DE3941472C1 - - Google Patents
Info
- Publication number
- DE3941472C1 DE3941472C1 DE3941472A DE3941472A DE3941472C1 DE 3941472 C1 DE3941472 C1 DE 3941472C1 DE 3941472 A DE3941472 A DE 3941472A DE 3941472 A DE3941472 A DE 3941472A DE 3941472 C1 DE3941472 C1 DE 3941472C1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butylphenol
- isobutene
- mol
- catalyst
- 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.)
- Expired - Fee Related
Links
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 90
- 239000003054 catalyst Substances 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 32
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 30
- 229910052782 aluminium Inorganic materials 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 25
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims description 23
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 23
- 238000005804 alkylation reaction Methods 0.000 claims description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 14
- 230000029936 alkylation Effects 0.000 claims description 13
- 239000007983 Tris buffer Substances 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Chemical compound CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 0.000 claims description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 6
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- UPIWSWBNCDDIMU-UHFFFAOYSA-K aluminum;2-tert-butylphenolate Chemical compound [Al+3].CC(C)(C)C1=CC=CC=C1[O-].CC(C)(C)C1=CC=CC=C1[O-].CC(C)(C)C1=CC=CC=C1[O-] UPIWSWBNCDDIMU-UHFFFAOYSA-K 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 11
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical class [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 9
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 8
- -1 C12 cycloalkenes Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 230000020335 dealkylation Effects 0.000 description 2
- 238000006900 dealkylation reaction Methods 0.000 description 2
- 238000007700 distillative separation Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010555 transalkylation reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AFRNIXXHPVFSHY-UHFFFAOYSA-K aluminum;phenol;triphenoxide Chemical compound [Al+3].OC1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 AFRNIXXHPVFSHY-UHFFFAOYSA-K 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000010626 work up procedure Methods 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3941472A DE3941472C1 (US07413550-20080819-C00001.png) | 1989-12-15 | 1989-12-15 | |
| EP19900119868 EP0438641A3 (en) | 1989-12-15 | 1990-10-17 | Process for preparing 2,6-di-tert.butylphenol |
| US07/625,400 US5091594A (en) | 1989-12-15 | 1990-12-11 | Process for the production of 2,6-di-tert-butylphenol |
| JP2402236A JPH05132439A (ja) | 1989-12-15 | 1990-12-14 | ２，６−ジ−第三ブチルフエノールの製造方法 |
| SU904831918A RU1833357C (ru) | 1989-12-15 | 1990-12-14 | Cпocoб пoлучehия 2,6-ди-tpet-буtилфehoлa |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3941472A DE3941472C1 (US07413550-20080819-C00001.png) | 1989-12-15 | 1989-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3941472C1 true DE3941472C1 (US07413550-20080819-C00001.png) | 1991-02-21 |
Family
ID=6395546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3941472A Expired - Fee Related DE3941472C1 (US07413550-20080819-C00001.png) | 1989-12-15 | 1989-12-15 |
Country Status (5)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4139056A1 (de) * | 1991-11-28 | 1993-06-03 | Huels Chemische Werke Ag | Verfahren zur herstellung von ortho-substituierten alkylphenolen und katalysator hierfuer |
| US5475156A (en) * | 1994-06-06 | 1995-12-12 | General Electric Company | Method for making a 2,6-dialkylphenol |
| EP1931613B1 (en) * | 2005-09-12 | 2015-11-11 | FujiFilm Electronic Materials USA, Inc. | Additives to prevent degradation of cyclic alkene derivatives |
| TWI411663B (zh) * | 2005-09-12 | 2013-10-11 | Fujifilm Electronic Materials | 防止環烯烴衍生物降解之添加劑（二） |
| CN102089405B (zh) | 2008-07-08 | 2013-10-16 | 富士胶片电子材料美国有限公司 | 防止环烯烃衍生物降解的添加剂 |
| TWI624450B (zh) * | 2009-12-04 | 2018-05-21 | Ｓｉ集團股份有限公司 | 從ｃ萃餘物之物流製造三級丁基酚之方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355504A (en) * | 1963-11-05 | 1967-11-28 | Ethyl Corp | Preparation of 2, 6-dialkyl phenols |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB843745A (en) * | 1957-10-21 | 1960-08-10 | Bataafsche Petroleum | Process for the preparation of 2, 6-dialkyl phenols |
| GB1229480A (US07413550-20080819-C00001.png) * | 1967-11-20 | 1971-04-21 | ||
| US4631349A (en) * | 1985-06-25 | 1986-12-23 | Ethyl Corporation | Heterogeneous catalyst process |
| US4870215A (en) * | 1988-06-24 | 1989-09-26 | Ethyl Corporation | Phenol alkylation process |
| JPH03188635A (ja) * | 1989-12-18 | 1991-08-16 | Matsushita Electron Corp | 半導体装置のバンプレベリング方法および製造装置 |
-
1989
- 1989-12-15 DE DE3941472A patent/DE3941472C1/de not_active Expired - Fee Related
-
1990
- 1990-10-17 EP EP19900119868 patent/EP0438641A3/de not_active Withdrawn
- 1990-12-11 US US07/625,400 patent/US5091594A/en not_active Expired - Fee Related
- 1990-12-14 RU SU904831918A patent/RU1833357C/ru active
- 1990-12-14 JP JP2402236A patent/JPH05132439A/ja not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355504A (en) * | 1963-11-05 | 1967-11-28 | Ethyl Corp | Preparation of 2, 6-dialkyl phenols |
| DE1493622B1 (de) * | 1963-11-05 | 1970-06-04 | Ethyl Corp | Verfahren zur Herstellung von 2,6-Di-tertiaer-butylphenol |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0438641A2 (de) | 1991-07-31 |
| JPH05132439A (ja) | 1993-05-28 |
| US5091594A (en) | 1992-02-25 |
| RU1833357C (ru) | 1993-08-07 |
| EP0438641A3 (en) | 1992-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |