WO1997000234A1 - Verfahren zur herstellung von fettsäurealkylestern - Google Patents
Verfahren zur herstellung von fettsäurealkylestern Download PDFInfo
- Publication number
- WO1997000234A1 WO1997000234A1 PCT/AT1996/000084 AT9600084W WO9700234A1 WO 1997000234 A1 WO1997000234 A1 WO 1997000234A1 AT 9600084 W AT9600084 W AT 9600084W WO 9700234 A1 WO9700234 A1 WO 9700234A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phase
- alcohol
- transesterification
- crude ester
- catalyst
- Prior art date
Links
Classifications
-
- 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
-
- 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
Definitions
- the invention relates to a process for the preparation of fatty acid alkyl esters by transesterification of triglycerides with an alcohol in the presence of a basic catalyst.
- the transesterification is the conversion of triglycerides, i.e. vegetable and animal fats and oils, with alcohols, such as methanol, ethanol, butanol and isopropanol, in particular methanol and ethanol, to be understood, the monoesters of the fatty acids and glycerol being formed.
- triglycerides i.e. vegetable and animal fats and oils
- alcohols such as methanol, ethanol, butanol and isopropanol, in particular methanol and ethanol, to be understood, the monoesters of the fatty acids and glycerol being formed.
- Fatty acid methyl esters are becoming increasingly important as a diesel substitute fuel.
- the transesterification begins with a two-phase system consisting of triglyceride and alcohol, which contains the catalyst, but with increasing progress of the reaction and formation of ester, a homogeneous phase is formed, which in turn becomes two-phase through the formation and excretion of glycerol (crude ester phase and glycerol phase).
- AT-B 394 374 Such a method is known from AT-B 394 374. According to this process, an excess of the alcohol used is used from 1.10 to 1.80 mol per mol of fatty acid esterified with glycerol.
- AT-B 388 743 discloses a process for producing a fatty acid mixture from waste fats or oils and the use of this mixture as a fuel.
- AT-B 397 966 also describes the production of fatty acid esters of lower monohydric alcohols by transesterification of, for example, rapeseed oil. According to this process, the transesterification is carried out in the presence of a solid basic catalyst with a catalyst excess of at most 1.6 mol per mol of fatty acid bound as glyceride.
- a two-stage or multi-stage transesterification process is known from AT-B 397 510.
- Basic catalysts for example alkali metal hydroxides, metal hydrides, alcoholates, carbonates or acetates, and acidic catalysts, for example mineral acids, are usually used as catalysts for the transesterification.
- the most commonly used catalysts are sodium and potassium hydroxide as well as sodium methylate, which are dissolved in alcohol, for example added to a vegetable oil.
- AT-B 386 222 Such a method is known from AT-B 386 222.
- Previous transesterification processes which are carried out at room temperature, require at least 2 transesterification stages in order to increase the yield of ester to over 90%.
- a yield of 80-90% is achieved in the first transesterification stage.
- the esterification is carried out in a second transesterification stage, the yield being increased to 99-99.3%.
- the total amount of alcohol / catalyst is divided between the two stages in a ratio of 75:25, so that there is a relatively large excess in each case.
- the object of the invention is to provide an improved process for the preparation of fatty acid alkyl esters by transesterification of triglycerides, in which the amount of alcohol and catalyst is further reduced.
- the triglyceride is mixed with the alcohol and the catalyst (s) and reacted to form two liquid phases, a crude ester phase and a glycerol phase;
- part (A) of the crude ester phase is purified, whereby essentially pure fatty acid alkyl ester is obtained;
- part (B) is mixed with further triglyceride to be reestablished, further alcohol and further catalyst (s) and reacted to form two further liquid phases, a further crude ester phase and a further glycerol phase; after which steps (2) to (5) are repeated.
- a mixture of catalysts can also be used in the process according to the invention.
- a preferred embodiment of the process according to the invention is that the crude ester phase in step (3) is divided into part (A) and part (B) in a ratio between 1: 1 and 1:99, in particular between 1: 3 and 1:99 .
- the crude ester phase is best cleaned by washing with water, especially hot water.
- the process according to the invention can be carried out continuously.
- Methanol or ethanol are particularly suitable as alcohol for the transesterification according to the invention.
- the process according to the invention is further characterized in that it can be carried out under normal conditions, that is to say at room temperature and normal pressure.
- Fats and oils of vegetable and animal origin can be used as triglycerides in the process according to the invention.
- examples include: Corn oil, cottonseed oil, soybean oil, sunflower oil, rapeseed oil, peanut oil, coconut and other palm oils, linseed oil, tallow tree oil, castor oil, fish oil, whale tear, tallow, Sweat fat, oils from marine and terrestrial animals, oils from bacteria, algae and vegetable lipids.
- the alcohol and catalyst content contained in this phase is returned, so that this enrichment can reduce the need for further alcohol and catalyst.
- This has the advantage that the total amount of alcohol can be reduced to about 125% of the stoichiometrically necessary amount when starting the process according to the invention.
- the amount of catalyst can be reduced to 1.1% of the amount of triglyceride.
- the procedure according to the invention can dispense with dynamic regulation or quantity measurements in each phase, as well as filling volume measurement.
- the four process parameters i.e. The supply of triglyceride, alcohol / catalyst mixture and part (B) of the crude ester phase, and discharge of part (A) of the crude ester phase, are set so that the process according to the invention can run without further monitoring.
- the process according to the invention can be optimized simply by adjusting the ratio of part (A) to part (B) of the crude ester phase.
- the need for control and measurement technology is practically reduced to zero.
- Example A the Production of the starting batch according to the known two-stage transesterification is described and the method according to the invention is described in Example B.
- a transesterification reactor equipped with a stirring device was charged with 1,000 kg of vegetable oil (filtered; moisture content: ⁇ 0.1% by weight). A mixture of 120 kg of methanol and 10.5 kg of KOH was then added with stirring, and stirring was continued for 30 minutes after the addition was complete.
- the reaction mixture was then pumped into a settling tank to allow the phases to form. After the phases had formed, the glycerol phase was separated off and the remaining phase, which was a mixture of oil and ester, was pumped back into the reactor, where it was reacted once more with a mixture of 40 kg of methanol and 3.5 kg of KOH. The reaction mixture was then pumped again into the settling tank and the phases were allowed to form. After the glycerol phase had been separated off, the ester phase was washed with water to the neutral point and had an ester content of 99.4% by weight.
- a first mixture of methanol and KOH was prepared, mixed with the ester obtained in Example A in a weight ratio of 1: 9 (methanol / KOH + triglyceride: ester) and fed to the transesterification reactor.
- the transesterification was carried out at ambient temperature in a time of about 25 minutes. After the transesterification, the phase mixture formed was removed from the reactor and separated into the glycerol phase and the ester phase in a centrifuge.
- the remaining 90% of the ester phase obtained was used as part (B) for a next transesterification and mixed with a second mixture of methanol and KOH in a weight ratio of 1: 9 (methanol / KOH + triglyceride: ester) and fed to the transesterification reactor.
- the further procedure was as described above.
- 10% by weight of the ester phase obtained was thus removed from the process and 90% by weight of the ester phase obtained was recycled for the next transesterification. Equally good results can be obtained if between 1 and 25% by weight of the ester phase are recycled, if between 99 and 75% by weight of the ester phase are recycled.
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)
- Fats And Perfumes (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU53925/96A AU5392596A (en) | 1995-06-16 | 1996-04-26 | Method of producing fatty acid alkyl esters |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT102795A AT406870B (de) | 1995-06-16 | 1995-06-16 | Verfahren zur herstellung von fettsäurealkylestern |
ATA1027/95 | 1995-06-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997000234A1 true WO1997000234A1 (de) | 1997-01-03 |
Family
ID=3505109
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/AT1996/000084 WO1997000234A1 (de) | 1995-06-16 | 1996-04-26 | Verfahren zur herstellung von fettsäurealkylestern |
Country Status (3)
Country | Link |
---|---|
AT (1) | AT406870B (de) |
AU (1) | AU5392596A (de) |
WO (1) | WO1997000234A1 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6769529B2 (en) | 2000-12-05 | 2004-08-03 | Quebec Inc. | Turning device for lumber and the like |
US7834203B2 (en) | 2003-03-28 | 2010-11-16 | Korea Institute Of Energy Research | Manufacturing method of bio-diesel oil |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT388743B (de) * | 1986-09-02 | 1989-08-25 | Mittelbach Martin | Verfahren zur herstellung eines fettsaeureestergemisches aus abfallfetten bzw. oelen und verwendung dieses gemisches als kraftbzw. brennstoff |
WO1993009212A1 (de) * | 1991-11-06 | 1993-05-13 | Theodor Wimmer | Verfahren zur herstellung von fettsäureestern kurzkettiger einwertiger alkohole |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT386222B (de) * | 1986-09-02 | 1988-07-25 | Hans Dr Junek | Verfahren und vorrichtung zur herstellung eines als kraft- bzw. brennstoff geeigneten fettsaeureestergemisches |
AT394374B (de) * | 1990-06-29 | 1992-03-25 | Wimmer Theodor | Verfahren zur herstellung von fettsaeureestern niederer alkohole |
AT397966B (de) * | 1993-01-25 | 1994-08-25 | Wimmer Theodor | Verfahren zur herstellung von fettsäureestern niederer einwertiger alkohole |
-
1995
- 1995-06-16 AT AT102795A patent/AT406870B/de not_active IP Right Cessation
-
1996
- 1996-04-26 AU AU53925/96A patent/AU5392596A/en not_active Abandoned
- 1996-04-26 WO PCT/AT1996/000084 patent/WO1997000234A1/de active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT388743B (de) * | 1986-09-02 | 1989-08-25 | Mittelbach Martin | Verfahren zur herstellung eines fettsaeureestergemisches aus abfallfetten bzw. oelen und verwendung dieses gemisches als kraftbzw. brennstoff |
WO1993009212A1 (de) * | 1991-11-06 | 1993-05-13 | Theodor Wimmer | Verfahren zur herstellung von fettsäureestern kurzkettiger einwertiger alkohole |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6769529B2 (en) | 2000-12-05 | 2004-08-03 | Quebec Inc. | Turning device for lumber and the like |
US7834203B2 (en) | 2003-03-28 | 2010-11-16 | Korea Institute Of Energy Research | Manufacturing method of bio-diesel oil |
Also Published As
Publication number | Publication date |
---|---|
ATA102795A (de) | 2000-02-15 |
AU5392596A (en) | 1997-01-15 |
AT406870B (de) | 2000-10-25 |
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