CN103880603A - Method for preparing styrenated phenol by catalysis - Google Patents
Method for preparing styrenated phenol by catalysis Download PDFInfo
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- CN103880603A CN103880603A CN201410115083.9A CN201410115083A CN103880603A CN 103880603 A CN103880603 A CN 103880603A CN 201410115083 A CN201410115083 A CN 201410115083A CN 103880603 A CN103880603 A CN 103880603A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
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Abstract
The invention discloses a method for preparing styrenated phenol by catalysis. Phenol and styrene are adopted as raw materials, and macroporous strong acid cation exchange resin is taken as a catalyst. The method comprises the following steps: by taking phenol and styrene as raw materials, macroporous strong acid cation exchange resin as a catalyst for synthetic reaction, carrying out synthetic reaction, filtration and distillation to produce the product. According to the catalytic synthesis process, the design reaction temperature is controlled at 85-110 DEG C, so that the reaction speed is improved when the reaction temperature is greatly reduced, the energy consumption of the synthetic process is obviously reduced, the technical requirements on production equipment, process control and the like are also further reduced, the overall synthetic process is also simplified, and better social and economic benefits can be obtained by popularization and application.
Description
Technical field
The invention belongs to the preparation method of styrenated phenol.Be particularly related to a kind ofly take phenol and vinylbenzene as raw material, under the exchange resin catalyzed effect of macropore strong acid cation, make styrenated phenol through building-up reactions, suction filtration, distillation.Belong to the preparing technical field of styrenated phenol.
Background technology
Styrenated phenol has another name called antioxidant SP, light yellow viscous liquid, and it is not only a kind of important industrial chemicals, is also a kind of highly effective anti-aging agent, has efficient, low toxicity, the advantage such as inexpensive.It is mainly used in the stablizer of styrene-butadiene rubber(SBR) and chloroprene rubber etc., and the oxidation inhibitor of Polyolefin and polyoxymethylene etc. can delay the oxidising process of synthesized polymer material, guarantees the stability of goods processing and application.Styrenated phenol is a kind of without pollution rubber antioxidant, simultaneously as induced by alkyl hydroxybenzene oxidation inhibitor, and its large usage quantity.
The at present both at home and abroad technique take phenol and vinylbenzene as raw material synthesizing styrene phenol, catalyzer mainly adopts mineral acid (hydrochloric acid, sulfuric acid, phosphoric acid, polyphosphoric acid), oxalic acid, aluminum chloride, atlapulgite, toluenesulphonic acids, sulfonic acid ion exchange resin etc., although product yield is also relatively good, but whole synthesis reaction temperature is normally all more than 120 ℃, people's researchs such as the Zhang Jinlong of Nanjing Petroleum chemical engineering Co., Ltd show, while adopting tosic acid resin as catalyzer, temperature of reaction need to be at 120 ℃～130 ℃.
Macropore strong acid cation exchange resin is the new catalyst that is widely used in building-up reactions, Chinese patent CN101412795, CN102190768, CN103613501 all adopt the catalyzer of macropore strong acid cation exchange resin for organic compound building-up reactions, all obtain synthesis procedure simplification, the newly-increased discharge of wastewater of nothing, reduced environmental pollution, and improved the beneficial effect of feed stock conversion and product yield.
Summary of the invention
The object of the present invention is to provide a kind of new catalysis to prepare the method for styrenated phenol, the problems such as existing styrenated phenol synthesis technique temperature of reaction is high to overcome, energy consumption is large, technological operation is comparatively loaded down with trivial details obtain that environmental friendliness, yield are high, the effect of good product quality simultaneously.
The technical scheme that the present invention solves the problems of the technologies described above is as follows:
A method for styrenated phenol is produced in catalysis, and raw material adopts phenol, vinylbenzene, and catalyzer adopts macropore strong acid cation exchange resin, comprises the following steps:
1) will after phenol metering, drop in four-hole bottle and heat 80 ± 5 ℃, next adds catalyzer, then under rapid stirring, drips vinylbenzene, in 30 minutes, adds;
2) feed liquid is sent out and is answered 30～120 minutes at 85～110 ℃;
3), after having reacted, through suction filtration, distillation, finally obtain styrenated phenol.
Described raw material consumption is: vinylbenzene (mole number): phenol (mole number)=1.5～2.5:1.
Described catalyst levels is phenol 4～10% of the weight that feeds intake.
Described temperature of reaction is preferably 88～100 ℃, more preferably 90～92 ℃ of described temperature of reaction.
Vinylbenzene dropping and reaction times overall control are between 60～150 minutes.
Phenol, vinylbenzene in this preparation technology can adopt industrial raw material.
The invention has the beneficial effects as follows:
Present method is take phenol and vinylbenzene as raw material, adopt the catalyzer of macropore strong acid cation exchange resin as building-up reactions, carry out condensation reaction, make product through suction filtration, distillation, the design of this catalysis synthesizing technology has significantly reduced temperature of reaction, improve speed of response, significantly reduce the energy consumption of synthesis technique simultaneously, also can further reduce the technical requirements to production unit, technique manipulation etc., whole synthesis technique is also more simplified the operation control of being more convenient for, and its application also can obtain better economic results in society.
Accompanying drawing explanation
Be described further below in conjunction with embodiment and accompanying drawing.
Fig. 1 is preparation technology's schema of the present invention.
Embodiment
Further illustrate the solution of the present invention and effect below in conjunction with embodiment and Fig. 1.
Dry four-hole boiling flask is put into water heating thermostat and fix and install stirring, two mouths of four-hole boiling flask are loaded onto respectively ball-type reflux condensing tube and thermometer, then 80g phenol (technical grade) is put in four-hole boiling flask, start and stir and heat, rotating speed is controlled in 50～100r/min, in the time that rising to 80 ℃, temperature adds 6.4g macropore strong acid cation exchange resin, then drip the vinylbenzene of 189ml, approximately 30 points of kinds add, 90～92 ℃ are refluxed, condensation reaction 2h, reclaim catalyzer through suction filtration, after being distilled, filtrate obtains 239g styrenated phenol product, styrenated phenol product viscosity is 3537MPa.s after testing.
Claims (6)
1. a method for styrenated phenol is prepared in catalysis, it is characterized in that, raw material adopts phenol, vinylbenzene, and catalyzer adopts macropore strong acid cation exchange resin.
2. the method for styrenated phenol is prepared in a kind of catalysis according to claim 1, it is characterized in that comprising the following steps:
1) will after phenol metering, drop in four-hole bottle and heat 80 ± 5 ℃, next adds catalyzer, then under rapid stirring, drips vinylbenzene, in 30 minutes, adds;
2) feed liquid is sent out and is answered 30～120 minutes at 85～110 ℃;
3), after having reacted, through suction filtration, distillation, finally obtain styrenated phenol.
3. the method for styrenated phenol is prepared in a kind of catalysis according to claim 1 and 2, it is characterized in that described raw material consumption is: vinylbenzene (mole number): phenol (mole number)=1.5～2.5:1.
4. the method for styrenated phenol is prepared in a kind of catalysis according to claim 1 and 2, it is characterized in that described catalyst levels is phenol 4～10% of the weight that feeds intake.
5. the method for styrenated phenol is prepared in a kind of catalysis according to claim 2, it is characterized in that temperature of reaction is 88～100 ℃.
6. the method for styrenated phenol is prepared in a kind of catalysis according to claim 2, it is characterized in that temperature of reaction is 90～92 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201410115083.9A CN103880603A (en) | 2014-03-25 | 2014-03-25 | Method for preparing styrenated phenol by catalysis |
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| CN201410115083.9A CN103880603A (en) | 2014-03-25 | 2014-03-25 | Method for preparing styrenated phenol by catalysis |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105237359A (en) * | 2015-11-10 | 2016-01-13 | 辽宁大学 | Preparation method of phenethyl/cumenyl phenol chemicals |
| CN108752169A (en) * | 2018-07-18 | 2018-11-06 | 徐州工业职业技术学院 | A kind of method of Nafion resin catalysis synthesis antioxidant SP |
| CN109627146A (en) * | 2018-12-07 | 2019-04-16 | 浙江皇马科技股份有限公司 | A kind of preparation method of styrylphenol |
| CN110981701A (en) * | 2019-12-24 | 2020-04-10 | 江苏精禾界面科技有限公司 | Method for synthesizing polystyrolated phenol |
| RU2802029C1 (en) * | 2023-02-21 | 2023-08-22 | Акционерное общество "Стерлитамакский нефтехимический завод" | Method for producing mixture of methyl-benzylated phenols |
| CN118084625A (en) * | 2024-01-23 | 2024-05-28 | 浙江皇马科技股份有限公司 | A kind of synthetic method of styrenated phenol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1045258A (en) * | 1989-12-29 | 1990-09-12 | 天津大学 | The preparation of alpha-methyl benzyl phenol |
| CN1962591A (en) * | 2005-11-11 | 2007-05-16 | 中国石油化工股份有限公司 | 2,4-di-(1-phenylisopropyl) phenol preparation method |
-
2014
- 2014-03-25 CN CN201410115083.9A patent/CN103880603A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1045258A (en) * | 1989-12-29 | 1990-09-12 | 天津大学 | The preparation of alpha-methyl benzyl phenol |
| CN1962591A (en) * | 2005-11-11 | 2007-05-16 | 中国石油化工股份有限公司 | 2,4-di-(1-phenylisopropyl) phenol preparation method |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105237359A (en) * | 2015-11-10 | 2016-01-13 | 辽宁大学 | Preparation method of phenethyl/cumenyl phenol chemicals |
| CN108752169A (en) * | 2018-07-18 | 2018-11-06 | 徐州工业职业技术学院 | A kind of method of Nafion resin catalysis synthesis antioxidant SP |
| CN109627146A (en) * | 2018-12-07 | 2019-04-16 | 浙江皇马科技股份有限公司 | A kind of preparation method of styrylphenol |
| CN110981701A (en) * | 2019-12-24 | 2020-04-10 | 江苏精禾界面科技有限公司 | Method for synthesizing polystyrolated phenol |
| CN110981701B (en) * | 2019-12-24 | 2022-10-18 | 江苏精禾界面科技有限公司 | Method for synthesizing polystyrolated phenol |
| RU2802029C1 (en) * | 2023-02-21 | 2023-08-22 | Акционерное общество "Стерлитамакский нефтехимический завод" | Method for producing mixture of methyl-benzylated phenols |
| CN118084625A (en) * | 2024-01-23 | 2024-05-28 | 浙江皇马科技股份有限公司 | A kind of synthetic method of styrenated phenol |
| CN118084625B (en) * | 2024-01-23 | 2024-12-27 | 浙江皇马科技股份有限公司 | Synthesis method of styrenated phenol |
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Application publication date: 20140625 |