WO2002064544A1 - Procede de production de 1,3-bis(3-aminophenoxy)benzene - Google Patents
Procede de production de 1,3-bis(3-aminophenoxy)benzene Download PDFInfo
- Publication number
- WO2002064544A1 WO2002064544A1 PCT/JP2002/001183 JP0201183W WO02064544A1 WO 2002064544 A1 WO2002064544 A1 WO 2002064544A1 JP 0201183 W JP0201183 W JP 0201183W WO 02064544 A1 WO02064544 A1 WO 02064544A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- aminophenoxy
- benzene
- bis
- reaction
- difluorobenzene
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
Definitions
- the present invention relates to the production of heat-resistant polymers, particularly polyester raw materials, and useful polyether polyamines, especially 1,3-bis (3-aminophenoxy) benzene useful as an adhesive polyimide resin raw material. It relates to a method and its production intermediate. Background art
- JP-A-H03-355085 1, 3, 5-trichlorobenzene is reacted with an aluminum metal salt of 3-aminophenol to form two ether bonds. After decomposing, hydrogenolysis is carried out using a noble metal catalyst, and the remaining crotch group is eliminated.
- benzene with an extra electron-attracting chlor group is used in order to increase the substitution reactivity of the chlor group. For this reason, the number of processes was two, which was not satisfactory for industrial manufacturing.
- sodium salts and potassium salts can be simultaneously used as alkali metal salts. It has been found that when used in combination, the reaction time is significantly shortened, and the present invention has been completed.
- reaction temperature 150 to 280 degreeC is preferable.
- the intermediate of the reaction is 1- (3-aminophenoxy) -3-fluorobenzene.
- the 1,3-bis (3-aminophenoxy) can be directly obtained from the 1,3-difluorobenzene and the 3-aminophenol in a high yield. It can produce benzene.
- the alkaline metal salt of 3-aminophenol used in the present invention is preferably a sodium salt or potassium salt, and 3-aminophenol and sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate and sodium bicarbonate. It is easily prepared by the reaction with alkali metal salts such as potassium carbonate and potassium hydrogen carbonate, and alkali metal alkoxides such as sodium methylate and potassium potassium tert-butoxide.
- the amount of the metal salt of 3-aminophenyl is preferably at least 2 moles, more preferably at least 2.1 moles, and more preferably at most 10 moles, of 1, 3-difluorinated benzene. Preferably, 5 moles or less is more preferred. If it is less than this, the fluoro group will be left unsubstituted and the purpose of converting all fluoro groups into ether bonds can not be achieved. If it is more than this, it is uneconomical.
- the combination of sodium salt of 3-aminophenol and potassium salt can significantly reduce the reaction time.
- the ratio is preferably 9/1 to; L / 9 in terms of a molar ratio of sodium salt / force salt and more preferably 7/3 to 3/7.
- the solvent for example, acetylonitrile, N-methylformaldehyde, N, N-dimethylformaldehyde, N, N-dimethylacetamide, dimethylsulfoxide, dimethylsulfone, sulfolane, N-methylpyrrolidone,
- Non-protonic polar solvents such as 1, 3 -dimethyl 12-imidazolidinone (hereinafter abbreviated as DMI) can be used, but among them, N, N-dimethylformaldehyde, dimethylsulfoxide, sulfur Luhoran, DMI is preferred.
- the amount of the solvent to be used is not particularly limited, but is preferably 0.5 times by mass or more, more preferably 1.0 times by mass or more, and preferably 10 times by mass or less, with respect to 3-aminophenol. A mass ratio of 5.0 or less is more preferable.
- the reaction temperature is preferably 150 ° C. or more, more preferably 180 ° C. or more, and preferably 280 ° C. or less, more preferably 240 ° C. or less. If the temperature is lower than this, the reaction becomes slow and slow and not practical. If the temperature is too high, decomposition of the metal salt of 3-aminophenol occurs.
- the preparation of an aluminum metal salt of 3-aminophenyl and the reaction with 1,3-difluorobenzene are preferably carried out under a nitrogen atmosphere in order to prevent oxidation of 3-aminophenol and the desired compound.
- mixing of water Since it causes the formation of impurities, it is preferable to dehydrate the alkali metal salt as much as possible by a method such as azeotropic dewatering if necessary.
- reaction mixture After completion of the reaction, the reaction mixture is extracted with an organic solvent, and then the solvent is distilled off and concentrated, or the reaction mixture is discharged into water.
- the resulting crude product is purified by a conventional method such as recrystallization, distillation or column chromatography.
- a conventional method such as recrystallization, distillation or column chromatography.
- reaction mass was filtered and washed with toluene.
- 300 g of toluene was added, water washing was repeated using 300 g of water, and the organic layer was concentrated to obtain an oil of 63.2 g.
- 1,3-bis (3-aminophenoxy) benzene can be produced with high yield in one step.
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)
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE60222835T DE60222835T2 (de) | 2001-02-13 | 2002-02-13 | Verfahren zur herstellung von 1,3-bis(3-aminophenoxy)benzol |
EP02712311A EP1270546B1 (en) | 2001-02-13 | 2002-02-13 | Process for producing 1,3-bis(3-aminophenoxy)benzene |
US10/220,708 US6664425B2 (en) | 2001-02-13 | 2002-02-13 | Process for producing 1,3-bis(3-aminophenoxy)benzene |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001-35708 | 2001-02-13 | ||
JP2001035708 | 2001-02-13 | ||
JP2002-3175 | 2002-01-10 | ||
JP2002003175 | 2002-01-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002064544A1 true WO2002064544A1 (fr) | 2002-08-22 |
Family
ID=26609320
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2002/001183 WO2002064544A1 (fr) | 2001-02-13 | 2002-02-13 | Procede de production de 1,3-bis(3-aminophenoxy)benzene |
Country Status (7)
Country | Link |
---|---|
US (1) | US6664425B2 (ja) |
EP (1) | EP1270546B1 (ja) |
KR (1) | KR100493633B1 (ja) |
CN (1) | CN1239470C (ja) |
DE (1) | DE60222835T2 (ja) |
TW (1) | TWI276621B (ja) |
WO (1) | WO2002064544A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8135995B2 (en) * | 2007-10-19 | 2012-03-13 | Oracle International Corporation | Diagnostic data repository |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4222962A (en) * | 1978-12-11 | 1980-09-16 | Gulf Research & Development Company | Process for preparing a substituted diphenoxybenzene |
EP0034402A2 (en) * | 1980-02-05 | 1981-08-26 | Imperial Chemical Industries Plc | Method of preparing fluorine-substituted diphenyl ether derivatives and fluorine-substituted halogeno benzene derivatives for use therein |
JPH05271167A (ja) * | 1992-03-24 | 1993-10-19 | Central Glass Co Ltd | 4,4’−ビス(テトラフルオロアミノフェノキシ)オクタフルオロビフェニルおよびその製造法 |
JPH07309817A (ja) * | 1994-05-19 | 1995-11-28 | Mitsui Toatsu Chem Inc | 1,3,5−トリス(3−アミノフェノキシ)ベンゼン誘導体の製造法 |
-
2002
- 2002-02-13 KR KR10-2002-7013565A patent/KR100493633B1/ko active IP Right Grant
- 2002-02-13 US US10/220,708 patent/US6664425B2/en not_active Expired - Lifetime
- 2002-02-13 DE DE60222835T patent/DE60222835T2/de not_active Expired - Lifetime
- 2002-02-13 EP EP02712311A patent/EP1270546B1/en not_active Expired - Lifetime
- 2002-02-13 CN CNB028002474A patent/CN1239470C/zh not_active Expired - Lifetime
- 2002-02-13 WO PCT/JP2002/001183 patent/WO2002064544A1/ja active IP Right Grant
- 2002-02-15 TW TW091102597A patent/TWI276621B/zh not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4222962A (en) * | 1978-12-11 | 1980-09-16 | Gulf Research & Development Company | Process for preparing a substituted diphenoxybenzene |
EP0034402A2 (en) * | 1980-02-05 | 1981-08-26 | Imperial Chemical Industries Plc | Method of preparing fluorine-substituted diphenyl ether derivatives and fluorine-substituted halogeno benzene derivatives for use therein |
JPH05271167A (ja) * | 1992-03-24 | 1993-10-19 | Central Glass Co Ltd | 4,4’−ビス(テトラフルオロアミノフェノキシ)オクタフルオロビフェニルおよびその製造法 |
JPH07309817A (ja) * | 1994-05-19 | 1995-11-28 | Mitsui Toatsu Chem Inc | 1,3,5−トリス(3−アミノフェノキシ)ベンゼン誘導体の製造法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP1270546A4 * |
Also Published As
Publication number | Publication date |
---|---|
KR20020093899A (ko) | 2002-12-16 |
EP1270546B1 (en) | 2007-10-10 |
US6664425B2 (en) | 2003-12-16 |
EP1270546A4 (en) | 2005-12-28 |
DE60222835T2 (de) | 2008-01-24 |
US20030078454A1 (en) | 2003-04-24 |
KR100493633B1 (ko) | 2005-06-03 |
DE60222835D1 (de) | 2007-11-22 |
TWI276621B (en) | 2007-03-21 |
CN1457336A (zh) | 2003-11-19 |
CN1239470C (zh) | 2006-02-01 |
EP1270546A1 (en) | 2003-01-02 |
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