Catalyst for the carbonylation of oxiraines

• US 20070161806A1
• Filed: 01/20/2005
• Published: 07/12/2007
• Est. Priority Date: 01/20/2004
• Status: Abandoned Application

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Molnar, Ferenc, Preishuber-Pflugl, Peter
• Application Number:
  US10/586,826
• Publication Number:
  US 20070161806A1
• Time in Patent Office: Days
• US Class Current: 549/263
• CPC Class Codes: B01J 2231/34 Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
• CPC Class Codes: B01J 2531/0208 Bimetallic complexes, i.e. comprising one or more units of two metals, with metal-metal bonds but no all-metal (M)n rings, e.g. Cr2(OAc)4
• CPC Class Codes: B01J 2531/0219 Bimetallic complexes, i.e. comprising one or more units of two metals, with metal-metal bonds but no all-metal (M)n rings, e.g. Cr2(OAc)4
• CPC Class Codes: B01J 2531/0266 Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
• CPC Class Codes: B01J 2531/0269 Complexes comprising ligands derived from the natural chiral pool or otherwise having a characteristic structure or geometry
• CPC Class Codes: B01J 2531/22 Magnesium
• CPC Class Codes: B01J 2531/26 Zinc
• CPC Class Codes: B01J 2531/31 Aluminium
• CPC Class Codes: B01J 2531/42 Tin
• CPC Class Codes: B01J 2531/46 Titanium
• CPC Class Codes: B01J 2531/48 Zirconium
• CPC Class Codes: B01J 2531/845 Cobalt
• CPC Class Codes: B01J 31/182 comprising aliphatic or saturated rings
• CPC Class Codes: B01J 31/20 Carbonyls
• CPC Class Codes: B01J 31/2208 Oxygen, e.g. acetylacetonates
• CPC Class Codes: C07D 305/12 Beta-lactones

Abstract

Lactones are prepared by the catalytic carbonylation of oxiranes using a catalyst system comprising a) at least one carbonylation catalyst A comprising uncharged or anionic transition metal complexes of metals of groups 5 to 11 of the Periodic Table, b) at least one metal compound B of the formula (I)
MX_xR_n-x  (I)  where M is an element of group 2, 3, 4, 12, 13, R is hydrogen or a hydrocarbon radical which may be substituted on the carbon atoms other than on the carbon atom bound to M, X is an anion, n is a number corresponding to the valence of M, x is in the range from 0 to n, and c) at least one organic, chiral compound C which has fewer than four coordination sites.

Claims

1-10. -10. (canceled)

11. A process for preparing lactones by catalytic carbonylation of oxiranes using a catalyst system comprising

a) at least one carbonylation catalyst A comprising uncharged or anionic transition metal complexes of metals of groups 5 to 11 of the Periodic Table of the Elements,

b) at least one metal compound B of the formula (I)

MX_xR_n-x 

 

(I)

 

where

M is an element of group 2, 3, 4, 12, 13,

R is hydrogen or a hydrocarbon radical which may be substituted on the carbon atoms other than on the carbon atom bound to M,

X is an anion,

n is a number corresponding to the valence of M,

x is in the range from 0 to n, and

c) at least one organic, chiral compound C that is a bisoxazoline compound and/or comprises at least one chiral alcohol.

12. The process as claimed in claim 11, wherein enantiomerically enriched lactones are obtained in the process.

13. The process as claimed in claim 11, wherein the component A is selected so that a cobalt carbonyl compound is present under the reaction conditions.

14. The process as claimed in claim 11, wherein M in the formula (I) is Al, Mg, Zn, Ti, Zr or Sn.

15. The process as claimed in claim 11, wherein, in the formula (I), R is hydrogen or C_1-32-alkyl, C_2-20-alkenyl, C_3-20-cycloalkyl, C_6-18-aryl, C_7-20-aralkyl or C_7-20-alkaryl, where substituents may be present on the carbon atoms other than the carbon atom bound to M,

and/or X is Cl, Br, I, sulfonate, oxide, C_1-32-alkoxide or amide.

16. The process as claimed in claim 11, wherein the component B is AlCl_xR_3-x, where x is from 0 to 3 and R is C_1-6-alkyl.

17. The process for preparing a catalyst system by mixing the components A, B and C as set forth in claim 11 in any order.

18. A catalyst system comprising the components A, B, C as defined in claim 11.

19. A method of using a catalyst system as claimed in claim 18 in carbonylation reactions.