Claims
- 1. A process for the production of 2-alkyl-or alkenyl-2-oxazolines corresponding to formula I ##STR2## in which R.sup.1 is a hydroxy-, dihydroxy- or hydroxy, C.sub.1 -C.sub.2 -alkoxy-substituted hydrocarbon radical having 7 to 21 carbon atoms in the carbon chain, comprising condensing in the liquid phase a C.sub.8 -C.sub.22 fatty acid or ester thereof with a C.sub.1 -C.sub.4 monoalkanol and 2- aminoethanol or an ethanolamide of said fatty acid in the presence of a titanium or zirconium catalyst, said catalyst being selected from the group consisting of (1) a titanium or zirconium compound corresponding to formula II
- (M(OR.sup.2).sub.4 (II)
- in which M represents tetravalent titanium or zirconium, and R.sup.2 is an acyl group having 2 to 10 carbon atoms, a 2-aminoethyleneoxy group, or a residue of a beta-diketone in the enol form corresponding to formula III
- R.sup.3 --C.dbd.CH.sub.2 --CO--R.sup.4 (III)
- wherein R.sup.3 and R.sup.4 are the same or different and represent a radical consisting of a C.sub.1 -C.sub.4 alkyl group, (2) titanyl acetylacetonate, and (3) a condensation product of titanium (IV) or zirconium (IV) tetraalkoxylate corresponding to formula II, in which M and R.sup.2 are as defined above, with a polyfunctional alkanol having 3 to 12 carbon atoms and 2 to 6 hydroxy groups, removing the alcohol or water of reaction formed, and isolating the 2-alkyl- or 2-alkenyl-2-oxazoline obtained.
- 2. A process as in claim 1 wherein said catalyst comprises tetra(aminoethyl) titanate or zirconate.
- 3. A process as in claim 1 herein said catalyst comprises a titanium acetylacetonate corresponding to formula IV
- (R.sup.5 O).sub.m M(ACA).sub.n (IV)
- in which R.sup.5 is a C.sub.1 -C.sub.4 alkyl group, ACA is an acetylacetonate group and m=0 and n=4, or m=2 and n=2.
- 4. A process as in claim 1 wherein said catalyst comprises a polycondensation product of an ester of titanic acid with a C.sub.2 -C.sub.10 monoalkanol and pentaerythritol.
- 5. A process as in claim 1 wherein said catalyst is used in a quantity of from about 0.1 to about 3 mol-%, based on said fatty acid ethanolamide.
- 6. A process as in claim 1 wherein said condensing step is carried out at about 150.degree. to about 270.degree. C.
- 7. A process as in claim 1 carried out in vacuo.
- 8. A process as in claim 1 wherein the alcohol or water of reaction formed is distilled off together with the 2-alkyl- or alkenyl-substituted 2-oxazolines and is separated therefrom either subsequently or at the same time or is removed by azeotropic distillation before the distillation of said oxazolines.
- 9. A process as in claim 1 wherein in a first reaction stage, a fatty acid or fatty acid ester corresponding to formula V
- R.sup.1 --COOR.sup.6 (V)
- in which R.sup.1 is as defined above and R.sup.6 is hydrogen or a C.sub.1 -C.sub.4 alkyl group, is reacted with ethanolamine at elevated temperature to form the fatty acid ethanolamide with removal of the alcohol or water of reaction and the reaction mixture is left to react in a second reaction stage in which the reaction temperature is further increased.
- 10. A process as in claim 9 wherein said ethanolamine is present in an excess of about 50 to about 400 mol-%, based on the fatty acid ester used.
- 11. A process as in claim 9 wherein unreacted or excess ethanolamine is removed from the reaction mixture before the second reaction stage.
- 12. A process as in claim 9 wherein a reaction temperature of about 100.degree. to about 150.degree. C. is used in the first reaction stage.
- 13. A process as in claim 9 wherein a reaction temperature of about 150.degree. to about 270.degree. C. is used in the second reaction stage.
- 14. A process as in claim 9 wherein said catalyst comprises a tetra(aminoethyl) titanate or zirconate.
- 15. A process as in claim 9 wherein said catalyst comprises a mixed anhydride of titanic acid with a monocarboxylic acid.
- 16. A process as in claim 9 wherein said catalyst comprises a titanium acetylacetonate corresponding to formula IV
- (R.sup.5 O).sub.m (M(ACA).sub.n (IV)
- in which R.sup.5, ACA, m and n are as defined in claim 3.
- 17. A process as in claim 9 wherein said catalyst comprises a polycondensation product of an ester of titanic acid with a C.sub.2 -C.sub.10 monoalkanol and pentaerythritol.
- 18. A process as in claim 9 wherein said catalyst is present in a quantity of 0.01 to 3 mol-%, based on said fatty acid or fatty acid ester.
- 19. A process as in claim 9 carried out in vacuo.
- 20. A process as in claim 9 wherein the alcohol or water of reaction formed in the second reaction stage is distilled off together with the 2-alkyl- or simultaneously removed or is removed by azeotropic distillation before the distillation of 2-oxazolines.
- 21. A process as in claim 9 wherein the first and second stages of the reaction are carried out as a one-pot process.
Priority Claims (2)
Number |
Date |
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Kind |
3738197 |
Nov 1987 |
DEX |
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3824982 |
Jul 1988 |
DEX |
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Parent Case Info
This application is a continuation of application Ser. No. 07/481,744, filed Feb. 14, 1990, now abandoned, which is a continuation of application Ser. No. 07/269,271, filed Nov. 9, 1988, now abandoned.
US Referenced Citations (8)
Foreign Referenced Citations (4)
Number |
Date |
Country |
0105944 |
Apr 1984 |
EPX |
0164219 |
Dec 1985 |
EPX |
0033752 |
Apr 1987 |
EPX |
0019661 |
Feb 1977 |
JPX |
Non-Patent Literature Citations (3)
Entry |
Chem. Abst. 87:135352h, 2-Oxazolines and 5,6-dihydro-4H-1,3 oxazine, Japan. |
Chem. Abst. 87:135353j, 2-Oxazoline and 5,6-dihydro-4H-1,3 oxazine, Japan. |
Chem. Rev. 71, 485 ff (1971). |
Continuations (2)
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Parent |
481744 |
Feb 1990 |
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Parent |
269271 |
Nov 1988 |
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