TWI555728B - 製備（甲基）丙烯酸酯之方法 - Google Patents
製備（甲基）丙烯酸酯之方法 Download PDFInfo
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- TWI555728B TWI555728B TW097148967A TW97148967A TWI555728B TW I555728 B TWI555728 B TW I555728B TW 097148967 A TW097148967 A TW 097148967A TW 97148967 A TW97148967 A TW 97148967A TW I555728 B TWI555728 B TW I555728B
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- Prior art keywords
- oxygen
- meth
- acrylate
- formula
- reaction
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- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
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- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
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- 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
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- PYFQJAMTSYUJMX-UHFFFAOYSA-N phenazine Chemical compound C1=CC=CC2=NC3=CC=CC=C3N=C21.C1=CC=CC2=NC3=CC=CC=C3N=C21 PYFQJAMTSYUJMX-UHFFFAOYSA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
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- 229920001567 vinyl ester resin Polymers 0.000 description 1
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- 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 |
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| CN (1) | CN101462958B (cg-RX-API-DMAC10.html) |
| TW (1) | TWI555728B (cg-RX-API-DMAC10.html) |
| WO (1) | WO2009080380A2 (cg-RX-API-DMAC10.html) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2009080380A2 (en) * | 2007-12-19 | 2009-07-02 | 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 |
| EP3227265B1 (de) * | 2014-12-01 | 2018-10-17 | Basf Se | Verfahren zur herstellung von heonon(meth)acrylat |
| AU2016223466A1 (en) | 2015-02-26 | 2017-09-07 | Basf Se | Method for producing isosorbide dimethacrylate |
| US9562054B2 (en) | 2015-02-26 | 2017-02-07 | Basf Se | Process for preparing isosorbide ethoxylate di(meth)acrylate |
| CN108368020A (zh) | 2015-12-15 | 2018-08-03 | 巴斯夫欧洲公司 | 羟基二苯甲酮聚乙二醇醚(甲基)丙烯酸酯的制备方法 |
| CA3032569C (en) | 2016-08-05 | 2025-07-08 | Basf Se | MACROMONOMERS CONTAINING POLYISOBUTENE GROUPS AND RELATED HOMOPOLYMERS OR COPOLYMERS |
| KR20230132858A (ko) * | 2021-01-25 | 2023-09-18 | 바스프 에스이 | 2-에틸헥실 아크릴레이트를 수득하기 위한 연속 방법 |
| EP4469429A1 (de) | 2022-01-26 | 2024-12-04 | 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 |
| JPWO2024095957A1 (cg-RX-API-DMAC10.html) * | 2022-10-31 | 2024-05-10 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20040147772A1 (en) * | 2003-01-17 | 2004-07-29 | Basf Aktiengesellschaft | Preparation of (meth)acrylic esters |
| US20060148928A1 (en) * | 2004-12-30 | 2006-07-06 | Harris William F | Modified latex drag reducer and processes therefor and therewith |
Family Cites Families (23)
| 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 |
| AU651102B2 (en) * | 1990-04-16 | 1994-07-14 | 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| CN1331925C (zh) * | 2000-08-08 | 2007-08-15 | 钟渊化学工业株式会社 | 发泡性氯乙烯系树脂组合物 |
| KR100543821B1 (ko) | 2000-10-23 | 2006-01-23 | 가부시키가이샤 닛폰 쇼쿠바이 | 비닐 에테르기 함유 (메트)아크릴산 에스테르 조성물 및이의 제조방법 |
| 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 |
| 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 |
| 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 |
| JP5119926B2 (ja) * | 2005-11-21 | 2013-01-16 | 東亞合成株式会社 | （メタ）アクリル酸エステルの製造方法 |
| WO2009080380A2 (en) * | 2007-12-19 | 2009-07-02 | Evonik Röhm Gmbh | Process for preparing (meth)acrylates |
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2008
- 2008-09-29 WO PCT/EP2008/062982 patent/WO2009080380A2/en not_active Ceased
- 2008-09-29 EP EP08804845.9A patent/EP2220023B1/en active Active
- 2008-09-29 US US12/745,703 patent/US9206270B2/en active Active
- 2008-09-29 JP JP2010538506A patent/JP2011506517A/ja active Pending
- 2008-12-16 TW TW097148967A patent/TWI555728B/zh active
- 2008-12-17 CN CN200810185589.1A patent/CN101462958B/zh active Active
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2014
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2015
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- 2022-03-08 JP JP2022035159A patent/JP2022081593A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20040147772A1 (en) * | 2003-01-17 | 2004-07-29 | Basf Aktiengesellschaft | Preparation of (meth)acrylic esters |
| US20060148928A1 (en) * | 2004-12-30 | 2006-07-06 | Harris William F | Modified latex drag reducer and processes therefor and therewith |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009080380A3 (en) | 2009-09-17 |
| JP2022081593A (ja) | 2022-05-31 |
| TW200946496A (en) | 2009-11-16 |
| JP2020073555A (ja) | 2020-05-14 |
| JP2011506517A (ja) | 2011-03-03 |
| JP2014237723A (ja) | 2014-12-18 |
| CN101462958B (zh) | 2016-01-20 |
| EP2220023B1 (en) | 2017-04-05 |
| US20100280205A1 (en) | 2010-11-04 |
| US9206270B2 (en) | 2015-12-08 |
| EP2220023A2 (en) | 2010-08-25 |
| US20160046556A1 (en) | 2016-02-18 |
| CN101462958A (zh) | 2009-06-24 |
| US9688601B2 (en) | 2017-06-27 |
| JP2017088608A (ja) | 2017-05-25 |
| WO2009080380A2 (en) | 2009-07-02 |
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