Claims
- 1. 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.sub.2 --, CH.sub.3 CH(OH)--, HSCH.sub.2 --, CH.sub.3 --SCH.sub.2 CH.sub.2 --, H.sub.2 NCOCH.sub.2 --, H.sub.2 NCOCH.sub.2 CH.sub.2 --, HOOCCH.sub.2 --, HOOCCH.sub.2 CH.sub.2 --, and ##STR10## M is selected from the group consisting of H+, an alkali metal ion, NH.sub.4 +, and an aminium ion; and
- n is an integer from 1 to 6.
- 2. A compound according to claim 1 in which R is an alkyl group having from 4 to 15 carbon atoms.
- 3. A compound according to claim 1 in which R is selected from the group t-butyl, t-amyl, nonyl, and dodecyl.
- 4. A compound according to claim 1 in which R' is selected from the group H--, CH.sub.3 --, (CH.sub.3).sub.2 CH--, CH.sub.3 S--CH.sub.2 CH.sub.2 --, and HOOCCH.sub.2 --.
- 5. A compound according to claim 1 in which R is a nonyl group.
- 6. A compound according to claim 1 in which R' is H.
- 7. A compound according to claim 1 in which M is Na+.
- 8. A compound according to claim 1 in which n is 1.
- 9. A compound according to claim 1 in which R is a nonyl R' is H, M is Na+, and n is 1.
- 10. A methanol solution of a compound according to claim 1 wherein R is an alkyl group having from 1 to 3 carbon atoms.
- 11. 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.sub.2 --, CH.sub.3 CH(OH)--, HSCH.sub.2 --, CH.sub.3 --SCH.sub.2 CH.sub.2 --, H.sub.2 NCOCH.sub.2 --, H.sub.2 NCOCH.sub.2 CH.sub.2 --, HOOCCH.sub.2 --, HOOCCH.sub.2 CH.sub.2 --, and ##STR12## M is selected from the group consisting of H+, an alkali metal ion, NH.sub.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.sub.2 CHR'COOM over a time period of 0.5-2 hours and at a temperature of 20.degree.-50.degree. 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.degree.-80.degree. 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.
- 12. The process according to claim 11 in which R is an alkyl group having from 4 to 15 carbon atoms.
- 13. The process according to claim 11 in which R is selected from the group t-butyl, t-amyl, nonyl, and dodecyl.
- 14. The process according to claim 11 in which R' is selected from the group H--, CH.sub.3 --, (CH.sub.3).sub.2 CH--, CH.sub.3 S--CH.sub.2 CH.sub.2 --, and HOOCCH.sub.2 --.
- 15. The process according to claim 11 wherein R is a nonyl group.
- 16. The process according to claim 11 in which R' is H.
- 17. The process according to claim 11 in which M is Na+.
- 18. The process according to claim 11 in which n is 1.
- 19. The process according to claim 11 in which R is a nonyl group, R' is H, M is Na+, and n is 1.
- 20. 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.
Parent Case Info
This is a continuation-in-part of Ser. No. 193,292 filed Oct. 2, 1980, now abandoned.
US Referenced Citations (17)
Foreign Referenced Citations (1)
Number |
Date |
Country |
2353642 |
May 1975 |
DEX |
Non-Patent Literature Citations (3)
Entry |
Morris et al., "Organic Chem.", 2nd Eden., p. 52, (1966). |
Pasto, "Organic Structure Determination", pp. 321-322 (1965). |
Walker, "Formaldehyde", 3rd Eden., p. 308, Reinhold Publ. Corp. |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
193292 |
Oct 1980 |
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