Catalyst and method for the carbonylation of oxiranes

• US 7,420,064 B2
• Filed: 07/31/2003
• Issued: 09/02/2008
• Est. Priority Date: 08/01/2002
• Status: Expired due to Fees

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Luinstra, Gerrit, Rieger, Bernhard, Molnar, Ferenc, Allmendinger, Markus
• Primary Examiner(s): SHIAO, REI TSANG
• Application Number:
  US10/523,263
• Publication Number:
  US 20050256320A1
• Time in Patent Office: 1,860 Days
• Field of Search: 549/328, 502/152
• US Class Current: 549/328
• 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 2531/845 Cobalt
• CPC Class Codes: B01J 31/122 Metal aryl or alkyl compounds
• CPC Class Codes: B01J 31/143 of aluminium
• CPC Class Codes: B01J 31/20 Carbonyls
• CPC Class Codes: C07D 303/04 containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
• CPC Class Codes: C07D 305/12 Beta-lactones

Abstract

Lactones are prepared by catalytic carbonylation of oxiranes using a catalyst system comprising

• • a) at least one cobalt compound as component A and
  • b) at least one metal compound of the formula (I) as component B,
    MX_xR_n-x   (I)
    where
  • M is an alkaline earth metal or a metal of group 3, 4 or preferably 12 or 13 of the Periodic Table of the Elements,
  • R is hydrogen or a hydrocarbon radical which may be substituted on the carbon atoms other than the carbon atom bound to M,
  • X is an anion,
  • n is a number corresponding to the valence of M and
  • x is in the range from 0 to n,
  • with n and x being selected so that the compound is uncharged, as catalyst.

Claims

1. A process for preparing lactones which comprises catalytic carbonylating an oxirane with a catalyst system comprising

a) at least one cobalt compound as component A and

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

MX_XR_n-X 

 

(I)

where

M Al, Mg or Zn,

R 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,

X Cl, Br, I, sulfonate, oxide, C_1-32-alkoxide or amide,

n is a number corresponding to the valence of M and

x is in the range from 0 to n,

with n and x being selected so that the compound is uncharged,

and wherein said oxirane is ethylene oxide, propylene oxide, butylene oxide, cyclopentene oxide or cyclohexene oxide.

2. The process as claimed in claim 1, wherein the component A is selected so that a cobalt carbonyl compound is present under the reaction conditions.

3. The process as claimed in claim 1, wherein the component B is AlCl_xR_3-x where x is from 0 to 3 and R is C_1-6-alkyl.

4. The process as claimed in claim 1, with the exception of the combination Al(C₂H₅)₃/Co(acac)₃.

6. The process as claimed in claim 5, as defined in claim 1, wherein said at least one metal compound of the formula (I) is trimethylaluminurn, triethylaluminum, tri(sec-butyl)aluminum or triisopropoxyaluminum.

7. The process as claimed in claim 5, as defined in claim 1, wherein said at least one metal compound of the formula (I) is trimethylaluminum, triethylaluminum, tri(sec-butyl)aluminum or triisopropoxyaluminum.

8. A process as claimed in claim 6, wherein said at least one metal compound of the formula (I) is trimethylaluminum, triethylaluminum, tri(sec-butyl)aluminum or triisopropoxyaluminum.

5. A process for preparing a catalyst which comprises mixing

a) at least one cobalt compound as component A and

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

MX_xR_n-x  

 

(I)

where

M Al, Mg or Zn,

R 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,

X Cl, Br, I, sulfonate, oxide, C_1-32-alkoxide or amide,

n is a number corresponding to the valence of M and

x is in the range from 0 to n, with n and x being selected so that the compound is uncharged.

9. The process as claimed in claim 5, wherein said catalyst is not the combination Al(C₂H₅)₃/Co(acac)₃.