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US 5,288,910 AGranted
Palladium catalyzed addition of amines to 3,4-epoxy-1-butene
AssigneeEastman Kodak Company
InventorYann Hung
Life of this patent
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Abstract
4-amino-2-buten-1-ol is formed by the regioselective addition of primary amines or ammonia to 3,4-epoxy-1-butene. A quantity of a the primary amine or ammonia is reacted with 3,4-epoxy-1-butene in a reaction medium in the presence of a catalyst. The reaction medium is a liquid which has an E.sub.T (30) no less than about 32. The catalyst is a complex of palladium and phosphine ligands.
Claims21
A process for forming 4-amino-2-buten-1-ol, comprising the steps of:
- providing a quantity of 3,4-epoxy-1-butene;
- providing a quantity of primary amine or ammonia;
- and
- reacting said quantity of 3,4-epoxy-1-butene with said quantity of primary amine or ammonia in a reaction medium and in the presence of a catalyst, wherein said catalyst is a complex of palladium and phosphine ligands and said reaction medium is a liquid having an E.sub.T (30) no less than about 32.
1 more element
A process for forming 4-amino-2-buten-1-ol, comprising the steps of:
- providing a quantity of 3,4-epoxy-1-butene;
- providing a quantity of a primary amine selected from the group consisting of methylamine and cyclohexylamine;
- and
- reacting said quantity of 3,4-epoxy-1-butene with said quantity of methylamine in a reaction medium and in the presence of a catalyst, wherein said catalyst is selected from the group consisting of:
- Pd(PR.sub.1 R.sub.2 R.sub.3).sub.2 X.sub.2 ;
- Pd(R.sub.4 R.sub.5 P(V).sub.b ZR.sub.6 R.sub.7)X.sub.2 ;
- [(.eta..sup.3 -CH(R.sub.8)C(R.sub.9)CH(R.sub.10))Pd(PR.sub.1 R.sub.2 R.sub.3).sub.2 ]X;
- [(.eta..sup.3 -CH(R.sub.8)C(R.sub.9)CH(R.sub.10))Pd(R.sub.4 R.sub.5 P(V).sub.b ZR.sub.6 R.sub.7)]X;
- Pd(R.sub.4 R.sub.5 P(V).sub.b ZR.sub.6 R.sub.7).sub.2 ;
- Pd(PR.sub.1 R.sub.2 R.sub.3).sub.4 ;
- [Pd(D)(PR.sub.1 R.sub.2 R.sub.3).sub.2 ]X.sub.2 ;
- and
- [Pd(D)R.sub.4 R.sub.5 (V).sub.b ZR.sub.6 R.sub.7)]X.sub.2 ;
- wherein
- R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 can be the same or different and each are an alkyl, cycloalkyl, alkoxide, aryl, heterocyclic, functionalized alkyl, functionalized aryl, or ether group;
- R.sub.8, R.sub.9, and R.sub.10 are the same or different and each are hydrogen, alkyl, cycloalkyl, aryl, heterocyclic, halogen, ether, sulfide, carbonyl or are linked together to form a ring;
- V is CH.sub.2 or CH as part of unsaturated component;
- Z is phosphorus or nitrogen;
- D is a cyclic diene;
- X is an anion;
- Ph is a phenyl group;
- P is phosphorus;
- Pd is palladium;
- and
- b is a number in the range from 1 to 4;
- and
- wherein said reaction medium is selected from the group consisting of 2-methoxyethanol, N-methylformamide, methanol, dimethyl sulfoxide, acetonitrile, nitromethane, 2-propanol, ethanol, glycerol, 1,2-ethanediol, 2,2,2-trifluoroethanol, water, and an 80:20 solution of ethanol and water.
24 more elements
Dependencies are inferred from the claim text.