JPWO2006048935A1 - 2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニルの製造方法 - Google Patents
2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニルの製造方法 Download PDFInfo
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- JPWO2006048935A1 JPWO2006048935A1 JP2006542207A JP2006542207A JPWO2006048935A1 JP WO2006048935 A1 JPWO2006048935 A1 JP WO2006048935A1 JP 2006542207 A JP2006542207 A JP 2006542207A JP 2006542207 A JP2006542207 A JP 2006542207A JP WO2006048935 A1 JPWO2006048935 A1 JP WO2006048935A1
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- Prior art keywords
- trifluoromethyl
- bis
- reaction
- diaminobiphenyl
- hydrazobenzene
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- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 25
- WTUBIIQFZWOLMV-UHFFFAOYSA-N 1,2-bis[3-(trifluoromethyl)phenyl]hydrazine Chemical compound FC(F)(F)C1=CC=CC(NNC=2C=C(C=CC=2)C(F)(F)F)=C1 WTUBIIQFZWOLMV-UHFFFAOYSA-N 0.000 claims abstract description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 57
- WHNAMGUAXHGCHH-UHFFFAOYSA-N 1-nitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC(C(F)(F)F)=C1 WHNAMGUAXHGCHH-UHFFFAOYSA-N 0.000 abstract description 14
- 239000007864 aqueous solution Substances 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract description 3
- 229920001721 polyimide Polymers 0.000 abstract description 3
- 239000009719 polyimide resin Substances 0.000 abstract description 3
- 239000007810 chemical reaction solvent Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- 238000006722 reduction reaction Methods 0.000 description 19
- 239000007788 liquid Substances 0.000 description 16
- 238000006462 rearrangement reaction Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- -1 and at 0 ° C. Chemical compound 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UVWCIYKTJPSBIX-UHFFFAOYSA-N 1,2-bis[4-(trifluoromethyl)phenyl]hydrazine Chemical compound C1=CC(C(F)(F)F)=CC=C1NNC1=CC=C(C(F)(F)F)C=C1 UVWCIYKTJPSBIX-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- VAHOFXUZOFECLT-UHFFFAOYSA-N 1-phenyl-2-[2-(trifluoromethyl)phenyl]hydrazine Chemical compound FC(F)(F)C1=C(NNC2=CC=CC=C2)C=CC=C1 VAHOFXUZOFECLT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- ODNNWXKHVFFHEI-UHFFFAOYSA-N bis[3-(trifluoromethyl)phenyl]diazene Chemical compound FC(F)(F)C1=CC=CC(N=NC=2C=C(C=CC=2)C(F)(F)F)=C1 ODNNWXKHVFFHEI-UHFFFAOYSA-N 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DHRKBGDIJSRWIP-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3-bis(trifluoromethyl)aniline Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1C(F)(F)F DHRKBGDIJSRWIP-UHFFFAOYSA-N 0.000 description 1
- JPZRPCNEISCANI-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(trifluoromethyl)aniline Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F JPZRPCNEISCANI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
測定条件
カラム:Intersil ODS 80A(ジーエルサイエンス(株)製)
長さ250mm、内径4.2mm
移動相:メタノール(70%)/0.1%リン酸水(30%)→メタノール(100%)/0.1%リン酸水(0%)グラジェント
検出器:UV(254nm)
還流冷却器、温度測定管及び電磁攪拌機を備えた300mlのガラス製反応容器に、窒素雰囲気下、m−ニトロベンゾトリフルオリド20.00gとメタノール152gを仕込み、40%水酸化ナトリウム水溶液46.37gを添加した後、亜鉛末36.0gを仕込んだ。内温を65℃に昇温し、この温度で5時間反応させた。反応後、固形物を濾別し、反応濾液を得た。濾液中のメタノールを除去した後、水洗してトルエンで抽出後、脱溶媒して16.76gの淡黄色液体を得た。この淡黄色液体を分析した結果、純度96.4%の3,3’−ビス(トリフルオロメチル)ヒドラゾベンゼンが、m−ニトロベンゾトリフルオリド基準の収率96.4%で分離された。
還流冷却器、温度測定管及び電磁攪拌機を備えた300mlのガラス製反応容器に、窒素雰囲気下、m−ニトロベンゾトリフルオリド20.00gとメタノール156gを仕込み、40%水酸化ナトリウム水溶液48.6gを添加した後、亜鉛末21.7gを仕込んだ。内温を65℃に昇温し、この温度で5時間反応させた。反応後、固形物を濾別し、反応濾液を得た。濾液中のメタノールを除去した後、クロロホルム423gで抽出後、脱溶媒して30.5gの淡黄色液体を得た。この淡黄色液体をアセトン190gに溶解し、攪拌下に亜鉛末14.3gを添加した後、28%塩化アンモニウム水溶液75gを滴下した。反応液の色相が黄褐色から無色になるまで保持した後、10%アンモニア水溶液中に滴下した。1.0時間保持した後、クロロホルムで抽出し、抽出液を脱溶媒して淡褐色の液体17.2gを得た。この淡褐色の液体を分析した結果、3,3’−ビス(トリフルオロメチル)ヒドラゾベンゼンの純度は93.0%であった。これはm−ニトロベンゾトリフルオリド基準の収率は95.5%であった。
実施例1の還元反応で得た淡褐色液体8.71gを29.0gのトルエンに溶解し、濃塩酸22.1g中に25℃に保ちながら滴下し、滴下後、25℃で3時間、転位反応させた。反応後中和し、トルエンで抽出して86.1gのトルエン層を得た。トルエン層を分析した結果、2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニルの濃度は2.48%であり、還元反応で得た淡褐色液体中の3,3’−ビス(トリフルオロメチル)ヒドラゾベンゼン基準の収率は25.4%であった。
実施例1と同様の還元反応で得た淡褐色液体4.50gを37.5gのエタノールに溶解したものに、0℃で濃塩酸5.53gを滴下し、滴下後24時間、転位反応させた。50.7gの反応液を回収し、分析した結果、2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニル濃度は0.21%であり、還元反応で得た淡褐色液体中の3,3’−ビス(トリフルオロメチル)ヒドラゾベンゼン基準の収率は2.4%であった。
実施例1と同様の還元反応で得た淡褐色液体4.50gを26.0gのエタノールに溶解したものに、室温下で50%硫酸水溶液13.6gを滴下し、滴下後12時間、転位反応させた。43.6gの反応液を回収し分析した結果、2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニルの濃度は0.95%であり、還元反応で得た淡褐色液体中の3,3’−ビス(トリフルオロメチル)ヒドラゾベンゼン基準の収率は9.5%であった。
Claims (5)
- 3,3’−ビス(トリフルオロメチル)ヒドラゾベンゼンを、水と非混和性の有機溶媒中で無機酸の存在下で転位させることを特徴とする2,2’−ビス(トリフルオロメチル)−4、4’−ジアミノビフェニルの製造方法。
- 水と非混和性の有機溶媒が、炭化水素である請求項1記載の2,2’−(ビストリフルオロメチル)−4、4’−ジアミノビフェニルの製造方法。
- 炭化水素が、芳香族炭化水素である請求項2記載の2,2’−ビス(トリフルオロメチル)−4、4’−ジアミノビフェニルの製造方法。
- 無機酸が、濃度が10〜80重量%の硫酸水溶液又は濃塩酸である請求項1〜3記載の2,2’−ビス(トリフルオロメチル)−4、4’−ジアミノビフェニルの製造方法。
- 無機酸を、3,3’−ビス(トリフルオロメチル)ヒドラゾベンゼン1モルに対し、1〜20モル使用することを特徴とする請求項4記載の2,2’−ビス(トリフルオロメチル)−4、4’−ジアミノビフェニルの製造方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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PCT/JP2004/016403 WO2006048935A1 (ja) | 2004-11-05 | 2004-11-05 | 2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニルの製造方法 |
Publications (2)
Publication Number | Publication Date |
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JPWO2006048935A1 true JPWO2006048935A1 (ja) | 2008-05-22 |
JP4738345B2 JP4738345B2 (ja) | 2011-08-03 |
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Family Applications (1)
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JP2006542207A Expired - Fee Related JP4738345B2 (ja) | 2004-11-05 | 2004-11-05 | 2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニルの製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7772436B2 (ja) |
EP (1) | EP1816118B1 (ja) |
JP (1) | JP4738345B2 (ja) |
CN (1) | CN101102992B (ja) |
AT (1) | ATE456550T1 (ja) |
DE (1) | DE602004025393D1 (ja) |
WO (1) | WO2006048935A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102417459B (zh) * | 2011-08-29 | 2014-03-05 | 天津市筠凯化工科技有限公司 | 2,2′-双三氟甲基-4,4′-二氨基联苯制备新方法 |
CN109232273A (zh) * | 2018-10-23 | 2019-01-18 | 烟台海川化学制品有限公司 | 一种2,2'-双(三氟甲基)-4,4'-二氨基联苯的制备方法 |
CN109535005B (zh) * | 2018-12-29 | 2022-01-25 | 山东华夏神舟新材料有限公司 | 2,2’-双三氟甲基-4,4’-二氨基联苯的制备方法 |
CN110590596B (zh) * | 2019-10-01 | 2022-03-22 | 常州市阳光药业有限公司 | 4,4’-二氨基-2,2’-二甲基-1,1’-联苯的制备方法 |
WO2021131549A1 (ja) | 2019-12-26 | 2021-07-01 | セイカ株式会社 | ジアミノビフェニル化合物の製造方法 |
CN113024385B (zh) * | 2021-03-16 | 2022-08-16 | 西安瑞联新材料股份有限公司 | 一种2,2'-双(三氟甲基)-4,4'-二氨基联苯的制备方法 |
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---|---|---|---|---|
JPS5758647A (en) * | 1980-08-01 | 1982-04-08 | Hoechst Ag | Continuous manufacture of diphenyl base |
JPS5823650A (ja) * | 1976-03-08 | 1983-02-12 | バイエル・アクチエンゲゼルシヤフト | 4,4′−ジアミノジフエニル誘導体の製法 |
JPS61229846A (ja) * | 1985-03-29 | 1986-10-14 | ヘキスト・アクチエンゲゼルシヤフト | 4,4′―ジアミノジフェニル化合物 |
JPH05500812A (ja) * | 1989-11-09 | 1993-02-18 | ヘキスト・アクチェンゲゼルシャフト | 3,3′―ジクロル―ベンジジン―ジヒドロクロリドの連続的製法 |
JP2006143703A (ja) * | 2004-10-20 | 2006-06-08 | Air Water Chemical Inc | 2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニルの製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1633123A (en) * | 1920-06-22 | 1927-06-21 | Nat Aniline & Chem Co Inc | Production of benzidine and derivatives |
US1718373A (en) * | 1920-06-22 | 1929-06-25 | Nat Aniline & Chem Co Inc | Production of benzidine and derivatives |
US4987258A (en) * | 1985-03-29 | 1991-01-22 | Hoechst Aktiengesellschaft | 4,4'-diaminodiphenyl compounds, process for their preparation and their use |
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2004
- 2004-11-05 CN CN2004800443540A patent/CN101102992B/zh not_active Expired - Fee Related
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5823650A (ja) * | 1976-03-08 | 1983-02-12 | バイエル・アクチエンゲゼルシヤフト | 4,4′−ジアミノジフエニル誘導体の製法 |
JPS5758647A (en) * | 1980-08-01 | 1982-04-08 | Hoechst Ag | Continuous manufacture of diphenyl base |
JPS61229846A (ja) * | 1985-03-29 | 1986-10-14 | ヘキスト・アクチエンゲゼルシヤフト | 4,4′―ジアミノジフェニル化合物 |
JPH05500812A (ja) * | 1989-11-09 | 1993-02-18 | ヘキスト・アクチェンゲゼルシャフト | 3,3′―ジクロル―ベンジジン―ジヒドロクロリドの連続的製法 |
JP2006143703A (ja) * | 2004-10-20 | 2006-06-08 | Air Water Chemical Inc | 2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニルの製造方法 |
Non-Patent Citations (1)
Title |
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JPN6011002909, Journal of Polymer Science, Part A: Polymer Chemistry, 1999, 37(7), p.937−957 * |
Also Published As
Publication number | Publication date |
---|---|
EP1816118B1 (en) | 2010-01-27 |
JP4738345B2 (ja) | 2011-08-03 |
US7772436B2 (en) | 2010-08-10 |
ATE456550T1 (de) | 2010-02-15 |
CN101102992B (zh) | 2011-06-29 |
EP1816118A4 (en) | 2008-01-02 |
EP1816118A1 (en) | 2007-08-08 |
DE602004025393D1 (de) | 2010-03-18 |
WO2006048935A1 (ja) | 2006-05-11 |
CN101102992A (zh) | 2008-01-09 |
US20090069602A1 (en) | 2009-03-12 |
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