CN1127745A - Process for producing alkyl acrylate or methacrylate - Google Patents
Process for producing alkyl acrylate or methacrylate Download PDFInfo
- Publication number
- CN1127745A CN1127745A CN 95101716 CN95101716A CN1127745A CN 1127745 A CN1127745 A CN 1127745A CN 95101716 CN95101716 CN 95101716 CN 95101716 A CN95101716 A CN 95101716A CN 1127745 A CN1127745 A CN 1127745A
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- Prior art keywords
- formula
- stopper
- ester
- reaction
- catalyzer
- Prior art date
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- Granted
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- 238000000034 method Methods 0.000 title claims abstract description 19
- 230000008569 process Effects 0.000 title description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title 1
- 125000005250 alkyl acrylate group Chemical group 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 238000004821 distillation Methods 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract 3
- -1 nitroxyl free radical Chemical class 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 7
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- 238000005194 fractionation Methods 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 10
- 238000006116 polymerization reaction Methods 0.000 abstract description 8
- 239000003112 inhibitor Substances 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 3
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 238000010526 radical polymerization reaction Methods 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 125000005907 alkyl ester group Chemical group 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- 208000012839 conversion disease Diseases 0.000 description 3
- NFHRNKANAAGQOH-UHFFFAOYSA-N triphenylstannane Chemical compound C1=CC=CC=C1[SnH](C=1C=CC=CC=1)C1=CC=CC=C1 NFHRNKANAAGQOH-UHFFFAOYSA-N 0.000 description 3
- GQEAMFCDHPUBGV-GRHBHMESSA-N (z)-but-2-enedioic acid;dibutyltin Chemical compound OC(=O)\C=C/C(O)=O.CCCC[Sn]CCCC GQEAMFCDHPUBGV-GRHBHMESSA-N 0.000 description 2
- GQPBCYLRCQDVJU-KWZUVTIDSA-N (z)-but-2-enedioic acid;dioctyltin Chemical compound OC(=O)\C=C/C(O)=O.CCCCCCCC[Sn]CCCCCCCC GQPBCYLRCQDVJU-KWZUVTIDSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical class C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 150000003818 basic metals Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- MACVNMKPAKPZQG-UHFFFAOYSA-N dioctyltin(2+);methanolate Chemical compound CCCCCCCC[Sn](OC)(OC)CCCCCCCC MACVNMKPAKPZQG-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- GTJVPLGQFHDOAC-UHFFFAOYSA-N C(C(=O)O)(=O)O.C(CCCCCCC)[Sn]CCCCCCCC Chemical compound C(C(=O)O)(=O)O.C(CCCCCCC)[Sn]CCCCCCCC GTJVPLGQFHDOAC-UHFFFAOYSA-N 0.000 description 1
- JVWKQNPNGKZYHQ-UHFFFAOYSA-N C(CCC)[Sn](CCCC)CCCC.C(C=C/C(=O)O)(=O)O Chemical compound C(CCC)[Sn](CCCC)CCCC.C(C=C/C(=O)O)(=O)O JVWKQNPNGKZYHQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- CWZDBKIRKXOWMJ-UHFFFAOYSA-J [Sn+4].C(CCCCCCC)P(CCCCCCCC)CCCCCCCC.C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-] Chemical compound [Sn+4].C(CCCCCCC)P(CCCCCCCC)CCCCCCCC.C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-] CWZDBKIRKXOWMJ-UHFFFAOYSA-J 0.000 description 1
- GFQNMBFPVLNTRF-UHFFFAOYSA-N [Sn].C(CCC)OCCCCCCCCP(CCCCCCCC)CCCCCCCC Chemical compound [Sn].C(CCC)OCCCCCCCCP(CCCCCCCC)CCCCCCCC GFQNMBFPVLNTRF-UHFFFAOYSA-N 0.000 description 1
- FBNWZKCYNRBNQB-UHFFFAOYSA-N [Sn].C(CCCCCCC)P(CCCCCCCC)CCCCCCCC.C(CCCCCCCCCCCCCCCCC)(=O)O Chemical compound [Sn].C(CCCCCCC)P(CCCCCCCC)CCCCCCCC.C(CCCCCCCCCCCCCCCCC)(=O)O FBNWZKCYNRBNQB-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DEAZKSQKCMTFOZ-UHFFFAOYSA-N butoxy(tributyl)stannane Chemical compound CCCCO[Sn](CCCC)(CCCC)CCCC DEAZKSQKCMTFOZ-UHFFFAOYSA-N 0.000 description 1
- GQOZKVXJDFPLCX-UHFFFAOYSA-N butoxy(triphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(OCCCC)C1=CC=CC=C1 GQOZKVXJDFPLCX-UHFFFAOYSA-N 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- ZNZBASDDVBURLC-UHFFFAOYSA-N dibutyl(diethoxy)stannane Chemical compound CCCC[Sn](OCC)(OCC)CCCC ZNZBASDDVBURLC-UHFFFAOYSA-N 0.000 description 1
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- QLCGFUKTPZHCND-UHFFFAOYSA-N diethoxy(dioctyl)stannane Chemical compound CCCCCCCC[Sn](OCC)(OCC)CCCCCCCC QLCGFUKTPZHCND-UHFFFAOYSA-N 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- BJNOPMHCHZPZJT-UHFFFAOYSA-N octadecanoic acid;tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCCCCCCCCCCCCCCCC(O)=O BJNOPMHCHZPZJT-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Catalyzer repeats the reuse number of times | Reaction conversion ratio | Product yield (%) | Product purity (%) | Reaction times h |
????1 | ????99.8 | ????95.5 | ????99.2 | ????4.0 |
????2 | ????99.7 | ????97.0 | ????99.4 | ????4.0 |
????3 | ????99.6 | ????96.5 | ????99.2 | ????4.2 |
????4 | ????99.5 | ????96.0 | ????99.3 | ????3.7 |
????5 | ????99.6 | ????96.0 | ????99.5 | ????3.4 |
????6 | ????99.7 | ????97.0 | ????99.3 | ????4.0 |
????7 | ????99.7 | ????96.5 | ????99.2 | ????4.0 |
????8 | ????99.5 | ????96.3 | ????99.4 | ????4.0 |
????9 | ????99.7 | ????97.0 | ????99.2 | ????3.7 |
???10 | ????99.5 | ????96.8 | ????99.3 | ????4.0 |
Embodiment | Raw alcohol | Reaction times (h) | Product yield (%) |
????2 | Propyl carbinol | ????4.0 | ????95.0 |
????3 | Dodecyl alcohol | ????3.0 | ????97.5 |
????4 | Hexalin | ????5.0 | ????87.5 |
????5 | N-Octanol | ????3.0 | ????97.0 |
????6 | Ethylene glycol | ????6.0 | ????92.5 |
Embodiment | Stopper | Reaction times | Product yield | Catalyzer repeats the reuse test |
789 10 | Hydroquinones phenthazine N-phenyl-1-naphthalene 2.2.6.6-tetramethyl phenylpiperidines alcohol NO free radical (the present invention) | 4.0 4.0 4.0 4.0 | 89.0 92.0 91.5 97.2 | Distillation residue are solid catalyst can not direct reuse distillation residue thickness, opaque, can not direct reuse.The same distillation residue good fluidity cannot not be sticking that but the transparent liquid catalyzer direct reuse of still is more than 10 times. |
Embodiment | Catalyzer | Reaction times (h) | Product yield (%) |
??11 | The methoxyl group tributyl tin | ????4.5 | ????92.0 |
??12 | Tributyltin chloride | ????7.5 | ????80.5 |
??13 | The dimethoxy dioctyl tin | ????4.0 | ????94.0 |
??14 | Dibutyltin oxide | ????4.5 | ????96.5 |
??15 | Two monomethyl maleate dibutyl tins | ????4.0 | ????97.0 |
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN95101716A CN1054117C (en) | 1995-01-26 | 1995-01-26 | Method for producing alkyl acrylate or alkyl methacrylate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN95101716A CN1054117C (en) | 1995-01-26 | 1995-01-26 | Method for producing alkyl acrylate or alkyl methacrylate |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1127745A true CN1127745A (en) | 1996-07-31 |
CN1054117C CN1054117C (en) | 2000-07-05 |
Family
ID=5074057
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN95101716A Expired - Fee Related CN1054117C (en) | 1995-01-26 | 1995-01-26 | Method for producing alkyl acrylate or alkyl methacrylate |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1054117C (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100349854C (en) * | 2001-06-08 | 2007-11-21 | 巴斯福股份公司 | Method for producing (meth) acrylic acid esters |
CN100349851C (en) * | 2001-06-08 | 2007-11-21 | 巴斯福股份公司 | Method for producing (meth) acrylic acid esters |
CN101041618B (en) * | 2006-03-24 | 2011-05-25 | 杭州格林香料化学有限公司 | New production technique of cyclohexyl allyl propionate |
CN102351693A (en) * | 2011-08-23 | 2012-02-15 | 里光 | Preparation method for methoxyethyl methacrylate |
CN114195639A (en) * | 2021-12-13 | 2022-03-18 | 抚顺东联安信化学有限公司 | Production process of long carbon chain alkyl methacrylate |
CN115197062A (en) * | 2022-08-29 | 2022-10-18 | 新乡市瑞丰新材料股份有限公司 | Acrylic acid high-carbon ester or methacrylic acid high-carbon ester and preparation method thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5365816A (en) * | 1976-11-26 | 1978-06-12 | Nitto Chem Ind Co Ltd | Preparation of dimethylaminoethyl methacrylate |
JPS63196544A (en) * | 1987-02-10 | 1988-08-15 | Osaka Yuki Kagaku Kogyo Kk | Production of fluorinated alkyl (meth)acrylates |
-
1995
- 1995-01-26 CN CN95101716A patent/CN1054117C/en not_active Expired - Fee Related
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100349854C (en) * | 2001-06-08 | 2007-11-21 | 巴斯福股份公司 | Method for producing (meth) acrylic acid esters |
CN100349851C (en) * | 2001-06-08 | 2007-11-21 | 巴斯福股份公司 | Method for producing (meth) acrylic acid esters |
CN101041618B (en) * | 2006-03-24 | 2011-05-25 | 杭州格林香料化学有限公司 | New production technique of cyclohexyl allyl propionate |
CN102351693A (en) * | 2011-08-23 | 2012-02-15 | 里光 | Preparation method for methoxyethyl methacrylate |
CN114195639A (en) * | 2021-12-13 | 2022-03-18 | 抚顺东联安信化学有限公司 | Production process of long carbon chain alkyl methacrylate |
CN114195639B (en) * | 2021-12-13 | 2023-09-19 | 抚顺东联安信化学有限公司 | Production process of long carbon chain alkyl methacrylate |
CN115197062A (en) * | 2022-08-29 | 2022-10-18 | 新乡市瑞丰新材料股份有限公司 | Acrylic acid high-carbon ester or methacrylic acid high-carbon ester and preparation method thereof |
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