GB1313083A - Process for producing para-toliuc acid and monomethyl terephthalate - Google Patents
Process for producing para-toliuc acid and monomethyl terephthalateInfo
- Publication number
- GB1313083A GB1313083A GB4147671A GB4147671A GB1313083A GB 1313083 A GB1313083 A GB 1313083A GB 4147671 A GB4147671 A GB 4147671A GB 4147671 A GB4147671 A GB 4147671A GB 1313083 A GB1313083 A GB 1313083A
- Authority
- GB
- United Kingdom
- Prior art keywords
- para
- salts
- manganese
- cobalt
- component
- 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
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 abstract 6
- -1 aromatic carboxylic acids Chemical class 0.000 abstract 5
- 229910052748 manganese Inorganic materials 0.000 abstract 5
- 239000011572 manganese Substances 0.000 abstract 5
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 abstract 4
- 230000003647 oxidation Effects 0.000 abstract 4
- 238000007254 oxidation reaction Methods 0.000 abstract 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 229910017052 cobalt Inorganic materials 0.000 abstract 3
- 239000010941 cobalt Substances 0.000 abstract 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 2
- 229910001882 dioxygen Inorganic materials 0.000 abstract 2
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 abstract 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 229940093858 ethyl acetoacetate Drugs 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 150000002484 inorganic compounds Chemical class 0.000 abstract 1
- 229910010272 inorganic material Inorganic materials 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000000126 substance Substances 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
- C07C51/21—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
-
- 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
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
1313083 Producing para-toluic acid and monomethylterephthalate TEIJIN HERCULES CHEMICAL CO Ltd 6 Sept 1971 [8 Sept 1970] 41476/71 Heading C2C The invention comprises a process for producing para-toluic acid and monomethylterephthalate by liquid phase oxidation of a mixture containing para-xylene and methylparatoluate in a weight ratio of 2 : 1-1 : 4 with molecular oxygen or a gas containing molecular oxygen, the reaction being carried out at 140-240‹ C. in the presence of an oxidation catalyst comprising a manganese component (A), which is manganese or one of its compounds which is soluble in the reaction system, and a cobalt component B, which is cobalt or one of its salts which is soluble in the reaction system, the g. atomic ratio of manganese to cobalt being from 0À1: 99À9 to 99 : 1 and the total catalyst concentration (in terms of total content of Mn and Co present in components A and B) being from 50- 1500 p.p.m. by wt. based on the total amount of reaction mixture. Specified compounds of Co and Mn which can form a component of the catalyst are (i) salts of C 1 -C 20 aliphatic carboxylic acids, (ii) salts of aromatic carboxylic acids, e.g. benzoic or toluic, (iii) alicyclic carboxylic acid, e.g. naphthenic, (iv) complexes with, e.g. acetylacetone, methylacetoacetate, ethylacetoacetate, (v) inorganic compounds, e.g. carbonates, oxides, or hydroxides. After the oxidation process of the invention the monomethyl terephthalate and para-toluic acid produced can be esterified to dimethyl terephthalate, which can be used in formation of film and fibre-forming polyesters, and methyl para-toluate which can be recycled to the oxidation process together with fresh para-xylene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7874270A JPS4927574B1 (en) | 1970-09-08 | 1970-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1313083A true GB1313083A (en) | 1973-04-11 |
Family
ID=13670323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4147671A Expired GB1313083A (en) | 1970-09-08 | 1971-09-06 | Process for producing para-toliuc acid and monomethyl terephthalate |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4927574B1 (en) |
| BE (1) | BE772355A (en) |
| CA (1) | CA963913A (en) |
| DE (2) | DE2166885C2 (en) |
| FR (1) | FR2107340A5 (en) |
| GB (1) | GB1313083A (en) |
| IT (1) | IT938783B (en) |
| NL (1) | NL153179C (en) |
| RO (1) | RO62280A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006103693A1 (en) * | 2005-03-31 | 2006-10-05 | Council Of Scientific & Industrial Research | A process for the preparation of p-toluic acid by liquid phase oxidation of p-xylene in water |
| US8193402B2 (en) | 2007-12-03 | 2012-06-05 | Gevo, Inc. | Renewable compositions |
| US8373012B2 (en) | 2010-05-07 | 2013-02-12 | Gevo, Inc. | Renewable jet fuel blendstock from isobutanol |
| US8378160B2 (en) | 2007-12-03 | 2013-02-19 | Gevo, Inc. | Renewable compositions |
| US8450543B2 (en) | 2010-01-08 | 2013-05-28 | Gevo, Inc. | Integrated methods of preparing renewable chemicals |
| US8742187B2 (en) | 2011-04-19 | 2014-06-03 | Gevo, Inc. | Variations on prins-like chemistry to produce 2,5-dimethylhexadiene from isobutanol |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4927574B1 (en) * | 1970-09-08 | 1974-07-18 | ||
| BE791138R (en) | 1971-12-18 | 1973-05-09 | Dynamit Nobel Ag | PROCESS FOR PREPARING THE DIMETHYL ESTER OF TEREPHTHALIC ACID |
| JPS522895B2 (en) * | 1972-08-14 | 1977-01-25 | ||
| JPS54119427A (en) * | 1978-03-07 | 1979-09-17 | Teijin Ltd | Preparation of benzenecarboxylic acid |
| NL8001550A (en) * | 1980-03-15 | 1981-10-16 | Stamicarbon | PROCESS FOR PREPARING BENZENE MONOCARBONIC ACIDS. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE949564C (en) * | 1951-04-13 | 1956-09-20 | Imhausen & Co G M B H | Process for the preparation of terephthalic acid monomethyl ester |
| NL246757A (en) * | 1958-12-23 | |||
| GB907926A (en) * | 1960-04-18 | 1962-10-10 | Distillers Co Yeast Ltd | Improvements in or relating to the production of trimellitic acid and trimellitic anhydride |
| GB1007570A (en) * | 1961-07-24 | 1965-10-13 | Socaty | Process for the catalytic oxidation of xylenes or industrial mixtures of xylenes |
| DE2010137C3 (en) * | 1970-03-04 | 1979-07-05 | Dynamit Nobel Ag, 5210 Troisdorf | Process for the preparation of dimethyl terephthalate |
| JPS4927574B1 (en) * | 1970-09-08 | 1974-07-18 | ||
| JPS522896B2 (en) * | 1973-01-18 | 1977-01-25 |
-
1970
- 1970-09-08 JP JP7874270A patent/JPS4927574B1/ja active Pending
-
1971
- 1971-09-06 GB GB4147671A patent/GB1313083A/en not_active Expired
- 1971-09-07 FR FR7132225A patent/FR2107340A5/fr not_active Expired
- 1971-09-07 CA CA122,256A patent/CA963913A/en not_active Expired
- 1971-09-08 IT IT2837071A patent/IT938783B/en active
- 1971-09-08 DE DE19712166885 patent/DE2166885C2/en not_active Expired
- 1971-09-08 DE DE19712144920 patent/DE2144920C3/en not_active Expired
- 1971-09-08 BE BE772355A patent/BE772355A/en unknown
- 1971-09-08 RO RO6816371A patent/RO62280A/en unknown
- 1971-09-08 NL NL7112366A patent/NL153179C/en not_active IP Right Cessation
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006103693A1 (en) * | 2005-03-31 | 2006-10-05 | Council Of Scientific & Industrial Research | A process for the preparation of p-toluic acid by liquid phase oxidation of p-xylene in water |
| KR100965633B1 (en) | 2005-03-31 | 2010-06-23 | 카운슬 오브 사이언티픽 앤드 인더스트리얼 리서치 | A process for the preparation of p-toluic acid by liquid phase oxidation of p-xylene in water |
| CN101146755B (en) * | 2005-03-31 | 2012-07-11 | 科学与工业研究委员会 | Process for the preparation of p-toluic acid by liquid phase oxidation of p-xylene in water |
| US8193402B2 (en) | 2007-12-03 | 2012-06-05 | Gevo, Inc. | Renewable compositions |
| US8378160B2 (en) | 2007-12-03 | 2013-02-19 | Gevo, Inc. | Renewable compositions |
| US8487149B2 (en) | 2007-12-03 | 2013-07-16 | Gevo, Inc. | Renewable compositions |
| US8546627B2 (en) | 2007-12-03 | 2013-10-01 | Gevo, Inc. | Renewable compositions |
| US8450543B2 (en) | 2010-01-08 | 2013-05-28 | Gevo, Inc. | Integrated methods of preparing renewable chemicals |
| US8373012B2 (en) | 2010-05-07 | 2013-02-12 | Gevo, Inc. | Renewable jet fuel blendstock from isobutanol |
| US8975461B2 (en) | 2010-05-07 | 2015-03-10 | Gevo, Inc. | Renewable jet fuel blendstock from isobutanol |
| US8742187B2 (en) | 2011-04-19 | 2014-06-03 | Gevo, Inc. | Variations on prins-like chemistry to produce 2,5-dimethylhexadiene from isobutanol |
Also Published As
| Publication number | Publication date |
|---|---|
| NL153179B (en) | 1977-05-16 |
| CA963913A (en) | 1975-03-04 |
| BE772355A (en) | 1972-01-17 |
| DE2144920A1 (en) | 1972-04-13 |
| NL7112366A (en) | 1972-03-10 |
| NL153179C (en) | 1979-11-15 |
| DE2166885C2 (en) | 1984-10-11 |
| RO62280A (en) | 1978-04-15 |
| JPS4927574B1 (en) | 1974-07-18 |
| DE2166885A1 (en) | 1976-11-18 |
| IT938783B (en) | 1973-02-10 |
| FR2107340A5 (en) | 1972-05-05 |
| DE2144920C3 (en) | 1982-12-02 |
| DE2144920B2 (en) | 1977-06-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 414F | Notice of opposition given (sect. 14/1949) | ||
| 414A | Case decided by the comptroller ** specification amended (sect. 14/1949) | ||
| SPA | Amended specification published | ||
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |