NL1004636C2 - Werkwijze voor het voortbrengen van propeenoxyde. - Google Patents

Werkwijze voor het voortbrengen van propeenoxyde. Download PDF

Info

Publication number: NL1004636C2
Authority: NL; Netherlands
Prior art keywords: solution; reaction; ebhp; concentration; ethylbenzene
Prior art date: 1995-12-06

Application number

NL1004636A

Other languages

English (en)

Dutch (nl)

Other versions

NL1004636A1 (nl

Inventor

Noriaki Oku

Masaru Ishino

Junpei Tsuji

Kenshi Uchida

Mitsuhisa Tamura

Original Assignee

Sumitomo Chemical Co

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.)

1995-12-06

Filing date

1996-11-28

Publication date

1998-03-20

1995-12-06 Priority claimed from JP7317841A external-priority patent/JP3024531B2/ja

1996-06-07 Priority claimed from JP14549396A external-priority patent/JP3829361B2/ja

1996-11-28 Application filed by Sumitomo Chemical Co filed Critical Sumitomo Chemical Co

1997-06-10 Publication of NL1004636A1 publication Critical patent/NL1004636A1/xx

1998-03-20 Application granted granted Critical

1998-03-20 Publication of NL1004636C2 publication Critical patent/NL1004636C2/nl

Links

238000000034 method Methods 0.000 title claims description 18
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title claims description 11
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 52
239000003513 alkali Substances 0.000 claims description 41
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 34
239000002994 raw material Substances 0.000 claims description 31
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 27
239000004310 lactic acid Substances 0.000 claims description 26
235000014655 lactic acid Nutrition 0.000 claims description 26
238000005406 washing Methods 0.000 claims description 26
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 19
GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
238000004821 distillation Methods 0.000 claims description 7
239000011949 solid catalyst Substances 0.000 claims description 7
229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
238000006701 autoxidation reaction Methods 0.000 claims description 4
239000007791 liquid phase Substances 0.000 claims description 4
BBPKLXNDBPZOAH-UHFFFAOYSA-N hydrogen peroxide;toluene Chemical compound OO.CC1=CC=CC=C1 BBPKLXNDBPZOAH-UHFFFAOYSA-N 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 47
239000003054 catalyst Substances 0.000 description 23
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000006735 epoxidation reaction Methods 0.000 description 12
239000007787 solid Substances 0.000 description 12
239000010936 titanium Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
150000007524 organic acids Chemical class 0.000 description 10
235000005985 organic acids Nutrition 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
-1 olefin compound Chemical class 0.000 description 9
239000002904 solvent Substances 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
230000000052 comparative effect Effects 0.000 description 7
239000000203 mixture Substances 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
239000012071 phase Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
230000007423 decrease Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000001993 wax Substances 0.000 description 5
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
239000002574 poison Substances 0.000 description 4
231100000614 poison Toxicity 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
230000009849 deactivation Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000002411 adverse Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
238000006757 chemical reactions by type Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
230000004907 flux Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000003756 stirring Methods 0.000 description 2
JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
239000002699 waste material Substances 0.000 description 2
239000002351 wastewater Substances 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
238000001354 calcination Methods 0.000 description 1
238000000975 co-precipitation Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000003317 industrial substance Substances 0.000 description 1
229910052909 inorganic silicate Inorganic materials 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000003980 solgel method Methods 0.000 description 1
230000001629 suppression Effects 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Classifications

- 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
- 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

Landscapes

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

NL1004636A 1995-12-06 1996-11-28 Werkwijze voor het voortbrengen van propeenoxyde. NL1004636C2 (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP31784195		1995-12-06
JP7317841A JP3024531B2 (ja)	1995-12-06	1995-12-06	プロピレンオキサイドの製造方法
JP14549396A JP3829361B2 (ja)	1996-06-07	1996-06-07	プロピレンオキサイドの製造方法
JP14549396		1996-06-07

Publications (2)

Publication Number	Publication Date
NL1004636A1 NL1004636A1 (nl)	1997-06-10
NL1004636C2 true NL1004636C2 (nl)	1998-03-20

Family

ID=26476586

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1004636A NL1004636C2 (nl)	1995-12-06	1996-11-28	Werkwijze voor het voortbrengen van propeenoxyde.

Country Status (6)

Country	Link
US (1)	US5723637A (es)
KR (1)	KR100489466B1 (es)
ES (1)	ES2128246B1 (es)
FR (1)	FR2742150B1 (es)
NL (1)	NL1004636C2 (es)
SG (1)	SG45518A1 (es)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6187934B1 (en) *	1997-03-26	2001-02-13	Sumitomo Chemical Company Limited	Titanium-containing solid catalyst
US5883268A (en) *	1997-10-23	1999-03-16	Arco Chemical Technology, L.P.	Process stream purification
SG73663A1 (en) *	1998-08-04	2000-06-20	Sumitomo Chemical Co	A process for producing propylene oxide
SG82626A1 (en)	1998-08-04	2001-08-21	Sumitomo Chemical Co	Titanium-containing silicon oxide catalyst
ES2156506B1 (es) *	1998-10-14	2002-03-01	Sumitomo Chemical Co	Metodo para la produccion de oxido de propileno.
JP2001031662A (ja) *	1999-07-14	2001-02-06	Sumitomo Chem Co Ltd	プロピレンオキサイドの製造方法
JP2001270876A (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
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
JP2001270877A (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
US6455712B1 (en) *	2000-12-13	2002-09-24	Shell Oil Company	Preparation of oxirane compounds
JP3939655B2 (ja)	2000-12-27	2007-07-04	シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー	汚染物質の含有量を低減させた有機ヒドロペルオキシドの調製方法
JP2002322164A (ja) *	2001-04-27	2002-11-08	Sumitomo Chem Co Ltd	プロピレンオキサイドの製造方法
CN1297547C (zh) *	2001-08-22	2007-01-31	住友化学工业株式会社	环氧丙烷制造方法
AU2002366573A1 (en) *	2001-12-05	2003-06-23	Dow Global Technologies Inc.	Process of preparing an olefin oxide from olefin and organic hydroperoxide
JP4643110B2 (ja) *	2002-01-08	2011-03-02	住友化学株式会社	プロピレンオキサイドの製造方法
US6512129B1 (en) *	2002-01-23	2003-01-28	Arco Chemical Technology, L.P.	Epoxidation process
EP1666443B1 (en) *	2003-09-25	2011-04-20	Sumitomo Chemical Company, Limited	Process for producing cumene and process for propylene oxide production including the production process
JP4385700B2 (ja) *	2003-09-26	2009-12-16	住友化学株式会社	プロピレンオキサイドの製造方法
US20090209771A1 (en) *	2005-01-14	2009-08-20	Sumitomo Chemical Company, Limited	Method for producing propylene oxide
JP4910503B2 (ja) *	2005-08-25	2012-04-04	住友化学株式会社	プロピレンオキサイドの製造方法
EP2108639A1 (en)	2008-04-07	2009-10-14	Shell Internationale Researchmaatschappij B.V.	Process for the preparation of monopropylene glycol
CN109851575B (zh) *	2017-11-30	2021-03-26	中国石油化工股份有限公司	环氧烷烃生产中有机酸的脱除方法
CN112010823B (zh) *	2019-05-29	2022-08-12	中国石油化工股份有限公司	环氧烷烃分离及苄醇纯化方法
EP3878554A4 (en) *	2020-01-14	2022-07-13	Wanhua Chemical Group Co., Ltd.	PROCESS FOR THE PREPARATION OF A CATALYST FOR THE EPOXYDATION OF PROPYLENE AND ITS USE
WO2021263130A1 (en)	2020-06-26	2021-12-30	Lyondell Chemical Technology, L.P.	Use of monopropylene glycol from purge streams in epoxidation catalyst preparation

Citations (2)

* 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
NL7004582A (es) *	1969-04-02	1970-10-06

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Publication number	Priority date	Publication date	Assignee	Title
US2829173A (en) *	1952-11-08	1958-04-01	California Research Corp	Oxidation process
US3923843A (en) *	1972-03-13	1975-12-02	Shell Oil Co	Epoxidation process with improved heterogeneous catalyst
US3899445A (en) *	1972-06-01	1975-08-12	Toray Industries	Catalyst for oxidation of ethylene to ethylene oxide
JPS5030049A (es) *	1973-07-19	1975-03-26
JPS5440526A (en) *	1977-09-07	1979-03-30	Toshiba Corp	Integrated drawing processor
JPS5440525A (en) *	1977-09-07	1979-03-30	Hitachi Ltd	Terminal device
DE2926543A1 (de) *	1979-06-30	1981-01-22	Guenter Kollross	Verfahren und vorrichtung zur bildung eines endverschlusses an einem raupenfoermig gerafften stueck schlauchmaterial, insbesondere kunstdarm fuer die wurstherstellung
US4296001A (en) *	1980-02-06	1981-10-20	Phillips Petroleum Company	Titanium impregnated silica-chromium catalysts
KR870004013A (ko) *	1985-10-24	1987-05-06	채영복	에틸렌 옥사이드 및 프로필렌 옥사이드의 제조방법 및 그의 장치
US5262550A (en) *	1992-04-30	1993-11-16	Arco Chemical Technology, L.P.	Epoxidation process using titanium-rich silicalite catalysts
FR2704159B1 (fr) *	1993-04-22	1995-06-09	Atochem Elf Sa	Catalyseur solide à base de silice particulaire, comportant du titane, Procédé d'obtention, et utilisation dans l'époxydation d'oléfines.
JP3552306B2 (ja) *	1994-11-04	2004-08-11	住友化学工業株式会社	プロピレンオキシドとスチレンモノマーの製造法

1996
- 1996-11-22 US US08/754,125 patent/US5723637A/en not_active Expired - Lifetime
- 1996-11-28 NL NL1004636A patent/NL1004636C2/nl not_active IP Right Cessation
- 1996-11-29 SG SG1996011463A patent/SG45518A1/en unknown
- 1996-12-02 FR FR9614735A patent/FR2742150B1/fr not_active Expired - Fee Related
- 1996-12-02 KR KR1019960061035A patent/KR100489466B1/ko not_active Expired - Fee Related
- 1996-12-02 ES ES009602550A patent/ES2128246B1/es not_active Expired - Fee Related

Patent Citations (2)

* 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
NL7004582A (es) *	1969-04-02	1970-10-06

Also Published As

Publication number	Publication date
KR980002039A (ko)	1998-03-30
NL1004636A1 (nl)	1997-06-10
ES2128246B1 (es)	2000-01-16
FR2742150B1 (fr)	1998-12-24
FR2742150A1 (fr)	1997-06-13
US5723637A (en)	1998-03-03
SG45518A1 (en)	1998-01-16
ES2128246A1 (es)	1999-05-01
KR100489466B1 (ko)	2005-12-29

Legal Events

Date	Code	Title	Description
1997-08-01	AD1A	A request for search or an international type search has been filed
1998-05-06	PD2B	A search report has been drawn up
2014-06-18	V1	Lapsed because of non-payment of the annual fee	Effective date: 20140601

Publication	Publication Date	Title
NL1004636C2 (nl)	1998-03-20	Werkwijze voor het voortbrengen van propeenoxyde.
Thiele et al.	1997	Propylene epoxidation with hydrogen peroxide and titanium silicalite catalyst: Activity, deactivation and regeneration of the catalyst
EP0577709B1 (en)	1997-01-08	Process for preparing an alkanone and/or alkanol
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