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US 9,822,073 B2Granted
Heterocyclic amphoteric compounds
AssigneeEastman Chemical Company
InventorsNeil Warren Boaz, Matthew Allen Boone
Life of this patent
Estimating the term…
Abstract
Disclosed are a variety of amphoteric compounds having a heterocyclic quaternary nitrogen group. The heterocycle includes pyridines, piperidines, and pyrrolidines, and is linked to the hydrophobe via either an amide or an ester linkage. These heterocyclic amphoteric compounds can be advantageously prepared in high yield and purity by a two-step chemoenzymatic process, and have excellent surfactant properties.
Claims28
A compound having the formula 1:
- wherein
- R is a C3-C23 hydrocarbyl group;
- R1 is a C1-C8 hydrocarbyl group selected from C1-C6 alkyl or alkenyl and C3-C8 cycloalkyl;
- HETN is a piperidine group;
- X is O or NH;
- n is 0 or 1;
- and
- m is 1.
5 more elements
A process for preparing a compound having the formula 1:
- wherein
- R is a C3-C23 hydrocarbyl group;
- R1 is a C1-C8 hydrocarbyl group;
- HETN is a piperidine group;
- X is O or NH;
- n is 0 or 1;
- and
- m is 1,
- the process comprising:
- (a) contacting an acid or ester of formula 2 with a heterocyclic alcohol of formula 3 or a heterocyclic amine of formula 4:
- in the presence of an enzyme at conditions effective to form an intermediate of formula 5:
- wherein
- R, R1, X, HETN, and n are as defined above,
- R4 is hydrogen or a C1-C6 alkyl group, and
- p is 1;
- and
- (b) contacting the intermediate of formula 5 with an acetic acid alkylating agent at conditions effective to form the compound of formula 1.
14 more elements
Dependencies are inferred from the claim text.