ZA200601210B - Process for the preparation of alkylene oxide - Google Patents
Process for the preparation of alkylene oxide Download PDFInfo
- Publication number
- ZA200601210B ZA200601210B ZA200601210A ZA200601210A ZA200601210B ZA 200601210 B ZA200601210 B ZA 200601210B ZA 200601210 A ZA200601210 A ZA 200601210A ZA 200601210 A ZA200601210 A ZA 200601210A ZA 200601210 B ZA200601210 B ZA 200601210B
- Authority
- ZA
- South Africa
- Prior art keywords
- reaction mixture
- alcohol
- hydroperoxide
- process according
- organic hydroperoxide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 230000008569 process Effects 0.000 title claims abstract description 45
- 125000002947 alkylene group Chemical group 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 40
- 239000011541 reaction mixture Substances 0.000 claims abstract description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 27
- 150000002432 hydroperoxides Chemical class 0.000 claims abstract description 25
- 150000001336 alkenes Chemical class 0.000 claims abstract description 18
- 238000004064 recycling Methods 0.000 claims abstract description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 29
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical group OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 4
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- -1 l-butene Chemical compound 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RNDNSYIPLPAXAZ-UHFFFAOYSA-N 2-Phenyl-1-propanol Chemical compound OCC(C)C1=CC=CC=C1 RNDNSYIPLPAXAZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03255129 | 2003-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200601210B true ZA200601210B (en) | 2007-04-25 |
Family
ID=34178609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200601210A ZA200601210B (en) | 2003-08-19 | 2006-02-10 | Process for the preparation of alkylene oxide |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20050070725A1 (es) |
| EP (1) | EP1656362B1 (es) |
| JP (1) | JP2007533608A (es) |
| KR (1) | KR20060081702A (es) |
| CN (1) | CN1835939A (es) |
| AT (1) | ATE417840T1 (es) |
| AU (1) | AU2004264394B2 (es) |
| BR (1) | BRPI0413615A (es) |
| DE (1) | DE602004018510D1 (es) |
| ES (1) | ES2319993T3 (es) |
| RU (1) | RU2354654C2 (es) |
| WO (1) | WO2005016903A1 (es) |
| ZA (1) | ZA200601210B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008266304A (ja) * | 2007-03-22 | 2008-11-06 | Sumitomo Chemical Co Ltd | プロピレンオキサイドの製造方法 |
| WO2013067339A1 (en) * | 2011-11-04 | 2013-05-10 | Dow Global Technologies Llc | Process and system for producing an oxirane |
| FR3001968B1 (fr) * | 2013-02-12 | 2015-02-27 | IFP Energies Nouvelles | Procede de production d'oxyde d'ethylene a partir d'un flux d'ethanol thermo-mecaniquement integre |
| US9221775B2 (en) | 2014-01-03 | 2015-12-29 | Shell Oil Company | Alkylene oxide production |
| CN105294605A (zh) * | 2014-07-24 | 2016-02-03 | 中国石油化工股份有限公司 | 过氧化氢乙苯与丙烯制环氧丙烷的循环方法 |
| CN105315235A (zh) * | 2014-07-24 | 2016-02-10 | 中国石油化工股份有限公司 | 过氧化氢乙苯与丙烯环氧化的方法 |
| CN108349918A (zh) | 2015-11-09 | 2018-07-31 | 国际壳牌研究有限公司 | 催化剂制备 |
| CN109942470B (zh) * | 2017-12-21 | 2020-04-10 | 万华化学集团股份有限公司 | 由乙苯液相过氧化制备乙苯氢过氧化物的方法及环氧丙烷的制备方法 |
| RU2731267C1 (ru) * | 2020-01-31 | 2020-09-01 | федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский национальный исследовательский технологический университет" (ФГБОУ ВО "КНИТУ") | Способ получения гидропероксида этилбензола |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3439001A (en) * | 1965-10-01 | 1969-04-15 | Halcon International Inc | Epoxidation using ethylbenzene hydroperoxide with alkali or adsorbent treatment of recycle ethylbenzene |
| US3350422A (en) * | 1966-02-01 | 1967-10-31 | Halcon International Inc | Catalytic epoxidation of an olefinically unsaturated compound using an organic hydroperoxide as an epoxidizing agent |
| US4367342A (en) * | 1969-04-02 | 1983-01-04 | Shell Oil Company | Olefin epoxidation |
| US3849451A (en) * | 1970-06-30 | 1974-11-19 | Halcon International Inc | Epoxidation process |
| US4021454A (en) * | 1971-08-19 | 1977-05-03 | Shell Oil Company | Olefin epoxidation |
| GB8813484D0 (en) | 1988-06-08 | 1988-07-13 | Shell Int Research | Process for preparation of oxirane compound |
| US5286884A (en) * | 1992-07-24 | 1994-02-15 | Texaco Chemical Company | Thermosyphonic reaction of propylene with tertiary butyl hydroperoxide and reactor |
| US5349072A (en) * | 1993-07-06 | 1994-09-20 | Texaco Chemical Company | Staged epoxidation of propylene with recycle |
| US5410077A (en) * | 1993-11-08 | 1995-04-25 | Texaco Chemical Company | Controlled epoxidation of propylene |
| JP3812851B2 (ja) * | 1996-06-21 | 2006-08-23 | アルコ ケミカル テクノロジー エルピー | １−フェニルエタノール、アセトフェノンまたはそれらの混合物からのフェノールの分離方法 |
| US5916835A (en) * | 1996-12-20 | 1999-06-29 | Arco Chemical Technology, L.P. | Heterogeneous catalyst regeneration |
| US5760253A (en) | 1997-01-29 | 1998-06-02 | Arco Chemical Technology, L.P. | Catalytic converter and method for highly exothermic reactions |
| KR20010070977A (ko) * | 1998-07-20 | 2001-07-28 | 오노 알버어스 | 스티렌 및 프로필렌 옥사이드의 제조방법 |
| ES2156506B1 (es) * | 1998-10-14 | 2002-03-01 | Sumitomo Chemical Co | Metodo para la produccion de oxido de propileno. |
| JP3628650B2 (ja) | 1999-06-29 | 2005-03-16 | フラッシュポイント ホールディングズ ジャパン インコーポレイテッド | ホストコンピュータ上において画像取込み装置からの画像を閲覧するための方法およびシステム |
| US6365761B1 (en) * | 1999-08-18 | 2002-04-02 | Shell Oil Company | Process for preparing alkylene oxide |
| JP2001270872A (ja) * | 2000-03-24 | 2001-10-02 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
| IT1318681B1 (it) * | 2000-08-11 | 2003-08-27 | Enichem Spa | Procedimento integrato per la preparazione di epossidi. |
| US6455712B1 (en) * | 2000-12-13 | 2002-09-24 | Shell Oil Company | Preparation of oxirane compounds |
| BR0212664A (pt) * | 2001-09-21 | 2004-08-24 | Sumitomo Chemical Co | Processo para produção de óxido de propileno |
| US7294726B2 (en) * | 2002-04-03 | 2007-11-13 | Shell Oil Company | Process for preparing alkylene oxide |
-
2004
- 2004-07-26 KR KR1020067003346A patent/KR20060081702A/ko not_active Application Discontinuation
- 2004-07-26 DE DE602004018510T patent/DE602004018510D1/de not_active Expired - Fee Related
- 2004-07-26 ES ES04742009T patent/ES2319993T3/es active Active
- 2004-07-26 RU RU2006108556/04A patent/RU2354654C2/ru not_active IP Right Cessation
- 2004-07-26 BR BRPI0413615-2A patent/BRPI0413615A/pt active Search and Examination
- 2004-07-26 CN CNA2004800235552A patent/CN1835939A/zh active Pending
- 2004-07-26 WO PCT/EP2004/051601 patent/WO2005016903A1/en active Search and Examination
- 2004-07-26 EP EP04742009A patent/EP1656362B1/en not_active Not-in-force
- 2004-07-26 AT AT04742009T patent/ATE417840T1/de not_active IP Right Cessation
- 2004-07-26 JP JP2006523624A patent/JP2007533608A/ja active Pending
- 2004-07-26 AU AU2004264394A patent/AU2004264394B2/en not_active Ceased
- 2004-08-19 US US10/922,031 patent/US20050070725A1/en not_active Abandoned
-
2006
- 2006-02-10 ZA ZA200601210A patent/ZA200601210B/en unknown
-
2010
- 2010-10-13 US US12/903,784 patent/US8017794B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2319993T3 (es) | 2009-05-18 |
| US8017794B2 (en) | 2011-09-13 |
| DE602004018510D1 (de) | 2009-01-29 |
| JP2007533608A (ja) | 2007-11-22 |
| ATE417840T1 (de) | 2009-01-15 |
| WO2005016903A1 (en) | 2005-02-24 |
| AU2004264394A1 (en) | 2005-02-24 |
| CN1835939A (zh) | 2006-09-20 |
| KR20060081702A (ko) | 2006-07-13 |
| RU2354654C2 (ru) | 2009-05-10 |
| RU2006108556A (ru) | 2006-07-27 |
| EP1656362A1 (en) | 2006-05-17 |
| AU2004264394B2 (en) | 2008-01-03 |
| EP1656362B1 (en) | 2008-12-17 |
| US20050070725A1 (en) | 2005-03-31 |
| BRPI0413615A (pt) | 2006-10-17 |
| US20110028745A1 (en) | 2011-02-03 |
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