DE60132700T2 - Herstellung von oxiranen mittels einer peroxi-verbindung - Google Patents
Herstellung von oxiranen mittels einer peroxi-verbindung Download PDFInfo
- Publication number
- DE60132700T2 DE60132700T2 DE60132700T DE60132700T DE60132700T2 DE 60132700 T2 DE60132700 T2 DE 60132700T2 DE 60132700 T DE60132700 T DE 60132700T DE 60132700 T DE60132700 T DE 60132700T DE 60132700 T2 DE60132700 T2 DE 60132700T2
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- olefin
- oxirane
- peroxide compound
- catalyst
- 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
- -1 PEROXIDE COMPOUND Chemical class 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000002924 oxiranes Chemical class 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 52
- 150000001336 alkenes Chemical class 0.000 claims abstract description 41
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 33
- 230000008569 process Effects 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 22
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 17
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 17
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 15
- 238000006735 epoxidation reaction Methods 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 6
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 11
- 239000010457 zeolite Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229910021536 Zeolite Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 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
- 239000007788 liquid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000183024 Populus tremula Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- GTDOPRQDTRLYAL-UHFFFAOYSA-N hydrogen peroxide;methanol Chemical compound OC.OO GTDOPRQDTRLYAL-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 150000002823 nitrates Chemical class 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
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0008355 | 2000-06-28 | ||
| FR0008355A FR2810983B1 (fr) | 2000-06-28 | 2000-06-28 | Procede de fabrication d'oxiranne au moyen d'un compose peroxyde |
| PCT/EP2001/007273 WO2002000637A1 (fr) | 2000-06-28 | 2001-06-26 | Fabrication d'oxiranne au moyen d'un compose peroxyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60132700D1 DE60132700D1 (de) | 2008-03-20 |
| DE60132700T2 true DE60132700T2 (de) | 2009-02-12 |
Family
ID=8851835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60132700T Expired - Lifetime DE60132700T2 (de) | 2000-06-28 | 2001-06-26 | Herstellung von oxiranen mittels einer peroxi-verbindung |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US6677467B2 (https=) |
| EP (1) | EP1299371B1 (https=) |
| JP (2) | JP5196696B2 (https=) |
| CN (1) | CN1245395C (https=) |
| AT (1) | ATE385495T1 (https=) |
| AU (1) | AU2001287559A1 (https=) |
| BR (1) | BR0111973B1 (https=) |
| CA (1) | CA2412546C (https=) |
| DE (1) | DE60132700T2 (https=) |
| ES (1) | ES2301560T3 (https=) |
| FR (1) | FR2810983B1 (https=) |
| MX (1) | MXPA02012665A (https=) |
| RU (1) | RU2256656C2 (https=) |
| WO (1) | WO2002000637A1 (https=) |
| ZA (1) | ZA200210159B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2846964B1 (fr) * | 2002-11-12 | 2006-07-21 | Procede de fabrication de 1,2-epoxy-3-chloropropane | |
| EP2103604A1 (de) * | 2008-03-17 | 2009-09-23 | Evonik Degussa GmbH | Verfahren zur Herstellung von Epichlorhydrin |
| EP2149570A1 (en) * | 2008-08-01 | 2010-02-03 | Hexion Specialty Chemicals Research Belgium S.A. | Process for the manufacture of epichlorohydrin using hydrogen peroxide and a manganese komplex |
| EP2149569A1 (en) | 2008-08-01 | 2010-02-03 | Hexion Specialty Chemicals Research Belgium S.A. | Process for the manufacture of a 1,2-Epoxide |
| CN102442978B (zh) * | 2010-10-11 | 2014-01-15 | 中国石油化工股份有限公司 | 一种烯烃环氧化方法 |
| KR101872391B1 (ko) * | 2010-10-11 | 2018-06-28 | 차이나 페트로리움 앤드 케미컬 코포레이션 | 올레핀 에폭시화를 통한 산화 올레핀의 제조 방법 |
| CN102442976B (zh) * | 2010-10-11 | 2014-01-15 | 中国石油化工股份有限公司 | 烯烃环氧化方法 |
| CN102442979B (zh) * | 2010-10-11 | 2014-10-08 | 中国石油化工股份有限公司 | 一种环氧丙烷的制备方法 |
| KR101819023B1 (ko) | 2010-10-11 | 2018-01-16 | 차이나 페트로리움 앤드 케미컬 코포레이션 | 프로필렌 옥사이드 조산물의 정제 방법 및 프로필렌 옥사이드의 제조 방법 |
| EA201391090A1 (ru) | 2011-01-27 | 2013-12-30 | Солвей Са | Способ получения 1,2-эпокси-3-хлорпропана |
| WO2012101176A1 (en) | 2011-01-27 | 2012-08-02 | Solvay Sa | Process for the manufacture of 1,2-epoxy-3-chloropropane |
| US9290469B2 (en) * | 2011-06-23 | 2016-03-22 | Dow Technology Investments Llc | Production of oxidized olefins |
| CN103641800B (zh) * | 2013-12-12 | 2016-08-17 | 中石化上海工程有限公司 | 环氧丙烷的生产方法 |
| CN103724299B (zh) * | 2013-12-12 | 2015-10-21 | 中石化上海工程有限公司 | 制备环氧丙烷的方法 |
| CN105524019B (zh) * | 2014-09-29 | 2017-12-22 | 中国石油化工股份有限公司 | 一种氧化烯烃的制备方法 |
| JP2024546586A (ja) | 2021-12-22 | 2024-12-26 | ソルベイ（ソシエテ アノニム） | 過酸化水素の新規な製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2137310C (en) * | 1993-12-20 | 2004-02-17 | John C. Jubin Jr. | Catalytic converter and method for highly exothermic reactions |
| BE1011539A3 (fr) * | 1997-11-07 | 1999-10-05 | Solvay | Procede de fabrication d'un compose organique. |
| GB2331071A (en) | 1997-11-11 | 1999-05-12 | Solvay | Manufacture of micro spherical zeolite containing catalyst particles |
| BE1011577A3 (fr) | 1997-11-27 | 1999-11-09 | Solvay | Catalyseur d'epoxydation, son utilisation et procede d'epoxydation en presence de catalyseur. |
| US5849937A (en) * | 1997-12-19 | 1998-12-15 | Arco Chemical Technology, L.P. | Epoxidation process using serially connected cascade of fixed bed reactors |
| BE1011851A3 (fr) | 1998-03-24 | 2000-02-01 | Solvay | Procede de fabrication d'un oxiranne. |
| BE1011852A3 (fr) * | 1998-03-24 | 2000-02-01 | Solvay | Procede de fabrication d'un oxiranne. |
| GB9812742D0 (en) * | 1998-06-12 | 1998-08-12 | Philips Electronics Nv | Active matrix electroluminescent display devices |
| DE19835907A1 (de) | 1998-08-07 | 2000-02-17 | Basf Ag | Verfahren zur Umsetzung einer organischen Verbindung mit einem Hydroperoxid |
| BE1012303A3 (fr) | 1998-11-20 | 2000-09-05 | Solvay | Procede de fabrication d'un oxiranne. |
-
2000
- 2000-06-28 FR FR0008355A patent/FR2810983B1/fr not_active Expired - Fee Related
-
2001
- 2001-06-26 AU AU2001287559A patent/AU2001287559A1/en not_active Abandoned
- 2001-06-26 CA CA2412546A patent/CA2412546C/fr not_active Expired - Lifetime
- 2001-06-26 JP JP2002505385A patent/JP5196696B2/ja not_active Expired - Lifetime
- 2001-06-26 DE DE60132700T patent/DE60132700T2/de not_active Expired - Lifetime
- 2001-06-26 EP EP01967093A patent/EP1299371B1/fr not_active Revoked
- 2001-06-26 WO PCT/EP2001/007273 patent/WO2002000637A1/fr not_active Ceased
- 2001-06-26 MX MXPA02012665A patent/MXPA02012665A/es active IP Right Grant
- 2001-06-26 BR BRPI0111973-7A patent/BR0111973B1/pt not_active IP Right Cessation
- 2001-06-26 CN CNB018148026A patent/CN1245395C/zh not_active Expired - Lifetime
- 2001-06-26 AT AT01967093T patent/ATE385495T1/de not_active IP Right Cessation
- 2001-06-26 RU RU2003102385/04A patent/RU2256656C2/ru active
- 2001-06-26 ES ES01967093T patent/ES2301560T3/es not_active Expired - Lifetime
- 2001-06-26 US US10/311,308 patent/US6677467B2/en not_active Expired - Lifetime
-
2002
- 2002-12-13 ZA ZA200210159A patent/ZA200210159B/en unknown
-
2003
- 2003-08-29 US US10/650,730 patent/US6838571B2/en not_active Expired - Lifetime
-
2012
- 2012-12-10 JP JP2012269523A patent/JP2013079259A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US6838571B2 (en) | 2005-01-04 |
| BR0111973A (pt) | 2003-07-01 |
| DE60132700D1 (de) | 2008-03-20 |
| CA2412546C (fr) | 2011-02-01 |
| EP1299371B1 (fr) | 2008-02-06 |
| MXPA02012665A (es) | 2003-05-14 |
| BR0111973B1 (pt) | 2012-01-10 |
| WO2002000637A1 (fr) | 2002-01-03 |
| US20040039216A1 (en) | 2004-02-26 |
| US6677467B2 (en) | 2004-01-13 |
| CN1449392A (zh) | 2003-10-15 |
| ES2301560T3 (es) | 2008-07-01 |
| JP2013079259A (ja) | 2013-05-02 |
| CN1245395C (zh) | 2006-03-15 |
| ZA200210159B (en) | 2004-03-15 |
| JP2004501908A (ja) | 2004-01-22 |
| FR2810983B1 (fr) | 2004-05-21 |
| EP1299371A1 (fr) | 2003-04-09 |
| RU2256656C2 (ru) | 2005-07-20 |
| US20030109726A1 (en) | 2003-06-12 |
| ATE385495T1 (de) | 2008-02-15 |
| AU2001287559A1 (en) | 2002-01-08 |
| CA2412546A1 (fr) | 2002-01-03 |
| FR2810983A1 (fr) | 2002-01-04 |
| JP5196696B2 (ja) | 2013-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8363 | Opposition against the patent |