GB735693A - Process for the manufacture of laevulinic acid esters - Google Patents
Process for the manufacture of laevulinic acid estersInfo
- Publication number
- GB735693A GB735693A GB18129/51A GB1812951A GB735693A GB 735693 A GB735693 A GB 735693A GB 18129/51 A GB18129/51 A GB 18129/51A GB 1812951 A GB1812951 A GB 1812951A GB 735693 A GB735693 A GB 735693A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohol
- laevulinate
- butyl
- furfuryl alcohol
- hydrogen chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
In the manufacture of laevulinic acid esters furfuryl alcohol is heated with another primary or a secondary alcohol under substantially anhydrous conditions with agitation in the presence of hydrogen chloride or hydrogen bromide as catalyst and the furfuryl alcohol is gradually added to the other alcohol at a rate such that at no time does the amount of unreacted furfuryl alcohol present in the reaction mixture exceed 2 per cent by volume of the other alcohol. Alcohol starting materials specified are methanol, ethanol, n-propanol, isopropanol, n-butanol, n-pentanol, isopentanol, n-hexanol, n-octanol, n-nonyl alcohol, n-decanol, an alkoxy-ethanol, e.g. b -methoxy- or b -ethoxy-ethanol, a cycloaliphatic alcohol, e.g. cyclohexanol and tetrahydrofurfuryl alcohol. The furfuryl alcohol may be added to the other alcohol while the latter is maintained at the boil, under atmospheric or reduced pressure. The process may be carried out by continuously withdrawing part of the reaction mixture during the reaction and adding furfuryl alcohol, fresh amounts of the alcohol to be esterified and hydrogen bromide or chloride to replace the constituents withdrawn. In examples methyl, ethyl, n-butyl, isobutyl, cyclohexyl, b -methoxy- and b -ethoxyethyl, tetrahydrofurfuryl, n-propyl, isopropyl, n-amyl, isoamyl, n-hexyl, n-octyl and n-nonyl laevulinates are obtained by gradually adding furfuryl alcohol to the appropriate alcohol boiling under reflux and containing hydrogen chloride (1-4, 6-9); (3) is repeated at a temperature below the boiling point of the alcohol; n-decyl laevulinate is prepared in a similar process (5) and n-butyl laevulinate is prepared by a similar process to (3) but using hydrogen bromide (9) and n-butyl laevulinate is obtained in a continuous process in which n-butanol containing hydrogen chloride is boiled under reflux whilst n-butanol containing hydrogen chloride and furfuryl alcohol are added and reaction mixture is withdrawn at the same rate. n-Butyl laevulinate is isolated by distillation (10). The esters may be converted to laevulinic acid by hydrolysis with water or salts by hydrolysis with metal compounds of alkaline reaction.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB18129/51A GB735693A (en) | 1951-07-31 | 1951-07-31 | Process for the manufacture of laevulinic acid esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB18129/51A GB735693A (en) | 1951-07-31 | 1951-07-31 | Process for the manufacture of laevulinic acid esters |
Publications (1)
Publication Number | Publication Date |
---|---|
GB735693A true GB735693A (en) | 1955-08-24 |
Family
ID=10107150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB18129/51A Expired GB735693A (en) | 1951-07-31 | 1951-07-31 | Process for the manufacture of laevulinic acid esters |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB735693A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102701978A (en) * | 2005-11-22 | 2012-10-03 | 塞格提斯有限公司 | Adducts of levulinic derivatives with epoxidized fatty acid esters and uses thereof |
EP2583696A3 (en) * | 2011-10-20 | 2013-06-12 | International Flavors & Fragrances Inc. | Low valatile reactive malodor counteractives and methods of use thereof |
US10226544B2 (en) | 2015-06-05 | 2019-03-12 | International Flavors & Fragrances Inc. | Malodor counteracting compositions |
-
1951
- 1951-07-31 GB GB18129/51A patent/GB735693A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102701978A (en) * | 2005-11-22 | 2012-10-03 | 塞格提斯有限公司 | Adducts of levulinic derivatives with epoxidized fatty acid esters and uses thereof |
EP2583696A3 (en) * | 2011-10-20 | 2013-06-12 | International Flavors & Fragrances Inc. | Low valatile reactive malodor counteractives and methods of use thereof |
US10226544B2 (en) | 2015-06-05 | 2019-03-12 | International Flavors & Fragrances Inc. | Malodor counteracting compositions |
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