Methods for producing alkyl hydroxyalkanoates

Patent metadata

Field	Value
Publication number	US-2016229787-A1
Application number	US-201415029376-A
Country	US
Kind code	A1
Filing date	Oct 17, 2014
Priority date	Oct 17, 2013
Publication date	Aug 11, 2016
Grant date	—

Abstract

Methods and systems for producing alkyl hydroxyalkanoate from hydroxy carboxylic acid recovery bottoms. The methods generally comprise the steps of obtaining a hydroxy carboxylic acid recovery bottom, adding a mono-alcohol to the hydroxy carboxylic acid recovery bottom to obtain a first mixture, heating the first mixture in the presence of a catalyst to form a reaction product, distilling the reaction product, and recovering an alkyl hydroxyalkanoate fraction.

First claim

1 . A method for producing an alkyl hydroxyalkanoate, comprising:
a) obtaining a hydroxyalkanoate containing composition, comprising:
(i) at least 40 percent by weight hydroxyalkanoate equivalents;
(ii) greater than 0 and less than 45 percent by weight free hydroxyalkanoates;
(iii) at least 1 percent by weight saccharide equivalents; and
(iv) less than 15 percent by weight water;
b) mixing a mono-alcohol in a molar ratio of from about 1.1 to 1.0 to about 10.0 to 1.0 of mono-alcohol to hydroxyalkanoate equivalents present in the hydroxyalkanoate containing composition to obtain a first mixture; c) heating the first mixture to form a reaction product; d) distilling the reaction product and recovering an alkyl hydroxyalkanoate fraction comprising:
(i) at least 90 percent by weight alkyl hydroxyalkanoate;
(ii) less than 1 percent by weight hydroxyalkanoic acid;
(iii) less than 1 percent by weight water; and
(iv) less than 0.5 percent by weight saccharide equivalents.

2 . The method of claim 1 , wherein step (d) further comprises separating the reaction product into a first fraction enriched in the mono-alcohol and water, and a second fraction enriched in the alkyl hydroxyalkanoate, wherein the alkyl hydroxyalkanoate fraction is recovered from the second fraction.

3 . The method of claim 1 , wherein step (d) comprises:
a first step to provide a first fraction enriched in water and mono-alcohol and a second fraction enriched in the alkyl hydroxyalkanoate and the saccharide equivalents; and a second step to fractionate the second fraction into a saccharide equivalents enriched fraction, and the alkyl hydroxyalkanoate fraction.

4 - 5 . (canceled)

6 . The method of claim 1 , wherein step (d) comprises:
a first step to provide a first fraction enriched in water, mono-alcohol, and alkyl hydroxyalkanoate and a second fraction enriched in saccharide equivalents; and a second step to fractionate the first fraction into a water and mono-alcohol enriched fraction and the alkyl hydroxyalkanoate fraction.

7 . The method of claim 1 , wherein the first mixture is heated to a temperature of from about 50° C. to about 300° C.

8 - 10 . (canceled)

11 . The method of claim 1 , wherein the pressure in step (e) ranges from 1 atm to 100 atm.

12 - 13 . (canceled)

14 . The method of claim 1 , wherein the hydroxyalkanoate containing composition comprises at least 50 percent by weight of hydroxyalkanoate equivalents.

15 - 16 . (canceled)

17 . The method of claim 1 , wherein the hydroxyalkanoate containing composition comprises between 0.5 and 40 percent free hydroxyalkanoates.

18 - 21 . (canceled)

22 . The method of claim 1 , wherein the hydroxyalkanoate containing composition comprises at least 2 percent by weight saccharide equivalents.

23 - 24 . (canceled)

25 . The method of claim 1 , wherein the hydroxyalkanoate containing composition comprises less than 15 percent by weight water.

26 - 28 . (canceled)

29 . The method of claim 1 , wherein a pressure below atmospheric pressure is utilized during step (d) to recover the alkyl hydroxyalkanoate fraction.

30 - 33 . (canceled)

34 . The method of claim 1 , wherein percent yield of alkyl hydroxyalkanoate from hydroxyalkanoate equivalents is greater than 50%.

35 - 37 . (canceled)

38 . The method of claim 1 , wherein percent yield of alkyl hydroxyalkanoate from hydroxyalkanoate equivalents is greater than 90%.

39 . (canceled)

40 . The method of claim 1 , wherein the hydroxyalkanoate containing composition is selected from the group consisting of 2-carbon hydroxyalkanoates, 3-carbon hydroxyalkanoates, 4-carbon hydroxyalkanoates, 5-carbon hydroxyalkanoates and mixtures thereof.

41 . The method of claim 1 , wherein percent recovery of alkyl hydroxyalkanoate from hydroxyalkanoate equivalents is greater than 50%.

42 - 46 . (canceled)

47 . The method of claim 1 , wherein the alkyl hydroxyalkanoate fraction comprises less than 0.1 by weight saccharide equivalents.

48 . (canceled)

49 . The method of claim 1 , wherein the hydroxyalkanoate is hydroxypropionate.

50 . The method of claim 49 , wherein the hydroxyalkanoate is lactic acid.

51 . (canceled)

52 . The method of claim 1 , wherein the alkyl hydroxyalkanoate is alkyl hydroxypropionate.

54 . The method of claim 1 , wherein the alkyl hydroxyalkanoate is ethyl lactate.

55 - 56 . (canceled)

Assignees

• Cargill Inc

Inventors

• Abraham Timothy Walter
• Duran Anthony Louis
• Edgar Stephen C
• Gokarn Ravi R

Classifications

• C07C67/03 Primary

  by reacting an ester group with a hydroxy group · CPC title

• C07C67/54

  by distillation · CPC title

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title