CN101462958B - (甲基)丙烯酸酯的制备方法 - Google Patents
(甲基)丙烯酸酯的制备方法 Download PDFInfo
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- CN101462958B CN101462958B CN200810185589.1A CN200810185589A CN101462958B CN 101462958 B CN101462958 B CN 101462958B CN 200810185589 A CN200810185589 A CN 200810185589A CN 101462958 B CN101462958 B CN 101462958B
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- methyl
- oxygen
- acrylate
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 59
- 239000001301 oxygen Substances 0.000 claims abstract description 58
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 29
- 239000003112 inhibitor Substances 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 19
- 239000011541 reaction mixture Substances 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007789 gas Substances 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 230000000630 rising effect Effects 0.000 claims abstract description 6
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- -1 2-ethylhexyl Chemical group 0.000 claims description 34
- 238000004821 distillation Methods 0.000 claims description 21
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical group CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
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- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical group CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 8
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-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
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- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-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
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- 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
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 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
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion 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
- 239000012530 fluid Substances 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
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 239000001923 methylcellulose Substances 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 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
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 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
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052726 zirconium Inorganic materials 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)
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| US1492707P | 2007-12-19 | 2007-12-19 | |
| US61/014,927 | 2007-12-19 |
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| CN101462958A CN101462958A (zh) | 2009-06-24 |
| CN101462958B true CN101462958B (zh) | 2016-01-20 |
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| CN (1) | CN101462958B (enExample) |
| TW (1) | TWI555728B (enExample) |
| WO (1) | WO2009080380A2 (enExample) |
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| US9206270B2 (en) * | 2007-12-19 | 2015-12-08 | Evonik Roehm 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 |
| MY185479A (en) * | 2014-12-01 | 2021-05-19 | Basf Se | Process for preparing heonone (meth)acrylate |
| CN107531724B (zh) | 2015-02-26 | 2020-06-23 | 巴斯夫欧洲公司 | 制备异山梨醇乙氧基化物二甲基丙烯酸酯的方法 |
| KR102572781B1 (ko) | 2015-02-26 | 2023-08-31 | 바스프 에스이 | 이소소르비드 디(메트)아크릴레이트의 제조 방법 |
| EP3390338A1 (de) | 2015-12-15 | 2018-10-24 | Basf Se | Verfahren zur herstellung von hydroxybenzophenonpolyglykolether-(meth)acrylat |
| JP7044758B2 (ja) | 2016-08-05 | 2022-03-30 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリイソブテン基を有するマクロモノマー、およびそれらのホモポリマーまたはコポリマー |
| US20240067596A1 (en) * | 2021-01-25 | 2024-02-29 | Basf Se | Continuous method for obtaining 2-ethylhexyl acrylate |
| WO2023143939A1 (de) | 2022-01-26 | 2023-08-03 | Basf Se | Lagerung und/oder transport ethylenisch ungesättigter verbindungen |
| WO2023242259A1 (en) * | 2022-06-15 | 2023-12-21 | Evonik Operations Gmbh | Method for increasing reaction performance by intermediate removal of side product holdup |
| EP4293010A1 (en) * | 2022-06-15 | 2023-12-20 | Evonik Operations GmbH | Process for the discontinuous (trans)esterification of (meth)acrylate compounds |
| 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 |
| CN119562975A (zh) * | 2022-10-31 | 2025-03-04 | 三菱化学株式会社 | 含有酯化合物的组合物及其制造方法、聚合性组合物、（甲基）丙烯酸系聚合物及其制造方法 |
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| DE3423443A1 (de) * | 1984-06-26 | 1986-01-02 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von estern der acryl- und methacrylsaeure durch umesterung |
| WO1991016037A1 (en) * | 1990-04-16 | 1991-10-31 | Minnesota Mining And Manufacturing Company | Mildness additives for skin cleansing compositions |
| 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 |
| 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 |
| 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 |
| JP2949150B1 (ja) | 1998-02-27 | 1999-09-13 | 日精化学工業株式会社 | 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 |
| DE19940622C1 (de) * | 1999-08-27 | 2001-05-17 | Roehm Gmbh | Verfahren zur Herstellung von Di(meth)acrylsäureestern |
| CA2384389A1 (en) * | 2000-08-08 | 2002-02-14 | Kaneka Corporation | Expandable vinyl chloride resin composition |
| 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 |
| 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 |
| DE10301902A1 (de) * | 2003-01-17 | 2003-12-04 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| 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 |
| 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 |
| US9206270B2 (en) * | 2007-12-19 | 2015-12-08 | Evonik Roehm Gmbh | Process for preparing (meth)acrylates |
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2008
- 2008-09-29 US US12/745,703 patent/US9206270B2/en active Active
- 2008-09-29 EP EP08804845.9A patent/EP2220023B1/en active Active
- 2008-09-29 JP JP2010538506A patent/JP2011506517A/ja active Pending
- 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
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2009080380A3 (en) | 2009-09-17 |
| TWI555728B (zh) | 2016-11-01 |
| JP2020073555A (ja) | 2020-05-14 |
| JP2014237723A (ja) | 2014-12-18 |
| EP2220023A2 (en) | 2010-08-25 |
| TW200946496A (en) | 2009-11-16 |
| US9206270B2 (en) | 2015-12-08 |
| EP2220023B1 (en) | 2017-04-05 |
| JP2022081593A (ja) | 2022-05-31 |
| US20100280205A1 (en) | 2010-11-04 |
| WO2009080380A2 (en) | 2009-07-02 |
| US20160046556A1 (en) | 2016-02-18 |
| JP2011506517A (ja) | 2011-03-03 |
| JP2017088608A (ja) | 2017-05-25 |
| CN101462958A (zh) | 2009-06-24 |
| US9688601B2 (en) | 2017-06-27 |
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