DE60109783T2 - Verfahren zur herstellung von oxiranen - Google Patents
Verfahren zur herstellung von oxiranen Download PDFInfo
- Publication number
- DE60109783T2 DE60109783T2 DE60109783T DE60109783T DE60109783T2 DE 60109783 T2 DE60109783 T2 DE 60109783T2 DE 60109783 T DE60109783 T DE 60109783T DE 60109783 T DE60109783 T DE 60109783T DE 60109783 T2 DE60109783 T2 DE 60109783T2
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- oxirane
- olefin
- 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.)
- Revoked
Links
- 238000000034 method Methods 0.000 title claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 150000002924 oxiranes Chemical class 0.000 title description 2
- -1 peroxide compound Chemical class 0.000 claims abstract description 54
- 150000001336 alkenes Chemical class 0.000 claims abstract description 53
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 49
- 238000004821 distillation Methods 0.000 claims abstract description 44
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 20
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 20
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 5
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 4
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003990 capacitor Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 239000006227 byproduct Substances 0.000 abstract description 10
- 239000010457 zeolite Substances 0.000 description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 7
- 229910021536 Zeolite Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical class CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000012429 reaction media Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 241000196324 Embryophyta Species 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 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
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- OHRGJTQCDUURLT-UHFFFAOYSA-N 1-(chloromethoxy)propan-1-ol Chemical class CCC(O)OCCl OHRGJTQCDUURLT-UHFFFAOYSA-N 0.000 description 1
- HUXDTFZDCPYTCF-UHFFFAOYSA-N 1-chloropropane-1,1-diol Chemical compound CCC(O)(O)Cl HUXDTFZDCPYTCF-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000007921 spray Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0008354A FR2810982B1 (fr) | 2000-06-28 | 2000-06-28 | Procede de fabrication d'oxiranne comprenant la separation de l'oxiranne du milieu reactionnel |
| FR0008354 | 2000-06-28 | ||
| PCT/EP2001/007271 WO2002000635A1 (fr) | 2000-06-28 | 2001-06-26 | Procede de fabrication d'oxiranne |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60109783D1 DE60109783D1 (de) | 2005-05-04 |
| DE60109783T2 true DE60109783T2 (de) | 2006-01-26 |
Family
ID=8851834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60109783T Revoked DE60109783T2 (de) | 2000-06-28 | 2001-06-26 | Verfahren zur herstellung von oxiranen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6723861B2 (https=) |
| EP (1) | EP1299369B1 (https=) |
| JP (2) | JP5258135B2 (https=) |
| CN (1) | CN1198810C (https=) |
| AT (1) | ATE292125T1 (https=) |
| AU (1) | AU2001276368A1 (https=) |
| BR (1) | BR0111939A (https=) |
| CA (1) | CA2411790C (https=) |
| DE (1) | DE60109783T2 (https=) |
| ES (1) | ES2239151T3 (https=) |
| FR (1) | FR2810982B1 (https=) |
| MX (1) | MX238533B (https=) |
| RU (1) | RU2259362C2 (https=) |
| WO (1) | WO2002000635A1 (https=) |
| ZA (1) | ZA200210153B (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002366573A1 (en) | 2001-12-05 | 2003-06-23 | Dow Global Technologies Inc. | Process of preparing an olefin oxide from olefin and organic hydroperoxide |
| DE10233383A1 (de) * | 2002-07-23 | 2004-02-12 | Basf Ag | Verfahren zur kontinuierlich betriebenen Zwischenabtrennung des bei der koppelproduktfreien Oxiransynthese entstehenden Oxirans unter Verwendung einer Trennwandkolonne |
| US7169945B2 (en) | 2002-11-26 | 2007-01-30 | Degussa Ag | Process for the epoxidation of olefins |
| EP1424332A1 (en) * | 2002-11-26 | 2004-06-02 | Degussa AG | Process for the purification of crude propene oxide |
| WO2008087657A2 (en) * | 2007-01-15 | 2008-07-24 | Aditya Birla Science & Technology Limited | A process for preparing epichlorohydrin |
| US8558020B2 (en) | 2007-04-05 | 2013-10-15 | Solvay (Societe Anonyme) | Aqueous hydrogen peroxide solution, process for its preparation and use thereof |
| 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 |
| US9169226B2 (en) | 2010-07-14 | 2015-10-27 | Dow Global Technologies Llc | Process and assembly for producing alkylene oxides and glycol ethers |
| KR101872391B1 (ko) * | 2010-10-11 | 2018-06-28 | 차이나 페트로리움 앤드 케미컬 코포레이션 | 올레핀 에폭시화를 통한 산화 올레핀의 제조 방법 |
| CN103347868A (zh) | 2011-01-27 | 2013-10-09 | 索尔维公司 | 用于制造1，2-环氧-3-氯丙烷的方法 |
| WO2012101176A1 (en) | 2011-01-27 | 2012-08-02 | Solvay Sa | Process for the manufacture of 1,2-epoxy-3-chloropropane |
| 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 |
| NL2024242B1 (en) * | 2019-11-15 | 2021-07-29 | New Green World B V | Process to continuously prepare a cyclic carbonate |
| CA3158990A1 (en) * | 2019-11-15 | 2021-05-20 | New Green World B.V. | Process to continuously prepare a cyclic carbonate |
| CN115244040A (zh) * | 2020-03-27 | 2022-10-25 | 住友化学株式会社 | 环氧丙烷的制造装置和环氧丙烷的制造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5523426A (en) * | 1995-01-04 | 1996-06-04 | Arco Chemical Technology, L.P. | Integrated process for epoxidation |
| US5912367A (en) * | 1997-07-01 | 1999-06-15 | Arco Chemical Technology, L.P. | High efficiency epoxidation process |
| 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. |
| 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 FR0008354A patent/FR2810982B1/fr not_active Expired - Lifetime
-
2001
- 2001-06-26 ES ES01953991T patent/ES2239151T3/es not_active Expired - Lifetime
- 2001-06-26 AT AT01953991T patent/ATE292125T1/de not_active IP Right Cessation
- 2001-06-26 DE DE60109783T patent/DE60109783T2/de not_active Revoked
- 2001-06-26 CA CA2411790A patent/CA2411790C/fr not_active Expired - Lifetime
- 2001-06-26 MX MXPA02012471 patent/MX238533B/es active IP Right Grant
- 2001-06-26 EP EP01953991A patent/EP1299369B1/fr not_active Revoked
- 2001-06-26 US US10/297,927 patent/US6723861B2/en not_active Expired - Lifetime
- 2001-06-26 WO PCT/EP2001/007271 patent/WO2002000635A1/fr not_active Ceased
- 2001-06-26 AU AU2001276368A patent/AU2001276368A1/en not_active Abandoned
- 2001-06-26 CN CNB018121454A patent/CN1198810C/zh not_active Expired - Lifetime
- 2001-06-26 RU RU2003102384/04A patent/RU2259362C2/ru active
- 2001-06-26 BR BR0111939-7A patent/BR0111939A/pt not_active Application Discontinuation
- 2001-06-26 JP JP2002505383A patent/JP5258135B2/ja not_active Expired - Lifetime
-
2002
- 2002-12-13 ZA ZA200210153A patent/ZA200210153B/en unknown
-
2012
- 2012-12-10 JP JP2012269535A patent/JP2013049726A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20030187285A1 (en) | 2003-10-02 |
| EP1299369A1 (fr) | 2003-04-09 |
| CA2411790C (fr) | 2011-10-11 |
| EP1299369B1 (fr) | 2005-03-30 |
| DE60109783D1 (de) | 2005-05-04 |
| FR2810982B1 (fr) | 2002-09-27 |
| AU2001276368A1 (en) | 2002-01-08 |
| WO2002000635A1 (fr) | 2002-01-03 |
| ATE292125T1 (de) | 2005-04-15 |
| CN1198810C (zh) | 2005-04-27 |
| MXPA02012471A (es) | 2003-06-06 |
| US6723861B2 (en) | 2004-04-20 |
| FR2810982A1 (fr) | 2002-01-04 |
| ZA200210153B (en) | 2004-03-15 |
| RU2259362C2 (ru) | 2005-08-27 |
| JP2013049726A (ja) | 2013-03-14 |
| CA2411790A1 (fr) | 2002-01-03 |
| JP5258135B2 (ja) | 2013-08-07 |
| MX238533B (es) | 2006-07-07 |
| ES2239151T3 (es) | 2005-09-16 |
| BR0111939A (pt) | 2003-05-13 |
| CN1440397A (zh) | 2003-09-03 |
| JP2004501906A (ja) | 2004-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8363 | Opposition against the patent | ||
| 8331 | Complete revocation |