EP1569891A2 - Kontinuierliches verfahren zur herstellung von ethyllactat - Google Patents

Kontinuierliches verfahren zur herstellung von ethyllactat

Info

Publication number
EP1569891A2
EP1569891A2 EP03796169A EP03796169A EP1569891A2 EP 1569891 A2 EP1569891 A2 EP 1569891A2 EP 03796169 A EP03796169 A EP 03796169A EP 03796169 A EP03796169 A EP 03796169A EP 1569891 A2 EP1569891 A2 EP 1569891A2
Authority
EP
European Patent Office
Prior art keywords
lactic acid
ethanol
ethyl lactate
mixture
water
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Withdrawn
Application number
EP03796169A
Other languages
English (en)
French (fr)
Inventor
Serge Tretjak
Rémy Teissier
Elie Burtin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema France SA
Original Assignee
Arkema SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Arkema SA filed Critical Arkema SA
Publication of EP1569891A2 publication Critical patent/EP1569891A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • C07C69/68—Lactic acid esters

Definitions

  • the present invention relates to a process for the preparation of ethyl lactate having a purity greater than 97% from lactic acid or a lactic acid composition.
  • Ethyl lactate can be used alone or in combination with other solvents, as agents for cleaning and degreasing in a machine and in a non-aqueous medium of solid surfaces such as metal parts, ceramics, glass, materials plastics which have been soiled with oils or greases for machining and / or their temporary protection.
  • the present invention therefore relates to a continuous process for preparation of ethyl lactate (I) by esterification 'lactic acid [- or a lactic acid composition] using ethanol according to reaction (1 ):
  • this mixture is subjected to a flash separation, at a temperature between 80 ° C and 90 ° C and under a pressure less than or equal to 65 bar, and that, - on the one hand, the flow is subjected overhead comprising ethyl lactate, ethanol and water, to a fractional distillation continuously, at atmospheric pressure, by introducing said flow onto a determined tray of a distillation column;
  • the foot flow is continuously recycled, consisting essentially of unprocessed lactic acid and heavy products, in the esterification reaction medium; and recovering, at the top of the fractional distillation, a mixture of ethanol and water, and, at the bottom of the fractional distillation, an ethyl lactate having a water content at most equal to 0.3% , an ethanol content of less than 0.5% and a purity of more than 94%.
  • the mixture is extracted from the reaction medium when a conversion rate of lactic acid at most equal to 80% has been reached and, preferably, when this conversion rate is between 65% and 75 %.
  • This mixture can be extracted from the reaction medium, agitated by simple overflowing, and then conveyed to a flash separation device.
  • the reaction is carried out in the presence of a soluble or insoluble catalyst in the esterification reaction medium.
  • soluble catalysts examples include H 2 S0 98%, H 3 P0 4 , methanesulfonic acid. Preferably, H 2 S0 4 98% will be used.
  • the catalyst according to the invention is used at molar contents ranging from 0.1% to 4% and, preferably, at contents ranging from 0.2% to 3% relative to the 100% lactic acid used. artwork.
  • the overhead stream leaving the flash separation feeds a fractional distillation column at an appropriate location on said column, preferably located in the lower part of said column. This location will be determined by a person skilled in the art by calculation, taking into account in particular the number of theoretical plates of the column, the reflux rate, the desired fractionation.
  • the distillation is carried out at atmospheric pressure at a column bottom temperature ranging from 152 ° C to 165 ° C.
  • the heads of said distillation comprise ethanol in amounts at most equal to 85% (by weight), water and traces of ethyl lactate.
  • This mixture can be dehydrated and the alcohol, in the form of an azeotrope, can be recycled into the esterification reaction medium.
  • the process according to the present invention applies very particularly to the esterification with ethanol of the lactic acid contained in commercial lactic acid compositions as defined above.
  • lactic acid lactic acid compositions Preferably, 87% by weight lactic acid lactic acid compositions will be used.
  • the ethyl lactate from the bottom of the fractional distillation contains almost neither water nor ethanol, which makes it possible to obtain, after easy purification, a pure ethyl lactate.
  • the method according to the present invention can be implemented in a device as shown in FIG. 1.
  • This device includes:
  • a reactor (1) optionally provided with stirring, with a temperature probe, with lactic acid (2), ethanol (3) and catalyst (4) supplies; - a flash separation column (5) supplied in phase extracted from the reactor (1) by the supply line (6);
  • the distillation column (7) has a diameter of 70 cm and is filled with a Sulzer B X 70 packing. It has 35 theoretical plates. Conduct of the test
  • the ethanol / lactic acid molar ratio is 2.5.
  • the esterification is carried out at 80 ° C. under atmospheric pressure.
  • the progress of the reaction is carried out by assaying lactic acid by CPV.
  • a mixture is continuously extracted from the reactor (1) comprising:
  • This mixture is subjected to flash separation in column (5) at 85 ° C under a pressure of 50 m bar.
  • the head flow including:
  • the operation is carried out at a column bottom temperature of 155 ° C.
  • the head temperature is 77.2 ° C.
  • the reflux rate is fixed at 1.3.
  • a mixture is obtained at the head comprising (by weight) 76% ethanol and 24% water and traces of ethyl lactate ( ⁇ 0.3%).
  • the ethyl lactate comes out with a purity greater than 94.6% and containing less than 1% water and less than 1% ethanol.
  • This crude ethyl lactate is subjected to purification by fractional distillation under reduced pressure.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP03796169A 2002-12-05 2003-12-05 Kontinuierliches verfahren zur herstellung von ethyllactat Withdrawn EP1569891A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0215348 2002-12-05
FR0215348A FR2848209B1 (fr) 2002-12-05 2002-12-05 Procede continu de preparation de lactate d'ethyle
PCT/FR2003/003598 WO2004052825A2 (fr) 2002-12-05 2003-12-05 Procede continu de preparation de lactate d'ethyle

Publications (1)

Publication Number Publication Date
EP1569891A2 true EP1569891A2 (de) 2005-09-07

Family

ID=32320010

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03796169A Withdrawn EP1569891A2 (de) 2002-12-05 2003-12-05 Kontinuierliches verfahren zur herstellung von ethyllactat

Country Status (11)

Country Link
US (1) US20060041165A1 (de)
EP (1) EP1569891A2 (de)
JP (1) JP2006509024A (de)
KR (1) KR100762773B1 (de)
CN (1) CN1720215A (de)
AU (1) AU2003298421B2 (de)
BR (1) BR0317047A (de)
CA (1) CA2508125A1 (de)
FR (1) FR2848209B1 (de)
MX (1) MXPA05005962A (de)
WO (1) WO2004052825A2 (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100427453C (zh) * 2004-08-27 2008-10-22 清华大学 催化精馏法合成乳酸乙酯工艺
US20110160480A1 (en) * 2008-07-30 2011-06-30 Galactic Sa Continuous Process for Obtaining a Lactic Ester
BE1019021A3 (fr) * 2009-07-01 2012-01-10 Galactic Sa Procede de preparation de lactate d'alkyle c1-c4 de grande purete par putrification des lactates d'alkyle c1-c4 bruts.
KR101140649B1 (ko) * 2009-09-30 2012-05-03 한국화학연구원 암모늄락테이트로부터 알킬락테이트를 직접 제조하는 방법
KR101198866B1 (ko) 2010-12-02 2012-11-07 한국화학연구원 고순도 알킬락테이트 및 젖산의 회수 방법
CN102381973B (zh) * 2011-09-19 2014-01-29 南京大学 一种超高纯度（电子级）乳酸酯类产品的生产工艺
EP2842932A4 (de) 2012-04-27 2015-12-23 Xiaogan Esun New Material Co Ltd Verfahren zur kontinuierlichen herstellung eines lactatproduktes mit hoher optischer reinheit und hohem lactatgehalt
US9944586B2 (en) 2013-10-17 2018-04-17 Cargill, Incorporated Methods for producing alkyl hydroxyalkanoates
BR112017000424A2 (pt) * 2014-07-10 2018-01-23 Archer Daniels Midland Co método de recuperação de lactato de etila a partir de um processo de fermentação de ácido láctico
US10239819B2 (en) 2014-10-17 2019-03-26 Cargill, Incorporated Methods for producing an ester of an alpha, beta-unsaturated carboxylic acid
PL229904B1 (pl) 2015-01-08 2018-09-28 Wroclawskie Centrum Badan Eit Spolka Z Ograniczona Odpowiedzialnoscia Sposób otrzymywania estrów kwasu mlekowego i mleczanomlekowego w reakcji alkoholizy poliestru alifatycznego
CN104876819A (zh) * 2015-05-14 2015-09-02 安徽中草香料有限公司 一种乳酸异丙酯的制备方法
CN107032984A (zh) * 2016-02-03 2017-08-11 天津中福工程技术有限公司 一种连续催化精馏制备乳酸乙酯的方法
KR102019037B1 (ko) * 2017-05-26 2019-09-06 지에스칼텍스 주식회사 알킬 카르복실산 에스테르의 제조 방법
KR102151747B1 (ko) * 2018-11-23 2020-09-03 지에스칼텍스 주식회사 알킬 카르복실산 에스테르의 제조 방법 및 알킬 카르복실산 에스테르의 제조 장치
KR102895179B1 (ko) * 2022-02-07 2025-12-05 주식회사 퓨릿 전자급 에틸락테이트 제조장치 및 이를 이용한 전자급 에틸락테이트 제조방법
CN115970595A (zh) * 2022-12-30 2023-04-18 河南金丹乳酸科技股份有限公司 新型连续固定床催化酯化制备高品质乳酸乙酯的系统及其制备工艺
CN119522206A (zh) * 2023-06-22 2025-02-25 普利特有限公司 一种用于制备电子级乳酸乙酯的装置和使用其制备电子级乳酸乙酯的方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2406648A (en) * 1942-12-08 1946-08-27 Sealtest Inc Process of preparing water-soluble alkyl lactates
US2465772A (en) * 1944-02-17 1949-03-29 Nat Dairy Res Lab Inc Preparation of alkyl lactates
DD206373A1 (de) * 1982-03-16 1984-01-25 Joachim Franke Verfahren und vorrichtung zur abtrennung von milchsaeure aus rohloesungen
US5210296A (en) * 1990-11-19 1993-05-11 E. I. Du Pont De Nemours And Company Recovery of lactate esters and lactic acid from fermentation broth
US5723639A (en) * 1995-10-16 1998-03-03 University Of Chicago Esterification of fermentation-derived acids via pervaporation
US6664413B1 (en) * 1998-11-19 2003-12-16 A. E. Staley Manufacturing Co. Process for production of esters

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004052825A2 *

Also Published As

Publication number Publication date
MXPA05005962A (es) 2006-02-08
CA2508125A1 (fr) 2004-06-24
AU2003298421B2 (en) 2008-04-24
BR0317047A (pt) 2005-10-25
KR20050084179A (ko) 2005-08-26
FR2848209A1 (fr) 2004-06-11
AU2003298421A1 (en) 2004-06-30
FR2848209B1 (fr) 2006-10-13
JP2006509024A (ja) 2006-03-16
KR100762773B1 (ko) 2007-10-04
WO2004052825A2 (fr) 2004-06-24
WO2004052825A8 (fr) 2005-09-15
US20060041165A1 (en) 2006-02-23
CN1720215A (zh) 2006-01-11
WO2004052825A3 (fr) 2004-07-15

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