CN103739571A - Synthesis method of phenyl glycidyl ether - Google Patents
Synthesis method of phenyl glycidyl ether Download PDFInfo
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- CN103739571A CN103739571A CN201310519713.4A CN201310519713A CN103739571A CN 103739571 A CN103739571 A CN 103739571A CN 201310519713 A CN201310519713 A CN 201310519713A CN 103739571 A CN103739571 A CN 103739571A
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- glycidyl ether
- phenyl glycidyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- C07D303/23—Oxiranylmethyl ethers of compounds having one hydroxy group bound to a six-membered aromatic ring, the oxiranylmethyl radical not being further substituted, i.e.
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
- C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
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Abstract
The invention relates to a synthesis method of phenyl glycidyl ether, and is characterized in that phenyl glycidyl ether is generated with phenol and chloropropylene oxide as raw materials and under the action of a catalyst, wherein the reaction is carried out in a micro-reactor. The method can greatly shorten the reaction time, avoids a lot of side reactions, and can synthesize phenyl glycidyl ether with high efficiency and high yield of more than 98%.
Description
Technical field
The synthetic method that the present invention relates to a kind of phenyl glycidyl ether, belongs to field of chemical technology.
Background technology
Phenyl glycidyl ether chemistry 1,2-epoxy-3-phenoxypropane by name; 2,3-epoxypropyl phenylether, structural formula is shown in that accompanying drawing 1 phenyl glycidyl ether is important organic chemistry intermediate, can be widely used in coatings industry, rubber industry and synthetic resin industry.In recent years, the applied research of relevant phenyl glycidyl ether is very active, is mainly concerned with the fields such as synthetic, resin modified, organic synthesis of synthetic, the homopolymer of multipolymer.
Traditional synthetic method of phenyl glycidyl ether is under the existence of phase-transfer catalyst, by phenol and epichlorohydrin reaction, is obtained.The feature of the method is that raw material is simple and easy to get, and building-up process is simple to operate, is the method that enterprise generally adopts both at home and abroad at present.But the method needs epoxy chloropropane excessive a lot, and need to use a large amount of organic solvents, and reaction side reaction is many, is not easy to purify, and aftertreatment is complicated, and yield is generally at 85-88%.Have in addition document report ionic liquid method synthesis of phenyl glycidyl ether, yield can reach 96.8%, but the ionic liquid that the method adopts combines more complicated, and expensive, in the process of practical application, reuses effect bad.
Summary of the invention
Shortcoming for the synthesis technique of above-mentioned phenyl glycidyl ether, the object of the present invention is to provide a kind of raw material to transform completely, and side reaction is few, yield is high, mild condition, easy and simple to handle, be easier to the synthetic method of the phenyl glycidyl ether of industrialized more environmental protection.Compare with method in the past, the method is Reaction time shorten greatly, thereby has avoided a large amount of side reactions, can be with high-level efficiency, high yield (more than 98%) and high purity synthesis of phenyl glycidyl ether.
Technology contents of the present invention is: the synthetic method of phenyl glycidyl ether, it is characterized in that: take phenol, epoxy chloropropane is raw material, under the effect of catalyzer, in microreactor, reaction generates phenyl glycidyl ether, catalyzer is Tetrabutyl amonium bromide, 4 bromide, benzyltrimethylammonium bromide, poly(oxyethylene glycol) 400, Polyethylene Glycol-600, and consumption is 0.5wt%.The feed ratio of phenol and epoxy chloropropane is 1:1-1.3 (mol), and temperature of reaction is 30-100 ℃, and the reaction times is 2-30 minute.
The microreactor using in the present invention refers to that fluid flowing passage characteristic dimension is at the reactor of hundreds of micrometer ranges.Mainz, Germany microtechnology institute is one of research institution being engaged in the earliest in the world microreactor technological development, has successfully developed the microreactor assembly that is applicable to various chemical processes, can be for lab scale research and actual production.In fine chemistry industry and medicine organic synthesis, the application of microreactor technology obtains the most extensive research, has had in the market the production technique based on microreactor technology of multiple maturation.At other field, as microreactor technology in bulk chemical and Polymer Synthesizing is also more and more applied.For example, Siemens Company has developed the production technique of utilizing microreactor to prepare polyacrylic ester, and throughput reaches 2000 tons/year.Degussa group has developed the large-scale microreactor for production of propylene oxide based on microreactor technology.The inventor, by a large amount of groping and testing, is optimized various reaction parameters, final successfully the synthesizing for phenyl glycidyl ether by microreactor.
The reaction formula relating in the present invention is as follows:
Accompanying drawing explanation
Fig. 1: phenyl glycidyl ether structural formula; Fig. 2: the building-up reactions formula of phenyl glycidyl ether.
Specific embodiment
The invention is further illustrated by the following examples, but the invention is not restricted to lifted embodiment.
The raw material that the present invention uses is analytical pure, is the chemical reagent of traditional Chinese medicines group.The typical liquid Liquid-phase reactor that microreactor adopts Bayer A.G to produce.
Embodiment 1
After 94g phenol joins and fully dissolves in the aqueous sodium hydroxide solution of 220g20% standby (solution 1), in microreactor, pass into solution 1 and epoxy chloropropane, throughput ratio is 6.0/2.0 (ml/min), temperature of reaction is 40 ℃, react and obtain phenyl glycidyl ether 148g after 5 minutes, content 98.2%, yield 98.6%.
Embodiment 2
After 94g phenol joins and fully dissolves in the aqueous sodium hydroxide solution of 220g20% standby (solution 1), in microreactor, pass into solution 1 and epoxy chloropropane, throughput ratio is 0.6/0.2 (ml/min), temperature of reaction is 40 ℃, react and obtain phenyl glycidyl ether 140g after 5 minutes, content 97.3%, yield 93.3%.
Embodiment 3
After 94g phenol joins and fully dissolves in the aqueous sodium hydroxide solution of 220g20% standby (solution 1), in microreactor, pass into solution 1 and epoxy chloropropane, throughput ratio is 15.0/5.0 (ml/min), temperature of reaction is 40 ℃, react and obtain phenyl glycidyl ether 142g after 5 minutes, content 97.6%, yield 94.6%.
Embodiment 4
After 94g phenol joins and fully dissolves in the aqueous sodium hydroxide solution of 220g20% standby (solution 1), in microreactor, pass into solution 1 and epoxy chloropropane, throughput ratio is 6.0/2.0 (ml/min), temperature of reaction is 60 ℃, react and obtain phenyl glycidyl ether 141g after 5 minutes, content 96.5%, yield 94.0%.
Embodiment 5
After 94g phenol joins and fully dissolves in the aqueous sodium hydroxide solution of 220g20% standby (solution 1), in microreactor, pass into solution 1 and epoxy chloropropane, throughput ratio is 6.0/2.0 (ml/min), temperature of reaction is 90 ℃, react and obtain phenyl glycidyl ether 143g after 5 minutes, content 98.5%, yield 95.3%.
Embodiment 6
After 94g phenol joins and fully dissolves in the aqueous sodium hydroxide solution of 220g20% standby (solution 1), in microreactor, pass into solution 1 and epoxy chloropropane, throughput ratio is 9.0/3.0 (ml/min), temperature of reaction is 90 ℃, react and obtain phenyl glycidyl ether 148.5g after 5 minutes, content 98.5%, yield 99.0%.
Claims (3)
1. a synthetic method for phenyl glycidyl ether, is characterized in that: take phenol, epoxy chloropropane is raw material, and under catalyst action, in microreactor, reaction generates phenyl glycidyl ether.
2. synthetic method as claimed in claim 1, is characterized in that: described catalyzer is Tetrabutyl amonium bromide, 4 bromide, benzyltrimethylammonium bromide, poly(oxyethylene glycol) 400, Polyethylene Glycol-600, and consumption is 0.5wt%.
3. as claim 1 and synthetic method claimed in claim 2, it is characterized in that: the feed ratio of phenol and epoxy chloropropane is 1:1-1.3 (mol), and temperature of reaction is 30-100 ℃, and the reaction times is 2-30 minute.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310519713.4A CN103739571A (en) | 2013-10-30 | 2013-10-30 | Synthesis method of phenyl glycidyl ether |
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| CN201310519713.4A CN103739571A (en) | 2013-10-30 | 2013-10-30 | Synthesis method of phenyl glycidyl ether |
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| CN103739571A true CN103739571A (en) | 2014-04-23 |
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| CN201310519713.4A Pending CN103739571A (en) | 2013-10-30 | 2013-10-30 | Synthesis method of phenyl glycidyl ether |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592167A (en) * | 2014-12-31 | 2015-05-06 | 湖北绿色家园精细化工有限责任公司 | Method for preparing phenyl glycidyl ether |
| CN111574335A (en) * | 2020-05-19 | 2020-08-25 | 南京林业大学 | Propylene glycol oligomer device and preparation method |
| CN112250646A (en) * | 2020-10-12 | 2021-01-22 | 利安隆（中卫）新材料有限公司 | Process for preparing alkyl glycidyl ethers |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH107761A (en) * | 1996-06-21 | 1998-01-13 | Asahi Denka Kogyo Kk | Production of aliphatic polyglycidyl ether |
| CN103232408A (en) * | 2012-12-31 | 2013-08-07 | 上海安诺其纺织化工股份有限公司 | Disperse dye compound |
| CN103232723A (en) * | 2012-12-31 | 2013-08-07 | 上海安诺其纺织化工股份有限公司 | Easter compounds and preparation method thereof |
-
2013
- 2013-10-30 CN CN201310519713.4A patent/CN103739571A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH107761A (en) * | 1996-06-21 | 1998-01-13 | Asahi Denka Kogyo Kk | Production of aliphatic polyglycidyl ether |
| CN103232408A (en) * | 2012-12-31 | 2013-08-07 | 上海安诺其纺织化工股份有限公司 | Disperse dye compound |
| CN103232723A (en) * | 2012-12-31 | 2013-08-07 | 上海安诺其纺织化工股份有限公司 | Easter compounds and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 杜巧云: "3-苯氧基-2-轻丙基甲基丙烯酸醋的合成与表征", 《化学世界》, no. 10, 31 October 2002 (2002-10-31) * |
| 汪海平，等: "1-氯-3-苯氧基-2-丙醇的合成", 《广东化工》, no. 6, 30 June 2005 (2005-06-30) * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592167A (en) * | 2014-12-31 | 2015-05-06 | 湖北绿色家园精细化工有限责任公司 | Method for preparing phenyl glycidyl ether |
| CN111574335A (en) * | 2020-05-19 | 2020-08-25 | 南京林业大学 | Propylene glycol oligomer device and preparation method |
| CN111574335B (en) * | 2020-05-19 | 2023-03-17 | 南京林业大学 | Propylene glycol oligomer device and preparation method |
| CN112250646A (en) * | 2020-10-12 | 2021-01-22 | 利安隆（中卫）新材料有限公司 | Process for preparing alkyl glycidyl ethers |
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Application publication date: 20140423 |