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US4117251A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for preparing straight chain primary alcohols from 1-bromoalkanes

Assignee: Huels AG
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Filing: 1977-03-17
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Granted: 1978-09-26
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Expires: 1997-03-17
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Abstract

Abstract Straight-chain, primary alcohols are prepared by reacting straight-chain 1-bromoalkanes having 6 to 20 carbon atoms with alkali salts of monocarboxylic acids having 4 to 22 carbon atoms in the presence of 1 to 10 mole percent of monocarboxylic acids or alcohols based upon the alkali salt of the carboxylic acid and at temperatures ranging from 150° to 300° C. The esters formed are saponified in alkaline medium to the straight-chain, primary alcohols and separated.

Inventors

  • 👤 Manfred Kaufhold
  • 👤 Gottfried Bankwitz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 21:27
CPC Classifications
C; C07; C07C; C07C29/00

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 97 words
In a process for preparing straight-chain, primary alcohols having 6-20 carbon atoms, the improvement comprising reacting at a temperature of about 150° to 300° C. straight-chain 1-bromoalkanes having 6 to 20 carbon atoms with alkali salts of alkanoic acids having 4 to 22 carbon atoms in the presence of 1 to 10 mole percent of alkanoic acids having 4 to 22 carbon atoms based on said alkali salts of the alkanoic acids to form esters, saponifying said esters in an alkaline medium to form straight-chain, primary alcohols having 6-20 carbon atoms and separating said straight-chain, primary alcohols.
Claim 2
Dependent Claim 97 words
In a process for preparing straight-chain, primary alcohols having 6-20 carbon atoms, the improvement comprising reacting at a temperature of about 150° to 300° C. straight-chain 1-bromoalkanes having 6 to 20 carbon atoms with alkali salts of alkanoic acids having 4 to 22 carbon atoms in the presence of 1 to 10 mole percent of alkanoic acids having 4 to 22 carbon atoms based on said alkali salts of the alkanoic acids to form esters, saponifying said esters in an alkaline medium to form straight-chain, primary alcohols having 6-20 carbon atoms and separating said straight-chain, primary alcohols.
Claim 3
Dependent Claim 18 words
The process of claim 1, wherein said alkali salts of alkanoic acids have 4 to 10 carbon atoms.
Claim 4
Dependent Claim 15 words
The process of claim 2, wherein said reacting temperature is about 200° to 250° C.
Claim 5
Dependent Claim 129 words
A process for preparing straight-chain, primary alcohols having 6-20 carbon atoms, comprising: (a) hydrobrominating α olefins having 6 to 20 carbon atoms in the presence of UV light or peroxides to form brominated α olefins; (b) fractionally distilling said brominated α olefins; (c) separating straight-chain 1-bromoalkanes having 6 to 20 carbon atoms as sump product; (d) reacting said straight-chain 1-bromoalkanes with alkali salts of alkanoic acids having 4 to 22 carbon atoms in the presence of 1 to 10 mole percent of alkanoic acids having 4 to 22 carbon atoms and at a temperature of about 150° to 300° C. to form esters; (e) saponifying said esters in an alkaline medium to form said straight-chain, primary alcohols having 6-20 carbon atoms; and (f) separating said straight chain, primary alcohols.
Claim 6
Dependent Claim 129 words
A process for preparing straight-chain, primary alcohols having 6-20 carbon atoms, comprising: (a) hydrobrominating α olefins having 6 to 20 carbon atoms in the presence of UV light or peroxides to form brominated α olefins; (b) fractionally distilling said brominated α olefins; (c) separating straight-chain 1-bromoalkanes having 6 to 20 carbon atoms as sump product; (d) reacting said straight-chain 1-bromoalkanes with alkali salts of alkanoic acids having 4 to 22 carbon atoms in the presence of 1 to 10 mole percent of alkanoic acids having 4 to 22 carbon atoms and at a temperature of about 150° to 300° C. to form esters; (e) saponifying said esters in an alkaline medium to form said straight-chain, primary alcohols having 6-20 carbon atoms; and (f) separating said straight chain, primary alcohols.
Claim 7
Dependent Claim 20 words
The process of claim 4, wherein step (d) is carried out at a temperature of about 200° to 250° C.
Claim 8
Dependent Claim 21 words
The process of claim 4, wherein step (d) is carried out for a period of about 10 minutes to 5 hours.
Claim 9
Dependent Claim 20 words
The process of claim 4, wherein step (d) is carried out for a period of about 1 to 2 hours.
Claim 10
Dependent Claim 44 words
The process of claim 4, wherein said 1-bromoalkanes have a bromine content of about 22 to 46 percent and are selected from the group consisting of 1-bromohexane 1-bromoheptane, 1-bromooctane, 1-bromononane, 1-bromodecane, 1-bromoundecane, 1-bromododecane, 1-bromotridecane, 1-bromotetradecane, 1-bromopentadecane, 1-hexadecane, 1-bromoheptadecane, 1-bromooctadecane, 1-bromononadecane, 1-bromoeicosane and mixtures thereof.

References Cited (Backward Citations)

US1459971A Cited
US3655701A Cited
US3968177A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-09-25 1982-03-27 1982-09-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-09-25 1986-03-27 1986-09-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-09-25 1990-03-27 1990-09-26 $7700.00 Window Closed / Lapsed

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