US4433175A
Expired / Lapsed
US
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Process for the production of pure neohexanol
Assignee: Huels AG
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Filing: 1982-11-24
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Granted: 1984-02-21
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Expires: 2002-11-24
Abstract
Abstract For the production of neohexanol with a purity above 99%, a chlorine content of less than 10 ppm, and a sulfur content of less than 5 ppm, 3,3-dimethylbutyric acid with a chlorine content below 650 ppm, preferably below 100 ppm, is first esterified, optionally after distillatory separation into a portion richer in chlorine with a chlorine content above 650 ppm, preferably above 100 ppm, and into a portion low in chlorine with a chlorine content below 650 ppm, preferably below 100, with an alcohol boiling above 117° C., preferably an octyl alcohol. The resultant ester is separated by distillation into fractions richer in chlorine with chlorine contents above 10 ppm and into fractions low in chlorine with chlorine contents below 10 ppm. The ester of low chlorine contents below 10 ppm is hydrogenated to neohexanol over a barium-activated copper chromite catalyst under a pressure of 200-300 bar, at 120°-22° C., and with catalyst loads of 0.05-1.0 liter of hydrogenation feed/liter of catalyst . hour. The high purity of the neohexanol permits catalytic dehydrogenation to neohexanal.
Inventors
- 👤 Manfred Kaufhold
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 16:14
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/002; C07C29/00; C07C29/132; C07C29/136; C07C29/147; C07C29/149; C07C51/00; C07C51/42; C07C51/43; C07C51/44; C07C67/00; C07C67/08; C07C67/48; C07C67/52; C07C67/54
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
139 words
A process for the production of neohexanol of a purity of above 99%, a chlorine content of less than 10 ppm, and a sulfur content of less than 5 ppm, comprising esterifying 3,3-dimethylbutyric acid of a chlorine content below 650 ppm with an alkanol of a normal boiling point above 117° C.; separating the ester by distillation into chlorine rich fractions of chlorine contents above 10 ppm and chlorine poor fractions of chlorine contents below 10 ppm, during which step the chlorine content of the distillate or the sump is continuously controlled by sampling; hydrogenating the ester with a chlorine content below 10 ppm to form neohexanol, over a barium-activated copper chromite catalyst under a hydrogen pressure of 200-300 bar, at a temperature of 120°-220° C., and with a catalyst load of 0.05-1.0 liter of hydrogenation feed/liter of catalyst.hour.
Claim 2
Dependent Claim
139 words
A process for the production of neohexanol of a purity of above 99%, a chlorine content of less than 10 ppm, and a sulfur content of less than 5 ppm, comprising esterifying 3,3-dimethylbutyric acid of a chlorine content below 650 ppm with an alkanol of a normal boiling point above 117° C.; separating the ester by distillation into chlorine rich fractions of chlorine contents above 10 ppm and chlorine poor fractions of chlorine contents below 10 ppm, during which step the chlorine content of the distillate or the sump is continuously controlled by sampling; hydrogenating the ester with a chlorine content below 10 ppm to form neohexanol, over a barium-activated copper chromite catalyst under a hydrogen pressure of 200-300 bar, at a temperature of 120°-220° C., and with a catalyst load of 0.05-1.0 liter of hydrogenation feed/liter of catalyst.hour.
Claim 3
Dependent Claim
56 words
A process of claim 1 further comprising, prior to the esterification step, separating the 3,3-dimethylbutyric acid by distillation into a chlorine rich fraction of a chlorine content above 650 ppm and a chlorine poor fraction of a chlorine content below 650 ppm, during which step the chlorine content of the distillate is continuously controlled by sampling.
Claim 4
Dependent Claim
71 words
A process of claim 1 further comprising, prior to the esterification step, separating the 3,3-dimethylbutyric acid by distillation into a chlorine rich fraction of a chlorine content above 100 ppm and a chlorine poor fraction of a chlorine content below 100 ppm, during which step the chlorine content of the distillate is continuously controlled by sampling, and then only the latter chlorine poor fraction is passed onto the subsequent esterification step.
Claim 5
Dependent Claim
14 words
A process of claim 1 or 3, wherein the alkanol is an octyl alcohol.
Claim 6
Dependent Claim
14 words
A process of claim 1 or 3 wherein the alkanol is n-octanol or 2-ethyl-1-hexanol.
Claim 7
Dependent Claim
19 words
A process of claim 1 or 2 wherein the hydrogenation is carried out up to a conversion of 80-99%.
Claim 8
Dependent Claim
17 words
A process of claim 4 wherein the hydrogenation is carried out up to a conversion of 80-99%.
Claim 9
Dependent Claim
17 words
A process of claim 5 wherein the hydrogenation is carried out up to a conversion of 80-99%.
Claim 10
Dependent Claim
10 words
A process of claim 6 wherein said conversion is 80-97%.
Claim 11
Dependent Claim
17 words
A process of claim 4 wherein the hydrogenation is carried out up to a conversion of 80-97%.
Claim 12
Dependent Claim
17 words
A process of claim 5 wherein the hydrogenation is carried out up to a conversion of 80-97%.
Claim 13
Dependent Claim
26 words
A process of claim 1 or 2 wherein the alkanol is n-butanol, n-pentanol, an isopentanol, n-hexanol, an isohexanol, n-heptanol, an isoheptanol, n-octanol, 2-ethyl-1-hexanol, or other isooctanol.
Claim 14
Dependent Claim
14 words
A process of claim 1 or 2 wherein the hydrogenation temperature is 160°-180° C.
Claim 15
Dependent Claim
146 words
A process for the preparation of neohexanol comprising, preparing neohexanol of a purity above 99%, a chlorine content <10 ppm and a sulfur content <5 ppm by a process comprising esterifying 3,3-dimethylbutyric acid of a chlorine content below 650 ppm with an alkanol of a normal boiling point above 117° C.; separating the ester by distillation into chlorine rich fractions of chlorine contents above 10 ppm and chlorine poor fractions of chlorine contents below 10 ppm, during which step the chlorine content of the distillate or the sump is continuously controlled by sampling; hydrogenating the ester with a chlorine content below 10 ppm to form neohexanol, over a barium-activated copper chromite catalyst under a hydrogen pressure of 200-300 bar, at a temperature of 120°-220° C., and with a catalyst load of 0.05-1.0 liter of hydrogenation feed/liter of catalyst.hour; and dehydrogenating the resultant neohexanol to form neohexanal.
Claim 16
Dependent Claim
146 words
A process for the preparation of neohexanol comprising, preparing neohexanol of a purity above 99%, a chlorine content <10 ppm and a sulfur content <5 ppm by a process comprising esterifying 3,3-dimethylbutyric acid of a chlorine content below 650 ppm with an alkanol of a normal boiling point above 117° C.; separating the ester by distillation into chlorine rich fractions of chlorine contents above 10 ppm and chlorine poor fractions of chlorine contents below 10 ppm, during which step the chlorine content of the distillate or the sump is continuously controlled by sampling; hydrogenating the ester with a chlorine content below 10 ppm to form neohexanol, over a barium-activated copper chromite catalyst under a hydrogen pressure of 200-300 bar, at a temperature of 120°-220° C., and with a catalyst load of 0.05-1.0 liter of hydrogenation feed/liter of catalyst.hour; and dehydrogenating the resultant neohexanol to form neohexanal.
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) | 1987-02-20 | 1987-08-22 | 1988-02-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-02-20 | 1991-08-22 | 1992-02-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-02-20 | 1995-08-22 | 1996-02-21 | $7700.00 | Window Closed / Lapsed |