GB966986A - Oxidation of methylaromatics - Google Patents
Oxidation of methylaromaticsInfo
- Publication number
- GB966986A GB966986A GB12026/61A GB1202661A GB966986A GB 966986 A GB966986 A GB 966986A GB 12026/61 A GB12026/61 A GB 12026/61A GB 1202661 A GB1202661 A GB 1202661A GB 966986 A GB966986 A GB 966986A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxidation
- cumene
- april
- oxygen
- methylaromatic
- 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
- 230000003647 oxidation Effects 0.000 title abstract 3
- 238000007254 oxidation reaction Methods 0.000 title abstract 3
- -1 Aromatic carboxylic acids Chemical class 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 abstract 2
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 abstract 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 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
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 abstract 1
- KMHSUNDEGHRBNV-UHFFFAOYSA-N 2,4-dichloropyrimidine-5-carbonitrile Chemical compound ClC1=NC=C(C#N)C(Cl)=N1 KMHSUNDEGHRBNV-UHFFFAOYSA-N 0.000 abstract 1
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 abstract 1
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical class C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 abstract 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 abstract 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 abstract 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 150000003738 xylenes Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
- B65G47/00—Article or material-handling devices associated with conveyors; Methods employing such devices
- B65G47/34—Devices for discharging articles or materials from conveyor
- B65G47/46—Devices for discharging articles or materials from conveyor and distributing, e.g. automatically, to desired points
- B65G47/48—Devices for discharging articles or materials from conveyor and distributing, e.g. automatically, to desired points according to bodily destination marks on either articles or load-carriers
-
- 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)
- Mechanical Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
966,986. Aromatic carboxylic acids. SOCONY MOBIL OIL CO. Inc. April 4, 1961 [April 4, 1960], No. 12026/61. Heading C2C. Aromatic carboxylic acids are produced by contacting with an oxygen-containing gas a mixture of a methyl aromatic compound (otherwise not alkyl substituted) and a promoter comprising the structure (R is C 1-4 -alkyl) in a 0À1-10:1 weight ratio at a temperature from 50C. to the b.p. of the methylaromatic compound, a flow rate of said gas per 100gm. total alkylaromatic compounds of 0À1-4 cu. ft./hr. oxygen and for 0À5-10 hrs. The preferred promoter is cumene (although diisopropyl benzene and p-cymene are also mentioned) and an oxidation catalyst such as cobalt naphthenate or iron phthalocyanine may also be used. Specified methylaromatic compounds are toluene, the xylenes, hemimellitene, pseudocumene, mesitylene, 1- and 2-methylnaphthalenes, dimethylnaphthalene, the toluic and xylic acids, methylpyridine, p-chlorotoluene, tolunitrile. In examples acetophenone is obtained as a by-product, presumably by oxidation of cumene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1950060A | 1960-04-04 | 1960-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB966986A true GB966986A (en) | 1964-08-19 |
Family
ID=30769044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12026/61A Expired GB966986A (en) | 1960-04-04 | 1961-04-04 | Oxidation of methylaromatics |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3256324A (en) |
| BE (1) | BE602086A (en) |
| FR (1) | FR1299531A (en) |
| GB (1) | GB966986A (en) |
| IT (1) | IT649554A (en) |
| NL (1) | NL283165A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06157403A (en) * | 1992-11-30 | 1994-06-03 | Mitsubishi Petrochem Co Ltd | Method for producing 2,6-naphthalenedicarboxylic acid |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2245528A (en) * | 1938-10-18 | 1941-06-10 | Du Pont | Catalytic oxidation of alkyl substituted aromatic compounds |
| GB681455A (en) * | 1949-04-05 | 1952-10-22 | Bataafsche Petroleum | Process for the production of aromatic dicarboxylic acids |
| BE535707A (en) * | 1954-02-17 | |||
| US2833816A (en) * | 1954-05-03 | 1958-05-06 | Mid Century Corp | Preparation of aromatic polycarboxylic acids |
| GB787054A (en) * | 1954-12-24 | 1957-11-27 | Harold Newby | The oxidation of para-dialkylbenzenes to terephthalic acid and other oxidation products |
| US3139452A (en) * | 1957-02-25 | 1964-06-30 | Gen Electric | Oxidation of p-xylene to terephthalic acid |
-
0
- IT IT649554D patent/IT649554A/it unknown
- NL NL283165D patent/NL283165A/xx unknown
- BE BE602086D patent/BE602086A/xx unknown
-
1961
- 1961-03-30 FR FR857289A patent/FR1299531A/en not_active Expired
- 1961-04-04 GB GB12026/61A patent/GB966986A/en not_active Expired
-
1963
- 1963-08-26 US US304614A patent/US3256324A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR1299531A (en) | 1962-07-27 |
| US3256324A (en) | 1966-06-14 |
| BE602086A (en) | |
| NL283165A (en) | |
| IT649554A (en) |
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