DE971421C - Process for the production of phthalic acid monomethyl ester - Google Patents

Process for the production of phthalic acid monomethyl ester

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Publication number
DE971421C
DE971421C DEI4315A DEI0004315A DE971421C DE 971421 C DE971421 C DE 971421C DE I4315 A DEI4315 A DE I4315A DE I0004315 A DEI0004315 A DE I0004315A DE 971421 C DE971421 C DE 971421C
Authority
DE
Germany
Prior art keywords
phthalic acid
production
monomethyl ester
acid monomethyl
ester
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
DEI4315A
Other languages
German (de)
Inventor
Dipl-Chem Ewald Katzschmann
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.)
Imhausen Werke GmbH
Original Assignee
Imhausen Werke GmbH
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 Imhausen Werke GmbH filed Critical Imhausen Werke GmbH
Priority to DEI4315A priority Critical patent/DE971421C/en
Application granted granted Critical
Publication of DE971421C publication Critical patent/DE971421C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B35/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving a change in the type of bonding between two carbon atoms already directly linked
    • C07B35/04—Dehydrogenation
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

(WiGBl. S. 17S)(WiGBl. P. 17S)

AUSGEGEBEN AM 29. JANUAR 1959ISSUED JANUARY 29, 1959

14315 IVb /1214315 IVb / 12

Zusatz zum Patent 949Addendum to patent 949

Die Erfindung betrifft eine weitere Ausbildung des Verfahrens nach Patent 949 564.The invention relates to a further development of the method according to patent 949 564.

Gegenstand des Patents 949 564 ist ein Verfahren zur Herstellung von Terephthalsäuremonomethylester, das darin besteht, daß p-Toluylsäuremethylester mit Sauerstoff oder sauerstoff hakigen Gasen bei erhöhter Temperatur in flüssiger Phase, gegebenenfalls unter Druck, vorteilhaft in Gegenwart von Katalysatoren, wie Schwermetallsalzen, insbesondere Kobalt- oder Mangansalzen, oxydiert wird.The subject of patent 949 564 is a process for the production of terephthalic acid monomethyl ester, that consists in that p-toluic acid methyl ester with oxygen or oxygen-containing gases at elevated temperature in the liquid phase, if appropriate under pressure, advantageously in the presence of catalysts such as heavy metal salts, in particular Cobalt or manganese salts, is oxidized.

In einer besonderen Ausführungsform wird nur ein Teil des p-Toluylsäuremethylesters oxydiert, der gebildete Terephthalsäuremonomethylester, zweckmäßig nach Abkühlen, mechanisch abgetrennt und die Oxydation des pestlichen Toluylsäuremethylesters fortgesetzt.In a particular embodiment, only part of the p-toluic acid methyl ester is oxidized, the monomethyl terephthalate formed, expediently after cooling, separated mechanically and the oxidation of the pestal toluic acid methyl ester continued.

Es wurde nun gefunden, daß sich der Methylester der o-Toluylsäure auf dieselbe Weise zu dem Phthalsäuremonomethylester oxydieren läßt. Als Katalysatoren eignen sich auch hierbei die für die Oxy- ao dation mit gasförmigem Sauerstoff bekannten, insbesondere die Salze von Metallen, die, wie Kobalt, Mangan, Eisen oder Quecksilber, in mehreren Wertigkeitsstufen aufzutreten vermögen.It has now been found that the methyl ester of o-toluic acid converts itself in the same way to the phthalic acid monomethyl ester can oxidize. Suitable catalysts here are also those known for oxy ao dation with gaseous oxygen, in particular the salts of metals, such as cobalt, manganese, iron or mercury, in several Are able to occur.

Auch im Falle des o-Toluylsäuremethylesters ist der entstehende Phthalsäuremonomethylester im Reaktionsgemisch nur begrenzt löslich und scheidet sich beim Abkühlen in leicht filtrierbarer Form ab.Also in the case of methyl o-toluate the phthalic acid monomethyl ester formed has only limited solubility in the reaction mixture and separates when it cools down in an easily filterable form.

Der erfindungsgemäß hergestellte Phthalsäuremonomethylester ist ein für die Industrie der Weichmacher, Kunstharze usw. wertvolles Produkt. The phthalic acid monomethyl ester prepared according to the invention is one for the industry Plasticizers, synthetic resins, etc. valuable product.

809 715/51809 715/51

Beispielexample

iooo g o-Toluylsäuremethyl'SSter werden mit 2 g der Kobaltsalze der Fettsäuren mit 6 bis io C-Atomen versetzt und mit ι 1 Luft/Min, bei 130 bis 1400C oxydiert. Es wird unter Rückfluß gearbeitet und das Kondensat nac'h Abscheidung des Reaktionswassers in das Oxydationsgefäß zurückgeführt. Nach 68 Stunden ist die Säurezahl von 0,5 auf 142 gestiegen, die Verseifungszahl von 373 auf 481. Das Oxydationsgemisch wird abgekühlt und die ausgeschiedenen Kristalle abgesaugt, wobei 655 g flüssige Anteile und 330 g feste Anteile erhalten werden; die flüssigen'Anteile werden nach Auffüllung mit frischem o-Toluylsäuremethylester auf iooo g wieder der Oxydation unterworfen. Die festen Anteile erweisen sich als ein Gemisch aus Phthalsäuremonomethylester, Phthalsäure und Phthalsäureanhydrid. Man kann das Gemisch mit Methanol waschen und den Rückstand danach mit Methanol weiterverestern; bei der anschließenden Destillation des Veresterungsproduktes werden 280 g reiner Phthalsäuredimethylester erhalten.iooo g o-Toluylsäuremethyl'SSter with 2 g of cobalt salts of fatty acids having 6 to io carbon atoms and the mixture oxidized with ι 1 air / min, at 130 to 140 0 C. The process is carried out under reflux and the condensate is returned to the oxidation vessel after the water of reaction has been separated off. After 68 hours the acid number has risen from 0.5 to 142 and the saponification number from 373 to 481. The oxidation mixture is cooled and the crystals which have separated out are filtered off with suction, 655 g of liquid components and 330 g of solid components being obtained; the liquid components are subjected to oxidation again after being made up to 100 g with fresh methyl o-toluate. The solid fractions turn out to be a mixture of phthalic acid monomethyl ester, phthalic acid and phthalic anhydride. The mixture can be washed with methanol and the residue can then be further esterified with methanol; in the subsequent distillation of the esterification product, 280 g of pure phthalic acid dimethyl ester are obtained.

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Weiterbildung des Verfahrens nach Patent 949 564, dadurch gekennzeichnet, daß zur Herstellung von Phthalsäuremonomethylester als Ausgangsmaterial an Stelle von p-Toluylsäuremethylester o-Toluylsäuremethylester verwendet wird.Further development of the method according to patent 949 564, characterized in that for production of phthalic acid monomethyl ester as starting material instead of p-toluic acid methyl ester o-Toluic acid methyl ester used will. In Betracht gezogene Druckschriften:
Britische Patentschrift Nr. 623 836;
USA.-Patentschrift Nr. 2531 173;
Beilsteins Handbuch der organ. Chemie X, I. Ergänzungswerk, S. 318.Considered publications:
British Patent No. 623,836;
U.S. Patent No. 2531 173;
Beilstein's handbook of organ. Chemie X, I. Supplementary work, p. 318. ©809 715/51 1.59© 809 715/51 1.59
DEI4315A 1951-06-27 1951-06-27 Process for the production of phthalic acid monomethyl ester Expired DE971421C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI4315A DE971421C (en) 1951-06-27 1951-06-27 Process for the production of phthalic acid monomethyl ester

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI4315A DE971421C (en) 1951-06-27 1951-06-27 Process for the production of phthalic acid monomethyl ester

Publications (1)

Publication Number Publication Date
DE971421C true DE971421C (en) 1959-01-29

Family

ID=7184772

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI4315A Expired DE971421C (en) 1951-06-27 1951-06-27 Process for the production of phthalic acid monomethyl ester

Country Status (1)

Country Link
DE (1) DE971421C (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB623836A (en) * 1947-05-09 1949-05-24 Cyril Henry Bowden Manufacture of terephthalic acid
US2531173A (en) * 1947-11-17 1950-11-21 California Research Corp Preparation of terephthalic acid

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB623836A (en) * 1947-05-09 1949-05-24 Cyril Henry Bowden Manufacture of terephthalic acid
US2531173A (en) * 1947-11-17 1950-11-21 California Research Corp Preparation of terephthalic acid

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