Chelating agents for non-aqueous systems

Claim 2

A compound having the formula ##STR9## wherein R is an alkyl group having from 1 to 15 carbon atoms; R' is selected from the group H--, a lower alkyl group, HO--CH 2 --, CH 3 CH(OH)--, HSCH 2 --, CH 3 --SCH 2 CH 2 --, H 2 NCOCH 2 --, H 2 NCOCH 2 CH 2 --, HOOCCH 2 --, HOOCCH 2 CH 2 --, and ##STR10## M is selected from the group consisting of H+, an alkali metal ion, NH 4 +, and an aminium ion; and n is an integer from 1 to 6.

Claim 3

A compound according to claim 1 in which R is an alkyl group having from 4 to 15 carbon atoms.

Claim 4

A compound according to claim 1 in which R is selected from the group t-butyl, t-amyl, nonyl, and dodecyl.

Claim 5

A compound according to claim 1 in which R' is selected from the group H--, CH 3 --, (CH 3 ) 2 CH--, CH 3 S--CH 2 CH 2 --, and HOOCCH 2 --.

Claim 6

A compound according to claim 1 in which R is a nonyl group.

Claim 7

A compound according to claim 1 in which R' is H.

Claim 8

A compound according to claim 1 in which M is Na+.

Claim 9

A compound according to claim 1 in which n is 1.

Claim 10

A compound according to claim 1 in which R is a nonyl R' is H, M is Na+, and n is 1.

Claim 11

A methanol solution of a compound according to claim 1 wherein R is an alkyl group having from 1 to 3 carbon atoms.

Claim 12

A process for preparing a compound having the formula: ##STR11## wherein R is an alkyl group having from 1 to 15 carbon atoms; R' is selected from the group H--, a lower alkyl group, HO--CH 2 --, CH 3 CH(OH)--, HSCH 2 --, CH 3 --SCH 2 CH 2 --, H 2 NCOCH 2 --, H 2 NCOCH 2 CH 2 --, HOOCCH 2 --, HOOCCH 2 CH 2 --, and ##STR12## M is selected from the group consisting of H+, an alkali metal ion, NH 4 +, and an aminium ion; and n is an integer from 1 to 6; said process comprising (i) forming a first mixture by adding about 2 molar equivalents of an aqueous solution of formaldehyde to about 1 molar equivalent of an aqueous solution of an amino acid having the general formula NH 2 CHR'COOM over a time period of 0.5-2 hours and at a temperature of 20°-50° C. while maintaining the mixture at a pH of 7.5-8; (ii) forming a second mixture by admixing the first mixture with a sufficient amount of methanol to permit dissolution of a phenol of the general formula ##STR13## while maintaining the pH of the second mixture at 7.5-8.0 (iii) forming a third mixture by adding to the second mixture 1.1 to 1.5 molar equivalents of a methanol solution of a phenol of the general formula ##STR14## over a period of 0.5-2 hours at a temperature of 30°-80° C. while maintaining the pH at 7.5-8.0; (iv) heating the third mixture at reflux for a period of 5-7 hours; and (v) allowing the third mixture to cool, followed by separation and recovery of said compound.

Claim 13

A process for preparing a compound having the formula: ##STR11## wherein R is an alkyl group having from 1 to 15 carbon atoms; R' is selected from the group H--, a lower alkyl group, HO--CH 2 --, CH 3 CH(OH)--, HSCH 2 --, CH 3 --SCH 2 CH 2 --, H 2 NCOCH 2 --, H 2 NCOCH 2 CH 2 --, HOOCCH 2 --, HOOCCH 2 CH 2 --, and ##STR12## M is selected from the group consisting of H+, an alkali metal ion, NH 4 +, and an aminium ion; and n is an integer from 1 to 6; said process comprising (i) forming a first mixture by adding about 2 molar equivalents of an aqueous solution of formaldehyde to about 1 molar equivalent of an aqueous solution of an amino acid having the general formula NH 2 CHR'COOM over a time period of 0.5-2 hours and at a temperature of 20°-50° C. while maintaining the mixture at a pH of 7.5-8; (ii) forming a second mixture by admixing the first mixture with a sufficient amount of methanol to permit dissolution of a phenol of the general formula ##STR13## while maintaining the pH of the second mixture at 7.5-8.0 (iii) forming a third mixture by adding to the second mixture 1.1 to 1.5 molar equivalents of a methanol solution of a phenol of the general formula ##STR14## over a period of 0.5-2 hours at a temperature of 30°-80° C. while maintaining the pH at 7.5-8.0; (iv) heating the third mixture at reflux for a period of 5-7 hours; and (v) allowing the third mixture to cool, followed by separation and recovery of said compound.

Claim 14

The process according to claim 11 in which R is an alkyl group having from 4 to 15 carbon atoms.

Claim 15

The process according to claim 11 in which R is selected from the group t-butyl, t-amyl, nonyl, and dodecyl.

Claim 16

The process according to claim 11 in which R' is selected from the group H--, CH 3 --, (CH 3 ) 2 CH--, CH 3 S--CH 2 CH 2 --, and HOOCCH 2 --.

Claim 17

The process according to claim 11 wherein R is a nonyl group.

Claim 18

The process according to claim 11 in which R' is H.

Claim 19

The process according to claim 11 in which M is Na+.

Claim 20

The process according to claim 11 in which n is 1.

Claim 21

The process according to claim 11 in which R is a nonyl group, R' is H, M is Na+, and n is 1.

Claim 22

The process according to claim 11 in which R is an alkyl group having from 1 to 3 carbon atoms and in which the desired product is soluble in methanol.