RU2014145135A - Способ получения (этин-1,2-диил)бис(изобензофуран-1,3-диона) - Google Patents
Способ получения (этин-1,2-диил)бис(изобензофуран-1,3-диона) Download PDFInfo
- Publication number
- RU2014145135A RU2014145135A RU2014145135A RU2014145135A RU2014145135A RU 2014145135 A RU2014145135 A RU 2014145135A RU 2014145135 A RU2014145135 A RU 2014145135A RU 2014145135 A RU2014145135 A RU 2014145135A RU 2014145135 A RU2014145135 A RU 2014145135A
- Authority
- RU
- Russia
- Prior art keywords
- dione
- bis
- isobenzofuran
- diyl
- ethin
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 32
- 238000005406 washing Methods 0.000 claims abstract 18
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract 8
- -1 chloro- Chemical class 0.000 claims abstract 7
- 239000011541 reaction mixture Substances 0.000 claims abstract 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000003054 catalyst Substances 0.000 claims abstract 5
- 229910052763 palladium Inorganic materials 0.000 claims abstract 5
- RZNRHYDJQKHHOQ-UHFFFAOYSA-N 4-[2-(1,3-dioxo-2-benzofuran-4-yl)ethynyl]-2-benzofuran-1,3-dione Chemical compound O=C1OC(=O)C2=C1C=CC=C2C#CC1=CC=CC2=C1C(=O)OC2=O RZNRHYDJQKHHOQ-UHFFFAOYSA-N 0.000 claims abstract 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000000010 aprotic solvent Substances 0.000 claims abstract 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract 3
- 235000019253 formic acid Nutrition 0.000 claims abstract 3
- 238000000926 separation method Methods 0.000 claims abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
- 239000000460 chlorine Substances 0.000 claims abstract 2
- 239000011630 iodine Substances 0.000 claims abstract 2
- 229910052740 iodine Inorganic materials 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000001879 copper Chemical class 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- BCKVHOUUJMYIAN-UHFFFAOYSA-N 5-bromo-2-benzofuran-1,3-dione Chemical compound BrC1=CC=C2C(=O)OC(=O)C2=C1 BCKVHOUUJMYIAN-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- WXNOJTUTEXAZLD-UHFFFAOYSA-L benzonitrile;dichloropalladium Chemical compound Cl[Pd]Cl.N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 WXNOJTUTEXAZLD-UHFFFAOYSA-L 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12164900.8A EP2653467B1 (en) | 2012-04-20 | 2012-04-20 | Process for producing (ethyne-1,2-diyl)bis(isobenzofuran-1,3- dione) |
| EP12164900.8 | 2012-04-20 | ||
| PCT/EP2013/054686 WO2013156200A1 (en) | 2012-04-20 | 2013-03-08 | Process for producing (ethyne-1,2-diyl)bis(isobenzofuran-1,3- dione) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014145135A true RU2014145135A (ru) | 2016-06-10 |
Family
ID=47843291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014145135A RU2014145135A (ru) | 2012-04-20 | 2013-03-08 | Способ получения (этин-1,2-диил)бис(изобензофуран-1,3-диона) |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9018401B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2653467B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6138237B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102081717B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN104245685B (cg-RX-API-DMAC7.html) |
| ES (1) | ES2523824T3 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2014145135A (cg-RX-API-DMAC7.html) |
| TW (1) | TW201406741A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2013156200A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160208097A1 (en) | 2015-01-15 | 2016-07-21 | Rohm And Haas Electronic Materials Llc | Polyimide compositions and methods |
| JP6750146B2 (ja) * | 2015-10-13 | 2020-09-02 | 株式会社ピーアイ技術研究所 | 電着用ポリイミド及びそれを含む電着塗料組成物 |
| CN109575019B (zh) * | 2018-12-26 | 2020-04-14 | 苏州闻智生物科技有限公司 | 一种5-溴-7-氮杂吲哚的制备方法 |
| CN117304149B (zh) * | 2023-09-28 | 2025-12-12 | 常州市尚科新材料有限公司 | 4-苯乙炔苯酐的合成方法 |
| CN119506538A (zh) * | 2024-11-18 | 2025-02-25 | 马鞍山钢铁股份有限公司 | 一种取向硅钢酸洗卷及其制备方法、取向硅钢成品 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956322A (en) | 1975-03-14 | 1976-05-11 | General Electric Company | Dianhydrides of bis-(orthodicarboxyphenyloxyphenyl)acetylene and bis-(ortho-dicarboxyphenyloxyphenyl)2,2-dichloroethylene |
| US3983093A (en) | 1975-05-19 | 1976-09-28 | General Electric Company | Novel polyetherimides |
| US4973707A (en) | 1989-07-31 | 1990-11-27 | General Electric Company | Acetylene bis-phthalic compounds and polyimides made therefrom |
| DE3936297A1 (de) | 1989-11-01 | 1991-05-02 | Bayer Ag | Verfahren zur herstellung von symmetrischen diarylacetylenen |
| US5567800A (en) | 1994-10-28 | 1996-10-22 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Imide oligomers endcapped with phenylethynyl phthalic anhydrides and polymers therefrom |
| JPH11180970A (ja) * | 1997-12-17 | 1999-07-06 | Mitsui Chem Inc | 炭素炭素三重結合を有するジカルボン酸無水物の製造方法 |
| JP4913962B2 (ja) * | 2001-08-30 | 2012-04-11 | マナック株式会社 | フェニルエチニルフタル酸無水物誘導体の製造方法 |
| JP4299521B2 (ja) * | 2002-09-30 | 2009-07-22 | 富士フイルム株式会社 | エチニル基を有する無水フタル酸化合物およびその製造方法 |
| JP4574403B2 (ja) * | 2004-03-25 | 2010-11-04 | 富士フイルム株式会社 | アリールエチニルフタル酸誘導体及び該誘導体の製造方法 |
| US7015304B1 (en) * | 2004-07-23 | 2006-03-21 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Solvent free low-melt viscosity imide oligomers and thermosetting polyimide composites |
| CN1312145C (zh) * | 2004-08-03 | 2007-04-25 | 上海市合成树脂研究所 | 4－苯乙炔苯酐的制备方法 |
| JP2006151903A (ja) * | 2004-11-30 | 2006-06-15 | Fuji Photo Film Co Ltd | エチニルフタル酸無水物誘導体及びエチニルフタル酸誘導体の製造方法 |
| CN101550121A (zh) * | 2008-04-01 | 2009-10-07 | 四川大学 | 由4-溴邻苯二甲酸制备4-苯乙炔邻苯二甲酸酐的方法 |
| JP5485890B2 (ja) * | 2008-07-31 | 2014-05-07 | マナック株式会社 | 無水フタル酸誘導体の製造方法 |
| CN102844291B (zh) | 2010-04-16 | 2015-06-17 | 聂克斯姆化学有限公司 | 新型交联剂 |
| EP2569343B1 (en) * | 2010-05-14 | 2015-07-08 | Nexam Chemical AB | Catalysis of cross-linking |
| WO2012131063A1 (en) | 2011-04-01 | 2012-10-04 | Nexam Chemical Ab | Improved oligo- and polyimides |
-
2012
- 2012-04-20 EP EP12164900.8A patent/EP2653467B1/en active Active
- 2012-04-20 ES ES12164900.8T patent/ES2523824T3/es active Active
-
2013
- 2013-03-08 KR KR1020147032487A patent/KR102081717B1/ko active Active
- 2013-03-08 CN CN201380020284.4A patent/CN104245685B/zh active Active
- 2013-03-08 RU RU2014145135A patent/RU2014145135A/ru unknown
- 2013-03-08 JP JP2015506134A patent/JP6138237B2/ja active Active
- 2013-03-08 US US14/394,489 patent/US9018401B2/en active Active
- 2013-03-08 WO PCT/EP2013/054686 patent/WO2013156200A1/en not_active Ceased
- 2013-04-19 TW TW102113926A patent/TW201406741A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20150015466A (ko) | 2015-02-10 |
| TW201406741A (zh) | 2014-02-16 |
| EP2653467A1 (en) | 2013-10-23 |
| WO2013156200A1 (en) | 2013-10-24 |
| JP2015514730A (ja) | 2015-05-21 |
| KR102081717B1 (ko) | 2020-02-26 |
| US9018401B2 (en) | 2015-04-28 |
| CN104245685B (zh) | 2016-09-07 |
| JP6138237B2 (ja) | 2017-05-31 |
| EP2653467B1 (en) | 2014-09-03 |
| CN104245685A (zh) | 2014-12-24 |
| ES2523824T3 (es) | 2014-12-01 |
| US20150080586A1 (en) | 2015-03-19 |
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