SA110310888B1 - عملية لإنتاج ثلاثي-بيوتيل فينول من تيار c4 مكرر مُصفّى - Google Patents
عملية لإنتاج ثلاثي-بيوتيل فينول من تيار c4 مكرر مُصفّى Download PDFInfo
- Publication number
- SA110310888B1 SA110310888B1 SA110310888A SA110310888A SA110310888B1 SA 110310888 B1 SA110310888 B1 SA 110310888B1 SA 110310888 A SA110310888 A SA 110310888A SA 110310888 A SA110310888 A SA 110310888A SA 110310888 B1 SA110310888 B1 SA 110310888B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- phenol
- tert
- isobutylene
- butyl
- stream
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 65
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 title claims abstract description 62
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 110
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 106
- 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 abstract description 13
- 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 claims abstract description 10
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000010555 transalkylation reaction Methods 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 95
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 34
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 26
- -1 methyl-tert-amyl Chemical group 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- GJYCVCVHRSWLNY-UHFFFAOYSA-N ortho-butylphenol Natural products CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical class CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 claims description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 12
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- GAZYKNYEOMWYSH-UHFFFAOYSA-N 2-methylprop-1-ene;phenol Chemical compound CC(C)=C.OC1=CC=CC=C1 GAZYKNYEOMWYSH-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- GFJUOMJGSXRJJY-UHFFFAOYSA-N 2-methylprop-1-ene Chemical group CC(C)=C.CC(C)=C GFJUOMJGSXRJJY-UHFFFAOYSA-N 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 229960002685 biotin Drugs 0.000 claims description 2
- 239000011616 biotin Substances 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- CFMPJDZMPSMWFA-UHFFFAOYSA-N 2-tert-butylphenol;2,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O.CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O CFMPJDZMPSMWFA-UHFFFAOYSA-N 0.000 claims 1
- 229930185605 Bisphenol Natural products 0.000 claims 1
- 244000035744 Hura crepitans Species 0.000 claims 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 claims 1
- FTDXCHCAMNRNNY-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1 FTDXCHCAMNRNNY-UHFFFAOYSA-N 0.000 claims 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 29
- 125000001424 substituent group Chemical group 0.000 abstract 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 24
- 150000002989 phenols Chemical class 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- 239000001282 iso-butane Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 9
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 229910044991 metal oxide Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 150000004706 metal oxides Chemical class 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 5
- YICCTZQUAAGDTO-UHFFFAOYSA-N but-1-ene Chemical compound CCC=C.CCC=C YICCTZQUAAGDTO-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 235000013844 butane Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 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 2
- XWJOMKZLRRTRMF-UHFFFAOYSA-N 1-butan-2-ylcyclohexa-2,4-dien-1-ol Chemical class CCC(C)C1(O)CC=CC=C1 XWJOMKZLRRTRMF-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 239000004743 Polypropylene Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001615 biotins Chemical class 0.000 description 2
- OEBDHTUOPNIHHZ-UHFFFAOYSA-N but-1-ene;phenol Chemical compound CCC=C.OC1=CC=CC=C1 OEBDHTUOPNIHHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003344 environmental pollutant Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 231100000719 pollutant Toxicity 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000013014 purified material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JKFZLMPBXBMSPD-UHFFFAOYSA-N 2-butan-2-yl-4-tert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=CC=C1O JKFZLMPBXBMSPD-UHFFFAOYSA-N 0.000 description 1
- JRJPHGWSSVDRKU-UHFFFAOYSA-N 2-butylphenol 2-tert-butylphenol Chemical compound C(C)(C)(C)C1=C(C=CC=C1)O.C(CCC)C1=C(C=CC=C1)O JRJPHGWSSVDRKU-UHFFFAOYSA-N 0.000 description 1
- JEAKTLDJVSMBKC-UHFFFAOYSA-N 2-methylpropane;2-methylprop-1-ene Chemical compound CC(C)C.CC(C)=C JEAKTLDJVSMBKC-UHFFFAOYSA-N 0.000 description 1
- XMBPQAIGZIPTLW-UHFFFAOYSA-N 4-butan-2-yl-2-butylphenol Chemical compound CCCCC1=CC(C(C)CC)=CC=C1O XMBPQAIGZIPTLW-UHFFFAOYSA-N 0.000 description 1
- SWFBLHGSXAJLIV-UHFFFAOYSA-N C(C)(C)(C)C1=C(C=CC=C1)O.CC(C)=C Chemical class C(C)(C)(C)C1=C(C=CC=C1)O.CC(C)=C SWFBLHGSXAJLIV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- IUFXKTIZXZVLJC-UHFFFAOYSA-N buta-1,3-diene;2-methylprop-1-ene Chemical compound CC(C)=C.C=CC=C IUFXKTIZXZVLJC-UHFFFAOYSA-N 0.000 description 1
- 230000006208 butylation Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZONVIFVBWLLLNU-UHFFFAOYSA-H dialuminum hexaphenoxide Chemical compound [O-]C1=CC=CC=C1.[Al+3].[Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZONVIFVBWLLLNU-UHFFFAOYSA-H 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- WZUXNWXRMLSPIP-UHFFFAOYSA-N hexan-1-ol;methanol Chemical compound OC.CCCCCCO WZUXNWXRMLSPIP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- BRSDPVLOTZLFFV-UHFFFAOYSA-N methanol;2-methylprop-1-ene Chemical compound OC.CC(C)=C BRSDPVLOTZLFFV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/88—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26682809P | 2009-12-04 | 2009-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SA110310888B1 true SA110310888B1 (ar) | 2014-06-18 |
Family
ID=43607992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SA110310888A SA110310888B1 (ar) | 2009-12-04 | 2010-12-01 | عملية لإنتاج ثلاثي-بيوتيل فينول من تيار c4 مكرر مُصفّى |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8937201B2 (enExample) |
| EP (2) | EP2521706A2 (enExample) |
| JP (2) | JP5851415B2 (enExample) |
| KR (1) | KR101822607B1 (enExample) |
| CN (1) | CN102906059B (enExample) |
| BR (1) | BR112012013419C8 (enExample) |
| ES (1) | ES2647102T3 (enExample) |
| PL (1) | PL2657217T3 (enExample) |
| PT (1) | PT2657217T (enExample) |
| RU (1) | RU2606130C2 (enExample) |
| SA (1) | SA110310888B1 (enExample) |
| SG (1) | SG181078A1 (enExample) |
| TW (2) | TWI624450B (enExample) |
| WO (1) | WO2011069052A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9932436B2 (en) | 2013-10-17 | 2018-04-03 | Si Group, Inc. | Modified alkylphenol-aldehyde resins stabilized by a salicylic acid |
| WO2015057879A1 (en) | 2013-10-17 | 2015-04-23 | Si Group, Inc. | In-situ alkylphenol-aldehyde resins |
| WO2015094571A1 (en) * | 2013-12-20 | 2015-06-25 | Exxonmobil Chemical Patents Inc. | Phenol composition |
| US9434668B1 (en) | 2015-04-09 | 2016-09-06 | Council Of Scientific And Industrial Research | Process for the production of tertiary butyl phenols |
| CN108026010A (zh) * | 2015-09-11 | 2018-05-11 | 巴斯夫欧洲公司 | 用于酚的烷基化的方法 |
| CN106975517A (zh) * | 2017-05-16 | 2017-07-25 | 同济大学 | 一种绿色高效合成2,4‑二叔丁基苯酚的多相催化剂 |
| CN113636916B (zh) * | 2021-09-17 | 2023-08-29 | 陕西万汇能聚科技有限公司 | 一种合成2,4,6-三叔丁基苯酚的方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2353282A (en) | 1941-10-15 | 1944-07-11 | Bakelite Corp | Preparation of substituted phenols |
| US2430190A (en) * | 1943-08-30 | 1947-11-04 | Universal Oil Prod Co | Alkylation of phenols |
| GB655124A (en) | 1948-06-16 | 1951-07-11 | Standard Oil Dev Co | Improvements in or relating to the preparation of poly-tert-butyl phenol or cresols |
| US3670030A (en) * | 1970-02-20 | 1972-06-13 | Universal Oil Prod Co | Alkylation of phenolic compound |
| US3751509A (en) * | 1972-07-17 | 1973-08-07 | A Liakumovich | Process for isolating isobutylene from butane-butylene fraction |
| SU783297A1 (ru) * | 1976-08-11 | 1980-11-30 | Стерлитамакский опытно-промышленный нефтехимический завод | Способ получени 2,6-ди-третбутилфенола |
| US4166191A (en) | 1976-09-20 | 1979-08-28 | Hitachi Chemical Company, Ltd. | Process for producing highly pure p-tertiary-butyl phenol |
| DE2745589C3 (de) * | 1977-10-11 | 1980-03-27 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von p-Alkylphenolen |
| JPS6052688B2 (ja) | 1977-11-18 | 1985-11-20 | 三井化学株式会社 | フエノ−ルのアルキル化方法 |
| US4260833A (en) | 1979-11-30 | 1981-04-07 | Uop Inc. | Preparation of alkylphenols |
| JPS6052732B2 (ja) | 1980-12-05 | 1985-11-21 | 三井化学株式会社 | ２，６−ジ−ｔ−ブチルフエノ−ルの製造方法 |
| JPS5852234A (ja) * | 1981-09-21 | 1983-03-28 | Yotsukaichi Gosei Kk | パラタ−シヤリプチルフエノ−ルの製造法 |
| JPS61200934A (ja) * | 1985-03-02 | 1986-09-05 | Maruzen Sekiyu Kagaku Kk | ｔｅｒｔ―ブチルフエノール類の製造方法 |
| US4631349A (en) * | 1985-06-25 | 1986-12-23 | Ethyl Corporation | Heterogeneous catalyst process |
| JPH07108870B2 (ja) | 1986-12-23 | 1995-11-22 | 三井石油化学工業株式会社 | ２，４−ジ−ｔ−ブチルフエノ−ルの製造方法 |
| US4731492A (en) * | 1987-03-04 | 1988-03-15 | Ethyl Corporation | Phenol alkylation process |
| DE3941472C1 (enExample) * | 1989-12-15 | 1991-02-21 | Huels Ag, 4370 Marl, De | |
| CS276820B6 (cs) * | 1990-05-28 | 1992-08-12 | Slovenska Technicke Univerzita | Sposob alkylácie a/alebo arylalkylácie fenolu a/alebo jeho derivátov |
| DE4139056A1 (de) * | 1991-11-28 | 1993-06-03 | Huels Chemische Werke Ag | Verfahren zur herstellung von ortho-substituierten alkylphenolen und katalysator hierfuer |
| JPH05294865A (ja) * | 1992-04-15 | 1993-11-09 | Dainippon Ink & Chem Inc | ２，４−ジ（ｔ−ブチル）フェノールの製法 |
| BR9202890A (pt) | 1992-07-22 | 1994-02-01 | Rhodia | Aperfeicoamento em processo para obtencao de terciobutilfenois |
| ES2190228T5 (es) * | 1998-09-03 | 2007-10-16 | Crompton Corporation | Purificacion de 2,4,6-tri-(ter.-butil)fenol por cristalizacion-fusion. |
| RU2164509C1 (ru) * | 1999-08-06 | 2001-03-27 | ООО "Синтезхим Бис" | Способ получения 2,6-ди-трет-бутил-фенола |
| JP2002241334A (ja) * | 2001-02-15 | 2002-08-28 | Sumitomo Chem Co Ltd | ｔｅｒｔ−ブチルフェノール類の製造方法 |
| CN1844071A (zh) * | 2006-03-24 | 2006-10-11 | 北京极易化工有限公司 | 一种高转化率高选择性的苯酚邻位烷基化方法 |
| CN1935763A (zh) * | 2006-10-20 | 2007-03-28 | 上海金海雅宝精细化工有限公司 | 一种2.4－二叔丁基苯酚烷化液的制备方法 |
| CN101092331A (zh) * | 2007-07-06 | 2007-12-26 | 宁波金海雅宝化工有限公司 | 一种固定床合成烷基酚的方法 |
-
2010
- 2010-11-29 TW TW105131059A patent/TWI624450B/zh not_active IP Right Cessation
- 2010-11-29 TW TW099141217A patent/TWI570102B/zh not_active IP Right Cessation
- 2010-12-01 SA SA110310888A patent/SA110310888B1/ar unknown
- 2010-12-03 BR BR112012013419A patent/BR112012013419C8/pt not_active IP Right Cessation
- 2010-12-03 EP EP10788470A patent/EP2521706A2/en not_active Withdrawn
- 2010-12-03 EP EP13168390.6A patent/EP2657217B1/en not_active Not-in-force
- 2010-12-03 CN CN201080054733.3A patent/CN102906059B/zh not_active Expired - Fee Related
- 2010-12-03 RU RU2012127805A patent/RU2606130C2/ru active
- 2010-12-03 SG SG2012038782A patent/SG181078A1/en unknown
- 2010-12-03 PL PL13168390T patent/PL2657217T3/pl unknown
- 2010-12-03 ES ES13168390.6T patent/ES2647102T3/es active Active
- 2010-12-03 WO PCT/US2010/058866 patent/WO2011069052A2/en not_active Ceased
- 2010-12-03 JP JP2012542218A patent/JP5851415B2/ja not_active Expired - Fee Related
- 2010-12-03 US US13/513,666 patent/US8937201B2/en not_active Expired - Fee Related
- 2010-12-03 PT PT131683906T patent/PT2657217T/pt unknown
- 2010-12-03 KR KR1020127014496A patent/KR101822607B1/ko not_active Expired - Fee Related
-
2015
- 2015-09-11 JP JP2015179301A patent/JP2015221838A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| TWI624450B (zh) | 2018-05-21 |
| KR20120125234A (ko) | 2012-11-14 |
| WO2011069052A2 (en) | 2011-06-09 |
| JP5851415B2 (ja) | 2016-02-03 |
| JP2013512925A (ja) | 2013-04-18 |
| SG181078A1 (en) | 2012-07-30 |
| CN102906059B (zh) | 2015-09-23 |
| ES2647102T3 (es) | 2017-12-19 |
| EP2657217B1 (en) | 2017-09-06 |
| RU2606130C2 (ru) | 2017-01-10 |
| BR112012013419C8 (pt) | 2019-09-03 |
| CN102906059A (zh) | 2013-01-30 |
| JP2015221838A (ja) | 2015-12-10 |
| EP2657217A2 (en) | 2013-10-30 |
| BR112012013419B8 (pt) | 2019-08-20 |
| RU2012127805A (ru) | 2014-01-10 |
| TW201136882A (en) | 2011-11-01 |
| KR101822607B1 (ko) | 2018-01-26 |
| BR112012013419A2 (pt) | 2017-03-21 |
| EP2657217A3 (en) | 2014-04-02 |
| BR112012013419B1 (pt) | 2018-10-09 |
| PL2657217T3 (pl) | 2018-01-31 |
| US8937201B2 (en) | 2015-01-20 |
| TW201700445A (zh) | 2017-01-01 |
| US20130150629A1 (en) | 2013-06-13 |
| TWI570102B (zh) | 2017-02-11 |
| WO2011069052A3 (en) | 2011-11-17 |
| EP2521706A2 (en) | 2012-11-14 |
| PT2657217T (pt) | 2017-11-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SA110310888B1 (ar) | عملية لإنتاج ثلاثي-بيوتيل فينول من تيار c4 مكرر مُصفّى | |
| KR102297240B1 (ko) | 수소 첨가 석유 수지의 제조 방법 | |
| JPS58109428A (ja) | 線状オレフイン生成物の製造法 | |
| KR102365282B1 (ko) | 혼합된 데실 메르캅탄 조성물 및 이의 제조 방법 | |
| KR20000058191A (ko) | 부텐 올리고머로부터 비닐 에스테르를 제조하는 방법 | |
| JPS58113138A (ja) | 線状オレフイン生成物の製造法 | |
| US10894801B2 (en) | Process for producing alkylalkoxysilanes | |
| US5162597A (en) | Olefin disproportionation and application thereof | |
| US2851501A (en) | Production of poly alkyl indanes from styrene compounds | |
| EP1421053B1 (en) | Process for the production of acetic acid c4-esters | |
| CN111393253B (zh) | 一种含有反式取代环己基的化合物的合成方法 | |
| JP2664497B2 (ja) | α―オレフィンの製法 | |
| US4229597A (en) | Process for the preparation of resorcin | |
| US11124470B2 (en) | Systems and methods of producing methyl tertiary butyl ether and propylene | |
| CA2830477C (en) | Process for the manufacture of .alpha.,.alpha.-branched carboxylic acid vinyl esters | |
| JPH07116086B2 (ja) | ｔｅｒｔ．ブチルフエノ−ル類の製造方法 | |
| JPH0583088B2 (enExample) | ||
| CN104936937B (zh) | 制备c4含氧物的方法 | |
| CN119744253A (zh) | 烯烃异构化方法 | |
| JP3757969B2 (ja) | 第３級アルコールの製造法 | |
| JPH06136081A (ja) | 耐熱性に優れた芳香族系石油樹脂の製造法 | |
| JPS61251633A (ja) | 高純度Ｐ−ｔｅｒｔ−ブチルフエノ−ルの製造法 |