EP1495099A1 - Verfahren und anlage zur veresterung von fetts uren - Google Patents
Verfahren und anlage zur veresterung von fetts urenInfo
- Publication number
- EP1495099A1 EP1495099A1 EP03711704A EP03711704A EP1495099A1 EP 1495099 A1 EP1495099 A1 EP 1495099A1 EP 03711704 A EP03711704 A EP 03711704A EP 03711704 A EP03711704 A EP 03711704A EP 1495099 A1 EP1495099 A1 EP 1495099A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- reaction
- pressure
- esterification
- reaction section
- fatty acids
- 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.)
- Withdrawn
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
-
- 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
- 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 invention relates to a process for the esterification of fatty acids and / or of fatty acids contained in fats and oils with lower monohydric alcohols, in particular methanol, the fatty acids having strong mineral acids, for example sulfuric acid, dissolved in lower alcohols, in particular in methanol and / or only in lower alcohols, especially in methanol, are mixed with acidic ion exchange resins.
- the invention also relates to a plant for carrying out the method.
- a process for the esterification of a fatty acid / fatty acid ester mixture isolated from the “glycerol phase” is described in EP 708 813 A, the free fatty acids obtained from the neutralization of the “glycerol phase” with methanol and conc. Sulfuric acid as a catalyst are heated to 85 ° C for two hours, the free fatty acid content falling from about 50% to 12.5% and the entire mixture being fed to an alkali-catalyzed transesterification without further treatment and the catalyst acid being discharged via the transesterification process.
- the object of the present invention is to provide a method of the type cited at the outset which permits rational production in an economically justifiable system, preferably in a large industrial system, but also makes small systems economical.
- the process according to the invention is characterized in that the phase interfaces of the mixture are increased in a reaction zone by high or strong, dynamic shear forces and / or turbulence, the esterification starting under high pressure and the pressure being reduced during the esterification, the pressure loss being a maintains a high phase interface and that this reaction is carried out in the reaction zone at high temperature.
- the possibility is created to accelerate the reaction by enlarging the interfaces and by dynamic processes during the esterification. Due to the high or strong dynamic turbulence, the drops in the liquid phases are effectively reduced in size, which means that much smaller drops are created, thus giving a much larger surface area and the chemical equilibrium is reached more quickly. The balance is sometimes less than a minute. This results in an immense reduction in the response time.
- this method according to the invention is not suitable for the so-called settling process, since the settling times would take too long due to the fine distribution of the drops.
- the pressure at the start of the reaction zone is 2 to 500 bar, in particular 50 to 200 bar and very particularly between 70 and 150 bar. It is advantageous that the methanol remains liquid due to the high pressure.
- the reaction in the reaction zone is carried out at a temperature of 50 to 300 ° C., in particular at 80 to 150 ° C.
- the high reaction rate is advantageously achieved by the high temperature.
- the high shear forces or strong dynamic turbulence are generated by mechanical internals.
- This type of device is simple in construction and therefore also low-maintenance in operation.
- the turbulence arises primarily from the rapid flow of the mixture around the internals.
- such a reactor is inexpensive and extremely space-saving.
- the large phase interfaces are generated by ultrasound.
- the integration of an ultrasound device has proven to be advantageous since the esterification can thereby be accelerated in a targeted manner through large interfaces.
- Reaction line an unturbulent post-reaction line.
- the residence time of the reaction mixture in the after-reaction section increases the degree of esterification.
- a pressure, preferably the outlet pressure, of the reaction zone is maintained or, if appropriate, reduced further in the after-reaction zone. Maintaining the pressure also helps to improve the degree of esterification. According to certain specifications in the esterification process, a further pressure reduction can also be advantageous.
- the post-reaction zone is filled with strongly acidic ion exchangers.
- ion exchangers it is known that the fats are not mixed with acids.
- An optimal esterification process is also achieved with such a process.
- the system according to the invention is characterized in that the reaction zone is a tube filled with balls of the same or different sizes and / or optionally has internals such as baffles, propellers or the like.
- the advantageous turbulence arises primarily from the rapid flow of the mixture around the balls or internals.
- an ultrasound device is provided in the reaction path.
- the integration of an ultrasound device has proven to be proven to be advantageous, since the transesterification can thus be accelerated in a targeted manner through large interfaces.
- a heater is connected upstream of the reaction zone and, if appropriate, a cooler is connected downstream of the reaction zone or the afterreaction zone.
- the reaction mixture can be brought to the desired high temperature by the heater and cooled with the cooler in accordance with the specifications for the process.
- a pump in particular a high-pressure pump, is provided for introducing the liquid into the reaction zone.
- a high-pressure pump has advantageously proven itself because the turbulence for the transesterification achieves high dynamics and thus a large interface.
- the figure shows schematically a plant for carrying out the process for the esterification of fatty acids.
- the raw material for example higher, saturated and / or unsaturated fats of vegetable and / or animal origin, which contain free fatty acids, flows from a container 1 into a feed line 2 to a reaction zone 3.
- the method is particularly suitable for fats, which have a higher or higher proportion, preferably more than 5%, of free fatty acids.
- This process can be used, for example, in the production of fatty acid methyl esters, which ensures high economic efficiency.
- the method can also be used for pure fatty acids.
- the lower alcohol, in particular the methanol, with the acid, in particular sulfuric acid, is pumped from the container 4 into the feed line 2 to the reaction zone 3.
- This reaction mixture is brought to the appropriate temperature via a heater 5, which is arranged upstream of the reaction zone 3.
- the reaction in reaction zone 3 is carried out at a temperature of 50 to 300 ° C., in particular at a temperature of 80 to 150 ° C.
- This heated reaction mixture is introduced into the reaction zone 3 via a high-pressure pump 6.
- the reaction mixture is exposed to high shear forces, as a result of which strong dynamic turbulence is generated. This means that the phase interfaces of the reaction mixture are increased enormous.
- These high shear forces or strong dynamic turbulence are generated by mechanical installations in the reaction section 3.
- the mechanical internals in the reaction path 3 can be balls 7 of different or the same size. However, internals such as baffles, propellers or the like can also be provided, if necessary additionally.
- An ultrasound device could also be used to enlarge the phase interface of the reaction mixture. This device can of course also be provided in addition to the mechanical components.
- the reaction zone 3 can be followed by an unturbulent after-reaction zone 8, which calms the reaction mixture, possibly under the outlet pressure of the reaction zone 3.
- the after-reaction section 8 has a pressure-maintaining valve 9 at its end.
- the pressure can also be reduced in the after-reaction section 8.
- a strongly acidic ion exchanger in particular an ion exchange resin, is provided in the after-reaction zone 8.
- the after-reaction section 8 is followed by a cooler 10, which cools the reaction mixture appropriately again before it is collected in a container 11 for further processing.
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT0056902A AT504727A1 (de) | 2002-04-12 | 2002-04-12 | Verfahren und anlage zur veresterung von fettsäuren |
AT5692002 | 2002-04-12 | ||
PCT/AT2003/000101 WO2003087278A1 (de) | 2002-04-12 | 2003-04-07 | Verfahren und anlage zur veresterung von fettsäuren |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1495099A1 true EP1495099A1 (de) | 2005-01-12 |
Family
ID=29220186
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03711704A Withdrawn EP1495099A1 (de) | 2002-04-12 | 2003-04-07 | Verfahren und anlage zur veresterung von fetts uren |
Country Status (18)
Country | Link |
---|---|
US (2) | US7256301B2 (de) |
EP (1) | EP1495099A1 (de) |
JP (1) | JP2005528472A (de) |
KR (1) | KR20040101446A (de) |
CN (1) | CN1646670A (de) |
AT (1) | AT504727A1 (de) |
AU (1) | AU2003218521B2 (de) |
BR (1) | BR0309199A (de) |
CA (1) | CA2480901A1 (de) |
EA (1) | EA007630B1 (de) |
HR (1) | HRP20041057A2 (de) |
MX (1) | MXPA04010015A (de) |
NO (1) | NO20044930L (de) |
PL (1) | PL371212A1 (de) |
RS (1) | RS90004A (de) |
UA (1) | UA78767C2 (de) |
WO (1) | WO2003087278A1 (de) |
ZA (1) | ZA200408018B (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007117096A1 (en) * | 2006-04-07 | 2007-10-18 | Dowell Technology Co., Ltd. | System for alternative fuel with high efficiency of loop reactor and method thereof |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001524553A (ja) | 1997-11-24 | 2001-12-04 | エネルゲア・ウムヴェルトテヒノロギー・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 脂肪酸メチルエステルの製造方法およびそれを実現するための装置 |
AT504727A1 (de) | 2002-04-12 | 2008-07-15 | Energea Umwelttechnologie Gmbh | Verfahren und anlage zur veresterung von fettsäuren |
MY150129A (en) * | 2004-04-09 | 2013-11-29 | Archer Daniels Midland Co | Method of preparing fatty acid alkyl esters from waste or recycled fatty acid stock |
JP2006036817A (ja) * | 2004-07-22 | 2006-02-09 | Kimura Chem Plants Co Ltd | 脂肪酸エステルの製造方法および製造装置 |
WO2007126166A1 (en) | 2006-04-28 | 2007-11-08 | Sk Chemicals Co., Ltd. | Method and apparatus for preparing fatty acid alkyl ester using fatty acid |
US7767839B2 (en) * | 2006-08-24 | 2010-08-03 | Philadelphia Fry-O-Diesel, Inc. | Process of making alkyl esters of free fatty acids |
CN1919973B (zh) * | 2006-09-08 | 2011-04-06 | 浙江赞宇科技股份有限公司 | 一种连续式制备生物柴油的方法 |
JP2008207135A (ja) * | 2007-02-27 | 2008-09-11 | National Univ Corp Shizuoka Univ | 水熱酸化分解処理装置 |
US8052848B2 (en) * | 2007-06-26 | 2011-11-08 | The Penn State Research Foundation | Ultrasonic and microwave methods for enhancing the rate of a chemical reaction and apparatus for such methods |
DE102008007431A1 (de) * | 2008-02-01 | 2009-08-13 | Bayer Technology Services Gmbh | Verbessertes Verfahren zur heterogen katalysierten Veresterung von Fettsäuren |
EP2215193A4 (de) * | 2007-11-30 | 2012-08-29 | Ca Minister Natural Resources | Dampfphasenveresterung von freien fettsäuren |
CN102015615A (zh) | 2008-04-01 | 2011-04-13 | Sk化学株式会社 | 使用脂肪酸制备脂肪酸烷基酯的方法 |
KR101554607B1 (ko) | 2008-11-07 | 2015-09-22 | 에스케이케미칼주식회사 | 지방산을 이용한 지방산알킬에스테르의 제조방법 및 장치 |
ITNA20090024A1 (it) * | 2009-05-08 | 2010-11-09 | Eurochem Engineering S R L | Uso di reattori innovativi per reazioni multifasiche liquido-liquido. |
DE102009044168A1 (de) * | 2009-10-02 | 2011-04-07 | Green Finance Ag | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylestern höherer Fettsäuren |
MY151440A (en) * | 2009-10-29 | 2014-05-30 | Malaysian Palm Oil Board Mpob | A method of converting free fatty acid (ffa) from oil to methyl ester |
JP2014040527A (ja) * | 2012-08-22 | 2014-03-06 | Osaka Prefecture Univ | 脂肪酸アルキルエステルの精製方法 |
KR102327852B1 (ko) | 2013-07-22 | 2021-11-18 | 에스케이에코프라임 주식회사 | 지방을 이용한 지방산알킬에스테르의 제조방법 |
US9328054B1 (en) | 2013-09-27 | 2016-05-03 | Travis Danner | Method of alcoholisis of fatty acids and fatty acid gyicerides |
PT3347338T (pt) | 2015-09-11 | 2019-07-12 | Resiway Solucoes Sustentaveis Lda | Produção de éster de glicerol a partir de resíduos contendo óleos e/ou gorduras orgânicas |
PT109991A (pt) | 2017-03-24 | 2018-09-24 | Univ Do Porto | Catalisadores heterogéneos, processo de preparação e sua aplicação no processo de produção de ésteres alquílicos deácidos gordos. |
FI128952B (en) * | 2019-09-26 | 2021-03-31 | Neste Oyj | Preparation of renewable alkenes including metathesis |
FI128954B (en) | 2019-09-26 | 2021-03-31 | Neste Oyj | Preparation of renewable base oil including metathesis |
BR102021012721A2 (pt) | 2021-06-25 | 2022-12-27 | Petróleo Brasileiro S.A. - Petrobras | Processo de obtenção de catalisador, catalisador e processo de pré-tratamento de cargas ácidas |
CN113563977B (zh) * | 2021-07-21 | 2022-08-16 | 湖北天基生物能源科技发展有限公司 | 一种废弃油脂的处理系统和处理方法 |
BR102021016123A2 (pt) | 2021-08-16 | 2023-02-23 | Petróleo Brasileiro S.A. - Petrobras | Processo para produção de biodiesel a partir de cargas ácidas |
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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 |
DE3339051A1 (de) | 1983-10-28 | 1985-05-09 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur verbesserten destillativen aufarbeitung von glycerin |
DE3444893A1 (de) | 1984-12-08 | 1986-06-12 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von fettsaeuremethylestern |
DE3501761A1 (de) | 1985-01-21 | 1986-07-24 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur vorveresterung freier fettsaeuren in rohfetten und/oder -oelen |
BR9007038A (pt) * | 1989-01-17 | 1991-11-12 | Davy Mckee London | Processo e aparelho |
US5514820A (en) | 1989-09-29 | 1996-05-07 | Henkel Kommanditgesellschaft Auf Aktien | Continuous process for the production of lower alkyl esters |
AT394374B (de) | 1990-06-29 | 1992-03-25 | Wimmer Theodor | Verfahren zur herstellung von fettsaeureestern niederer alkohole |
EP0535290B1 (de) | 1991-09-02 | 1994-11-30 | Primavesi, Markus | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Fettsäureestern |
US5324853A (en) * | 1993-01-19 | 1994-06-28 | Exxon Chemical Patents Inc. | Process for the production of plasticizer and polyolesters |
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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 |
US5482633A (en) | 1993-10-12 | 1996-01-09 | Cargill, Incorporated | Process for removing vegetable oil waxes by fast cooling vegetable oil and using a porous non-metallic inorganic filter |
DE4338111A1 (de) | 1993-11-08 | 1995-05-11 | Henkel Kgaa | Verfahren zur Herstellung von Fettsäureniedrigalkylestern |
US5645696A (en) | 1994-11-21 | 1997-07-08 | Lucky Ltd. | Process for preparing unsaturated carboxylic acid esters and apparatus for preparing the same |
US5945529A (en) * | 1996-07-19 | 1999-08-31 | The Procter & Gamble Company | Synthesis of polyol fatty acid polyesters using column with inert gas stripping |
JP3579757B2 (ja) * | 1996-08-10 | 2004-10-20 | チッソ株式会社 | 反応槽及びカルボン酸エステル製造方法 |
US6174501B1 (en) * | 1997-10-31 | 2001-01-16 | The Board Of Regents Of The University Of Nebraska | System and process for producing biodiesel fuel with reduced viscosity and a cloud point below thirty-two (32) degrees fahrenheit |
US6015440A (en) | 1997-10-31 | 2000-01-18 | Board Of Regents Of The University Of Nebraska | Process for producing biodiesel fuel with reduced viscosity and a cloud point below thirty-two (32) degrees fahrenheit |
JP2001524553A (ja) | 1997-11-24 | 2001-12-04 | エネルゲア・ウムヴェルトテヒノロギー・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 脂肪酸メチルエステルの製造方法およびそれを実現するための装置 |
US5938328A (en) * | 1998-07-07 | 1999-08-17 | Atlantic Richfield Company | Packed bed static mixer |
AT410443B (de) * | 2000-11-08 | 2003-04-25 | Wimmer Theodor | Verfahren zur herstellung von fettsäureestern niederer alkohole |
AT504727A1 (de) | 2002-04-12 | 2008-07-15 | Energea Umwelttechnologie Gmbh | Verfahren und anlage zur veresterung von fettsäuren |
-
2002
- 2002-04-12 AT AT0056902A patent/AT504727A1/de not_active Application Discontinuation
-
2003
- 2003-04-07 RS YU90004A patent/RS90004A/sr unknown
- 2003-04-07 MX MXPA04010015A patent/MXPA04010015A/es not_active Application Discontinuation
- 2003-04-07 JP JP2003584222A patent/JP2005528472A/ja active Pending
- 2003-04-07 WO PCT/AT2003/000101 patent/WO2003087278A1/de active Application Filing
- 2003-04-07 KR KR10-2004-7016258A patent/KR20040101446A/ko not_active Application Discontinuation
- 2003-04-07 BR BR0309199-6A patent/BR0309199A/pt not_active Withdrawn
- 2003-04-07 CN CNA03808273XA patent/CN1646670A/zh active Pending
- 2003-04-07 CA CA002480901A patent/CA2480901A1/en not_active Abandoned
- 2003-04-07 EA EA200401356A patent/EA007630B1/ru not_active IP Right Cessation
- 2003-04-07 EP EP03711704A patent/EP1495099A1/de not_active Withdrawn
- 2003-04-07 AU AU2003218521A patent/AU2003218521B2/en not_active Ceased
- 2003-04-07 PL PL03371212A patent/PL371212A1/xx unknown
- 2003-07-04 UA UA20041008270A patent/UA78767C2/uk unknown
-
2004
- 2004-10-05 ZA ZA200408018A patent/ZA200408018B/en unknown
- 2004-10-12 US US10/961,031 patent/US7256301B2/en not_active Expired - Fee Related
- 2004-11-11 HR HR20041057A patent/HRP20041057A2/xx not_active Application Discontinuation
- 2004-11-11 NO NO20044930A patent/NO20044930L/no not_active Application Discontinuation
-
2007
- 2007-04-13 US US11/734,845 patent/US20070185341A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO03087278A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007117096A1 (en) * | 2006-04-07 | 2007-10-18 | Dowell Technology Co., Ltd. | System for alternative fuel with high efficiency of loop reactor and method thereof |
Also Published As
Publication number | Publication date |
---|---|
CA2480901A1 (en) | 2003-10-23 |
RS90004A (en) | 2006-12-15 |
EA007630B1 (ru) | 2006-12-29 |
EA200401356A1 (ru) | 2005-04-28 |
WO2003087278A1 (de) | 2003-10-23 |
US7256301B2 (en) | 2007-08-14 |
CN1646670A (zh) | 2005-07-27 |
MXPA04010015A (es) | 2004-12-13 |
BR0309199A (pt) | 2005-02-09 |
JP2005528472A (ja) | 2005-09-22 |
KR20040101446A (ko) | 2004-12-02 |
AU2003218521B2 (en) | 2009-05-28 |
PL371212A1 (en) | 2005-06-13 |
HRP20041057A2 (en) | 2005-06-30 |
UA78767C2 (en) | 2007-04-25 |
NO20044930L (no) | 2004-11-11 |
AT504727A1 (de) | 2008-07-15 |
US20070185341A1 (en) | 2007-08-09 |
ZA200408018B (en) | 2005-10-05 |
AU2003218521A1 (en) | 2003-10-27 |
US20050065357A1 (en) | 2005-03-24 |
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