JP2011506517A - （メタ）アクリレートの製造方法 - Google Patents
（メタ）アクリレートの製造方法 Download PDFInfo
- Publication number
- JP2011506517A JP2011506517A JP2010538506A JP2010538506A JP2011506517A JP 2011506517 A JP2011506517 A JP 2011506517A JP 2010538506 A JP2010538506 A JP 2010538506A JP 2010538506 A JP2010538506 A JP 2010538506A JP 2011506517 A JP2011506517 A JP 2011506517A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- oxygen
- formula
- acrylate
- reaction
- 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.)
- Pending
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 55
- 239000001301 oxygen Substances 0.000 claims abstract description 54
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 40
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 239000003112 inhibitor Substances 0.000 claims abstract description 21
- 239000011541 reaction mixture Substances 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 239000007789 gas Substances 0.000 claims abstract description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- -1 2-ethylhexyl group Chemical group 0.000 claims description 24
- 238000004821 distillation Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 13
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 11
- 229920001519 homopolymer Polymers 0.000 claims description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 9
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 5
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229940043430 calcium compound Drugs 0.000 claims description 2
- 150000001674 calcium compounds Chemical class 0.000 claims description 2
- 150000002642 lithium compounds Chemical class 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 abstract description 4
- 239000002480 mineral oil Substances 0.000 abstract description 4
- 235000010446 mineral oil Nutrition 0.000 abstract description 4
- 239000000284 extract Substances 0.000 abstract description 3
- 239000004908 Emulsion polymer Substances 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 18
- 239000003999 initiator Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 14
- 238000005809 transesterification reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000000084 colloidal system Substances 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000007720 emulsion polymerization reaction Methods 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000000872 buffer Substances 0.000 description 5
- ZMVHTLOQSTVDFE-UHFFFAOYSA-N methanol;methyl 2-methylprop-2-enoate Chemical compound OC.COC(=O)C(C)=C ZMVHTLOQSTVDFE-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-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
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- UJMZZAZBRIPOHZ-UHFFFAOYSA-N 2-ethylhexan-1-ol;titanium Chemical compound [Ti].CCCCC(CC)CO UJMZZAZBRIPOHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 239000012874 anionic emulsifier Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- PTPLXVHPKMTVIW-FPLPWBNLSA-N (Z)-hydroxyimino-oxido-phenylazanium Chemical compound O\N=[N+](/[O-])c1ccccc1 PTPLXVHPKMTVIW-FPLPWBNLSA-N 0.000 description 1
- DTCCVIYSGXONHU-CJHDCQNGSA-N (z)-2-(2-phenylethenyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\C=CC1=CC=CC=C1 DTCCVIYSGXONHU-CJHDCQNGSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- YOIZTLBZAMFVPK-UHFFFAOYSA-N 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound CCOC1=CC(C(O)C(O)=O)=CC=C1O YOIZTLBZAMFVPK-UHFFFAOYSA-N 0.000 description 1
- 125000003890 2-phenylbutyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- AODAQIOEZVDQLS-UHFFFAOYSA-N 3,4-ditert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1C(C)(C)C AODAQIOEZVDQLS-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 229920004894 Triton X-305 Polymers 0.000 description 1
- MIQWEMDDUPSLRW-UHFFFAOYSA-N [O].O=C=O Chemical compound [O].O=C=O MIQWEMDDUPSLRW-UHFFFAOYSA-N 0.000 description 1
- VVTSZOCINPYFDP-UHFFFAOYSA-N [O].[Ar] Chemical compound [O].[Ar] VVTSZOCINPYFDP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical class [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical class [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical class [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical compound O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 239000012875 nonionic emulsifier Substances 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
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- RIPZIAOLXVVULW-UHFFFAOYSA-N pentane-2,4-dione Chemical compound CC(=O)CC(C)=O.CC(=O)CC(C)=O RIPZIAOLXVVULW-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-N peroxydisulfuric acid Chemical class OS(=O)(=O)OOS(O)(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 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
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- 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
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/12—Esters of monohydric alcohols or phenols
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1492707P | 2007-12-19 | 2007-12-19 | |
| PCT/EP2008/062982 WO2009080380A2 (en) | 2007-12-19 | 2008-09-29 | Process for preparing (meth)acrylates |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014190893A Division JP2014237723A (ja) | 2007-12-19 | 2014-09-19 | （メタ）アクリレートの製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2011506517A true JP2011506517A (ja) | 2011-03-03 |
Family
ID=40530354
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010538506A Pending JP2011506517A (ja) | 2007-12-19 | 2008-09-29 | （メタ）アクリレートの製造方法 |
| JP2014190893A Pending JP2014237723A (ja) | 2007-12-19 | 2014-09-19 | （メタ）アクリレートの製造方法 |
| JP2017000518A Pending JP2017088608A (ja) | 2007-12-19 | 2017-01-05 | （メタ）アクリレートの製造方法 |
| JP2020000396A Pending JP2020073555A (ja) | 2007-12-19 | 2020-01-06 | （メタ）アクリレートの製造方法 |
| JP2022035159A Pending JP2022081593A (ja) | 2007-12-19 | 2022-03-08 | （メタ）アクリレートの製造方法 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014190893A Pending JP2014237723A (ja) | 2007-12-19 | 2014-09-19 | （メタ）アクリレートの製造方法 |
| JP2017000518A Pending JP2017088608A (ja) | 2007-12-19 | 2017-01-05 | （メタ）アクリレートの製造方法 |
| JP2020000396A Pending JP2020073555A (ja) | 2007-12-19 | 2020-01-06 | （メタ）アクリレートの製造方法 |
| JP2022035159A Pending JP2022081593A (ja) | 2007-12-19 | 2022-03-08 | （メタ）アクリレートの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US9206270B2 (https=) |
| EP (1) | EP2220023B1 (https=) |
| JP (5) | JP2011506517A (https=) |
| CN (1) | CN101462958B (https=) |
| TW (1) | TWI555728B (https=) |
| WO (1) | WO2009080380A2 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018502832A (ja) * | 2014-12-01 | 2018-02-01 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ヘオノン（メタ）アクリラートを製造する方法 |
| JP2024505499A (ja) * | 2021-01-25 | 2024-02-06 | ベーアーエスエフ・エスエー | ２－エチルヘキシルアクリレートを得るための連続方法 |
| WO2024095957A1 (ja) * | 2022-10-31 | 2024-05-10 | 三菱ケミカル株式会社 | エステル化合物含有組成物及びその製造方法、重合性組成物、（メタ）アクリル系重合体及びその製造方法 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2220023B1 (en) * | 2007-12-19 | 2017-04-05 | Evonik Röhm GmbH | Process for preparing (meth)acrylates |
| US20160090348A1 (en) | 2014-09-30 | 2016-03-31 | Basf Se | Preparation of c8-c24 alkyl (meth)acrylates |
| WO2016071052A1 (de) | 2014-11-05 | 2016-05-12 | Basf Se | Verfahren zur herstellung von c8-c22-alkyl(meth)acrylaten |
| BR112017018072A2 (pt) * | 2015-02-26 | 2018-04-10 | Basf Se | processo para preparação de di(met)acrilato de isossorbida através da transesterificação de (met)acrilato de alquila com isossorbida, e, uso de di(met)acrilato de isossorbida. |
| ES2745682T3 (es) | 2015-02-26 | 2020-03-03 | Basf Se | Procedimiento para la preparación de di(met)acrilato de etoxilato de isosorbida |
| EP3390338A1 (de) | 2015-12-15 | 2018-10-24 | Basf Se | Verfahren zur herstellung von hydroxybenzophenonpolyglykolether-(meth)acrylat |
| WO2018024563A1 (de) | 2016-08-05 | 2018-02-08 | Basf Se | Polyisobutengruppen tragende makromonomere und deren homo- oder copolymere |
| WO2023143939A1 (de) | 2022-01-26 | 2023-08-03 | Basf Se | Lagerung und/oder transport ethylenisch ungesättigter verbindungen |
| EP4293010A1 (en) * | 2022-06-15 | 2023-12-20 | Evonik Operations GmbH | Process for the discontinuous (trans)esterification of (meth)acrylate compounds |
| WO2023242259A1 (en) * | 2022-06-15 | 2023-12-21 | Evonik Operations Gmbh | Method for increasing reaction performance by intermediate removal of side product holdup |
| EP4299155A1 (en) * | 2022-06-27 | 2024-01-03 | Evonik Operations GmbH | Process to precisely calculate the raw material demand of intermediate batches within a production campaign |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1149810A (ja) * | 1997-06-06 | 1999-02-23 | Nippon Shokubai Co Ltd | 高分子量ポリマーおよびその製造方法並びにドラッグレデューサ |
| JPH11246479A (ja) * | 1998-02-27 | 1999-09-14 | Nissei Kagaku Kogyo Kk | メタクリル酸シクロヘキシルの製造方法 |
| JP2000198835A (ja) * | 1999-01-05 | 2000-07-18 | Daicel Chem Ind Ltd | ヒドロキシアルキル（メタ）アクリラ―ト・メチル置換ε―カプロラクトン変性物含有組成物の製造方法 |
| JP2000319225A (ja) * | 1999-04-28 | 2000-11-21 | Mitsubishi Rayon Co Ltd | メタクリル酸アルキルエステルの製造方法 |
| JP2001089415A (ja) * | 1999-08-27 | 2001-04-03 | Roehm Gmbh | ジ（メタ）アクリル酸エステルの製造法 |
| JP2002169220A (ja) * | 2000-11-30 | 2002-06-14 | Mamiya Op Co Ltd | カメラのストラップ用吊金具 |
| JP2004269417A (ja) * | 2003-03-07 | 2004-09-30 | Mitsubishi Rayon Co Ltd | （メタ）アクリル酸エステルの製造方法 |
| WO2005040088A1 (ja) * | 2003-10-24 | 2005-05-06 | Mitsubishi Rayon Co., Ltd. | (メタ)アクリル酸エステルの製造方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3423443A1 (de) | 1984-06-26 | 1986-01-02 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von estern der acryl- und methacrylsaeure durch umesterung |
| BR9106344A (pt) | 1990-04-16 | 1993-04-20 | Minnesota Mining & Mfg | Composicao para limpeza de pele |
| JP3081707B2 (ja) * | 1992-06-16 | 2000-08-28 | ダイセル化学工業株式会社 | メタクリル酸グリシジルの製造方法 |
| JP3513209B2 (ja) * | 1994-03-30 | 2004-03-31 | 積水化学工業株式会社 | 熱可塑性ポリウレタン |
| JPH0931018A (ja) * | 1995-07-24 | 1997-02-04 | Dainippon Ink & Chem Inc | ペンタエリスリトール（メタ）アクリルエステル類の製造法 |
| JPH10175919A (ja) * | 1996-12-18 | 1998-06-30 | Daicel Chem Ind Ltd | （メタ）アクリル酸テトラヒドロベンジルの製造法 |
| JPH10175918A (ja) * | 1996-12-18 | 1998-06-30 | Daicel Chem Ind Ltd | （メタ）アクリル酸テトラヒドロベンジルの製造方法 |
| EP0882739A3 (en) | 1997-06-06 | 1999-04-07 | Nippon Shokubai Co., Ltd. | High molecular weight polymer and producing method the same and drag reducer |
| JPH1180082A (ja) * | 1997-09-10 | 1999-03-23 | Kao Corp | （メタ）アクリル酸高級アルキルエステルの製造法 |
| BR0107038A (pt) * | 2000-08-08 | 2002-06-04 | Kaneka Corp | Composição de resina de cloreto de vinilo expansìvel |
| EP1201641B1 (en) | 2000-10-23 | 2013-08-14 | Nippon Shokubai Co., Ltd. | Composition of vinyl ether group containing (meth)acrylic acid ester and production method thereof |
| DE10301902A1 (de) * | 2003-01-17 | 2003-12-04 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| JP2006104168A (ja) | 2004-10-08 | 2006-04-20 | Osaka Organic Chem Ind Ltd | （メタ）アクリル酸エステルの製造法 |
| JP2006169220A (ja) | 2004-12-20 | 2006-06-29 | Osaka Organic Chem Ind Ltd | （メタ）アクリル酸エステルの製造法 |
| US7285582B2 (en) * | 2004-12-30 | 2007-10-23 | Conocophillips Company | Modified latex drag reducer and processes therefor and therewith |
| US7361628B2 (en) * | 2004-12-30 | 2008-04-22 | Conocophillips Company | Remote delivery of latex drag-reducing agent without introduction of immiscible low-viscosity flow facilitator |
| TW200728270A (en) * | 2005-11-21 | 2007-08-01 | Toagosei Co Ltd | The manufacture method of (meta) acrylic esters |
| EP2220023B1 (en) * | 2007-12-19 | 2017-04-05 | Evonik Röhm GmbH | Process for preparing (meth)acrylates |
-
2008
- 2008-09-29 EP EP08804845.9A patent/EP2220023B1/en active Active
- 2008-09-29 JP JP2010538506A patent/JP2011506517A/ja active Pending
- 2008-09-29 US US12/745,703 patent/US9206270B2/en active Active
- 2008-09-29 WO PCT/EP2008/062982 patent/WO2009080380A2/en not_active Ceased
- 2008-12-16 TW TW097148967A patent/TWI555728B/zh active
- 2008-12-17 CN CN200810185589.1A patent/CN101462958B/zh active Active
-
2014
- 2014-09-19 JP JP2014190893A patent/JP2014237723A/ja active Pending
-
2015
- 2015-10-27 US US14/924,018 patent/US9688601B2/en active Active
-
2017
- 2017-01-05 JP JP2017000518A patent/JP2017088608A/ja active Pending
-
2020
- 2020-01-06 JP JP2020000396A patent/JP2020073555A/ja active Pending
-
2022
- 2022-03-08 JP JP2022035159A patent/JP2022081593A/ja active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1149810A (ja) * | 1997-06-06 | 1999-02-23 | Nippon Shokubai Co Ltd | 高分子量ポリマーおよびその製造方法並びにドラッグレデューサ |
| JPH11246479A (ja) * | 1998-02-27 | 1999-09-14 | Nissei Kagaku Kogyo Kk | メタクリル酸シクロヘキシルの製造方法 |
| JP2000198835A (ja) * | 1999-01-05 | 2000-07-18 | Daicel Chem Ind Ltd | ヒドロキシアルキル（メタ）アクリラ―ト・メチル置換ε―カプロラクトン変性物含有組成物の製造方法 |
| JP2000319225A (ja) * | 1999-04-28 | 2000-11-21 | Mitsubishi Rayon Co Ltd | メタクリル酸アルキルエステルの製造方法 |
| JP2001089415A (ja) * | 1999-08-27 | 2001-04-03 | Roehm Gmbh | ジ（メタ）アクリル酸エステルの製造法 |
| JP2002169220A (ja) * | 2000-11-30 | 2002-06-14 | Mamiya Op Co Ltd | カメラのストラップ用吊金具 |
| JP2004269417A (ja) * | 2003-03-07 | 2004-09-30 | Mitsubishi Rayon Co Ltd | （メタ）アクリル酸エステルの製造方法 |
| WO2005040088A1 (ja) * | 2003-10-24 | 2005-05-06 | Mitsubishi Rayon Co., Ltd. | (メタ)アクリル酸エステルの製造方法 |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018502832A (ja) * | 2014-12-01 | 2018-02-01 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ヘオノン（メタ）アクリラートを製造する方法 |
| JP2024505499A (ja) * | 2021-01-25 | 2024-02-06 | ベーアーエスエフ・エスエー | ２－エチルヘキシルアクリレートを得るための連続方法 |
| JP7778798B2 (ja) | 2021-01-25 | 2025-12-02 | ベーアーエスエフ・エスエー | ２－エチルヘキシルアクリレートを得るための連続方法 |
| WO2024095957A1 (ja) * | 2022-10-31 | 2024-05-10 | 三菱ケミカル株式会社 | エステル化合物含有組成物及びその製造方法、重合性組成物、（メタ）アクリル系重合体及びその製造方法 |
| JPWO2024095957A1 (https=) * | 2022-10-31 | 2024-05-10 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2014237723A (ja) | 2014-12-18 |
| US20160046556A1 (en) | 2016-02-18 |
| US20100280205A1 (en) | 2010-11-04 |
| EP2220023A2 (en) | 2010-08-25 |
| JP2017088608A (ja) | 2017-05-25 |
| US9206270B2 (en) | 2015-12-08 |
| EP2220023B1 (en) | 2017-04-05 |
| TWI555728B (zh) | 2016-11-01 |
| JP2022081593A (ja) | 2022-05-31 |
| WO2009080380A3 (en) | 2009-09-17 |
| US9688601B2 (en) | 2017-06-27 |
| WO2009080380A2 (en) | 2009-07-02 |
| CN101462958A (zh) | 2009-06-24 |
| CN101462958B (zh) | 2016-01-20 |
| TW200946496A (en) | 2009-11-16 |
| JP2020073555A (ja) | 2020-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017088608A (ja) | （メタ）アクリレートの製造方法 | |
| EP1061063A1 (en) | Method of producing carboxylic acid and alcohol | |
| US6451380B1 (en) | Reactive coalescents | |
| KR102572781B1 (ko) | 이소소르비드 디(메트)아크릴레이트의 제조 방법 | |
| JP2014237723A5 (https=) | ||
| EP0542877B1 (en) | Polymerisation of vinyl monomers with a new catalytic system | |
| WO2006049474A1 (en) | Method for producing an (meth)acrylate syrup | |
| CN1266420A (zh) | 防止(甲基)丙烯酸酯有不希望的自由基聚合的稳定化方法 | |
| EP4021911B1 (en) | Preparation of an aqueous dispersion of acrylate-siloxane copolymer particles | |
| CN108752199B (zh) | (甲基)丙烯酸类化合物的制备方法 | |
| CN101092478A (zh) | 一种制备烷基聚氧乙烯醚丙烯酸酯或烷基聚氧乙烯醚甲基丙烯酸酯的方法 | |
| CN104945255A (zh) | 一种甲基丙烯酸环己酯的制备方法 | |
| WO2012121836A1 (en) | Synergistic polymerization inhibitor composition and method | |
| US20090018360A1 (en) | Process for preparation of alkyl and alcoxyalkyl-alpha-cyanoacrylates by depolymerisation of poly(alkyl-alpha cyanoacrylates) or poly(alcoxyalkyl-alpha-cyanoacrylates) and its usage as technical and/or medical adhesive | |
| WO2015099915A1 (en) | Inhibitor combination for lithium salt-catalyzed transesterification process and method for removing lithium salt | |
| JP3779777B2 (ja) | メタクリル系樹脂の製造方法 | |
| KR101178238B1 (ko) | 공비적 에스테르화에 의한 알킬 아크릴레이트의 제조방법 | |
| JP2002155021A (ja) | ビニル単量体用重合防止剤組成物及び高純度（メタ）アクリル酸の製造方法 | |
| US7981255B2 (en) | Method for producing (meth)acrylic acid and (meth)acrylic esters | |
| CN100548961C (zh) | 一种生产(甲基)丙烯酸和(甲基)丙烯酸酯的新方法 | |
| JP2009510191A5 (https=) | ||
| EP1106593A2 (en) | A composition comprising a vinyl reactive coalescent | |
| JP2010043020A (ja) | （メタ）アクリル酸エステルの重合防止方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20101228 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110831 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130424 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130603 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130902 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130909 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131001 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131008 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131031 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20140519 |