CN101684066A - Method for preparing dodecylphenol - Google Patents
Method for preparing dodecylphenol Download PDFInfo
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- CN101684066A CN101684066A CN200810222751A CN200810222751A CN101684066A CN 101684066 A CN101684066 A CN 101684066A CN 200810222751 A CN200810222751 A CN 200810222751A CN 200810222751 A CN200810222751 A CN 200810222751A CN 101684066 A CN101684066 A CN 101684066A
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- dodecylphenol
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Abstract
The invention relates to a method for preparing dodecylphenol, which uses phenol and triisobutene as raw materials to carry out an alkylation reaction by catalysis of a catalyst in petroleum ether solvent (indicating that when Lewis acid catalyst is used). The reacting temperature is between 20 and 90 DEG C, and the reacting time is between 2 and 10 hours; the dodecylphenol is prepared under a condition that the proportion of the phenol to the triisobutene is 2.0-10.0:1 in molar ratio. The method has the advantages that the product has the characteristics of high purity, good quality, high reaction yield, long service life of the catalyst and the like; and the preparation method can be applied in the production process of current dodecylphenol.
Description
Technical field
The invention belongs to field of fine chemical, include the preparation method of organic compounds, specifically, relate to prepare 4-dodecylphenol with the alkylated reaction of an acidic catalyst catalysis of phenol and tri-isobutylene.
Background technology
Alkylphenol is to carry out alkylated reaction by alkene, Fatty Alcohol(C12-C14 and C12-C18) or halohydrocarbon and phenol to generate, and important alkylphenol all is that alkylated reaction by phenol and alkene obtains in industrial production.Alkylphenol is not only the important intermediate of anion surfactants such as production alkylphenol polyoxyethylene nonionogenic tenside and alkylphenol polyoxyethylene sulfuric acid phosphate ester salt, also is the chemical intermediate of producing sterilant, softening agent, stablizer etc.
4-dodecylphenol is one of important source material of preparation lubricating oil additive and industrial surface activity agent etc.Because 4-dodecylphenol belongs to long chain alkylphenol, and this compounds synthetic mainly is to be that raw material and phenol carry out alkylation and synthesizes with long-chain end alkene or long-chain halohydrocarbon.The main method of producing at present both at home and abroad dodecyl phenol has following several: (1) with positive laurylene hydrocarbon as alkylating reagent catalysis synthesizing alkyl phenol.(2) with halo dodecane hydrocarbon as alkylating reagent catalysis synthesizing alkyl phenol.(3) with n-dodecanol as alkylating reagent catalysis synthesizing alkyl phenol.
At present in the preparation dodecyl phenol method, the cost height, unfavorable factor such as productive rate is low, and long reaction time and environmental pollution are big is restricting and is developing, and the alkylphenol product exists purity low, and color is dark, quality problems such as antioxidative stabilizer difference.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art part, and the preparation method of the good 4-dodecylphenol of a kind of performance is provided.
The object of the invention can realize by following measure:
The preparation method of 4-dodecylphenol of the present invention, it is in petroleum ether solvent, solvent load be 2～4 times to the liquid volume of phenol, carry out catalysis with catalyzer, catalyst levels is 5%～20% of a phenol quality, raw material is liquid phase phenol and tri-isobutylene, phenol and tri-isobutylene mol ratio are 2.0～10.0: 1, and temperature of reaction is 20～90 ℃, and the reaction times is under 2～10 hours conditions, carry out alkylated reaction, make through aftertreatment again.
Described catalyzer comprises Lewis acid, acidic resins and molecular sieve; When using lewis acid catalyst, use petroleum ether solvent.
Described catalyzer Lewis acid comprises boron trifluoride, aluminum chloride, boron trifluoride ether solution, boron trifluoride monohydrate; The acid resin of sulfonic acid vinylbenzene-diethylbenzene polymkeric substance is as Zeo-karb Amberlyst 15 and C102 macropore strong acid cation exchange resin etc.; Si-Al molecular sieve, its silica alumina ratio are 25～30, as HY molecular sieve and ZSM-5 molecular sieve etc.
Described tri-isobutylene comprises the isomers of trimerical all structures of iso-butylene, as isobutene oligomerisation laurylene hydrocarbon.
Described post-treating method: comprise while hot reaction mixture is carried out suction filtration, hot wash 4～5 times, underpressure distillation, suction, under nitrogen protection, suction filtration washs 2～3 times, underpressure distillation, lucifuge is stored, and obtains the dodecyl phenolic product.
Because of alkylphenol as a class important fine chemical material and intermediate, the quality quality of its product directly has influence on the quality height of the end product of its application, so the purpose of this invention is to provide a kind of novel method for preparing the high-quality 4-dodecylphenol.
The present invention has following advantage compared to existing technology:
1, the reaction raw materials tri-isobutylene is cheap and easy to get, has opened up new purposes for the industry byproduct tri-isobutylene, has improved the utility value of tri-isobutylene greatly.
2, solved the too high problem of present production 4-dodecylphenol cost, the raw materials used tri-isobutylene prices such as the positive laurylene hydrocarbon of present raw materials for production of comparing are cheap, greatly reduce production cost.
3, catalyst system therefor is in extensive range, be fit to most industrial manufacture process, thereby applicability is extensive.The catalyzer long service life.
4, product yield height, the purity height, quality is good, and product colour is shallow, and stability in storage is also better.
Embodiment
Enumerate 3 embodiment below, the present invention is further specified, but the present invention is not only limited to this several embodiment.
Embodiment 1:
The there-necked flask reactor that has electric mixing device and vacuum treatment installation, in 45mL sherwood oil (90～120 ℃ of boiling range sherwood oils) solvent, solvent load be 2.5 times to the liquid volume of phenol, drop into 0.2mol phenol, 1.0mL relative density is that the boron trifluoride ether solution catalyzer of 1.12-1.14 is in there-necked flask, catalyst levels is 12% of a phenol quality, after thorough mixing is even, under agitation drip the tri-isobutylene that total amount is 0.1mol, phenol and tri-isobutylene mol ratio are 2: 1, under 20 ℃ of temperature of reaction, stirring reaction carries out suction filtration with reaction mixture after 2 hours while hot, while hot filtrate is used hot wash 5 times, remove waste water.Thick product is carried out underpressure distillation, under 150 ℃ of vacuum tightness 1.3mb, temperature, obtain the cut product, at last under nitrogen protection; while hot reaction mixture is carried out suction filtration, filtrate is used hot wash 3 times, thick product carries out underpressure distillation; lucifuge is stored, and obtains the dodecyl phenolic product.
Embodiment 2:
The preparation method is identical with embodiment 1, different is replaces embodiment 1 corresponding raw material with phenol and 3g Zeo-karb Amberlyst 15 catalyzer of 0.2mol, catalyst levels is 15% of a phenol quality, the reaction environment vacuum-treat, after fully mixing under 50 ℃ of temperature, continuing to drip total amount 0.1mol tri-isobutylene under the stirring, phenol and tri-isobutylene mol ratio are 2: 1, under 50 ℃ of temperature of reaction, behind the stirring reaction 6 hours, while hot reaction mixture is carried out suction filtration, the product aftertreatment is with example 1.
Embodiment 3:
The preparation method is identical with embodiment 1, different is that 0.2mol phenol and 3g strongly-acid pure aluminium silicate bead molecular sieve catalyst are replaced embodiment 1 corresponding raw material, catalyst levels is 15% of a phenol quality, the reaction environment vacuum-treat, under 90 ℃ of temperature, after fully mixing, continuing to drip total amount under the stirring is the tri-isobutylene of 0.1mol, phenol and tri-isobutylene mol ratio are 2: 1, under 90 ℃ of temperature of reaction, behind the stirring reaction 10 hours, while hot reaction mixture is carried out suction filtration.The product aftertreatment is with example 1.
Claims (4)
1, the preparation method of 4-dodecylphenol, it is characterized in that: it is in petroleum ether solvent, solvent load be 2～4 times to the liquid volume of phenol, carry out catalysis with catalyzer, catalyst levels is 5%～20% of a phenol quality, raw material is liquid phase phenol and tri-isobutylene, phenol and tri-isobutylene mol ratio are 2.0～10.0: 1, and temperature of reaction is 20～90 ℃, and the reaction times is under 2～10 hours conditions, carry out alkylated reaction, make through aftertreatment again.
2, the preparation method of 4-dodecylphenol according to claim 1 is characterized in that: described catalyzer comprises Lewis acid, acidic resins and molecular sieve; When using lewis acid catalyst, use petroleum ether solvent.
3, the preparation method of 4-dodecylphenol according to claim 1 is characterized in that: described tri-isobutylene is an isobutene oligomerisation laurylene hydrocarbon.
4, the preparation method of 4-dodecylphenol according to claim 1; it is characterized in that: described post-treating method comprises while hot reaction mixture is carried out suction filtration; hot wash 4-5 time, underpressure distillation, suction; under nitrogen protection; suction filtration washs underpressure distillation 2-3 time; lucifuge is stored, and obtains the dodecyl phenolic product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810222751A CN101684066A (en) | 2008-09-24 | 2008-09-24 | Method for preparing dodecylphenol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810222751A CN101684066A (en) | 2008-09-24 | 2008-09-24 | Method for preparing dodecylphenol |
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| CN101684066A true CN101684066A (en) | 2010-03-31 |
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| CN200810222751A Pending CN101684066A (en) | 2008-09-24 | 2008-09-24 | Method for preparing dodecylphenol |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104387238A (en) * | 2014-10-27 | 2015-03-04 | 新乡市瑞丰化工有限责任公司 | Preparation method of branched alkyl phenol |
| CN106732685A (en) * | 2016-12-22 | 2017-05-31 | 常州大学 | A kind of catalyst and preparation method for synthesizing dodecylphenol |
| CN107649170A (en) * | 2017-09-30 | 2018-02-02 | 宝鸡文理学院 | A kind of carried molecular sieve catalyst for synthesizing the DI-tert-butylphenol compounds of 4 methyl 2,6 and its application |
| CN108929198A (en) * | 2018-08-07 | 2018-12-04 | 广东锦昱材料科技有限公司 | A kind of side chain dodecyl benzen phenol produced using three polybutene as raw material |
| CN109776600A (en) * | 2019-01-20 | 2019-05-21 | 南雄志一精细化工有限公司 | A kind of environment protection liquid phosphite antioxidant |
| CN110551004A (en) * | 2019-08-16 | 2019-12-10 | 广东新华粤石化集团股份公司 | high-performance antioxidant and preparation method thereof |
| CN113651678A (en) * | 2020-05-12 | 2021-11-16 | 中国石油化工股份有限公司 | Method for synthesizing alkylphenol and application thereof |
| CN114456042A (en) * | 2021-05-27 | 2022-05-10 | 广东新华粤石化集团股份公司 | Preparation method of p-dodecylphenol |
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| CN1185426A (en) * | 1996-01-25 | 1998-06-24 | 中国石油化工总公司 | Process for preparing alkylphenol |
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| CN1185426A (en) * | 1996-01-25 | 1998-06-24 | 中国石油化工总公司 | Process for preparing alkylphenol |
Non-Patent Citations (2)
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| 周波: "阳离子交换树脂催化合成烷基酚的研究", 《化工中间体》 * |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104387238A (en) * | 2014-10-27 | 2015-03-04 | 新乡市瑞丰化工有限责任公司 | Preparation method of branched alkyl phenol |
| CN104387238B (en) * | 2014-10-27 | 2016-05-11 | 新乡市瑞丰新材料股份有限公司 | A kind of preparation method of branched alkyl phenol |
| CN106732685A (en) * | 2016-12-22 | 2017-05-31 | 常州大学 | A kind of catalyst and preparation method for synthesizing dodecylphenol |
| CN106732685B (en) * | 2016-12-22 | 2019-07-26 | 常州大学 | A kind of catalyst and preparation method synthesizing dodecylphenol |
| CN107649170A (en) * | 2017-09-30 | 2018-02-02 | 宝鸡文理学院 | A kind of carried molecular sieve catalyst for synthesizing the DI-tert-butylphenol compounds of 4 methyl 2,6 and its application |
| CN107649170B (en) * | 2017-09-30 | 2020-02-21 | 宝鸡文理学院 | Supported molecular sieve catalyst for synthesizing 4-methyl-2, 6-di-tert-butylphenol and application thereof |
| CN108929198A (en) * | 2018-08-07 | 2018-12-04 | 广东锦昱材料科技有限公司 | A kind of side chain dodecyl benzen phenol produced using three polybutene as raw material |
| CN109776600A (en) * | 2019-01-20 | 2019-05-21 | 南雄志一精细化工有限公司 | A kind of environment protection liquid phosphite antioxidant |
| CN110551004A (en) * | 2019-08-16 | 2019-12-10 | 广东新华粤石化集团股份公司 | high-performance antioxidant and preparation method thereof |
| CN113651678A (en) * | 2020-05-12 | 2021-11-16 | 中国石油化工股份有限公司 | Method for synthesizing alkylphenol and application thereof |
| CN114456042A (en) * | 2021-05-27 | 2022-05-10 | 广东新华粤石化集团股份公司 | Preparation method of p-dodecylphenol |
| CN114456042B (en) * | 2021-05-27 | 2023-12-08 | 广东华锦达新材科技有限公司 | Preparation method of p-dodecylphenol |
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Application publication date: 20100331 |