ZA200601210B - Process for the preparation of alkylene oxide - Google Patents

Process for the preparation of alkylene oxide Download PDF

Info

Publication number: ZA200601210B
Authority: ZA; South Africa
Prior art keywords: reaction mixture; alcohol; hydroperoxide; process according; organic hydroperoxide
Prior art date: 2003-08-19

Application number

ZA200601210A

Other languages

English (en)

Inventor

Ploemen Ingmar Hubertus Josephina

Schouten Eduardus Petrus Simon

Van Der Veen Alexander Jan

Original Assignee

Shell Int Research

Priority date (The priority date 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 date listed.)

2003-08-19

Filing date

2006-02-10

Publication date

2007-04-25

2006-02-10 Application filed by Shell Int Research filed Critical Shell Int Research

2007-04-25 Publication of ZA200601210B publication Critical patent/ZA200601210B/en

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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ZA200601210A 2003-08-19 2006-02-10 Process for the preparation of alkylene oxide ZA200601210B (en)

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 (de)
EP (1)	EP1656362B1 (de)
JP (1)	JP2007533608A (de)
KR (1)	KR20060081702A (de)
CN (1)	CN1835939A (de)
AT (1)	ATE417840T1 (de)
AU (1)	AU2004264394B2 (de)
BR (1)	BRPI0413615A (de)
DE (1)	DE602004018510D1 (de)
ES (1)	ES2319993T3 (de)
RU (1)	RU2354654C2 (de)
WO (1)	WO2005016903A1 (de)
ZA (1)	ZA200601210B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
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
TW201332982A (zh) *	2011-11-04	2013-08-16	Dow Global Technologies Llc	用於製造環氧化物的方法及系統
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
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
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
WO2017080962A1 (en)	2015-11-09	2017-05-18	Shell Internationale Research Maatschappij B.V.	Catalyst preparation
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 (22)

* Cited by examiner, † Cited by third party
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
US5840933A (en) *	1996-10-29	1998-11-24	Arco Chemical Technology, L.P.	Catalytic converter system and progress
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
US6504038B1 (en) *	1998-07-20	2003-01-07	Shell Oil Company	Process for the preparation of styrene and propylene oxide
ES2156506B1 (es) *	1998-10-14	2002-03-01	Sumitomo Chemical Co	Metodo para la produccion de oxido de propileno.
DE60043878D1 (de)	1999-06-29	2010-04-08	Flashpoint Technology Inc	Verfahren und system zum betrachten von bildanzeigen von einer bildanzeigevorrichtung auf einem gastrechner
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
WO2003027087A1 (en) *	2001-09-21	2003-04-03	Sumitomo Chemical Company, Limited	Process for preparation of propylene oxide
US7294726B2 (en) *	2002-04-03	2007-11-13	Shell Oil Company	Process for preparing alkylene oxide

2004
- 2004-07-26 JP JP2006523624A patent/JP2007533608A/ja active Pending
- 2004-07-26 AU AU2004264394A patent/AU2004264394B2/en not_active Ceased
- 2004-07-26 AT AT04742009T patent/ATE417840T1/de not_active IP Right Cessation
- 2004-07-26 RU RU2006108556/04A patent/RU2354654C2/ru not_active IP Right Cessation
- 2004-07-26 KR KR1020067003346A patent/KR20060081702A/ko not_active Withdrawn
- 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 ES ES04742009T patent/ES2319993T3/es not_active Expired - Lifetime
- 2004-07-26 EP EP04742009A patent/EP1656362B1/de not_active Expired - Lifetime
- 2004-07-26 DE DE602004018510T patent/DE602004018510D1/de not_active Expired - Fee Related
- 2004-07-26 WO PCT/EP2004/051601 patent/WO2005016903A1/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
BRPI0413615A (pt)	2006-10-17
EP1656362A1 (de)	2006-05-17
AU2004264394B2 (en)	2008-01-03
KR20060081702A (ko)	2006-07-13
JP2007533608A (ja)	2007-11-22
DE602004018510D1 (de)	2009-01-29
US20110028745A1 (en)	2011-02-03
ES2319993T3 (es)	2009-05-18
WO2005016903A1 (en)	2005-02-24
EP1656362B1 (de)	2008-12-17
ATE417840T1 (de)	2009-01-15
US8017794B2 (en)	2011-09-13
US20050070725A1 (en)	2005-03-31
CN1835939A (zh)	2006-09-20
RU2354654C2 (ru)	2009-05-10
RU2006108556A (ru)	2006-07-27
AU2004264394A1 (en)	2005-02-24

Publication	Publication Date	Title
US8017794B2 (en)	2011-09-13	Process for the preparation of alkylene oxide
AU2002217114B2 (en)	2005-10-06	Process for preparing oxirane compounds
AU2002217114A1 (en)	2002-08-29	Process for preparing oxirane compounds
CN1185221C (zh)	2005-01-19	环氧丙烷制造方法
CA2402739A1 (en)	2002-09-17	Process for producing propylene oxide
US6429323B1 (en)	2002-08-06	Method for continuous production of propylene oxide and other alkene oxides
US6160137A (en)	2000-12-12	Method for producing propylene oxide
CN112174914B (zh)	2023-07-28	一种用于烯烃与氢过氧化物气相环氧化反应的方法
AU757612B2 (en)	2003-02-27	Process for preparing alkylene oxide
CN1401640A (zh)	2003-03-12	一种环己烯催化环氧化制取环氧环己烷的方法
EP1681288A1 (de)	2006-07-19	Verfahren zur herstellung von propylenoxid
US20040127729A1 (en)	2004-07-01	Process for producing propylene oxide
EP1068011B1 (de)	2004-08-18	Verfahren zur epoxidierung von propen
US7294726B2 (en)	2007-11-13	Process for preparing alkylene oxide
AU2002302597B2 (en)	2007-12-20	Process for preparing alkylene oxide (epoxid, oxirane)
AU2002302597A1 (en)	2003-05-01	Process for preparing alkylene oxide (epoxid, oxirane)
JP2001097902A (ja)	2001-04-10	フェノールの製造方法
JPH0435225B2 (de)	1992-06-10
TW200412343A (en)	2004-07-16	Process for production of propylene oxide
GB2129800A (en)	1984-05-23	Process for hydroxylating olefins using an osmium oxide catalyst and sodium hydroxide co-catalyst