CN107428665A - (甲基)丙烯酸酯的制造方法 - Google Patents
(甲基)丙烯酸酯的制造方法 Download PDFInfo
- Publication number
- CN107428665A CN107428665A CN201680021017.2A CN201680021017A CN107428665A CN 107428665 A CN107428665 A CN 107428665A CN 201680021017 A CN201680021017 A CN 201680021017A CN 107428665 A CN107428665 A CN 107428665A
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- Prior art keywords
- methyl
- acrylate
- catalyst
- manufacture method
- compound
- Prior art date
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 title claims abstract description 70
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 57
- -1 cyclic tertiary amine Chemical class 0.000 claims abstract description 99
- 239000003054 catalyst Substances 0.000 claims abstract description 97
- 238000006243 chemical reaction Methods 0.000 claims abstract description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 76
- 150000002148 esters Chemical group 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000003463 adsorbent Substances 0.000 claims abstract description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 22
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 21
- 125000004427 diamine group Chemical group 0.000 claims abstract description 9
- 150000001409 amidines Chemical class 0.000 claims abstract description 8
- 239000011777 magnesium Substances 0.000 claims abstract description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 6
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 6
- 239000010703 silicon Substances 0.000 claims abstract description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004411 aluminium Substances 0.000 claims abstract description 5
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 89
- 239000002585 base Substances 0.000 claims description 52
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 29
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 18
- 235000011187 glycerol Nutrition 0.000 claims description 16
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000012545 processing Methods 0.000 claims description 13
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 10
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 9
- 150000003752 zinc compounds Chemical class 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 6
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 6
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000811 xylitol Substances 0.000 claims description 4
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 4
- 235000010447 xylitol Nutrition 0.000 claims description 4
- 229960002675 xylitol Drugs 0.000 claims description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical class CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 3
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims 2
- 150000004985 diamines Chemical class 0.000 claims 1
- 125000003410 quininyl group Chemical group 0.000 claims 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 89
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 53
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 20
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 20
- 239000011701 zinc Substances 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 18
- 229910052725 zinc Inorganic materials 0.000 description 18
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 238000007792 addition Methods 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- 239000012973 diazabicyclooctane Substances 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 150000003003 phosphines Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 229930185605 Bisphenol Natural products 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 230000005587 bubbling Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229960002442 glucosamine Drugs 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 238000011085 pressure filtration Methods 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- 238000007670 refining Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004246 zinc acetate Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000006267 biphenyl group Chemical group 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229940035423 ethyl ether Drugs 0.000 description 5
- 239000000391 magnesium silicate Substances 0.000 description 5
- 229910052919 magnesium silicate Inorganic materials 0.000 description 5
- 235000019792 magnesium silicate Nutrition 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical class CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007767 bonding agent Substances 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 4
- 238000011403 purification operation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 4
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 4
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 3
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 3
- IEMDOFXTVAPVLX-YWQHLDGFSA-N Leucomycin A1 Chemical compound CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 IEMDOFXTVAPVLX-YWQHLDGFSA-N 0.000 description 3
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000005594 diketone group Chemical group 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002085 enols Chemical class 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 3
- 229960002479 isosorbide Drugs 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
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- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
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Abstract
根据本发明,提供一种(甲基)丙烯酸酯的制造方法,其特征在于,包括以下工序:在并用下述催化剂A和下述催化剂B而使醇与单官能(甲基)丙烯酸酯发生酯交换反应来制造(甲基)丙烯酸酯时,对酯交换反应的反应产物进行与下述吸附剂C的接触处理。催化剂A:选自具有氮杂双环结构的环状叔胺或其盐或其配合物、脒或其盐或其配合物、具有吡啶环的化合物或其盐或其配合物、膦或其盐或其配合物、具有叔二胺结构的化合物或其盐或其配合物中的一种以上化合物。催化剂B:选自含锌化合物中的一种以上化合物。吸附剂C:选自含有镁、铝、硅的至少一种的氧化物和氢氧化物中的一种以上化合物。
Description
技术领域
本发明涉及(甲基)丙烯酸酯的制造方法。详细地说,本发明涉及一种(甲基)丙烯酸酯的制造方法,其特征在于,使醇与单官能(甲基)丙烯酸酯发生酯交换反应,得到(甲基)丙烯酸酯。特别涉及反应中使用的催化剂的除去方法。
背景技术
(甲基)丙烯酸酯通过照射紫外线、电子射线等活性能量射线、或加热而固化,因此,作为涂料、油墨、粘接剂、光学透镜、填充剂和成型材料等的配合物的交联成分、或作为反应性稀释剂成分而大量使用。
特别是对于具有3个以上(甲基)丙烯酰基的多官能(甲基)丙烯酸酯,其固化物显现出高的硬度和优异的耐磨性,作为硬涂剂涂料的配合成分而大量使用。
作为该多官能(甲基)丙烯酸酯,已知有三羟甲基丙烷三(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、双三羟甲基丙烷四(甲基)丙烯酸酯、二季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、三季戊四醇八(甲基)丙烯酸酯等。
这些(甲基)丙烯酸酯通过以相应的醇和(甲基)丙烯酸为原料,以磺酸(参照专利文献1)为催化剂的酯化反应,或者以相应的醇和单官能(甲基)丙烯酸酯为原料、以有机锡化合物(参照专利文献2)为催化剂的酯交换反应来制造。另外,关于酯交换反应,已知有并用有机磷化合物和锌化合物等作为催化剂的方法(参照专利文献3)。
这些(甲基)丙烯酸酯的制造中使用的催化剂通过反应后的精制操作而除去。但是,当催化剂的除去不充分时,有时,得到的(甲基)丙烯酸酯的贮存稳定性和热稳定性不良,在保管中发生聚合反应或水解反应,产生聚合物、(甲基)丙烯酸等酸成分。
含有聚合物的(甲基)丙烯酸酯由于发生固化不均匀或浑浊,无法适用于重视均匀性和透光性的光学透镜用途等。另外,产生酸成分的(甲基)丙烯酸酯除了臭气和装置腐蚀的问题以外,耐水性变差,因而在用于涂料和粘接剂用途的情况下,有时固化物吸收水分,引起涂面的剥离和粘接强度的下降。另外,(甲基)丙烯酸酯有时暴露于配合时用于均匀化的加热搅拌处理、以及固化后的耐热试验。但是,热稳定性不良的(甲基)丙烯酸酯除了产生上述的聚合物和/或酸成分以外,还发生着色,因而到底无法用于要求透明性的光学透镜用途等。
在专利文献1中,公开了对以磺酸为催化剂的酯化反应后的反应液
实施中和处理和水洗处理,再添加季铵盐或季盐而进行加热处理的方法,但操作略复杂。另外,在专利文献2中,公开了在以有机锡化合物为催化剂的酯交换反应结束后添加溶剂等,进行析出过滤的方法,但效果不充分,予以说明,精制物中含有数百ppm的锡。
现有技术文献
专利文献
专利文献1:专利第4811109号公报
专利文献2:特开2006-16322号公报
专利文献3:专利第4656351号公报
发明内容
发明要解决的课题
本发明正是鉴于上述现状而完成的,其目的在于,以简便的操作除去(甲基)丙烯酸酯的制造中使用的催化剂,从而得到催化剂被充分除去的高品质的(甲基)丙烯酸酯。
解决课题的手段
本发明人等为了解决上述课题进行了深入的研究。结果发现,在并用下述催化剂A和下述催化剂B而使醇与单官能(甲基)丙烯酸酯发生酯交换反应来制造(甲基)丙烯酸酯时,通过对酯交换反应的反应产物进行与下述吸附剂C的接触处理,能够得到催化剂被充分除去的高品质的(甲基)丙烯酸酯,至此完成了本发明。
催化剂A:选自具有氮杂双环结构的环状叔胺或其盐或其配合物、脒或其盐或其配合物、具有吡啶环的化合物或其盐或其配合物、膦或其盐或其配合物、具有叔二胺结构的化合物或其盐或其配合物中的一种以上化合物。
催化剂B:选自含锌化合物中的一种以上化合物。
吸附剂C:选自含有镁、铝、硅的至少一种的氧化物和氢氧化物中的一种以上化合物。
发明效果
根据本发明的制造方法,可得到高品质的(甲基)丙烯酸酯。由本发明制造方法得到的(甲基)丙烯酸酯可以作为涂料、油墨、粘接剂、光学透镜、填充剂和成型材料等的配合物的交联成分、或作为反应性稀释剂成分而适用于各种工业用途。
附图说明
[图1]是显示本发明中的(甲基)丙烯酸酯的制造方法的反应机制的概略图。
具体实施方式
本发明如下所述:在并用下述催化剂A和下述催化剂B而使醇与单官能(甲基)丙烯酸酯发生酯交换反应来制造(甲基)丙烯酸酯时,通过对酯交换反应的反应产物进行与下述吸附剂C的接触处理,由此,得到了催化剂被充分除去了的高品质的(甲基)丙烯酸酯。
催化剂A:选自具有氮杂双环结构的环状叔胺或其盐或其配合物、脒或其盐或其配合物、具有吡啶环的化合物或其盐或其配合物、膦或其盐或其配合物、具有叔二胺结构的化合物或其盐或其配合物中的一种以上化合物。
催化剂B:选自含锌化合物中的一种以上化合物。
吸附剂C:选自含有镁、铝、硅的至少一种的氧化物和氢氧化物中的一种以上化合物。
予以说明,本发明中的“(甲基)丙烯酸酯”是指包含在本发明得到的反应产物中的目标的(甲基)丙烯酸酯。得到的(甲基)丙烯酸酯根据所使用的醇的羟基数,为单官能、2官能或多官能。本发明中的“单官能(甲基)丙烯酸酯”是指用作原料的(甲基)丙烯酸酯。
以下,详细说明本发明。
本发明中作为原料使用的醇是分子中具有至少1个以上醇性羟基的脂族醇、脂环式醇、芳族醇、多元醇醚等。该醇可在分子内具有其他官能团或键,例如酚性羟基、酮基、酰基、醛基、硫醇基、氨基、亚氨基、氰基、硝基、醚键、酯键、碳酸酯键、酰胺键、酰亚胺键、肽键、尿烷键、缩醛键、半缩醛键、半缩酮键等。
作为具有1个醇性羟基的一元醇的具体例,可举出乙二醇单甲基醚、二甘醇单甲基醚、二甘醇单乙基醚、三甘醇单甲基醚、四甘醇单甲基醚、聚乙二醇单甲基醚、二丙二醇单甲基醚、三丙二醇单丁基醚、聚丙二醇单乙基醚、1,6-己二醇单甲基醚、1,6-己二醇单乙基醚、四亚甲基二醇单甲基醚、四亚甲基二醇单乙基醚、聚四亚甲基二醇单甲基醚、聚四亚甲基二醇单乙基醚、缩水甘油、2-(2-氯乙氧基)乙醇、2-(2-二甲氨基乙氧基)乙醇、2-乙基己基醇的环氧烷改性物等分子内具有醚键的一元醇;2-羟乙基乙烯基醚(别名:乙二醇单乙烯基醚)、3-羟丙基乙烯基醚、2-羟丙基乙烯基醚、2-羟基异丙基乙烯基醚、4-羟基丁基乙烯基醚、3-羟基丁基乙烯基醚、2-羟基丁基乙烯基醚、3-羟基异丁基乙烯基醚、2-羟基异丁基乙烯基醚、1-甲基-3-羟丙基乙烯基醚、1-甲基-2-羟丙基乙烯基醚、1-羟甲基丙基乙烯基醚、4-羟基环己基乙烯基醚、1,6-己二醇单乙烯基醚、四亚甲基二醇单乙烯基醚、聚四亚甲基二醇单乙烯基醚、1,4-环己烷二甲醇单乙烯基醚、1,3-环己烷二甲醇单乙烯基醚、1,2-环己烷二甲醇单乙烯基醚、异山梨醇单乙烯基醚、p-二甲苯二醇单乙烯基醚、m-二甲苯二醇单乙烯基醚、o-二甲苯二醇单乙烯基醚、二甘醇单乙烯基醚、三甘醇单乙烯基醚、四甘醇单乙烯基醚、五甘醇单乙烯基醚、低聚乙二醇单乙烯基醚、聚乙二醇单乙烯基醚、二丙二醇单乙烯基醚、三丙二醇单乙烯基醚、四丙二醇单乙烯基醚、五丙二醇单乙烯基醚、低聚丙二醇单乙烯基醚、聚丙二醇单乙烯基醚、乙二醇-丙二醇共聚物单乙烯基醚等分子内具有乙烯基和醚键的一元醇;三环[5.2.1.02,6]癸烯醇(别名:羟基二环戊二烯)、三环[5.2.1.02,6]癸醇、三环[5.2.1.02,6]癸烯氧基乙醇、三环[5.2.1.02,6]癸氧基乙醇、三环[5.2.1.02,6]癸烯氧基丙醇、三环[5.2.1.02,6]癸氧基丙醇、三环[5.2.1.02,6]癸烯氧基乙氧基乙醇、三环[5.2.1.02 ,6]癸氧基乙氧基乙醇、4-羟基-2,2,6,6-四甲基哌啶、4-羟基-1,2,2,6,6-五甲基哌啶、氧杂环丁烷基甲醇、四氢糠醇、四氢吡喃醇、1,4-环己烷二甲醇单甲基醚、1,3-环己烷二甲醇单甲基醚、1,2-环己烷二甲醇单甲基醚、异山梨醇单甲基醚、异山梨醇单乙基醚、2,3-O-sec-亚丁基甘油、5-乙基-5-(羟甲基)-1,3-二烷、α-羟基-γ-丁内酯、1,2-碳酸甘油酯、1,3-二氧戊环-4-基甲醇、2,2-二甲基-1,3-二氧戊环-4-甲醇、β-羟基-γ-丁内酯、α-羟甲基-γ-丁内酯、β-羟甲基-γ-丁内酯等具有环结构的一元醇;苄醇、苯氧基乙醇、苯氧基丙醇、p-二甲苯二醇单甲基醚、m-二甲苯二醇单甲基醚、o-二甲苯二醇单甲基醚、苯酚的环氧烷改性物、邻苯基苯酚的环氧烷改性物、对枯基苯酚的环氧烷改性物、壬基酚的环氧烷改性物等具有芳环的醇等。
作为具有2个醇性羟基的二元醇的具体例,可举出乙二醇、二甘醇、三甘醇、聚乙二醇、丙二醇、三亚甲基二醇、二丙二醇、三丙二醇、聚丙二醇、丁二醇、戊二醇、己二醇、庚二醇、壬二醇、新戊二醇、环己二醇、环己烷二甲醇、二烷二醇、N-甲基二乙醇胺、N-乙基二乙醇胺、N-丁基二乙醇胺、N-叔丁基二乙醇胺、N-月桂基二乙醇胺、硬脂基二乙醇胺、N-苯基二乙醇胺、间甲苯基二乙醇胺、对甲苯基二乙醇胺、N,N'-双(2-羟丙基)苯胺、N-亚硝基二乙醇胺、N-(2-羟乙基)乳酰胺、N,N'-双(2-羟乙基)草酰二胺、3-吗啉-1,2-丙二醇、2,6-吡啶二甲醇、3-(二甲氨基)-1,2-丙二醇、3-(二乙氨基)-1,2-丙二醇、双阿脲二水合物、(+)-N,N,N',N'-四甲基-L-酒石酸二酰胺、(-)-N,N,N',N'-四甲基-D-酒石酸二酰胺、N-丙基-N-(2,3-二羟丙基)全氟-正辛基磺酰胺、胸苷、氯霉素、甲砜霉素、D-赤酮酸内酯、甲基-4,6-O-亚苄基-α-D-吡喃葡糖苷、苯基-4,6-O-亚苄基-1-硫代-β-D-吡喃葡糖苷、1,2:5,6-二-O-亚异丙基-D-甘露醇、1,2-O-亚异丙基-α-D-呋喃木糖、2,6-二-O-棕榈酰基-L-抗坏血酸、异山梨醇和它们的环氧烷加成物、以及,对苯二酚、双酚A、双酚AP、双酚AF、双酚B、双酚BP、双酚C、双酚E、双酚F、双酚G、双酚M、双酚S、硫代双酚、双酚P、双酚PH、双酚TMC和双酚Z等具有酚性羟基的化合物的环氧烷加成物、聚碳酸酯二醇等具有碳酸酯键的醇等。
作为具有3个醇性羟基的三元醇的具体例,可举出三羟甲基乙烷、三羟甲基丙烷、甘油、三(2-羟乙基)异氰尿酸酯、己三醇、辛三醇、癸三醇、三乙醇胺、三异丙醇胺、1-[双2-(羟乙基)氨基]-2-丙醇、D-泛醇、DL-泛醇、尿苷、5-甲基尿苷、胞苷、肌苷、腺苷、柱晶白霉素A3、柱晶白霉素A4、柱晶白霉素A6、柱晶白霉素A8、盐酸克林霉素一水合物、泼尼松龙、甲基-β-D-吡喃阿拉伯糖苷、甲基-β-L-吡喃岩藻糖苷、甲基-α-L-吡喃岩藻糖苷、D-半乳醛(D-Galactal)、4-甲氧基苯基-3-O-烯丙基-β-D-吡喃半乳糖苷、4-甲氧基苯基-3-O-苄基-β-D-吡喃半乳糖苷、1,6-无水-β-D-葡萄糖、α-氯醛糖、β-氯醛糖、4,6-O-亚乙基-α-D-吡喃葡萄糖、D-己烯糖、1,2-O-亚异丙基-α-D-呋喃葡萄糖、D-葡糖醛酸-6,3-内酯、2-脱氧-D-核糖、甲基-β-D-呋喃核糖苷、D-(+)-核糖酸-1,4-内酯、甲基-β-D-吡喃木糖苷、6-O-棕榈酰基-L-抗坏血酸、6-O-硬脂酰基-L-抗坏血酸、3-O-乙基-L-抗坏血酸和它们的环氧烷加成物等。
作为具有4个醇性羟基的四元醇的具体例,可举出双三羟甲基乙烷、双三羟甲基丙烷、二甘油、季戊四醇、N,N,N',N'-四(2-羟乙基)丁二酰胺、N,N,N',N'-四(2-羟丙基)丁二酰胺、N,N,N',N'-四(2-羟乙基)己二酰胺、N,N,N',N'-四(2-羟丙基)己二酰胺、N,N,N',N'-四(2-羟乙基)乙二胺、N,N,N',N'-四(2-羟丙基)乙二胺、N-己酰基-D-葡糖胺、N-戊酰基-D-葡糖胺、N-三氟乙酰-D-葡糖胺、N-苯甲酰基-D-葡糖胺、5-乙酰胺-N,N'-双(2,3-二羟丙基)-2,4,6-三碘异邻苯二甲酰胺、螺旋霉素、克拉霉素、柱晶白霉素A1、柱晶白霉素A5、柱晶白霉素A7、柱晶白霉素A9、柱晶白霉素A13、林可霉素盐酸盐一水合物、重氮烷基脲(Diazolidinyl urea)、D-(-)-阿拉伯糖、DL-阿拉伯糖、L-(+)-阿拉伯糖、meso-赤藓醇、D-(+)-岩藻糖、L-(-)-岩藻糖、烯丙基-α-D-吡喃半乳糖苷、甲基-β-D-吡喃半乳糖苷、甲基-α-D-吡喃半乳糖苷一水合物、4-甲氧基苯基-β-D-吡喃半乳糖苷、2-硝基苯基-β-D-吡喃半乳糖苷、4-硝基苯基-α-D-吡喃半乳糖苷、4-硝基苯基-β-D-吡喃半乳糖苷、苯基-β-D-吡喃半乳糖苷、N-乙酰基-D-半乳糖胺水合物、D-(+)-半乳糖胺盐酸盐、熊果苷、2-脱氧-D-葡萄糖、七叶苷1.5水合物、D-(+)-葡糖酸-1,5-内酯、D-葡糖醛酰胺、蜗牛素、甲基-α-D-吡喃葡糖苷、甲基-β-D-吡喃葡糖苷0.5水合物、4-甲氧基苯基-β-D-吡喃葡糖苷、4-硝基苯基-β-D-吡喃葡糖苷一水合物、4-硝基苯基-α-D-吡喃葡糖苷、壬基-β-D-吡喃葡糖苷、正辛基-β-D-吡喃葡糖苷、苯基-β-D-吡喃葡糖苷水合物、根皮苷水合物、云杉苷、葛根素、N-乙酰基-D-葡糖胺、N-苯甲酰基-D-葡糖胺、D-(+)-葡糖胺盐酸盐、N-己酰基-D-葡糖胺、N-戊酰基-D-葡糖胺、L-(+)-古洛糖酸-γ-内酯、D-(-)-来苏糖、L-(+)-来苏糖、3,4-O-亚异丙基-D-甘露醇、甲基-α-D-吡喃甘露糖苷、D-甘露糖酸-1,4-内酯、4-甲氧基苯基-α-D-吡喃甘露糖苷、N-乙酰基-D-甘露糖胺一水合物、D-(-)-核糖、L-核糖、D-(+)-木糖、DL-木糖、L-(-)-木糖、D-阿拉伯糖型抗坏血酸、L-抗坏血酸、L-苏糖醇和它们的环氧烷加成物等。
作为具有5个醇性羟基的五元醇的具体例,可举出三(三羟甲基)乙烷、三(三羟甲基)丙烷、三甘油、双(2-羟乙基)氨基三(羟甲基)甲烷、双(2-羟丙基)氨基三(羟甲基)甲烷、N,N,N',N”,N”-五(2-羟乙基)二乙三胺、N,N,N',N”,N”-五(2-羟丙基)二乙三胺、米格列醇、红霉素、阿奇霉素二水合物、D-(+)-阿糖醇、DL-阿糖醇、L-(-)-阿糖醇、D-(-)-果糖、L-(+)-果糖、D-(+)-半乳糖、L-(-)-半乳糖、β-D-葡萄糖、D-(+)-葡萄糖、L-(-)-葡萄糖、D-葡萄糖二乙基缩硫醛、水杨苷、L-古洛糖、D-(+)-甘露糖、L-(-)-甘露糖、核糖醇、L-(-)-山梨糖、D-塔格糖、木糖醇、三氯半乳蔗糖、抗坏血酸甘油酯和它们的环氧烷加成物等。
作为具有6个以上醇性羟基的多元醇的具体例,可举出聚三羟甲基乙烷、聚三羟甲基丙烷、聚甘油、二季戊四醇、三季戊四醇、聚季戊四醇、碘海醇、半乳糖醇、D-山梨糖醇、L-山梨糖醇、myo-肌醇、scyl lo-肌醇、D-甘露醇、L-甘露醇、淫羊藿苷、苦杏仁苷、D-(+)-纤维二糖、地奥司明、2-O-α-D-吡喃葡糖基-L-抗坏血酸、橙皮苷、D-(+)-乳糖一水合物、乳果糖、D-(+)-麦芽糖一水合物、D-(+)-蜜二糖一水合物、甲基橙皮苷、麦芽糖醇、柚皮苷水合物、新橙皮苷双氢查尔酮水合物、帕拉金糖水合物、芦丁水合物、D-(+)-蔗糖、蛇菊苷、D-(+)-松二糖、D-(+)-海藻糖(无水)、D-(+)-海藻糖二水合物、D-(+)-松三糖水合物、D-(+)-棉子糖五水合物、瑞莱鲍迪苷A、水苏四糖、α-环糊精、β-环糊精、γ-环糊精、淀粉、聚乙烯醇和它们的环氧烷加成物等。
本发明中,可以将这些醇单独使用或任意组合2种以上使用。在这些醇中,优选具有3个以上醇性羟基的多元醇,特别优选三羟甲基乙烷、三羟甲基丙烷、甘油、甘油的环氧烷加成物、三(2-羟乙基)异氰尿酸酯、三乙醇胺、双三羟甲基乙烷、双三羟甲基丙烷、二甘油、二甘油的环氧烷加成物、季戊四醇、季戊四醇的环氧烷加成物、木糖醇、二季戊四醇、二季戊四醇的环氧烷加成物、D-山梨糖醇、聚甘油。予以说明,关于这些醇,当存在其水合物或溶剂合物时,该水合物和溶剂合物也可用作本发明的制造方法中的醇。
本发明中作为原料使用的单官能(甲基)丙烯酸酯为分子中具有1个(甲基)丙烯酰基的化合物,例如可举出下述通式(1)表示的化合物。
[化1]
式中,R1表示氢原子或甲基。R2表示碳数1~50的有机基团。
作为上述通式(1)中的R2的具体例,可举出甲基、乙基、正-或异-丙基、正-、异-或叔-丁基、正、仲-或叔-戊基、新戊基、正、仲-或叔-己基、正、仲-或叔-庚基、正、仲-或叔-辛基、2-乙基己基、辛基、壬基、癸基、十一烷基、月桂基、十三烷基、肉豆蔻基、十五烷基、鲸蜡基、十七烷基、硬脂基、十九烷基、二十烷基、二十六烷基、三十烷基、蜂花基、乙烯基、烯丙基、甲代烯丙基、巴豆基、1,1-二甲基-2-丙烯基、2-甲基丁烯基、3-甲基-2-丁烯基、3-甲基-3-丁烯基、2-甲基-3-丁烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、十一烯基、十二烯基、十三烯基、十四烯基、十五烯基、十六烯基、十七烯基、油烯基、十八碳二烯基、十八碳三烯基、环戊基、环戊基甲基、环己基、环己基甲基、4-甲基环己基、4-叔丁基环己基、三环癸基、异冰片基、金刚烷基、二环戊烷基、二环戊烯基、苯基、甲基苯基、二甲基苯基、三甲基苯基、4-叔丁基苯基、苄基、二苯基甲基、二苯基乙基、三苯基甲基、肉桂基、萘基、蒽基、甲氧基乙基、甲氧基乙氧基乙基、甲氧基乙氧基乙氧基乙基、3-甲氧基丁基、乙氧基乙基、乙氧基乙氧基乙基、环戊氧基乙基、环己氧基乙基、环戊氧基乙氧基乙基、环己氧基乙氧基乙基、二环戊烯氧基乙基、苯氧基乙基、苯氧基乙氧基乙基、缩水甘油基、β-甲基缩水甘油基、β-乙基缩水甘油基、3,4-环氧基环己基甲基、2-环氧丙烷基甲基、3-甲基-3-环氧丙烷基甲基、3-乙基-3-环氧丙烷基甲基、四氢呋喃基、四氢糠基、四氢吡喃基、二烷酮基(Dioxazolanyl)、二烷基、N,N-二甲氨基乙基、N,N-二乙氨基乙基、N,N-二甲氨基丙基、N,N-二乙氨基丙基、N-苄基-N-甲氨基乙基、N-苄基-N-甲氨基丙基等。
本发明中,可以将这些单官能(甲基)丙烯酸酯单独或任意组合2种以上使用。这些单官能(甲基)丙烯酸酯中,优选丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸2-乙基己酯、丙烯酸2-甲氧基乙酯、丙烯酸2-二甲氨基乙酯。特别优选对几乎所有的醇显示出良好的反应性、且容易获得的丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸2-甲氧基乙酯。进一步优选促进醇的溶解、显示极为良好的反应性的丙烯酸2-甲氧基乙酯。
本发明制造方法中的醇与单官能(甲基)丙烯酸酯的使用比例没有特殊限制,但相对于醇的羟基1摩尔,优选使用单官能(甲基)丙烯酸酯0.4~10.0摩尔,更优选使用0.6~5.0摩尔。单官能(甲基)丙烯酸酯少于0.4摩尔时,副反应增多。另外,多于10.0摩尔时,(甲基)丙烯酸酯的生成量减少,生产率差。
本发明的制造方法可以不使用溶剂来实施,也可以根据需要使用溶剂。作为溶剂的具体例,可举出正己烷、环己烷、甲基环己烷、正庚烷、正辛烷、正壬烷、正癸烷、苯、甲苯、二甲苯、乙基苯、二乙基苯、异丙基苯、戊基苯、二戊基苯、三戊基苯、十二烷基苯、双十二烷基苯、戊基甲苯、异丙基甲苯、萘烷基、萘满基等烃类;乙醚、二丙基醚、二异丙基醚、二丁基醚、二戊基醚、二乙基缩醛、二己基缩醛、叔丁基甲基醚、环戊基甲基醚、四氢呋喃、四氢吡喃、三烷、二烷、苯甲醚、二苯基醚、二甲基溶纤剂、二甘醇二甲醚、三甘醇二甲醚、四甘醇二甲醚等醚类;18-冠醚-6等冠醚类;甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、叔丁醇、乙二醇、2-甲氧基乙醇、甘油等醇类;苯甲酸甲酯、γ-丁内酯等酯类;丙酮、丁酮、甲基异丁基酮、环己酮、苯乙酮、二苯甲酮等酮类;环丁砜等砜类;二甲亚砜等亚砜类;碳酸二甲酯、碳酸二乙酯、碳酸乙烯酯、碳酸丙烯酯、碳酸1,2-丁烯酯等碳酸酯化合物;脲类或其衍生物;三丁基氧化膦等氧化膦类;咪唑盐、哌啶盐、吡啶盐等离子液体;硅油、水等。这些溶剂中,优选烃类、醚类、醇类、碳酸酯化合物、离子液体。这些溶剂既可以单独使用,也可以任意组合2种以上作为混合溶剂使用。
本发明制造方法中的催化剂A为选自具有氮杂双环结构的环状叔胺或其盐或其配合物、脒或其盐或其配合物、具有吡啶环的化合物或其盐或其配合物、膦或其盐或其配合物、具有叔二胺结构的化合物或其盐或其配合物中的一种以上化合物。
具有上述氮杂双环结构的环状叔胺或其盐或其配合物的具体例,可举出1-氮杂双环[1,1,0]丁烷、1,3-二氮杂双环[1,1,0]丁烷、1-氮杂双环[2,1,0]庚烷、1,3-二氮杂双环[2,1,0]庚烷、1,4-二氮杂双环[2,1,0]庚烷、1-氮杂双环[2,2,0]己烷、1,3-二氮杂双环[2,2,0]己烷、1-氮杂双环[2,1,1]己烷、1,3-二氮杂双环[2,1,1]己烷、1-氮杂双环[2,2,1]庚烷、1,3-二氮杂双环[2,2,1]庚烷、1,4-二氮杂双环[2,2,1]庚烷、1-氮杂双环[3,2,0]庚烷、1,3-二氮杂双环[3,2,0]庚烷、1,4-二氮杂双环[3,2,0]庚烷、1,6-二氮杂双环[3,2,0]庚烷、1,3-二氮杂双环[2,2,2]辛烷、1-氮杂双环[3,2,1]辛烷、1,3-二氮杂双环[3,2,1]辛烷、1,4-二氮杂双环[3,2,1]辛烷、1,5-二氮杂双环[3,2,1]辛烷、1,6-二氮杂双环[3,2,1]辛烷、1-氮杂双环[4,1,1]辛烷、1,3-二氮杂双环[4,1,1]辛烷、1,4-二氮杂双环[4,1,1]辛烷、1,5-二氮杂双环[4,1,1]辛烷、1,6-二氮杂双环[4,1,1]辛烷、1,7-二氮杂双环[4,1,1]辛烷、1-氮杂双环[4,2,0]辛烷、1,3-二氮杂双环[4,2,0]辛烷、1,4-二氮杂双环[4,2,0]辛烷、1,5-二氮杂双环[4,2,0]辛烷、1,7-二氮杂双环[4,2,0]辛烷、1-氮杂双环[3,3,1]壬烷、1,3-二氮杂双环[3,3,1]壬烷、1,4-二氮杂双环[3,3,1]壬烷、1,5-二氮杂双环[3,3,1]壬烷、1-氮杂双环[3,2,2]壬烷、1,3-二氮杂双环[3,2,2]壬烷、1,4-二氮杂双环[3,2,2]壬烷、1,5-二氮杂双环[3,2,2]壬烷、1,6-二氮杂双环[3,2,2]壬烷、1,8-二氮杂双环[3,2,2]壬烷、1-氮杂双环[4,3,0]壬烷、1,3-二氮杂双环[4,3,0]壬烷、1,4-二氮杂双环[4,3,0]壬烷、1,5-二氮杂双环[4,3,0]壬烷、1,6-二氮杂双环[4,3,0]壬烷、1,7-二氮杂双环[4,3,0]壬烷、1,8-二氮杂双环[4,3,0]壬烷、1-氮杂双环[4,2,1]壬烷、1,3-二氮杂双环[4,2,1]壬烷、1,4-二氮杂双环[4,2,1]壬烷、1,5-二氮杂双环[4,2,1]壬烷、1,6-二氮杂双环[4,2,1]壬烷、1,7-二氮杂双环[4,2,1]壬烷、1-氮杂双环[5,2,0]壬烷、1,3-二氮杂双环[5,2,0]壬烷、1,3-二氮杂双环[5,2,0]壬烷、1,4-二氮杂双环[5,2,0]壬烷、1,5-二氮杂双环[5,2,0]壬烷、1,6-二氮杂双环[5,2,0]壬烷、1,7-二氮杂双环[5,2,0]壬烷、1,8-二氮杂双环[5,2,0]壬烷、1-氮杂双环[5,1,1]壬烷、1,3-氮杂双环[5,1,1]壬烷、1,4-氮杂双环[5,1,1]壬烷、1,5-氮杂双环[5,1,1]壬烷、1,6-氮杂双环[5,1,1]壬烷、1,7-氮杂双环[5,1,1]壬烷、1-氮杂双环[6,1,0]壬烷、1,3-二氮杂双环[6,1,0]壬烷、1,4-二氮杂双环[6,1,0]壬烷、1,5-二氮杂双环[6,1,0]壬烷、1,6-二氮杂双环[6,1,0]壬烷、1,7-二氮杂双环[6,1,0]壬烷、1,8-二氮杂双环[6,1,0]壬烷、1-氮杂双环[7,1,0]癸烷、1,9-二氮杂双环[7,1,0]癸烷、1-氮杂双环[6,2,0]癸烷、1,8-二氮杂双环[6,2,0]癸烷、1-氮杂双环[6,1,1]癸烷、1,8-二氮杂双环[6,1,1]癸烷、1-氮杂双环[5,3,0]癸烷、1,7-二氮杂双环[5,3,0]癸烷、1-氮杂双环[5,2,1]癸烷、1,7-二氮杂双环[5,2,1]癸烷、1-氮杂双环[4,3,1]癸烷、1,6-二氮杂双环[4,3,1]癸烷、1-氮杂双环[4,2,2]癸烷、1,6-二氮杂双环[4,2,2]癸烷、1-氮杂双环[5,4,0]十一烷、1,7-二氮杂双环[5,4,0]十一烷、1-氮杂双环[5,3,1]十一烷、1,7-二氮杂双环[5,3,1]十一烷、1-氮杂双环[5,2,2]十一烷、1,7-二氮杂双环[5,2,2]十一烷、1-氮杂双环[4,4,1]十一烷、1,7-二氮杂双环[4,4,1]十一烷、1-氮杂双环[4,3,2]十一烷、1,7-二氮杂双环[4,3,2]十一烷、1-氮杂双环[3,3,0]辛烷、1-氮杂双环[4,3,0]壬烷、奎宁环、羽扇豆烷、羽扇豆宁、喹嗪、3-羟基奎宁环、3-奎宁环酮、Quincor ine、Quincoridine、辛可尼丁、辛可宁、奎尼辛、奎宁、去甲奎宁、伊波加因、斯烷宁、澳栗碱、米安色林、米氮平、坎那丁、特勒格碱(base)、1-氮杂双环[2,2,2]辛烷-3-羧酸、三乙二胺(别名DABCO)、2-(羟甲基)三乙二胺、六亚甲基四胺、3-喹嗪酮盐酸盐、3-氯-1-氮杂双环[2,2,2]辛烷盐酸盐、辛可尼丁二盐酸盐、辛可宁盐酸盐水合物、辛可尼丁硫酸盐二水合物、氢化奎尼丁盐酸盐、辛可宁硫酸盐二水合物、奎宁盐酸盐二水合物、硫酸奎宁二水合物、奎宁磷酸盐、奎尼辛硫酸盐二水合物、米安色林盐酸盐、1,1'-(丁烷-1,4-二基)双[4-氮杂-1-氮双环[2,2,2]辛烷]二溴化物、1,1'-(癸烷-1,10-二基)双[4-氮杂-1-氮双环[2,2,2]辛烷]二溴化物、双(三甲基铝)-1,4-二氮杂双环[2,2,2]辛烷加成物、三氧化铋、奎宁环盐酸盐、3-奎宁环酮盐酸盐、3-羟基奎宁环盐酸盐、DABCO盐酸盐、2-(羟甲基)三乙二胺盐酸盐、奎宁环乙酸盐、3-奎宁环酮乙酸盐、3-羟基奎宁环乙酸盐、DABCO乙酸盐、2-(羟甲基)三乙二胺乙酸盐、奎宁环丙烯酸盐、3-奎宁环酮丙烯酸盐、3-羟基奎宁环丙烯酸盐、DABCO丙烯酸盐、2-(羟甲基)三乙二胺丙烯酸盐等。
作为上述脒或其盐或其配合物的具体例,可举出咪唑、N-甲基咪唑、N-乙基咪唑、1-苄基-2-甲基咪唑、1-苄基-2-苯基咪唑、1-乙烯基咪唑、1-烯丙基咪唑、1,8-二氮杂双环[5,4,0]十一碳-7-烯(别名:DBU)、1,5-二氮杂双环[4,3,0]壬-5-烯(别名:DBN)、N-甲基咪唑盐酸盐、DBU盐酸盐、DBN盐酸盐、N-甲基咪唑乙酸盐、DBU乙酸盐、DBN乙酸盐、N-甲基咪唑丙烯酸盐、DBU丙烯酸盐、DBN丙烯酸盐、邻苯二甲酰亚胺DBU等。
作为上述具有吡啶环的化合物或其盐或其配合物的具体例,可举出吡啶、2-甲基吡啶、3-甲基吡啶、4-甲基吡啶、2-乙基吡啶、3-乙基吡啶、4-乙基吡啶、2-丙基吡啶、4-丙基吡啶、4-异丙基吡啶、4-叔丁基吡啶、4-戊基吡啶、4-(1-乙基丙基)吡啶、4-(5-壬基)吡啶、2-乙烯基吡啶、2,3-二甲基吡啶、2,4-二甲基吡啶、2,5-二甲基吡啶、2,6-二甲基吡啶、3,4-二甲基吡啶、3,5-二甲基吡啶、3,5-二乙基吡啶、N,N-二甲基-4-氨基吡啶(别名:DMAP)、2,4,6-三甲基吡啶、2,6-二叔丁基吡啶、N,N-二甲基-2-氨基吡啶、4-哌啶基吡啶、4-吡咯烷吡啶、4-苯基吡啶、喹啉、2-甲基喹啉、3-甲基喹啉、4-甲基喹啉、6-甲基喹啉、7-甲基喹啉、8-甲基喹啉、异喹啉、1-甲基异喹啉、吖啶、3,4-苯并喹啉、5,6-苯并喹啉、7,8-苯并喹啉、2-羟基吡啶、3-羟基吡啶、4-羟基吡啶、2,6-二羟基吡啶、2-(羟甲基)吡啶、3-(羟甲基)吡啶、4-(羟甲基)吡啶、5-羟基异喹啉、2-甲氧基吡啶、3-甲氧基吡啶、4-甲氧基吡啶、2,6-二甲氧基吡啶、1,5-萘啶、1,6-萘啶、1,7-萘啶、1,8-萘啶、2,6-萘啶、2,7-萘啶、2,2'-联吡啶、3,3'-联吡啶、4,4'-联吡啶、2,3'-联吡啶、2,4'-联吡啶、3,4'-联吡啶、4,4'-亚乙基联吡啶、1,3-二(4-吡啶基)丙烷、1,10-菲咯啉一水合物、2-(三甲基甲硅烷基)吡啶、DMAP盐酸盐、DMAP乙酸盐、DMAP丙烯酸盐、1-甲基氯化吡啶、1-丙基氯化吡啶、硼烷-吡啶复合物、硼烷-2-甲基吡啶复合物、对甲苯磺酸吡啶等。
上述膦或其盐或其配合物可举出含有下述通式(2)表示的结构的化合物等。
[化2]
式中,R3、R4和R5可以相同或不同,为碳数1~20的直链或支链状烷基、碳数1~20的直链或支链状烯基、碳数6~24的芳基、或碳数5~20的环烷基,它们可具有取代基。
作为具体例,可举出三苯基膦、(S)-(-)-BINAP、(R)-(+)-BINAP、(±)-BINAP、2,2'-双(二苯基膦)联苯、Xantphos(4,5-双二苯基膦-9,9-二甲基氧杂蒽)、4,6-双(二苯基膦)吩嗪、双[2-(二苯基膦)苯基]醚、(2-溴苯基)二苯基膦、双(五氟苯基)苯基膦、二苯基膦苯-3-磺酸钠、二苯基-1-芘基膦、二苯基-2-吡啶基膦、4-(二甲氨基)苯基二苯基膦、1,1'-双(二苯基膦)二茂铁、(R,R”)-2,2”-双(二苯基膦)-1,1”-联二茂铁、(R)-N,N-二甲基-1-[(S)-2-(二苯基膦)二茂铁基]乙胺、(S)-N,N-二甲基-1-[(R)-2-(二苯基膦)二茂铁基]乙胺、(R)-N,N-二甲基-1-[(S)-1',2-双(二苯基膦)二茂铁基]乙胺、(S)-N,N-二甲基-1-[(R)-1',2-双(二苯基膦)二茂铁基]乙胺、4-二苯基膦甲基聚苯乙烯树脂、(R)-(+)-2-二苯基膦-2'-甲氧基-1,1'-联萘、(S)-(-)-2-二苯基膦-2'-甲氧基-1,1'-联萘、2-(二苯基膦)苯甲酸、4-(二苯基膦)苯甲酸、2-(二苯基膦)苯甲醛、(S)-(-)-5,5'-双[二(3,5-二甲苯基)膦]-4,4'-联-1,3-苯并二氧杂环戊烯、(R)-(+)-5,5'-双[二(3,5-二甲苯基)膦]-4,4'-联-1,3-苯并二氧杂环戊烯、(S)-(+)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-联-1,3-苯并二氧杂环戊烯、(R)-(-)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-联-1,3-苯并二氧杂环戊烯、(五氟苯基)二苯基膦、(S)-(-)-5,5'-双(二苯基)-4,4'-联-1,3-苯并二氧杂环戊烯、(R)-(+)-5,5'-双(二苯基膦)-4,4'-联-1,3-苯并二氧杂环戊烯、三(4-甲氧基苯基)膦、三(对甲苯基)膦、三(邻甲苯基)膦、三(间甲苯基)膦、三(2,6-二甲氧基苯基)膦、三苯基硼烷-三苯基膦复合物、三苯基膦硼烷、三(五氟苯基)膦、三[3,5-双(三氟甲基)苯基]膦、三(4-氟苯基)膦、对苯乙烯基二苯基膦、四苯基溴化、甲基三苯基溴化、正丁基三苯基溴化、甲氧基甲基三苯基氯化、苄基三苯基氯化、四苯基四苯基硼酸盐、四苯基四-对甲苯基硼酸盐、乙基三苯基乙酸-乙酸配合物、乙基三苯基碘、三(4-甲氧基-3,5-二甲基苯基)膦、(+)-DIOP、(-)-DIOP、1,2-双(二苯基膦)乙烷、1,3-双(二苯基膦)丙烷、1,2-双(二甲基膦)乙烷、1,4-双(二苯基膦)丁烷、1,6-双(二苯基膦)己烷、1,5-双(二苯基膦)戊烷、双(二苯基膦)甲烷、反式-1,2-双(二苯基膦)乙烯、(S,S)-Chiraphos、(R,R)-DIPAMP、(S,S)-DIPAMP、1,2-双[双(五氟苯基)膦]乙烷、(2R,3R)-(-)-Norphos、(2S,3S)-(+)-Norphos、2-丁烯基(二叔丁基)膦、环己基二苯基膦、二环己基(1,1-二苯基-1-丙烯-2-基)膦、二乙基苯基膦、二环己基苯基膦、二苯基丙基膦、2-(二叔丁基膦)联苯、2-(二环己基膦)联苯、2-(二环己基膦)-2'-(二甲氨基)联苯、1-[2-(二叔丁基膦)苯基]-3,5-二苯基-1H-吡唑、二叔丁基苯基膦、(4-二甲氨基苯基)二叔丁基膦、二叔丁基(3-甲基-2-丁烯基)膦、乙基二苯基膦、异丙基二苯基膦、甲基二苯基膦、三环己基膦、三(2-呋喃基)膦、三(2-噻吩基)膦、三叔丁基膦、三环戊基膦等。
上述具有叔二胺结构的化合物或其盐或其配合物可举出含有下述通式(3)表示的结构的化合物等。
[化3]
(式中,R6、R7、R8和R9相同或不同,为碳数1~20的直链或支链状烷基、碳数1~20的直链或支链状烯基、碳数6~24的芳基、或碳数5~20的环烷基,可具有氨基、羟基、醚键、酯键、碳酸酯键、酰胺键、尿烷键。R10和R11为氢原子或甲基。n为1~12的整数。)
作为上述具有叔二胺结构的化合物或其盐或其配合物的具体例,可举出N,N,N',N'-四甲基二氨基甲烷、N,N,N',N'-四甲基乙二胺、N,N,N',N”,N”-五甲基二乙三胺、三[2-(二甲氨基)乙基]胺、N,N,N',N'-四甲基-1,2-二氨基丙烷、N'-(2-羟乙基)-N,N,N'-三甲基乙二胺、1-(2-二甲氨基乙基)-4-甲基哌嗪、N,N,N',N'-四甲基-1,3-丙二胺、N-甲基-N,N-双[3-(二甲氨基)丙基]胺、N,N,N',N'-四甲基-2,2-二甲基-1,3-丙二胺、N,N,N',N'-四甲基-1,3-丁二胺、N,N,N',N'-四甲基-1,4-丁二胺、N,N,N',N'-四甲基-1,6-己二胺、N,N,N',N'-四甲基-1,6-己二胺盐酸盐、N,N,N',N'-四甲基-1,6-己二胺乙酸盐、N,N,N',N'-四甲基-1,6-己二胺丙烯酸盐等。
本发明中,可以将这些催化剂A单独使用或任意组合2种以上使用。在这些催化剂A中,优选奎宁环、3-奎宁环酮、3-羟基奎宁环、DABCO、2-(羟甲基)三乙二胺、N-甲基咪唑、DBU、DBN、DMAP、三苯基膦、三(对甲苯基)膦、三(间甲苯基)膦、三(4-甲氧基苯基)膦、三(4-甲氧基-3,5-二甲基苯基)膦、N,N,N',N'-四甲基-1,6-己二胺,特别优选对几乎所有的醇均显示出良好的反应性、且容易获得的3-羟基奎宁环、DABCO、2-(羟甲基)三乙二胺、N-甲基咪唑、DBU、DMAP、三苯基膦、三(间甲苯基)膦、N,N,N',N'-四甲基-1,6-己二胺。
本发明制造方法中的催化剂A的使用量没有特殊限制,相对于醇的羟基1摩尔,优选使用催化剂A 0.0001~0.5摩尔,更优选使用0.0005~0.2摩尔。少于0.0001摩尔时,目标(甲基)丙烯酸酯的生成量减少,多于0.5摩尔时,副产物增多,反应液的着色增加,因而,反应结束后的精制工序变得复杂。
本发明制造方法中的催化剂B为选自含锌化合物中的一种以上的化合物,可举出:下述通式(4)表示的含有有机酸锌的化合物;下述通式(5)表示的含有二酮烯醇锌的化合物;草酸锌等。
[化4]
式中,R12和R13可以相同或不同,为碳数1~20的直链或支链状烷基、碳数1~20的直链或支链状烯基、碳数6~24的芳基、或碳数5~20的环烷基,它们可具有取代基。其中,R12和R13不具有氟和氯等卤原子。
[化5]
式中,R14、R15、R16、R17、R18和R19可以相同或不同,为碳数1~20的直链或支链状烷基、碳数1~20的直链或支链状烯基、碳数6~24的芳基、或碳数5~20的环烷基,它们可具有取代基。
作为上述通式(4)表示的含有有机酸锌的化合物的具体例,可举出乙酸锌、乙酸锌二水合物、丙酸锌、辛酸锌、新癸酸锌、月桂酸锌、肉豆蔻酸锌、硬脂酸锌、环己烷丁酸锌、2-乙基己酸锌、苯甲酸锌、叔丁基苯甲酸锌、水杨酸锌、环烷酸锌、丙烯酸锌、甲基丙烯酸锌等。予以说明,对于这些含锌化合物,当存在其水合物、溶剂合物、或者与催化剂A的配合物时,该水合物、该溶剂合物、以及与催化剂A的配合物也可以作为本发明制造方法中的催化剂B使用。
作为上述通式(5)表示的含有二酮烯醇锌的化合物的具体例,可举出乙酰丙酮锌、乙酰丙酮锌水合物、双(2,6-二甲基-3,5-庚二酮)锌、双(2,2,6,6-四甲基-3,5-庚二酮)锌、双(5,5-二甲基-2,4-己二酮)锌等。予以说明,对于这些含锌化合物,当存在其水合物、溶剂合物、或者与催化剂A的配合物时,该水合物、溶剂合物、以及与催化剂A的配合物也可以作为本发明制造方法中的催化剂B使用。
作为本发明制造方法中的催化剂B,可直接使用上述的化合物,但也可以在反应体系内生成这些化合物来使用。例如可举出以下方法:使用金属锌、氧化锌、氢氧化锌、氯化锌和硝酸锌等其他锌化合物作为原料,在采用有机酸锌的情况下,使这些锌化合物与有机酸反应的方法,在采用二酮烯醇锌的情况下,使这些锌化合物与1,3-二酮反应的方法等。
在本发明的制造方法中,可以将这些催化剂B单独使用或任意组合2种以上使用。在这些催化剂B中,优选乙酸锌、丙酸锌、丙烯酸锌、甲基丙烯酸锌、乙酰丙酮锌。特别优选对几乎所有的醇均显示出良好的反应性、且容易获得的乙酸锌、丙烯酸锌、乙酰丙酮锌。
本发明制造方法中的催化剂B的使用量没有特殊限制,相对于醇的羟基1摩尔,优选使用催化剂B 0.0001~0.5摩尔,更优选使用0.0005~0.2摩尔。少于0.0001摩尔时,目标的(甲基)丙烯酸酯的生成量减少,多于0.5摩尔时,副产物增多,反应液的色调变差,因而反应结束后的精制工序变得复杂。
本发明制造方法中的催化剂A与催化剂B的使用比例没有特殊限制,相对于1摩尔催化剂B,优选使用催化剂A 0.005~10.0摩尔,更优选使用0.05~5.0摩尔。少于0.005摩尔时,目标的(甲基)丙烯酸酯的生成量减少,多于10.0摩尔时,副产物增多,反应液的色调变差,因而反应结束后的精制工序变得复杂。
在本发明的制造方法中,并用的催化剂A和催化剂B最优选催化剂A为DABCO、催化剂B为乙酸锌和/或丙烯酸锌的组合。该组合可有效地获得目标的(甲基)丙烯酸酯,除此以外,反应结束后的色调也优异,因此,可适合用于重视色调的各种工业用途。进而,该组合由于是可以比较廉价地获得的催化剂,因而在经济上有利。
另外,也可以在本发明的制造方法的酯交换反应结束后,从反应性产物中回收催化剂A和/或催化剂B,并将该回收催化剂再次用于酯交换反应。
在本发明的制造方法中,推测酯交换反应通过如图1所示的反应机制来进行。首先,通过将催化剂A加成在单官能(甲基)丙烯酸酯的β位碳上,使得羰基氧原子上的电子密度增加,其进一步攻击其他单官能(甲基)丙烯酸酯的羰基碳,由此生成图1所示的反应中间体。推测:随后,通过使该中间体与醇发生酯交换反应,由此生成了目标的(甲基)丙烯酸酯。推测此时,具有路易斯酸酸性的催化剂B通过使(甲基)丙烯酰基活化,促进了图1所示的反应机制。
本发明制造方法中使用的催化剂A和催化剂B既可以从上述反应的最初添加,也可以从中途添加。另外,既可以将期望的使用量汇总性地添加,也可以分批添加。另外,当催化剂A和/或催化剂B为固体时,可以用溶剂溶解后添加。
本发明制造方法中的酯交换反应的反应温度优选为40~180℃,特别优选为60~160℃。反应温度低于40℃时,反应速度极慢,反应温度超过180℃时,引起(甲基)丙烯酰基的热聚合,或反应液的色调变差,因此反应结束后的精制工序变得复杂。
本发明制造方法中的酯交换反应的反应压力只要能维持规定的反应温度,就没有特殊限制,既可以在减压状态下实施,也可以在加压状态下实施。通常为0.000001~10MPa(绝对压力)。
在本发明的制造方法中,随着酯交换反应的进行,副产出来自作为原料使用的单官能(甲基)丙烯酸酯的一元醇。该一元醇虽然可以原样共存在反应体系内,但通过将该一元醇排出到反应体系外,可进一步促进酯交换反应的进行。
在本发明的制造方法中,为了良好地维持反应液的色调,可以向体系内导入氩、氦、氮和二氧化碳等非活性气体。另外,为了防止(甲基)丙烯酰基的聚合,可以向体系内导入含氧气体。作为含氧气体的具体例,可举出空气、氧和氮的混合气体、氧和氦的混合气体等。作为该气体的导入方法,可举出向反应产物中吹入(所谓的鼓泡)的方法、或者加压过滤、吸滤等在过滤操作时引入气相部的方法。
在本发明的制造方法中,为了防止(甲基)丙烯酰基的聚合,优选在体系内添加阻聚剂。作为阻聚剂的具体例,可举出对苯二酚、叔丁基对苯二酚、对苯二酚单甲基醚、2,6-二叔丁基-4-甲基苯酚、2,4,6-三叔丁基苯酚、4-叔丁基邻苯二酚、苯醌、吩噻嗪、N-亚硝基-N-苯基羟胺铵、2,2,6,6-四甲基哌啶-1-氧基、4-羟基-2,2,6,6-四甲基哌啶-1-氧基等有机系阻聚剂;氯化铜、硫酸铜和硫酸铁等无机系阻聚剂;二丁基二硫代氨基甲酸铜、N-亚硝基-N-苯基羟胺铝盐等有机盐系阻聚剂。阻聚剂可以单独添加一种,也可以任意组合2种以上添加。另外,阻聚剂既可以从反应的最初添加,也可以从中途添加。进而,阻聚剂可以将期望的使用量汇总性地添加,也可以分批添加。阻聚剂可以经由精馏塔连续地添加。作为阻聚剂的添加量,优选向反应液中添加5~30,000质量ppm,更优选添加25~10,000质量ppm。少于5质量ppm时,阻聚效果不充分,多于30,000质量ppm时,反应液的色调变差,或者得到的(甲基)丙烯酸酯的固化速度下降,因而反应结束后的精制工序变得复杂。
本发明制造方法中的酯交换反应的反应时间根据催化剂的种类和使用量、反应温度、反应压力等的不同而不同,通常为0.1~150小时,优选为0.5~80小时。
本发明制造方法中的酯交换反应可以通过间歇式、半间歇式、连续式中的任一种方法实施。作为间歇式的一例,可举出以下方式:向反应器中装入醇、单官能(甲基)丙烯酸酯、催化剂、阻聚剂,一边使含氧气体鼓泡入反应液中,一边在规定温度下搅拌。然后,随着酯交换反应的进行,副产出来自作为原料使用的单官能(甲基)丙烯酸酯的一元醇。通过将该一元醇在规定压力下从反应器中取出,可生成目标的(甲基)丙烯酸酯。
在本发明的制造方法中,通过对酯交换反应的反应产物进行与吸附剂C的接触处理,能够得到催化剂被充分除去的高品质的(甲基)丙烯酸酯。
本发明制造方法中的吸附剂C为选自含有镁、铝、硅的至少一种的氧化物和氢氧化物中的一种以上的化合物。
作为上述吸附剂C的具体例,可举出氧化镁(例如,协和化学工业株式会社制キョーワマグ(商品名)、キョーワマグMF(商品名)等)、氢氧化镁(例如,协和化学工业株式会社制キスマHB(商品名)等)、氧化铝(例如,住友化学株式会社制活性氧化铝、水硬性氧化铝、水泽化学工业株式会社制活性氧化铝GB(商品名)、协和化学工业株式会社制キョーワード200(商品名)等)、氢氧化铝、水滑石类化合物(例如,协和化学工业株式会社制DHT-4A(商品名)、キョーワード500(商品名)、キョーワード1000(商品名)等)、镁-铝复合氧化物(例如,协和化学工业株式会社制キョーワード300(商品名)、キョーワード2000(商品名)等)、硅酸镁(例如,协和化学工业株式会社制キョーワード600(商品名)、水泽化学工业株式会社制ミズカライフ(商品名)等)、硅酸铝(例如,协和化学工业株式会社制キョーワード700(商品名)、水泽化学工业株式会社制ネオビードSA(商品名)等)、蒙脱石系化合物(例如,水泽化学工业株式会社制ガレオンアース(商品名)、ミズカエース(商品名)、ガレオナイト(商品名)等)、膨润土系化合物(例如,水泽化学工业(株)制ベンクレイ(商品名)等)、海泡石系化合物(例如,水泽化学工业株式会社制エードプラス(商品名)等)、二氧化硅系化合物(例如,水泽化学工业株式会社制シルホナイト(商品名)、シルビードN(商品名)、DSL日本株式会社制カープレックス(商品名)等)、沸石(例如,水泽化学工业株式会社制ミズカシーブス(商品名)、ミズカシーブスEX(商品名)等)等。它们既可以从天然采掘,也可以为合成品。另外,还可以含有锂、钠、钾、铯等碱金属;钙等碱土类金属;铁、锌等过渡元素;铈等稀土类元素;水、碳酸根离子等。
本发明中,可以将这些吸附剂C单独使用或任意组合2种以上使用。在这些吸附剂C中,优选硅酸镁、硅酸铝、水滑石类化合物,特别优选吸附能力极高、且容易获得的硅酸镁和硅酸铝。
本发明制造方法中的吸附剂C的使用量没有特殊限定,相对于目标(甲基)丙烯酸酯1份,优选使用0.001~1.5份的吸附剂C,特别优选使用0.005~0.8份。少于0.001份时,催化剂的除去效果不充分,多于1.5份时,吸附剂C与目标(甲基)丙烯酸酯的分离变得复杂。
本发明制造方法中使用的吸附剂C既可以自酯交换反应的最初使用,也可以从中途使用。但优选在酯交换反应结束后使用。另外,既可以将期望的使用量汇总性地使用,也可以分批地使用。当吸附剂C为固体时,可以用溶剂溶解后添加,当吸附剂C为粉末状时,可以用溶剂润湿,或者分散在溶剂中作为浆料来添加。
本发明制造方法中的酯交换反应的反应产物与吸附剂C的接触处理的实施温度没有特殊限制,优选为0~150℃,特别优选为30~130℃。反应温度低于0℃时,催化剂的除去效果不充分,超过150℃时,有时吸附剂C引发副反应,精制工序变得复杂。
本发明制造方法中的酯交换反应的反应产物与吸附剂C的接触处理的实施压力没有特殊限制,既可以在减压状态下实施,也可以在加压状态下实施。通常为0.000001~10MPa(绝对压力)。
本发明制造方法中的酯交换反应的反应产物与吸附剂C的接触处理的实施时间根据(甲基)丙烯酸酯的种类、催化剂的种类和使用量、实施温度、接触处理的方式等的不同而不同,通常为0.1~150小时,优选为0.5~80小时。
本发明制造方法中的酯交换反应的反应产物与吸附剂C的接触处理优选进行至含有(甲基)丙烯酸酯的精制处理物中残留的来自催化剂B的锌小于800ppm,更优选进行至小于400ppm,进一步优选进行至小于200ppm,特别优选进行至小于100ppm。
另外,催化剂A为具有氮杂双环结构的环状叔胺或其盐或其配合物、脒或其盐或其配合物、具有吡啶环的化合物或其盐或其配合物、具有叔二胺结构的化合物或其盐或其配合物时,优选进行至来自催化剂A的氮小于200ppm,更优选进行至小于150ppm,进一步优选进行至小于100ppm。
催化剂A为膦或其盐或其配合物时,优选进行至来自催化剂A的磷小于400ppm,更优选进行至小于300ppm,进一步优选进行至小于200ppm。
本发明制造方法中的酯交换反应的反应产物与吸附剂C的接触处理可以通过间歇式、半间歇式、连续式、固化床方式、流化床方式中的任一种方法来实施。作为间歇式的一例,向由本发明的酯交换反应得到的反应产物中、或者从反应产物通过加压过滤回收催化剂成分后的反应产物中添加吸附剂C,在规定的温度和压力下搅拌来进行接触处理。然后,通过过滤操作,分离出作为残渣的吸附剂C,一边向滤液中鼓泡入含氧气体,一边在规定的温度和压力下搅拌,抽出未反应的单官能(甲基)丙烯酸酯,可以得到作为釜底残留的目标的(甲基)丙烯酸酯。
作为固化床方式的一例,可以采用将由本发明的酯交换反应得到的反应产物通过填充有吸附剂C的柱子等的方法来实施。
从由本发明制造方法得到的反应产物中高纯度地获得目标的(甲基)丙烯酸酯,可以实施以下操作:冷却晶析、浓缩晶析等晶析操作,加压过滤、吸滤、离心过滤等过滤操作,单式蒸馏、分馏、分子蒸馏、水蒸汽蒸馏等蒸馏操作;固液提取、液液提取等提取操作;组合有倾析等的分离精制操作。该分离精制操作中可以使用溶剂。另外,可以使用用于中和本发明中使用的催化剂和/或阻聚剂的中和剂、和/或吸附剂C以外的吸附剂、用于分解或除去副产物的酸和/或碱、用于改善色调的活性炭、用于提高过滤效率和过滤速度的硅藻土等。
实施例
以下,举出实施例和比较例,更具体地说明本发明,但本发明并不限定于这些实施例。予以说明,以下中,只要没有特殊说明,“份”表示“质量份”,“%”表示“质量%”,“ppm”表示“质量ppm”。
实施例和比较例中的反应收率通过对伴随酯交换反应进行而副产的一元醇(来自作为原料使用的单官能(甲基)丙烯酸酯)进行定量,使用下述式来计算。予以说明,一元醇的定量使用具备差示折射率检测器的高效液相色谱(色谱柱:日本ウォーターズ株式会社制Atlantis(PartNo.186003748,柱内径4.6mm,柱长度250mm)、溶剂:纯水或10体积%的异丙醇水溶液),采用内标法实施。
反应收率(摩尔%)=伴随酯交换反应进行而副产的一元醇的摩尔数/(用作原料的醇的摩尔数×用作原料的醇分子所具有的醇性羟基数)×100
实施例和比较例中的精制收率通过使用对酯交换反应结束后的反应产物实施蒸馏、晶析、过滤等分离精制操作后得到的含有目标(甲基)丙烯酸酯的精制处理物的质量来计算。
精制收率(%)=含有目标(甲基)丙烯酸酯的精制处理物(份)/(用作原料的醇所具有的醇性羟基全部被(甲基)丙烯酸酯化时生成的(甲基)丙烯酸酯的分子量×用作原料的醇的摩尔数)×100
在实施例和比较例中,目标的(甲基)丙烯酸酯含有在反应产物和精制处理物中的确认使用具备UV检测器的高效液相色谱(色谱柱:日本ウォーターズ株式会社制ACQUITYUPLC BEH C18(Part No.186002350,柱内径2.1mm,柱长度50mm),检测波长:210nm,溶剂:0.03质量%的三氟乙酸水溶液和甲醇的混合溶剂)来进行。
实施例和比较例中含有(甲基)丙烯酸酯的精制处理物中残留的来自催化剂B的锌的定量使用ICP发光分析装置(スペクトロ社制SPECTROARCOS SOP)和ICP质量分析装置(アジレント·テクノロジー社制Agi lent7700s)进行。
另外,催化剂A为具有氮杂双环结构的环状叔胺或其盐或其配合物、脒或其盐或其配合物、具有吡啶环的化合物或其盐或其配合物、具有叔二胺结构的化合物或其盐或其配合物时,来自催化剂A的氮的定量使用微量全氮分析装置(三菱化学アナリテック制TN-2100H)进行。
其中,当醇的骨架中含有氮原子时,由于从微量氮分析装置的结果对来自催化剂A的氮进行定量是困难的,因而使用气相色谱,通过内标法对催化剂A进行定量。
装置:株式会社岛津制作所制GC-1700
检测器:FID
载气:氦气
柱:TC-5(0.32mm ID×30m,0.25μm)
注入温度:250℃
FID温度:250℃
柱温:在80℃保持5分钟后,以10℃/min的速度升温至280℃后,保持8分钟。
注入量:1μL
另外,催化剂A为膦或其盐或其配合物时,来自催化剂A的磷的定量使用ICP发光分析装置(スペクトロ社制SPECTRO ARCOS SOP)进行。
<实施例1>
向安装有搅拌机、温度计、气体导入管、精馏塔和冷凝管的1升烧瓶中装入季戊四醇69.33份(0.51摩尔)、丙烯酸2-甲氧基乙酯690.05份(5.30摩尔)、作为催化剂A的DABCO2.038份(0.018摩尔)、作为催化剂B的乙酸锌3.260份(0.018摩尔)、对苯二酚单甲基醚1.56份(相对于装入原料的总质量,为2036质量ppm),使含氧气体(氧5体积%、氮95体积%)鼓泡入反应液中。一边在反应液温度105~120℃的范围加热搅拌,一边将反应体系内的压力调节至130~760mmHg的范围,将伴随酯交换反应的进行而副产的2-甲氧基乙醇和丙烯酸2-甲氧基乙酯的混合液经由精馏塔和冷凝管而从反应体系中排出。另外,向反应体系中随时追加与该排出液相同质量份的丙烯酸2-甲氧基乙酯。对从反应体系的排出液中含有的2-甲氧基乙醇进行定量,结果,从加热搅拌开始到30小时后,反应收率达到88%,因此,结束反应液的加热,同时,将反应体系内的压力恢复到常压而结束排出(抽出)。
将得到的反应产物冷却至室温,通过加压过滤分离出析出物后,投入作为吸附剂C的硅酸镁(协和化学工业株式会社制キョーワード600(商品名))17.25份,在内温75~105℃的范围内在常压下加热搅拌3小时,进行接触处理。通过加压过滤,分离出含有吸附剂C的固体成分后,一边向滤液中鼓泡入干燥空气,一边在温度70~95℃、压力0.001~100mmHg的范围进行8小时的减压蒸馏,分离出含有未反应的丙烯酸2-甲氧基乙酯的馏出液。使用具备UV检测器的高效液相色谱,进行减压蒸馏后的釜液的组成分析,结果,确认含有季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯作为主要成分。将该釜液视为精制处理物而计算出的精制收率为94%,来自催化剂A的氮的含量为5ppm,来自催化剂B的锌的含量为0.01ppm以下。结果示于表1。
<实施例2>
向安装有搅拌机、温度计、气体导入管、精馏塔和冷凝管的1升烧瓶中装入二季戊四醇86.33份(0.34摩尔)、丙烯酸2-甲氧基乙酯690.05份(5.30摩尔)、作为催化剂A的DABCO4.077份(0.036摩尔)、作为催化剂B的乙酸锌6.520份(0.036摩尔)、对苯二酚单甲基醚1.63份(相对于装入原料的总质量,为2061质量ppm),使含氧气体(氧5体积%、氮95体积%)鼓泡入反应液中。一边在反应液温度120~145℃的范围加热搅拌,一边将反应体系内的压力调整至250~760mmHg的范围,将伴随酯交换反应的进行而副产的2-甲氧基乙醇和丙烯酸2-甲氧基乙酯的混合液经由精馏塔和冷凝管从反应体系中排出。另外,向反应体系中随时追加与该排出液相同质量份的丙烯酸2-甲氧基乙酯。对从反应体系的排出液中含有的2-甲氧基乙醇进行定量,结果,从加热搅拌开始到24小时后,反应收率达到86%,因此,结束反应液的加热,同时,将反应体系内的压力恢复到常压而结束排出。
将得到的反应产物冷却至室温,通过加压过滤分离出析出物后,投入作为吸附剂C的硅酸铝(协和化学工业制キョーワード700(商品名))19.45份,在内温75~105℃的范围内在常压下加热搅拌3小时,进行接触处理。通过加压过滤,分离出含有吸附剂C的固体成分后,一边向滤液中鼓泡入干燥空气,一边在温度70~95℃、压力0.001~100mmHg的范围进行8小时的减压蒸馏,分离出含有未反应的丙烯酸2-甲氧基乙酯的馏出液。使用具有UV检测器的高效液相色谱,进行减压蒸馏后的釜液的组成分析,结果,确认含有二季戊四醇五丙烯酸酯和二季戊四醇六丙烯酸酯作为主要成分。将该釜液视为精制处理物而计算出的精制收率为97%,来自催化剂A的氮的含量为17ppm,来自催化剂B的锌的含量为0.5ppm。结果示于表1。
<实施例3~21、比较例1~10>
改变醇、单官能(甲基)丙烯酸酯、催化剂A、催化剂B和吸附剂C,采用与实施例1~2同样的方法,进行酯交换反应和与吸附剂C的接触处理,得到含有目标(甲基)丙烯酸酯的精制处理物,然后,测定催化剂A或来自催化剂A的氮或磷的含量、以及来自催化剂B的锌的含量。另外,关于使用的醇骨架中含有氮的实施例11-12和比较例5-6,测定残留的催化剂(DABCO)的含量。结果示于表1~8。
予以说明,表中,使用以下缩写。
PET:季戊四醇
MCA:丙烯酸2-甲氧基乙酯
BA:丙烯酸正丁酯
DABCO:三乙二胺
DPET:二季戊四醇
TMP:三羟甲基丙烷
DTMP:双三羟甲基丙烷
GLY:甘油
DIGLY:二甘油
XLY:木糖醇
NMI:N-甲基咪唑
DMAP:N,N-二甲基-4-氨基吡啶
THEIC:三(2-羟乙基)异氰尿酸酯
Zn(acac)2:乙酰丙酮锌
TEA:三乙醇胺
TPP:三苯基膦
GLY1EO:甘油的环氧烷1摩尔加成物(花王株式会社制エマルゲンGE-1AS(商品名)的脱水处理物)
GLYCARBO:1,2-碳酸甘油酯
POLYGLY:聚甘油(平均聚合度6,阪本药品工业株式会社制聚甘油#500)的脱水处理物)
DEGV:二甘醇单乙烯基醚
BzOH:苄醇
MA:丙烯酸甲酯
EA:丙烯酸乙酯
IBA:丙烯酸异丁酯
TMHD:N,N,N',N'-四甲基-1,6-己二胺
KW-600:硅酸镁(2MgO·6SiO2·XH2O,协和化学工业株式会社制キョーワード600(商品名))
KW-700:硅酸铝(Al2O3·9SiO2·XH2O,协和化学工业株式会社制キョーワード700(商品名))
KW-2000:镁-铝复合氧化物(Mg0.7Al0.3O1.15,协和化学工业株式会社制キョーワード2000(商品名))
在本发明的通过吸附剂C进行吸附剂处理的实施例中,与不进行该吸附处理的比较例相比,可以得到精制处理物中含有的来自催化剂的杂质大幅减少、且高品质的(甲基)丙烯酸酯。
产业实用性
根据本发明的方法,可以从醇与单官能(甲基)丙烯酸酯得到来自催化剂的杂质大幅减少的高品质的(甲基)丙烯酸酯。由本发明方法得到的(甲基)丙烯酸酯可作为涂料、油墨、粘接剂、膜、片材、光学透镜等光学用途、填料和成型材料等的配合物的交联成分,或者作为反应性稀释剂成分而适用于各种工业用途。
Claims (10)
1.(甲基)丙烯酸酯的制造方法,其特征在于,包括以下工序:在并用下述催化剂A和下述催化剂B而使醇与单官能(甲基)丙烯酸酯发生酯交换反应来制造(甲基)丙烯酸酯时,对酯交换反应的反应产物进行与下述吸附剂C的接触处理,
催化剂A:选自具有氮杂双环结构的环状叔胺或其盐或其配合物、脒或其盐或其配合物、具有吡啶环的化合物或其盐或其配合物、膦或其盐或其配合物、具有叔二胺结构的化合物或其盐或其配合物中的一种以上化合物,
催化剂B:选自含锌化合物中的一种以上化合物,
吸附剂C:选自含有镁、铝、硅的至少一种的氧化物和氢氧化物中的一种以上化合物。
2.权利要求1所述的(甲基)丙烯酸酯的制造方法,其中,上述醇为具有3个以上醇性羟基的多元醇。
3.权利要求1或2所述的(甲基)丙烯酸酯的制造方法,其中,上述醇为三羟甲基乙烷、三羟甲基丙烷、甘油、甘油的环氧烷加成物、三(2-羟乙基)异氰尿酸酯、三乙醇胺、双三羟甲基乙烷、双三羟甲基丙烷、二甘油、二甘油的环氧烷加成物、季戊四醇、季戊四醇的环氧烷加成物、木糖醇、二季戊四醇、二季戊四醇的环氧烷加成物、D-山梨糖醇、聚甘油中的任一种。
4.权利要求1~3任一项所述的(甲基)丙烯酸酯的制造方法,其中,上述醇为季戊四醇或二季戊四醇。
5.权利要求1~4任一项所述的(甲基)丙烯酸酯的制造方法,其中,上述单官能(甲基)丙烯酸酯为丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸2-甲氧基乙酯中的任一种。
6.权利要求1~5任一项所述的(甲基)丙烯酸酯的制造方法,其中,上述单官能(甲基)丙烯酸酯为丙烯酸2-甲氧基乙酯。
7.权利要求1~6任一项所述的(甲基)丙烯酸酯的制造方法,其中,上述催化剂A为奎宁环、3-羟基奎宁环、三乙二胺、2-(羟甲基)三乙二胺、N-甲基咪唑、N,N,N',N'-四甲基-1,6-己二胺中的任一种。
8.权利要求1~7任一项所述的(甲基)丙烯酸酯的制造方法,其中,上述催化剂B为下述通式(4)或下述通式(5)表示的含锌化合物,
式中,R12和R13可以相同或不同,为碳数1~20的直链或支链状烷基、碳数1~20的直链或支链状烯基、碳数6~24的芳基、或碳数5~20的环烷基,可具有取代基,其中,R12和R13不具有卤原子,
式中,R14、R15、R16、R17、R18和R19可以相同或不同,为碳数1~20的直链或支链状烷基、碳数1~20的直链或支链状烯基、碳数6~24的芳基、或碳数5~20的环烷基,可具有取代基。
9.权利要求1~8任一项所述的(甲基)丙烯酸酯的制造方法,其中,上述催化剂A为三乙二胺,上述催化剂B为上述通式(4)表示的含锌化合物。
10.权利要求1~9任一项所述的(甲基)丙烯酸酯的制造方法,其中,上述吸附剂C为硅酸镁、硅酸铝中的任一种。
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CN111018712A (zh) * | 2019-12-30 | 2020-04-17 | 上海华谊新材料有限公司 | (甲基)丙烯酸酯的生产方法 |
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JP2018150286A (ja) * | 2017-03-15 | 2018-09-27 | 東亞合成株式会社 | (メタ)アクリレートの製造方法 |
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