DE10127938A1 - Verfahren zur Herstellung von (Meth)acrylsäureestern - Google Patents
Verfahren zur Herstellung von (Meth)acrylsäureesternInfo
- Publication number
- DE10127938A1 DE10127938A1 DE10127938A DE10127938A DE10127938A1 DE 10127938 A1 DE10127938 A1 DE 10127938A1 DE 10127938 A DE10127938 A DE 10127938A DE 10127938 A DE10127938 A DE 10127938A DE 10127938 A1 DE10127938 A1 DE 10127938A1
- Authority
- DE
- Germany
- Prior art keywords
- meth
- acrylic acid
- transesterification
- basic
- mixture
- 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.)
- Withdrawn
Links
- 150000001252 acrylic acid derivatives Chemical class 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title abstract description 17
- 230000032050 esterification Effects 0.000 title abstract description 5
- 238000005886 esterification reaction Methods 0.000 title abstract description 5
- 239000006185 dispersion Substances 0.000 title description 5
- 239000000853 adhesive Substances 0.000 title description 2
- 230000001070 adhesive effect Effects 0.000 title description 2
- 229920001577 copolymer Polymers 0.000 title description 2
- 239000003973 paint Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 46
- 238000004821 distillation Methods 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 23
- 239000011541 reaction mixture Substances 0.000 claims abstract description 15
- 238000012545 processing Methods 0.000 claims abstract description 9
- 239000011261 inert gas Substances 0.000 claims abstract description 8
- 238000005809 transesterification reaction Methods 0.000 claims description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- 239000007789 gas Substances 0.000 claims description 24
- 239000010936 titanium Substances 0.000 claims description 17
- 238000000926 separation method Methods 0.000 claims description 16
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 15
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 15
- 229950000688 phenothiazine Drugs 0.000 claims description 15
- 230000006641 stabilisation Effects 0.000 claims description 14
- 238000011105 stabilization Methods 0.000 claims description 14
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 13
- 229910052719 titanium Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 7
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical group CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000010626 work up procedure Methods 0.000 claims description 2
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical group CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 235000019441 ethanol Nutrition 0.000 description 32
- 239000000047 product Substances 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 13
- -1 vinyloxy Chemical group 0.000 description 13
- 238000010992 reflux Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006845 Michael addition reaction Methods 0.000 description 9
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 238000010926 purge Methods 0.000 description 9
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical group CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 8
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000003990 capacitor Substances 0.000 description 8
- 229960002887 deanol Drugs 0.000 description 8
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- 241000589614 Pseudomonas stutzeri Species 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000002034 butanolic fraction Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229960004337 hydroquinone Drugs 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 1
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical class CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 1
- UVSPBAFXKQMDBG-UHFFFAOYSA-N 2-(dimethylamino)ethyl propanoate Chemical compound CCC(=O)OCCN(C)C UVSPBAFXKQMDBG-UHFFFAOYSA-N 0.000 description 1
- PBKGYWLWIJLDGZ-UHFFFAOYSA-N 2-(dimethylamino)propan-1-ol Chemical compound OCC(C)N(C)C PBKGYWLWIJLDGZ-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- NBTXFNJPFOORGI-UHFFFAOYSA-N 2-ethenoxyethyl prop-2-enoate Chemical compound C=COCCOC(=O)C=C NBTXFNJPFOORGI-UHFFFAOYSA-N 0.000 description 1
- QUVMSYUGOKEMPX-UHFFFAOYSA-N 2-methylpropan-1-olate;titanium(4+) Chemical group [Ti+4].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-] QUVMSYUGOKEMPX-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- DMPODMBXLRMZSP-UHFFFAOYSA-N 3-(dibutylamino)propan-1-ol Chemical compound CCCCN(CCCC)CCCO DMPODMBXLRMZSP-UHFFFAOYSA-N 0.000 description 1
- WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 1
- MEPYMUOZRROULQ-UHFFFAOYSA-N 4-tert-butyl-2,6-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1O MEPYMUOZRROULQ-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- BOECYDPVUKJZCS-UHFFFAOYSA-N 6-(dibutylamino)hexan-1-ol Chemical compound CCCCN(CCCC)CCCCCCO BOECYDPVUKJZCS-UHFFFAOYSA-N 0.000 description 1
- YLNQOWCLZJQJLN-UHFFFAOYSA-N 6-(diethylamino)hexan-1-ol Chemical compound CCN(CC)CCCCCCO YLNQOWCLZJQJLN-UHFFFAOYSA-N 0.000 description 1
- QCXNXRUTKSIZND-UHFFFAOYSA-N 6-(dimethylamino)hexan-1-ol Chemical compound CN(C)CCCCCCO QCXNXRUTKSIZND-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000978750 Havardia Species 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 108700001094 Plant Genes Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- OURRXQUGYQRVML-AREMUKBSSA-N [4-[(2s)-3-amino-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl]phenyl]methyl 2,4-dimethylbenzoate Chemical compound CC1=CC(C)=CC=C1C(=O)OCC1=CC=C([C@@H](CN)C(=O)NC=2C=C3C=CN=CC3=CC=2)C=C1 OURRXQUGYQRVML-AREMUKBSSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical group [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical group 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 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
- 239000007788 liquid Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical group CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical group [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- DPNUIZVZBWBCPB-UHFFFAOYSA-J titanium(4+);tetraphenoxide Chemical class [Ti+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 DPNUIZVZBWBCPB-UHFFFAOYSA-J 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/20—Power plant
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/22—Accessories
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/90—Particular type of heating
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10127938A DE10127938A1 (de) | 2001-06-08 | 2001-06-08 | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| EP02758206A EP1490326B1 (de) | 2001-06-08 | 2002-05-28 | Verfahren zur herstellung von (meth) acrylsaeureestern |
| DE50214843T DE50214843D1 (de) | 2001-06-08 | 2002-05-28 | Verfahren zur herstellung von (meth) acrylsaeureestern |
| PCT/EP2002/005818 WO2002100817A2 (de) | 2001-06-08 | 2002-05-28 | Verfahren zur herstellung von (meth) acrylsaeureestern |
| US10/479,962 US7294240B2 (en) | 2001-06-08 | 2002-05-28 | Method for producing (meth)acrylic acid esters |
| JP2003503587A JP2005506958A (ja) | 2001-06-08 | 2002-05-28 | （メタ）アクリル酸エステルの製造法 |
| AT02758206T ATE493380T1 (de) | 2001-06-08 | 2002-05-28 | Verfahren zur herstellung von (meth) acrylsaeureestern |
| CNB028115376A CN1235869C (zh) | 2001-06-08 | 2002-05-28 | (甲基)丙烯酸酯的制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10127938A DE10127938A1 (de) | 2001-06-08 | 2001-06-08 | Verfahren zur Herstellung von (Meth)acrylsäureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10127938A1 true DE10127938A1 (de) | 2002-07-25 |
Family
ID=7687687
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10127938A Withdrawn DE10127938A1 (de) | 2001-06-08 | 2001-06-08 | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE50214843T Expired - Lifetime DE50214843D1 (de) | 2001-06-08 | 2002-05-28 | Verfahren zur herstellung von (meth) acrylsaeureestern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50214843T Expired - Lifetime DE50214843D1 (de) | 2001-06-08 | 2002-05-28 | Verfahren zur herstellung von (meth) acrylsaeureestern |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7294240B2 (https=) |
| EP (1) | EP1490326B1 (https=) |
| JP (1) | JP2005506958A (https=) |
| CN (1) | CN1235869C (https=) |
| AT (1) | ATE493380T1 (https=) |
| DE (2) | DE10127938A1 (https=) |
| WO (1) | WO2002100817A2 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI253636B (en) * | 2003-11-19 | 2006-04-21 | Mediatek Inc | Apparatus with switching servo gain and offset for optical disk device and method thereof |
| DE10354652A1 (de) | 2003-11-22 | 2005-07-07 | Clariant Gmbh | Verfahren zur Veresterung von Alkoholen mit olefinisch ungesättigten Carbonsäuren |
| JP2006182606A (ja) * | 2004-12-28 | 2006-07-13 | Miyoshi Oil & Fat Co Ltd | セメント混和剤及びセメント組成物 |
| KR100786945B1 (ko) | 2005-08-11 | 2007-12-17 | 주식회사 엘지화학 | (메타)아크릴 에스테르의 제조 방법 |
| DE102008040221A1 (de) * | 2008-07-07 | 2010-01-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| FR2941452B1 (fr) * | 2009-01-27 | 2011-02-11 | Arkema France | Procede de purification de la fraction azeotropique generee lors de la synthese de l'acrylate de n,n-dimethyl aminoethyle |
| CA2811363A1 (en) * | 2010-09-23 | 2012-03-29 | Basf Se | Process for preparing (meth)acrylic esters of n,n-substituted amino alcohols |
| JP5289490B2 (ja) * | 2011-03-18 | 2013-09-11 | 株式会社日本触媒 | エーテル基を有する（メタ）アクリル酸エステルの製造方法 |
| RU2497802C1 (ru) * | 2012-04-24 | 2013-11-10 | Закрытое акционерное общество "Химтэк Инжиниринг" | Способ получения диметиламиноэтилакрилата |
| CN102850155B (zh) * | 2012-09-24 | 2015-07-08 | 上海和创化学股份有限公司 | 甲基丙烯酸酯类产品的制备方法 |
| KR101984280B1 (ko) | 2015-11-27 | 2019-05-30 | 주식회사 엘지화학 | (메트)아크릴산의 제조 방법 |
| FR3050731B1 (fr) | 2016-04-28 | 2018-04-20 | Arkema France | Composition d'acrylate de n,n-dimethyl aminoethyle stabilisee vis-a-vis de la coloration |
| FR3069538B1 (fr) | 2017-07-25 | 2020-05-15 | Arkema France | Procede de purification d'esters (meth)acryliques. |
| FR3086658B1 (fr) | 2018-10-02 | 2021-10-15 | Arkema France | Stabilisation de (meth)acrylates d'aminoalkyle |
| BR102020022314A2 (pt) * | 2020-10-30 | 2022-05-10 | Oxiteno S.A. Indústria E Comércio | Processo para a preparação de poliacrilatos alcoxilados funcionais, poliacrilatos alcoxilados funcionais, e, uso dos mesmos |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1067806B (de) | 1954-09-09 | 1959-10-29 | Roehm & Haas Gmbh | Verfahren zur kontinuierlichen Herstellung von Estern der Acryl- und Methacrylsaeuremit hoehermolekularen Alkoholen |
| US2832800A (en) | 1956-01-23 | 1958-04-29 | Rohm & Haas | Reesterification alcoholysis |
| DE1248943C2 (de) * | 1965-07-20 | 1974-03-07 | Basf Ag | Verfahren und Vorrichtung zur diskontinuierlichen Entfernung von Geruchs-stoffen auswaessrigen Polymerisatdispersionen |
| FR2033441A5 (https=) | 1969-02-25 | 1970-12-04 | Ugilor | |
| BE787750A (fr) * | 1971-08-20 | 1973-02-19 | Union Carbide Corp | Procede pour inhiber la polymerisation d'acrylates et methacrylates pendant leur distillation |
| GB1573071A (en) | 1977-02-10 | 1980-08-13 | Mitsubishi Rayon Co | Process for producing unsaturated carbocylic acid esters |
| US4147721A (en) * | 1978-04-06 | 1979-04-03 | Halcon Research And Development Corporation | Process for recovering methacrylic acid |
| US4260821A (en) * | 1979-03-15 | 1981-04-07 | Halcon Research And Development Corp. | Minimizing polymerization during recovery of methacrylic acid |
| US4698440A (en) * | 1983-09-14 | 1987-10-06 | E. I. Du Pont De Nemours And Company | Process for making n-butyl methacrylate |
| GB8410497D0 (en) | 1984-04-25 | 1984-05-31 | Allied Colloids Ltd | Synthesis of vinyl esters |
| FR2617840B1 (fr) | 1987-07-08 | 1989-09-01 | Charbonnages Ste Chimique | Procede de fabrication de (meth)acrylate de dialkylaminoalkyle |
| DE3843854A1 (de) | 1988-12-24 | 1990-06-28 | Henkel Kgaa | Verfahren zur verbesserten herstellung von (meth)acrylsaeureestern mehrwertiger alkohole (i) |
| JPH0713050B2 (ja) | 1989-09-26 | 1995-02-15 | 東亞合成株式会社 | ジメチルアミノエチルアクリレートの製造方法 |
| DE4019788A1 (de) | 1990-06-21 | 1992-01-02 | Henkel Kgaa | Verfahren zur herstellung von mehrfunktionellen (meth)acrylsaeureestern |
| DE69807406T2 (de) * | 1997-10-01 | 2003-04-24 | Nippon Shokubai Co. Ltd., Osaka | Verfahren zur Herstellung von Alkylamino-(meth)Acrylat und eine Vorrichtung dafür |
| DE19814529A1 (de) * | 1998-04-01 | 1999-10-07 | Basf Ag | Polyalkylenarylate mit hohem Carbonylendgruppengehalt |
| FR2777561B1 (fr) | 1998-04-21 | 2000-06-02 | Atochem Elf Sa | Procede de fabrication en continu de (meth)acrylates de dialkylaminoalkyle |
| EP0965593B2 (en) * | 1998-06-19 | 2008-12-03 | Shin-Etsu Chemical Co., Ltd. | Distillation of (meth)acryloxybearing alkoxysilane |
| US6482976B1 (en) * | 1999-06-17 | 2002-11-19 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
| DE10063175A1 (de) * | 2000-12-18 | 2002-06-20 | Basf Ag | Verfahren zur Herstellung von höheren (Meth)acrylsäureestern |
| DE10127939A1 (de) | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE10127941A1 (de) * | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
-
2001
- 2001-06-08 DE DE10127938A patent/DE10127938A1/de not_active Withdrawn
-
2002
- 2002-05-28 JP JP2003503587A patent/JP2005506958A/ja active Pending
- 2002-05-28 CN CNB028115376A patent/CN1235869C/zh not_active Expired - Lifetime
- 2002-05-28 AT AT02758206T patent/ATE493380T1/de active
- 2002-05-28 WO PCT/EP2002/005818 patent/WO2002100817A2/de not_active Ceased
- 2002-05-28 DE DE50214843T patent/DE50214843D1/de not_active Expired - Lifetime
- 2002-05-28 EP EP02758206A patent/EP1490326B1/de not_active Expired - Lifetime
- 2002-05-28 US US10/479,962 patent/US7294240B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE50214843D1 (de) | 2011-02-10 |
| EP1490326A2 (de) | 2004-12-29 |
| CN1592734A (zh) | 2005-03-09 |
| US20040168903A1 (en) | 2004-09-02 |
| WO2002100817A2 (de) | 2002-12-19 |
| CN1235869C (zh) | 2006-01-11 |
| EP1490326B1 (de) | 2010-12-29 |
| WO2002100817A3 (de) | 2004-10-21 |
| US7294240B2 (en) | 2007-11-13 |
| JP2005506958A (ja) | 2005-03-10 |
| ATE493380T1 (de) | 2011-01-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE10127938A1 (de) | Verfahren zur Herstellung von (Meth)acrylsäureestern | |
| WO2003055837A1 (de) | Verfahren zur kontinuierlichen herstellung von alkyl(meth)acrylaten | |
| DE19604267A1 (de) | Verfahren zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure | |
| EP2294048B1 (de) | Verfahren zur herstellung von (meth)acrylsäureestern | |
| DE19536178A1 (de) | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure | |
| DE10301007A1 (de) | Verbessertes Verfahren zur kontinuierlichen Herstellung von Alkyl(meth)acrylaten mit mehrfacher Katalysatorrezyklierung. | |
| EP2903961A1 (de) | Kontinuierliches verfahren zur herstellung von (meth)acrylaten von c10-alkoholgemischen | |
| EP1129061A1 (de) | Verfahren zur kontinuierlichen herstellung von alkylestern der (meth)acrylsäure | |
| DD295627A5 (de) | Verfahren zur kontinuierlichen Herstellung von niedrigsiedenden Acrylaten | |
| DE69807406T2 (de) | Verfahren zur Herstellung von Alkylamino-(meth)Acrylat und eine Vorrichtung dafür | |
| EP3277657B1 (de) | Herstellung von tert-butylestern aliphatischer carbonsäuren | |
| WO2002050014A1 (de) | Verfahren zur herstellung von höheren (meth)acrylsäureestern | |
| EP1399409B1 (de) | Verfahren zur herstellung von (meth)acrylsäureestern | |
| EP1305276B1 (de) | Verfahren zur herstellung von tert.-c4-c8-alkylestern der (meth)acrylsäure und darin verwandter fallfilmverdampfer | |
| EP2427421B1 (de) | Verfahren zur aufreinigung von monomeren | |
| EP2619173B1 (de) | Verfahren zur herstellung von (meth)acrylsäureestern von n,n-substituierten aminoalkoholen | |
| EP4015498B1 (de) | Verfahren zur kontinuierlichen herstellung von acrylsäure-n-butylester | |
| WO1998031656A1 (de) | Verfahren zum verestern von (meth)acrylsäure mit einem alkanol | |
| DE10246869B4 (de) | Verfahren zur Herstellung von (Meth)acrylsäureestern | |
| EP0365777B1 (de) | Verfahren zur Herstellung von hochsiedenden Acrylaten bzw. Methacrylaten | |
| DE19851984A1 (de) | Verfahren zum Verestern von (Meth)acrylsäure mit einem Alkanol | |
| DE10063510A1 (de) | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylacrylaten | |
| DE102005006974A1 (de) | Kontinuierliches Verfahren zur Herstellung von Cyclohexyl(meth)acrylat | |
| WO2002085834A1 (de) | Verfahren zur reinigung eines organischen lösungsmittels zur absorption von maleinsäureanhydrid | |
| EP2421908A1 (de) | Verfahren zur herstellung von (meth)acrylsäureestern von polyalkoxygruppen enthaltenden alkoholen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAV | Publication of unexamined application with consent of applicant | ||
| 8130 | Withdrawal |