Amphoteric ester sulfonates

Patent metadata

Field	Value
Publication number	US-9943816-B2
Application number	US-201414518505-A
Country	US
Kind code	B2
Filing date	Oct 20, 2014
Priority date	Oct 20, 2014
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

Disclosed are a variety of amphoteric ester sulfonates, including 3-(N,N-dimethyl-cocoylpropylammonio-1-yl)-2-hydroxypropanesulfonate. These amphoteric ester sulfonates can be advantageously prepared in high yield and purity by a two-step chemoenzymatic process, and have excellent surfactant properties.

First claim

We claim:

1. A mixture at least two compounds having the formula 1:

wherein
RCO— is selected from the group consisting of octanoyl, decanoyl, and C 6 to C 20 acyl radicals derived from coconut oil, hydrogenated coconut oil, hydrogenated and/or fractionated coconut oil fatty acids, palm kernel oil, hydrogenated palm kernel oil, or hydrogenated and/or fractionated palm kernel oil fatty acids;
R 1 and R 2 are connected with the N + to form a 3-piperidininum, a 4-piperidinium, a 3-piperidiniummethyl, a 4-piperidiniummethyl, a 3-pyridinum, a 4-pyridiniurn, a 3-pyridiniummethyl, or a 4-pyridiniummethyl group:
R 3 is methyl;
R 4 is 2-hydroxy-1,3-propylene, and

wherein the at least two compounds have at least one different R substituent.

2. A process for preparing a mixture comprising at least two compounds having the formula 1:

wherein
RCO— is selected from the group consisting of octanoyl, decanoyl, and C 6 to C 20 acyl radicals derived from coconut oil, hydrogenated coconut oil, hydrogenated and/or fractionated coconut oil fatty acids, palm kernel oil, hydrogenated palm kernel oil, or hydrogenated andior fractionated palm kernel oil fatty acids:
R 1 and R 2 are connected with the N + to form a 3-piperidininum, a 4-piperidinium, a 3-piperidiniummethyl, a 4-piperidirilurnrnethyl, a 3-pyridinurn, a 4-pyridinium, a 3-pyridiniummethyl, or a 4-pyridiniummethyl group:
R 3 is methyl:
R 4 is 2-hydroxy-1,3-propylene, and

wherein the at least two compounds have at least one different R substituent
the process comprising:
(a) contacting a mixture comprising at least two acids or esters of formula 2 with a dialkylamino-alcohol of formula 3:

in the presence of an enzyme at conditions effective to form at least two intermediate of formula 4:

wherein
R, R 1 , R 2 , and R 3 are as defined above,
R 7 is hydrogen or C 1 -C 6 alkyl,
the at least two acids or esters of the formula 2 have different R substituents, and
the at least two intermediates of the formula 4 have different R substituents; and
(b) contacting the intermediates of the formula 4 with a sulfonate alkylating agent at conditions effective to form the mixture of at least two compounds of the formula 1.

Assignees

• Eastman Chem Co

Inventors

• Boaz Neil Warren
• Boone Matthew Allen
• Lloyd Jennifer Michelle

Classifications

• B01F17/0057 Primary

  Operations & Transport · mapped topic

• C11D1/92

  Sulfobetaines {; Sulfitobetaines} · CPC title

• C07C309/14 Primary

  containing amino groups bound to the carbon skeleton · CPC title

• C12Y301/01

  Carboxylic ester hydrolases (3.1.1) · CPC title

• C12P17/12

  containing a six-membered hetero ring · CPC title