JPS60137908A - 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
- JPS60137908A JPS60137908A JP24885283A JP24885283A JPS60137908A JP S60137908 A JPS60137908 A JP S60137908A JP 24885283 A JP24885283 A JP 24885283A JP 24885283 A JP24885283 A JP 24885283A JP S60137908 A JPS60137908 A JP S60137908A
- Authority
- JP
- Japan
- Prior art keywords
- methyl ether
- chloromethyl methyl
- reaction
- hydrogen chloride
- hydrochloric acid
- 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 43
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 59
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 claims abstract description 51
- 229940061627 chloromethyl methyl ether Drugs 0.000 claims abstract description 48
- 239000002245 particle Substances 0.000 claims abstract description 29
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000007265 chloromethylation reaction Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 7
- 239000011541 reaction mixture Substances 0.000 abstract description 7
- 238000000354 decomposition reaction Methods 0.000 abstract description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000012071 phase Substances 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 7
- -1 chloromethyl methyl Chemical group 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 206010042674 Swelling Diseases 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000002612 dispersion medium Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- 238000005576 amination reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003440 styrenes Chemical class 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
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-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
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 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
- 239000002253 acid Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 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
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 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
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 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
- 238000005406 washing Methods 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 |
|---|---|---|---|
| JP24885283A JPS60137908A (ja) | 1983-12-26 | 1983-12-26 | 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 |
|---|---|---|---|
| JP24885283A JPS60137908A (ja) | 1983-12-26 | 1983-12-26 | クロルメチル化ポリマ−の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60137908A true JPS60137908A (ja) | 1985-07-22 |
| JPS6261204B2 JPS6261204B2 (enrdf_load_stackoverflow) | 1987-12-21 |
Family
ID=17184379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24885283A Granted JPS60137908A (ja) | 1983-12-26 | 1983-12-26 | クロルメチル化ポリマ−の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60137908A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008144115A1 (en) * | 2007-05-23 | 2008-11-27 | Dow Global Technologies Inc. | Method for processing effluent from chloromethylation of vinyl aromatic polymers |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02246924A (ja) * | 1989-03-22 | 1990-10-02 | Morito Kk | 血圧測定用腕帯 |
| JPH09150066A (ja) | 1995-11-28 | 1997-06-10 | Mitsubishi Chem Corp | 陰イオン交換樹脂の製造法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1049270A (en) * | 1965-10-29 | 1966-11-23 | Wolfen Filmfab Veb | Recovery of monochlorodimethyl ether |
| GB1269986A (en) * | 1969-04-10 | 1972-04-12 | Mitsubishi Chem Ind | Porous cross-linked copolymer and ion-exchange resin |
| 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 |
-
1983
- 1983-12-26 JP JP24885283A patent/JPS60137908A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1049270A (en) * | 1965-10-29 | 1966-11-23 | Wolfen Filmfab Veb | Recovery of monochlorodimethyl ether |
| GB1269986A (en) * | 1969-04-10 | 1972-04-12 | Mitsubishi Chem Ind | Porous cross-linked copolymer and ion-exchange resin |
| 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 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008144115A1 (en) * | 2007-05-23 | 2008-11-27 | Dow Global Technologies Inc. | Method for processing effluent from chloromethylation of vinyl aromatic polymers |
| US8163138B2 (en) | 2007-05-23 | 2012-04-24 | Dow Global Technologies Llc | Method for processing effluent from chloromethylation of vinyl aromatic polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6261204B2 (enrdf_load_stackoverflow) | 1987-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Fréchet et al. | Poly (vinyl pyridine) s: Simple reactive polymers with multiple applications | |
| US4636554A (en) | Process for producing a chloromethylated polymer | |
| US3925264A (en) | Process for the production of anion exchangers | |
| US3995094A (en) | Halomethylation of polystyrene | |
| JPS6054327B2 (ja) | ポリフエニレンオキシドの製造方法 | |
| US4232125A (en) | Aminoalkylation of aromatic polymers using aldehyde, diacylamine and strong acid catalyst | |
| EP0000090B1 (en) | Modified phenolic resins, method for their preparation and their use as selective metal chelating agents | |
| US4321331A (en) | High density ion exchange resins from haloalkylated aromatic polymer | |
| US4225677A (en) | Process for the chloromethylation of polymers for the production of anionic exchange resins | |
| US3997706A (en) | Process for the chloromethylation of styrene-divinylbenzene copolymers | |
| WO1996019286A1 (en) | Methylene-bridged aromatic polymer adsorbents with increased hydrophobicity | |
| US3346516A (en) | Process for producing guanidine-substituted cross-linked poly (vinyl aromatic) anion exchange resins | |
| JPS60137908A (ja) | クロルメチル化ポリマ−の製造法 | |
| JPH0797406A (ja) | 弱塩基性アニオン交換体の製造法および同目的に適した試薬 | |
| JPS6226643B2 (enrdf_load_stackoverflow) | ||
| JPH06102691B2 (ja) | ビニル性芳香族重合体のクロロメチル化方法 | |
| JP3982166B2 (ja) | 陰イオン交換樹脂 | |
| KR900000516B1 (ko) | 고-용량, 산화안정성 폴리아민 이온교환수지 및 이의 제조방법 | |
| JPS5810404B2 (ja) | 官能性架橋共重合物の製法 | |
| JP3791709B2 (ja) | 耐酸化性アニオン交換樹脂および酸化性水溶液の精製方法 | |
| JPS6261205B2 (enrdf_load_stackoverflow) | ||
| JPH07188333A (ja) | クロロメチルメチルエーテルの回収方法 | |
| US3278462A (en) | Ion exchange resins from diphenyl ether polymeric derivatives, process for making same and use in removing alkylbenzene sulfonates | |
| JPH01143646A (ja) | ハロ芳香族変性の芳香族イオン交換樹脂 | |
| SU499272A1 (ru) | Способ получени низкоосновного анионита |