GB655074A - An improved process for the preparation of terephthalic acid - Google Patents
An improved process for the preparation of terephthalic acidInfo
- Publication number
- GB655074A GB655074A GB1892/48A GB189248A GB655074A GB 655074 A GB655074 A GB 655074A GB 1892/48 A GB1892/48 A GB 1892/48A GB 189248 A GB189248 A GB 189248A GB 655074 A GB655074 A GB 655074A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- benzene
- terephthalic acid
- xylene
- oxidized
- 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title abstract 10
- 238000000034 method Methods 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 15
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 abstract 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 3
- 229910017604 nitric acid Inorganic materials 0.000 abstract 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 abstract 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 2
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 abstract 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001224 Uranium Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052753 mercury Inorganic materials 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
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
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
- C07C51/275—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids of hydrocarbyl 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)
Abstract
<PICT:0655074/IV (b)/1> Terephthalic acid is prepared by reacting a p-dialkyl benzene or a p-dialkyl benzene in which the alkyl groups may be partially oxidized with nitric acid, having an initial strength between 5 and 60 per cent, at superatmospheric pressure at a temperature above 150 DEG C. The said benzene may be p-xylene, p-cymene, p - diisopropylbenzene, p - divinylbenzene or p-tolualdehyde. An alkyl ester of p-toluic acid may be added to the said benzene. The crude reaction product may be separated from the residual acid liquor and any p-toluic acid therein is subjected to the above oxidation process. An oxygen containing gas may be introduced to assist the oxidizing reaction. Mercury or uranium salts may be used as a catalyst. Oxidized groups which may be present in the benzene include aldehyde, alcohol and carboxyl groups. In the examples, terephthalic acid is prepared in admixture with toluic acid. The terephthalic acid may be converted by known methods into its dimethyl or other alkyl ester and any esters of toluic acid recovered from the reaction product may then be oxidized as above. A suitable apparatus for carrying out the process comprises an autoclave 1 provided with stirrer 2 and heating or cooling jacket 4. Reactants are introduced at 9, nitric acid at 10, while condenser 8 returns condensible liquids to the autoclave and outlet 12 is used for gaseous materials. The Specification as open to inspection under Sect. 91 refers to the preparation of terephthalic acid by the reaction of dilute nitric acid in accordance with the above process with p-dialkyl benzenes and such compounds containing substituents in at least one side chain, e.g. g -nitro-p-xylene or g -hydroxy-p-xylene. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US277296XA | 1946-08-17 | 1946-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB655074A true GB655074A (en) | 1951-07-11 |
Family
ID=21839433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1892/48A Expired GB655074A (en) | 1946-08-17 | 1948-01-21 | An improved process for the preparation of terephthalic acid |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE480593A (en) |
| CH (1) | CH277296A (en) |
| FR (1) | FR961030A (en) |
| GB (1) | GB655074A (en) |
| NL (1) | NL67858C (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666786A (en) * | 1952-04-24 | 1954-01-19 | Us Rubber Co | Terephthalic acid synthesis |
| US2695311A (en) * | 1952-08-23 | 1954-11-23 | Monsanto Chemicals | Preparation of 2-and 4-nitrobenzoic acid |
| DE951566C (en) * | 1953-08-17 | 1956-10-31 | Henkel & Cie Gmbh | Process for the preparation of terephthalic acid |
| DE1004159B (en) * | 1953-03-19 | 1957-03-14 | Chempatents Inc | Process for the preparation of terephthalic acid |
| US2788366A (en) * | 1952-01-30 | 1957-04-09 | Glanzstoff Ag | Preparation of terephthalic acid |
| DE1060378B (en) * | 1952-08-23 | 1959-07-02 | Mid Century Corp | Process for the preparation of terephthalic acid |
| DE1081878B (en) * | 1955-09-22 | 1960-05-19 | Wilhelm Schemuth | Process for the production of terephthalic acid by the oxidation of p-ethyltoluene |
| US2975211A (en) * | 1955-03-21 | 1961-03-14 | Heyden Newport Chemical Corp | Production of trichlorobenzoic acid |
| DE1136688B (en) * | 1957-02-09 | 1962-09-20 | Robert Sancier Aries | Process for the preparation of benzene dicarboxylic acids |
| DE1146047B (en) * | 1960-09-13 | 1963-03-28 | Montedison Spa | Process for the production of pure terephthalic acid by the oxidation of p-xylene with dilute nitric acid |
| US3150171A (en) * | 1958-06-16 | 1964-09-22 | Bergwerksverband G M B H Fa | Production of aromatic carboxylic acids from aralkyl halides |
| US3278592A (en) * | 1961-03-15 | 1966-10-11 | Basf Ag | Continuous oxidation of aromatic compounds having oxidizable side chains |
| DE1266296B (en) * | 1953-03-19 | 1968-04-18 | Mid Century Corp | Process for the preparation of terephthalic acid |
-
0
- NL NL67858D patent/NL67858C/xx active
- FR FR961030D patent/FR961030A/fr not_active Expired
- BE BE480593D patent/BE480593A/xx unknown
-
1948
- 1948-01-21 GB GB1892/48A patent/GB655074A/en not_active Expired
- 1948-01-29 CH CH277296D patent/CH277296A/en unknown
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2788366A (en) * | 1952-01-30 | 1957-04-09 | Glanzstoff Ag | Preparation of terephthalic acid |
| US2666786A (en) * | 1952-04-24 | 1954-01-19 | Us Rubber Co | Terephthalic acid synthesis |
| US2695311A (en) * | 1952-08-23 | 1954-11-23 | Monsanto Chemicals | Preparation of 2-and 4-nitrobenzoic acid |
| DE1060378B (en) * | 1952-08-23 | 1959-07-02 | Mid Century Corp | 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 |
| DE1004159B (en) * | 1953-03-19 | 1957-03-14 | Chempatents Inc | Process for the preparation of terephthalic acid |
| DE951566C (en) * | 1953-08-17 | 1956-10-31 | Henkel & Cie Gmbh | Process for the preparation of terephthalic acid |
| US2975211A (en) * | 1955-03-21 | 1961-03-14 | Heyden Newport Chemical Corp | Production of trichlorobenzoic acid |
| DE1081878B (en) * | 1955-09-22 | 1960-05-19 | Wilhelm Schemuth | Process for the production of terephthalic acid by the oxidation of p-ethyltoluene |
| DE1136688B (en) * | 1957-02-09 | 1962-09-20 | Robert Sancier Aries | Process for the preparation of benzene dicarboxylic acids |
| US3150171A (en) * | 1958-06-16 | 1964-09-22 | Bergwerksverband G M B H Fa | Production of aromatic carboxylic acids from aralkyl halides |
| DE1146047B (en) * | 1960-09-13 | 1963-03-28 | Montedison Spa | Process for the production of pure terephthalic acid by the oxidation of p-xylene with dilute nitric acid |
| US3235587A (en) * | 1960-09-13 | 1966-02-15 | Montedison Spa | Process for the preparation of terephthalic acid having a high degree of purity |
| US3278592A (en) * | 1961-03-15 | 1966-10-11 | Basf Ag | Continuous oxidation of aromatic compounds having oxidizable side chains |
Also Published As
| Publication number | Publication date |
|---|---|
| FR961030A (en) | 1950-04-28 |
| CH277296A (en) | 1951-08-31 |
| BE480593A (en) | |
| NL67858C (en) |
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