) | 2009-05-07 |
Family
ID=40292442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008318001A Abandoned AU2008318001A1 (en) | 2007-10-30 | 2008-10-16 | Continuous method for the heterogenically catalyzed esterification of fatty acids |
Country Status (22)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2522712A1 (en) * | 2011-05-13 | 2012-11-14 | Cognis IP Management GmbH | Process for obtaining fatty acid lower alkyl esters from unrefined fats and oils |
| US8957242B2 (en) | 2013-03-15 | 2015-02-17 | Renewable Energy Group, Inc. | Dual catalyst esterification |
| ES2823649T3 (es) * | 2013-06-19 | 2021-05-07 | Argent Energy Uk Ltd | Proceso para la producción de biodiésel y productos relacionados |
| FR3015515B1 (fr) | 2013-12-19 | 2016-02-05 | IFP Energies Nouvelles | Procede de pretraitement d'huiles vegetales par catalyse heterogene de l'esterification des acides gras |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB384715A (en) * | 1931-08-31 | 1932-12-15 | Ig Farbenindustrie Ag | Apparatus for carrying out the manufacture and production of neutral products from oiats |
| FR1593995A (cg-RX-API-DMAC7.html) | 1968-12-04 | 1970-06-01 | Beyl J | |
| JPS6042495A (ja) * | 1983-08-17 | 1985-03-06 | 日清製油株式会社 | 油脂脱臭留出物のメチルエステル化法 |
| DE3501761A1 (de) | 1985-01-21 | 1986-07-24 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur vorveresterung freier fettsaeuren in rohfetten und/oder -oelen |
| DE19600025C2 (de) | 1996-01-03 | 1998-12-03 | Henkel Kgaa | Verfahren zur Herstellung von Fettstoffen |
| JP4156486B2 (ja) * | 2003-10-14 | 2008-09-24 | 花王株式会社 | 脂肪酸エステルの製造法 |
| ITMI20060082A1 (it) | 2006-01-19 | 2007-07-20 | Maurizio Germani | Processo per la preparazione di biodiesel |
| ITMI20060279A1 (it) | 2006-02-15 | 2007-08-16 | Aser S R L | Procedimento per deacidificare oli e-o grassi |
| CN1865401A (zh) * | 2006-06-19 | 2006-11-22 | 菏泽华瑞油脂有限责任公司 | 高酸价棉籽油制取生物柴油的方法 |
| CN101016473B (zh) * | 2007-03-02 | 2012-04-18 | 安徽省粮油科学研究所 | 劣质油生产生物燃料油的方法 |
| CN101058734B (zh) * | 2007-05-31 | 2010-12-01 | 张付舜 | 工业化微波合成生物柴油的装置及其方法 |
-
2007
- 2007-10-30 DE DE102007052065A patent/DE102007052065A1/de not_active Withdrawn
-
2008
- 2008-10-14 UY UY31390A patent/UY31390A1/es not_active Application Discontinuation
- 2008-10-16 WO PCT/EP2008/008763 patent/WO2009056231A1/de not_active Ceased
- 2008-10-16 AU AU2008318001A patent/AU2008318001A1/en not_active Abandoned
- 2008-10-16 CN CN200880113695.7A patent/CN101842471B/zh not_active Expired - Fee Related
- 2008-10-16 NZ NZ584970A patent/NZ584970A/en not_active IP Right Cessation
- 2008-10-16 EA EA201000582A patent/EA018797B1/ru not_active IP Right Cessation
- 2008-10-16 BR BRPI0819144A patent/BRPI0819144A8/pt not_active IP Right Cessation
- 2008-10-16 EP EP08844944A patent/EP2205708A1/de not_active Withdrawn
- 2008-10-16 US US12/738,115 patent/US8299282B2/en not_active Expired - Fee Related
- 2008-10-16 CA CA2703813A patent/CA2703813A1/en not_active Abandoned
- 2008-10-16 MX MX2010004519A patent/MX2010004519A/es active IP Right Grant
- 2008-10-16 PA PA20088799301A patent/PA8799301A1/es unknown
- 2008-10-17 PE PE2008001787A patent/PE20090934A1/es not_active Application Discontinuation
- 2008-10-29 AR ARP080104719A patent/AR071058A1/es not_active Application Discontinuation
-
2010
- 2010-04-08 IL IL204938A patent/IL204938A/en not_active IP Right Cessation
- 2010-04-27 NI NI201000073A patent/NI201000073A/es unknown
- 2010-04-28 CR CR11400A patent/CR11400A/es not_active Application Discontinuation
- 2010-04-28 ZA ZA2010/02942A patent/ZA201002942B/en unknown
- 2010-04-28 HN HN2010000893A patent/HN2010000893A/es unknown
- 2010-04-28 CO CO10050348A patent/CO6270372A2/es active IP Right Grant
- 2010-04-28 SV SV2010003551A patent/SV2010003551A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PA8799301A1 (es) | 2009-06-23 |
| CR11400A (es) | 2010-11-02 |
| EA018797B1 (ru) | 2013-10-30 |
| EP2205708A1 (de) | 2010-07-14 |
| NZ584970A (en) | 2012-06-29 |
| IL204938A0 (en) | 2010-11-30 |
| HN2010000893A (es) | 2013-06-24 |
| ZA201002942B (en) | 2011-07-27 |
| EA201000582A1 (ru) | 2010-10-29 |
| CN101842471B (zh) | 2014-12-10 |
| PE20090934A1 (es) | 2009-07-24 |
| CN101842471A (zh) | 2010-09-22 |
| SV2010003551A (es) | 2011-08-11 |
| US20100249442A1 (en) | 2010-09-30 |
| CA2703813A1 (en) | 2009-05-07 |
| AR071058A1 (es) | 2010-05-26 |
| UY31390A1 (es) | 2009-05-29 |
| BRPI0819144A2 (cg-RX-API-DMAC7.html) | 2009-05-07 |
| IL204938A (en) | 2013-12-31 |
| CO6270372A2 (es) | 2011-04-20 |
| DE102007052065A1 (de) | 2009-05-07 |
| NI201000073A (es) | 2010-09-23 |
| BRPI0819144A8 (pt) | 2016-04-26 |
| MX2010004519A (es) | 2010-05-14 |
| WO2009056231A1 (de) | 2009-05-07 |
| US8299282B2 (en) | 2012-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: BAYER INTELLECTUAL PROPERTY GMBH Free format text: FORMER APPLICANT(S): BAYER TECHNOLOGY SERVICES GMBH |
|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |