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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- CN
- China
- Prior art keywords
- dodecylphenol
- phenol
- isobutylene
- catalyst
- preparation
- 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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- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 239000003208 petroleum Substances 0.000 claims abstract description 4
- 230000035484 reaction time Effects 0.000 claims abstract description 4
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 3
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 3
- 238000000967 suction filtration Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000002808 molecular sieve Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims 1
- 229940069096 dodecene Drugs 0.000 claims 1
- 238000012805 post-processing Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000005516 engineering process Methods 0.000 abstract description 3
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 8
- -1 polyoxyethylene Polymers 0.000 description 7
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 150000005826 halohydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- NKBWAYZCDQRZEJ-UHFFFAOYSA-N C=CC1=CC=CC=C1.CCC1=CC=CC=C1CC Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1CC NKBWAYZCDQRZEJ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229910002796 Si–Al Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- MVJKXJPDBTXECY-UHFFFAOYSA-N trifluoroborane;hydrate Chemical compound O.FB(F)F MVJKXJPDBTXECY-UHFFFAOYSA-N 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及十二烷基酚的制备方法，在石油醚溶剂中(指使用路易斯酸催化剂时)，由催化剂催化，原料为苯酚和三聚异丁烯，进行烷基化反应。反应温度为20～90℃，反应时间为2～10小时，苯酚和三聚异丁烯比为2.0～10.0∶1(摩尔比)条件下制得，本发明优点是产品纯度高，质量好，反应收率高，催化剂使用寿命长等特点，本发明的制备方法可应用于现行十二烷基酚的生产工艺中。The invention relates to a preparation method of dodecylphenol, which is carried out in a petroleum ether solvent (when Lewis acid catalyst is used), catalyzed by a catalyst, and the raw materials are phenol and trimerized isobutylene, and the alkylation reaction is carried out. The reaction temperature is 20-90°C, the reaction time is 2-10 hours, and the ratio of phenol and trimerized isobutylene is 2.0-10.0:1 (molar ratio). High efficiency, long service life of catalyst and other characteristics, the preparation method of the present invention can be applied in the production technology of existing 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810222751A CN101684066A (en) | 2008-09-24 | 2008-09-24 | Method for preparing dodecylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810222751A CN101684066A (en) | 2008-09-24 | 2008-09-24 | Method for preparing dodecylphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101684066A true CN101684066A (en) | 2010-03-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810222751A Pending CN101684066A (en) | 2008-09-24 | 2008-09-24 | Method for preparing dodecylphenol |
Country Status (1)
| Country | Link |
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| CN (1) | CN101684066A (en) |
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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2008
- 2008-09-24 CN CN200810222751A patent/CN101684066A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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)
| Title |
|---|
| 周波: "阳离子交换树脂催化合成烷基酚的研究", 《化工中间体》 * |
| 李杰等: "苯酚烷基化催化剂研究进展", 《应用化工》 * |
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 for synthesizing dodecyl phenol and preparation method |
| 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 | A kind of supported molecular sieve catalyst for synthesizing 4-methyl-2,6-di-tert-butylphenol 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 |
| 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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