DD297802A5 - Verfahren zur darstellung von phenol - Google Patents
Verfahren zur darstellung von phenol Download PDFInfo
- Publication number
- DD297802A5 DD297802A5 DD89333069A DD33306989A DD297802A5 DD 297802 A5 DD297802 A5 DD 297802A5 DD 89333069 A DD89333069 A DD 89333069A DD 33306989 A DD33306989 A DD 33306989A DD 297802 A5 DD297802 A5 DD 297802A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- propylene
- acetone
- phenol
- reaction
- cumene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 230000008569 process Effects 0.000 title claims abstract description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 113
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 91
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 71
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 70
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 63
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims abstract description 56
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 239000003054 catalyst Substances 0.000 claims description 31
- 230000003647 oxidation Effects 0.000 claims description 17
- 238000007254 oxidation reaction Methods 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000003776 cleavage reaction Methods 0.000 claims description 15
- 230000007017 scission Effects 0.000 claims description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000006835 compression Effects 0.000 claims 1
- 238000007906 compression Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 10
- 230000001590 oxidative effect Effects 0.000 abstract 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000007789 gas Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 239000006227 byproduct Substances 0.000 description 16
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000029936 alkylation Effects 0.000 description 10
- 238000005804 alkylation reaction Methods 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000003570 air Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
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- 239000012141 concentrate Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 4
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- 239000012429 reaction media Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 229910001385 heavy metal Inorganic materials 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
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- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 2
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 241000196324 Embryophyta Species 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 2
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 2
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- 239000011973 solid acid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/10—Cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/06—Propene
-
- 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
- C07C39/04—Phenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| JP24665888 | 1988-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD297802A5 true DD297802A5 (de) | 1992-01-23 |
Family
ID=17151694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD89333069A DD297802A5 (de) | 1988-09-30 | 1989-09-28 | Verfahren zur darstellung von phenol |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5017729A (fr) |
| EP (1) | EP0361755B1 (fr) |
| KR (1) | KR0132775B1 (fr) |
| CN (1) | CN1026782C (fr) |
| AT (1) | ATE106376T1 (fr) |
| CA (1) | CA1320500C (fr) |
| CZ (1) | CZ554989A3 (fr) |
| DD (1) | DD297802A5 (fr) |
| DE (1) | DE68915672T2 (fr) |
| ES (1) | ES2057138T3 (fr) |
| MY (1) | MY105036A (fr) |
| PL (1) | PL165409B1 (fr) |
| RO (1) | RO103772B1 (fr) |
| RU (1) | RU2014318C1 (fr) |
| SG (1) | SG20395G (fr) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2003925C (fr) * | 1988-11-28 | 1999-11-23 | Shintaro Araki | Production de cumene par alkylation d'un compose aromatique et preparation du phenol a l'aide du cumene |
| FR2656300B1 (fr) * | 1989-12-21 | 1993-06-11 | Inst Francais Du Petrole | Procede de production de phenol. |
| US5245090A (en) * | 1992-09-11 | 1993-09-14 | Aristech Chemical Corporation | Two-stage cleavage of cumene hydroperoxide |
| US5254751A (en) | 1992-09-14 | 1993-10-19 | General Electric Company | Method for the decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone |
| US5371305A (en) * | 1992-12-31 | 1994-12-06 | Hercules Incorporated | Process for producing phenol from cumene |
| US5637778A (en) * | 1994-08-08 | 1997-06-10 | Texaco Chemical Inc. | Isopropyl alcohol and diispropyl ether production from crude by-product acetone in one step |
| US5457244A (en) * | 1994-10-04 | 1995-10-10 | General Electric Company | Phenol tar waste reduction process |
| TW318174B (fr) * | 1994-11-04 | 1997-10-21 | Gen Electric | |
| US5510543A (en) * | 1994-12-09 | 1996-04-23 | General Electric Company | Removal and neutralization of acid catalyst from products of cumene hydroperoxide cleavage |
| IN185136B (fr) * | 1995-09-20 | 2000-11-25 | Gen Electric | |
| US5672774A (en) * | 1995-10-24 | 1997-09-30 | General Electric Company | Phenol tar processing method |
| PL181496B1 (pl) * | 1996-03-20 | 2001-07-31 | Politechnika Slaska Im Wincent | Sposób wytwarzania ß-naftolu PL |
| US5962751A (en) * | 1996-04-26 | 1999-10-05 | General Electric Company | Phenol tar desalting method |
| RU2125038C1 (ru) * | 1996-09-24 | 1999-01-20 | Закошанский Владимир Михайлович | Безотходный экономичный способ получения фенола и ацетона |
| CN1067367C (zh) * | 1997-07-28 | 2001-06-20 | 中国石油化工总公司 | 催化分解芳基α－氢过氧化物制备酚和酮或醛的方法 |
| CN1067368C (zh) * | 1997-07-28 | 2001-06-20 | 中国石油化工总公司 | 催化分解芳基α－氢过氧化物制备酚和酮或醛的方法 |
| DE10008924A1 (de) * | 2000-02-25 | 2001-09-06 | Phenolchemie Gmbh & Co Kg | Verfahren zur Herstellung von Phenol |
| US6376708B1 (en) * | 2000-04-11 | 2002-04-23 | Monsanto Technology Llc | Process and catalyst for dehydrogenating primary alcohols to make carboxylic acid salts |
| KR100852565B1 (ko) * | 2000-09-25 | 2008-08-18 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 페놀 생산에서 분해 유출물의 수소화 방법 |
| US6455712B1 (en) * | 2000-12-13 | 2002-09-24 | Shell Oil Company | Preparation of oxirane compounds |
| AU2002362929B2 (en) | 2001-10-18 | 2007-08-09 | Monsanto Technology Llc | Process and catalyst for dehydrogenating primary alcohols to make carboxylic acid salts |
| TWI266762B (en) * | 2001-11-16 | 2006-11-21 | Shell Int Research | Process for the preparation of isopropanol |
| RU2238141C1 (ru) * | 2003-03-31 | 2004-10-20 | Белоусов Виктор Васильевич | Способ проведения жидкофазных гетерогенных экзотермических реакций |
| EP1940760B1 (fr) * | 2005-10-07 | 2016-08-24 | Badger Licensing LLC | Accroissement du rendement de production d'une installation de production de bisphénol a |
| US20100063329A1 (en) * | 2006-05-16 | 2010-03-11 | John Charles Saukaitis | Method for decomposing di(phenylalkyl)peroxides to produce hydroxybenzenes and phenylalkenes using solid catalysts |
| US8581016B2 (en) * | 2006-11-21 | 2013-11-12 | Mitsui Chemicals, Inc. | Process for producing alkylated aromatic compound and process for producing phenol |
| EP2045232A1 (fr) * | 2007-10-04 | 2009-04-08 | INEOS Phenol GmbH & Co. KG | Procédé de production d'iso-propanol par hydrogénation de phase liquide |
| US7799958B2 (en) | 2007-10-04 | 2010-09-21 | Barclays Bank Plc | Process for the production of iso-propanol by liquid phase hydrogenation |
| US8404914B2 (en) * | 2008-06-10 | 2013-03-26 | Mitsui Chemicals, Inc. | Process for producing alkylated aromatic compounds and process for producing phenol |
| WO2009150973A1 (fr) * | 2008-06-10 | 2009-12-17 | 三井化学株式会社 | Procédé de fabrication d’un composé aromatique alkylé et procédé de fabrication de phénol |
| IT1392325B1 (it) | 2008-09-11 | 2012-02-28 | Polimeri Europa Spa | Processo per l'alchilazione di benzene con isopropanolo o miscele di isopropanolo e propilene |
| WO2010042315A2 (fr) * | 2008-10-06 | 2010-04-15 | Badger Licensing, Llc | Procédé de production de cumène |
| TWI458695B (zh) * | 2008-10-06 | 2014-11-01 | Badger Licensing Llc | 異丙苯的製造方法 |
| TWI436969B (zh) * | 2008-10-23 | 2014-05-11 | Mitsui Chemicals Inc | 烷基化芳香族化合物之製造方法，異丙苯之製造方法及酚之製造方法 |
| RU2469998C1 (ru) * | 2008-12-01 | 2012-12-20 | Митсуи Кемикалс, Инк. | Способ получения олефинов |
| IT1392929B1 (it) | 2009-02-16 | 2012-04-02 | Polimeri Europa Spa | Processo integrato per la preparazione di etilbenzene e cumene |
| BRPI1009187A2 (pt) * | 2009-03-16 | 2016-03-01 | Mitsui Chemicals Inc | processo de produção de olefina |
| WO2010106967A1 (fr) | 2009-03-19 | 2010-09-23 | 三井化学株式会社 | Procédé de production de composé aromatique alkylé et procédé de production de phénol |
| ITMI20111143A1 (it) | 2011-06-23 | 2012-12-24 | Polimeri Europa Spa | Procedimento per l'alchilazione di idrocarburi aromatici con alcoli c1-c8 |
| US8766009B2 (en) | 2011-11-21 | 2014-07-01 | Basf Se | Process for preparing ethylamines and monoisopropylamine (MIPA) |
| WO2013075974A1 (fr) | 2011-11-21 | 2013-05-30 | Basf Se | Procédé de préparation d'éthylamines et de mono-isopropylamine (mipa) |
| ES2609779T3 (es) | 2012-01-20 | 2017-04-24 | Mitsui Chemicals, Inc. | Método para producir olefina |
| US9593056B2 (en) * | 2012-12-11 | 2017-03-14 | Exxonmobil Chemical Patents Inc. | Process for producing cumene with alkylation effluent recycle |
| JP6076477B2 (ja) | 2013-06-07 | 2017-02-08 | 三井化学株式会社 | オレフィンの製造方法、およびこれに用いられる脱水触媒 |
| ITMI20131704A1 (it) | 2013-10-15 | 2015-04-16 | Versalis Spa | Composizione catalitica e processo che la utilizza per l'alchilazione di idrocarburi aromatici con alcoli, o miscele di alcoli e olefine |
| IT201700074911A1 (it) | 2017-07-04 | 2019-01-04 | Versalis Spa | Procedimento per la produzione di olefine da alcoli |
| IT202200025110A1 (it) | 2022-12-06 | 2024-06-06 | Versalis Spa | Procedimento per la preparazione di isopropanolo in alte rese e con un elevato grado di purezza. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3436429A (en) * | 1966-11-23 | 1969-04-01 | Skelly Oil Co | Hydrogenation process |
| EP0018159B1 (fr) * | 1979-04-20 | 1983-05-11 | Imperial Chemical Industries Plc | Procédé de préparation de phénol, d'acétone et d'alpha méthylstyrène |
| US4260845A (en) * | 1980-01-21 | 1981-04-07 | Phillips Petroleum Company | Alcohol dehydration employing a zinc aluminate catalyst |
| US4431849A (en) * | 1981-10-21 | 1984-02-14 | The Goodyear Tire & Rubber Company | Process for preparing a methyl phenol |
| JPS6212729A (ja) * | 1985-07-11 | 1987-01-21 | Mitsui Petrochem Ind Ltd | イソプロピルアルコ−ルの製造法 |
| JPH0692334B2 (ja) * | 1985-09-30 | 1994-11-16 | 石川島播磨重工業株式会社 | イソプロパノ−ルの製造装置 |
| US4711869A (en) * | 1985-11-08 | 1987-12-08 | Aristech Chemical Corporation | Silica-titania hydrocarbon conversion catalyst |
| EP0484319B1 (fr) * | 1987-09-12 | 1995-11-08 | Mitsui Petrochemical Industries, Ltd. | Procédé de production d'isopropylnaphtols |
| US4876397A (en) * | 1988-10-24 | 1989-10-24 | Texaco Chemical Company | Method for production of phenol/acetone from cumene hydroperoxide |
-
1989
- 1989-09-05 US US07/402,528 patent/US5017729A/en not_active Expired - Lifetime
- 1989-09-09 MY MYPI89001231A patent/MY105036A/en unknown
- 1989-09-18 CN CN89107420A patent/CN1026782C/zh not_active Expired - Lifetime
- 1989-09-19 EP EP89309487A patent/EP0361755B1/fr not_active Expired - Lifetime
- 1989-09-19 DE DE68915672T patent/DE68915672T2/de not_active Expired - Lifetime
- 1989-09-19 AT AT89309487T patent/ATE106376T1/de active
- 1989-09-19 ES ES89309487T patent/ES2057138T3/es not_active Expired - Lifetime
- 1989-09-26 CA CA000613318A patent/CA1320500C/fr not_active Expired - Lifetime
- 1989-09-27 PL PL89281599A patent/PL165409B1/pl unknown
- 1989-09-28 DD DD89333069A patent/DD297802A5/de not_active IP Right Cessation
- 1989-09-28 RO RO141799A patent/RO103772B1/ro unknown
- 1989-09-29 CZ CS895549A patent/CZ554989A3/cs unknown
- 1989-09-29 RU SU894742034A patent/RU2014318C1/ru active
- 1989-09-30 KR KR1019890014095A patent/KR0132775B1/ko not_active Expired - Lifetime
-
1995
- 1995-02-08 SG SG1995090203A patent/SG20395G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0361755A2 (fr) | 1990-04-04 |
| CA1320500C (fr) | 1993-07-20 |
| EP0361755A3 (en) | 1990-12-05 |
| KR0132775B1 (ko) | 1998-04-13 |
| CN1026782C (zh) | 1994-11-30 |
| MY105036A (en) | 1994-07-30 |
| CZ554989A3 (en) | 1995-08-16 |
| CN1041581A (zh) | 1990-04-25 |
| RU2014318C1 (ru) | 1994-06-15 |
| ES2057138T3 (es) | 1994-10-16 |
| US5017729A (en) | 1991-05-21 |
| EP0361755B1 (fr) | 1994-06-01 |
| DE68915672D1 (de) | 1994-07-07 |
| ATE106376T1 (de) | 1994-06-15 |
| KR900004663A (ko) | 1990-04-12 |
| SG20395G (en) | 1995-08-18 |
| PL165409B1 (en) | 1994-12-30 |
| RO103772B1 (en) | 1993-10-02 |
| DE68915672T2 (de) | 1994-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |