CN101161616A - 对-特辛基苯酚的制备方法 - Google Patents
对-特辛基苯酚的制备方法 Download PDFInfo
- Publication number
- CN101161616A CN101161616A CNA2007101902775A CN200710190277A CN101161616A CN 101161616 A CN101161616 A CN 101161616A CN A2007101902775 A CNA2007101902775 A CN A2007101902775A CN 200710190277 A CN200710190277 A CN 200710190277A CN 101161616 A CN101161616 A CN 101161616A
- Authority
- CN
- China
- Prior art keywords
- tert
- octylphenol
- phenol
- exchange resin
- iso
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 title abstract 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical class CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 43
- 230000029936 alkylation Effects 0.000 claims abstract description 37
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 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 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 239000002168 alkylating agent Substances 0.000 claims abstract description 8
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 238000007872 degassing Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 claims description 18
- 229920001577 copolymer Polymers 0.000 claims description 15
- 238000005520 cutting process Methods 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 7
- -1 phenylethylene-divinyl Chemical class 0.000 claims description 7
- 239000012154 double-distilled water Substances 0.000 claims description 6
- 239000011973 solid acid Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 239000012085 test solution Substances 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 230000001131 transforming effect Effects 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 18
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 abstract 3
- 239000000047 product Substances 0.000 description 8
- 244000286663 Ficus elastica Species 0.000 description 4
- 238000007171 acid catalysis Methods 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229920003051 synthetic elastomer Polymers 0.000 description 4
- 239000005061 synthetic rubber Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010091 synthetic rubber production Methods 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2007101902775A CN101161616B (zh) | 2007-11-26 | 2007-11-26 | 对-特辛基苯酚的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2007101902775A CN101161616B (zh) | 2007-11-26 | 2007-11-26 | 对-特辛基苯酚的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101161616A true CN101161616A (zh) | 2008-04-16 |
CN101161616B CN101161616B (zh) | 2010-12-29 |
Family
ID=39296607
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN2007101902775A Active CN101161616B (zh) | 2007-11-26 | 2007-11-26 | 对-特辛基苯酚的制备方法 |
Country Status (1)
Country | Link |
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CN (1) | CN101161616B (zh) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103274903A (zh) * | 2013-06-26 | 2013-09-04 | 杨锌荣 | 一种对烷基苯酚及其制备方法 |
US20140080965A1 (en) * | 2012-09-17 | 2014-03-20 | Sino Legend (Zhangjiagang) Chemical Co. Ltd. | Alkyl Phenolic Resin and Method of Preparation Thereof |
US9932436B2 (en) | 2013-10-17 | 2018-04-03 | Si Group, Inc. | Modified alkylphenol-aldehyde resins stabilized by a salicylic acid |
US9944744B2 (en) | 2013-10-17 | 2018-04-17 | Si Group, Inc. | In-situ alkylphenol-aldehyde resins |
CN109880031A (zh) * | 2018-12-07 | 2019-06-14 | 山东阳谷华泰化工股份有限公司 | 一种混合烷基苯酚-甲醛树脂橡胶增粘剂的制备方法 |
CN112110799A (zh) * | 2020-09-25 | 2020-12-22 | 药大制药有限公司 | 一种辛苯聚醇的制备方法 |
CN113072429A (zh) * | 2021-03-31 | 2021-07-06 | 淄博旭佳化工有限公司 | 对-特辛基苯酚连续生产工艺及装置 |
-
2007
- 2007-11-26 CN CN2007101902775A patent/CN101161616B/zh active Active
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20140080965A1 (en) * | 2012-09-17 | 2014-03-20 | Sino Legend (Zhangjiagang) Chemical Co. Ltd. | Alkyl Phenolic Resin and Method of Preparation Thereof |
US9133294B2 (en) * | 2012-09-17 | 2015-09-15 | Sino Legend (China) Chemical Co. Ltd. | Alkyl phenolic resin and method of preparation thereof |
CN103274903A (zh) * | 2013-06-26 | 2013-09-04 | 杨锌荣 | 一种对烷基苯酚及其制备方法 |
US9932436B2 (en) | 2013-10-17 | 2018-04-03 | Si Group, Inc. | Modified alkylphenol-aldehyde resins stabilized by a salicylic acid |
US9944744B2 (en) | 2013-10-17 | 2018-04-17 | Si Group, Inc. | In-situ alkylphenol-aldehyde resins |
US10647806B2 (en) | 2013-10-17 | 2020-05-12 | Si Group, Inc. | In-situ alkylphenol-aldehyde resins |
US11155667B2 (en) | 2013-10-17 | 2021-10-26 | Si Group, Inc. | In-situ alkylphenol-aldehyde resins |
US12012487B2 (en) | 2013-10-17 | 2024-06-18 | Si Group, Inc. | In-situ alkylphenol-aldehyde resins |
CN109880031A (zh) * | 2018-12-07 | 2019-06-14 | 山东阳谷华泰化工股份有限公司 | 一种混合烷基苯酚-甲醛树脂橡胶增粘剂的制备方法 |
CN109880031B (zh) * | 2018-12-07 | 2021-11-02 | 山东阳谷华泰化工股份有限公司 | 一种混合烷基苯酚-甲醛树脂橡胶增粘剂的制备方法 |
CN112110799A (zh) * | 2020-09-25 | 2020-12-22 | 药大制药有限公司 | 一种辛苯聚醇的制备方法 |
CN113072429A (zh) * | 2021-03-31 | 2021-07-06 | 淄博旭佳化工有限公司 | 对-特辛基苯酚连续生产工艺及装置 |
Also Published As
Publication number | Publication date |
---|---|
CN101161616B (zh) | 2010-12-29 |
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Effective date of registration: 20130626 Address after: 200120 Shanghai, Pudong New Area Garden Road, No. 33, CITIGROUP TOWER, building 901, room 9 Patentee after: Shanghai Tongcheng Chemical Co., Ltd. Address before: 212211 Jiangsu city of Yangzhong Province in the new road Xinba No. 25 Patentee before: Tong Yue Chemical (Yangzhong) Co., Ltd. |
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Application publication date: 20080416 Assignee: Red Avenue Chemical (Shanghai) Co.,Ltd. Assignor: Shanghai Tongcheng Chemical Co., Ltd. Contract record no.: 2014990000378 Denomination of invention: Method for preparing p-tert octyl phenol Granted publication date: 20101229 License type: Exclusive License Record date: 20140606 |
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Effective date of registration: 20170309 Address after: 201507 Shanghai Chemical Industrial Zone, North Galaxy Road, No. 66 Patentee after: Tongcheng Chemical Co. Ltd. (China) Address before: 200120 Shanghai, Pudong New Area Garden Road, No. 33, CITIGROUP TOWER, building 901, room 9 Patentee before: Shanghai Tongcheng Chemical Co., Ltd. |
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