JP2007009017A - 脂肪酸アルキルエステルの製造方法 - Google Patents
脂肪酸アルキルエステルの製造方法 Download PDFInfo
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- JP2007009017A JP2007009017A JP2005190005A JP2005190005A JP2007009017A JP 2007009017 A JP2007009017 A JP 2007009017A JP 2005190005 A JP2005190005 A JP 2005190005A JP 2005190005 A JP2005190005 A JP 2005190005A JP 2007009017 A JP2007009017 A JP 2007009017A
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- fatty acid
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- 239000000194 fatty acid Substances 0.000 title claims abstract description 180
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 179
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 179
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 44
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 119
- 238000000034 method Methods 0.000 claims abstract description 50
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000003377 acid catalyst Substances 0.000 claims abstract description 20
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 5
- 235000011187 glycerol Nutrition 0.000 claims description 19
- 238000005191 phase separation Methods 0.000 claims description 15
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 7
- 125000003158 alcohol group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 52
- 239000003921 oil Substances 0.000 abstract description 31
- 230000008569 process Effects 0.000 abstract description 23
- 239000003925 fat Substances 0.000 abstract description 22
- 239000003054 catalyst Substances 0.000 abstract description 18
- -1 fatty acid triglycerides Chemical class 0.000 abstract description 17
- 239000002994 raw material Substances 0.000 abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 235000019441 ethanol Nutrition 0.000 description 30
- 235000019198 oils Nutrition 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 25
- 238000005886 esterification reaction Methods 0.000 description 18
- 238000006460 hydrolysis reaction Methods 0.000 description 17
- 239000012071 phase Substances 0.000 description 13
- 230000003197 catalytic effect Effects 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- 239000003513 alkali Substances 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 238000010586 diagram Methods 0.000 description 7
- 238000005809 transesterification reaction Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000003225 biodiesel Substances 0.000 description 5
- 235000021588 free fatty acids Nutrition 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 102000004882 Lipase Human genes 0.000 description 3
- 108090001060 Lipase Proteins 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000013618 particulate matter Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000010828 animal waste Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008162 cooking oil Substances 0.000 description 1
- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- RECVMTHOQWMYFX-UHFFFAOYSA-N oxygen(1+) dihydride Chemical compound [OH2+] RECVMTHOQWMYFX-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052815 sulfur oxide Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Fats And Perfumes (AREA)
Abstract
脂肪酸アルキルエステルの無触媒・二段階製造方法の反応速度を高め、脂肪酸アルキルエステルの製造効率の向上を達成すること。
【解決手段】
原料油脂に含まれる脂肪酸トリグリセリドを所定の温度・圧力条件で加水分解して脂肪酸とグリセリンを得る第1工程P1と、該第1工程P1の生成物にアルコールを添加し、所定の温度・圧力条件で前記生成物に含まれる脂肪酸を脂肪酸アルキルエステルに変換する第2工程P2と、を少なくとも行なって脂肪酸アルキルエステルを製造する方法において、前記第1工程P1の生成物中の脂肪酸の一部を該第1工程P1に返送し、酸触媒として使用する。
【選択図】 図4
Description
P2 第2工程
Claims (6)
- 原料油脂に含まれる脂肪酸トリグリセリドを所定の温度・圧力条件で加水分解して脂肪酸とグリセリンを得る第1工程と、該第1工程の生成物にアルコールを添加し、所定の温度・圧力条件で前記生成物に含まれる脂肪酸を脂肪酸アルキルエステルに変換する第2工程と、を少なくとも行なって脂肪酸アルキルエステルを製造する方法において、
前記第1工程の生成物中の脂肪酸の一部を該第1工程に返送して使用することを特徴とする脂肪酸アルキルエステルの製造方法。 - 前記第1工程の生成物中の全脂肪酸量の3〜70重量%の脂肪酸を返送することを特徴とする請求項1記載の脂肪酸アルキルエステルの製造方法。
- 前記第1工程後に、生成物の相分離工程を行なうことによってグリセリンを除去することを特徴とする請求項1記載の脂肪酸アルキルエステルの製造方法。
- 前記相分離工程を、前記第1工程の温度・圧力条件を維持して行うことを特徴とする請求項3記載の脂肪酸アルキルエステルの製造方法。
- 前記第2工程において、該工程で添加するアルコールの脂肪酸に対する体積比をより小さくすることにより、該脂肪酸の酸触媒効果を高めることを特徴とする請求項1記載の脂肪酸アルキルエステルの製造方法。
- 前記第2工程において、圧力を低下させて前記アルコールの一部を気化することによって、アルコールに対する脂肪酸の濃度を相対的に増加させることを特徴とする請求項5記載の脂肪酸アルキルエステルの製造方法。
Priority Applications (1)
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JP2005190005A JP5058459B2 (ja) | 2005-06-29 | 2005-06-29 | 脂肪酸アルキルエステルの製造方法 |
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JP2005190005A JP5058459B2 (ja) | 2005-06-29 | 2005-06-29 | 脂肪酸アルキルエステルの製造方法 |
Publications (2)
Publication Number | Publication Date |
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JP2007009017A true JP2007009017A (ja) | 2007-01-18 |
JP5058459B2 JP5058459B2 (ja) | 2012-10-24 |
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JP2005190005A Expired - Fee Related JP5058459B2 (ja) | 2005-06-29 | 2005-06-29 | 脂肪酸アルキルエステルの製造方法 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100830645B1 (ko) * | 2006-08-31 | 2008-05-20 | 발레오전장시스템스코리아 주식회사 | 스톱핑 노이즈가 예방되는 스타트모터 |
JP2011174060A (ja) * | 2010-01-29 | 2011-09-08 | Shiro Saka | 脂肪酸アルキルエステルの製造方法および油脂類の処理方法 |
WO2011108270A1 (ja) * | 2010-03-03 | 2011-09-09 | 独立行政法人農業・食品産業技術総合研究機構 | 脂肪酸メチルエステル製造方法及びシステム |
WO2015012538A1 (ko) * | 2013-07-22 | 2015-01-29 | 에스케이케미칼 주식회사 | 지방을 이용한 지방산알킬에스테르의 제조방법 |
JP2016505355A (ja) * | 2012-11-15 | 2016-02-25 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフトBayer MaterialScience AG | サファイア窓を備える相分離又は抽出のための装置及びその使用 |
ITUA20164114A1 (it) * | 2016-06-06 | 2017-12-06 | Novamont Spa | Processo migliorato di idrolisi di trigliceridi di acidi dicarbossilici. |
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US5349075A (en) * | 1989-12-22 | 1994-09-20 | Unilever Patent Holdings B.V. | Continous esterification of carboxylic and fatty acids in the absense of a catalyst |
JP2004026738A (ja) * | 2002-06-27 | 2004-01-29 | New Japan Chem Co Ltd | 脂肪酸エステルの製造方法 |
WO2004108873A1 (ja) * | 2003-06-06 | 2004-12-16 | Asahi Kasei Kabushiki Kaisha | 脂肪酸エステル組成物の製造方法 |
WO2005005584A1 (en) * | 2003-07-10 | 2005-01-20 | Akzo Nobel N.V. | Process for preparing purified fatty acids |
-
2005
- 2005-06-29 JP JP2005190005A patent/JP5058459B2/ja not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US5349075A (en) * | 1989-12-22 | 1994-09-20 | Unilever Patent Holdings B.V. | Continous esterification of carboxylic and fatty acids in the absense of a catalyst |
JP2004026738A (ja) * | 2002-06-27 | 2004-01-29 | New Japan Chem Co Ltd | 脂肪酸エステルの製造方法 |
WO2004108873A1 (ja) * | 2003-06-06 | 2004-12-16 | Asahi Kasei Kabushiki Kaisha | 脂肪酸エステル組成物の製造方法 |
WO2005005584A1 (en) * | 2003-07-10 | 2005-01-20 | Akzo Nobel N.V. | Process for preparing purified fatty acids |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100830645B1 (ko) * | 2006-08-31 | 2008-05-20 | 발레오전장시스템스코리아 주식회사 | 스톱핑 노이즈가 예방되는 스타트모터 |
JP2011174060A (ja) * | 2010-01-29 | 2011-09-08 | Shiro Saka | 脂肪酸アルキルエステルの製造方法および油脂類の処理方法 |
WO2011108270A1 (ja) * | 2010-03-03 | 2011-09-09 | 独立行政法人農業・食品産業技術総合研究機構 | 脂肪酸メチルエステル製造方法及びシステム |
JP2016505355A (ja) * | 2012-11-15 | 2016-02-25 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフトBayer MaterialScience AG | サファイア窓を備える相分離又は抽出のための装置及びその使用 |
CN105555920A (zh) * | 2013-07-22 | 2016-05-04 | Sk化学株式会社 | 一种使用脂肪制备脂肪酸烷基酯的方法 |
KR20150011306A (ko) * | 2013-07-22 | 2015-01-30 | 에스케이케미칼주식회사 | 지방을 이용한 지방산알킬에스테르의 제조방법 |
WO2015012538A1 (ko) * | 2013-07-22 | 2015-01-29 | 에스케이케미칼 주식회사 | 지방을 이용한 지방산알킬에스테르의 제조방법 |
EP3026096A4 (en) * | 2013-07-22 | 2017-03-01 | SK Chemicals Co., Ltd. | Method for preparing fatty acid alkyl ester using fat |
US9938487B2 (en) | 2013-07-22 | 2018-04-10 | Sk Chemicals Co., Ltd. | Method for preparing fatty acid alkyl ester using fat |
TWI628275B (zh) * | 2013-07-22 | 2018-07-01 | Sk化學股份有限公司 | 使用脂肪製備脂肪酸烷酯之方法 |
CN105555920B (zh) * | 2013-07-22 | 2019-01-11 | Sk化学株式会社 | 一种使用脂肪制备脂肪酸烷基酯的方法 |
KR102327852B1 (ko) * | 2013-07-22 | 2021-11-18 | 에스케이에코프라임 주식회사 | 지방을 이용한 지방산알킬에스테르의 제조방법 |
ITUA20164114A1 (it) * | 2016-06-06 | 2017-12-06 | Novamont Spa | Processo migliorato di idrolisi di trigliceridi di acidi dicarbossilici. |
WO2017211764A1 (en) * | 2016-06-06 | 2017-12-14 | Novamont S.P.A. | Improved process for the hydrolysis of dicarboxylic acid triglycerides. |
US11028036B2 (en) | 2016-06-06 | 2021-06-08 | Novamont S.P.A. | Process for the hydrolysis of dicarboxylic acid triglycerides |
Also Published As
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