CA1163047A - Method for producing polyphenylene oxides - Google Patents
Method for producing polyphenylene oxidesInfo
- Publication number
- CA1163047A CA1163047A CA000324770A CA324770A CA1163047A CA 1163047 A CA1163047 A CA 1163047A CA 000324770 A CA000324770 A CA 000324770A CA 324770 A CA324770 A CA 324770A CA 1163047 A CA1163047 A CA 1163047A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- amine
- oxygen
- gas
- reflux condenser
- 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.)
- Expired
Links
- 239000004721 Polyphenylene oxide Substances 0.000 title claims description 11
- 229920006380 polyphenylene oxide Polymers 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 83
- 150000001412 amines Chemical class 0.000 claims abstract description 41
- 239000007789 gas Substances 0.000 claims abstract description 31
- 238000010992 reflux Methods 0.000 claims abstract description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 16
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000005749 Copper compound Substances 0.000 claims abstract description 8
- 150000001880 copper compounds Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 26
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 8
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 claims description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 23
- 230000035484 reaction time Effects 0.000 abstract description 11
- 238000007796 conventional method Methods 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 150000002989 phenols Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KLAQSPUVCDBEGF-UHFFFAOYSA-N 2,3,5,6-tetramethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1C KLAQSPUVCDBEGF-UHFFFAOYSA-N 0.000 description 2
- CIRRFAQIWQFQSS-UHFFFAOYSA-N 6-ethyl-o-cresol Chemical compound CCC1=CC=CC(C)=C1O CIRRFAQIWQFQSS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- RGWXSQCOYFRTKU-UHFFFAOYSA-N 2,6-didodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC(CCCCCCCCCCCC)=C1O RGWXSQCOYFRTKU-UHFFFAOYSA-N 0.000 description 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 1
- NAILKKRDWBJCNH-UHFFFAOYSA-N 2,6-dipropylphenol Chemical compound CCCC1=CC=CC(CCC)=C1O NAILKKRDWBJCNH-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- -1 polyphenylene Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/44—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols by oxidation of phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3935078A JPS54131698A (en) | 1978-04-04 | 1978-04-04 | Preparation of polyphenylene oxide |
| JP53-39350 | 1978-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1163047A true CA1163047A (en) | 1984-02-28 |
Family
ID=12550621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000324770A Expired CA1163047A (en) | 1978-04-04 | 1979-04-03 | Method for producing polyphenylene oxides |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4211857A (en, 2012) |
| JP (1) | JPS54131698A (en, 2012) |
| CA (1) | CA1163047A (en, 2012) |
| DE (1) | DE2913204A1 (en, 2012) |
| FR (1) | FR2421918A1 (en, 2012) |
| GB (1) | GB2022107B (en, 2012) |
| NL (1) | NL7902661A (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3029429A1 (de) * | 1980-08-02 | 1982-03-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von polyphenylenaethern |
| US4385167A (en) * | 1980-08-04 | 1983-05-24 | General Electric Company | Preparation of polyphenylene ether resins |
| US4463164A (en) * | 1983-02-15 | 1984-07-31 | Borg-Warner Chemicals, Inc. | Process for preparing polyphenylene ethers |
| US4477650A (en) * | 1983-03-25 | 1984-10-16 | General Electric Company | Process for polyphenylene oxide preparation including catalyst pre-mixing |
| DE3313864A1 (de) * | 1983-04-16 | 1984-10-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von polyphenylenoxiden |
| IT1167678B (it) * | 1983-12-05 | 1987-05-13 | Enichimica Spa | Procedimento perfezionato per la produzione di polifenilenossido |
| US4581439A (en) * | 1984-05-29 | 1986-04-08 | General Electric Company | Polyphenylene oxide preparation in an aqueous dispersion |
| JP3238005B2 (ja) * | 1994-06-24 | 2001-12-10 | 三菱製紙株式会社 | ハロゲン化銀写真感光材料 |
| JP4671003B2 (ja) * | 2000-06-02 | 2011-04-13 | 三菱瓦斯化学株式会社 | ポリフェニレンエーテルの製造方法 |
| JP3504587B2 (ja) * | 2000-06-19 | 2004-03-08 | 旭化成ケミカルズ株式会社 | ポリフェニレンエーテルの製造法 |
| US6407200B1 (en) | 2001-06-21 | 2002-06-18 | General Electric Company | Method of preparing a poly(arylene ether), and a poly(arylene ether) prepared thereby |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE635350A (en, 2012) * | 1962-07-24 | |||
| US3257358A (en) * | 1963-07-02 | 1966-06-21 | Du Pont | 2, 6-dichloro-1, 4-polyphenylene ether |
| US3313776A (en) * | 1964-03-13 | 1967-04-11 | Gen Electric | Process for increasing the molecular weight of a polyphenylene ether |
| US3432466A (en) * | 1966-11-14 | 1969-03-11 | Gen Electric | Process of making poly-(2,6-diaryl-1,4-phenylene ethers) |
| JPS5217560B2 (en, 2012) * | 1973-11-02 | 1977-05-16 | ||
| US4028341A (en) * | 1974-02-11 | 1977-06-07 | General Electric Company | Process for the preparation of polyphenylene oxides with hydrolytically stable copper catalysts |
| JPS5217880B2 (en, 2012) * | 1974-05-25 | 1977-05-18 | ||
| JPS51122196A (en) * | 1975-04-18 | 1976-10-26 | Mitsubishi Gas Chem Co Inc | A process for manufacturing polyphenylene ether |
-
1978
- 1978-04-04 JP JP3935078A patent/JPS54131698A/ja active Pending
-
1979
- 1979-03-28 US US06/024,568 patent/US4211857A/en not_active Expired - Lifetime
- 1979-03-29 GB GB7910926A patent/GB2022107B/en not_active Expired
- 1979-04-03 DE DE19792913204 patent/DE2913204A1/de active Granted
- 1979-04-03 CA CA000324770A patent/CA1163047A/en not_active Expired
- 1979-04-03 FR FR7908354A patent/FR2421918A1/fr active Granted
- 1979-04-04 NL NL7902661A patent/NL7902661A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2913204A1 (de) | 1979-10-18 |
| NL7902661A (nl) | 1979-10-08 |
| FR2421918B1 (en, 2012) | 1983-01-07 |
| US4211857A (en) | 1980-07-08 |
| GB2022107B (en) | 1982-07-21 |
| FR2421918A1 (fr) | 1979-11-02 |
| DE2913204C2 (en, 2012) | 1988-06-30 |
| JPS54131698A (en) | 1979-10-12 |
| GB2022107A (en) | 1979-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |