JP2007045820A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2007045820A5 JP2007045820A5 JP2006210193A JP2006210193A JP2007045820A5 JP 2007045820 A5 JP2007045820 A5 JP 2007045820A5 JP 2006210193 A JP2006210193 A JP 2006210193A JP 2006210193 A JP2006210193 A JP 2006210193A JP 2007045820 A5 JP2007045820 A5 JP 2007045820A5
- Authority
- JP
- Japan
- Prior art keywords
- hexafluoro
- bis
- isopropyl
- hydroxy
- copper
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 34
- QARVLSVVCXYDNA-UHFFFAOYSA-N Bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 31
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 28
- 239000010949 copper Substances 0.000 claims description 24
- 229910052802 copper Inorganic materials 0.000 claims description 24
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 23
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 20
- 238000006460 hydrolysis reaction Methods 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 150000002894 organic compounds Chemical class 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000005893 bromination reaction Methods 0.000 claims description 10
- MMUFAGXJPKNAHT-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1 MMUFAGXJPKNAHT-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- VRLDVERQJMEPIF-UHFFFAOYSA-N DBDMH Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 8
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 8
- 150000001879 copper Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 5
- -1 copper halide salt Chemical class 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- 239000000920 calcium hydroxide Substances 0.000 claims description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 4
- 239000005751 Copper oxide Substances 0.000 claims description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 3
- 229910000431 copper oxide Inorganic materials 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-Bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N 8-Hydroxyquinoline Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- ZUDYPQRUOYEARG-UHFFFAOYSA-L barium(2+);dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Ba+2] ZUDYPQRUOYEARG-UHFFFAOYSA-L 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000000640 hydroxylating Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200510028549.2 | 2005-08-05 | ||
| CNB2005100285492A CN1300076C (zh) | 2005-08-05 | 2005-08-05 | 双(2－羟基六氟丙基)苯酚的制备方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007045820A JP2007045820A (ja) | 2007-02-22 |
| JP2007045820A5 true JP2007045820A5 (zh) | 2009-03-26 |
| JP5036243B2 JP5036243B2 (ja) | 2012-09-26 |
Family
ID=36076331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006210193A Expired - Fee Related JP5036243B2 (ja) | 2005-08-05 | 2006-08-01 | ３，５−ビス（１，１，１，３，３，３−ヘキサフルオロ−２−ヒドロキシイソプロピル）フェノールの製造方法 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP5036243B2 (zh) |
| CN (1) | CN1300076C (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101830793B (zh) * | 2010-05-13 | 2014-01-15 | 中科院广州化学有限公司 | 一种羟基取代苯乙酸类化合物的制备方法 |
| CN103641692B (zh) * | 2013-11-27 | 2015-07-08 | 北京航空航天大学 | 一种含氟双酚化合物的制备 |
| CN105541597B (zh) * | 2015-12-29 | 2018-06-01 | 中山大学 | 一种2,4-二羟基苯乙酸的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH075493B2 (ja) * | 1989-06-26 | 1995-01-25 | セントラル硝子株式会社 | ビス（２―ヒドロキシヘキサフルオロ―２―プロピル）ベンゼン誘導体の製造方法 |
| JP2857745B2 (ja) * | 1996-02-22 | 1999-02-17 | 工業技術院長 | ▲１９ｆ▼−ｎｍｒを用いた生体イメージングのための新規なフッ素含有化合物 |
| WO2000076947A1 (en) * | 1999-06-11 | 2000-12-21 | Merck & Co., Inc. | Process for the synthesis of 3,5-bis(trifluoromethyl)-bromobenzene |
| JP4212307B2 (ja) * | 2002-06-24 | 2009-01-21 | セントラル硝子株式会社 | 含フッ素スチレン重合性単量体の製造方法及びそれに使用される中間体化合物 |
| JP4410508B2 (ja) * | 2002-08-07 | 2010-02-03 | セントラル硝子株式会社 | 含フッ素化合物とその高分子化合物 |
| KR100562442B1 (ko) * | 2002-08-07 | 2006-03-17 | 샌트랄 글래스 컴퍼니 리미티드 | 항반사광 필름재료 및 레지스트 조성물용 플로린 함유 화합물 및 그의 폴리머 |
-
2005
- 2005-08-05 CN CNB2005100285492A patent/CN1300076C/zh active Active
-
2006
- 2006-08-01 JP JP2006210193A patent/JP5036243B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI498318B (zh) | Process for the production of 2-bromo-4,5-dialkoxybenzoic acid | |
| EP1760057A1 (en) | Method for producing polyhalogenated diamantane and derivative thereof | |
| CN109400459B (zh) | 2,4,5-三氟苯乙酸的制备方法 | |
| JP4872668B2 (ja) | ２−アミノ−５−ヨード安息香酸の製造方法 | |
| JPH0625125A (ja) | 安息香酸誘導体類 | |
| JP5036243B2 (ja) | ３，５−ビス（１，１，１，３，３，３−ヘキサフルオロ−２−ヒドロキシイソプロピル）フェノールの製造方法 | |
| JP2007045820A5 (zh) | ||
| JPH10503530A (ja) | ハロ置換芳香族酸の製造方法 | |
| HU186480B (en) | Process for producing e o-(trifluoromethyl)-aniline in four steps, isolated by distillation | |
| JP5248489B2 (ja) | ハロゲン化芳香族化合物の製造方法 | |
| JP2006257042A (ja) | ２−フルオロ−６−（トリフルオロメチル）ベンジルブロミドおよび２−フルオロ−６−（トリフルオロメチル）ベンジルアミンの製造方法 | |
| CN110734368A (zh) | 一种布帕伐醌的制备方法 | |
| JPH03123762A (ja) | ２，４‐または２，６‐ジハロゲノアニリンの製法 | |
| JP2002522522A (ja) | ３，５−ジフルオロアニリンの製造方法 | |
| JP5133270B2 (ja) | １−ブロモ−３−トリフルオロメトキシベンゼンの製法 | |
| JP4551533B2 (ja) | 新規フッ素化剤及びフッ素含有化合物の製造方法 | |
| US7019166B2 (en) | Method for the production of 2,4,5-trimethylphenyl acetic acid | |
| CN110734369B (zh) | 一种阿托伐醌的制备方法 | |
| US20080146839A1 (en) | Method for Producing 5-Halo-2,4,6-Trifluoroisophthalic Acid | |
| JP4956760B2 (ja) | ３−ブロモ安息香酸またはそのアルキルエステルの製造方法 | |
| JP3500504B2 (ja) | ２−ヒドロキシカルバゾールの製造方法 | |
| JP4554130B2 (ja) | ２−ハロ−６−ニトロ安息香酸を製造する方法 | |
| JPH04221328A (ja) | 沃素化９，９−ジアルキルフルオレンの製造方法 | |
| JP4034889B2 (ja) | トリフルオロフェノール類の製造法 | |
| JP2524756B2 (ja) | ２，４−ジクロル−３−メチルフェノ−ルの製造方法 |