US3966827A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Production of 3-methylpentane-1,5-diol
Assignee: BASF SE
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Filing: 1975-01-16
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Granted: 1976-06-29
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Expires: 1995-01-16
Abstract
Abstract The production of 3-methylpentane-1,5-diol by hydroformylation of 2-methylbut-1-en-4-ol with carbon monoxide and hydrogen at elevated temperature and superatmospheric pressure in the presence of a rhodium carbonyl complex which has been modified by a tertiary organic phosphine followed by hydrogenation of the 2-hydroxy-4-methyltetrahydropyran at elevated temperature and superatmospheric pressure in the presence of a hydrogenation catalyst.
Inventors
- 👤 Werner Aquila
- 👤 Walter Himmele
- 👤 Werner Fliege
- 👤 Hardo Siegel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 21:59
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/09; C07C29/10; C07C29/103; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
172 words
A process for the production of 3-methylpentane-1,5-diol wherein 2-methylbut-1-en-4-ol is reacted with carbon monoxide and hydrogen at 60- 140°C and at 10- 700 atmospheres pressure at a ratio by volume of CO to H 2 in the range of 1:0.25 to 1:4 in the presence of a rhodium carbonyl complex which has been modified with at least three mols of a tertiary organic phosphine per gram atom of rhodium, the organic groups of said tertiary phosphine being selected from the group consisting of alkyl having 1- 20 carbon atoms, cycloalkyl having 5- 8 carbon atoms, phenyl, phenyl bearing 1- 2 alkyl groups, each having 1- 4 carbon atoms, and phenyl bearing 1- 2 alkoxy groups, each having 1- 4 carbon atoms, said rhodium complex catalyst being present in an amount of 0.5 to 500 ppm, calculated as rhodium metal and based on the 2-methylbut-1-en-4-ol, to produce 2-hydroxy-4-methyltetrahydropyran and the 2-hydroxy-4-methyltetrahydropyran thus obtained is hydrogenated at elevated temperature and at superatmospheric pressure in the presence of a conventional hydrogenation catalyst to form 3-methylpentane-1,5-diol.
Claim 2
Dependent Claim
172 words
A process for the production of 3-methylpentane-1,5-diol wherein 2-methylbut-1-en-4-ol is reacted with carbon monoxide and hydrogen at 60- 140°C and at 10- 700 atmospheres pressure at a ratio by volume of CO to H 2 in the range of 1:0.25 to 1:4 in the presence of a rhodium carbonyl complex which has been modified with at least three mols of a tertiary organic phosphine per gram atom of rhodium, the organic groups of said tertiary phosphine being selected from the group consisting of alkyl having 1- 20 carbon atoms, cycloalkyl having 5- 8 carbon atoms, phenyl, phenyl bearing 1- 2 alkyl groups, each having 1- 4 carbon atoms, and phenyl bearing 1- 2 alkoxy groups, each having 1- 4 carbon atoms, said rhodium complex catalyst being present in an amount of 0.5 to 500 ppm, calculated as rhodium metal and based on the 2-methylbut-1-en-4-ol, to produce 2-hydroxy-4-methyltetrahydropyran and the 2-hydroxy-4-methyltetrahydropyran thus obtained is hydrogenated at elevated temperature and at superatmospheric pressure in the presence of a conventional hydrogenation catalyst to form 3-methylpentane-1,5-diol.
Claim 3
Dependent Claim
20 words
A process as claimed in claim 1 wherein the said CO to H 2 ratio is from 1:0.5 to 1:2.
Claim 4
Dependent Claim
33 words
A process as claimed in claim 1 wherein the mixture of carbon monoxide and hydrogen is used in a stoichiometric amount based on 2-methylbut-1-en-4-ol or in an excess of up to 200 mole%.
Claim 5
Dependent Claim
16 words
A process as claimed in claim 1 wherein the said temperature is from 70° to 110°C.
Claim 6
Dependent Claim
18 words
A process as claimed in claim 1 wherein the pressure during hydroformylation is from 80 to 700 atmospheres.
Claim 7
Dependent Claim
27 words
A process as claimed in claim 1 wherein the amount of rhodium complex catalyst is 1 to 50 ppm calculated as rhodium metal and based on 2-methylbut-1-en-4-ol.
Claim 8
Dependent Claim
14 words
A process as claimed in claim 1 wherein said tertiary phosphine is triphenyl phosphine.
Claim 9
Dependent Claim
21 words
A process as claimed in claim 1 wherein said tertiary phosphine is trianisyl phosphine, tri-p-tolyl phosphine, tri-n-butyl phosphine or tricyclohexyl phosphine.
Claim 10
Dependent Claim
23 words
A process as claimed in claim 1 wherein the atomic ratio of rhodium to phosphorus in the catalyst is from 1:5 to 1:30.
Claim 11
Dependent Claim
30 words
A process as claimed in claim 1 wherein only a portion of the 2-methylbut-1-en-4-ol is hydroformylated and the unreacted 2-methylbut-1-en-4-ol is returned to the reaction after separation of the 2-hydroxy-4-methyltetrahydropyran.
Claim 12
Dependent Claim
25 words
A process as claimed in claim 1 wherein hydrogenation is carried out at from 60° to 250°C and a pressure of 20 to 300 atmospheres.
Claim 13
Dependent Claim
30 words
A process as claimed in claim 1 wherein the hydrogenation is carried out at a temperature of from 80° to 180°C and a pressure of from 50 to 200 atmospheres.
Claim 14
Dependent Claim
23 words
A process as claimed in claim 1 wherein a hydrogen partial pressure of from 50 to 150 atmospheres is maintained during the hydrogenation.
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) | 1979-06-29 | 1979-12-29 | 1980-06-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-29 | 1983-12-29 | 1984-06-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-29 | 1987-12-29 | 1988-06-29 | $7700.00 | Window Closed / Lapsed |