Claims
- 1. A process for hydroformylating an internally unsaturated C.sub.4 -C.sub.12 carboxylic acid, a corresponding ester, or a corresponding nitrile to produce a linear .omega.-formyl-carboxylic acid or a corresponding linear formyl nitrile compound, wherein said process is carried out under effective hydroformylation conditions in an aqueous medium in the presence of carbon monoxide, hydrogen, and a catalyst comprising platinum and a water-soluble organic bidentate ligand.
- 2. The process according to claim 1, wherein the water-soluble bidentate ligand is represented by the following general formula: R.sup.1 R.sup.2 --M.sup.1 --R--M.sup.2 --R.sup.3 R.sup.4, where M.sup.1 and M.sup.2 represent a phosphorous (P) atom, an antimony atom or an arsenic atom, R represents a divalent organic bridging group having at least three atoms, and wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently C.sub.1 -C.sub.15 alkyl, C.sub.3 -C.sub.15 cycloalkyl or C.sub.5 -C.sub.20 aryl groups and where at least one hydrophilic group is substituted on at least one of the groups R.sup.1, R.sup.2, R.sup.3, R.sup.4 or R.
- 3. The process according to claim 2, wherein the aryl group is selected from the group consisting of naphthyl and phenyl.
- 4. The process according to claim 2, wherein the aryl group is a heterocyclic group.
- 5. The process according to claim 2, wherein the bridging group R contains 3-30 carbon atoms.
- 6. The process according to claim 2, wherein the bridging group R is selected from the class of divalent C.sub.9 -C.sub.12 alkyl groups.
- 7. The process according to claim 2, wherein the bridging group R forms a rigid link between M.sup.1 and M.sup.2.
- 8. The process according to claim 2, wherein M.sup.1 and M.sup.2 represent a phosphorous atom.
- 9. The process according to claim 2, wherein the bridging group R forms a rigid link between M.sup.1 and M.sup.2, and wherein M.sup.1 and M.sup.2 represent a phosphorous atom.
- 10. The process according to claim 2, wherein the hydrophilic group is a sulphonate group (--SO.sub.3 Z), a phosphonate group (--PO.sub.3 Z), a carboxylate group (--COOZ), or a cationic group of an ammonium salt (--N(R.sup.5).sub.3 X), wherein Z represents a cationic group, R.sup.5 represents an aliphatic hydrocarbon group having from 1 to 18 carbon atoms and X represents an anionic group.
- 11. The process according to claim 7 or claim 8, wherein the hydrophilic group is a sulphonate group (--SO.sub.3 Z), a phosphonate group (--PO.sub.3 Z), a carboxylate group (--COOZ), or a cationic group of an ammonium salt (--N(R.sup.5).sub.3 X), wherein Z represents an aliphatic hydrocarbon group having from 1 to 18 carbon atoms and X represents an anionic group.
- 12. The process according to claim 1 for the preparation of a linear .omega.-formyl-carboxylic acid or a corresponding linear formyl-nitrile compound, wherein an acid with a pKa<2 is included in the hydroformylating reaction.
- 13. The process according to claim 1, wherein said internally unsaturated carboxylic acid or ester or nitrile is represented by at least one of the following formulas:
- CH.sub.3 --CH.dbd.CH--CH.sub.2 --L (1)
- CH.sub.3 --CH.sub.2 --CH.dbd.CH--L (2)
- wherein L is ##STR3## wherein Y.sup.1 represents an alkyl group with 1 to 8 carbon atoms, an aryl group with 6 to 12 carbon atoms or an aralkyl group with 7 to 12 carbon atoms.
- 14. The process for preparing a linear .omega.-formyl-carboxylic acid according to claim 1, 2, 7, 8, 9, 10, 12 or 13, wherein the process further comprises after the hydroformylating, separating the .omega.-formyl-carboxylic acid from the catalyst-containing aqueous hydroformylation mixture by means of extraction, and returning the resulting aqueous mixture, containing the catalyst system to the hydroformylating step.
- 15. A process for preparing 6-aminocaproic acid via reductive amination of 5-formylvaleric acid, wherein the 5-formylvaleric acid is obtained by the process according to claim 14.
- 16. The process for preparing .epsilon.-caprolactam from 6-aminocaproic acid obtained by the process according to claim 15, in which process 6-aminocaproic acid is converted into .epsilon.-caprolactam via ring closure at 150.degree.-370.degree. C. in a solvent.
- 17. The process for the conversion of 5-formylvaleric acid to adipic acid comprising the combination of steps of providing a mixture of adipic acid and 5-formylvaleric acid obtained according to the process according to claim 13; and oxidizing the 5-formylvaleric acid to adipic acid.
Priority Claims (2)
Number |
Date |
Country |
Kind |
9400017 |
Jan 1994 |
BEX |
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9400018 |
Jan 1994 |
BEX |
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Parent Case Info
This is a continuation of PCT/NL95/00007 filed Jan. 5, 1995.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4542120 |
Hsu et al. |
Sep 1985 |
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4748261 |
Billig et al. |
May 1988 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
PCTNL9500007 |
Jan 1995 |
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