EP0658183A1 - Verfahren zur herstellung von fettsäureestern kurzkettiger einwertiger alkohole. - Google Patents
Verfahren zur herstellung von fettsäureestern kurzkettiger einwertiger alkohole.Info
- Publication number
- EP0658183A1 EP0658183A1 EP92922141A EP92922141A EP0658183A1 EP 0658183 A1 EP0658183 A1 EP 0658183A1 EP 92922141 A EP92922141 A EP 92922141A EP 92922141 A EP92922141 A EP 92922141A EP 0658183 A1 EP0658183 A1 EP 0658183A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fatty acid
- oil
- short
- stage
- monoalkylated
- 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.)
- Granted
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
Definitions
- the present invention relates to a process for the production of fatty acid esters and / or fatty acid ester mixtures of short-chain monohydric alcohols or monoalkylated diols by transesterification of fatty acid glycerides with the short-chain alcohols or monoalkylated diols in the presence of basic catalysts.
- the fatty acid esters produced according to the invention are suitable as pharmaceutical, dietary or cosmetic raw materials, as intermediate products for further fatty acid derivatives, such as fatty alcohols, fatty amines, surfactants etc., and as lubricants, plasticizers, hydraulic oils, fuels and fuels for operating diesel engines
- the main disadvantages of the known processes are that the fatty acid glycerides, if the transesterification is to take place at temperatures below 100 ° C. and without pressure, are ripened after they have been obtained, for example by pressing or extraction. must be freed, in particular from free fatty acids and phosphates. If, on the other hand, unpurified fatty acid glycerides are used, high pressures and high temperatures or other measures, such as pre-esterification of the free fatty acids, alcohol vapor countercurrent processes, etc., must be used. All of these measures require a great deal of technical and apparatus expenditure and thus high investment costs and make it more difficult or impossible to use these processes for obtaining renewable and environmentally friendly energy sources in small plants, for example in the context of agricultural operations or in developing countries.
- a further difficulty is the removal of portions of the basic catalyst remaining in the fatty acid ester phase. If this removal is carried out by washing with water or with dilute acids, the formation of emulsions, especially when using phosphate-rich oils, and due to high levels of Sewage causes problems. If ion exchangers are used, their regeneration and the resulting waste water cause problems.
- This aim is achieved according to the invention in that a) the transesterification in the presence of 0.5 to 5.0%, based on the mass of the fatty acid glyceride used, of a basic catalyst with an excess of the short-chain alcohol or monoalkylated diol of 1.1 up to 3.0 moles per mole of fatty acid bound to glycerol, optionally in the presence of 0.5% to 10% water, based on the mass of the fatty acid glyceride used, in several, preferably two, stages that b) the glycerol phase obtained after transesterification after the first stage by settling and separating, either in whole or in part, but at least to a tenth, after the transesterification of the second stage or a further stage, this is added with stirring and that c) after renewed settling and separating the Glycerol phase and after removal of excess short-chain alcohol or monoalkylated diol an optionally diluted organic or inorganic acid is added with stirring, after phase separation has taken place,
- Fatty acid esters produced in this way meet all purity requirements placed on diesel fuels without further treatment.
- Basic alkali metal or alkaline earth metal compounds for example the oxides, hydroxides, alcoholates, borates, carbonates, aluminates or silicates of lithium, sodium potassium or calcium, are suitable as catalysts as concentrated aqueous or alcoholic solutions.
- the short-chain alcohols are monohydric aliphatic alcohols with 1 to 5 carbon atoms, for example methanol, ethanol, butanols, acid amyl alcohols, neopentyl alcohol and
- Fusel oils as well as aliphatic diols with 2 to 5 carbon atoms
- men which are mo ⁇ o-alkylated by alkyl radicals having 1 to 3 carbon atoms, such as, for example, ethylene glycol monoethyl ether, 1,2-propanediol monomethyl ether or ethylene glycol mono-i-propyl ether.
- alkyl radicals having 1 to 3 carbon atoms such as, for example, ethylene glycol monoethyl ether, 1,2-propanediol monomethyl ether or ethylene glycol mono-i-propyl ether.
- the alcohols or monoalkylated diols mentioned can be used both purely and in any mixing ratio with one another.
- oils All naturally occurring vegetable or animal fats and oils, all partially and fully synthetic fatty acid glycerides and used fatty acid glycerides, such as e.g. used edible oils and fats, as well as used technical fats and oils based on glyceride, for example soya oil, sunflower oil, linseed oil, rapeseed oil, castor oil, palm oil, palm kernel oil, coconut oil, cottonseed oil, peanut oil, olive oil, beef tallow, used frying oil or fat, ge ⁇ needed hydraulic or lubricating oils, in question.
- the oils mentioned can be used in the raw state from hot or cold pressing or from an extraction with up to 20% free fatty acids and up to 3% phosphatides, but also in any purified form. They can be used alone or in any mixing ratio.
- suitable organic or inorganic acids are phosphoric, sulfuric, salt, nitric, boric, formic, acetic, lactic, gluconic, oxalic, succinic, maleic, tartaric, malic and citric acid as well as organic sulfonic acid and sulfuric acid semiester and concentrated solutions of acidic salts, such as potassium or sodium hydrogen sulfate, potassium or sodium dihydrogen phosphate or mono-potassium or mono-sodium dihydrogen citrate.
- acidic salts such as potassium or sodium hydrogen sulfate, potassium or sodium dihydrogen phosphate or mono-potassium or mono-sodium dihydrogen citrate.
- the acids can be used in concentrated or semi-concentrated form. 10 to 20% acid solutions can also be used.
- the transesterification by the process according to the invention takes place in such a way that the fatty acid glyceride is placed in a container such that in a first stage 4 tenths to 10 tenths of the total amount of short-chain alcohol or monoalkylated diol and 4 tenths used up to 9 tenths of the total amount of catalyst used, in concentrated aqueous or alcoholic solution, with stirring, and this mass 5 to Is stirred for 60 minutes.
- the heavier glycerol phase is discharged through an opening at the bottom of the container and the supernatant is in a second or in further stages with the remaining amount (s) of the short-chain alcohol or diol or without another Add the same and the remaining amount (s) of the basic catalyst with stirring and stir for 5 to 60 minutes. Then the previously drained glycerol phase is added in whole or in part, but at least one tenth, and this mass is stirred for 2 to 10 minutes. In the more than two-stage implementation processes, the glycerol phase from the previous stage is added to the next stage after its transesterification.
- the glycerol phase is drained again and the excess fatty acid ester is freed of excess alcohol or diol in a known manner by distillative or adsorptive methods and, if appropriate, after settling and separating off a further amount of a heavier phase, an optionally diluted organic or inorganic Acid is added and this mass is stirred for 10 to 60 minutes.
- the amount of acid required is very small. It depends on the amount of basic catalyst remaining in the fatty acid ester and is in the range from 0.02 to 0.1% by weight, based on the amount of the fatty acid ester.
- the acid is added in an amount of 1% to 10% and the mass is stirred.
- the acid phase is used again for the next batch, until the capacity is exhausted, that is to say the acid is approximately neutralized.
- the protruding fatty acid ester is removed and, if appropriate, is preferably filtered using a coalescence filter.
- the same short-chain alcohol or the same monoalkylated diol or a certain mixing ratio of these and the same catalyst are preferably used in all the conversion steps. It is also possible to use one of the alcohols mentioned or a diol in the first stage and another alcohol or another diol mentioned in the further stages. Furthermore, it is possible to use one of the catalysts mentioned in the first stage and another in the second stage.
- the transesterification according to the process according to the invention takes place at atmospheric pressure and temperatures between -25 ° C. and + 60 ° C., provided the viscosity or the pour point of the fatty acid glyceride permits this. It may be necessary to convert fatty acid glycerides, which are in solid form at ambient temperature, into the liquid state by heating
- the fatty acid esters can be prepared by the process according to the invention in open or closed containers of any size, which are advantageously equipped with a drain device on the bottom.
- stirring can be carried out by hand, using an electric or compressed air-operated, simple paddle stirrer or advantageously in closed containers with a permanently installed agitator.
- the phases are separated by the action of gravity. Excess alcohol or monoalkylated diol is removed in a known manner, for example by means of falling film evaporators, blowing through air, nitrogen or water vapor.
- the necessary manipulations can be carried out by hand or automated as desired. If suitable metering devices, a special reaction vessel and a corresponding monitoring system are present, the method according to the invention can also be carried out continuously.
- the process is characterized by the following main advantages: very fast and exact separation of the phases, even at high ones
- the yield of rapeseed methyl ester is 95 g.
- Unesterified fatty acid glycerides 0.9% free glycerin: 0.02% total glycerin: 0.15% sulfate ash: 0.01% coking residue according to Conradson: 0.04%
- Example 2
Landscapes
- Chemical & Material Sciences (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 Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT0220091A AT397510B (de) | 1991-11-06 | 1991-11-06 | Verfahren zur herstellung von fettsäureestern kurzkettiger alkohole |
AT2200/91 | 1991-11-06 | ||
PCT/AT1992/000136 WO1993009212A1 (de) | 1991-11-06 | 1992-11-03 | Verfahren zur herstellung von fettsäureestern kurzkettiger einwertiger alkohole |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0658183A1 true EP0658183A1 (de) | 1995-06-21 |
EP0658183B1 EP0658183B1 (de) | 1997-03-12 |
Family
ID=3529860
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92922141A Expired - Lifetime EP0658183B1 (de) | 1991-11-06 | 1992-11-03 | Verfahren zur herstellung von fettsäureestern kurzkettiger einwertiger alkohole |
Country Status (9)
Country | Link |
---|---|
US (1) | US5434279A (de) |
EP (1) | EP0658183B1 (de) |
AT (2) | AT397510B (de) |
AU (1) | AU2880992A (de) |
CA (1) | CA2122713A1 (de) |
CZ (1) | CZ111694A3 (de) |
DE (1) | DE59208211D1 (de) |
HU (1) | HU212123B (de) |
WO (1) | WO1993009212A1 (de) |
Cited By (4)
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WO2012054946A1 (de) | 2010-10-28 | 2012-05-03 | Theodor Wimmer | Verfahren zur herstellung von fettsäureestern niederer alkohole |
US8692008B2 (en) | 2008-11-17 | 2014-04-08 | Basf Se | Use of methanesulfonic acid for preparing fatty acid esters |
WO2020074435A1 (en) | 2018-10-10 | 2020-04-16 | Basf Se | Method of producing biodiesel |
WO2021204610A1 (en) | 2020-04-07 | 2021-10-14 | Basf Se | Energy efficient biodiesel production from natural or industrial waste oil |
Families Citing this family (49)
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DE4318673C2 (de) * | 1993-06-04 | 1999-07-29 | Pfanni Werke Gmbh & Co Kg | Keimhemmungsmittel für Kartoffeln |
US5424467A (en) * | 1993-07-14 | 1995-06-13 | Idaho Research Foundation | Method for purifying alcohol esters |
AT399336B (de) * | 1993-07-14 | 1995-04-25 | Martin Mag Dr Mittelbach | Verfahren zur herstellung von fettsäurealkylestern |
AT405938B (de) * | 1994-06-29 | 1999-12-27 | Lackner Johannes | Kontinuierliches umesterungsverfahren, durchflussreaktor sowie trennrohr |
AU5413196A (en) * | 1995-04-27 | 1996-11-18 | Sucher & Holzer Bauplanungs- Und Handelsgesellschaft M.B.H. | Worm press |
AT406870B (de) * | 1995-06-16 | 2000-10-25 | Sucher & Holzer Bauplan Handel | Verfahren zur herstellung von fettsäurealkylestern |
US6084122A (en) * | 1997-10-31 | 2000-07-04 | Celanese International Corporation | Sulfur removal process from an acrylate waste stream |
DE69812682T2 (de) * | 1997-10-31 | 2003-12-18 | Celanese International Corp., Dallas | Entfernung von schwefel aus einem acrylatstrom |
US6914137B2 (en) * | 1997-12-06 | 2005-07-05 | Dna Research Innovations Limited | Isolation of nucleic acids |
AT406871B (de) * | 1998-05-22 | 2000-10-25 | Mittelbach Martin | Verfahren zum verwerten eines esters, der aus mindestens einer fettsäure und einem mono-, di- oder trisaccharid gebildet ist |
US6127560A (en) * | 1998-12-29 | 2000-10-03 | West Central Cooperative | Method for preparing a lower alkyl ester product from vegetable oil |
AU2862100A (en) * | 1999-01-27 | 2000-08-18 | Folim G. Halaka | Materials and methods for the purification of polyelectrolytes |
DE19925871A1 (de) * | 1999-06-07 | 2000-12-21 | At Agrar Technik Gmbh | Verfahren zur Herstellung von Fettsäureestern einwertiger Alkylalkohole und deren Verwendung |
WO2000075096A1 (en) * | 1999-06-09 | 2000-12-14 | Cognis Corporation | Process for the reduction of glycerin in transesterification operations |
AT410443B (de) * | 2000-11-08 | 2003-04-25 | Wimmer Theodor | Verfahren zur herstellung von fettsäureestern niederer alkohole |
US8110351B2 (en) | 2002-01-16 | 2012-02-07 | Invitrogen Dynal As | Method for isolating nucleic acids and protein from a single sample |
ES2194598B2 (es) * | 2002-01-25 | 2006-04-01 | Universidad Complutense De Madrid | Procedimiento de transesterificacion de trigliceridos con monoalcoholes de bajo peso molecular para obtencion de esteres de alcoholes ligeros utilizando catalizadores mixtos. |
DE10257215B4 (de) * | 2002-12-07 | 2005-12-22 | Lurgi Ag | Verfahren zur Verbesserung der Langzeitstabilität von Biodiesel |
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 |
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 |
KR100566106B1 (ko) | 2003-03-28 | 2006-03-30 | 한국에너지기술연구원 | 바이오디젤유의 제조방법 |
CN1301322C (zh) * | 2005-01-12 | 2007-02-21 | 李搏 | 快速制备生物柴油的方法 |
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 |
FR2890962B1 (fr) * | 2005-09-21 | 2007-11-23 | Inst Francais Du Petrole | Procede ameliore de fabrication d'esters ethyliques a partir de corps gras d'origine naturelle |
FR2890961B1 (fr) * | 2005-09-21 | 2007-11-23 | Inst Francais Du Petrole | Procede perfectionne de fabrication d'esters ethyliques a partir de corps gras d'origine naturelle |
US20080113067A1 (en) * | 2005-10-17 | 2008-05-15 | Monoj Sarma | Protein-Containing Food Product and Coating for a Food Product and Method of Making Same |
US20070087085A1 (en) * | 2005-10-17 | 2007-04-19 | Bunge Oils, Inc. | Protein-containing food product and coating for a food product and method of making same |
EP1788065A1 (de) * | 2005-11-18 | 2007-05-23 | Biodiesel Engineering Limited | Verfahren und Anlage zum Reinigen von Biodiesel |
JP2007145759A (ja) * | 2005-11-28 | 2007-06-14 | Rebo International:Kk | 脂肪酸アルキルエステルの製造方法 |
US20070148311A1 (en) * | 2005-12-22 | 2007-06-28 | Bunge Oils, Inc. | Phytosterol esterification product and method of make same |
US20070261294A1 (en) * | 2006-05-10 | 2007-11-15 | Aiken John E | Process for production of biodiesel from high acid feed |
GB2438403B (en) | 2006-05-25 | 2011-02-23 | Viktor Fedorovych Dekhtiaruk | Manufacture of biodiesel |
WO2008049260A2 (de) * | 2006-10-27 | 2008-05-02 | Mecan Ecosystems Ag | Verfahren zur herstellung von fettsäureestern |
US20080282606A1 (en) * | 2007-04-16 | 2008-11-20 | Plaza John P | System and process for producing biodiesel |
US20090038692A1 (en) * | 2007-08-09 | 2009-02-12 | 21St Century R & D, Llc | Modification of vegetable oils for fuel applications |
US20110139106A1 (en) | 2007-08-09 | 2011-06-16 | 21St Century R & D, Llc | Modification of fats and oils for fuel and lubricating applications |
JP2010538127A (ja) * | 2007-08-31 | 2010-12-09 | ジェイエイチ バイオテック,インコーポレーティッド. | 固形状脂肪酸の製造 |
US8022236B2 (en) * | 2007-10-12 | 2011-09-20 | Aiken John E | Fatty acid alkyl ester production from oleaginous seeds |
CN103788027A (zh) * | 2008-01-24 | 2014-05-14 | 普立万公司 | 用于环氧化大豆脂肪酸/脂肪酸酯的酯化的催化剂及其使用方法 |
US8324413B2 (en) * | 2008-12-23 | 2012-12-04 | Texaco Inc. | Low melting point triglycerides for use in fuels |
GB2466493A (en) * | 2008-12-23 | 2010-06-30 | Desmet Ballestra Engineering Sa | Process for the production and treatment of biodiesel with improved cold soak test results |
US8361172B2 (en) * | 2008-12-23 | 2013-01-29 | Chevron U.S.A. Inc. | Low melting point triglycerides for use in fuels |
CN101914014B (zh) * | 2010-09-03 | 2013-09-25 | 北京康泰隆科技发展有限公司 | 用于合成及纯化化妆品用合成油脂的方法、及通过其获得的化妆品用合成油脂 |
FR3002230B1 (fr) | 2013-02-15 | 2016-02-05 | Arkema France | Utilisation de mercapto-esters methyliques en tant qu'agents de transfert de chaine |
FR3002936B1 (fr) | 2013-03-06 | 2015-03-06 | Arkema France | Utilisation d'acide sulfonique pour la recuperation de glycerol issu de la reaction de trans-esterification de triglycerides |
WO2014201001A1 (en) | 2013-06-11 | 2014-12-18 | Renewable Energy Group, Inc. | Production of biodiesel and products obtained therefrom |
US9328054B1 (en) | 2013-09-27 | 2016-05-03 | Travis Danner | Method of alcoholisis of fatty acids and fatty acid gyicerides |
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BR8300429A (pt) * | 1983-01-28 | 1984-09-04 | Brasil Pesquisa Agropec | Processo da transesterificacao de oleos vegetais |
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 |
EP0131991B1 (de) * | 1983-07-12 | 1986-12-03 | Metallgesellschaft Ag | Kontinuierliches Alkoholyseverfahren |
DE3325066A1 (de) * | 1983-07-12 | 1985-01-24 | Metallgesellschaft Ag, 6000 Frankfurt | Kontinuierliches alkoholyseverfahren |
DE3707563A1 (de) * | 1987-03-10 | 1988-09-22 | Klaus Dr Ing Scharmer | Verfahren zur alkoholyse von fettsaeureglyceriden und vorrichtung zum durchfuehren des verfahrens |
SE9001245L (sv) * | 1990-04-05 | 1991-10-06 | Carl Johan Lindquist | Foerestringsprocess |
AT394374B (de) * | 1990-06-29 | 1992-03-25 | Wimmer Theodor | Verfahren zur herstellung von fettsaeureestern niederer alkohole |
AT394571B (de) * | 1991-01-10 | 1992-05-11 | Wimmer Theodor | Verfahren zur herstellung von fettsaeureestern kurzkettiger alkohole |
-
1991
- 1991-11-06 AT AT0220091A patent/AT397510B/de not_active IP Right Cessation
-
1992
- 1992-11-03 US US08/232,285 patent/US5434279A/en not_active Expired - Fee Related
- 1992-11-03 AT AT92922141T patent/ATE150074T1/de active
- 1992-11-03 WO PCT/AT1992/000136 patent/WO1993009212A1/de active IP Right Grant
- 1992-11-03 CA CA002122713A patent/CA2122713A1/en not_active Abandoned
- 1992-11-03 AU AU28809/92A patent/AU2880992A/en not_active Abandoned
- 1992-11-03 EP EP92922141A patent/EP0658183B1/de not_active Expired - Lifetime
- 1992-11-03 HU HU9401330A patent/HU212123B/hu not_active IP Right Cessation
- 1992-11-03 CZ CZ941116A patent/CZ111694A3/cs unknown
- 1992-11-03 DE DE59208211T patent/DE59208211D1/de not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO9309212A1 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8692008B2 (en) | 2008-11-17 | 2014-04-08 | Basf Se | Use of methanesulfonic acid for preparing fatty acid esters |
WO2012054946A1 (de) | 2010-10-28 | 2012-05-03 | Theodor Wimmer | Verfahren zur herstellung von fettsäureestern niederer alkohole |
WO2020074435A1 (en) | 2018-10-10 | 2020-04-16 | Basf Se | Method of producing biodiesel |
WO2021204610A1 (en) | 2020-04-07 | 2021-10-14 | Basf Se | Energy efficient biodiesel production from natural or industrial waste oil |
US12031107B2 (en) | 2020-04-07 | 2024-07-09 | Basf Se | Energy efficient biodiesel production from natural or industrial waste oil |
Also Published As
Publication number | Publication date |
---|---|
HUT66403A (en) | 1994-11-28 |
AT397510B (de) | 1994-04-25 |
US5434279A (en) | 1995-07-18 |
CA2122713A1 (en) | 1993-05-13 |
CZ111694A3 (en) | 1995-02-15 |
DE59208211D1 (de) | 1997-04-17 |
EP0658183B1 (de) | 1997-03-12 |
WO1993009212A1 (de) | 1993-05-13 |
ATA220091A (de) | 1992-11-15 |
AU2880992A (en) | 1993-06-07 |
ATE150074T1 (de) | 1997-03-15 |
HU212123B (en) | 1996-02-28 |
HU9401330D0 (en) | 1994-08-29 |
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