GB1497293A - Preparation of polymer using copper catalysts - Google Patents
Preparation of polymer using copper catalystsInfo
- Publication number
- GB1497293A GB1497293A GB385175A GB385175A GB1497293A GB 1497293 A GB1497293 A GB 1497293A GB 385175 A GB385175 A GB 385175A GB 385175 A GB385175 A GB 385175A GB 1497293 A GB1497293 A GB 1497293A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- oxygen
- bromine
- copper
- bromide
- 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
- 239000003054 catalyst Substances 0.000 title abstract 2
- 229920000642 polymer Polymers 0.000 title abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title 1
- 229910052802 copper Inorganic materials 0.000 title 1
- 239000010949 copper Substances 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 abstract 2
- 229940074995 bromine Drugs 0.000 abstract 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 229920001955 polyphenylene ether Polymers 0.000 abstract 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 abstract 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 abstract 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 abstract 1
- ZLVFYUORUHNMBO-UHFFFAOYSA-N 4-bromo-2,6-dimethylphenol Chemical compound CC1=CC(Br)=CC(C)=C1O ZLVFYUORUHNMBO-UHFFFAOYSA-N 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 abstract 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940116318 copper carbonate Drugs 0.000 abstract 1
- 229910001431 copper ion Inorganic materials 0.000 abstract 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 abstract 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 abstract 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 abstract 1
- 229940112669 cuprous oxide Drugs 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229940075581 sodium bromide Drugs 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 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)
Abstract
1497293 Polyphenylene ethers GENERAL ELECTRIC CO 29 Jan 1975 [11 Feb 1974] 3851/75 Heading C3R Polyphenylene ethers are obtained by reacting alkyl-substituted monohydric phenols with oxygen or a gas containing elemental oxygen, in a liquid reaction mixture in the presence of a copper-amine complex comprising: (a) copper ions, (b) bromide ions, (c) a diamine having the formula R b HN-R a -NHR c where R a is C 2-4 - alkylene or C 3-7 -cycloalkylene and R b and R c are isopropyl or C 4-8 -tertiary alkyl, including cycloalkyl, in which only the α-carbon atom has no hydrogens, there being at least two and no more than three carbon atoms separating the two nitrogen atoms, and (d) a tertiary amine which is N-methylpyrrolidine, triethylenediamine or a trialkylamine wherein at least two of the alkyl groups are methyl and the third is C 1-8 primary or C 3-8 secondary alkyl, wherein the molar ratio of (b) to (a) is at least 1 and the ratio of equivalents of (d) to moles of (a) is at least 6. In examples polymers are obtained from 2,6-dimethylphenol in benzene by reaction with oxygen, the catalysts being prepared from cupric bromide, copper carbonate and bromine, cuprous oxide and bromine, sodium bromide, N,N<SP>1</SP>-di-t-butylethylenediamine and N,N<SP>1</SP>-dimethyl-n-butylamine, in some instances tricaprylmonomethyl-ammonium chloride is present as a phase transfer agent and in others 4- bromo-2,6-xylenol is present to increase the bromine content.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44129574A | 1974-02-11 | 1974-02-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1497293A true GB1497293A (en) | 1978-01-05 |
Family
ID=23752332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB385175A Expired GB1497293A (en) | 1974-02-11 | 1975-01-29 | Preparation of polymer using copper catalysts |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5853012B2 (en) |
| DE (1) | DE2505328C2 (en) |
| FR (1) | FR2260594B1 (en) |
| GB (1) | GB1497293A (en) |
| IT (1) | IT1031361B (en) |
| NL (1) | NL178881C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3741038A1 (en) * | 1986-12-04 | 1988-06-09 | Asahi Chemical Ind | METHOD FOR PRODUCING POLYPHENYLENE ETHERS |
| US8288501B2 (en) | 2008-04-18 | 2012-10-16 | Asahi Kasei Chemicals Corporation | Method for producing polyphenylene ether |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51122196A (en) * | 1975-04-18 | 1976-10-26 | Mitsubishi Gas Chem Co Inc | A process for manufacturing polyphenylene ether |
| US4026870A (en) * | 1976-01-21 | 1977-05-31 | General Electric Company | Extraction of copper catalyst from polyphenylene oxide solutions |
| US4097462A (en) * | 1976-01-23 | 1978-06-27 | General Electric Company | Process for making polyphenylene oxides |
| US4059568A (en) * | 1976-08-30 | 1977-11-22 | General Electric Company | Method for the control of diamine catalyzed polyphenylene ether polymerization |
| US4092294A (en) * | 1976-08-30 | 1978-05-30 | General Electric Company | Method for preparing polyphenylene ethers |
| US4043060A (en) * | 1976-08-30 | 1977-08-23 | Caterpillar Tractor Co. | Combination strengthened loader bucket and replaceable cutting edge |
| DE3113096A1 (en) * | 1981-04-01 | 1982-10-21 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING POLYPHENYLENE ETHERS |
| DE3314711A1 (en) * | 1982-04-24 | 1983-10-27 | Basf Ag, 6700 Ludwigshafen | Process for the preparation of polyphenylene ethers |
| BR8306198A (en) * | 1982-11-16 | 1984-07-31 | Gen Electric | CATALYTIC COMPOSITION USED FOR THE PREPARATION OF POLYPHENYLENE ETER RESIN AND IMPROVEMENT IN PROCESS FOR THE PREPARATION OF Said POLYPHENYLENE ETER RESIN |
| US4471068A (en) * | 1983-03-11 | 1984-09-11 | General Electric Company | Process and catalyst for preparation of polyphenylene oxide |
| DE3313864A1 (en) * | 1983-04-16 | 1984-10-18 | Chemische Werke Hüls AG, 4370 Marl | METHOD FOR PRODUCING POLYPHENYLENE OXIDES |
| DE3414236A1 (en) * | 1984-04-14 | 1985-10-24 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING POLYPHENYLENE ETHERS AND THE USE THEREOF FOR PRODUCING MOLDED PARTS |
| DE3414237A1 (en) * | 1984-04-14 | 1985-10-24 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING POLYPHENYLENE ETHERS AND THE USE THEREOF FOR PRODUCING MOLDED PARTS |
| WO2007139172A1 (en) | 2006-05-25 | 2007-12-06 | Mitsubishi Gas Chemical Company, Inc. | Method for producing phenylene ether oligomer |
-
1975
- 1975-01-29 GB GB385175A patent/GB1497293A/en not_active Expired
- 1975-01-31 IT IT1983675A patent/IT1031361B/en active
- 1975-02-08 DE DE19752505328 patent/DE2505328C2/en not_active Expired
- 1975-02-11 FR FR7504176A patent/FR2260594B1/fr not_active Expired
- 1975-02-11 NL NL7501621A patent/NL178881C/en not_active IP Right Cessation
- 1975-02-12 JP JP1696975A patent/JPS5853012B2/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3741038A1 (en) * | 1986-12-04 | 1988-06-09 | Asahi Chemical Ind | METHOD FOR PRODUCING POLYPHENYLENE ETHERS |
| US4788277A (en) * | 1986-12-04 | 1988-11-29 | Asahi Kasei Kogyo Kabushiki Kaisha | Method for producing a polyphenylene ether |
| US8288501B2 (en) | 2008-04-18 | 2012-10-16 | Asahi Kasei Chemicals Corporation | Method for producing polyphenylene ether |
| US8357769B2 (en) | 2008-04-18 | 2013-01-22 | Asahi Kasei Chemicals Corporation | Method for producing polyphenylene ether |
| US8394913B2 (en) | 2008-04-18 | 2013-03-12 | Asahi Kasei Chemicals Corporation | Method for producing polyphenylene ether |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7501621A (en) | 1975-08-13 |
| JPS5853012B2 (en) | 1983-11-26 |
| AU7733275A (en) | 1976-07-15 |
| NL178881C (en) | 1986-06-02 |
| JPS50110498A (en) | 1975-08-30 |
| NL178881B (en) | 1986-01-02 |
| FR2260594B1 (en) | 1981-08-21 |
| IT1031361B (en) | 1979-04-30 |
| DE2505328A1 (en) | 1975-08-14 |
| FR2260594A1 (en) | 1975-09-05 |
| DE2505328C2 (en) | 1990-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19950128 |