JPH0420420B2 - - Google Patents
Info
- Publication number
- JPH0420420B2 JPH0420420B2 JP3002684A JP3002684A JPH0420420B2 JP H0420420 B2 JPH0420420 B2 JP H0420420B2 JP 3002684 A JP3002684 A JP 3002684A JP 3002684 A JP3002684 A JP 3002684A JP H0420420 B2 JPH0420420 B2 JP H0420420B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- carbonylation
- catalyst
- biphenyl
- alkyl
- 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
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 claims description 5
- LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 19
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 238000005810 carbonylation reaction Methods 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 230000006315 carbonylation Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- SRQOBNUBCLPPPH-UHFFFAOYSA-N 1-ethyl-4-phenylbenzene Chemical group C1=CC(CC)=CC=C1C1=CC=CC=C1 SRQOBNUBCLPPPH-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KWSHGRJUSUJPQD-UHFFFAOYSA-N 1-phenyl-4-propan-2-ylbenzene Chemical group C1=CC(C(C)C)=CC=C1C1=CC=CC=C1 KWSHGRJUSUJPQD-UHFFFAOYSA-N 0.000 description 2
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical group C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- -1 alkyl biphenyl Chemical compound 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DLMYHUARHITGIJ-UHFFFAOYSA-N 1-ethyl-2-phenylbenzene Chemical group CCC1=CC=CC=C1C1=CC=CC=C1 DLMYHUARHITGIJ-UHFFFAOYSA-N 0.000 description 1
- JRMFMZATWIFRMF-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1.C1=CC(C=O)=CC=C1C1=CC=CC=C1 JRMFMZATWIFRMF-UHFFFAOYSA-N 0.000 description 1
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 1
- XZIPJISANVLUBR-UHFFFAOYSA-N 5-ethyl-2-(4-ethylphenyl)benzaldehyde Chemical compound C(C)C=1C=C(C(=CC=1)C1=CC=C(C=C1)CC)C=O XZIPJISANVLUBR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001335 demethylating effect Effects 0.000 description 1
- PLXSXOUOWRGVOZ-UHFFFAOYSA-L dibromocobalt;hexahydrate Chemical compound O.O.O.O.O.O.Br[Co]Br PLXSXOUOWRGVOZ-UHFFFAOYSA-L 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940082328 manganese acetate tetrahydrate Drugs 0.000 description 1
- CESXSDZNZGSWSP-UHFFFAOYSA-L manganese(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].CC([O-])=O.CC([O-])=O CESXSDZNZGSWSP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 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
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
-
- 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3002684A JPS60174745A (ja) | 1984-02-20 | 1984-02-20 | ４，４’−ビフェニルジカルボン酸の製造法 |
| GB08502260A GB2155921B (en) | 1984-02-20 | 1985-01-30 | Process for producing 4-alkyl-4'-formylbiphenyl |
| DE19853504218 DE3504218C2 (de) | 1984-02-20 | 1985-02-07 | Verfahren zur Herstellung von 4-Alkyl-4'-formylbiphenyl und dessen Verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3002684A JPS60174745A (ja) | 1984-02-20 | 1984-02-20 | ４，４’−ビフェニルジカルボン酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60174745A JPS60174745A (ja) | 1985-09-09 |
| JPH0420420B2 true JPH0420420B2 (de) | 1992-04-02 |
Family
ID=12292314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3002684A Granted JPS60174745A (ja) | 1984-02-20 | 1984-02-20 | ４，４’−ビフェニルジカルボン酸の製造法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS60174745A (de) |
| DE (1) | DE3504218C2 (de) |
| GB (1) | GB2155921B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63122645A (ja) * | 1986-11-11 | 1988-05-26 | Kureha Chem Ind Co Ltd | ビフエニル−４，４’−ジカルボン酸の製造方法 |
| US5068407A (en) * | 1990-01-31 | 1991-11-26 | Monsanto Company | Oxidation of tertiary-alkyl substituted aromatics |
| JP2891277B2 (ja) * | 1993-07-29 | 1999-05-17 | 三菱瓦斯化学株式会社 | ４−ホルミル−４’−メチルビフェニルの製造法 |
| CN113372208A (zh) * | 2021-05-20 | 2021-09-10 | 山东盛华电子新材料有限公司 | 一种反-4-（反-4-烷环己基）环己烷甲醛的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB633176A (en) * | 1946-08-24 | 1949-12-12 | Du Pont | Improvements in and relating to the production of aromatic aldehydes |
-
1984
- 1984-02-20 JP JP3002684A patent/JPS60174745A/ja active Granted
-
1985
- 1985-01-30 GB GB08502260A patent/GB2155921B/en not_active Expired
- 1985-02-07 DE DE19853504218 patent/DE3504218C2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2155921A (en) | 1985-10-02 |
| GB2155921B (en) | 1987-09-03 |
| GB8502260D0 (en) | 1985-02-27 |
| DE3504218A1 (de) | 1985-08-22 |
| JPS60174745A (ja) | 1985-09-09 |
| DE3504218C2 (de) | 1994-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2723994A (en) | Oxidation of xylene and toluic acid mixtures to phthalic acids | |
| CN105873890A (zh) | 用于制备纯化的羧酸的氧化方法 | |
| EP0046397B1 (de) | Verfahren zur Herstellung von Trimellit- oder Pyromellitsäure | |
| JPH0420420B2 (de) | ||
| JPH0531536B2 (de) | ||
| JP3715492B2 (ja) | トルエンの触媒液相空気酸化によるベンズアルデヒドの改良された製造方法 | |
| KR100965633B1 (ko) | 물에서 ｐ-크실렌의 액상 산화에 의한 ｐ-톨루엔산의제조방법 | |
| CN103265416A (zh) | 甲苯高选择性制备苯甲醛的方法 | |
| JP4788022B2 (ja) | 芳香族ポリカルボン酸の製造法 | |
| EP1088810B1 (de) | Verfahren zur Herstellung von Benzaldehyd durch katalytische Luftoxidation von Toluol in der Flüssigphase | |
| CA1299189C (en) | (phenylethenyl)phenylpropionic acid and its ester, and method for producing (benzoylphenyl)propionic acid or its ester | |
| CN112851496A (zh) | 一种对甲基苯甲酸的制备方法 | |
| JP3027162B2 (ja) | ビフェニルカルボン酸の製造方法 | |
| CA2551446A1 (en) | Carboxylation of aromatic hydrocarbons to produce aromatic carboxylic acids | |
| US4088823A (en) | Promoted liquid phase oxidation of alkyl aromatic compounds | |
| CN102219678B (zh) | Co制草酸酯的开车方法 | |
| JP3756537B2 (ja) | ジメチルデカンジアールおよびその製造方法 | |
| US3703547A (en) | Method of preparing phthalic acids | |
| JP3389363B2 (ja) | 新規な触媒及び触媒を用いてカルボン酸を製造する方法 | |
| CA1047526A (en) | Process for making 4-acetoxybutyraldehyde and 4-acetoxybutanol | |
| TWI264432B (en) | Process for the production of terephthalic acids | |
| JP3264733B2 (ja) | ４−ビフェニルカルボン酸の製造方法 | |
| JPH06329567A (ja) | １，６−ヘキサンジオールの製造方法 | |
| JP2580699B2 (ja) | ２，６‐ナフタリンジカルボン酸の製造法 | |
| JPS6412257B2 (de) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |