Process for the hydrogenolysis of C--O and C.dbd.O bonds in organic substances

• US 5,773,677 A
• Filed: 09/19/1996
• Issued: 06/30/1998
• Est. Priority Date: 09/23/1995
• Status: Expired due to Fees

• Current Assignee: Degussa-Hüls AG (Rag-Stiftung)
• Original Assignee: Degussa AG (Rag-Stiftung)
• Inventors: Kunz, Guenther, Scholz, Mario, Freund, Andreas, Lansink-Rotgerink, Hans
• Primary Examiner(s): BARTS, SAMUEL A
• Application Number:
  US08/715,775
• Time in Patent Office: 649 Days
• Field of Search: 585/469
• US Class Current: 585/469
• CPC Class Codes: C07B 31/00 Reduction in general
• CPC Class Codes: C07C 1/22 by reduction
• CPC Class Codes: C07C 15/073 Ethylbenzene
• CPC Class Codes: C07C 2523/38 of noble metals
• CPC Class Codes: C07C 2523/755 Nickel
• CPC Class Codes: C07C 2529/10 containing iron group metals, noble metals or copper
• CPC Class Codes: C07C 2529/20 containing iron group metals, noble metals or copper
• CPC Class Codes: C07C 2529/42 containing iron group metals, noble metals or copper

Abstract

A process for hydrogenolysis of C--O and C═O bonds in organic substances by reaction with hydrogen in the presence of a catalyst system which contains at least one metal from Groups VIII and/or IB of the Periodic System of Elements on a support consisting of at least one solid acid with an acid activity index of at least 90%.

Claims

1. A process for the hydrogenolysis of a compound represented by the structural formula I or II to give a compound represented by the structural formula III or IV ##STR3## comprising reacting I or II with hydrogen in the presence of a catalyst system that is a solid catalyst which contains at least one metal from Group VIII and/or Group IB of the Periodic System of Elements on a support consisting of at least one solid acid with an acid activity index of at least 90%, wherein the substituents R₁ to R₈, are the same or different, and are each a member selected from the group consisting of hydrogen, alkyl, substituted or non-substituted aryl, hydroxyl, alkoxy, substituted or non-substituted aryloxy, halogen, carboxyl, a carboxylic acid derivative group, acyloxy, nitro, a sulphonic acid, mercapto, amino, alkyl-substituted amino and substituted or non-substituted aryl-substituted amino.

2. The process according to claim 1, wherein said catalyst contains at least one of the metals selected from the group consisting of palladium, platinum, rhodium and nickel.

3. The process according to claim 1 wherein the solid acid is an amorphous mixed oxide which contains silicon and aluminum or a crystalline compound containing silicon, aluminum and oxygen.

4. The process according to claim 1 wherein the solid acid is a zeolite.

5. The process according to claim 4, wherein the zeolite is ZSM-5, Y, beta or mordenite.

6. The process according to claim 1 wherein a non-zeolitic material is used as the solid acid.

7. The process according to claim 1 wherein at least one mixed oxide is used as a non-zeolitic material.

8. The process according to claim 7 wherein the mixed oxide is modified with an acid.

9. The process according to claim 1 wherein R₁ to R₈, independently of each other, are hydrogen (H), alkyl groups, substituted or non-substituted aryl groups, substituted or non-substituted phenyl groups, hydroxyl groups, alkoxy groups, substituted or non-substituted aryloxy groups, halogen groups, carboxylic acid groups, carboxylic acid derivative groups, acyloxy groups, nitro groups, sulphonic acid groups, mercapto groups, amino groups, alkyl-substituted amino groups or substituted or non-substituted aryl-substituted amino groups.

10. The process according to claim 1 wherein at least one R₁ to R₈ is alkyl containing 1 to 20 carbon atoms.

11. The process according to claim 1 wherein at least one of R₁ to R₈ is phenyl.

12. A process for the hydrogenolysis of a compound represented by the structural formula I or II to give a compound represented by the structural formula III or IV and which does not require use of corrosive media ##STR4## comprising reacting I or II with hydrogen in the presence of a catalyst system that is a solid catalyst which contains at least one metal from Group VIII and/or Group IB of the Periodic System of Elements on a support consisting of at least one solid acid with an acid activity index of at least 90%, said acid activity index determinable by passing a gas stream consisting of 5 vol. % isopropanol and 95% vol. % helium through 100 grams of catalyst particles of a size range of 0.5 to 2.0 mm and with a flow rate of 50 ml/minute to thereby decompose said isopropanol to propene and water and then measuring the degree of conversion of isopropanol at 250°

C., wherein the substituents R₁ to R₈, are the same or different, and are each a member selected from the group consisting of hydrogen alkyl, substituted or non-substituted aryl, hydroxyl, alkoxy, substituted or non-substituted aryloxy, halogen, carboxyl, a carboxylic acid derivative group, acyloxy, nitro, a sulphonic acid, mercapto, amino, alkyl-substituted amino and substituted or non-substituted aryl-substituted amino.

13. The process according to claim 12 further comprising the catalyst additionally containing a promoter selected from the group consisting of Sn, Ge, Pb and In.

14. The process according to claim 12 wherein said metal is present in an amount of 0.01 to 90% by weight based on the weight of the catalyst.

15. The process according to claim 12 wherein said support is a member selected from the group consisting of (a) an amorphous mixed oxide containing silicon and aluminum and (b) a crystalline compound based on Si, Al and O.

16. The process according to claim 15 wherein the support is an amorphous mixed oxide with a SiO₂ /Al₂ O₂ molar ratio of 99:

1 to 1;

99.