DE854353C - Process for the preparation of 3-oxopimelic acid esters - Google Patents
Process for the preparation of 3-oxopimelic acid estersInfo
- Publication number
- DE854353C DE854353C DED4249D DED0004249D DE854353C DE 854353 C DE854353 C DE 854353C DE D4249 D DED4249 D DE D4249D DE D0004249 D DED0004249 D DE D0004249D DE 854353 C DE854353 C DE 854353C
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- preparation
- alcohol
- oxopimelic
- acid
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 3-Oxopimelinsäureestern Es ist bekannt, daß man Furfurylacrylsäure durch Eihitzen in Äthylalkohol unter Einleiten von Salzsäuregas in den 1)iäthylester der 3-OxoPimelinsäure überfuhren kann. Bei diesem Verfahren gelangt man jedoch nur zu einer Ausbeute an 3-Oxo-1>imelinsäureester von etwa 5o % der Theorie.Process for the preparation of 3-oxopimelic acid esters It is known that one furfuryl acrylic acid by heating in ethyl alcohol while passing in hydrochloric acid gas can be converted into the 1) ethyl ester of 3-oxopimelic acid. In this procedure However, only a yield of 3-oxo-1> imelic acid ester of about 50 is obtained % of theory.
Es wurde nun gefunden, daß man wesentlich bessere Ausbeuten an 3-Oxol)imelinsäureestern und damit der Säure selbst und eine Verkürzung der Reaktionsdauer erhält, wenn man an Stelle des Äthylalkohols einen über 9o° siedenden acyclischen oder evclischen Alkohol, wie z.13. Propylalkohol, Butylalkohol, Hexylalkohol usw., Cyclohexylalkohol, Methylcyclohexylalkohole, Benzylalkohol, Hexahydrobenzylalkohol, Methoxyäthylalkohol, Tetrahydrofurfurylalkohol u. dgl. verwendet. :Man erhält dann Ausbeuten an entsprechenden Ketopimelinsäureestern von etwa 8o bis 9o °/o der Theorie.It has now been found that significantly better yields of 3-oxol) imelic acid esters are obtained and thus the acid itself and a shortening of the reaction time obtained if one instead of ethyl alcohol an acyclic or evclic boiling point above 90 ° Alcohol, such as 13. Propyl alcohol, butyl alcohol, hexyl alcohol, etc., cyclohexyl alcohol, Methylcyclohexyl alcohol, benzyl alcohol, hexahydrobenzyl alcohol, methoxyethyl alcohol, Tetrahydrofurfuryl alcohol and the like are used. : Yields of corresponding are then obtained Ketopimelic acid esters from about 80 to 90% of theory.
Beispiel In eine Aufschlämmung von il4o Gewichtsteilen Furfurylacrylsäure in 76o Gewichtsteilen Butanol wird ohne zu kühlen Chlorwasserstoffgas im lebhaften Strome bis zur Sättigung eingeleitet, dann wird die Temperatur langsam auf ioo° gebracht und unter weiterem Einleiten von Chlorwasserstoffgas 5 Stunden gehalten.Example In a slurry of 100 parts by weight of furfuryl acrylic acid in 76o parts by weight of butanol, hydrogen chloride gas becomes brisk in the brisk without cooling Currents initiated until saturation, then the temperature is slowly brought to 100 ° and held for 5 hours with further introduction of hydrogen chloride gas.
Nachdem das erhaltene Reaktionsgemisch mit eiskalter Kochsalzlösung neutral gewaschen ist, wird das Butanol im schwachen Vakuum abdestilliert und der Rückstand bei i mm Hg-Druck destilliert, wobei zwischen 165° und 17o° 241 Gewichtsteile 3-Oxopimelinsäuredibutylester übergehen, was 83 % der Theorie entspricht. Aus dem Waschwasser konnten noch 2o Gewichtsteile 3-Oxopimelinsäure isoliert werden.After the reaction mixture obtained with ice-cold saline solution is washed neutral, the butanol is distilled off in a weak vacuum and the Residue distilled at i mm Hg pressure, between 165 ° and 17o ° 241 parts by weight 3-Oxopimelinsäuredibutylester pass over, which corresponds to 83% of theory. From the Wash water could still be isolated 20 parts by weight of 3-oxopimelic acid.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED4249D DE854353C (en) | 1943-02-20 | 1943-02-20 | Process for the preparation of 3-oxopimelic acid esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED4249D DE854353C (en) | 1943-02-20 | 1943-02-20 | Process for the preparation of 3-oxopimelic acid esters |
Publications (1)
Publication Number | Publication Date |
---|---|
DE854353C true DE854353C (en) | 1952-11-04 |
Family
ID=7030908
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DED4249D Expired DE854353C (en) | 1943-02-20 | 1943-02-20 | Process for the preparation of 3-oxopimelic acid esters |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE854353C (en) |
-
1943
- 1943-02-20 DE DED4249D patent/DE854353C/en not_active Expired
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