Process for the carbonylation of pentenenitrile

Details Process for the carbonylation of pentenenitrile Process for the carbonylation of pentenenitrile

2006-04-11

2006-04-11

Zucker, Paul A. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C558S441000

Reexamination Certificate

active

07026473

ABSTRACT:
Processes to prepare 5-cyanovaleric acid or its ester are provided, by carbonylation of a pentenenitrile, wherein pentenenitrile is reacted with carbon monoxide and water and/or an alcohol in the presence of a catalyst system. The catalyst system contains:(a) a metal of Group VIII or a compound thereof and(b) a bidentate phosphine, arsine and/or stibine ligand, wherein the bidentate ligand has the general formula (I):in-line-formulae description="In-line Formulae" end="lead"?R1R2-M1-R-M2-R3R4  (I)in-line-formulae description="In-line Formulae" end="tail"? wherein M1and M2are independently P, As or Sb, R is a divalent organic bridging group, which bridging group comprises a chain of 3 to 5 atoms directly connecting the 2 phosphorus atoms, which chain consists of carbon atoms and optionally a nitrogen, oxygen or sulphur atom or a silano or dialkylsilicon group, which alkyl groups independently comprise from 1 to 4 carbon atoms, and R1–R4represent the same or different optionally substituted tertiary alkyl groups,(c) an acid having a pKa less than 3, as measured at 18° C. in an aqueous solution.ε-caprolactam is also prepared by reduction of 5-cyanovaleric acid or ester obtained above to 6-aminocaproic acid or ester, and then cyclisation of the 6-aminocaproic acid or ester to ε-caprolactam.

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International Preliminary Examination Report for PCT/EP01/02903 of Jan. 28, 2002.

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