Cyanohydrination catalyst and process

• US 5,057,477 A
• Filed: 12/06/1989
• Issued: 10/15/1991
• Est. Priority Date: 12/07/1988
• Status: Expired due to Fees

• Current Assignee: Bromine Compounds Limited Makleff House Beer-Sheva 84101 Israel
• Original Assignee: Bromine Compounds Limited (ICL Group Ltd.)
• Inventors: Shvo, Youval, Becker, Yigal, Elgavi, Asher
• Primary Examiner(s): Davis, Curtis R.
• Assistant Examiner(s): Irzinski, E. D.
• Application Number:
  US07/447,095
• Time in Patent Office: 678 Days
• Field of Search: 502/159, 502/167
• US Class Current: 502/159
• CPC Class Codes: B01J 2231/323 Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
• CPC Class Codes: B01J 31/0237 Amines
• CPC Class Codes: B01J 31/0244 with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
• CPC Class Codes: B01J 31/08 Ion-exchange resins
• CPC Class Codes: C07C 255/36 the carbon skeleton being further substituted by hydroxy groups
• CPC Class Codes: C07C 255/37 the carbon skeleton being further substituted by etherified hydroxy groups

Abstract

A catalyst for the asymmetric cyanohydrination of m-phenoxybenzaldehyde, comprises a catalytically effective amount of enantiomeric cyclo (phenylalanyl-histidine) adsorbed on a solid support comprising a non-ionic polymer resin.

The catalyst is particularly useful as a catalyst in a process for the preparation of (s)-m-phenoxybenzaldehyde cyanohydrin, in which m-phenoxybenzaldehyde is reacted in a cyanohydrination solvent.

Claims

1. A catalyst for the asymmetric cyanohydrination of m-phenoxybenzaldehyde, comprising a catalytically effective amount of enantiomeric cyclo (phenylalanyl-histidine) adsorbed on a solid support comprising a non-ionic polymer resin.

2. A catalyst according to claim 1, wherein the non-ionic polymer resin comprises a styrene-divinylbenzene copolymer.

3. A catalyst according to claim 1, wherein the enantiomeric cyclo (phenylalanyl-histidine) is cyclo-(D-phenylalanyl-D-histidine).

4. A catalyst according to claim 2, wherein the styrene-divinylbenzene copolymer is selected from the group consisting of the XAD resins, the Diaion HP resins and Sepabead SP207.

5. A catalyst according to claim 4, wherein the XAD resin is XAD-4.

6. A method for preparing a catalyst as defined in claim 1, comprising contacting an aqueous solution of the cyclo (phenylalanyl-histidine) with the non-ionic polymer resin, washing the resulting catalyst to remove non-adsorbed cyclo (phenylalanyl-histidine), and drying.

7. A catalyst according to claim 2, wherein the enantiomeric cyclo-(phenylalanyl-histidine) is cyclo-(D-phenylalanyl-D-histidine).

8. A catalyst according to claim 7, wherein the styrene-divinylbenzene copolymer is selected from the group consisting of the XAD resins, the Diaion HP resins and Sepabead SP207.

9. A catalyst according to claim 8, wherein the XAD resin is XAD-4.

10. A method for preparing the catalyst as defined in claim 5, comprising contacting an aqueous solution of the cyclo-(D-phenylalanyl-D-histidine) with XAD-4, washing the resulting catalyst to remove non-adsorbed cyclo-(D-phenylalanyl-D-histidine), and drying.