Claims
- 1. A process for preparing a first hydantoin having the formula ##STR13## the process comprising condensing acetone and a second hydantoin having the formula ##STR14## in the presence of (a) a catalyst selected from the group consisting of ammonia or a primary amine having a pK.sub.b between about 3 and about 5, and (b) a polar diluent selected from the group consisting of water or an admixture of water with a lower alkanol having 7 or fewer carbon atoms per molecule; in said reaction mixture the amount of diluent being from about 150-1,000 ml of diluent per mole of the hydantoin and wherein the molar hydantoin:catalyst:ketone ratio is 1:0.1-10:0.5-4.
- 2. The process of claim 1 in which the acetone and the second hydantoin are condensed in the presence of ammonia.
- 3. The process of claim 1 in which the acetone and the second hydantoin are condensed in the presence of the primary amine.
- 4. The process of claim 3 in which the primary amine has at least one primary amino group and at least one secondary amino group per molecule.
- 5. The process of claim 3 in which the primary amine has at least one primary amino group and at least one tertiary amino group per molecule.
- 6. The process of claim 1 in which the amine is monoethanolamine, ethylenediamine, or trimethylenediamine.
- 7. The process of claim 1 in which the second hydantoin is condensed with the acetone in the presence of an admixture of water and a lower alkanol.
- 8. The process of claim 7 in which the lower alkanol is methanol or ethanol.
- 9. A process for preparing a first hydantoin having the formula ##STR15## the process comprising condensing methyl ethyl ketone and a second hydantoin having the formula ##STR16## in the presence of (a) a catalyst selected from the group consisting of ammonia or a primary amine having a pK.sub.b between about 3 and about 5, and (b) a polar diluent selected from the group consisting of water or an admixture of water with a lower alkanol having 7 or fewer carbon atoms per molecule; in said reaction mixture the amount of said diluent being from about 150-1,000 ml of diluent per mole of the hydantoin and wherein the molar hydantoin:catalyst:ketone ratio is 1:0.1-10:0.5-4.
- 10. The process of claim 9 in which the methyl ethyl ketone and the second hydantoin are condensed in the presence of ammonia.
- 11. The process of claim 9 in which the methyl ethyl ketone and the second hydantoin are condensed in the presence of the primary amine.
- 12. The process of claim 11 in which the amine has at least one primary amino group and at least one secondary amino group per molecule.
- 13. The process of claim 11 in which the amine has at least one primary amino group and at least one tertiary amine group per molecule.
- 14. The process of claim 9 in which the amine is monoethanolamine, ethylenediamine, or trimethylenediamine.
- 15. The process of claim 9 in which the second hydantoin is condensed with the methyl ethyl ketone in the presence of an admixture of water and a lower alkanol.
- 16. The process of claim 15 in which the lower alkanol is methanol or ethanol.
- 17. A process for preparing a product hydantoin having the formula ##STR17## the process comprising condensing methyl ethyl ketone and a second hydantoin having the formula ##STR18## in the presence of (a) a catalyst selected from the group consisting of ammonia or a primary amine having a pK.sub.b between about 3 and about 5, and (b) a polar diluent selected from the group consisting of water or an admixture of water with a lower alkanol having 7 or fewer carbon atoms per molecule; in said reaction mixture the amount of said diluent being from about 150-1,000 ml of diluent per mole of the hydantoin and wherein the molar hydantoin:catalyst:ketone ratio is 1:0.1-10:0.5-4.
- 18. The process of claim 17 in which the methyl ethyl ketone and the second hydantoin are condensed in the presence of ammonia.
- 19. The process of claim 17 in which the methyl ethyl ketone and the second hydantoin are condensed in the presence of the primary amine.
- 20. The process of claim 19 in which the primary amine has at least one primary amino group and at least one secondary amino group per molecule.
- 21. The process of claim 19 in which the primary amine has at least one primary amino group and at least one tertiary amino group per molecule.
- 22. The process of claim 17 in which the amine is monoethanolamine, ethylenediamine, or trimethylenediamine.
- 23. The process of claim 17 in which the second hydantoin is condensed with the methyl ethyl ketone in the presence of an admixture of water and a lower alkanol.
- 24. The process of claim 23 in which the lower alkanol is methanol or ethanol.
- 25. A process for preparing a product hydantoin having the formula ##STR19## the product comprising condensing acetone and a second hydantoin having the formula ##STR20## in the presence of (a) a catalyst selected from the group consisting of ammonia or a primary amine having a pK.sub.b between about 3 and about 5, and (b) a polar diluent selected from the group consisting of water or an admixture of water with a lower alkanol having 7 or fewer carbon atoms per molecule; in said reaction mixture the amount of said polar diluent being from about 150-1,000 ml of said diluent per mole of the hydantoin and wherein the molar hydantoin:catalyst:ketone ratio is 1:0.1-10:0.5-4.
- 26. The process of claim 25 in which the acetone and the second hydantoin are condensed in the presence of ammonia.
- 27. The process of claim 25 in which the acetone and the second hydantoin are condensed in the presence of the primary amine.
- 28. The process of claim 27 in which the primary amine has at least one primary amino group and at least one secondary amino group per molecule.
- 29. The process of claim 27 in which the primary amine has at least one primary amino group and at least one tertiary amino group per molecule.
- 30. The process of claim 25 in which the amine is monoethanolamine, ethylenediamine, or trimethylenediamine.
- 31. The process of claim 25 in which the second hydantoin is condensed with the acetone in the presence of an admixture of water and a lower alkanol.
- 32. The process of claim 31 in which the lower alkanol is methanol or ethanol.
Parent Case Info
This is a continuation, of application Ser. No. 730,425 filed Oct. 7, 1976, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
2861079 |
Britton et al. |
Nov 1958 |
|
3798233 |
Akiba et al. |
Mar 1974 |
|
Non-Patent Literature Citations (4)
Entry |
Doyle et al. J. Chem. Soc. (London) 1955, pp. 2265-2273. |
Kirk-Othmer Encyclopedia of Chemical Technology, vol. 11 2nd ed., pp. 144-146. |
Yale Chem. Abst. 1954, vol. 48, columns 1276-1278. |
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Continuations (1)
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Number |
Date |
Country |
Parent |
730425 |
Oct 1976 |
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