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EP2121561A1 - Kontinuierliches verfahren zur herstellung von alkylestern aus milchsäure und aliphatischem alkohol - Google Patents

Kontinuierliches verfahren zur herstellung von alkylestern aus milchsäure und aliphatischem alkohol

Info

Publication number
EP2121561A1
EP2121561A1 EP07702546A EP07702546A EP2121561A1 EP 2121561 A1 EP2121561 A1 EP 2121561A1 EP 07702546 A EP07702546 A EP 07702546A EP 07702546 A EP07702546 A EP 07702546A EP 2121561 A1 EP2121561 A1 EP 2121561A1
Authority
EP
European Patent Office
Prior art keywords
lactic acid
process according
alcohol
alkyl esters
moles
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Withdrawn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
EP07702546A
Other languages
English (en)
French (fr)
Inventor
Valeriy Fedorovich Shvets
Juriy Pavlovich Suchkov
Roman Anatolievich Kozlovskiy
Ivan Anatolievich Kozlovskiy
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.)
Nordbiochem Oue
Original Assignee
Nordbiochem Oue
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 Nordbiochem Oue filed Critical Nordbiochem Oue
Publication of EP2121561A1 publication Critical patent/EP2121561A1/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Withdrawn legal-status Critical Current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
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • 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

Definitions

  • the present invention relates to a continuous process for the preparation of alkyl ester hydroxycarboxyiic acids.
  • the present invention particularly relates to a catalytic process for the conversion of mixtures containing free lactic acid and/or dimers and/or highpolymers of lactic acids and its alkyl esters to alkyl esters of aliphatic alcohols by contact of its mixtures with aliphatic alcohols.
  • lactic acid esters can advantageously be taken advantage of in numerous fields of activity, such as the metal industries, the automobile and aviation industries, the paint and ink industries, the resin and varnish industries, the pharmaceutical and cosmetological industries, and the semiconductor industries.
  • esters of lactic acid remains to this day a product which is still not manufactured and used industrially to any great extent, in particular with regard to chlorinated solvents, glycols or glycol ethers, because of their price, which in two - four times above than the price of the main commercially accessible glycol ethers.
  • US 5264617 (DU PONT) 23.11.1993 reports synthesis of lactic acid esters in the presence of a catalyst (p-toluene sulfonic acid) by depolymerization of polylactide by heating with a Ci to Ce alkyl alcohol in an amount of 1-3 mole of alcohol per hydroxy acid equivalent. Yield of lactic acid esters is 87%.
  • a catalyst p-toluene sulfonic acid
  • a continues process for manufacture of ethyl lactate by catalytic rectifying method is described in a patent CN 1613842 (UNIV TSINGHUA) 11.05.2005 . It is carried out by lactic acid catalytic reacting with alcohol (3-5 mole of ethanol per mole of lactic acid) in catalytic section of catalytic rectifying tower with highly acid ionic exchanging resin as a catalyst, generating ethyl lactate, vaporizing alcohol in reacting solution and generated water, enriching in rectifying section of rectifying tower, alcohol and water condensing in condenser, one part returning feed storing tank, another part back flowing into catalytic rectifying tower.
  • alcohol 3-5 mole of ethanol per mole of lactic acid
  • the main object of the present invention is to provide a process continues esterification of lactic acid, dimers, oligomers, polymers and its esters for the preparation of alkyl esters.
  • One embodiment of the present invention is shown in Fig. 1, and includes reactor I, mixer IV, vessel III and throttling device II.
  • the reaction may be catalyzed by one or more of a number of methods.
  • a heterogeneous catalyst may be retained at tubes of reactor I.
  • Homogeneous catalyst may be loaded in the vessel III and circulates on a line: vessel III - mixer IV - reactor I - vessel III.
  • the reaction can carry out in the absence of the catalyst, but in this case a high temperature is required.
  • the mixture of free lactic acid, oligomers and/or polymers, its alkyl esters, alcohol and homogeneous catalyst is loaded into a vessel III and circulated via (4) through heated reactor I approximately within 3-7 hours.
  • a vaporous of crude ester continuously is drawn off from the vessel III according to a level of a liquid phase at a vessel III.
  • a vaporous of crude ester is condensed and to distill.
  • the crude esters are essentially free from water and alcohol.
  • FIG. 2 Other embodiment of the present invention is shown in FIG. 2, and includes reactor I, mixers IV and VII, column Il and V, and vessel III.
  • a heterogeneous catalyst may be retained at tubes of reactor I.
  • Homogeneous catalyst may be loaded into the still of column Il and circulates on a line: column Il - mixer IV - vessel III - (reactor I) - column V - mixer IV - column II.
  • a vaporous of crude ester continuously is drawn off from the vessel Ul according to a level of a liquid phase at the vessel III, is condensed and is analyzed by GLC analysis.
  • the condensate (flow 3, approximate 14.6 g/h) has the following composition, %wt: Methyl Lactate -96.3; Methanol - 1.9; Water- 1.8.
  • the yield of methyl lactate is 99.8%.
  • the tubes of reactor I was charged with of the heterogeneous catalyst (Nafion-H). 200 g oligomers of lactic acid with the mean degree of polymerization (MDP) equal to 10, 65 g butanol, 60 g butyl lactate and 1.0g tin(ll) 2-ethylhexanoate are loaded into the vessel III. A resulting mixture circulated via (4) (approximate 86.7 g/h) through the heated reactor I (145 0 C) approximately within 7 hours.
  • MDP mean degree of polymerization
  • the condensate of column 5 (approximate 19.8 g/h) has the following composition, %wt.: Butyl Lactate -95.5; Butanol - 3.0; Water -1.5. The yield of Butyl lactate is 99.5%.
  • the condensate of column 2 (approximate 2.3 g/h) has the following composition %wt.: Lactic acid - 2; Butanol - 2; Butyl Lactate - 1 ; Water - 95.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP07702546A 2007-02-12 2007-02-12 Kontinuierliches verfahren zur herstellung von alkylestern aus milchsäure und aliphatischem alkohol Withdrawn EP2121561A1 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EE2007/000002 WO2008098581A1 (en) 2007-02-12 2007-02-12 A continuous process for the preparation of alkyl esters of lactic acid and aliphatic alcohols

Publications (1)

Publication Number Publication Date
EP2121561A1 true EP2121561A1 (de) 2009-11-25

Family

ID=38567011

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07702546A Withdrawn EP2121561A1 (de) 2007-02-12 2007-02-12 Kontinuierliches verfahren zur herstellung von alkylestern aus milchsäure und aliphatischem alkohol

Country Status (2)

Country Link
EP (1) EP2121561A1 (de)
WO (1) WO2008098581A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL3526190T3 (pl) * 2016-10-12 2022-02-14 Basf Se Sposób wytwarzania estrów kwasów hydroksyalkilokarboksylowych
CN108084021A (zh) * 2017-12-27 2018-05-29 上海应用技术大学 一种棕榈酸异辛酯的制备方法
CN111205180A (zh) * 2020-02-13 2020-05-29 美国吉尔斯股份有限公司 一种羟基酸烷基酯的制备方法及其应用
CN111943849B (zh) * 2020-08-15 2023-08-29 天津大学 高效节能型乳酸乙酯反应精馏生产方法及装置

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2802923B1 (fr) * 1999-12-28 2002-03-08 Roquette Freres Procede de preparation d'une composition d'ester d'acide lactique et son utilisation en tant que solvant
FR2848208B1 (fr) * 2002-12-05 2005-01-14 Atofina Procede continu de preparation de lactate d'ethyle

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008098581A1 *

Also Published As

Publication number Publication date
WO2008098581A1 (en) 2008-08-21

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