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US 12,516,019 B2Granted
Amphoteric compounds
AssigneeEastman Chemical Company
InventorsNeil Warren Boaz, Stephanie Kay Clendennen, Yuan Zhang, Michael James Fevola, Tobias Johannes Fütterer
Life of this patent
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Abstract
Disclosed are a variety of amphoteric compounds containing a quaternary nitrogen group, a covalently bound counterion, and an ester or amide group. These amphoteric compounds can be advantageously prepared via a chemoenzymatic green process, and exhibit good surfactant properties.
Claims20
A process for preparing a compound having the formula 1:
- wherein
- R is a C3-C24 hydrocarbyl group;
- R1 is a C2-C8 hydrocarbyl group;
- R2 and R3 are each independently a C1-C6 alkyl or alkenyl group;
- at least two of R1, R2, and R3 may be connected with the N+ to form a heterocyclic ring;
- R4 is a C1-C8 hydrocarbyl group;
- X is O or NH;
- and
- Y− is CO2−, SO3−, SO4−, PO3−2, or PO4−2,
- the process comprising:
- (a) contacting an amine or alcohol of formula 2 with an amino acid derivative of formula 3:
- in the presence of an enzyme at conditions effective to form an intermediate of formula 4:
- wherein R, R1, R2, R3, and X are as defined above and R7 is hydrogen or a C1-C4 alkyl group;
- and
- (b) contacting the intermediate of formula 4 with a carboxylate, sulfonate, sulfate, phosphonate, or phosphate alkylating agent at conditions effective to form the compound of formula 1.
12 more elements
A process for preparing a mixture comprising at least two compounds having the formula 1:
- wherein
- R is a C3-C24 hydrocarbyl group;
- R1 is a C2-C8 hydrocarbyl group;
- R2 and R3 are each independently a C1-C6 alkyl or alkenyl group;
- at least two of R1, R2, and R3 may be connected with the N+ to form a heterocyclic ring;
- R4 is a C1-C8 hydrocarbyl group;
- X is O or NH;
- and
- Y− is CO2−, SO3−, SO4−, PO3−2, or PO4−2, 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 amines or alcohols of formula 2 with an amino acid derivative of formula 3:
- in the presence of an enzyme at conditions effective to form at least two intermediates of formula 4:
- wherein
- R, R1, R2, R3, and X are as defined above,
- R7 is hydrogen or a C1-C4 alkyl group,
- the at least two amines or alcohols 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 at least two intermediates of formula 4 with a carboxylate, sulfonate, sulfate, phosphonate, or phosphate alkylating agent at conditions effective to form the mixture of at least two compounds of the formula 1.
17 more elements
Dependencies are inferred from the claim text.