CN103880603A - Method for preparing styrenated phenol by catalysis - Google Patents

Method for preparing styrenated phenol by catalysis Download PDF

Info

Publication number
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
Authority
CN
China
Prior art keywords
phenol
catalysis
styrenated phenol
reaction
prepared
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.)
Pending
Application number
CN201410115083.9A
Other languages
Chinese (zh)
Inventor
王德堂
李敢
王峰
肖先举
夏先伟
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xuzhou College of Industrial Technology
Original Assignee
Xuzhou College of Industrial Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Xuzhou College of Industrial Technology filed Critical Xuzhou College of Industrial Technology
Priority to CN201410115083.9A priority Critical patent/CN103880603A/en
Publication of CN103880603A publication Critical patent/CN103880603A/en
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11Preparation 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
    • C07C37/14Preparation 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

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

The method of styrenated phenol is prepared in a kind of catalysis
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 ℃.
CN201410115083.9A 2014-03-25 2014-03-25 Method for preparing styrenated phenol by catalysis Pending CN103880603A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201410115083.9A CN103880603A (en) 2014-03-25 2014-03-25 Method for preparing styrenated phenol by catalysis

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201410115083.9A CN103880603A (en) 2014-03-25 2014-03-25 Method for preparing styrenated phenol by catalysis

Publications (1)

Publication Number Publication Date
CN103880603A true CN103880603A (en) 2014-06-25

Family

ID=50949773

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201410115083.9A Pending CN103880603A (en) 2014-03-25 2014-03-25 Method for preparing styrenated phenol by catalysis

Country Status (1)

Country Link
CN (1) CN103880603A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
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

Citations (2)

* Cited by examiner, † Cited by third party
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
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 (4)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
CN103880603A (en) Method for preparing styrenated phenol by catalysis
CN101514187B (en) Method for producing ethoxyquinoline
CN105330592A (en) Preparation method of 2-chloro-5-picoline
CN104341281A (en) 2, 6-di-tert-butyl-4-(2-methoxyphenylmethylene)-2, 5-cyclohexadiene-1-one and preparation method thereof
CN102167658A (en) Technology for complexing, crystallizing, separating and purifying metacresol
CN103394370A (en) Silica gel-supported sulfonic acid dual-core ionic liquid catalyst, and preparation method and application thereof
CN105777643A (en) Method using immobilized ionic liquid as catalyst to synthesize lubricant base oil
CN104592166B (en) A kind of Supported on Zeolite process for catalytic synthesis of glycidyl allyl ether
CN105418470A (en) Synthetic method of clethodim
CN105646172A (en) 1-hydroxy cyclohexyl phenyl methanone synthesis process
CN102584696A (en) Catalytic synthesis method for rubber antioxidant RD
CN104230983A (en) Production method of tributyl phosphate
CN104326989B (en) The preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine
CN105523982A (en) Method for preparing tert-butyl hydroperoxide
CN104557538A (en) Industrial production method for producing butyl acrylate by in-column reaction rectification
CN102069010B (en) Montmorillonite catalyst used in preparation of cyclic carbonate
CN103319312A (en) Joint production process of antioxidant 264 and 6-tertiary butyl m-cresol
CN107032984A (en) A kind of method that continuous catalyzing rectifying prepares ethyl lactate
CN102010322A (en) Method for preparing dimer acid with light color, low iron and low phosphorus
CN105524237A (en) Synthetic method for phenolic resin
CN109810011A (en) A kind of preparation method of N- isobornyl amide
CN101684067A (en) Antioxidant 1790 intermediate and clean production method thereof
CN204939337U (en) A kind of device of tetraline of purifying from coking crude benzene hydrogenation liquid
CN103524323B (en) Method for catalytically synthesizing o-benzoylbenzoic acid by virtue of metal oxide supported solid superacid
CN103073407A (en) Method for preparing 2, 4-dihydroxy benaophenonel by using indium trichloride to catalyze

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C02 Deemed withdrawal of patent application after publication (patent law 2001)
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20140625