RU2322442C2 - Способ эпоксидирования олефинов - Google Patents
Способ эпоксидирования олефинов Download PDFInfo
- Publication number
- RU2322442C2 RU2322442C2 RU2004135312/04A RU2004135312A RU2322442C2 RU 2322442 C2 RU2322442 C2 RU 2322442C2 RU 2004135312/04 A RU2004135312/04 A RU 2004135312/04A RU 2004135312 A RU2004135312 A RU 2004135312A RU 2322442 C2 RU2322442 C2 RU 2322442C2
- Authority
- RU
- Russia
- Prior art keywords
- stream
- hydrogenation
- olefin
- solvent
- propene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 85
- 238000006735 epoxidation reaction Methods 0.000 title claims abstract description 58
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 41
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 230000008569 process Effects 0.000 title abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 84
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 70
- 239000003054 catalyst Substances 0.000 claims abstract description 67
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 55
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 165
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 86
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 47
- 239000000047 product Substances 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 38
- 238000004821 distillation Methods 0.000 claims description 25
- 238000001704 evaporation Methods 0.000 claims description 24
- 230000008020 evaporation Effects 0.000 claims description 24
- 238000009835 boiling Methods 0.000 claims description 20
- 239000001294 propane Substances 0.000 claims description 19
- 239000010936 titanium Substances 0.000 claims description 18
- 229910052719 titanium Inorganic materials 0.000 claims description 18
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 16
- 238000000926 separation method Methods 0.000 claims description 16
- 239000012535 impurity Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 12
- 238000000895 extractive distillation Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 9
- 239000006227 byproduct Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 6
- 150000001241 acetals Chemical class 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 3
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000011343 solid material Substances 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000831 Steel Inorganic materials 0.000 claims 1
- 239000010959 steel Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 239000010970 precious metal Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 230000009849 deactivation Effects 0.000 description 8
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 7
- 230000002262 irrigation Effects 0.000 description 7
- 238000003973 irrigation Methods 0.000 description 7
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 238000009825 accumulation Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- -1 peroxide compounds Chemical class 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000002032 methanolic fraction Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- LGTUXDWECPSIQO-UHFFFAOYSA-N 1-hydroperoxypropan-2-ol Chemical compound CC(O)COO LGTUXDWECPSIQO-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical class COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- CGHALRGHFXEMJB-UHFFFAOYSA-N 2-hydroperoxypropan-1-ol Chemical compound OCC(C)OO CGHALRGHFXEMJB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- GNKTZDSRQHMHLZ-UHFFFAOYSA-N [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] Chemical compound [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] GNKTZDSRQHMHLZ-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011805 ball Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02009869.5 | 2002-05-02 | ||
| EP02009869A EP1359148A1 (en) | 2002-05-02 | 2002-05-02 | Process for the epoxidation of olefins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004135312A RU2004135312A (ru) | 2005-10-10 |
| RU2322442C2 true RU2322442C2 (ru) | 2008-04-20 |
Family
ID=28799680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004135312/04A RU2322442C2 (ru) | 2002-05-02 | 2003-04-29 | Способ эпоксидирования олефинов |
Country Status (15)
| Country | Link |
|---|---|
| EP (2) | EP1359148A1 (enExample) |
| JP (1) | JP5183009B2 (enExample) |
| KR (1) | KR100814310B1 (enExample) |
| CN (1) | CN1294125C (enExample) |
| AT (1) | ATE321034T1 (enExample) |
| AU (1) | AU2003229745A1 (enExample) |
| BR (1) | BR0309690B1 (enExample) |
| CA (1) | CA2483447C (enExample) |
| DE (1) | DE60304169T3 (enExample) |
| ES (1) | ES2258718T5 (enExample) |
| MY (1) | MY135540A (enExample) |
| PL (1) | PL213135B1 (enExample) |
| RU (1) | RU2322442C2 (enExample) |
| WO (1) | WO2003093255A1 (enExample) |
| ZA (1) | ZA200408821B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD4364C1 (ro) * | 2015-02-17 | 2016-03-31 | Институт Химии Академии Наук Молдовы | Catalizator de epoxidare heterogenă a (+)-3-carenei |
| RU2853621C1 (ru) * | 2021-02-03 | 2025-12-25 | Эвоник Оперейшнс Гмбх | Способ эпоксидирования пропена |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20052491A1 (it) | 2005-12-27 | 2007-06-28 | Basf Ag | Un procedimento per la epossidazione del propene |
| WO2007074101A1 (en) * | 2005-12-27 | 2007-07-05 | Basf Se | A process for epoxidizing propene |
| CN101972655B (zh) * | 2010-10-26 | 2012-11-14 | 中国科学院山西煤炭化学研究所 | 一种烯烃环氧化催化剂及其制备方法与应用 |
| CN104926606B (zh) * | 2014-03-21 | 2017-12-12 | 湖南长岭石化科技开发有限公司 | 一种对来自烯烃环氧化反应过程的回收醇溶剂进行纯化的方法和一种烯烃环氧化方法 |
| WO2016016070A1 (en) | 2014-07-29 | 2016-02-04 | Evonik Degussa Gmbh | Process for the epoxidation of an olefin |
| PT3288927T (pt) | 2015-04-28 | 2019-08-06 | Evonik Degussa Gmbh | Processo para a epoxidação de propeno |
| HUE046136T2 (hu) | 2015-11-25 | 2020-02-28 | Evonik Operations Gmbh | Eljárás 1,2-propándiol elõállítására propénból és hidrogén-peroxidból |
| PL3380458T3 (pl) | 2015-11-26 | 2020-03-31 | Evonik Degussa Gmbh | Sposób epoksydowania propenu |
| MY184843A (en) | 2015-11-26 | 2021-04-26 | Evonik Operations Gmbh | Process for the epoxidation of an olefin |
| TWI707847B (zh) | 2015-11-26 | 2020-10-21 | 德商贏創運營有限公司 | 丙烯之環氧化方法 |
| MY185640A (en) | 2015-11-26 | 2021-05-27 | Evonik Operations Gmbh | Process and reactor for the epoxidation of propene |
| CN112898236A (zh) * | 2015-12-02 | 2021-06-04 | 赢创运营有限公司 | 用于环氧化丙烯的方法 |
| CN105481644A (zh) * | 2015-12-02 | 2016-04-13 | 中国天辰工程有限公司 | 一种去除有机溶剂水溶液中过氧化氢的方法 |
| CN108473453B (zh) | 2016-01-19 | 2020-08-04 | 赢创运营有限公司 | 烯烃的环氧化方法 |
| CN105712953A (zh) * | 2016-01-26 | 2016-06-29 | 江苏怡达化学股份有限公司 | 一种预纯化环氧丙烷的方法 |
| EP3433240B1 (en) | 2016-03-21 | 2020-10-28 | Evonik Operations GmbH | Process for the epoxidation of propene |
| EP3246323A1 (en) * | 2016-05-17 | 2017-11-22 | Evonik Degussa GmbH | Integrated process for making propene oxide from propane |
| CN106349016A (zh) * | 2016-08-22 | 2017-01-25 | 江苏怡达化学股份有限公司 | 一种用于甲醇回收的前处理系统及工艺 |
| WO2018205244A1 (en) * | 2017-05-12 | 2018-11-15 | Evonik Degussa Gmbh | Process for the epoxidation of propene |
| EP3406603A1 (en) | 2017-05-22 | 2018-11-28 | Evonik Degussa GmbH | Process for the epoxidation of propene |
| EP3438101A1 (en) | 2017-08-01 | 2019-02-06 | Evonik Degussa GmbH | Process for the epoxidation of propene |
| CN108191794B (zh) * | 2017-12-29 | 2020-02-11 | 中触媒新材料股份有限公司 | 一种丙烯环氧化反应方法 |
| CN110105173A (zh) * | 2019-04-26 | 2019-08-09 | 江苏扬农化工集团有限公司 | 一种高效的hppo工艺回收溶剂的纯化方法 |
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| CN110354858B (zh) * | 2019-08-23 | 2022-04-12 | 湖南长岭石化科技开发有限公司 | 一种烯烃环氧化反应过程的醇溶剂加氢精制催化剂及其制备方法和应用 |
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- 2003-04-29 DE DE60304169.8T patent/DE60304169T3/de not_active Expired - Lifetime
- 2003-04-29 AU AU2003229745A patent/AU2003229745A1/en not_active Abandoned
- 2003-04-29 RU RU2004135312/04A patent/RU2322442C2/ru active
- 2003-04-29 KR KR1020047017566A patent/KR100814310B1/ko not_active Expired - Fee Related
- 2003-04-29 EP EP03722565.3A patent/EP1499602B2/en not_active Expired - Lifetime
- 2003-04-29 ES ES03722565T patent/ES2258718T5/es not_active Expired - Lifetime
- 2003-04-29 JP JP2004501394A patent/JP5183009B2/ja not_active Expired - Fee Related
- 2003-04-29 AT AT03722565T patent/ATE321034T1/de not_active IP Right Cessation
- 2003-04-29 PL PL371503A patent/PL213135B1/pl unknown
- 2003-04-29 BR BRPI0309690-4A patent/BR0309690B1/pt not_active IP Right Cessation
- 2003-04-29 CA CA2483447A patent/CA2483447C/en not_active Expired - Fee Related
- 2003-04-29 CN CNB038099594A patent/CN1294125C/zh not_active Expired - Lifetime
- 2003-04-29 WO PCT/EP2003/004442 patent/WO2003093255A1/en not_active Ceased
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| MD4364C1 (ro) * | 2015-02-17 | 2016-03-31 | Институт Химии Академии Наук Молдовы | Catalizator de epoxidare heterogenă a (+)-3-carenei |
| RU2853621C1 (ru) * | 2021-02-03 | 2025-12-25 | Эвоник Оперейшнс Гмбх | Способ эпоксидирования пропена |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200408821B (en) | 2005-11-30 |
| WO2003093255A1 (en) | 2003-11-13 |
| MY135540A (en) | 2008-05-30 |
| PL213135B1 (pl) | 2013-01-31 |
| JP2005526844A (ja) | 2005-09-08 |
| ATE321034T1 (de) | 2006-04-15 |
| AU2003229745A1 (en) | 2003-11-17 |
| BR0309690A (pt) | 2005-03-15 |
| KR100814310B1 (ko) | 2008-03-18 |
| AU2003229745A8 (en) | 2003-11-17 |
| EP1499602A1 (en) | 2005-01-26 |
| CA2483447C (en) | 2011-08-09 |
| EP1499602B2 (en) | 2014-11-26 |
| DE60304169T3 (de) | 2015-01-08 |
| CA2483447A1 (en) | 2003-11-13 |
| RU2004135312A (ru) | 2005-10-10 |
| DE60304169T2 (de) | 2007-05-10 |
| EP1499602B1 (en) | 2006-03-22 |
| ES2258718T3 (es) | 2006-09-01 |
| CN1294125C (zh) | 2007-01-10 |
| PL371503A1 (en) | 2005-06-27 |
| BR0309690B1 (pt) | 2015-01-06 |
| ES2258718T5 (es) | 2015-03-10 |
| KR20050016382A (ko) | 2005-02-21 |
| EP1359148A1 (en) | 2003-11-05 |
| CN1649858A (zh) | 2005-08-03 |
| JP5183009B2 (ja) | 2013-04-17 |
| DE60304169D1 (de) | 2006-05-11 |
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