GB681455A - Process for the production of aromatic dicarboxylic acids - Google Patents

Process for the production of aromatic dicarboxylic acids

Info

Publication number
GB681455A
GB681455A GB8568/50A GB856850A GB681455A GB 681455 A GB681455 A GB 681455A GB 8568/50 A GB8568/50 A GB 8568/50A GB 856850 A GB856850 A GB 856850A GB 681455 A GB681455 A GB 681455A
Authority
GB
United Kingdom
Prior art keywords
acid
hydrocarbon
parts
mixed
toluic 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
GB8568/50A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB681455A publication Critical patent/GB681455A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A process of preparing aromatic dicarboxylic acids by the liquid phase catalytic oxidation of aromatic compounds containing oxidizable substituents with oxygen or gaseous mixtures containing free oxygen comprises maintaining in the liquid phase undergoing oxidation from 5 to 50 parts of a substituted benzene in which a hydrocarbon substituent carrying at least one alpha-hydrogen atom is attached to each of at least two non-adjacent nuclear carbon atoms, from 15 to 95 parts of a substituted benzoic acid containing at least one meta- or para-substituent containing carbon and hydrogen, or carbon, hydrogen and oxygen, and carrying at least one alpha-hydrogen or alpha-oxygen atom, and from 0 to 80 parts of an inert solvent. By "parts" is meant parts by weight based on 100 parts by weight of material in the liquid phase, excluding the weight of catalyst. Substituents in the substituted benzoic acids may be primary or secondary hydrocarbon radicals, or -CHO, -COO (hydrocarbon, -CH2OH, -CH(O hydrocarbon)2, -CO (hydrocarbon), -CH2OCO (hydrocarbon) or -CH2O (hydrocarbon) groups. Halogen substituted benzoic acids, e.g. 3-methyl-5-chlorobenzoic acid, 4-allyl-5-bromo-benzoic acid and 2-chloro-4-isopropyl-benzoic acid are also mentioned. As substituted benzenes, meta-and para-dialkylbenzenes are particularly preferred. Mentioned are m- and p-xylene, m-and p-cymene, mesitylenes, 3 : 5-diethyl-tertiary-butylbenzene, p-eicosylbutylbenzene, p-isopentylcyclohexylbenzene, m- and p-diallyl benzene, p-pentyl-styrene, m-propargyltoluene and 2 : 4-dipropyl-ter. amylbenzene. Suitable solvents are o-dichlorbenzene, chlorobenzene, ter-butyl benzene, diphenyl, 1 : 2 : 3-trichloropropane and benzoic acid. Nitrobenzene, o-nitrotoluenes a -chloroinaphthalene, chloracetic acid, acetic acid and methyl benzoate were found to be not satisfactory. As catalysts are mentioned cobalt, barium and manganese as finely divided metals or oxides, or as e.g. chlorides, nitrates, acetates, salicylates, toluates, benzoates and alkylbenzoates. Reaction temperatures between 90 DEG and 300 DEG C. are mentioned. The process may be applied to mixtures containing also oxidizable aromatic compounds with side chains on adjacent carbon atoms or a single oxidizable side chain. Examples describe the oxidation of mixtures (within the above proportions) of (1), (3) and (5) p-xylene and p-toluic acid to terephthalic acid, (2) m-xylene and m-toluic acid to isophthalic acid, (4) mixed xylenes and p-toluic acid (or mixed m- and p-toluic acid to give mixed isophthalic and terephthalic acids, (6) mixed xylenes and mixed toluic acid to give mixed iso- and terephthalic acids and o-toluic acid, (7) a mixture of p-toluic acid and m-xylene to give mixed iso- and terephthalic acids, catalysts and solvents being selected from those specified above. Specification 623,836 is referred to.
GB8568/50A 1949-04-05 1950-04-05 Process for the production of aromatic dicarboxylic acids Expired GB681455A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US681455XA 1949-04-05 1949-04-05

Publications (1)

Publication Number Publication Date
GB681455A true GB681455A (en) 1952-10-22

Family

ID=22080690

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8568/50A Expired GB681455A (en) 1949-04-05 1950-04-05 Process for the production of aromatic dicarboxylic acids

Country Status (1)

Country Link
GB (1) GB681455A (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2746990A (en) * 1953-02-02 1956-05-22 Shell Dev Preparation of terephthalic acid
DE1004159B (en) * 1953-03-19 1957-03-14 Chempatents Inc Process for the preparation of terephthalic acid
DE1015421B (en) * 1953-04-15 1957-09-12 Chempatents Inc Process for the production of isophthalic acid
US2833820A (en) * 1957-06-14 1958-05-06 Mid Century Corp Process for the preparation of isophthalic and terephthalic acids
US2833818A (en) * 1956-07-30 1958-05-06 Mid Century Corp Process for the preparation of terephthalic acid
US2833817A (en) * 1956-06-27 1958-05-06 Mid Century Corp Process for the preparation of terephthalic acid
US2833819A (en) * 1957-06-14 1958-05-06 Mid Century Corp Process for the preparation of isophthalic and terephthalic acids
US2858334A (en) * 1954-11-26 1958-10-28 Mid Century Corp Preparation of phthalic acids
DE1081445B (en) * 1954-05-03 1960-05-12 Mid Century Corp Process for the production of aromatic di- or polycarboxylic acids
DE1097972B (en) * 1954-03-16 1961-01-26 Mid Century Corp Process for the preparation of benzene dicarboxylic acids
DE975405C (en) * 1954-10-07 1961-11-23 Huels Chemische Werke Ag Process for the preparation of terephthalic acid
DE1125416B (en) * 1955-07-22 1962-03-15 Olin Mathieson Process for the production of benzene carboxylic acids
DE976342C (en) * 1954-02-26 1963-07-11 Bergwerksverband Gmbh Process for the preparation of terephthalic acid
US3155717A (en) * 1956-06-27 1964-11-03 Mid Century Corp Process for the preparation of trimesic acid
DE1194393B (en) * 1961-07-24 1965-06-10 Socaty Soc Fr Process for the preparation of benzene dicarboxylic acids or their mixtures
US3256324A (en) * 1960-04-04 1966-06-14 Socony Mobil Oil Co Inc Oxidation of methylaromatic hydrocarbons in the presence of a promoter
DE1266296B (en) * 1953-03-19 1968-04-18 Mid Century Corp Process for the preparation of terephthalic acid

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2746990A (en) * 1953-02-02 1956-05-22 Shell Dev Preparation of terephthalic acid
DE1004159B (en) * 1953-03-19 1957-03-14 Chempatents Inc Process for the preparation of terephthalic acid
DE1266296B (en) * 1953-03-19 1968-04-18 Mid Century Corp Process for the preparation of terephthalic acid
DE1015421B (en) * 1953-04-15 1957-09-12 Chempatents Inc Process for the production of isophthalic acid
DE976342C (en) * 1954-02-26 1963-07-11 Bergwerksverband Gmbh Process for the preparation of terephthalic acid
DE1097972B (en) * 1954-03-16 1961-01-26 Mid Century Corp Process for the preparation of benzene dicarboxylic acids
DE1081445B (en) * 1954-05-03 1960-05-12 Mid Century Corp Process for the production of aromatic di- or polycarboxylic acids
DE975405C (en) * 1954-10-07 1961-11-23 Huels Chemische Werke Ag Process for the preparation of terephthalic acid
US2858334A (en) * 1954-11-26 1958-10-28 Mid Century Corp Preparation of phthalic acids
DE1125416B (en) * 1955-07-22 1962-03-15 Olin Mathieson Process for the production of benzene carboxylic acids
US2833817A (en) * 1956-06-27 1958-05-06 Mid Century Corp Process for the preparation of terephthalic acid
US3155717A (en) * 1956-06-27 1964-11-03 Mid Century Corp Process for the preparation of trimesic acid
US2833818A (en) * 1956-07-30 1958-05-06 Mid Century Corp Process for the preparation of terephthalic acid
US2833819A (en) * 1957-06-14 1958-05-06 Mid Century Corp Process for the preparation of isophthalic and terephthalic acids
US2833820A (en) * 1957-06-14 1958-05-06 Mid Century Corp Process for the preparation of isophthalic and terephthalic acids
US3256324A (en) * 1960-04-04 1966-06-14 Socony Mobil Oil Co Inc Oxidation of methylaromatic hydrocarbons in the presence of a promoter
DE1194393B (en) * 1961-07-24 1965-06-10 Socaty Soc Fr Process for the preparation of benzene dicarboxylic acids or their mixtures

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