GB770478A - An improved process of producing polycyclic ketones - Google Patents
An improved process of producing polycyclic ketonesInfo
- Publication number
- GB770478A GB770478A GB34387/54A GB3438754A GB770478A GB 770478 A GB770478 A GB 770478A GB 34387/54 A GB34387/54 A GB 34387/54A GB 3438754 A GB3438754 A GB 3438754A GB 770478 A GB770478 A GB 770478A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- oxidation
- acetic acid
- cobalt chloride
- cobalt
- 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
- -1 polycyclic ketones Chemical class 0.000 title abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 18
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 6
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 abstract 6
- 230000003647 oxidation Effects 0.000 abstract 6
- 238000007254 oxidation reaction Methods 0.000 abstract 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 abstract 4
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- JBXIOAKUBCTDES-UHFFFAOYSA-N 2h-acenaphthylen-1-one Chemical compound C1=CC(C(=O)C2)=C3C2=CC=CC3=C1 JBXIOAKUBCTDES-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 2
- 239000012965 benzophenone Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 235000019260 propionic acid Nutrition 0.000 abstract 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 2
- BDCIZVMGTWOOIY-UHFFFAOYSA-N 1,10-dihydroanthracene Chemical compound C1=CC=C2C=C3CC=CC=C3CC2=C1 BDCIZVMGTWOOIY-UHFFFAOYSA-N 0.000 abstract 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 abstract 1
- NDVAMUMVOJRAJV-UHFFFAOYSA-N 10h-phenanthren-9-one Chemical compound C1=CC=C2C(=O)CC3=CC=CC=C3C2=C1 NDVAMUMVOJRAJV-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052797 bismuth Inorganic materials 0.000 abstract 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000011133 lead Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 abstract 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- 125000005609 naphthenate group Chemical group 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- 239000011135 tin Substances 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
-
- 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
- C07C45/35—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 propene or isobutene
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1095348D FR1095348A (fr) | 1954-11-26 | 1953-10-23 | Procédé de fabrication de cétones bicycliques |
| BE533179D BE533179A (enrdf_load_stackoverflow) | 1954-11-26 | 1954-11-02 | |
| DEI9354A DE1044059B (de) | 1954-11-10 | 1954-11-10 | Verfahren zur Herstellung bicyclischer Ketone |
| US470797A US2859247A (en) | 1954-11-23 | 1954-11-23 | Process for the preparation of bicyclic ketones |
| NL192671D NL91100C (enrdf_load_stackoverflow) | 1954-11-26 | 1954-11-25 | |
| GB34387/54A GB770478A (en) | 1954-11-26 | 1954-11-26 | An improved process of producing polycyclic ketones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34387/54A GB770478A (en) | 1954-11-26 | 1954-11-26 | An improved process of producing polycyclic ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB770478A true GB770478A (en) | 1957-03-20 |
Family
ID=10365016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34387/54A Expired GB770478A (en) | 1954-11-10 | 1954-11-26 | An improved process of producing polycyclic ketones |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2859247A (enrdf_load_stackoverflow) |
| BE (1) | BE533179A (enrdf_load_stackoverflow) |
| DE (1) | DE1044059B (enrdf_load_stackoverflow) |
| FR (1) | FR1095348A (enrdf_load_stackoverflow) |
| GB (1) | GB770478A (enrdf_load_stackoverflow) |
| NL (1) | NL91100C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584557A (zh) * | 2011-12-31 | 2012-07-18 | 浙江工业大学 | 一种苊酮的制备方法 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2977310A (en) * | 1957-04-17 | 1961-03-28 | Sun Oil Co | Oxidation of petroleum fractions |
| US3038940A (en) * | 1958-04-25 | 1962-06-12 | Standard Oil Co | Process for preparation of aromatic ketones |
| DE1212508B (de) * | 1962-06-13 | 1966-03-17 | United States Steel Corp | Verfahren zur katalytischen Oxydation von teilweise hydrierten, polycyclischen, aromatischen und heterocyclischen Verbindungen |
| US3310586A (en) * | 1963-02-14 | 1967-03-21 | Gen Electric | Process of making 3, 4-dihydro-1(2h)-naphthalenones |
| US3424789A (en) * | 1964-03-05 | 1969-01-28 | Gulf Research Development Co | Process for oxidizing a 1,1-bis-(alkyl-phenyl)alkane |
| DE1267675B (de) * | 1966-07-28 | 1968-05-09 | Akad Wissenschaften Ddr | Verfahren zur Herstellung von p-Nitroacetophenon durch Oxydation von p-Nitroaethylbenzol mit Sauerstoff oder Luft |
| US3855252A (en) * | 1968-07-15 | 1974-12-17 | Ashland Oil Inc | Liquid phase oxidation of condensed-ring aromatic hydrocarbons |
| IT1054577B (it) * | 1976-01-30 | 1981-11-30 | Brichima Spa | Processo per la preparazione di aldeidi e chetoni aromatici |
| JPS5414950A (en) * | 1977-07-07 | 1979-02-03 | Agency Of Ind Science & Technol | Preparation of alpha-tetralone |
| US4405523A (en) * | 1982-03-24 | 1983-09-20 | Standard Oil Company (Indiana) | Process for preparation of benzophenone, anthraquinone and O-dibenzoylbenzene |
| US4572796A (en) * | 1984-05-24 | 1986-02-25 | International Flavors & Fragrances Inc. | 1,1,4,7-Tetramethyl-3-indanone, product produced thereby and organoleptic uses thereof |
| US5015778A (en) * | 1989-12-18 | 1991-05-14 | The Dow Chemical Company | Catalytic method to produce hydroxy substituted arylophenones |
| CN116323538A (zh) * | 2020-10-23 | 2023-06-23 | 三菱瓦斯化学株式会社 | 芴酮的制造方法 |
| KR20240087737A (ko) * | 2021-10-01 | 2024-06-19 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 플루오렌온의 제조 방법 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1813606A (en) * | 1926-12-23 | 1931-07-07 | Ig Farbenindustrie Ag | Process of obtaining oxygenated compounds from alkyl benzenes |
| US2245528A (en) * | 1938-10-18 | 1941-06-10 | Du Pont | Catalytic oxidation of alkyl substituted aromatic compounds |
| DE767389C (de) * | 1940-11-16 | 1952-07-31 | Bayer Ag | Verfahren zur Herstellung von Diketonen |
-
1953
- 1953-10-23 FR FR1095348D patent/FR1095348A/fr not_active Expired
-
1954
- 1954-11-02 BE BE533179D patent/BE533179A/xx unknown
- 1954-11-10 DE DEI9354A patent/DE1044059B/de active Pending
- 1954-11-23 US US470797A patent/US2859247A/en not_active Expired - Lifetime
- 1954-11-25 NL NL192671D patent/NL91100C/xx active
- 1954-11-26 GB GB34387/54A patent/GB770478A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584557A (zh) * | 2011-12-31 | 2012-07-18 | 浙江工业大学 | 一种苊酮的制备方法 |
| CN102584557B (zh) * | 2011-12-31 | 2014-03-26 | 浙江工业大学 | 一种苊酮的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE533179A (enrdf_load_stackoverflow) | 1954-11-30 |
| DE1044059B (de) | 1958-11-20 |
| FR1095348A (fr) | 1955-06-01 |
| NL91100C (enrdf_load_stackoverflow) | 1959-06-15 |
| US2859247A (en) | 1958-11-04 |
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