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US3923867A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for producing monomethyl terephthalate

Assignee: Dynamit Nobel AG
•
Filing: 1972-06-05
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Granted: 1975-12-02
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Expires: 1992-06-05
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Abstract

Abstract A method for producing monomethyl terephthalate, including dissolving in p-xylene a polyvalent heavy metal salt catalyst for the oxidation of p-xylene to p-toluic acid, oxidizing the resulting p-xylene at a temperature between 90* and 140*C, a pressure between 1 and 15 atmospheres, and an oxygen partialpressure of less than 3 atmospheres to p-toluic acid, stopping the oxidation of the p-xylene at the point of maximum achievable selectivity for p-toluic acid, esterifying the resulting p-toluic acid to the methyl ester of p-toluic acid, dissolving in the resulting methyl ester of p-toluic acid a polyvalent heavy metal salt catalyst for the oxidation of the methyl ester of p-toluic acid to monomethyl terephthalate, oxidizing the resulting methyl ester of p-toluic acid at temperatures between 130* and 200*C and pressures between 1 and 6 atmospheres to monomethyl terephthalate, stopping the oxidation of the methyl ester of ptoluic acid at the point of maximum achievable selectivity for monomethyl terephthalate, and purifying the resulting monomethyl terephthalate.

Inventors

  • 👤 Manfred Baerns
  • 👤 Bruno Beck
  • 👤 Karl Ludwig Schmid
  • 👤 Hubert Machacek
  • 👤 Gunther Beige
  • 👤 Heinz Nogge

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 17:47
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/16; C07C51/21; C07C51/255; C07C51/265

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 291 words
METHOD FOR PRODUCING HIGH-PURITY MONOMTHYL TEREPHTHALATE SUITABLE DIRECTLY AS A STARTINF PRODUCT FOR THE PRODUCTION OF POLYESTER FIBERS, COMPRISING THE FOLLOWING PROCESS STEPS: A. OXIDIZING P-XYLENE TO P-TOLUIC ACID BY REACTING SAID PXYLENE WITH AN OXYGEN CONTAINING GAS IN A GAS-LIQUID CONTACT SYSTEM AT A TEMPERATURE BETWEEN 90* AND 130*C, A PRESSURE BETWEEN 3 AND 15 ATMOSPHERES, IN THE PRESENCE OF A POLYVALENT HEAVY METAL SALT AS THE OXIDATION CATALYST, AND FOR A TIME SUCH THAT THE CONVERSION OF SAID P-XYLENE TO SAID P-TOLUIC ACID IS BETWEEN 15 AND 60 PERCENT; B. REACTING THE P-TOLUIC ACID FROM STEP (A) WITH METHANOL IN A FIRST ESTERIFICATION STAGE AT A TEMPERATURE BETWEEN 150* AND 230*C AND A PRESSURE BETWEEN 15 AND 60 ATMOSPHERES AND THEN REACTING THE RESIDUAL P-TOLUIC ACID SUBSTANTIALLY COMPLETELY TO P-TOLUIC ACID METHYL ESTER BY COUNTERCURRENT CONTACT WITH GASEOUS METHANOL AT TEMPERATURES BETWEEN 220* AND 260*C AND PRESSURES AT WHICH SAID METHANOL IS SUBSTANTIALLY IN VAPOR FORM; C. OXIDIZING P-TOLUIC ACID METHYL ESTER FROM STEP (B) WITH AN OXYGEN CONTAINING GAS IN A GAS-LIWUID SYSTEM AT A TEMPERATURE BETWEEN 140* AND 170*C, PRESSURES FROM 1 UP TO 6 ATMOSPHERES, IN THE PRESENCE OF A POLYVALENT HEAVY METAL SALT AS THE OXIDATION CATALYST, AND FOR A TIME SUCH THAT BETWEEN 20 AND 45 PERCENT OF SAID METHYL ESTER IS CONVERTED TO MONOMETHYL TEREPHTHALATE; D. SEPARATING THE CRYSTALLINE MONOMETHYL TEREPHTHALATE REACTION PRODUCT FROM THE REACTION MIXTURE FOLLOWING STEP (C); E. DISSOLVING SAID MONOMETHYL TEREPHTHALATE IN A SOLVENT WHICH EXHIBITS A STRONG TEMPERATURE DEPENDENCE FOR THE SOLUBILITY OF MONOMETHYL TEREPHTHALATE, AND CONTACTING THE RESULTING SOLUTION WHICH ACTIVATED CARBON TO REMOVE COLOR IMPURITIES THEREFROM; F. COOLING THE THUS-TREATED SOLUTION TO RECRYSTALLIZE THE MONOMETHYL TEREPHTHALATE THEREFROM; AND G. RECOVERING THE RESULTING HIGH-PURITY MONOMETHYL TEREPHTHALATE PRODUCT.
Claim 2
Dependent Claim 291 words
METHOD FOR PRODUCING HIGH-PURITY MONOMTHYL TEREPHTHALATE SUITABLE DIRECTLY AS A STARTINF PRODUCT FOR THE PRODUCTION OF POLYESTER FIBERS, COMPRISING THE FOLLOWING PROCESS STEPS: A. OXIDIZING P-XYLENE TO P-TOLUIC ACID BY REACTING SAID PXYLENE WITH AN OXYGEN CONTAINING GAS IN A GAS-LIQUID CONTACT SYSTEM AT A TEMPERATURE BETWEEN 90* AND 130*C, A PRESSURE BETWEEN 3 AND 15 ATMOSPHERES, IN THE PRESENCE OF A POLYVALENT HEAVY METAL SALT AS THE OXIDATION CATALYST, AND FOR A TIME SUCH THAT THE CONVERSION OF SAID P-XYLENE TO SAID P-TOLUIC ACID IS BETWEEN 15 AND 60 PERCENT; B. REACTING THE P-TOLUIC ACID FROM STEP (A) WITH METHANOL IN A FIRST ESTERIFICATION STAGE AT A TEMPERATURE BETWEEN 150* AND 230*C AND A PRESSURE BETWEEN 15 AND 60 ATMOSPHERES AND THEN REACTING THE RESIDUAL P-TOLUIC ACID SUBSTANTIALLY COMPLETELY TO P-TOLUIC ACID METHYL ESTER BY COUNTERCURRENT CONTACT WITH GASEOUS METHANOL AT TEMPERATURES BETWEEN 220* AND 260*C AND PRESSURES AT WHICH SAID METHANOL IS SUBSTANTIALLY IN VAPOR FORM; C. OXIDIZING P-TOLUIC ACID METHYL ESTER FROM STEP (B) WITH AN OXYGEN CONTAINING GAS IN A GAS-LIWUID SYSTEM AT A TEMPERATURE BETWEEN 140* AND 170*C, PRESSURES FROM 1 UP TO 6 ATMOSPHERES, IN THE PRESENCE OF A POLYVALENT HEAVY METAL SALT AS THE OXIDATION CATALYST, AND FOR A TIME SUCH THAT BETWEEN 20 AND 45 PERCENT OF SAID METHYL ESTER IS CONVERTED TO MONOMETHYL TEREPHTHALATE; D. SEPARATING THE CRYSTALLINE MONOMETHYL TEREPHTHALATE REACTION PRODUCT FROM THE REACTION MIXTURE FOLLOWING STEP (C); E. DISSOLVING SAID MONOMETHYL TEREPHTHALATE IN A SOLVENT WHICH EXHIBITS A STRONG TEMPERATURE DEPENDENCE FOR THE SOLUBILITY OF MONOMETHYL TEREPHTHALATE, AND CONTACTING THE RESULTING SOLUTION WHICH ACTIVATED CARBON TO REMOVE COLOR IMPURITIES THEREFROM; F. COOLING THE THUS-TREATED SOLUTION TO RECRYSTALLIZE THE MONOMETHYL TEREPHTHALATE THEREFROM; AND G. RECOVERING THE RESULTING HIGH-PURITY MONOMETHYL TEREPHTHALATE PRODUCT.
Claim 3
Dependent Claim 58 words
A method as claimed in claim 1 wherein the catalyst in step (a) is a cobalt salt in a concentration between 10 5 and 10 2 gram atom cobalt/mole of p-xylene and the catalyst in step (c) is a cobalt salt in a concentration of 10 5 and 10 3 gram atom cobalt/mole of p-toluic acid methyl ester.
Claim 4
Dependent Claim 32 words
A method as claimed in claim 1 wherein the temperature during the first stage esterification of step (b) is between 200* and 230*C and the pressure is between 40 and 60 atmospheres.
Claim 5
Dependent Claim 18 words
A method as claimed in claim 1 wherein the oxygen containing gas is in the form of air.

References Cited (Backward Citations)

US2653165A Cited
US2813119A Cited
US2834801A Cited
US3076019A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-12-01 1979-06-02 1979-12-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-12-01 1983-06-02 1983-12-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-12-01 1987-06-02 1987-12-02 $7700.00 Window Closed / Lapsed

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