CN103304413A - Synthetic method of 2-hydroxyethyl methacrylate - Google Patents
Synthetic method of 2-hydroxyethyl methacrylate Download PDFInfo
- Publication number
- CN103304413A CN103304413A CN2013101944773A CN201310194477A CN103304413A CN 103304413 A CN103304413 A CN 103304413A CN 2013101944773 A CN2013101944773 A CN 2013101944773A CN 201310194477 A CN201310194477 A CN 201310194477A CN 103304413 A CN103304413 A CN 103304413A
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- CN
- China
- Prior art keywords
- synthetic method
- hydroxyethyl methacrylate
- molecular sieve
- zeolite molecular
- methacrylic acid
- 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.)
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- 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
- Y02P20/584—Recycling of catalysts
Abstract
The invention discloses a synthetic method of 2-hydroxyethyl methacrylate. The synthetic method comprises the steps of: sequentially adding methacrylic acid and a magnetic zeolite molecular sieve into a reaction kettle, uniformly mixing, adding ethylene oxide into the reaction kettle, heating the reaction kettle until the temperature is 65-70 DEG C, reacting for 2-3h, and carrying out distillation to obtain the 2-hydroxyethyl methacrylate. According to the synthetic method disclosed by the invention, as the magnetic zeolite molecular sieve is adopted as a catalyst, a polymerization inhibitor is not needed, so that the 2-hydroxyethyl methacrylate is easily separated and purified, the yield of the 2-hydroxyethyl methacrylate can reach above 97 percent, and the synthesis cost is lowered as the catalyst can be recycled and reused.
Description
Technical field
The present invention is specifically related to a kind of synthetic method of hydroxyethyl methylacrylate.
Background technology
Hydroxyethyl methylacrylate (CAS:868-77-9) is the active functional monomer of a kind of character, the properties-correcting agent that is usually used in thermosetting coating, tackiness agent, fibre finish and synthetic resins multipolymer also can be used as the bridging property monomer of acrylic resin.
Hydroxyethyl methylacrylate is reacted in the presence of catalyzer by methacrylic acid and oxyethane and makes; for preventing the polymerization in reaction process of material methacrylic acid; reaction needs to add stopper usually; such as Resorcinol; methyl hydroquinone; anthracene; phenothiazine; phenothiazine; hydroquinone monomethyl ether and MEHQ etc.; catalyzer is commonly used pyridine; trichlorine assumed name's aluminium; the methacrylic acid alkali metal salt; organo-chromium compound; trivalent iron salt or organoiron compound; organophosphorus or sulphur compound etc.; a kind of preparation technology of hydroxyethyl methylacrylate is disclosed such as CN102584579A; adopt synthesize methyl acrylic acid hydroxyl ethyl ester under vacuum and the nitrogen protection, but existing synthetic method catalyzer can't be accomplished to recycle.
Summary of the invention
The objective of the invention is to solve the defective that existing method can't reclaim catalyzer, a kind of method of synthesize methyl acrylic acid hydroxyl ethyl ester of catalyzer recoverable is provided.
The present invention realizes that the technical scheme that above-mentioned purpose adopts is as follows:
A kind of synthetic method of hydroxyethyl methylacrylate, step is as follows:
Methacrylic acid is joined in the reactor, add the magnetic zeolite molecular sieve again, add oxyethane after stirring again, reactor is heated to 65～70 ℃, reaction 2～3h, and distillation obtains hydroxyethyl methylacrylate.
Further, described magnetic zeolite molecular sieve is pressed 4～6% addings of methacrylic acid quality.
Further, the mol ratio of described oxyethane and methacrylic acid is 1:(1.01～1.05).
Compare with existing method, after the present invention adopts the magnetic zeolite sieve peg-raking catalyst, need not to re-use stopper, thereby be conducive to the product separation purifying, and the productive rate of hydroxyethyl methylacrylate can reach more than 97%, and by product is few, and this may to have a selective reaction relevant with the meso-hole structure of zeolite molecular sieve, the recyclable recycling of catalyzer reduces synthetic cost.
The specific embodiment mode
Below in conjunction with embodiment the present invention is described in further details.
Magnetic zeolite molecular sieve of the present invention be according to Cao Jilin etc. " magnetic 4A zeolite molecular sieve synthetic with characterize " [
University Of Tianjin's journalThe 2nd phase of the 42nd volume in 2009] " 1.3 product synthetic method " synthetic obtaining of the 184th page.
Embodiment 1
The 100g methacrylic acid is joined in the reactor, add again 4g magnetic zeolite molecular sieve, stir, add 50.7g oxyethane, the off-response still is heated to 65 ℃ again, react after 3 hours, underpressure distillation is collected and is obtained 145g hydroxyethyl methylacrylate (productive rate 97%, purity 99.3%).
Embodiment 2
The 100g methacrylic acid is joined in the reactor, add again 6g magnetic zeolite molecular sieve, stir, add 48.7g oxyethane, the off-response still is heated to 70 ℃ again, react after 3 hours, underpressure distillation is collected and is obtained 141g hydroxyethyl methylacrylate (productive rate 98%, purity 99.2%).
Embodiment 3
The 100g methacrylic acid is joined in the reactor, add again 5g magnetic zeolite molecular sieve, stir, add 50g oxyethane, the off-response still is heated to 68 ℃ again, react after 2 hours, underpressure distillation is collected and is obtained 144g hydroxyethyl methylacrylate (productive rate 97.5%, purity 99.0%).
The recycling of catalyzer: with the magnetic zeolite molecular sieve in the electro-magnet recovery reaction solution, the magnetic zeolite molecular sieve that reclaims was calcined 2～3 hours in 180～200 ℃ after washing, after the magnetic zeolite molecular sieve recycle and reuse 8 times, the productive rate of hydroxyethyl methylacrylate still can reach more than 92%.
Claims (3)
1. the synthetic method of a hydroxyethyl methylacrylate is characterized in that, the step of described synthetic method is as follows:
Methacrylic acid is joined in the reactor, add the magnetic zeolite molecular sieve again, add oxyethane after stirring again, reactor is heated to 65～70 ℃, reaction 2～3h, and distillation obtains hydroxyethyl methylacrylate.
2. the synthetic method of described hydroxyethyl methylacrylate according to claim 1 is characterized in that, described magnetic zeolite molecular sieve is pressed 4～6% of methacrylic acid quality and added.
3. the synthetic method of described hydroxyethyl methylacrylate according to claim 1 is characterized in that, the mol ratio of described oxyethane and methacrylic acid is 1:(1.01～1.05).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013101944773A CN103304413A (en) | 2013-05-23 | 2013-05-23 | Synthetic method of 2-hydroxyethyl methacrylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013101944773A CN103304413A (en) | 2013-05-23 | 2013-05-23 | Synthetic method of 2-hydroxyethyl methacrylate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103304413A true CN103304413A (en) | 2013-09-18 |
Family
ID=49130174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2013101944773A Pending CN103304413A (en) | 2013-05-23 | 2013-05-23 | Synthetic method of 2-hydroxyethyl methacrylate |
Country Status (1)
| Country | Link |
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| CN (1) | CN103304413A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016008174A1 (en) * | 2014-07-14 | 2016-01-21 | 万华化学集团股份有限公司 | Method for preparing hydroxyethyl (methyl)acrylate |
| CN113861025A (en) * | 2021-10-29 | 2021-12-31 | 山东徳瑞高分子材料股份有限公司 | Continuous production method of hydroxypropyl methacrylate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060167304A1 (en) * | 2003-01-31 | 2006-07-27 | Mitsubishi Rayon Co., Ltd. | Apparatus for producing hydroxyalkyl (meth) acrylate and process for producing the same |
| CN101497563A (en) * | 2008-01-30 | 2009-08-05 | 赢创罗姆有限责任公司 | Process for preparation of high purity methacrylic acid |
-
2013
- 2013-05-23 CN CN2013101944773A patent/CN103304413A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060167304A1 (en) * | 2003-01-31 | 2006-07-27 | Mitsubishi Rayon Co., Ltd. | Apparatus for producing hydroxyalkyl (meth) acrylate and process for producing the same |
| CN101497563A (en) * | 2008-01-30 | 2009-08-05 | 赢创罗姆有限责任公司 | Process for preparation of high purity methacrylic acid |
Non-Patent Citations (2)
| Title |
|---|
| 曹吉林 等: "磁性4A沸石分子筛的合成与表征", 《天津大学学报》 * |
| 汪多仁: "丙烯酸酯的开发与应用进展", 《增塑剂》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016008174A1 (en) * | 2014-07-14 | 2016-01-21 | 万华化学集团股份有限公司 | Method for preparing hydroxyethyl (methyl)acrylate |
| US9845281B2 (en) | 2014-07-14 | 2017-12-19 | Wanhua Chemical Group Co., Ltd. | Method for preparing hydroxyethyl (meth) acrylate |
| CN113861025A (en) * | 2021-10-29 | 2021-12-31 | 山东徳瑞高分子材料股份有限公司 | Continuous production method of hydroxypropyl methacrylate |
| CN113861025B (en) * | 2021-10-29 | 2022-12-30 | 山东徳瑞高分子材料股份有限公司 | Continuous production method of hydroxypropyl methacrylate |
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