Process for the hydrocyanation of organic compounds containing ethylenic unsaturation
AssigneeRhone-Poulenc Fiber & Resin Intermediates
InventorsMarc Huser, Robert Perron
Life of this patent
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Abstract
The present invention relates to a process for the hydrocyanation of organic compounds containing ethylenic unsaturation to nitrites, in particular the hydrocyanation of diolefins or of substituted olefins, such as alkenenitriles. More specifically, it comprises a process for the hydrocyanation of organic compounds containing at least one ethylenic double bond by reaction with hydrogen cyanide in the presence of an aqueous solution of a catalyst comprising at least one transition metal compound and at least one water-soluble phosphine, characterized in that the said water-soluble phosphine is a monodentate or bidentate phosphine.
Claims21
A process for the hydrocyanation of organic compounds containing at least one ethylenic double bond, said process comprising reacting an organic compound containing at least one ethylenic double bond, at least one compound of a transition metal and at least one water-soluble phosphine with hydrogen cyanide in the presence of an aqueous solution of a catalyst wherein said water-soluble phosphine is a monodentate or bidentate phosphine corresponding to the general formula (I):
- ##STR3## wherein:
- Ar1 and Ar2, which are identical or different, represent aryl groups or aryl groups containing one or a number of substituents consisting of:
- alkyl or alkoxy radical having 1 to 4 carbon atoms,
- halogen atom, or
- hydrophilic group, consisting of:
- --COOM, --SO.sub.3 M or --PO.sub.3 M, M representing an inorganic or organic cationic residue chosen from a proton, cations derived from alkali or alkaline-earth metals, ammonium cations --N(R).sub.4, in the formula of which the R symbols, which are identical or different, represent a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms, and other cations derived from metals, the arylcarboxylic acid, arylsulphonic acid or arylphosphonic acid salts of which are soluble in water,
- Ar3 represents an aryl group containing one or a number of substituents consisting of:
- alkyl or alkoxy radical having 1 to 4 carbon atoms,
- halogen atom,
- hydrophilic group, consisting of:
- --COOM or --PO.sub.3 M, M representing an inorganic or organic cationic residue chosen from a proton, cations derived from alkali or alkaline-earth metals, ammonium cations --N(R).sub.4, in the formula of which the R symbols, which are identical or different, represent a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms, and other cations derived from metals, the arylcarboxylic acid or arylphosphonic acid salts of which are soluble in water,
- --N(R).sub.3, in the formula of which the R symbols, which are identical or different, represent a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms,
- --OH,
- at least one of the said substituents or Ar3 being a hydrophilic group as defined above,
- a represents 0 or 1,
- b represents 0 or 1,
- c represents an integer from 0 to 3,
- D represents an alkyl group, a cycloalkyl group or an alkyl or cycloalkyl group containing one or a number of substituents, consisting of:
- alkoxy radical having 1 to 4 carbon atoms,
- halogen atom,
- hydrophilic group, consisting of:
- --COOM, --SO.sub.3 M or --PO.sub.3 M, M representing an inorganic or organic cationic residue chosen from a proton, cations derived from alkali or alkaline-earth metals, ammonium cations --N(R).sub.4, in the formula of which the R symbols, which are identical or different, represent a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms, and other cations derived from metals, the arylcarboxylic acid, arylsulphonic acid or arylphosphonic acid salts of which are soluble in water,
- --N(R).sub.3, in the formula of which the R symbols, which are identical or different, represent a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms,
- d represents an integer from 0 to 3,
- the sum (a+b+c+d) is equal to 3 or to the general formula (II):
- ##STR4## in which:
- Ar1, Ar2 and D have the meanings indicated above for the formula (I),
- a, b, e and f each represent 0 or 1,
- d and g each represent an integer from 0 to 2,
- the sum (a+b+d) is equal to 2,
- the sum (e+f+g) is equal to 2,
- L represents a single valency bond or a divalent hydrocarbon radical.
Dependencies are inferred from the claim text.