Method of making teritiary hindered amines
AssigneeAristech Chemical Corporation
InventorMark R. Rubino
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Abstract
Fully hindered secondary amines, typically tetramethyl piperidine, are reacted with terminally unsaturated electrophilic compounds having at least five carbon atoms to obtain tertiary hindered amines. The reaction is conducted with an excess of secondary amine, preferably in the presence of a specified solvent such as N-methyl pyrrolidinone.
Claims24
Method of making a heterocyclic hindered tertiary amine of the formula ##STR7## comprising reacting (a) a hindered heterocyclic amine of the formula ##STR8## where each R is independently an alkyl group having from one to two carbon atoms, each R.sup.1 is H or CH.sub.3, and Z is H, an alkyl, aryl, or alkaryl group having from 1-8 carbon atoms, --OOCR.sup.2 or ##STR9## R.sup.2 is C.sub.1-8 alkyl, aryl or aralkyl, and n is an integer from 2 to 10, with (b) an electrophilic compound selected from halides of the formula CH.sub.2 .dbd.CH(CH.sub.2).sub.q X where X is Br or I and q is 3-20 or an electrophilic compound of the formula CH.sub.2 .dbd.CH(CH.sub.2).sub.q OSO.sub.2 R.sup.3 where q is as above and R.sup.3 is an alkyl, aryl, or aralkyl group having from one to ten carbon atoms, in the presence of a solvent of the formula (R.sup.4).sub.2 NCOR.sup.8 where R.sup.8 is H, C.sub.1-12 alkyl, aryl or alkaryl or N(R.sup.4).sub.2, each R.sup.1 is independently selected from C.sub.1-12 alkyl, aryl and alkaryl groups and any two R's may be connected in a ring, while maintaining the molar ratio of said heterocyclic amine to said electrophilic compound greater than 2, and recovering said heterocyclic hindered tertiary amine.
Method of making a heterocyclic hindered tertiary amine of the formula ##STR12## comprising reacting (a) a hindered heterocyclic amine of the formula ##STR13## where each R is independently an alkyl group having from one to two carbon atoms, each R.sup.1 is H or CH.sub.3, and Z is a non-nucleophilic group, with (b) an electrophilic compound selected from halides of the formula CH.sub.2 .dbd.CH(CH.sub.2).sub.q X where X is Br or I and q is 3-20 or an electrophilic compound of the formula CH.sub.2 .dbd.CH(CH.sub.2).sub.q OSO.sub.2 R.sup.3 where q is as above and R.sup.3 is an alkyl, aryl, or aralkyl group having from one to ten carbon atoms, in the presence of a solvent of the formula (R.sup.4).sub.2 NCOR.sup.8 where R.sup.8 is H, C.sub.1-12 alkyl, aryl or alkaryl or N(R.sup.4).sub.2, each R.sup.4 is independently selected from C.sub.1-12 alkyl, aryl and alkaryl groups and any two R's may be connected in a ring, while maintaining the molar ratio of said heterocyclic amine to said electrophilic compound greater than 2, and recovering said heterocyclic hindered tertiary amine.
Method of making 1-(10-undecenyl)-2,2,6,6-tetramethylpiperidine comprising reacting 2,2,6,6-tetramethylpiperidine with 11-bromo-1-undecene in a solvent of N-methylpyrrolidinone.
Method of making a compound of the formula ##STR14## comprising reacting a compound of the formula ##STR15## with a compound of the formula CH.sub.2 .dbd.CH(A)X or CH.sub.2 .dbd.CH(A)OSO.sub.2 R.sup.3 in the presence of a solvent of the formula (R.sup.4).sub.2 NCOR.sup.8 where R.sup.8 is H, C.sub.1-12 alkyl, aryl or alkaryl or N(R.sup.4).sub.2, each R.sup.4 is independently selected from C.sub.1-12 alkyl, aryl and alkaryl groups and any two R's may be connected in a ring, and hydrolyzing the reaction product, wherein (A) is (CH.sub.2).sub.3-20, n is an integer from 2 to 10, X is Br or I, and R.sup.3 is an alkyl, aryl, or alkaryl group having from one to twenty carbon atoms.
Dependencies are inferred from the claim text.