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US4173588A Expired / Lapsed US ⏱️ 0.0 years remaining

Manufacture of 2-methyl-2-hepten-6-one

Assignee: BASF SE
•
Filing: 1977-11-03
•
Granted: 1979-11-06
•
Expires: 1997-11-03
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Abstract

Abstract An improved process for the manufacture of 2-methyl-2-hepten-6-one by reacting an alkyl acetoacetate with 2-methyl-3-buten-2-ol in the presence of an organic aluminum compound such as aluminum trialcoholate, aluminum triacetoacetate, aluminum alkylacetoacetate or aluminum triaryloxylate. 2-Methyl-2-hepten-6-one is an intermediate for the manufacture of vitamins.

Inventors

  • 👤 Heinrich Pasedach
  • 👤 Rudolf Mohr
  • 👤 Axel Nissen

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 15:32
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/673; C07C45/676

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 174 words
In a process for the manufacture of 2-methyl-2-hepten-6-one by reacting 2-methyl-3-buten-2-ol with an alkyl acetoacetate at an elevated temperature in the presence of an organic aluminum compound, the improvement wherein the methylbutenol and the alkyl acetoacetate are reacted at from 140° to 180° C., in a molar ratio of from 0.8:1 to 2.0:1, with the proviso that the concentration of said alkyl acetoacetate in the reaction mixture during the entire reaction period is not above 15% by weight for a total time of more than two hours and wherein said organic aluminum compound has the formula ##STR2## where R 1 and R 2 are alkyl or alkoxy of 1 to 4 carbon atoms, R 3 is alkyl of 1 to 4 carbon atoms and n is 0, 1, 2 or 3 or said aluminum compound is an aluminum triaryloxylate wherein the aryloxy group is phenolate, optionally substituted by lower alkyl or lower alkoxy of 1 to 4 carbon atoms or is naphtholate, optionally substituted by alkyl or alkoxy of 1 to 4 carbon atoms.
Claim 2
Dependent Claim 174 words
In a process for the manufacture of 2-methyl-2-hepten-6-one by reacting 2-methyl-3-buten-2-ol with an alkyl acetoacetate at an elevated temperature in the presence of an organic aluminum compound, the improvement wherein the methylbutenol and the alkyl acetoacetate are reacted at from 140° to 180° C., in a molar ratio of from 0.8:1 to 2.0:1, with the proviso that the concentration of said alkyl acetoacetate in the reaction mixture during the entire reaction period is not above 15% by weight for a total time of more than two hours and wherein said organic aluminum compound has the formula ##STR2## where R 1 and R 2 are alkyl or alkoxy of 1 to 4 carbon atoms, R 3 is alkyl of 1 to 4 carbon atoms and n is 0, 1, 2 or 3 or said aluminum compound is an aluminum triaryloxylate wherein the aryloxy group is phenolate, optionally substituted by lower alkyl or lower alkoxy of 1 to 4 carbon atoms or is naphtholate, optionally substituted by alkyl or alkoxy of 1 to 4 carbon atoms.
Claim 3
Dependent Claim 25 words
A process as claimed in claim 1, wherein the methylbutenol and the alkyl acetoacetate are reacted in a molar ratio of from 1:1 to 1.5:1.
Claim 4
Dependent Claim 25 words
A process as claimed in claim 1, wherein the methylbutenol and the alkyl acetoacetate are introduced into a solution of the aluminum compound in 2-methyl-2-hepten-6-one.
Claim 5
Dependent Claim 18 words
A process as claimed in claim 1, wherein said aluminum triaryloxylate is used as the organic aluminum compound.
Claim 6
Dependent Claim 17 words
A process as claimed in claim 4, wherein aluminum triphenolate is used as the organic aluminum compound.
Claim 7
Dependent Claim 15 words
A process as claimed in claim 1, wherein the alkylacetoacetate is methyl or ethyl acetoacetate.
Claim 8
Dependent Claim 38 words
A process as claimed in claim 1 wherein the concentration of said alkyl acetoacetate in the reaction mixture during the entire reaction period is not above 15% by weight for a total time of more than one hour.
Claim 9
Dependent Claim 23 words
A process as claimed in claim 1 wherein the concentration of said alkyl acetoacetate in the reaction mixture never exceeds 5% by weight.

References Cited (Backward Citations)

US2795617A Cited
US3023246A Cited
US3101375A Cited
US3238260A Cited
US3975446A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-11-05 1983-05-07 1983-11-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-11-05 1987-05-07 1987-11-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-11-05 1991-05-07 1991-11-06 $7700.00 Window Closed / Lapsed

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