JP6273539B2 - 多官能(メタ)アクリレートの製造方法 - Google Patents
多官能(メタ)アクリレートの製造方法 Download PDFInfo
- Publication number
- JP6273539B2 JP6273539B2 JP2016513668A JP2016513668A JP6273539B2 JP 6273539 B2 JP6273539 B2 JP 6273539B2 JP 2016513668 A JP2016513668 A JP 2016513668A JP 2016513668 A JP2016513668 A JP 2016513668A JP 6273539 B2 JP6273539 B2 JP 6273539B2
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- Prior art keywords
- acrylate
- meth
- group
- catalyst
- polyfunctional
- 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.)
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims description 76
- 238000004519 manufacturing process Methods 0.000 title claims description 39
- 239000003054 catalyst Substances 0.000 claims description 81
- -1 cyclic tertiary amine Chemical class 0.000 claims description 56
- 150000005846 sugar alcohols Polymers 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 17
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000011701 zinc Substances 0.000 claims description 16
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 229910052725 zinc Inorganic materials 0.000 claims description 14
- 230000001476 alcoholic effect Effects 0.000 claims description 13
- 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 11
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 11
- 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 claims description 10
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 239000004246 zinc acetate Substances 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 235000011187 glycerol Nutrition 0.000 claims description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 6
- 229940105990 diglycerin Drugs 0.000 claims description 6
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 6
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 claims description 5
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 5
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 5
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- 150000001409 amidines Chemical class 0.000 claims description 5
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- BMFMTNROJASFBW-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfinyl)acetic acid Chemical compound OC(=O)CS(=O)CC1=CC=CO1 BMFMTNROJASFBW-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
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
- 239000000811 xylitol Substances 0.000 claims description 3
- 235000010447 xylitol Nutrition 0.000 claims description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 3
- 229960002675 xylitol Drugs 0.000 claims description 3
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 claims description 3
- 229960002920 sorbitol Drugs 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 49
- 238000005809 transesterification reaction Methods 0.000 description 17
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000012973 diazabicyclooctane Substances 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000011403 purification operation Methods 0.000 description 5
- 239000012264 purified product Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000005587 bubbling Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000012778 molding material Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 2
- SIXFVXJMCGPTRB-KSSYENDESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxane-3,4,5-triol Chemical compound C1=CC(OC)=CC=C1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 SIXFVXJMCGPTRB-KSSYENDESA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- ZBRADJBKOUALEI-UHFFFAOYSA-N 1,3-diazabicyclo[5.2.0]nonane Chemical compound C1NCCCC2CCN21 ZBRADJBKOUALEI-UHFFFAOYSA-N 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- PBYMYAJONQZORL-UHFFFAOYSA-N 1-methylisoquinoline Chemical compound C1=CC=C2C(C)=NC=CC2=C1 PBYMYAJONQZORL-UHFFFAOYSA-N 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- MFEIKQPHQINPRI-UHFFFAOYSA-N 3-Ethylpyridine Chemical compound CCC1=CC=CN=C1 MFEIKQPHQINPRI-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-methylquinoline Chemical compound C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
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- JVZRCNQLWOELDU-UHFFFAOYSA-N 4-Phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical compound C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 description 2
- LUYISICIYVKBTA-UHFFFAOYSA-N 6-methylquinoline Chemical compound N1=CC=CC2=CC(C)=CC=C21 LUYISICIYVKBTA-UHFFFAOYSA-N 0.000 description 2
- KDYVCOSVYOSHOL-UHFFFAOYSA-N 7-methylquinoline Chemical compound C1=CC=NC2=CC(C)=CC=C21 KDYVCOSVYOSHOL-UHFFFAOYSA-N 0.000 description 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical compound C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
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- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
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Description
当該多官能(メタ)アクリレートとしては、トリメチロールプロパントリ(メタ)アクリレート、グリセリントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジトリメチロールプロパンテトラ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、トリペンタエリスリトールオクタ(メタ)アクリレートなどが知られている。
エステル化反応による多官能(メタ)アクリレートの製造では、触媒として硫酸、パラトルエンスルホン酸、メタンスルホン酸などのスルホン酸が使用されるが、エステル化反応終了後に得られる反応粗生成物から該スルホン酸を除去するために、アルカリ水溶液で抽出洗浄を行う必要があり、工程が煩雑になり生産性の低下が著しい。また、該抽出操作において目的の多官能アクリレートの一部がけん化されることにより、収率が低下するという問題がある。
しかし、これらの触媒を使用する方法は、得られる多官能(メタ)アクリレートの収率は高いものの、触媒の有害性の観点から、製品への触媒の残留を極力低減するための精製操作を行わなければならず、特にアルコール性水酸基を3個以上有する多価アルコールを原料に(メタ)アクリロイル基を3個以上有する多官能(メタ)アクリレートを製造する場合、該多官能(メタ)アクリレートの蒸気圧は極めて低いために蒸留により留出成分として精製取得することが困難であることから、液液抽出などの精製操作を複数回施さなければならず、工程が煩雑になり生産性の低下が著しい(特許文献1参照)。また、精製にともない発生する廃棄物の無害化に高額な費用を必要とすることがあり、経済的に有利な製造方法であるとは言い難い。
触媒A:アザビシクロ構造を有する環状3級アミン又はその塩若しくは錯体、アミジン又はその塩若しくは錯体、ピリジン環を有する化合物又はその塩若しくは錯体からなる群から選ばれる一種以上の化合物。
触媒B:亜鉛を含む化合物からなる群から選ばれる一種以上の化合物。
触媒A:アザビシクロ構造を有する環状3級アミン又はその塩若しくは錯体、アミジン又はその塩若しくは錯体、ピリジン環を有する化合物又はその塩若しくは錯体からなる群から選ばれる一種以上の化合物。
触媒B:後記一般式(2)及び下記一般式(3)で表される亜鉛を含む化合物からなる群から選ばれる一種以上の化合物。
以下、本発明を詳細に説明する。
2個のアルコール性水酸基を有する2価アルコールの具体例としては、エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、トリメチレングリコール、ジプロピレングリコール、トリプロピレングリコール、ポリプロピレングリコール、ブタンジオール、ペンタンジオール、ヘキサンジオール、ヘプタンジオール、ノナンジオール、ネオペンチルグリコール、シクロヘキサンジオール、シクロヘキサンジメタノール、ジオキサングリコール、N−メチルジエタノールアミン、N−エチルジエタノールアミン、N−ブチルジエタノールアミン、N−tert−ブチルジエタノールアミン、N−ラウリルジエタノールアミン、ステアリルジエタノールアミン、N−フェニルジエタノールアミン、m−トリルジエタノールアミン、p−トリルジエタノールアミン、N,N’−ビス(2−ヒドロキシプロピル)アニリン、N−ニトロソジエタノールアミン、N−(2−ヒドロキシエチル)ラクトアミド、N,N'−ビス(2−ヒドロキシエチル)オキサミド、3−モルホリノ−1,2−プロパンジオール、2,6−ピリジンジメタノール、3−(ジメチルアミノ)−1,2−プロパンジオール、3−(ジエチルアミノ)−1,2−プロパンジオール、アロキサンチン二水和物、(+)−N,N,N',N'−テトラメチル−L−酒石酸ジアミド、(−)−N,N,N',N'−テトラメチル−D−酒石酸ジアミド、N−プロピル−N−(2,3−ジヒドロキシプロピル)ペルフルオロ−n−オクチルスルホンアミド、チミジン、クロラムフェニコール、チアンフェニコール、D−エリスロノラクトン、メチル4,6−O−ベンジリデン−α−D−グルコピラノシド、フェニル4,6−O−ベンジリデン−1−チオ−β−D−グルコピラノシド、1,2:5,6−ジ−O−イソプロピリデン−D−マンニトール、1,2−O−イソプロピリデン−α−D−キシロフラノース、2,6−ジ−O−パルミトイル−L−アスコルビン酸、イソソルビド及びこれらのアルキレンオキサイド付加物、さらにはハイドロキノン、ビスフェノールA、ビスフェノールAP、ビスフェノールAF、ビスフェノールB、ビスフェノールBP、ビスフェノールC、ビスフェノールE、ビスフェノールF、ビスフェノールG、ビスフェノールM、ビスフェノールS、チオビスフェノール、ビスフェノールP、ビスフェノールPH、ビスフェノールTMC及びビスフェノールZなどのフェノール性水酸基を有する化合物のアルキレンオキサイド付加物などが挙げられる。
4個のアルコール性水酸基を有する4価アルコールの具体例としては、ジトリメチロールエタン、ジトリメチロールプロパン、ジグリセリン、ペンタエリスリトール、N,N,N',N'−テトラキス(2−ヒドロキシエチル)ブタンジアミド、N,N,N',N'−テトラキス(2−ヒドロキシプロピル)ブタンジアミド、N,N,N',N'−テトラキス(2−ヒドロキシエチル)ヘキサンジアミド、N,N,N',N'−テトラキス(2−ヒドロキシプロピル)ヘキサンジアミド、N,N,N',N'−テトラキス(2−ヒドロキシエチル)エチレンジアミン、N,N,N',N'−テトラキス(2−ヒドロキシプロピル)エチレンジアミン、N−ヘキサノイル−D−グルコサミン、N−バレリル−D−グルコサミン、N−トリフルオロアセチル−D−グルコサミン、N−ベンゾイル−D−グルコサミン、5−アセトアミド−N,N’−ビス(2,3−ジヒドロキシプロピル)−2,4,6−トリヨードイソフタルアミド、スピラマイシン、クラリスロマイシン、ロイコマイシンA1、ロイコマイシンA5、ロイコマイシンA7、ロイコマイシンA9、ロイコマイシンA13、リンコマイシン塩酸塩一水和物、ジアゾリジニル尿素、D−(−)−アラビノース、DL−アラビノース、L−(+)−アラビノース、meso−エリトリトール、D−(+)−フコース、L−(−)−フコース、アリルα−D−ガラクトピラノシド、メチルβ−D−ガラクトピラノシド、メチルα−D−ガラクトピラノシド一水和物、4−メトキシフェニルβ−D−ガラクトピラノシド、2−ニトロフェニルβ−D−ガラクトピラノシド、4−ニトロフェニルα−D−ガラクトピラノシド、4−ニトロフェニルβ−D−ガラクトピラノシド、フェニルβ−D−ガラクトピラノシド、N−アセチル−D−ガラクトサミン水和物、D−(+)−ガラクトサミン塩酸塩、アルブチン、2−デオキシ−D−グルコース、エスクリン1.5水和物、D−(+)−グルコノ−1,5−ラクトン、D−グルクロンアミド、ヘリシン、メチルα−D−グルコピラノシド、メチルβ−D−グルコピラノシド0.5水和物、4−メトキシフェニルβ−D−グルコピラノシド、4−ニトロフェニルβ−D−グルコピラノシド一水和物、4−ニトロフェニルα−D−グルコピラノシド、ノニルβ−D−グルコピラノシド、n−オクチルβ−D−グルコピラノシド、フェニルβ−D−グルコピラノシド水和物、フロリジン水和物、ピセイド、プエラリン、N−アセチル−D−グルコサミン、N−ベンゾイル−D−グルコサミン、D−(+)−グルコサミン塩酸塩、N−ヘキサノイル−D−グルコサミン、N−バレリル−D−グルコサミン、L−(+)−グロン酸γ−ラクトン、D−(−)−リキソース、L−(+)−リキソース、3,4−O−イソプロピリデン−D−マンニトール、メチルα−D−マンノピラノシド、D−マンノノ−1,4−ラクトン、4−メトキシフェニルα−D−マンノピラノシド、N−アセチル−D−マンノサミン一水和物、D−(−)−リボース、L−リボース、D−(+)−キシロース、DL−キシロース、L−(−)−キシロース、D−アラボアスコルビン酸、L−アスコルビン酸、L−トレイトール及びこれらのアルキレンオキサイド付加物などが挙げられる。
5個のアルコール性水酸基を有する5価アルコールの具体例としては、トリトリメチロールエタン、トリトリメチロールプロパン、トリグリセリン、ビス(2−ヒドロキシエチル)アミノトリス(ヒドロキシメチル)メタン、ビス(2−ヒドロキシプロピル)アミノトリス(ヒドロキシメチル)メタン、N,N,N',N'',N''−ペンタキス(2−ヒドロキシエチル)ジエチレントリアミン、N,N,N',N'',N''−ペンタキス(2−ヒドロキシプロピル)ジエチレントリアミン、ミグリトール、エリスロマイシン、アジスロマイシン二水和物、D−(+)−アラビトール、DL−アラビトール、L−(−)−アラビトール、D−(−)−フルクトース、L−(+)−フルクトース、D−(+)−ガラクトース、L−(−)−ガラクトース、β−D−グルコース、D−(+)−グルコース、L−(−)−グルコース、D−グルコースジエチルメルカプタール、サリシン、L−グロース、D−(+)−マンノース、L−(−)−マンノース、リビトール、L−(−)−ソルボース、D−タガトース、キシリトール、スクラロース、アスコルビン酸グリセリル及びこれらのアルキレンオキサイド付加物などが挙げられる。
6個以上のアルコール性水酸基を有する多価アルコールの具体例としては、ポリトリメチロールエタン、ポリトリメチロールプロパン、ポリグリセリン、ジペンタエリスリトール、トリペンタエリスリトール、ポリペンタエリスリトール、イオヘキソール、ガラクチトール、D−ソルビトール、L−ソルビトール、myo−イノシトール、scyllo−イノシトール、D−マンニトール、L−マンニトール、イカリイン、アミグダリン、D−(+)−セロビオース、ジオスミン、2−O−α−D−グルコピラノシル−L−アスコルビン酸、ヘスペリジン、D−(+)−ラクトース一水和物、ラクツロース、D−(+)−マルトース一水和物、D−(+)−メリビオース一水和物、メチルヘスペリジン、マルチトール、ナリンギン水和物、ネオヘスペリジンジヒドロカルコン水和物、パラチノース水和物、ルチン水和物、D−(+)−スクロース、ステビオシド、D−(+)−ツラノース、D−(+)−トレハロース (無水)、D−(+)−トレハロース二水和物、D−(+)−メレチトース水和物、D−(+)−ラフィノース五水和物、レバウジオシドA、スタキオース、α−シクロデキストリン、β−シクロデキストリン、γ−シクロデキストリン、デンプン及びこれらのアルキレンオキサイド付加物などが挙げられる。
これらの多価アルコールの中で、本発明では、3個以上のアルコール性水酸基を有する多価アルコールを使用し、特にトリメチロールエタン、トリメチロールプロパン、グリセリン、グリセリンのアルキレンオキサイド付加物、トリス(2-ヒロドキシエチル)イソシアヌレート、トリエタノールアミン、ジトリメチロールエタン、ジトリメチロールプロパン、ジグリセリン、ジグリセリンのアルキレンオキサイド付加物、ペンタエリスリトール、ペンタエリスリトールのアルキレンオキサイド付加物、キシリトール、ジペンタエリスリトール、ジペンタエリスリトールのアルキレンオキサイド付加物、D−ソルビトールが好ましい。
なお、これらの多価アルコールについて、その水和物又は溶媒和物が存在する場合には、該水和物及び溶媒和物も本発明の製造方法における多価アルコールとして使用できる。
上記アザビシクロ構造を有する環状3級アミン又はその塩若しくは錯体の具体例としては、1−アザビシクロ[1,1,0]ブタン、1,3−ジアザビシクロ[1,1,0]ブタン、1−アザビシクロ[2,1,0]ヘプタン、1,3−ジアザビシクロ[2,1,0]ヘプタン、1,4−ジアザビシクロ[2,1,0]ヘプタン、1−アザビシクロ[2,2,0]ヘキサン、1,3−ジアザビシクロ[2,2,0]ヘキサン、1−アザビシクロ[2,1,1]ヘキサン、1,3−ジアザビシクロ[2,1,1]ヘキサン、1−アザビシクロ[2,2,1]ヘプタン、1,3−ジアザビシクロ[2,2,1]ヘプタン、1,4−ジアザビシクロ[2,2,1]ヘプタン、1−アザビシクロ[3,2,0]ヘプタン、1,3−ジアザビシクロ[3,2,0]ヘプタン、1,4−ジアザビシクロ[3,2,0]ヘプタン、1,6−ジアザビシクロ[3,2,0]ヘプタン、1,3−ジアザビシクロ[2,2,2]オクタン、1−アザビシクロ[3,2,1]オクタン、1,3−ジアザビシクロ[3,2,1]オクタン、1,4−ジアザビシクロ[3,2,1]オクタン、1,5−ジアザビシクロ[3,2,1]オクタン、1,6−ジアザビシクロ[3,2,1]オクタン、1−アザビシクロ[4,1,1]オクタン、1,3−ジアザビシクロ[4,1,1]オクタン、1,4−ジアザビシクロ[4,1,1]オクタン、1,5−ジアザビシクロ[4,1,1]オクタン、1,6−ジアザビシクロ[4,1,1]オクタン、1,7−ジアザビシクロ[4,1,1]オクタン、1−アザビシクロ[4,2,0]オクタン、1,3−ジアザビシクロ[4,2,0]オクタン、1,4−ジアザビシクロ[4,2,0]オクタン、1,5−ジアザビシクロ[4,2,0]オクタン、1,7−ジアザビシクロ[4,2,0]オクタン、1−アザビシクロ[3,3,1]ノナン、1,3−ジアザビシクロ[3,3,1]ノナン、1,4−ジアザビシクロ[3,3,1]ノナン、1,5−ジアザビシクロ[3,3,1]ノナン、1−アザビシクロ[3,2,2]ノナン、1,3−ジアザビシクロ[3,2,2]ノナン、1,4−ジアザビシクロ[3,2,2]ノナン、1,5−ジアザビシクロ[3,2,2]ノナン、1,6−ジアザビシクロ[3,2,2]ノナン、1,8−ジアザビシクロ[3,2,2]ノナン、1−アザビシクロ[4,3,0]ノナン、1,3−ジアザビシクロ[4,3,0]ノナン、1,4−ジアザビシクロ[4,3,0]ノナン、1,5−ジアザビシクロ[4,3,0]ノナン、1,6−ジアザビシクロ[4,3,0]ノナン、1,7−ジアザビシクロ[4,3,0]ノナン、1,8−ジアザビシクロ[4,3,0]ノナン、1−アザビシクロ[4,2,1]ノナン、1,3−ジアザビシクロ[4,2,1]ノナン、1,4−ジアザビシクロ[4,2,1]ノナン、1,5−ジアザビシクロ[4,2,1]ノナン、1,6−ジアザビシクロ[4,2,1]ノナン、1,7−ジアザビシクロ[4,2,1]ノナン、1−アザビシクロ[5,2,0]ノナン、1,3−ジアザビシクロ[5,2,0]ノナン、1,3−ジアザビシクロ[5,2,0]ノナン、1,4−ジアザビシクロ[5,2,0]ノナン、1,5−ジアザビシクロ[5,2,0]ノナン、1,6−ジアザビシクロ[5,2,0]ノナン、1,7−ジアザビシクロ[5,2,0]ノナン、1,8−ジアザビシクロ[5,2,0]ノナン、1−アザビシクロ[5,1,1]ノナン、1,3−アザビシクロ[5,1,1]ノナン、1,4−アザビシクロ[5,1,1]ノナン、1,5−アザビシクロ[5,1,1]ノナン、1,6−アザビシクロ[5,1,1]ノナン、1,7−アザビシクロ[5,1,1]ノナン、1−アザビシクロ[6,1,0]ノナン、1,3−ジアザビシクロ[6,1,0]ノナン、1,4−ジアザビシクロ[6,1,0]ノナン、1,5−ジアザビシクロ[6,1,0]ノナン、1,6−ジアザビシクロ[6,1,0]ノナン、1,7−ジアザビシクロ[6,1,0]ノナン、1,8−ジアザビシクロ[6,1,0]ノナン、1−アザビシクロ[7,1,0]デカン、1,9−ジアザビシクロ[7,1,0]デカン、1−アザビシクロ[6,2,0]デカン、1,8−ジアザビシクロ[6,2,0]デカン、1−アザビシクロ[6,1,1]デカン、1,8−ジアザビシクロ[6,1,1]デカン、1−アザビシクロ[5,3,0]デカン、1,7−ジアザビシクロ[5,3,0]デカン、1−アザビシクロ[5,2,1]デカン、1,7−ジアザビシクロ[5,2,1]デカン、1−アザビシクロ[4,3,1]デカン、1,6−ジアザビシクロ[4,3,1]デカン、1−アザビシクロ[4,2,2]デカン、1,6−ジアザビシクロ[4,2,2]デカン、1−アザビシクロ[5,4,0]ウンデカン、1,7−ジアザビシクロ[5,4,0]ウンデカン、1−アザビシクロ[5.3.1]ウンデカン、1,7−ジアザビシクロ[5,3,1]ウンデカン、1−アザビシクロ[5,2,2]ウンデカン、1,7−ジアザビシクロ[5,2,2]ウンデカン、1−アザビシクロ[4,4,1]ウンデカン、1,7−ジアザビシクロ[4,4,1]ウンデカン、1−アザビシクロ[4,3,2]ウンデカン、1,7−ジアザビシクロ[4,3,2]ウンデカン、1−アザビシクロ[3,3,0]オクタン、1−アザビシクロ[4,3,0]ノナン、キヌクリジン、ルピナン、ルピニン、キノリジジン、3−ヒドロキシキヌクリジン、3−キヌクリジノン、キンコリン、キンコリジン、シンコニジン、シンコニン、キニジン、キニン、クプレイン、イボガイン、スワインソニン、カスタノスペルミン、ミアンセリン、ミルタザピン、カナジン、トレーガー塩基、1−アザビシクロ[2,2,2]オクタン−3−カルボン酸、トリエチレンジアミン(別名DABCO)、ヘキサメチレンテトラミン、3−キノリジノン塩酸塩、3−クロロ−1−アザビシクロ[2,2,2]オクタン塩酸塩、シンコニジン二塩酸塩、シンコニン塩酸塩水和物、シンコニジン硫酸塩二水和物、ヒドロキニジン塩酸塩、シンコニン硫酸塩二水和物、キニン塩酸塩二水和物、硫酸キニーネ二水和物、キニンリン酸塩、キニジン硫酸塩二水和物、ミアンセリン塩酸塩、1,1'−(ブタン−1,4−ジイル)ビス[4−アザ−1−アゾニアビシクロ[2,2,2]オクタン]ジブロミド、1,1'−(デカン−1,10−ジイル)ビス[4−アザ−1−アゾニアビシクロ[2,2,2]オクタン]ジブロミド、ビス(トリメチルアルミニウム)−1,4−ジアザビシクロ[2,2,2]オクタン付加物、ビスムチン、キヌクリジン塩酸塩、キヌクリジノン塩酸塩、3−ヒドロキシキヌクリジン塩酸塩、DABCO塩酸塩、キヌクリジン酢酸塩、キヌクリジノン酢酸塩、3−ヒドロキシキヌクリジン酢酸塩、DABCO酢酸塩、キヌクリジンアクリル酸塩、キヌクリジノンアクリル酸塩、3−ヒドロキシキヌクリジンアクリル酸塩、DABCOアクリル酸塩などが挙げられる。
反応収率(モル%)=エステル交換反応の進行に伴い副生した1価アルコールのモル数/(原料として使用した多価アルコールのモル数×多価アルコール分子の有する水酸基数)×100
精製収率(%)=多官能(メタ)アクリレートを含む精製処理物(部)/(原料として使用した多価アルコールの有する水酸基が全て(メタ)アクリレート化された場合に生成する多官能(メタ)アクリレートの分子量×原料として使用した多価アルコールのモル数)×100
回転子、温度計、ガス導入管、冷却管を取付けた20ミリリットルの試験管に、ペンタエリスリトールを0.533部(0.0039モル)、2−メトキシエチルアクリレートを5.308部(0.0408モル)、触媒Aとしてキヌクリジンを0.016部(0.0001モル)、触媒Bとして酢酸亜鉛を0.025部(0.0001モル)、ハイドロキノンモノメチルエーテルを0.012部(仕込んだ原料の総重量に対して2036wtppm)仕込み、含酸素ガス(酸素を5容量%、窒素を95容量%)を液中にバブリングさせながら反応液温度105〜120℃の範囲で加熱還流を5時間行った。その後、該反応液に含まれるエステル交換反応の進行に伴い副生した2−メトキシエタノールを定量した結果、反応収率は48%であった。UV検出器を備えた高速液体クロマトグラフを用いて該反応液に含まれる反応生成物の組成分析を行った結果、ペンタエリスリトールジアクリレート、ペンタエリスリトールトリアクリレート及びペンタエリスリトールテトラアクリレートを主要成分として含むことを確認した。
多価アルコール、単官能(メタ)アクリレート、触媒A、触媒B、反応温度及び反応時間をかえ、実施例1と同様の方法でエステル交換反応を行い、反応収率を算出した。結果を表1〜表7に示す。なお、表中においては、以下の略号を使用した。
PET:ペンタエリスリトール
MCA:2−メトキシエチルアクリレート
QD:キヌクリジン
Zn(OAc)2:酢酸亜鉛
HQD:3−ヒドロキシキヌクリジン
DABCO:トリエチレンジアミン
NMI:N−メチルイミダゾール
DBU:1,8−ジアザビシクロ[5,4,0]ウンデカ−7−エン
DBN:1,5−ジアザビシクロ[4,3,0]ノナ−5−エン
DMAP:N,N−ジメチル−4−アミノピリジン
Zn(acac)2:亜鉛アセチルアセトナート
DPET:ジペンタエリスリトール
DTMP:ジトリメチロールプロパン
GLY:グリセリン
THEIC:トリス(2-ヒロドキシエチル)イソシアヌレート
DIGLY:ジグリセリン
PET−4EO:ペンタエリスリトールのエチレンオキサイド付加物(水酸基価717mgKOH/g)
DPET−6PO:ジペンタエリスリトールのエチレンオキサイド付加物(水酸基価643mgKOH/g)
TMHD:N,N,N',N'−テトラメチル−1,6−ヘキサンジアミン
BA:n−ブチルアクリレート
TEA:トリエタノールアミン
撹拌機、温度計、ガス導入管、精留塔及び冷却管を取付けた1リットルのフラスコに、ペンタエリスリトールを69.33部(0.51モル)、2−メトキシエチルアクリレートを690.05部(5.30モル)、触媒AとしてDABCOを2.04部(0.02モル)、触媒Bとして酢酸亜鉛を3.26部(0.02モル)、ハイドロキノンモノメチルエーテルを1.56部(仕込んだ原料の総重量に対して2036wtppm)仕込み、含酸素ガス(酸素を5容量%、窒素を95容量%)を液中にバブリングさせた。反応液温度105〜120℃の範囲で加熱撹拌させながら、反応系内の圧力を130〜760mmHgの範囲で調整し、エステル交換反応の進行に伴い副生した2−メトキシエタノールと2−メトキシエチルアクリレートの混合液を精留塔及び冷却管を介して反応系から抜出した。また、該抜出液と同重量部の2−メトキシエチルアクリレートを反応系に随時追加した。反応系からの抜出液に含まれる2−メトキシエタノールを定量した結果、加熱撹拌開始から30時間後に反応収率は88%に到達したので、反応液の加熱を終了するとともに、反応系内の圧力を常圧に戻して抜出を終了した。反応液を室温まで冷却して析出物3.89部をろ過分離した後、ろ液に乾燥空気をバブリングさせながら、温度70〜95℃、圧力0.001〜100mmHgの範囲で8時間の減圧蒸留を行い、未反応の2−メトキシエチルアクリレートを含む留出液を分離した。UV検出器を備えた高速液体クロマトグラフを用いて減圧蒸留後の釜液の組成分析を行った結果、ペンタエリスリトールトリアクリレート及びペンタエリスリトールテトラアクリレートを主要成分として含むことを確認した。該釜液を精製処理物とみなして算出した精製収率は96%であった。結果を表8に示す。
撹拌機、温度計、ガス導入管、精留塔及び冷却管を取付けた1リットルのフラスコに、ジペンタエリスリトールを86.33部(0.34モル)、2−メトキシエチルアクリレートを690.05部(5.30モル)、触媒AとしてDABCOを4.08部(0.04モル)、触媒Bとして酢酸亜鉛を6.52部(0.04モル)、ハイドロキノンモノメチルエーテルを1.63部(仕込んだ原料の総重量に対して2061wtppm)仕込み、含酸素ガス(酸素を5容量%、窒素を95容量%)を液中にバブリングさせた。反応液温度120〜145℃の範囲で加熱撹拌させながら、反応系内の圧力を250〜760mmHgの範囲で調整し、エステル交換反応の進行に伴い副生した2−メトキシエタノールと2−メトキシエチルアクリレートの混合液を精留塔及び冷却管を介して反応系から抜出した。また、該抜出液と同重量部の2−メトキシエチルアクリレートを反応系に随時追加した。反応系からの抜出液に含まれる2−メトキシエタノールを定量した結果、加熱撹拌開始から24時間後に反応収率は86%に到達したので、反応液の加熱を終了するとともに、反応系内の圧力を常圧に戻して抜出を終了した。反応液を室温まで冷却して析出物8.38部をろ過分離した後、ろ液に乾燥空気をバブリングさせながら、温度70〜95℃、圧力0.001〜100mmHgの範囲で8時間の減圧蒸留を行い、未反応の2−メトキシエチルアクリレートを含む留出液を分離した。UV検出器を備えた高速液体クロマトグラフを用いて減圧蒸留後の釜液の組成分析を行った結果、ジペンタエリスリトールペンタアクリレート及びジペンタエリスリトールヘキサアクリレートを主要成分として含むことを確認した。該釜液を精製処理物とみなして算出した精製収率は99%であった。結果を表8に示す。
Claims (9)
- 3個以上のアルコール性水酸基を有する多価アルコールと単官能(メタ)アクリレートをエステル交換反応させて、多官能(メタ)アクリレートを製造するに際し、下記触媒A及び触媒Bを併用することを特徴とする多官能(メタ)アクリレートの製造方法。
触媒A:アザビシクロ構造を有する環状3級アミン又はその塩若しくは錯体、アミジン又はその塩若しくはその錯体、ピリジン環を有する化合物又はその塩若しくは錯体からなる群から選ばれる一種以上の化合物。
触媒B:下記一般式(2)及び下記一般式(3)で表される亜鉛を含む化合物からなる群から選ばれる一種以上の化合物。
- 多価アルコールがトリメチロールエタン、トリメチロールプロパン、グリセリン、グリセリンのアルキレンオキサイド付加物、トリス(2-ヒロドキシエチル)イソシアヌレート、トリエタノールアミン、ジトリメチロールエタン、ジトリメチロールプロパン、ジグリセリン、ジグリセリンのアルキレンオキサイド付加物、ペンタエリスリトール、ペンタエリスリトールのアルキレンオキサイド付加物、キシリトール、ジペンタエリスリトール、ジペンタエリスリトールのアルキレンオキサイド付加物、D−ソルビトールのいずれかである請求項1に記載の多官能(メタ)アクリレートの製造方法。
- 多価アルコールがペンタエリスリトール又はジペンタエリスリトールである請求項1又は請求項2に記載の多官能(メタ)アクリレートの製造方法。
- 単官能(メタ)アクリレートがメチルアクリレート、エチルアクリレート、n−ブチルアクリレート、i−ブチルアクリレート、2−メトキシエチルアクリレートのいずれかである請求項1〜請求項3のいずれかに記載の多官能(メタ)アクリレートの製造方法。
- 単官能(メタ)アクリレートが2−メトキシエチルアクリレートである請求項1〜請求項4のいずれかに記載の多官能(メタ)アクリレートの製造方法。
- 触媒Aがキヌクリジン、3−ヒドロキシキヌクリジン、トリエチレンジアミン、N−メチルイミダゾール、1,8−ジアザビシクロ[5,4,0]ウンデカ−7−エン、N,N−ジメチル−4−アミノピリジンのいずれかである請求項1〜請求項5のいずれかに記載の多官能(メタ)アクリレートの製造方法。
- 触媒Bが酢酸亜鉛、プロピオン酸亜鉛、アクリル酸亜鉛、メタクリル酸亜鉛、亜鉛アセチルアセトナートのいずれかである請求項1〜請求項6のいずれかに記載の多官能(メタ)アクリレートの製造方法。
- 触媒Aがトリエチレンジアミンであり、触媒Bが酢酸亜鉛である請求項1〜請求項7のいずれかに記載の多官能(メタ)アクリレートの製造方法。
- 3個以上のアルコール性水酸基を有する多価アルコールと単官能(メタ)アクリレートをエステル交換反応させて、多官能(メタ)アクリレートを製造するに際し、前記触媒A及び触媒Bを併用し、
3個以上のアルコール性水酸基を有する多価アルコールの水酸基1モルに対して、触媒Aを0.0001〜0.5モル使用し、触媒Bを0.0001〜0.5モル使用し、
触媒Bの1モルに対して触媒Aを0.005〜10.0モル使用する
請求項1〜請求項8のいずれかに記載の多官能(メタ)アクリレートの製造方法。
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JP6424532B2 (ja) * | 2014-09-17 | 2018-11-21 | 東洋インキScホールディングス株式会社 | フルフリルメタクリレートの製造方法 |
JP6643546B2 (ja) * | 2015-03-10 | 2020-02-12 | 東亞合成株式会社 | (メタ)アクリレートの製造方法 |
KR102567098B1 (ko) * | 2015-04-10 | 2023-08-14 | 도아고세이가부시키가이샤 | (메트)아크릴레이트의 제조 방법 |
WO2017002964A1 (ja) * | 2015-07-02 | 2017-01-05 | 東亞合成株式会社 | 硬化型組成物 |
WO2017002961A1 (ja) * | 2015-07-02 | 2017-01-05 | 東亞合成株式会社 | 硬化型組成物 |
JP6852298B2 (ja) * | 2015-08-21 | 2021-03-31 | 東亞合成株式会社 | インクジェットインキ用硬化型組成物 |
JP6733411B2 (ja) * | 2015-08-21 | 2020-07-29 | 東亞合成株式会社 | 賦型材料用硬化型組成物 |
US20180237629A1 (en) * | 2015-08-21 | 2018-08-23 | Toagosei Co., Ltd. | Curable composition |
JPWO2017033611A1 (ja) * | 2015-08-24 | 2018-06-14 | 東亞合成株式会社 | 多官能(メタ)アクリレートの製造方法 |
TW201829537A (zh) * | 2016-07-29 | 2018-08-16 | 日商東亞合成股份有限公司 | 硬化型組成物 |
JP6849397B2 (ja) * | 2016-11-02 | 2021-03-24 | 三洋化成工業株式会社 | 光硬化性樹脂組成物 |
WO2018092785A1 (ja) * | 2016-11-17 | 2018-05-24 | 東亞合成株式会社 | 活性エネルギー線硬化型組成物 |
TWI796324B (zh) * | 2017-03-09 | 2023-03-21 | 日商東亞合成股份有限公司 | (甲基)丙烯酸酯的製造方法 |
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CN107673959B (zh) * | 2017-10-27 | 2019-10-11 | 西南化工研究设计院有限公司 | 一种制备甲基庚烯酮的方法和系统 |
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US11214714B2 (en) * | 2018-05-08 | 2022-01-04 | Iowa State University Research Foundation, Inc. | Thermoplastic poly acrylated glycerol adhesives useful in cellulosic products |
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