US3929915A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the production of butanediol
Assignee: EIDP Inc
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Filing: 1974-07-31
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Granted: 1975-12-30
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Expires: 1994-07-31
Abstract
Abstract A three-step process is provided in which (1) acrolein is reacted with 2-methyl-1,3-propanediol(MPD) to prepare 2-vinyl-5methyl-1,3-dioxane (VMD); (2) the VMD is hydroformylated to yield the corresponding aldehyde and (3) the aldehyde is hydrolyzed and hydrogenated to yield butanediol and 2-methyl-1,3-propanediol. The 2-methyl-1,3-propanediol product is recycled to the first step and the butanediol may be cyclized in the presence of a strong acid to prepare tetrahydrofuran if desired.
Inventors
- 👤 Charles C Cumbo
- 👤 Kamlesh K Bhatia
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 16:00
CPC Classifications
C; C07; C07D; C07D319/00; C07D319/04; C07D319/06; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/14; C07C29/141; C07C45/00; C07C45/27; C07C45/32; C07C45/33; C07C45/34; C07C45/35
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
52 words
A THREE-STEP PROCESS FOR PREPARING A 1,4-BUTANEDOL WHICH COMPRIESE REACTION ACROLEIN WITH 2-METHYL-1,3PROPANEDIOL UNDER CONVENTIONAL CONDITIONS TO PRODUCE 2VINYL-5-METHYL-1,3-DIOXANE, HYDROFORMYLATING THE 2-VINYYL-5METHYL-1,3-DIOXANE UNDER CONVENTIONAL CONDITIONS TO PRODUCE THE CORRESPONDING ALDEHYDE OF 2-VINYL-5-METHYL-1,3-DIOXANE AND THEN HYDROLYZING AND HYDROGENATING THE ALDEHYDE OF 2VINYL-5-METHYL-1,3-DIOXANE UNDER CONVENTIONAL CONDITIONS TO OBTAIN A MIXTURE OF 1,4-BUTANEDIOL AND 2-METHYL-1,3PROPANEDIOL.
Claim 2
Dependent Claim
52 words
A THREE-STEP PROCESS FOR PREPARING A 1,4-BUTANEDOL WHICH COMPRIESE REACTION ACROLEIN WITH 2-METHYL-1,3PROPANEDIOL UNDER CONVENTIONAL CONDITIONS TO PRODUCE 2VINYL-5-METHYL-1,3-DIOXANE, HYDROFORMYLATING THE 2-VINYYL-5METHYL-1,3-DIOXANE UNDER CONVENTIONAL CONDITIONS TO PRODUCE THE CORRESPONDING ALDEHYDE OF 2-VINYL-5-METHYL-1,3-DIOXANE AND THEN HYDROLYZING AND HYDROGENATING THE ALDEHYDE OF 2VINYL-5-METHYL-1,3-DIOXANE UNDER CONVENTIONAL CONDITIONS TO OBTAIN A MIXTURE OF 1,4-BUTANEDIOL AND 2-METHYL-1,3PROPANEDIOL.
Claim 3
Dependent Claim
15 words
The process of claim 1 wherein the 2-methyl propanediol is recycled to react with acrolein.
Claim 4
Dependent Claim
28 words
The process of claim 1 wherein acrolein is reacted with 2-methyl-1,3-propanediol at a temperature of 0* to 75*C. in the presence of a strongly acidic ion exchange resin.
Claim 5
Dependent Claim
64 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 1-5 hours at a molar ratio of H2: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 X 10 3 to 6.0 X 10 3 and a phosphite having the formula
Claim 6
Dependent Claim
19 words
The process of claim 4 wherein R1, R2 and R3 are the same alkyl groups having 1-3 carbon atoms.
Claim 7
Dependent Claim
17 words
The process of claim 4 wherein the reaction is carried out for about 2 - 3 hours.
Claim 8
Dependent Claim
13 words
The process of claim 4 wherein the molar ratio of H2:CO is 1:
Claim 9
Dependent Claim
27 words
The process of claim 4 wherein the molar ratio of the rhodium catalyst to the cyclic acetal is 1 X 10 3 to 2 X 10 3.
Claim 10
Dependent Claim
20 words
The process of claim 4 wherein the molar ratio of the phosphite to the rhodium catalyst is 10:1 - 20:1.
Claim 11
Dependent Claim
19 words
The process of claim 4 wherein the temperature is 100* -110*C. and the pressure is 100 - 110 psig.
Claim 12
Dependent Claim
58 words
The process of claim 2 wherein the aldehyde of 2-vinyl-5-methyl-1,3-dioxane is mixed with water at a molar ratio of water to the aldehyde of 1:1 - 20:1 and then hydrolyzed and hydrogenated in the presence of a catalytic amount of a conventional hydrogenation catalyst at a temperature of 30* -130*C. and a pressure of 100 - 5,000 psig.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-12-29 | 1979-06-30 | 1979-12-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-29 | 1983-06-30 | 1983-12-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-29 | 1987-06-30 | 1987-12-30 | $7700.00 | Window Closed / Lapsed |