DE69920420T2 - Verfahren zur herstellung eines oxirans - Google Patents
Verfahren zur herstellung eines oxirans Download PDFInfo
- Publication number
- DE69920420T2 DE69920420T2 DE69920420T DE69920420T DE69920420T2 DE 69920420 T2 DE69920420 T2 DE 69920420T2 DE 69920420 T DE69920420 T DE 69920420T DE 69920420 T DE69920420 T DE 69920420T DE 69920420 T2 DE69920420 T2 DE 69920420T2
- Authority
- DE
- Germany
- Prior art keywords
- peroxide compound
- reaction
- solvent
- peroxide
- propylene
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 28
- -1 peroxide compound Chemical class 0.000 claims description 25
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000012429 reaction media Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 239000010457 zeolite Substances 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 229910021536 Zeolite Inorganic materials 0.000 claims description 11
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002585 base Substances 0.000 description 11
- 238000006735 epoxidation reaction Methods 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
-
- 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)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9800231A BE1011851A3 (fr) | 1998-03-24 | 1998-03-24 | Procede de fabrication d'un oxiranne. |
| BE9800231 | 1998-03-24 | ||
| PCT/EP1999/001955 WO1999048882A1 (fr) | 1998-03-24 | 1999-03-20 | Procede de fabrication d'un oxiranne |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69920420D1 DE69920420D1 (de) | 2004-10-28 |
| DE69920420T2 true DE69920420T2 (de) | 2005-11-17 |
Family
ID=3891170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69920420T Expired - Lifetime DE69920420T2 (de) | 1998-03-24 | 1999-03-20 | Verfahren zur herstellung eines oxirans |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6429322B1 (enExample) |
| EP (1) | EP1066274B1 (enExample) |
| JP (1) | JP2002507607A (enExample) |
| KR (1) | KR100572805B1 (enExample) |
| CN (1) | CN1330642C (enExample) |
| AR (1) | AR018802A1 (enExample) |
| AT (1) | ATE277028T1 (enExample) |
| AU (1) | AU3035999A (enExample) |
| BE (1) | BE1011851A3 (enExample) |
| BR (1) | BR9909047A (enExample) |
| CA (1) | CA2323005C (enExample) |
| DE (1) | DE69920420T2 (enExample) |
| ES (1) | ES2229689T3 (enExample) |
| HU (1) | HUP0102062A2 (enExample) |
| ID (1) | ID27494A (enExample) |
| NO (1) | NO20004739L (enExample) |
| PL (1) | PL197387B1 (enExample) |
| SA (1) | SA99191303B1 (enExample) |
| SK (1) | SK14232000A3 (enExample) |
| TW (1) | TW539673B (enExample) |
| WO (1) | WO1999048882A1 (enExample) |
| ZA (1) | ZA200004995B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1313572B1 (it) | 1999-07-27 | 2002-09-09 | Enichem Spa | Procedimento per la preparazione di epossidi. |
| DE19944839A1 (de) * | 1999-09-18 | 2001-03-22 | Degussa | Verfahren zur Herstellung von Epoxiden aus Olefinen |
| FR2810982B1 (fr) | 2000-06-28 | 2002-09-27 | Solvay | Procede de fabrication d'oxiranne comprenant la separation de l'oxiranne du milieu reactionnel |
| FR2810980B1 (fr) | 2000-06-28 | 2004-05-21 | Solvay | Procede de fabrication d'oxiranne en presence d'un catalyseur sous forme de particules |
| FR2810983B1 (fr) | 2000-06-28 | 2004-05-21 | Solvay | Procede de fabrication d'oxiranne au moyen d'un compose peroxyde |
| FR2824558B1 (fr) | 2001-05-14 | 2005-05-06 | Solvay | Procede de fabrication d'un oxiranne |
| US7722847B2 (en) * | 2002-09-30 | 2010-05-25 | Evonik Degussa Gmbh | Aqueous hydrogen peroxide solutions and method of making same |
| US6838572B2 (en) * | 2002-09-30 | 2005-01-04 | Degussa Ag | Process for the epoxidation of olefins |
| EP1403259A1 (en) * | 2002-09-30 | 2004-03-31 | Degussa AG | Process for the epoxidation of olefins |
| FR2846965B1 (fr) * | 2002-11-12 | 2006-10-13 | Procede de fabrication de 1,2-epoxy-3-chloropropane | |
| US7169945B2 (en) * | 2002-11-26 | 2007-01-30 | Degussa Ag | Process for the epoxidation of olefins |
| CA2681510C (en) | 2007-04-05 | 2017-03-07 | Solvay (Societe Anonyme) | Aqueous hydrogen peroxide solution, process for its preparation and use thereof |
| EP2501687B1 (en) | 2009-11-19 | 2014-10-15 | Dow Global Technologies LLC | Epoxidation of an olefin |
| RU2588575C2 (ru) | 2010-12-07 | 2016-07-10 | Басф Се | Способ получения пропиленоксида |
| US8785670B2 (en) | 2010-12-07 | 2014-07-22 | Basf Se | Process for the production of propylene oxide |
| WO2012101175A1 (en) | 2011-01-27 | 2012-08-02 | Solvay Sa | Process for the manufacture of 1,2-epoxy-3-chloropropane |
| EP2668172A1 (en) | 2011-01-27 | 2013-12-04 | Solvay SA | Process for the manufacture of 1,2-epoxy-3-chloropropane |
| CN103172597B (zh) * | 2013-04-03 | 2017-12-22 | 北京石油化工学院 | 钛硅分子筛催化合成环氧脂肪酸甲酯的方法 |
| CN107325072A (zh) * | 2017-07-05 | 2017-11-07 | 中国石油化工股份有限公司 | 一种合成环碳酸辛烯酯的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3780476T2 (de) * | 1986-01-28 | 1992-12-17 | Enichem Sintesi | Verfahren zur epoxydation von olefinischen verbindungen. |
| US5646314A (en) * | 1994-11-16 | 1997-07-08 | Arco Chemical Technology, L.P. | Process for titanium silicalite-catalyzed epoxidation |
| DE19528219A1 (de) * | 1995-08-01 | 1997-02-06 | Degussa | Verfahren zur Herstellung von Epoxiden aus Olefinen |
| IT1283232B1 (it) * | 1996-03-12 | 1998-04-16 | Enichem Spa | Procedimento per la sintesi di 2-buten-1, 4-diesteri |
-
1998
- 1998-03-24 BE BE9800231A patent/BE1011851A3/fr not_active IP Right Cessation
-
1999
- 1999-03-19 TW TW088104345A patent/TW539673B/zh not_active IP Right Cessation
- 1999-03-20 PL PL343067A patent/PL197387B1/pl unknown
- 1999-03-20 JP JP2000537865A patent/JP2002507607A/ja active Pending
- 1999-03-20 AT AT99911811T patent/ATE277028T1/de not_active IP Right Cessation
- 1999-03-20 ID IDW20002161A patent/ID27494A/id unknown
- 1999-03-20 KR KR1020007010443A patent/KR100572805B1/ko not_active Expired - Lifetime
- 1999-03-20 CN CNB998043648A patent/CN1330642C/zh not_active Expired - Lifetime
- 1999-03-20 BR BR9909047-3A patent/BR9909047A/pt not_active Application Discontinuation
- 1999-03-20 ES ES99911811T patent/ES2229689T3/es not_active Expired - Lifetime
- 1999-03-20 DE DE69920420T patent/DE69920420T2/de not_active Expired - Lifetime
- 1999-03-20 WO PCT/EP1999/001955 patent/WO1999048882A1/fr not_active Ceased
- 1999-03-20 EP EP99911811A patent/EP1066274B1/fr not_active Revoked
- 1999-03-20 HU HU0102062A patent/HUP0102062A2/hu unknown
- 1999-03-20 AU AU30359/99A patent/AU3035999A/en not_active Abandoned
- 1999-03-20 SK SK1423-2000A patent/SK14232000A3/sk unknown
- 1999-03-20 CA CA002323005A patent/CA2323005C/fr not_active Expired - Lifetime
- 1999-03-23 AR ARP990101287A patent/AR018802A1/es unknown
- 1999-04-14 SA SA99191303A patent/SA99191303B1/ar unknown
- 1999-09-20 US US09/646,788 patent/US6429322B1/en not_active Expired - Lifetime
-
2000
- 2000-09-19 ZA ZA200004995A patent/ZA200004995B/en unknown
- 2000-09-22 NO NO20004739A patent/NO20004739L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ID27494A (id) | 2001-04-12 |
| EP1066274A1 (fr) | 2001-01-10 |
| DE69920420D1 (de) | 2004-10-28 |
| CN1294586A (zh) | 2001-05-09 |
| BE1011851A3 (fr) | 2000-02-01 |
| AU3035999A (en) | 1999-10-18 |
| CA2323005A1 (fr) | 1999-09-30 |
| HUP0102062A2 (hu) | 2001-09-28 |
| JP2002507607A (ja) | 2002-03-12 |
| ZA200004995B (en) | 2002-07-05 |
| NO20004739D0 (no) | 2000-09-22 |
| TW539673B (en) | 2003-07-01 |
| KR20010042087A (ko) | 2001-05-25 |
| ES2229689T3 (es) | 2005-04-16 |
| SA99191303B1 (ar) | 2006-08-14 |
| PL343067A1 (en) | 2001-07-30 |
| ATE277028T1 (de) | 2004-10-15 |
| EP1066274B1 (fr) | 2004-09-22 |
| WO1999048882A1 (fr) | 1999-09-30 |
| KR100572805B1 (ko) | 2006-04-25 |
| US6429322B1 (en) | 2002-08-06 |
| BR9909047A (pt) | 2000-12-05 |
| CA2323005C (fr) | 2009-02-24 |
| CN1330642C (zh) | 2007-08-08 |
| AR018802A1 (es) | 2001-12-12 |
| PL197387B1 (pl) | 2008-03-31 |
| SK14232000A3 (sk) | 2002-01-07 |
| NO20004739L (no) | 2000-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8363 | Opposition against the patent |