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US 5,326,873 AGranted
Palladium catalyzed addition of amines to 3,4-epoxy-1-butene
AssigneeEastman Kodak Company
InventorsStephen A. Godleski, Yann Hung
Life of this patent
Estimating the term…
Abstract
A method of forming 4-amino-2-buten-1-ol using 3,4-epoxy-1-butene is disclosed. A nitrogen nucleophile (e.g., an amine) is reacted with 3,4-epoxy-1-butene in the presence of a polymer-bound complex of palladium having up to four phosphine ligands.
Claims20
A process of forming N-substituted-4-amino-2-buten-1-ol comprising the steps of:
- providing a quantity of 3,4-epoxy-1-butene;
- providing a quantity of an amine;
- and
- reacting said quantity of 3,4-epoxy-1-butene with said amine in a reaction medium and in the presence of a catalyst consisting essentially of a bound complex of palladium with up to four phosphine ligands to form N-substituted-4-amino-2-buten-1-ol, wherein said palladium is bound to a support selected from the group consisting of polystyrene, polystyrene beads crosslinked with divinylbenzene, alumina, silica gel, polyvinyl chloride, polybutadiene, polyvinyl alcohol, copolymers of styrene and methacrylate, and cellulose.
1 more element
A process for forming N-substituted 4-amino-2-buten-1-ol comprising:
- providing a quantity of 3,4-epoxy-1-butene;
- providing a quantity of an amine selected from the group consisting of methylamine, diethylamine, ethylaminoethanol, piperazine, piperidine, N,N-diethyl-phenylenediamine, and imidazole;
- and
- reacting said quantity of 3,4-epoxy-1-butene with said amine in a solvent selected from the group consisting of tetrahydrofuran, diethyl ether, toluene, benzene, N,N-dimethylformamide, and dimethyl sulfoxide, and in the presence of a catalyst consisting essentially of a complex of palladium with up to four phosphine ligands bound to polystyrene beads to form N-substituted 4-amino-2-buten-1-ol, wherein said polystyrene beads have a diameter in the range of from about 15 to 300 .mu.m and are cross-linked with 1-10 weight percent divinylbenzene, and the ratio of said phosphine to said palladium on said polystyrene beads is in the range of about 1:1 to 20:1.
1 more element
A process for forming N-substituted-4-amino-2-buten-1-ol comprising the steps of:
- providing a quantity of 3,4-epoxy-1-butene;
- providing a quantity of an amine;
- and
- reacting said quantity of 3,4-epoxy-1-butene with said amine in a reaction medium and in the presence of a catalyst consisting essentially of a bound complex of palladium with up to four phosphine ligands to form N-substituted-4-amino-2-buten -1-ol, wherein said catalyst has a formula selected from the group consisting of:
- ##STR5## wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, and R.sub.12 are the same or different and are substituted or unsubstituted hydrocarbons with no more than one of R.sub.4 -R.sub.12 having more than seven carbon atoms, and R.sub.13 and R.sub.14 are phenyl, tolyl, or furyl, and said polymer includes a repeating unit which is a polyaromatic compound and ##STR6## wherein R.sub.19, R.sub.20, R.sub.21, R.sub.22, R.sub.23, and R.sub.24 are the same or different and are substituted or unsubstituted hydrocarbons with no more than one of R.sub.19 -R.sub.24 having more than seven carbon atoms, and R.sub.15, R.sub.16, R.sub.17, and R.sub.18, are phenyl, tolyl, or furyl and said palladium is bound to a support selected from the group consisting of polystyrene, polystyrene beads cross-linked with divinylbenzene, alumina, silica gel, polyvinyl chloride, polybutadiene, polyvinyl alcohol, copolymers of styrene and methacrycylate, and cellulose.
2 more elements
Dependencies are inferred from the claim text.