TWI310028B - Method for the preparation of cumylphenol - Google Patents
Method for the preparation of cumylphenol Download PDFInfo
- Publication number
- TWI310028B TWI310028B TW091109262A TW91109262A TWI310028B TW I310028 B TWI310028 B TW I310028B TW 091109262 A TW091109262 A TW 091109262A TW 91109262 A TW91109262 A TW 91109262A TW I310028 B TWI310028 B TW I310028B
- Authority
- TW
- Taiwan
- Prior art keywords
- phenol
- cumene
- alkylbenzene
- methylstyrene
- catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 42
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 52
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 19
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 239000006227 byproduct Substances 0.000 claims description 9
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 claims description 9
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000011973 solid acid Substances 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 claims 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 claims 2
- 230000002079 cooperative effect Effects 0.000 claims 2
- 238000012856 packing Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 229940023913 cation exchange resins Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- -1 poly(styrene divinylbenzene) copolymer Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- IJBWMYBRNPIXJT-UHFFFAOYSA-N 2,3-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC(O)=C(C(C)(C)C=2C=CC=CC=2)C=1C(C)(C)C1=CC=CC=C1 IJBWMYBRNPIXJT-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- NMEYYHCPJZHSIC-UHFFFAOYSA-N CC=CC1=CC=CC=C1.C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound CC=CC1=CC=CC=C1.C1=CC=CC=2C3=CC=CC=C3CC12 NMEYYHCPJZHSIC-UHFFFAOYSA-N 0.000 description 1
- JJRPCZQADYJJRA-UHFFFAOYSA-N Cc1c(C)c(O)c(c(C)c1O)-c1ccccc1 Chemical compound Cc1c(C)c(O)c(c(C)c1O)-c1ccccc1 JJRPCZQADYJJRA-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29139101P | 2001-05-16 | 2001-05-16 | |
| US09/683,786 US6448453B1 (en) | 2001-05-16 | 2002-02-14 | Method for the preparation of cumylphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI310028B true TWI310028B (en) | 2009-05-21 |
Family
ID=26966744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091109262A TWI310028B (en) | 2001-05-16 | 2002-05-03 | Method for the preparation of cumylphenol |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6448453B1 (https=) |
| EP (1) | EP1399404B1 (https=) |
| JP (1) | JP4098634B2 (https=) |
| KR (1) | KR100871212B1 (https=) |
| CN (1) | CN1235848C (https=) |
| DE (1) | DE60228444D1 (https=) |
| TW (1) | TWI310028B (https=) |
| WO (1) | WO2002092546A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6495034B1 (en) * | 2001-05-23 | 2002-12-17 | Daniel Lee Schmidtke | Swimming pool valve system |
| RU2217409C2 (ru) | 2002-02-08 | 2003-11-27 | Общество с ограниченной ответственностью "Петрофенол" | Способ и катализатор получения паракумилфенола |
| RU2217408C2 (ru) * | 2002-02-08 | 2003-11-27 | Общество с ограниченной ответственностью "Петрофенол" | Способ и катализатор очистки фенола |
| JP2005526718A (ja) * | 2002-02-08 | 2005-09-08 | ゼネラル・エレクトリック・カンパニイ | フェノールの精製方法及び触媒 |
| CN116897145A (zh) * | 2021-02-23 | 2023-10-17 | 科思创德国股份有限公司 | 在α-甲基苯乙烯的存在下制备双酚A(BPA)的方法 |
| CN115636731B (zh) * | 2022-10-14 | 2024-04-09 | 宿迁联盛科技股份有限公司 | 一种2,4-二枯基苯酚的合成方法 |
| CN115850029B (zh) * | 2022-12-09 | 2023-07-07 | 江苏极易新材料有限公司 | 一种2,4-二枯基酚的合成方法 |
| CN116283504B (zh) * | 2023-03-13 | 2023-10-10 | 江苏极易新材料有限公司 | 一种2,4-二枯基酚的合成方法 |
| CN117658778A (zh) * | 2023-12-06 | 2024-03-08 | 哈尔滨市润合新材料有限公司 | 2，4-二枯基苯酚的合成精制方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2882322A (en) * | 1957-01-23 | 1959-04-14 | Allied Chem | Production of cumylphenol from alpha-methylstyrene dimer |
| PL110645B2 (en) * | 1978-08-04 | 1980-07-31 | Inst Chemii Przemyslowej | Method of obtaining p-cumylophenol and cumene from hydrocarbon fraction obtained as by-product at the manufacture of phenol by cumene process |
| JPS63208545A (ja) | 1987-02-23 | 1988-08-30 | Mitsubishi Petrochem Co Ltd | パラクミルフエノ−ルの製造法 |
| PL158448B1 (pl) * | 1988-11-11 | 1992-09-30 | Inst Chemii Przemyslowej | Sposób otrzymywania kumylofenolu i/lub jego metylowych pochodnych PL PL PL PL PL |
| US5091058A (en) | 1990-02-20 | 1992-02-25 | Aristech Chemical Corporation | Purified para-cumylphenol |
| US5304689A (en) | 1992-06-01 | 1994-04-19 | General Electric Company | Stabilization of color in production of paracumylphenol using hypophosphorous acid |
| US5185475A (en) | 1992-06-01 | 1993-02-09 | General Electric Company | Process for preparing paracumylphenol |
-
2002
- 2002-02-14 US US09/683,786 patent/US6448453B1/en not_active Expired - Lifetime
- 2002-05-01 KR KR1020037014625A patent/KR100871212B1/ko not_active Expired - Lifetime
- 2002-05-01 EP EP02734164A patent/EP1399404B1/en not_active Expired - Lifetime
- 2002-05-01 DE DE60228444T patent/DE60228444D1/de not_active Expired - Lifetime
- 2002-05-01 CN CNB028100883A patent/CN1235848C/zh not_active Expired - Lifetime
- 2002-05-01 JP JP2002589432A patent/JP4098634B2/ja not_active Expired - Lifetime
- 2002-05-01 WO PCT/US2002/013997 patent/WO2002092546A1/en not_active Ceased
- 2002-05-03 TW TW091109262A patent/TWI310028B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002092546A1 (en) | 2002-11-21 |
| KR20030094400A (ko) | 2003-12-11 |
| KR100871212B1 (ko) | 2008-12-01 |
| EP1399404A1 (en) | 2004-03-24 |
| US6448453B1 (en) | 2002-09-10 |
| CN1235848C (zh) | 2006-01-11 |
| DE60228444D1 (de) | 2008-10-02 |
| JP4098634B2 (ja) | 2008-06-11 |
| JP2004527574A (ja) | 2004-09-09 |
| CN1509265A (zh) | 2004-06-30 |
| EP1399404B1 (en) | 2008-08-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Expiration of patent term of an invention patent |