ZA200502508B - Process for the epoxidation of olefins - Google Patents
Process for the epoxidation of olefins Download PDFInfo
- Publication number
- ZA200502508B ZA200502508B ZA200502508A ZA200502508A ZA200502508B ZA 200502508 B ZA200502508 B ZA 200502508B ZA 200502508 A ZA200502508 A ZA 200502508A ZA 200502508 A ZA200502508 A ZA 200502508A ZA 200502508 B ZA200502508 B ZA 200502508B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydrogen peroxide
- reaction
- wppm
- reaction mixture
- epoxidation
- Prior art date
Links
- 238000006735 epoxidation reaction Methods 0.000 title claims abstract description 23
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 40
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000011541 reaction mixture Substances 0.000 claims abstract description 18
- 239000002585 base Substances 0.000 claims abstract description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 4
- 230000001737 promoting effect Effects 0.000 claims abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 4
- 150000001768 cations Chemical class 0.000 claims abstract 4
- 239000003054 catalyst Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 229910021536 Zeolite Inorganic materials 0.000 claims description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 4
- 239000010457 zeolite Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000007791 liquid phase Substances 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 239000002826 coolant Substances 0.000 claims 1
- 239000007792 gaseous phase Substances 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 8
- 239000010936 titanium Substances 0.000 description 8
- 229910052719 titanium Inorganic materials 0.000 description 8
- 239000012535 impurity Substances 0.000 description 6
- 230000007774 longterm Effects 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000010979 pH adjustment Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000008043 acidic salts Chemical class 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- SNDGLCYYBKJSOT-UHFFFAOYSA-N 1,1,3,3-tetrabutylurea Chemical compound CCCCN(CCCC)C(=O)N(CCCC)CCCC SNDGLCYYBKJSOT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- -1 alkaline earth metal salts Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000012224 working solution 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20020021966 EP1403259A1 (en) | 2002-09-30 | 2002-09-30 | Process for the epoxidation of olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200502508B true ZA200502508B (en) | 2006-03-29 |
Family
ID=31970343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200502508A ZA200502508B (en) | 2002-09-30 | 2006-01-19 | Process for the epoxidation of olefins |
Country Status (15)
| Country | Link |
|---|---|
| EP (2) | EP1403259A1 (zh) |
| JP (1) | JP2006512296A (zh) |
| KR (1) | KR101053812B1 (zh) |
| CN (1) | CN1315816C (zh) |
| AT (1) | ATE320423T1 (zh) |
| AU (1) | AU2003283254A1 (zh) |
| BR (1) | BR0314969A (zh) |
| CA (1) | CA2500402C (zh) |
| DE (1) | DE60304058T2 (zh) |
| ES (1) | ES2258232T3 (zh) |
| MY (1) | MY131852A (zh) |
| PL (1) | PL216070B1 (zh) |
| RU (1) | RU2320650C2 (zh) |
| WO (1) | WO2004029032A1 (zh) |
| ZA (1) | ZA200502508B (zh) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101183715B1 (ko) | 2004-11-18 | 2012-09-17 | 에스케이이노베이션 주식회사 | 과산화수소를 이용한 올레핀의 에폭시화 방법 |
| ITMI20070932A1 (it) * | 2007-05-08 | 2008-11-09 | Basf Ag | Procedimento per la preparazione di un ossido olefinico |
| EP2103604A1 (de) | 2008-03-17 | 2009-09-23 | Evonik Degussa GmbH | Verfahren zur Herstellung von Epichlorhydrin |
| US8524926B2 (en) | 2009-11-19 | 2013-09-03 | Dow Global Technologies Llc | Epoxidation of an olefin |
| US8785670B2 (en) | 2010-12-07 | 2014-07-22 | Basf Se | Process for the production of propylene oxide |
| MY157638A (en) * | 2010-12-07 | 2016-07-15 | Basf Se | Process for the production of propylene oxide |
| EP2719692A1 (en) * | 2012-10-09 | 2014-04-16 | Momentive Specialty Chemicals Research Belgium S.A. | Catalytic epoxidation process |
| CN106467504A (zh) * | 2015-08-20 | 2017-03-01 | 陕西煤业化工集团(上海)胜帮化工技术有限公司 | Hppo法制环氧丙烷并联反应方法 |
| ES2772695T3 (es) | 2015-12-02 | 2020-07-08 | Evonik Operations Gmbh | Procedimiento para la epoxidación de propeno |
| WO2018205244A1 (en) | 2017-05-12 | 2018-11-15 | Evonik Degussa Gmbh | Process for the epoxidation of propene |
| CN108640889B (zh) * | 2018-06-25 | 2022-07-05 | 洛阳市科创石化科技开发有限公司 | 一种低碳烯烃氧化制备低碳环氧烃类化合物的装置及方法 |
| CN110256376B (zh) | 2019-06-14 | 2022-07-19 | 大连理工大学 | 一种丙烯和过氧化氢气相环氧化合成环氧丙烷的流态化反应方法 |
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 |
| US5912367A (en) * | 1997-07-01 | 1999-06-15 | Arco Chemical Technology, L.P. | High efficiency epoxidation process |
| IT1298337B1 (it) * | 1998-03-05 | 1999-12-20 | Enichem Spa | Procedimento per la preparazione di epossidi olefinici. |
| BE1011851A3 (fr) * | 1998-03-24 | 2000-02-01 | Solvay | Procede de fabrication d'un oxiranne. |
| IT1313572B1 (it) * | 1999-07-27 | 2002-09-09 | Enichem Spa | Procedimento per la preparazione di epossidi. |
| IT1313571B1 (it) * | 1999-07-27 | 2002-09-09 | Enichem Spa | Procedimento per la preparazione di ossidi olefinici. |
| DE19944839A1 (de) * | 1999-09-18 | 2001-03-22 | Degussa | Verfahren zur Herstellung von Epoxiden aus Olefinen |
| FR2809729A1 (fr) * | 2000-05-31 | 2001-12-07 | Solvay | Procede de fabrication d'un oxiranne |
| IT1318681B1 (it) * | 2000-08-11 | 2003-08-27 | Enichem Spa | Procedimento integrato per la preparazione di epossidi. |
| EP1247805A1 (en) * | 2001-03-05 | 2002-10-09 | Degussa AG | Process for the epoxidation of olefins |
-
2002
- 2002-09-30 EP EP20020021966 patent/EP1403259A1/en not_active Withdrawn
-
2003
- 2003-09-23 AT AT03775165T patent/ATE320423T1/de not_active IP Right Cessation
- 2003-09-23 WO PCT/EP2003/010559 patent/WO2004029032A1/en active IP Right Grant
- 2003-09-23 RU RU2005113689/04A patent/RU2320650C2/ru active
- 2003-09-23 DE DE60304058T patent/DE60304058T2/de not_active Expired - Lifetime
- 2003-09-23 CA CA2500402A patent/CA2500402C/en not_active Expired - Fee Related
- 2003-09-23 ES ES03775165T patent/ES2258232T3/es not_active Expired - Lifetime
- 2003-09-23 PL PL374491A patent/PL216070B1/pl unknown
- 2003-09-23 EP EP03775165A patent/EP1556366B1/en not_active Expired - Lifetime
- 2003-09-23 KR KR1020057005336A patent/KR101053812B1/ko active IP Right Grant
- 2003-09-23 AU AU2003283254A patent/AU2003283254A1/en not_active Abandoned
- 2003-09-23 CN CNB038234149A patent/CN1315816C/zh not_active Expired - Lifetime
- 2003-09-23 BR BR0314969-2A patent/BR0314969A/pt not_active Application Discontinuation
- 2003-09-23 JP JP2004538987A patent/JP2006512296A/ja not_active Withdrawn
- 2003-09-26 MY MYPI20033684A patent/MY131852A/en unknown
-
2006
- 2006-01-19 ZA ZA200502508A patent/ZA200502508B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004029032A1 (en) | 2004-04-08 |
| AU2003283254A8 (en) | 2004-04-19 |
| KR101053812B1 (ko) | 2011-08-03 |
| CA2500402A1 (en) | 2004-04-08 |
| RU2005113689A (ru) | 2006-01-27 |
| RU2320650C2 (ru) | 2008-03-27 |
| DE60304058T2 (de) | 2006-09-21 |
| CN1315816C (zh) | 2007-05-16 |
| AU2003283254A1 (en) | 2004-04-19 |
| BR0314969A (pt) | 2005-08-02 |
| JP2006512296A (ja) | 2006-04-13 |
| KR20050084604A (ko) | 2005-08-26 |
| EP1556366B1 (en) | 2006-03-15 |
| PL216070B1 (pl) | 2014-02-28 |
| MY131852A (en) | 2007-09-28 |
| EP1403259A1 (en) | 2004-03-31 |
| EP1556366A1 (en) | 2005-07-27 |
| CN1684947A (zh) | 2005-10-19 |
| PL374491A1 (en) | 2005-10-31 |
| ES2258232T3 (es) | 2006-08-16 |
| DE60304058D1 (de) | 2006-05-11 |
| CA2500402C (en) | 2011-01-04 |
| ATE320423T1 (de) | 2006-04-15 |
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