JP5380523B2 - 脂肪酸を用いた脂肪酸アルキルエステルの製造方法 - Google Patents
脂肪酸を用いた脂肪酸アルキルエステルの製造方法 Download PDFInfo
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- JP5380523B2 JP5380523B2 JP2011502839A JP2011502839A JP5380523B2 JP 5380523 B2 JP5380523 B2 JP 5380523B2 JP 2011502839 A JP2011502839 A JP 2011502839A JP 2011502839 A JP2011502839 A JP 2011502839A JP 5380523 B2 JP5380523 B2 JP 5380523B2
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- Prior art keywords
- fatty acid
- reaction
- alcohol
- acid alkyl
- alkyl ester
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- 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.)
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- 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
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
-
- 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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- 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)
Description
エステル化反応は、図3に示す反応器を用いて2段階によって行った。まず、1次反応器を温度300℃、圧力3barに調節し、粗パーム油を蒸留して得た脂肪酸蒸留物1kg、及び、コバルトアセタート0.2gを含みたメタノール1kgを、反応器に連続して投入して1時間かけて反応させた。次に、1次反応器の反応物が連続して2次反応器に取り込まれた。2次反応器の温度は1次反応器と同じ温度に維持し、圧力を常圧まで下げて1時間かけて反応させた。2次反応器における反応のためにメタノール2kg(1次流入量の2倍)を3等分して、それぞれの隔室44a、44b、44cに連続して投入した。前記方法による脂肪酸メチルエステルへの転換率は99.7%(全酸価0.4未満)であった。反応終結時間は触媒を投入しなかった場合に比べて50%に短縮された。
エステル化反応は回分式反応器を用いて1段階によって行った。まず、反応器に脂肪酸蒸留物1kg、及び、テトラブチルチタナート0.8gを含みたメタノール0.5kgを、反応器に投入した。反応器を温度300℃、圧力3barに調節した後、メタノール1kgを連続して反応器に投入して1.5時間かけて反応させた。前記方法により得られた脂肪酸メチルエステルの転換率は99.8%であった。反応終結時間は合計1.5時間であり、触媒を投入しなかったときに比べて反応時間が50%減少された。
本発明に係る脂肪酸アルキルエステルの製造方法は、小規模装置だけではなく、工業的な規模の装置にも使用可能である。特に、本発明に係る脂肪酸メチルエステルは、別途の追加工程を経ることなく直ちにバイオディーゼル油として利用可能である。
Claims (4)
- 金属触媒の存在下で脂肪酸原料とアルコールをエステル化反応させる段階を含むバイオディーゼル燃料用脂肪酸アルキルエステルの製造方法であって、
前記エステル化反応は200〜350℃の反応温度及び常圧〜10barの反応圧力の条件下で行われ、
前記金属触媒は、触媒中の金属成分が脂肪酸原料に対して重量基準で30〜200ppmとなる量にて使用され、
前記金属触媒は、コバルトアセタート、マンガンアセタート、亜鉛アセタート、鉄アセタート、テトラブチルチタナート及びこれらの混合物よりなる群から選ばれるものである脂肪酸アルキルエステルの製造方法。 - 前記金属触媒は、アルコール溶液状で前記エステル化反応に投入される請求項1に記載の脂肪酸アルキルエステルの製造方法。
- 前記エステル化反応は、300〜350℃の反応温度及び常圧〜10barの反応圧力の条件下で行われるものである請求項1または2に記載の脂肪酸アルキルエステルの製造方法。
- 前記金属触媒は、コバルトアセタート、マンガンアセタート、鉄アセタート及びこれらの混合物よりなる群から選ばれるものである請求項1〜3のいずれかに記載の脂肪酸アルキルエステルの製造方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/KR2008/001831 WO2009123369A1 (en) | 2008-04-01 | 2008-04-01 | Method for preparing fatty acid alkyl ester using fatty acid |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011516466A JP2011516466A (ja) | 2011-05-26 |
JP5380523B2 true JP5380523B2 (ja) | 2014-01-08 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011502839A Active JP5380523B2 (ja) | 2008-04-01 | 2008-04-01 | 脂肪酸を用いた脂肪酸アルキルエステルの製造方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US8530684B2 (ja) |
EP (1) | EP2257518B1 (ja) |
JP (1) | JP5380523B2 (ja) |
CN (2) | CN105176696A (ja) |
ES (1) | ES2575099T3 (ja) |
HK (1) | HK1213283A1 (ja) |
MX (1) | MX2010010879A (ja) |
PL (1) | PL2257518T3 (ja) |
WO (1) | WO2009123369A1 (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101554607B1 (ko) | 2008-11-07 | 2015-09-22 | 에스케이케미칼주식회사 | 지방산을 이용한 지방산알킬에스테르의 제조방법 및 장치 |
US8455412B2 (en) | 2010-08-31 | 2013-06-04 | Biosynthetic Technologies, Llc | Acetic acid-capped estolide base oils and methods of making the same |
CN102634382A (zh) * | 2012-03-22 | 2012-08-15 | 东营职业学院 | 一种超声空化金属弱酸盐催化地沟油制备生物柴油的方法 |
GB201210655D0 (en) * | 2012-06-15 | 2012-08-01 | Davy Process Techn Ltd | Process |
EP2861703B1 (en) | 2012-06-18 | 2017-02-15 | Biosynthetic Technologies, LLC | Processes of preparing estolide compounds that include removing sulfonate residues |
KR102327852B1 (ko) * | 2013-07-22 | 2021-11-18 | 에스케이에코프라임 주식회사 | 지방을 이용한 지방산알킬에스테르의 제조방법 |
WO2015045969A1 (ja) * | 2013-09-25 | 2015-04-02 | 株式会社Adeka | エステル化合物の製造方法 |
ES2585706B1 (es) * | 2016-04-21 | 2017-08-14 | Soluciones Industriales Extremeñas Sll | Procedimiento mejorado para el refino y esterificación continua de cualquier material graso de origen vegetal o animal, especialmente diseñado para subproductos animales de categoría 1 y 2 |
WO2018144385A1 (en) * | 2017-01-31 | 2018-08-09 | Sunovion Pharmaceuticals Inc. | Enamide process |
US10988708B2 (en) | 2019-02-25 | 2021-04-27 | Inventure Renewables, Inc. | Systems and methods for fatty acid alkyl ester production with recycling |
CN111892501A (zh) * | 2020-07-15 | 2020-11-06 | 江西盛伟科技股份有限公司 | 一种6-羟基己酸甲酯的制备方法 |
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DE2943549A1 (de) * | 1979-10-27 | 1981-05-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von urethanen und ihre verwendung zur herstellung von isocyanaten |
DE3319590A1 (de) * | 1983-05-30 | 1984-12-06 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von fettsaeureestern kurzkettiger aliphatischer alkohole aus freie fettsaeuren enthaltenden fetten und/oder oelen |
DE3444893A1 (de) | 1984-12-08 | 1986-06-12 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von fettsaeuremethylestern |
AT399336B (de) * | 1993-07-14 | 1995-04-25 | Martin Mag Dr Mittelbach | Verfahren zur herstellung von fettsäurealkylestern |
DE19638460A1 (de) * | 1996-09-19 | 1998-03-26 | Peter Siegfried | Verfahren zur Herstellung von Fettsäureestern |
JP4929555B2 (ja) * | 2000-10-16 | 2012-05-09 | 日油株式会社 | エステルの製造方法 |
US7612221B2 (en) * | 2002-04-02 | 2009-11-03 | The United States Of America As Represented By The Secretary Of Agriculture | Production of fatty acid alkyl esters |
AT504727A1 (de) * | 2002-04-12 | 2008-07-15 | Energea Umwelttechnologie Gmbh | Verfahren und anlage zur veresterung von fettsäuren |
DE10243700A1 (de) * | 2002-09-20 | 2004-04-01 | Oelmühle Leer Connemann Gmbh & Co. | Verfahren und Vorrichtung zur Herstellung von Biodiesel |
FR2852602B1 (fr) * | 2003-03-17 | 2007-08-10 | Inst Francais Du Petrole | Procede d'alcoolyse d'huiles acides d'origine vegetale ou animale |
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KR101265759B1 (ko) | 2006-04-28 | 2013-05-20 | 에스케이케미칼주식회사 | 지방산을 이용한 지방산알킬에스테르의 제조방법 및 장치 |
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- 2008-04-01 JP JP2011502839A patent/JP5380523B2/ja active Active
- 2008-04-01 CN CN201510500990.XA patent/CN105176696A/zh active Pending
- 2008-04-01 US US12/934,923 patent/US8530684B2/en active Active
- 2008-04-01 CN CN200880128327XA patent/CN102015615A/zh active Pending
- 2008-04-01 WO PCT/KR2008/001831 patent/WO2009123369A1/en active Application Filing
- 2008-04-01 MX MX2010010879A patent/MX2010010879A/es active IP Right Grant
- 2008-04-01 PL PL08741082.5T patent/PL2257518T3/pl unknown
- 2008-04-01 ES ES08741082.5T patent/ES2575099T3/es active Active
- 2008-04-01 EP EP08741082.5A patent/EP2257518B1/en active Active
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- 2011-10-07 HK HK16101338.1A patent/HK1213283A1/zh unknown
Also Published As
Publication number | Publication date |
---|---|
US20110028747A1 (en) | 2011-02-03 |
JP2011516466A (ja) | 2011-05-26 |
CN102015615A (zh) | 2011-04-13 |
EP2257518B1 (en) | 2016-03-09 |
ES2575099T3 (es) | 2016-06-24 |
PL2257518T3 (pl) | 2016-09-30 |
EP2257518A4 (en) | 2013-09-11 |
HK1213283A1 (zh) | 2016-06-30 |
MX2010010879A (es) | 2010-10-26 |
CN105176696A (zh) | 2015-12-23 |
WO2009123369A1 (en) | 2009-10-08 |
EP2257518A1 (en) | 2010-12-08 |
US8530684B2 (en) | 2013-09-10 |
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