JP2012519172A5 - - Google Patents
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- Publication number
- JP2012519172A5 JP2012519172A5 JP2011552093A JP2011552093A JP2012519172A5 JP 2012519172 A5 JP2012519172 A5 JP 2012519172A5 JP 2011552093 A JP2011552093 A JP 2011552093A JP 2011552093 A JP2011552093 A JP 2011552093A JP 2012519172 A5 JP2012519172 A5 JP 2012519172A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- dihydroxybenzophenone
- reaction product
- mixture
- lewis acid
- 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.)
- Granted
Links
- LJQVLJXQHTULEP-UHFFFAOYSA-N (3-hydroxyphenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC(O)=C1 LJQVLJXQHTULEP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 8
- 150000007517 lewis acids Chemical class 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- DNUYOWCKBJFOGS-UHFFFAOYSA-N 2-[[10-(2,2-dicarboxyethyl)anthracen-9-yl]methyl]propanedioic acid Chemical compound C1=CC=C2C(CC(C(=O)O)C(O)=O)=C(C=CC=C3)C3=C(CC(C(O)=O)C(O)=O)C2=C1 DNUYOWCKBJFOGS-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000012258 stirred mixture Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 description 13
- DKCPZSOWADOUDB-UHFFFAOYSA-N [4-(3-acetyloxybenzoyl)phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C(=O)C1=CC=CC(OC(C)=O)=C1 DKCPZSOWADOUDB-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000011967 lanthanide triflate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- YHBDIEWMOMLKOO-UHFFFAOYSA-I pentachloroniobium Chemical compound Cl[Nb](Cl)(Cl)(Cl)Cl YHBDIEWMOMLKOO-UHFFFAOYSA-I 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/393,310 US7772441B1 (en) | 2009-02-26 | 2009-02-26 | Process for producing 3,4′ dihydroxybenzophenone |
| US12/393,310 | 2009-02-26 | ||
| PCT/US2010/025146 WO2010099144A1 (en) | 2009-02-26 | 2010-02-24 | Process for producing 3,4' dihydroxybenzophenone as an intermediate for producing 3,4' diacetoxybenzophenone |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012519172A JP2012519172A (ja) | 2012-08-23 |
| JP2012519172A5 true JP2012519172A5 (enExample) | 2013-04-18 |
| JP5480918B2 JP5480918B2 (ja) | 2014-04-23 |
Family
ID=42199000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011552093A Expired - Fee Related JP5480918B2 (ja) | 2009-02-26 | 2010-02-24 | ３，４’ジアセトキシベンゾフェノン製造用中間体としての３，４’ジヒドロキシベンゾフェノンの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7772441B1 (enExample) |
| EP (1) | EP2401249B1 (enExample) |
| JP (1) | JP5480918B2 (enExample) |
| KR (1) | KR20110122749A (enExample) |
| CN (1) | CN102333751A (enExample) |
| BR (1) | BRPI1005353A2 (enExample) |
| CA (1) | CA2749008A1 (enExample) |
| MX (1) | MX2011009028A (enExample) |
| WO (1) | WO2010099144A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103073407A (zh) * | 2013-02-05 | 2013-05-01 | 芜湖市联合涂料有限责任公司 | 三氯化铟催化制备2,4-二羟基二苯甲酮的方法 |
| CN104961633A (zh) * | 2015-05-25 | 2015-10-07 | 武汉怡兴化工股份有限公司 | 4,4′-二羟基二苯甲酮的氢氟酸工艺 |
| WO2021039558A1 (ja) * | 2019-08-27 | 2021-03-04 | Dic株式会社 | フェノール樹脂、硬化性樹脂組成物及びその硬化物 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4245082A (en) | 1979-07-09 | 1981-01-13 | E. I. Du Pont De Nemours And Company | Polyesters derived from 3,4'-dihydroxy-benzophenones or 3-hydroxy-4'-(4-hydroxyphenyl-)benzophenone and certain aromatic dicarboxylic acids and filaments thereof |
| JPS5548217A (en) * | 1978-08-08 | 1980-04-05 | Du Pont | Polymer derived from 3*4**dihydroxybenzophenone or 33hydroxyy4***4hydroxyphenyll*benzophenone and kind of aromatic dicarbon and its filament |
| US4269965A (en) * | 1979-09-17 | 1981-05-26 | E. I. Du Pont De Nemours And Company | Aromatic polyester which forms optically anisotropic melts and filaments thereof |
| ES8306085A1 (es) * | 1981-07-08 | 1983-05-01 | Raychem Corp | "un procedimiento para la preparacion de cetonas aromaticas". |
| JPS59190943A (ja) * | 1983-04-12 | 1984-10-29 | Shipuro Kasei Kk | ポリヒドロキシベンゾフエノン類の製造方法 |
| US4500699A (en) | 1984-06-26 | 1985-02-19 | E. I. Du Pont De Nemours And Company | Optically anisotropic melt forming copolyesters |
| US4617369A (en) * | 1985-09-04 | 1986-10-14 | E. I. Du Pont De Nemours And Company | Polyester polymers of 3-hydroxy-4'-(4-hydroxyphenyl)benzophenone or 3,4'-dihydroxybenzophenone and dicarboxylic acids |
| JPH03123752A (ja) * | 1989-10-06 | 1991-05-27 | Honsyu Kagaku Kogyo Kk | ４，４′―ジヒドロキシベンゾフェノンの製造法 |
| UA79182C2 (en) * | 2002-12-13 | 2007-05-25 | Basf Ag | Method for the production of benzophenones |
-
2009
- 2009-02-26 US US12/393,310 patent/US7772441B1/en not_active Expired - Fee Related
-
2010
- 2010-02-24 BR BRPI1005353A patent/BRPI1005353A2/pt not_active IP Right Cessation
- 2010-02-24 MX MX2011009028A patent/MX2011009028A/es not_active Application Discontinuation
- 2010-02-24 JP JP2011552093A patent/JP5480918B2/ja not_active Expired - Fee Related
- 2010-02-24 CN CN2010800091180A patent/CN102333751A/zh active Pending
- 2010-02-24 WO PCT/US2010/025146 patent/WO2010099144A1/en not_active Ceased
- 2010-02-24 EP EP10705525.3A patent/EP2401249B1/en not_active Not-in-force
- 2010-02-24 KR KR1020117022248A patent/KR20110122749A/ko not_active Withdrawn
- 2010-02-24 CA CA2749008A patent/CA2749008A1/en not_active Abandoned
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