JPS60158201A - クロルメチル化ポリマ−の製造法 - Google Patents
クロルメチル化ポリマ−の製造法Info
- Publication number
- JPS60158201A JPS60158201A JP1467484A JP1467484A JPS60158201A JP S60158201 A JPS60158201 A JP S60158201A JP 1467484 A JP1467484 A JP 1467484A JP 1467484 A JP1467484 A JP 1467484A JP S60158201 A JPS60158201 A JP S60158201A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- reaction
- chloromethyl ether
- aqueous phase
- oil phase
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 41
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000002245 particle Substances 0.000 claims abstract description 26
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 229920001577 copolymer Polymers 0.000 claims abstract description 3
- 239000012071 phase Substances 0.000 claims description 25
- 239000008346 aqueous phase Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 11
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 4
- 239000011968 lewis acid catalyst Substances 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 33
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- 239000006227 byproduct Substances 0.000 abstract description 6
- 238000011084 recovery Methods 0.000 abstract description 4
- 239000006185 dispersion Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 25
- 238000007265 chloromethylation reaction Methods 0.000 description 18
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 206010042674 Swelling Diseases 0.000 description 5
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- 239000003957 anion exchange resin Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- -1 f-methylstyrene Chemical compound 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- ADLSFYJDHWUKFP-UHFFFAOYSA-N 5-methoxy-11,12-dihydroindolo[2,3-a]carbazole-6-carbonitrile Chemical compound N1C2=C3NC4=CC=C[CH]C4=C3C(OC)=C(C#N)C2=C2[C]1C=CC=C2 ADLSFYJDHWUKFP-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DHGJWSRGFMFRLS-UHFFFAOYSA-N hexa-1,3-dienylbenzene Chemical compound CCC=CC=CC1=CC=CC=C1 DHGJWSRGFMFRLS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1467484A JPS60158201A (ja) | 1984-01-30 | 1984-01-30 | クロルメチル化ポリマ−の製造法 |
| EP84114465A EP0150332A3 (en) | 1983-12-26 | 1984-11-29 | Process for producing a chloromethylated polymer |
| US06/681,102 US4636554A (en) | 1983-12-26 | 1984-12-13 | Process for producing a chloromethylated polymer |
| KR1019840008304A KR850004771A (ko) | 1983-12-26 | 1984-12-24 | 클로로메틸화 중합체의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1467484A JPS60158201A (ja) | 1984-01-30 | 1984-01-30 | クロルメチル化ポリマ−の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60158201A true JPS60158201A (ja) | 1985-08-19 |
| JPS6261205B2 JPS6261205B2 (enrdf_load_stackoverflow) | 1987-12-21 |
Family
ID=11867763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1467484A Granted JPS60158201A (ja) | 1983-12-26 | 1984-01-30 | クロルメチル化ポリマ−の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60158201A (enrdf_load_stackoverflow) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1269986A (en) * | 1969-04-10 | 1972-04-12 | Mitsubishi Chem Ind | Porous cross-linked copolymer and ion-exchange resin |
| JPS5361320A (en) * | 1976-11-12 | 1978-06-01 | Hitachi Maxell | Method of making magnetic disc cartridge |
| JPS57191986U (enrdf_load_stackoverflow) * | 1981-05-05 | 1982-12-06 | ||
| US4393145A (en) * | 1979-05-01 | 1983-07-12 | Etablissement Texcontor | Anionic ion exchange resins with cholesterol-decreasing properties |
| JPS58203927A (ja) * | 1982-05-24 | 1983-11-28 | Mitsubishi Chem Ind Ltd | クロロメチルアルキルエ−テルの製造法 |
| JPS6020077U (ja) * | 1983-07-18 | 1985-02-12 | 株式会社 麗光 | 磁気デイスク収納ジヤケツト |
| JPS6089881A (ja) * | 1983-10-21 | 1985-05-20 | Fuji Photo Film Co Ltd | フレキシブルデイスクジヤケツト |
| JPS60106083A (ja) * | 1983-11-11 | 1985-06-11 | Fuji Photo Film Co Ltd | フレキシブルデイスクジヤケツト |
-
1984
- 1984-01-30 JP JP1467484A patent/JPS60158201A/ja active Granted
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1269986A (en) * | 1969-04-10 | 1972-04-12 | Mitsubishi Chem Ind | Porous cross-linked copolymer and ion-exchange resin |
| JPS5361320A (en) * | 1976-11-12 | 1978-06-01 | Hitachi Maxell | Method of making magnetic disc cartridge |
| US4393145A (en) * | 1979-05-01 | 1983-07-12 | Etablissement Texcontor | Anionic ion exchange resins with cholesterol-decreasing properties |
| JPS57191986U (enrdf_load_stackoverflow) * | 1981-05-05 | 1982-12-06 | ||
| JPS58203927A (ja) * | 1982-05-24 | 1983-11-28 | Mitsubishi Chem Ind Ltd | クロロメチルアルキルエ−テルの製造法 |
| JPS6020077U (ja) * | 1983-07-18 | 1985-02-12 | 株式会社 麗光 | 磁気デイスク収納ジヤケツト |
| JPS6089881A (ja) * | 1983-10-21 | 1985-05-20 | Fuji Photo Film Co Ltd | フレキシブルデイスクジヤケツト |
| JPS60106083A (ja) * | 1983-11-11 | 1985-06-11 | Fuji Photo Film Co Ltd | フレキシブルデイスクジヤケツト |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6261205B2 (enrdf_load_stackoverflow) | 1987-12-21 |
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