DE515306C - Process for the preparation of esters - Google Patents
Process for the preparation of estersInfo
- Publication number
- DE515306C DE515306C DEI27320D DEI0027320D DE515306C DE 515306 C DE515306 C DE 515306C DE I27320 D DEI27320 D DE I27320D DE I0027320 D DEI0027320 D DE I0027320D DE 515306 C DE515306 C DE 515306C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- preparation
- esters
- glycol
- 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
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Estern Bekanntlich reagieren Alkylenoxyde mit anorganischen Säuren sehr leicht unter Bildung einheitlicher Produkte; so gibt z. B. Äthylenoxyd mit Salzsäure glatt Äthylenchlorhydrin. Auch organische Säuren oder deren Anhydride setzen sich mit Alkylenoxyden zu Estern um. So erhält man aus Äthylenoxyd und Essigsäure unter bestimmten Bedingungen in Abwesenheit von Katalysatoren Glykoltnono- ünd -diacetat. Im allgemeinen erhält man jedoch nach dieser Arbeitsweise in geringer Ausbeute uneinheitliche Produkte, die zwecks Gewinnung der Einzelbestandteile fraktioniert destilliert werden müssen. Auch bei Verwendung von Schwefelsäure als Katalysator werden keine besseren Ergebnisse erzielt.Process for the preparation of esters It is known that alkylene oxides react with inorganic acids very easily with the formation of uniform products; so there z. B. Ethylene oxide with hydrochloric acid smooth ethylene chlorohydrin. Organic acids too or their anhydrides react with alkylene oxides to form esters. So you get out Ethylene oxide and acetic acid under certain conditions in the absence of catalysts Glycol mono and diacetate. In general, however, one obtains this procedure inconsistent products in low yield for the purpose of extracting the individual components must be fractionally distilled. Even when using sulfuric acid as Catalyst will not give better results.
Es wurde nun gefunden, daß man in einheitlicher Reaktion Monoester des Glykols oder seiner Homologen in im allgemeinen praktisch quantitativer Ausbeute erhalten kann, wenn man halogenfreie Alkylenoxyde auf organische Säuren oder deren Anhydride bei erhöhten Temperaturen in Gegenwart von Salzen organischer Säuren, zweckmäßig der als Veresterungskomponente verwendeten Säure, einwirken läßt.It has now been found that monoesters can be obtained in a uniform reaction of glycol or its homologues in generally practically quantitative yield can be obtained when using halogen-free alkylene oxides on organic acids or their Anhydrides at elevated temperatures in the presence of salts of organic acids, expediently the acid used as the esterification component can act.
Beispiel i _ Man erhitzt äquimolekulare Mengen Essigsäure und Äthyienoxyd unter Zusatz von 3 °/o Natriumacetat auf etwa 12o°. Es entsteht Glykolmonoacetat in einer Ausbeute von etwa 95 °/o der Theorie.Example i _ Equimolecular amounts of acetic acid and ethylene oxide are heated with the addition of 3% sodium acetate to about 120 °. Glycol monoacetate is formed in a yield of about 95% of theory.
Beispiel e Zu einer siedenden Lösung von etwa 5 Gewichtsteilen essigsaurem Natrium und 93 Gewichtsteilen Eisessig fügt man unter Rückflußkühlung 59 Gewichtsteile Propylenoxyd zu. Man erhält in nahezu quantitativer Ausbeute Propylenglykolacetat.Example e To a boiling solution of about 5 parts by weight of acetic acid Sodium and 93 parts by weight of glacial acetic acid are added 59 parts by weight with reflux cooling Propylene oxide too. Propylene glycol acetate is obtained in an almost quantitative yield.
Beispiel 3 1o2 Gewichtsteile Valeriansäure werden mit 78 Gewichtsteilen Propylenoxyd unter Zusatz von 3 Gewichtsteilen valeriansaurem Natrium auf etwa i2o bis 15o° erhitzt. Man erhält in einer Ausbeute von 9o °4, bezogen auf Propylenoxyd, Propylenglykolmonovalerianat. Beispiel q.Example 3 1o2 parts by weight of valeric acid are mixed with 78 parts by weight Propylene oxide with the addition of 3 parts by weight of sodium valerate to about 12o heated to 15o °. One obtains in a yield of 90 ° 4, based on propylene oxide, Propylene glycol monovalerate. Example q.
In eine siedende Lösung von etwa 5 Gewichtsteilen buttersaurem Natrium in 93 Gewichtsteilen Eisessig leitet man unter Rückflußkühlung 59 Gewichtsteile Propylenoxyd ein. Man erhält in nahezu quantitativer Ausbeute Propylenglykolmonoacetat.In a boiling solution of about 5 parts by weight of sodium butyrate 59 parts by weight are passed into 93 parts by weight of glacial acetic acid with reflux cooling Propylene oxide. Propylene glycol monoacetate is obtained in an almost quantitative yield.
Beispiel s 256 Gewichtsteile Palmitinsäure werden unter Zusatz von 7,5 Gewichtsteilen Calciumpalmitat in einem Autoklaven geschmolzen. Man prellt unter Erhitzen auf 130 bis 15o° 92 Teile i, 2-Butylenoxyd ein und erhält mit nahezu quantitativer Ausbeute i, 2-Butyleng lykolmonopalmitat.Example s 256 parts by weight of palmitic acid are melted in an autoclave with the addition of 7.5 parts by weight of calcium palmitate. While heating to 130 ° to 150 °, 92 parts of i, 2-butylene oxide are bounced in and i, 2-butylene glycol monopalmitate is obtained with an almost quantitative yield.
Beispiel G In eine Schmelze von i22 Teilen Benzoesäure, der 4. Teile Natriumbenzoat zugesetzt wurden, werden unter Rückflußkühlung 59 Teile Propylenoxyd eingetragen. Man erhält in fast quantitativer Ausbeute Propylenglykolmonobenzoat.Example G In a melt of 222 parts of benzoic acid, the 4th part Sodium benzoate was added, 59 parts of propylene oxide are refluxed registered. Propylene glycol monobenzoate is obtained in an almost quantitative yield.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI27320D DE515306C (en) | 1926-01-30 | 1926-01-30 | Process for the preparation of esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI27320D DE515306C (en) | 1926-01-30 | 1926-01-30 | Process for the preparation of esters |
Publications (1)
Publication Number | Publication Date |
---|---|
DE515306C true DE515306C (en) | 1931-10-29 |
Family
ID=7186738
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEI27320D Expired DE515306C (en) | 1926-01-30 | 1926-01-30 | Process for the preparation of esters |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE515306C (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2446505A (en) * | 1946-04-12 | 1948-08-03 | Doughnut Corp | Method of inhibiting the growth of mold |
DE1144262B (en) * | 1958-03-06 | 1963-02-28 | Roehm & Haas Gmbh | Process for the preparation of AEthane-1, 2-diol and propane-1, 2-diol monoacrylate and monomethacrylate |
DE1147938B (en) * | 1959-04-30 | 1963-05-02 | Roehm & Haas Gmbh | Production of AEthane-1, 2-diol and propane-1, 2-diol monoacrylate and monomethacrylate |
-
1926
- 1926-01-30 DE DEI27320D patent/DE515306C/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2446505A (en) * | 1946-04-12 | 1948-08-03 | Doughnut Corp | Method of inhibiting the growth of mold |
DE1144262B (en) * | 1958-03-06 | 1963-02-28 | Roehm & Haas Gmbh | Process for the preparation of AEthane-1, 2-diol and propane-1, 2-diol monoacrylate and monomethacrylate |
DE1147938B (en) * | 1959-04-30 | 1963-05-02 | Roehm & Haas Gmbh | Production of AEthane-1, 2-diol and propane-1, 2-diol monoacrylate and monomethacrylate |
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