TW201024260A - Processes for producing hydroxyalkyl (meth) acrylate - Google Patents
Processes for producing hydroxyalkyl (meth) acrylate Download PDFInfo
- Publication number
- TW201024260A TW201024260A TW099103140A TW99103140A TW201024260A TW 201024260 A TW201024260 A TW 201024260A TW 099103140 A TW099103140 A TW 099103140A TW 99103140 A TW99103140 A TW 99103140A TW 201024260 A TW201024260 A TW 201024260A
- Authority
- TW
- Taiwan
- Prior art keywords
- reaction
- catalyst
- meth
- acrylic acid
- acrylate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 91
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 52
- 125000002768 hydroxyalkyl group Chemical group 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 347
- 239000003054 catalyst Substances 0.000 claims abstract description 194
- 239000002253 acid Substances 0.000 claims abstract description 141
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 113
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 31
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000012295 chemical reaction liquid Substances 0.000 claims description 175
- 150000001875 compounds Chemical class 0.000 claims description 60
- 238000004519 manufacturing process Methods 0.000 claims description 55
- -1 hydroxyalkyl (indenyl) acrylate Chemical compound 0.000 claims description 46
- 239000000047 product Substances 0.000 claims description 28
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- 239000000052 vinegar Substances 0.000 claims description 20
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- 239000011651 chromium Substances 0.000 claims description 17
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 11
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- DAWJJMYZJQJLPZ-UHFFFAOYSA-N 2-sulfanylprop-2-enoic acid Chemical compound OC(=O)C(S)=C DAWJJMYZJQJLPZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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- 239000010452 phosphate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 description 1
- GTCKPGDAPXUISX-UHFFFAOYSA-N ruthenium(3+);trinitrate Chemical compound [Ru+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GTCKPGDAPXUISX-UHFFFAOYSA-N 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 229910000348 titanium sulfate Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004231379 | 2004-08-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201024260A true TW201024260A (en) | 2010-07-01 |
| TWI347315B TWI347315B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2011-08-21 |
Family
ID=35787249
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099103140A TW201024260A (en) | 2004-08-06 | 2005-08-08 | Processes for producing hydroxyalkyl (meth) acrylate |
| TW094126686A TW200616945A (en) | 2004-08-06 | 2005-08-08 | Processes for producing hydroxyalkyl (methyl)acrylate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094126686A TW200616945A (en) | 2004-08-06 | 2005-08-08 | Processes for producing hydroxyalkyl (methyl)acrylate |
Country Status (6)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5089964B2 (ja) * | 2006-11-17 | 2012-12-05 | 株式会社日本触媒 | ヒドロキシアルキル（メタ）アクリレートの製造方法及び製造システム |
| US8738792B2 (en) * | 2007-01-31 | 2014-05-27 | International Business Machines Corporation | Server time protocol messages and methods |
| US20150126767A1 (en) * | 2012-05-31 | 2015-05-07 | Nippon Shokubai Co., Ltd. | Hydroxyalkyl (meth)acrylate and method for producing same |
| JP5875956B2 (ja) * | 2012-08-02 | 2016-03-02 | 株式会社日本触媒 | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| KR102033744B1 (ko) * | 2012-09-24 | 2019-10-17 | 가부시기가이샤 닛뽕쇼꾸바이 | 하이드록시알킬아크릴레이트, 및 그 제조방법 |
| CN104119227A (zh) * | 2013-04-27 | 2014-10-29 | 复旦大学 | 一种羧酸与环氧乙烷化合物酯化反应的方法 |
| CN105272851B (zh) * | 2014-07-14 | 2017-09-19 | 万华化学集团股份有限公司 | 一种(甲基)丙烯酸羟乙酯的制备方法 |
| US20170305832A1 (en) * | 2014-10-22 | 2017-10-26 | Dow Global Technologies Llc | Preparation of a sorbate ester |
| CN114835578A (zh) * | 2022-06-10 | 2022-08-02 | 安徽三禾化学科技有限公司 | 一种丙烯酸羟丙脂的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3875211A (en) * | 1973-01-22 | 1975-04-01 | Alcolac Inc | Process for preparing 2-hydroxyalkylacrylates and 2-hydroxyalkylmethacrylates |
| US4365081A (en) * | 1980-05-20 | 1982-12-21 | Nippon Shokubai Kagaku Kogyo Co. Ltd. | Process for producing 2-hydroxyalkyl acrylates or methacrylates |
| JP4772997B2 (ja) * | 2001-07-30 | 2011-09-14 | 株式会社日本触媒 | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| JP2003040837A (ja) * | 2001-07-30 | 2003-02-13 | Nippon Shokubai Co Ltd | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| JP3990580B2 (ja) | 2002-03-12 | 2007-10-17 | 株式会社日本触媒 | （メタ）アクリル酸エステルの重合防止方法 |
| JP4074469B2 (ja) * | 2002-04-05 | 2008-04-09 | 株式会社日本触媒 | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| JP3907532B2 (ja) | 2002-06-11 | 2007-04-18 | 株式会社日本触媒 | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| JP2004010603A (ja) | 2002-06-11 | 2004-01-15 | Nippon Shokubai Co Ltd | ヒドロキシアルキル（メタ）アクリレートおよびその製造方法 |
| JP2004075559A (ja) | 2002-08-12 | 2004-03-11 | Nippon Shokubai Co Ltd | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| JP4564226B2 (ja) | 2002-09-30 | 2010-10-20 | 株式会社日本触媒 | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| JP2004182634A (ja) * | 2002-12-02 | 2004-07-02 | Nippon Shokubai Co Ltd | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| JP2004244364A (ja) * | 2003-02-13 | 2004-09-02 | Nippon Shokubai Co Ltd | ヒドロキシアルキルメタクリレートの製造方法 |
-
2005
- 2005-08-05 CN CN2005800260099A patent/CN1993312B/zh not_active Expired - Lifetime
- 2005-08-05 US US11/659,370 patent/US8203018B2/en active Active
- 2005-08-05 JP JP2006531592A patent/JP4866734B2/ja not_active Expired - Lifetime
- 2005-08-05 WO PCT/JP2005/014421 patent/WO2006013971A1/ja active Application Filing
- 2005-08-05 EP EP05768905A patent/EP1775279B1/en not_active Expired - Lifetime
- 2005-08-08 TW TW099103140A patent/TW201024260A/zh unknown
- 2005-08-08 TW TW094126686A patent/TW200616945A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1775279A4 (en) | 2008-10-08 |
| EP1775279B1 (en) | 2011-11-30 |
| TWI347315B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2011-08-21 |
| JP4866734B2 (ja) | 2012-02-01 |
| JPWO2006013971A1 (ja) | 2008-07-31 |
| TW200616945A (en) | 2006-06-01 |
| US20080154060A1 (en) | 2008-06-26 |
| CN1993312B (zh) | 2010-06-16 |
| WO2006013971A1 (ja) | 2006-02-09 |
| CN1993312A (zh) | 2007-07-04 |
| TWI323253B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2010-04-11 |
| EP1775279A1 (en) | 2007-04-18 |
| US8203018B2 (en) | 2012-06-19 |
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