RU2008108096A - Способ получения 4,4'-дифторбензофенона - Google Patents
Способ получения 4,4'-дифторбензофенона Download PDFInfo
- Publication number
- RU2008108096A RU2008108096A RU2008108096/04A RU2008108096A RU2008108096A RU 2008108096 A RU2008108096 A RU 2008108096A RU 2008108096/04 A RU2008108096/04 A RU 2008108096/04A RU 2008108096 A RU2008108096 A RU 2008108096A RU 2008108096 A RU2008108096 A RU 2008108096A
- Authority
- RU
- Russia
- Prior art keywords
- stage
- nitric acid
- difluorobenzophenone
- fluorobenzene
- oxidizing agent
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract 6
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract 6
- 238000006243 chemical reaction Methods 0.000 claims abstract 4
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000007800 oxidant agent Substances 0.000 claims abstract 4
- JIFAWAXKXDTUHW-UHFFFAOYSA-N 2-fluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1F JIFAWAXKXDTUHW-UHFFFAOYSA-N 0.000 claims abstract 2
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 claims abstract 2
- LVTDRHCAWKTYCQ-UHFFFAOYSA-N [difluoro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(F)(F)C1=CC=CC=C1 LVTDRHCAWKTYCQ-UHFFFAOYSA-N 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims abstract 2
- 238000006555 catalytic reaction Methods 0.000 claims abstract 2
- 239000007789 gas Substances 0.000 claims abstract 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims abstract 2
- 150000003460 sulfonic acids Chemical class 0.000 claims abstract 2
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
- C07C49/786—Benzophenone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2637—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions between a compound containing only oxygen and possibly halogen as hetero-atoms and a halogenated hydrocarbon
-
- 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
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1. Способ получения 4,4'-дифторбензофенона, отличающийся тем, что на первой стадии фторбензол приводят в реакцию с формальдегидом в условиях катализа органическими сульфоновыми кислотами с образованием дифтордифенилметана, образованный при этом продукт выделяют и на второй стадии окисляют азотной кислотой до 4,4'-дифторбензофенона. ! 2. Способ по п.1, отличающийся тем, что для первой стадии реакции фторбензол применяют как растворитель, а фторбензолсульфоновую кислоту как катализатор. ! 3. Способ по п.1, отличающийся тем, что температура реакции на первой стадии составляет от -15°С до 70°С. ! 4. Способ по п.1, отличающийся тем, что на второй стадии проводят окисление азотной кислотой, и образующиеся нитрозные газы окислителем снова преобразуют в азотную кислоту. ! 5. Способ по п.4, отличающийся тем, что в качестве окислителя применяют кислород.
Claims (5)
1. Способ получения 4,4'-дифторбензофенона, отличающийся тем, что на первой стадии фторбензол приводят в реакцию с формальдегидом в условиях катализа органическими сульфоновыми кислотами с образованием дифтордифенилметана, образованный при этом продукт выделяют и на второй стадии окисляют азотной кислотой до 4,4'-дифторбензофенона.
2. Способ по п.1, отличающийся тем, что для первой стадии реакции фторбензол применяют как растворитель, а фторбензолсульфоновую кислоту как катализатор.
3. Способ по п.1, отличающийся тем, что температура реакции на первой стадии составляет от -15°С до 70°С.
4. Способ по п.1, отличающийся тем, что на второй стадии проводят окисление азотной кислотой, и образующиеся нитрозные газы окислителем снова преобразуют в азотную кислоту.
5. Способ по п.4, отличающийся тем, что в качестве окислителя применяют кислород.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005037337.2 | 2005-08-04 | ||
| DE102005037337A DE102005037337A1 (de) | 2005-08-04 | 2005-08-04 | Neues Verfahren zur Herstellung von 4,4'-Difluorbenzophenon |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008108096A true RU2008108096A (ru) | 2009-09-10 |
| RU2394016C2 RU2394016C2 (ru) | 2010-07-10 |
Family
ID=37149885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008108096/04A RU2394016C2 (ru) | 2005-08-04 | 2006-07-27 | Способ получения 4,4'-дифторбензофенона |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7687668B2 (ru) |
| EP (1) | EP1910259A1 (ru) |
| JP (1) | JP2009503000A (ru) |
| KR (1) | KR20080038147A (ru) |
| CN (1) | CN101238089A (ru) |
| BR (1) | BRPI0614510A2 (ru) |
| DE (1) | DE102005037337A1 (ru) |
| RU (1) | RU2394016C2 (ru) |
| TW (1) | TW200720241A (ru) |
| WO (1) | WO2007014692A1 (ru) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2342259B1 (en) | 2008-10-24 | 2013-08-07 | Solvay Specialty Polymers USA, LLC. | Improved process for preparing a poly(aryl ether ketone) using a high purity 4,4'-difluorobenzophenone |
| CN101891603B (zh) * | 2010-06-29 | 2012-12-19 | 陕西师范大学 | 2,6-二氟苯偶酰及其制备方法和应用 |
| EP2588513B1 (en) | 2010-07-02 | 2017-10-04 | Solvay Specialty Polymers USA, LLC. | Method of making poly(aryl ether ketones) from 4,4' difluorobenzophenone comprising oxidizing species and/or nitro compounds |
| US10745522B2 (en) * | 2014-10-24 | 2020-08-18 | Solvay Specialty Polymers Usa, Llc | Method for the manufacture of poly(aryl ethers) using at least one organic base |
| EP3492475A1 (en) | 2017-12-01 | 2019-06-05 | Rhodia Operations | New cycloadduct precursors of dihalobenzophenones and preparations thereof |
| EP3492449B1 (en) * | 2017-12-01 | 2020-09-23 | Rhodia Operations | Process for the preparation of dihalobenzophenones, new chemicals useful for its implementation and methods for preparing said chemicals |
| EP3736260A1 (en) | 2019-05-10 | 2020-11-11 | Rhodia Operations | Process for the preparation of dihalobenzophenones, new chemicals useful for its implementation and methods for preparing said chemicals |
| EP3736259B1 (en) * | 2019-05-10 | 2022-08-03 | Rhodia Operations | New cycloadduct precursors of dihalobenzophenones and preparations thereof |
| EP3838883B1 (en) | 2019-12-16 | 2023-07-12 | Evonik Fibres GmbH | Method for oxidizing a 1,1-bis-(3,4-dimethylphenyl)-alkane to 3,3',4,4'-benzophenone tetracarboxylic acid |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004710B1 (en) * | 1978-03-31 | 1981-11-04 | Imperial Chemical Industries Plc | Preparation of 4,4'-difluorobenzophenone |
| DE3411326A1 (de) * | 1984-03-28 | 1985-10-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von mit fluor enthaltenden gruppen substituierten, symmetrischen benzophenonen, deren verwendung und neue, mit fluor enthaltenden gruppen substituierte, symmetrische benzophenone |
-
2005
- 2005-08-04 DE DE102005037337A patent/DE102005037337A1/de not_active Withdrawn
-
2006
- 2006-07-27 US US11/989,790 patent/US7687668B2/en not_active Expired - Fee Related
- 2006-07-27 EP EP06762852A patent/EP1910259A1/de not_active Withdrawn
- 2006-07-27 JP JP2008524406A patent/JP2009503000A/ja not_active Withdrawn
- 2006-07-27 RU RU2008108096/04A patent/RU2394016C2/ru not_active IP Right Cessation
- 2006-07-27 KR KR1020087002621A patent/KR20080038147A/ko not_active Application Discontinuation
- 2006-07-27 CN CNA2006800284967A patent/CN101238089A/zh active Pending
- 2006-07-27 BR BRPI0614510-8A patent/BRPI0614510A2/pt not_active IP Right Cessation
- 2006-07-27 WO PCT/EP2006/007426 patent/WO2007014692A1/de active Application Filing
- 2006-08-01 TW TW095128181A patent/TW200720241A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7687668B2 (en) | 2010-03-30 |
| TW200720241A (en) | 2007-06-01 |
| WO2007014692A1 (de) | 2007-02-08 |
| CN101238089A (zh) | 2008-08-06 |
| JP2009503000A (ja) | 2009-01-29 |
| US20090177014A1 (en) | 2009-07-09 |
| BRPI0614510A2 (pt) | 2011-03-29 |
| DE102005037337A1 (de) | 2007-02-15 |
| KR20080038147A (ko) | 2008-05-02 |
| RU2394016C2 (ru) | 2010-07-10 |
| EP1910259A1 (de) | 2008-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20120728 |