Compositions including an alkyl 3-hydroxybutyrate

Patent metadata

Field	Value
Publication number	US-9388114-B2
Application number	US-201313957657-A
Country	US
Kind code	B2
Filing date	Aug 2, 2013
Priority date	Aug 2, 2013
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

Compositions comprising an alkyl 3-hydroxybutyrate and one or more additional components are provided. The compositions of the present invention may include at least one alkyl 3-hydroxybutyrate having at least 3 and not more than 5 carbon atoms, along with one or more additional components including, for example, alkyl butyrates, alkyl acetates, alkyl alcohols, and dimers and/or trimers of the alkyl 3-hydroxybutyrate. Such compositions may be products of, for example, the hydrogenation of an acetoacetate-containing composition.

First claim

We claim:

1. A composition comprising:
(a) at least one alkyl 3-hydroxybutyrate defined by formula (I):

an alkyl butyrate defined by formula (II):

(c) a dimer and/or trimer of said alkyl 3-hydroxybutyrate; and
(d) an alkyl acetate defined by formula (III):

wherein R1 is an alkyl group selected from the group consisting of isopropyl, n-propyl, isobutyl, n-butyl, 2-butyl (sec-butyl), isopentyl, pentyl, and 2,2-dimethylpropyl, wherein R1 is the same for each of the components defined by formulas (I), (II), and (III),
wherein the total amount of said alkyl butyrate and said alkyl acetate is in the range of from about 50 to about 1500 parts per million by weight (ppmw), based on the total weight of said composition, and
wherein the total amount of said dimer and/or trimer of said alkyl 3-hydroxybutyrate is in the range of from about 50 ppmw to about 1200 ppmw, based on the total weight of said composition.

2. The composition of claim 1 , wherein R1 is an alkyl group selected from the group consisting of isobutyl, n-butyl, and 2-butyl.

3. A composition comprising:
(a) at least one alkyl 3-hydroxybutyrate defined by formula (I):

(b) one or more additional components selected from the group consisting of—
(i) an alkyl butyrate defined by formula (II):

(ii) a dimer and/or trimer of said alkyl 3-hydroxybutyrate; and
(iii) an alkyl acetate defined by formula (III):

wherein R1 is an alkyl group selected from the group consisting of isopropyl, n-propyl, isobutyl, n-butyl, 2-butyl (sec-butyl), isopentyl, pentyl, and 2,2-dimethylpropyl, wherein R1 is the same for each of the components defined by formulas (I), (II), and (III), and
further comprising N,N-diethyl-3-hydroxybutanamide in an amount in the range of from about 200 ppmw to about 2000 ppmw, based on the total weight of said composition.

4. A composition comprising:
(a) at least one alkyl 3-hydroxybutyrate defined by formula (I):

and
(b) at least one alkyl butyrate defined by formula (II):

wherein R1 is an alkyl group having least three and not more than five carbon atoms;
(c) a dimer and/or trimer of said alkyl 3-hydroxybutyrate; and
(d) an alkyl acetate defined by formula (III):

wherein R1 is the same for each of the components defined by formulas (I), (II), and (III), and
wherein said alkyl 3-hydroxybutyrate is present in said composition in an amount in the range of from about 65 to about 99 weight percent, wherein said alkyl butyrate is present in said composition in an amount in the range of from about 50 ppmw to about 0.1 weight percent, wherein said dimer and/or trimer of said alkyl 3-hydroxybutyrate is present in said composition in an amount in the range of from about 50 to about 1200 ppmw, wherein said alkyl acetate is present in said composition in an amount in the range of from about 50 to about 1000 ppmw, based on the total weight of said composition.

5. The composition of claim 4 , wherein said composition comprises not more than about 1 weight percent of components other than said alkyl 3-hydroxybutyrate, said alkyl butyrate, said dimer and/or trimer of said alkyl 3-hydroxybutyrate and said alkyl acetate.

6. The composition of claim 4 , wherein R1 is an alkyl group selected from the group consisting of i-butyl, n-butyl, and 2-butyl.

7. A composition comprising:
(a) at least one alkyl 3-hydroxybutyrate defined by formula (I):

(b) at least one alkyl butyrate defined by formula (II):

wherein R1 is an alkyl group having least three and not more than five carbon atoms;
(c) a dimer and/or trimer of said alkyl 3-hydroxybutyrate;
(d) an alkyl acetate defined by formula (III):

wherein R1 is the same for each of the components defined by formulas (I), (II), and (III), and
one or more further components selected from the group consisting of—
(e) a first alkyl alcohol defined by formula (IV):
R1-OH  (IV);

(f) a second alkyl alcohol defined by formula (V):
R2-OH  (V);

(g) a second alkyl 3-hydroxybutyrate defined by formula (VI):

and
(h) an alkyl 3-hydroxy-2-methylbutyrate defined by formula (VII):

wherein R2 is an alkyl group having at least 2 and not more than 4 carbon atoms, wherein R1 in formulas (IV) and (VII) is the same as R1 in formulas (I), (II), and (III) and R2 is the same for each compound in formulas (V) and (VI),
wherein said alkyl 3-hydroxybutyrate is present in said composition in an amount in the range of from about 65 to about 99 weight percent, wherein said alkyl butyrate is present in said composition in an amount in the range of from about 50 ppmw to about 0.1 weight percent, wherein said dimer and/or trimer of said alkyl 3-hydroxybutyrate is present in said composition in an amount in the range of from about 50 to about 1200 ppmw, wherein said alkyl acetate is present in said composition in an amount in the range of from about 50 to about 1000 ppmw, wherein the total amount of said first alcohol, said second alcohol, said second alkyl 3-hydroxybutyrate, and said alkyl 3-hydroxy-2-methylbutyrate is not more than about 0.1 weight percent, based on the total weight of said composition.

8. The composition of claim 7 , wherein said composition comprises said first alcohol in an amount in the range of from about 3500 to about 10,000 ppmw, wherein said second alcohol is present in said composition in an amount in the range of from about 50 to about 1200 ppmw, wherein said second alkyl 3-hydroxybutyrate is present in said composition in an amount in the range of from about 50 to about 1000 ppmw, wherein said alkyl 3-hydroxy-2-methylbutyrate is present in said composition in an amount in the range of from about 50 to about 1200 ppmw, based on the total weight of said composition.

9. A composition comprising:
(a) at least one alkyl 3-hydroxybutyrate defined by formula (I):

and
(b) at least one alkyl butyrate defined by formula (II):

wherein R1 is an alkyl g

Assignees

• Eastman Chem Co

Inventors

• Weakley Garry Kenneth
• Kelly Charles Everette
• Golob Therese T

Classifications

• C11D3/2093 Primary

  Esters; Carbonates · CPC title

• C23G5/06

  using emulsions · CPC title

• C09D7/001

  Chemistry & Metallurgy · mapped topic

• C07C31/10

  containing three carbon atoms · CPC title

• C07C31/12

  containing four carbon atoms · CPC title