GB681455A - Process for the production of aromatic dicarboxylic acids - Google Patents
Process for the production of aromatic dicarboxylic acidsInfo
- 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
Links
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (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.
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)
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 |
US2833817A (en) * | 1956-06-27 | 1958-05-06 | Mid Century Corp | Process for the preparation of terephthalic acid |
US2833820A (en) * | 1957-06-14 | 1958-05-06 | Mid Century Corp | Process for the preparation of isophthalic and terephthalic acids |
US2833819A (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 |
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 |
-
1950
- 1950-04-05 GB GB8568/50A patent/GB681455A/en not_active Expired
Cited By (17)
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 |
US3155717A (en) * | 1956-06-27 | 1964-11-03 | Mid Century Corp | Process for the preparation of trimesic acid |
US2833817A (en) * | 1956-06-27 | 1958-05-06 | Mid Century Corp | Process for the preparation of terephthalic 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 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB681455A (en) | Process for the production of aromatic dicarboxylic acids | |
US3255243A (en) | Process for the catalytic oxidation of aromatic substances to produce mono-and dicarboxylic acids | |
GB792199A (en) | Improvements in or relating to the preparation of aromatic dicarboxylic acids and partial alkyl esters thereof | |
ES299386A1 (en) | Procedure for the continuous preparation of aromatic acids (Machine-translation by Google Translate, not legally binding) | |
US2853514A (en) | Process for the preparation of aromatic carboxylic acids | |
US2552278A (en) | Liquid phase oxidation | |
KR101176390B1 (en) | Anthracene and other polycyclic aromatics as activators in the oxidation of aromatic hydrocarbons | |
US3139452A (en) | Oxidation of p-xylene to terephthalic acid | |
GB680571A (en) | Improvements in or relating to liquid phase oxidation | |
US3406196A (en) | Oxidation of polyalkyl aromatics to polycarboxylic acids | |
US2552268A (en) | Liquid phase oxidation | |
EP0041784A1 (en) | Oxidation of substituted aromatic compounds to aromatic carboxylic acids | |
GB1063451A (en) | Aromatic acids | |
US3584038A (en) | Oxidative treatment of mononuclear aromatic compounds | |
US2992271A (en) | Catalytic oxidation of aralkyl compounds | |
ES2287753T3 (en) | OXIDATION OF AROMATIC HYDROCARBONS USING PROMOTERS OF BROMATED ANTRACENS. | |
US2802859A (en) | Oxidation of alkylated benzenes in the presence of aliphatic hydrocarbons | |
GB901271A (en) | Ester preparation | |
GB807091A (en) | Process for the production of aromatic polycarboxylic acids | |
US3507914A (en) | Process for the preparation of aromatic carboxylic acids | |
GB833440A (en) | Preparation of aromatic carboxylic acids | |
US3507912A (en) | Process for the preparation of benzene carboxylic acids | |
GB1088183A (en) | Benzene polycarboxylic acids | |
US3452087A (en) | Process for the autoxidation of substituted benzenes | |
US3694500A (en) | Catalytic oxidation of polymethylstilbene compounds |