US2007021578A1PendingUtilityA1

Enzyme catalyzed organosilicon esters and amides

Individually held — no corporate assignee on recordPriority: Aug 16, 2002Filed: Sep 1, 2006Published: Jan 25, 2007

Est. expiryAug 16, 2022(expired)· nominal 20-yr term from priority

Inventors:Kurt Brandstadt Thomas H. Lane Richard A. Gross

C08G 77/38C07F 7/0889C08G 77/388C07F 7/1892C12P 13/02C12P 9/00C07F 7/081C08G 63/6956C12P 7/62C07F 7/0838

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References

Claims

Abstract

Methods for forming organosilicon esters and amides are provided. Additionally, organosilicon esters and amides are provided. The organosilicon esters and amides may be formed by contacting a hydrolase enzyme with an organosilicon reactant and an organic reactant. The enzyme may catalyze the formation of an ester bond between carboxylic acid, ester, or amide functional groups of the organosilicon or organic reactant and alcohol functional groups of the organic or organosilicon reactant. The enzyme may catalyze the formation of an amide bond between carboxylic acid, ester, or amide functional groups of the organosilicon or organic reactant and amine functional groups of the organic or organosilicon reactant.

Claims

exact text as granted — not AI-modified

1 . A method of forming an organosilicon ester, comprising contacting a hydrolase enzyme with an organosilicon reactant and an organic reactant, wherein:
said organosilicon reactant comprises a organosilicon having the formula wherein: each R is independently selected from alkyl, haloalkyl, unsaturated alkyl, aryl, hydroxy, alkoxy, hydrogen, —(OSiR 2 ) x —OSiR 3 , or R′; at least one of R═R′; x is 0 or greater than 0; y is equal to or greater than 3; and R′ is: wherein:
A is a substituted or unsubstituted hydrocarbon substituent, wherein said hydrocarbon may be substituted such that said hydrocarbon comprises a halogen-, ether-, alkoxy-, phenyl-, or unsaturated-functional hydrocarbon and combinations thereof;
R″ is independently carboxylic acid, ester, amide, or alcohol; and
m is 0 or greater than 0;
said organic reactant comprises an organic molecule having at least one carboxylic acid functional group, ester functional group, amide functional group, or alcohol functional group, and combinations thereof; said at least one functional group of said organic reactant comprises carboxylic acid, ester, or amide when R″ is alcohol; said at least one functional group of said organic reactant comprises alcohol when R″ is carboxylic acid, ester, or amide; and said enzyme catalyzes the formation of an ester bond between carboxylic acid, ester, or amide functional groups of said organosilicon reactant or said organic reactant and alcohol functional groups of said organosilicon reactant or said organic reactant to form said organosilicon ester.

2 . The method as claimed in claim 1 wherein x is between 0 and about 250.

3 . The method as claimed in claim 1 wherein A is a C 3 to C 20 hydrocarbon.

4 . The method as claimed in claim 1 wherein y is between about 3 to about 6.

5 . The method as claimed in claim 1 wherein m is between 0 and about 250.

6 . The method as claimed in claim 1 wherein said hydrolase enzyme comprises an esterase, lipase, protease and combinations thereof.

7 . The method as claimed in claim 6 wherein said hydrolase enzyme comprises a lipase.

8 . The method as claimed in claim 7 wherein said lipase comprises Candida antarctica lipase B.

9 . The method as claimed in claim 1 wherein said organic reactant comprises a solid, and wherein said organosilicon reactant comprises a liquid.

10 . The method as claimed in claim 1 wherein said organosilicon reactant comprises a solid, and wherein said organic reactant comprises a liquid.

11 . The method as claimed in claim 1 wherein said organosilicon reactant comprises a liquid, and wherein said organic reactant comprises a liquid.

12 . The method as claimed in claim 1 wherein said organosilicon reactant is selected such that more than one R═R′.

13 . The method as claimed in claim 1 wherein said organic reactant is selected such that said reactant has a plurality of said functional groups.

14 . The method as claimed in claim 13 wherein said plurality of functional groups comprise the same functional group.

15 . The method as claimed in claim 13 herein said plurality of functional groups comprise different functional groups.

16 . The method as claimed in claim 1 wherein said organosilicon reactant is selected such that more than one R═R′, and wherein said organic reactant is selected such that said reactant has a plurality of said functional groups.

17 . The method as claimed in claim 1 wherein said reaction is conducted at a temperature of between about 20° C. to about 100° C.

18 . The method as claimed in claim 1 wherein said reaction is conducted at a temperature of between about 40° C. and about 70° C.

19 . The method as claimed in claim 1 wherein said reaction is conducted under solventless conditions.

20 . The method as claimed in claim 1 wherein said reaction is conducted in a hydrophobic solvent.

21 . A method of forming an organosilicon ester, comprising contacting a hydrolase enzyme with an organosilicon reactant and an organic reactant, wherein:
said organosilicon reactant comprises a organosilicon having the formula wherein: each R is independently selected from alkyl, haloalkyl, unsaturated alkyl, aryl, hydroxy, alkoxy, hydrogen, —(OSiR 2 ) x —OSiR 3 , or R′; at least one of R═R′; x is 0 or greater than 0; y is equal to or greater than 3; and R′ is: wherein:
A is a substituted or unsubstituted hydrocarbon substituent, wherein said hydrocarbon may be substituted such that said hydrocarbon comprises a halogen-, ether-, alkoxy-, phenyl-, or unsaturated-functional hydrocarbon and combinations thereof;
R″ is independently carboxylic acid, ester, amide, or alcohol; and
m is 0 or greater than 0;
said organic reactant comprises an organic molecule having at least one carboxylic acid functional group, ester functional group, amide functional group, or alcohol functional group, and combinations thereof; said at least one functional group of said organic reactant comprises carboxylic acid, ester, or amide when R″ is alcohol; said at least one functional group of said organic reactant comprises alcohol when R″ is carboxylic acid, ester, or amide; and said enzyme catalyzes the formation of an ester bond between carboxylic acid, ester, or amide functional groups of said organosilicon reactant or said organic reactant and alcohol functional groups of said organosilicon reactant or said organic reactant to form said organosilicon ester.

22 . A method of forming an organosilicon amide, comprising contacting a hydrolase enzyme with an organosilicon reactant and an organic reactant, wherein:
said organosilicon reactant comprises a organosilicon having the formula wherein: each R is independently selected from alkyl, haloalkyl, unsaturated alkyl, aryl, hydroxy, alkoxy, hydrogen, —(OSiR 2 ) x —OSiR 3 , or R′; at least one of R═R′; x is 0 or greater than 0; y is equal to or greater than 3; and R′ is: wherein:
A is a substituted or unsubstituted hydrocarbon substituent, wherein said hydrocarbon may be substituted such that said hydrocarbon comprises a halogen-, ether-, alkoxy-, phenyl-, or unsaturated-functional hydrocarbon and combinations thereof;
R″ is independently carboxylic acid, ester, amine, or amide; and
m is 0 or greater than 0;
said organic reactant comprises an organic molecule having at least one carboxylic acid functional group, ester functional group, or amine functional group, or amide functional group, and combinations thereof; said at least one functional group of said organic reactant comprises carboxylic acid, ester, or amide when R″ is amine; said at least one functional group of said organic reactant comprises amine when R″ is carboxylic acid, ester, or amide; and said enzyme catalyzes the formation of an amide bond between carboxylic acid, ester, or amide functional groups of said organosilicon reactant or said organic reactant and amine functional groups of said organosilicon reactant or said organic reactant to form said organosilicon amide.

23 . The method as claimed in claim 22 wherein x is between 0 and about 250.

24 . The method as claimed in claim 22 wherein A is a C 3 to C 20 hydrocarbon.

25 . The method as claimed in claim 22 wherein y is between about 3 to about 6.

26 . The method as claimed in claim 22 wherein m is between 0 and about 250.

27 . The method as claimed in claim 22 wherein said hydrolase enzyme comprises an esterase, lipase, protease and combinations thereof.

28 . The method as claimed in claim 27 wherein said hydrolase enzyme comprises a lipase.

29 . The method as claimed in claim 28 wherein said lipase comprises Candida antarctica lipase B.

30 . The method as claimed in claim 22 wherein said organic reactant comprises a solid, and wherein said organosilicon reactant comprises a liquid.

31 . The method as claimed in claim 22 wherein said organosilicon reactant comprises a solid, and wherein said organic reactant comprises a liquid.

32 . The method as claimed in claim 22 wherein said organosilicon reactant comprises a liquid, and wherein said organic reactant comprises a liquid.

33 . The method as claimed in claim 22 wherein said organosilicon reactant is selected such that more than one R═R′.

34 . The method as claimed in claim 22 wherein said organic reactant is selected such that said reactant has a plurality of said functional groups.

35 . The method as claimed in claim 34 wherein said plurality of functional groups comprise the same functional group.

36 . The method as claimed in claim 34 wherein said plurality of functional groups comprise different functional groups.

37 . The method as claimed in claim 22 wherein said organosilicon reactant is selected such that more than one R═R′, and wherein said organic reactant is selected such that said reactant has a plurality of said functional groups.

38 . The method as claimed in claim 22 wherein said reaction is conducted at a temperature of between about 20° C. to about 100° C.

39 . The method as claimed in claim 22 wherein said reaction is conducted at a temperature of between about 40° C. and about 70° C.

40 . The method as claimed in claim 22 wherein said reaction is conducted under solventless conditions.

41 . The method as claimed in claim 22 wherein said reaction is conducted in a hydrophobic solvent.

42 . A method of forming an organosilicon amide, comprising contacting a hydrolase enzyme with an organosilicon reactant and an organic reactant, wherein:
said organosilicon reactant comprises a organosilicon having the formula wherein: each R is independently selected from alkyl, haloalkyl, unsaturated alkyl, aryl, hydroxy, alkoxy, hydrogen, —(OSiR 2 ) x —OSiR 3 , or R′; at least one of R═R′; x is 0 or greater than 0; y is equal to or greater than 3; and R′ is: wherein:
A is a substituted or unsubstituted hydrocarbon substituent, wherein said hydrocarbon may be substituted such that said hydrocarbon comprises a halogen-, ether-, alkoxy-, phenyl-, or unsaturated-functional hydrocarbon and combinations thereof;
R″ is independently carboxylic acid, ester, amine, or amide; and
m is 0 or greater than 0;
said organic reactant comprises an organic molecule having at least one carboxylic acid functional group, ester functional group, or amine functional group, or amide functional group, and combinations thereof; said at least one functional group of said organic reactant comprises carboxylic acid, ester, or amide when R″ is amine; said at least one functional group of said organic reactant comprises amine when R″ is carboxylic acid, ester, or amide; and said enzyme catalyzes the formation of an amide bond between carboxylic acid, ester, or amide functional groups of said organosilicon reactant or said organic reactant and amine functional groups of said organosilicon reactant or said organic reactant to form said organosilicon amide.

43 . An organosilicon amide comprising a structurally defined compound having the formula:

wherein:
each R 1 is independently selected from alkyl, haloalkyl, unsaturated alkyl, aryl, hydroxy, alkoxy, hydrogen, —(OSiR 1 2 ) x —OSiR 1 3 , or R′″;
at least one of R 1 ═R′″;
x is 0 or greater than 0;
y is equal to or greater than 3; and
R′″ is:

or
wherein:
A is a substituted or unsubstituted hydrocarbon substituent, wherein said hydrocarbon may be substituted such that said hydrocarbon comprises a halogen-, ether-, alkoxy-, phenyl-, or unsaturated-functional hydrocarbon and combinations thereof;
R 2 is an organic compound; and
m is 0 or greater than 0.

44 . The organosilicon amide as claimed in claim 43 wherein x is between 0 and about 250.

45 . The organosilicon amide as claimed in claim 43 wherein A is a C 3 to C 20 hydrocarbon.

46 . The organosilicon amide as claimed in claim 43 wherein y is between about 3 to about 6.

47 . The organosilicon amide as claimed in claim 43 wherein m is between 0 and about 250.

48 . The organosilicon amide as claimed in claim 43 wherein said compound is characterized by a defined molecular weight.

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