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US4024197A Expired / Lapsed US ⏱️ 0.0 years remaining

Production of butanediol

Assignee: EIDP Inc
•
Filing: 1975-12-31
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Granted: 1977-05-17
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Expires: 1995-12-31
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Abstract

Abstract 2-VINYL-5-METHYL-1,3-DIOXANE IS PROVIDED AS A NEW CYCLIC ACETAL WHICH, WHEN HYDROFORMYLATED, HYDROLYZED AND HYDROGENATED PROVIDES HIGH YIELDS OF A MIXTURE OF 1,4-BUTANEDIOL AND 2-METHYL-1,3-PROPANEDIOL.

Inventors

  • 👤 Charles C. Cumbo
  • 👤 Kamlesh K. Bhatia

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 20:12
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/14; C07C29/141

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 49 words
A process for the preparation of 1,4-butanediol and 2-methyl-1,3-propane diol by hydroformylating 2-vinyl-5-methyl-1,3-dioxane with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst under conventional conditions and then hydrogenating and hydrolyzing the hydroformylation reaction product, in the presence of water and a hydrogenation catalyst under conventional conditions.
Claim 2
Dependent Claim 49 words
A process for the preparation of 1,4-butanediol and 2-methyl-1,3-propane diol by hydroformylating 2-vinyl-5-methyl-1,3-dioxane with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst under conventional conditions and then hydrogenating and hydrolyzing the hydroformylation reaction product, in the presence of water and a hydrogenation catalyst under conventional conditions.
Claim 3
Dependent Claim 123 words
The process of claim 1 wherein the 2-vinyl-5-methyl-1,3-dioxane is hydroformylated by reacting it with hydrogen and carbon monoxide for about one-five hours at a molar ratio of H 2 :CO of 0.9:1 - 1.2:1 in the presence of a rhodium carbonyl catalyst at a molar ratio to the cyclic acetal of 0.5 × 10 - 3 - 6.0 × 10 - 3 and a phosphite having the formula ##STR28## wherein R 1 , R 2 and R 3 are the same or different alkyl groups having 1 - 12 carbon atoms or phenyl at a molar ratio to the rhodium catalyst of about 5:1 - 50:1 at a temperature of 85° - 110° C and a pressure of about 75 - 150 psig.
Claim 4
Dependent Claim 24 words
The process of claim 2 wherein R 1 , R 2 and R 3 are the same alkyl groups having 1- 3 carbon atoms.
Claim 5
Dependent Claim 17 words
The process of claim 2 wherein the reaction is carried out for about 1 - 2 hours.
Claim 6
Dependent Claim 15 words
The process of claim 2 wherein the molar ratio of H 2 :CO is 1:1.
Claim 7
Dependent Claim 30 words
The process of claim 2 wherein the molar ratio of the rhodium catalyst to the cyclic acetal is 1 × 10 - 3 - 2 × 10 - 3 .
Claim 8
Dependent Claim 20 words
The process of claim 2 wherein the molar ratio of the phosphite to the rhodium catalyst is 10:1 - 20:1.
Claim 9
Dependent Claim 21 words
The process of claim 2 wherein the temperature is 100° - 110° C. and the pressure is 100 - 110 psig.
Claim 10
Dependent Claim 59 words
The process of claim 1 wherein the hydroformylation reaction product is mixed with water at a molar ratio of water to reaction product of 1:1 - 20:1 and then hydrolyzed and hydrogenated in the presence of a catalytic amount of a hydrogenation catalyst at a temperature of 30° - 130° C. and a pressure of 100 - 5,000 psig.

References Cited (Backward Citations)

US2566559A Cited
US2122813A Cited
US2888492A Cited
US2808440A Cited
US3102899A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-05-16 1980-11-15 1981-05-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-05-16 1984-11-15 1985-05-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-05-16 1988-11-15 1989-05-17 $7700.00 Window Closed / Lapsed

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