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DE497629C - Process for the hydrogenation of phthalic acid alkyl esters - Google Patents

Process for the hydrogenation of phthalic acid alkyl esters

Info

Publication number
DE497629C
DE497629C DEI31092D DEI0031092D DE497629C DE 497629 C DE497629 C DE 497629C DE I31092 D DEI31092 D DE I31092D DE I0031092 D DEI0031092 D DE I0031092D DE 497629 C DE497629 C DE 497629C
Authority
DE
Germany
Prior art keywords
hydrogenation
phthalic acid
alkyl esters
acid alkyl
hexahydrophthalic 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
Application number
DEI31092D
Other languages
German (de)
Inventor
Dr Theodor Goost
Dr Wilhelm Lommel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI31092D priority Critical patent/DE497629C/en
Application granted granted Critical
Publication of DE497629C publication Critical patent/DE497629C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
    • C07C61/09—Completely hydrogenated benzenedicarboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

Verfahren zur Hydrierung von Phthalsäurealkylestern Es wurde die bemerkenswerte Beobachtung gemacht, daß bei der Einwirkung von Wasserstoff unter Druck auf Phthalsäurealkylester in Gegenwart von Katalysatoren bei Temperaturen unter 25o0 sich Ester der Hexahydrophtlialsäure bilden. Der Verlauf des Wrfahrens war nicht vorauszusehen, da bei der analogen Hydrierung des Phthalsäureanhydrids nicht der Kern hydriert, soildern eine CO-Gruppe reduziert wird, wie es in der Patenschrift 368 414 beschrieben ist. Hydrierungsversnche bei :25oc> und darüber sind in den Berichten der Deutsch-en Chem. Ges. 41 (1908), Seite 1002/03 erwähnt, führten aber nicht zu Hexahydrophthalsäureestern. Die Produkte sollen technische Verwendung als Lösungsmittel und für andere Zwecke finden.Process for the hydrogenation of alkyl phthalates The remarkable observation was made that the action of hydrogen under pressure on alkyl phthalates in the presence of catalysts at temperatures below 250 produces esters of hexahydrophthalic acid. The course of the Wrfahrens was not foreseeable because of the non-hydrogenated core in the analogous hydrogenation of phthalic anhydride, soildern a CO group is reduced as described in the patent specification 368,414. Hydrogenation verses at: 25oc> and above are mentioned in the reports of Deutsch-en Chem. Ges. 41 (1908), page 1002/03, but did not lead to hexahydrophthalic acid esters. The products are intended to be used industrially as solvents and for other purposes.

B e i s p i e 1 3oo Gewichtsteile Phthalsätirediäthylester werden Mit 2'/, Gewichtsteilen Nickel-Katalysator unter Wasserstoffdruck erhitzt. Bei einer allmählichen Steigerung des Druckes auf ioo Atni. und Erhöhung der Temperatur auf 2300 werden in 31, Stunden über 89 0/, Hexahydrophthalsäurediäthylester gebildet. Dieser stellt ein angenehm riechendes Öl dar, das bei 13 mm bei 138 bis 1400 siedet. Durch Verseifung erhält man die Hexahydrophthalsäure.B ice p y 1 3oo parts by weight Phthalsätirediäthylester are / is heated with 2 'parts by weight of nickel catalyst under hydrogen pressure. With a gradual increase in pressure to 100 Atni. and raising the temperature to 2300 , more than 89 0 /, hexahydrophthalic acid diethyl ester is formed in 31. hours. This is a pleasant smelling oil that boils at 13 mm at 138 to 1400. The hexahydrophthalic acid is obtained by saponification.

Unter den gleichen Bedingungen läßt sich der Phthalsäuredimethylester zu Hexahyldrophthalsäuredimethvlester hydrieren und durch Destillation reinigen. (Siedepunkt io8 bis iii' bei i2mm.)The dimethyl phthalate can be obtained under the same conditions Hydrogenate to dimethyl hexahydrophthalate and purify by distillation. (Boiling point io8 to iii 'at i2mm.)

Claims (1)

PATENTANSPRUCH: Verfahren zur Hydrierung von Phthalsäurealkylestern, dadurch gekennzeichnet, daß man sie mit Wasserstoff unter Druck in Gegenwart von Katalysatoren auf höhere Temperaturen, die jedoch 25o' nicht erreichen, erhitzt. PATENT CLAIM: Process for the hydrogenation of alkyl phthalates, characterized in that they are heated with hydrogen under pressure in the presence of catalysts to higher temperatures which, however, do not reach 25o '.
DEI31092D 1927-05-05 1927-05-05 Process for the hydrogenation of phthalic acid alkyl esters Expired DE497629C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI31092D DE497629C (en) 1927-05-05 1927-05-05 Process for the hydrogenation of phthalic acid alkyl esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI31092D DE497629C (en) 1927-05-05 1927-05-05 Process for the hydrogenation of phthalic acid alkyl esters

Publications (1)

Publication Number Publication Date
DE497629C true DE497629C (en) 1930-05-09

Family

ID=7187783

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI31092D Expired DE497629C (en) 1927-05-05 1927-05-05 Process for the hydrogenation of phthalic acid alkyl esters

Country Status (1)

Country Link
DE (1) DE497629C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7855340B2 (en) 2001-09-25 2010-12-21 Exxonmobil Chemical Patents Inc. Plasticised polyvinyl chloride

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7855340B2 (en) 2001-09-25 2010-12-21 Exxonmobil Chemical Patents Inc. Plasticised polyvinyl chloride

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