JP5357780B2 - 安定性及び重合性の改善されたn−メチル−n−ビニルアセトアミドの製造方法 - Google Patents
安定性及び重合性の改善されたn−メチル−n−ビニルアセトアミドの製造方法 Download PDFInfo
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- JP5357780B2 JP5357780B2 JP2009548034A JP2009548034A JP5357780B2 JP 5357780 B2 JP5357780 B2 JP 5357780B2 JP 2009548034 A JP2009548034 A JP 2009548034A JP 2009548034 A JP2009548034 A JP 2009548034A JP 5357780 B2 JP5357780 B2 JP 5357780B2
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- Prior art keywords
- methyl
- vinylacetamide
- methylacetamide
- butadienyl
- producing
- Prior art date
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- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 title claims abstract description 187
- 238000000034 method Methods 0.000 title claims abstract description 79
- 230000008569 process Effects 0.000 title claims description 6
- WLTKFGTTWSWWJQ-UHFFFAOYSA-N n-buta-1,3-dienyl-n-methylacetamide Chemical compound CC(=O)N(C)C=CC=C WLTKFGTTWSWWJQ-UHFFFAOYSA-N 0.000 claims abstract description 77
- 238000004519 manufacturing process Methods 0.000 claims abstract description 51
- 239000000178 monomer Substances 0.000 claims abstract description 25
- -1 1,3-butadienyl group Chemical group 0.000 claims description 61
- 238000006116 polymerization reaction Methods 0.000 claims description 38
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 19
- 238000004821 distillation Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
- 239000003463 adsorbent Substances 0.000 claims description 14
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 12
- 238000001179 sorption measurement Methods 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 230000006641 stabilisation Effects 0.000 claims description 5
- 238000011105 stabilization Methods 0.000 claims description 5
- 230000001035 methylating effect Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 14
- 230000000704 physical effect Effects 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- 239000002994 raw material Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 239000002243 precursor Substances 0.000 description 14
- 230000001276 controlling effect Effects 0.000 description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- YOVPOCLZLPJOPC-UHFFFAOYSA-N CNC(=O)CC=CC=C Chemical compound CNC(=O)CC=CC=C YOVPOCLZLPJOPC-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000012620 biological material Substances 0.000 description 3
- 238000003421 catalytic decomposition reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000005553 drilling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000008394 flocculating agent Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- GUZBASSCVSKFHN-UHFFFAOYSA-N n,n',3-trimethylpentanediamide Chemical compound CNC(=O)CC(C)CC(=O)NC GUZBASSCVSKFHN-UHFFFAOYSA-N 0.000 description 3
- SJSZBOAQWPKFMU-UHFFFAOYSA-N n-(1-acetamidoethyl)acetamide Chemical compound CC(=O)NC(C)NC(C)=O SJSZBOAQWPKFMU-UHFFFAOYSA-N 0.000 description 3
- MGDNHIJGIWHQBL-UHFFFAOYSA-N n-ethyl-n-methylacetamide Chemical compound CCN(C)C(C)=O MGDNHIJGIWHQBL-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005401 siloxanyl group Chemical group 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CRXJTSOQBIDSCO-UHFFFAOYSA-N S(=O)(=O)(O)C(C(=O)N)CC.[K] Chemical group S(=O)(=O)(O)C(C(=O)N)CC.[K] CRXJTSOQBIDSCO-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000003827 glycol group Chemical group 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000003879 lubricant additive Substances 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
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- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VTWDKFNVVLAELH-UHFFFAOYSA-N methyl-p-benzoquinone Natural products CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- VSEKEMQDOIJVFY-UHFFFAOYSA-N n',n'-dimethylmethanediamine Chemical compound CN(C)CN VSEKEMQDOIJVFY-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- JHVBXBBQUFXFTM-UHFFFAOYSA-N n-(1,3-dimethoxybutyl)-n-methylacetamide Chemical compound COC(C)CC(OC)N(C)C(C)=O JHVBXBBQUFXFTM-UHFFFAOYSA-N 0.000 description 1
- ISIHNWKJZISSBD-UHFFFAOYSA-N n-(1-ethoxyethyl)-n-methylacetamide Chemical compound CCOC(C)N(C)C(C)=O ISIHNWKJZISSBD-UHFFFAOYSA-N 0.000 description 1
- RYGPJMDKDKHOTB-UHFFFAOYSA-N n-(1-methoxyethyl)acetamide Chemical compound COC(C)NC(C)=O RYGPJMDKDKHOTB-UHFFFAOYSA-N 0.000 description 1
- KEZPMZSDLBJCHH-UHFFFAOYSA-N n-(4-anilinophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 KEZPMZSDLBJCHH-UHFFFAOYSA-N 0.000 description 1
- RVQALLPERNMRKF-UHFFFAOYSA-N n-[1,3-di(propan-2-yloxy)butyl]-n-methylacetamide Chemical compound CC(C)OC(C)CC(OC(C)C)N(C)C(C)=O RVQALLPERNMRKF-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-AZXPZELESA-N n-methylacetamide Chemical group C[15NH]C(C)=O OHLUUHNLEMFGTQ-AZXPZELESA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- XVUQUHHNZAHWHM-UHFFFAOYSA-N potassium;2-sulfoethylazanide Chemical group [K+].[NH-]CCS(O)(=O)=O XVUQUHHNZAHWHM-UHFFFAOYSA-N 0.000 description 1
- ZMJJCODMIXQWCQ-UHFFFAOYSA-N potassium;di(propan-2-yl)azanide Chemical compound [K+].CC(C)[N-]C(C)C ZMJJCODMIXQWCQ-UHFFFAOYSA-N 0.000 description 1
- PAIDBDYPWGSQQE-UHFFFAOYSA-N potassium;sulfomethylazanide Chemical group [K+].[NH-]CS(O)(=O)=O PAIDBDYPWGSQQE-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- NPSSWQJHYLDCNV-UHFFFAOYSA-N prop-2-enoic acid;hydrochloride Chemical compound Cl.OC(=O)C=C NPSSWQJHYLDCNV-UHFFFAOYSA-N 0.000 description 1
- YOSXAXYCARLZTR-UHFFFAOYSA-N prop-2-enoyl isocyanate Chemical compound C=CC(=O)N=C=O YOSXAXYCARLZTR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MJWOUYWACLELBP-UHFFFAOYSA-N sodium;2-sulfoethylazanide Chemical group [Na+].[NH-]CCS(O)(=O)=O MJWOUYWACLELBP-UHFFFAOYSA-N 0.000 description 1
- OLYREVXWRZVUTJ-UHFFFAOYSA-N sodium;sulfomethylazanide Chemical group [Na+].[NH-]CS(O)(=O)=O OLYREVXWRZVUTJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical group NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F126/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F126/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Description
また、本発明の他の課題は、前記方法により得られたN−メチル−N−ビニルアセトアミドを単独重合または他のモノマーと共重合する、安定した品質のN−メチル−N−ビニルアセトアミド系ポリマーの製造方法を提供することにある。
2.N−メチル−N−ビニルアセトアミド中のN−1,3−ブタジエニル−N−メチルアセトアミドの含有量を0.01〜150ppmにコントロールする工程を有することを特徴とする安定性及び/または重合性の改善されたN−メチル−N−ビニルアセトアミドの製造方法。
3.前記N−メチル−N−ビニルアセトアミドがN−ビニルアセトアミドをメチル化して得られるものである前記1または2に記載のN−メチル−N−ビニルアセトアミドの製造方法。
4.前記N−メチル−N−ビニルアセトアミドがN−メチル−N−(1−アルコキシエチル)アセトアミドを熱分解して得られるものである前記1または2に記載のN−メチル−N−ビニルアセトアミドの製造方法。
5.前記N−メチル−N−ビニルアセトアミド中のN−1,3−ブタジエニル−N−メチルアセトアミド含有量のコントロール方法が、N−メチル−N−ビニルアセトアミドまたはその溶液の精密蒸留法、活性炭吸着剤での物理的吸着法、ディールス・アルダー反応法または1,3−ブタジエニル基の選択水素化反応法による処理である前記1〜4のいずれかに記載のN−メチル−N−ビニルアセトアミドの製造方法。
6.N−ビニルアセトアミドを、ハロゲン化メチルを用いてメチル化する前記3に記載のN−メチル−N−ビニルアセトアミドの製造方法。
7.前記N−メチル−N−ビニルアセトアミドのメチル化反応において、テトラヒドロフランを溶媒として使用する前記3または6に記載のN−メチル−N−ビニルアセトアミドの製造方法。
8.N−1,3−ブタジエニル−N−メチルアセトアミドの含有量を0.05〜100ppmにコントロールする前記1または2に記載のN−メチル−N−ビニルアセトアミドの製造方法。
9.N−1,3−ブタジエニル−N−メチルアセトアミドの含有量を0.1〜30ppmにコントロールする前記8に記載のN−メチル−N−ビニルアセトアミドの製造方法。
10.前記1〜9のいずれかに記載の製造方法により製造されたN−メチル−N−ビニルアセトアミドを重合することを特徴とするN−メチル−N−ビニルアセトアミドホモポリマーの製造方法。
11.前記1〜9のいずれかに記載の製造方法により製造されたN−メチル−N−ビニルアセトアミドと他の共重合可能なモノマーとを共重合することを特徴とするN−メチル−N−ビニルアセトアミドコポリマーの製造方法。
12.前記10の製造方法により製造されたコンタクトレンズ用N−メチル−N−ビニルアセトアミドホモポリマー。
13.前記11の製造方法により製造されたコンタクトレンズ用N−メチル−N−ビニルアセトアミドコポリマー。
14.N−メチル−N−ビニルアセトアミドの重合禁止作用を有するN−1,3−ブタジエニル−N−メチルアセトアミドを0.01〜150ppm含有する安定性及び/または重合性の改善されたN−メチル−N−ビニルアセトアミド。
15.N−メチル−N−ビニルアセトアミド中のN−1,3−ブタジエニル−N−メチルアセトアミドの含有量を0.01〜150ppmにコントロールすることを特徴とするN−メチル−N−ビニルアセトアミドの安定化方法。
16.N−1,3−ブタジエニル−N−メチルアセトアミドからなるN−メチル−N−ビニルアセトアミドの重合禁止剤。
17.N−1,3−ブタジエニル−N−メチルアセトアミドからなるN−メチル−N−ビニルアセトアミドの安定性及び/または重合性改善剤。
また、本発明の方法により得られたN−メチル−N−ビニルアセトアミドを用いることにより、品質の安定したN−メチル−N−ビニルアセトアミド系ポリマーを製造することができる。
本発明で用いるN−メチル−N−ビニルアセトアミドは、次式(I)
本発明で用いるN−1,3−ブタジエニル−N−メチルアセトアミドは、次式(II)
ヒドロキシエチル(メタ)アクリレート、ヒドロキシブチル(メタ)アクリレートなどの水酸基含有アクリレートあるいは水酸基含有メタクリレートと種々のジイソシアネート化合物と反応させて得られるアクリレート基あるいはメタクリレート基含有イソシアナート化合物、
カラム:SHODEX 5SIL−4B、
溶離液:n-ヘキサン/イソプロピルアルコール=9/1、
流 速:1mL/min、
検出器:紫外光検出器254nm。
温度計及びドライアイス−エタノールトラップを具備した三つ口フラスコ(200mL)に、N−メチルアセトアミド7.31g(0.1mol)、メタノール21.47g(0.67mol)、エチリデンビス(N−メチルアセトアミド)2.16g(15mmol)、アセトアルデヒドジメチルアセタール9.01g(0.1mol)を加え、45〜48℃で均一になるまで撹拌、溶解した。濃硫酸0.04g(上記仕込み量に対して0.1質量%)をイソプロピルアルコール1.06g(33mmol)に溶解(以下の実施例も同様)した液を加え撹拌後、アセトアルデヒド17.62g(0.4mol)を滴下ロ−トで3分かけて加えた。滴下終了後、50℃で3時間反応を行い、触媒を中和した後、ガスクロマトグラフィーで定量したところ、N−メチルアセトアミド転化率は86%、N−(1−メトキシエチル)−N−メチルアセトアミドの選択率は93%であり、副生物のエチリデンビス(N−メチルアセトアミド)の選択率は5.2%であった。得られた反応液から、減圧蒸留でN−(1−メトキシエチル)−N−メチルアセトアミドを得、450℃、滞留時間1秒で、N−メチル−N−ビニルアセトアミドとメタノールに熱分解した。分解液を20℃に冷却し、20mmHg、65℃で蒸留した。純度99.8%、N−1,3−ブタジエニル−N−メチルアセトアミド含有量810ppmのN−メチル−N−ビニルアセトアミドが得られた。
上記製造例1で得られたN−メチル−N−ビニルアセトアミドの重合性を評価するため、蒸留水25gにN−メチル−N−ビニルアセトアミド25gを加えて、窒素置換後、2,2’−アゾビス(2−アミジノプロパン)2塩酸塩(V−50;和光純薬工業(株)製商品名)を20.0mg加え、70℃の恒温水槽に浸した。30分後、ハイドロキノン1%水溶液を150g添加し希釈した液の粘度を、BL型粘度計を用いて、20℃、回転数30rpmで測定したところ、10mPa・s以下であった。
製造例1で得られた熱分解液を、以下の条件にて蒸留した。20mm×500mmの蒸留塔にガラスビーズを詰め、還流比0.3で処理した(指定蒸留段数:10段程度)。主留は63℃(21mmHg)で初留から50mLずつフラクション1からフラクション7まで、及び釜残に分別した。次に、上記フラクション2及び3を混合し、単蒸留し、純度97.5%、N−1,3−ブタジエニル−N−メチルアセトアミド含有量146ppmのN−メチル−N−ビニルアセトアミドが得られた。製造例1と同様に重合性評価試験を行ったところ、粘度は130mPa・sであった。
昭和電工(株)製のN−ビニルアセトアミド150gとTHF2680gの混合液に、t−ブトキシカリウム245gを添加した(t−ブトキシカリウム/N−ビニルアセトアミド=1.2(モル比))。次いで、ヨウ化メチル302g(99.5%)を加え撹拌した(ヨウ化メチル/N−ビニルアセトアミド=1.2(モル比))。スラリー状態となった混合液をろ紙(5C)にてろ過し、ろ液をエバポレーターにて濃縮した(40℃)。次に、20mmHg、65℃で蒸留し、純度98%のN−メチル−N−ビニルアセトアミドを得た(総収率69%)。なお、得られたN−メチル−N−ビニルアセトアミドは無色透明の液体で、N−1,3−ブタジエニル−N−メチルアセトアミドの濃度は30ppmであった。製造例1と同様に重合性評価試験を行ったところ、粘度は160mPa・sであった。
酢酸ビニル(1mol)とN−メチルアセトアミド(1mol)の混合液に、4−ジメチルアミノピリジンを触媒として加え、60℃で反応させた。次に、12mmHg、85℃で蒸留し、純度96%のN−メチル−N−ビニルアセトアミドを得た(総収率72%)。なお、得られたN−メチル−N−ビニルアセトアミドは、薄い茶色に着色した液体で、N−1,3−ブタジエニル−N−メチルアセトアミドの濃度は760ppmであった。実施例1と同様に重合性評価試験を行ったところ、粘度は10mPa・s以下であった。
アルミナ担体にパラジウムを0.5質量%担持させた固体触媒5g、及びN−1,3−ブタジエニル−N−メチルアセトアミドを810ppm、N−メチル−N−ビニルアセトアミド55質量%、N−メチル−N−(1−メトキシエチル)アセトアミド15質量%、N−メチルアセトアミド7質量%、メタノール20質量%を含む混合液50gを、200mLフラスコに入れ、水素雰囲気下、常温で30分間撹拌して反応を行った。反応終了後、反応液から触媒をろ別し、ろ液を分析した。N−1,3−ブタジエニル−N−メチルアセトアミドは島津製作所(株)製高速液体カラムクロマトグラフィーで、その他の成分は以下の条件で、島津製作所(株)製ガスクロマトグラフィーGC−17Aにより分析した。
カラム :DB−WAX ID 0.25mm、Film 0.25μm
Length 30m、
流量 :0.9ml/min、
スピリット比:60、
カラム温度 :40℃、7分保持→25℃/分で150℃へ昇温後15分保持→
25℃/分で220℃へ昇温後22分保持、
インジェクション温度:200℃、
検出器 :FID、
検出温度 :220℃。
また、本発明によれば、前記方法により得られたN−メチル−N−ビニルアセトアミドを単独重合または他のモノマーと共重合することにより、品質の安定したN−メチル−N−ビニルアセトアミド系ポリマーを得ることができる。
Claims (13)
- N−メチル−N−ビニルアセトアミド中のN−1,3−ブタジエニル−N−メチルアセトアミドの含有量を0.01〜150ppmにコントロールする工程を有することを特徴とするN−メチル−N−ビニルアセトアミドの製造方法。
- N−メチル−N−ビニルアセトアミド中のN−1,3−ブタジエニル−N−メチルアセトアミドの含有量を0.01〜150ppmにコントロールする工程を有することを特徴とする安定性及び/または重合性の改善されたN−メチル−N−ビニルアセトアミドの製造方法。
- 前記N−メチル−N−ビニルアセトアミドがN−ビニルアセトアミドをメチル化して得られるものである請求項1または2に記載のN−メチル−N−ビニルアセトアミドの製造方法。
- 前記N−メチル−N−ビニルアセトアミドがN−メチル−N−(1−アルコキシエチル)アセトアミドを熱分解して得られるものである請求項1または2に記載のN−メチル−N−ビニルアセトアミドの製造方法。
- 前記N−メチル−N−ビニルアセトアミド中のN−1,3−ブタジエニル−N−メチルアセトアミド含有量のコントロール方法が、N−メチル−N−ビニルアセトアミドまたはその溶液の精密蒸留法、活性炭吸着剤での物理的吸着法、ディールス・アルダー反応法または1,3−ブタジエニル基の選択水素化反応法による処理である請求項1〜4のいずれかに記載のN−メチル−N−ビニルアセトアミドの製造方法。
- N−ビニルアセトアミドを、ハロゲン化メチルを用いてメチル化する請求項3に記載のN−メチル−N−ビニルアセトアミドの製造方法。
- 前記N−メチル−N−ビニルアセトアミドのメチル化反応において、テトラヒドロフランを溶媒として使用する請求項3または6に記載のN−メチル−N−ビニルアセトアミドの製造方法。
- 請求項1〜7のいずれかに記載の製造方法により製造されたN−メチル−N−ビニルアセトアミドを重合することを特徴とするN−メチル−N−ビニルアセトアミドホモポリマーの製造方法。
- 請求項1〜7のいずれかに記載の製造方法により製造されたN−メチル−N−ビニルアセトアミドと他の共重合可能なモノマーとを共重合することを特徴とするN−メチル−N−ビニルアセトアミドコポリマーの製造方法。
- N−メチル−N−ビニルアセトアミドの重合禁止作用を有するN−1,3−ブタジエニル−N−メチルアセトアミドを0.01〜150ppm含有する安定性及び/または重合性の改善されたN−メチル−N−ビニルアセトアミド。
- N−メチル−N−ビニルアセトアミド中のN−1,3−ブタジエニル−N−メチルアセトアミドの含有量を0.01〜150ppmにコントロールすることを特徴とするN−メチル−N−ビニルアセトアミドの安定化方法。
- N−1,3−ブタジエニル−N−メチルアセトアミドからなるN−メチル−N−ビニルアセトアミドの重合禁止剤。
- N−1,3−ブタジエニル−N−メチルアセトアミドからなるN−メチル−N−ビニルアセトアミドの安定性及び/または重合性改善剤。
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