DE60304169T3 - Verfahren zur epoxidierung von olefinen - Google Patents
Verfahren zur epoxidierung von olefinen Download PDFInfo
- Publication number
- DE60304169T3 DE60304169T3 DE60304169.8T DE60304169T DE60304169T3 DE 60304169 T3 DE60304169 T3 DE 60304169T3 DE 60304169 T DE60304169 T DE 60304169T DE 60304169 T3 DE60304169 T3 DE 60304169T3
- Authority
- DE
- Germany
- Prior art keywords
- solvent
- stream
- catalyst
- hydrogenation
- epoxidation
- 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
- 238000000034 method Methods 0.000 title claims abstract description 54
- 230000008569 process Effects 0.000 title claims abstract description 45
- 239000002904 solvent Substances 0.000 claims abstract description 76
- 239000000047 product Substances 0.000 claims abstract description 75
- 239000003054 catalyst Substances 0.000 claims abstract description 65
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 54
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 43
- 150000001336 alkenes Chemical class 0.000 claims abstract description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 24
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 172
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 74
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 238000004821 distillation Methods 0.000 claims description 21
- 238000000926 separation method Methods 0.000 claims description 18
- 239000010936 titanium Substances 0.000 claims description 16
- 229910052719 titanium Inorganic materials 0.000 claims description 16
- 238000010626 work up procedure Methods 0.000 claims description 15
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910000510 noble metal 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
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 229910052742 iron 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
- 239000000243 solution Substances 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 32
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 22
- 238000009835 boiling Methods 0.000 description 15
- 239000001294 propane Substances 0.000 description 15
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
- 238000000895 extractive distillation Methods 0.000 description 12
- 239000012535 impurity Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 150000001728 carbonyl compounds Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 230000009849 deactivation Effects 0.000 description 7
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 7
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- -1 peroxide compounds Chemical class 0.000 description 5
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000008187 granular material Substances 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
- 239000010970 precious metal Substances 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 compound COCC(C)O ARXJGSRGQADJSQ-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 238000009825 accumulation Methods 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
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CGHALRGHFXEMJB-UHFFFAOYSA-N 2-hydroperoxypropan-1-ol Chemical compound OCC(C)OO CGHALRGHFXEMJB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 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
- 230000000887 hydrating effect Effects 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
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 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
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 238000010517 secondary 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000010457 zeolite 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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02009869A EP1359148A1 (en) | 2002-05-02 | 2002-05-02 | Process for the epoxidation of olefins |
| EP02009869 | 2002-05-02 | ||
| PCT/EP2003/004442 WO2003093255A1 (en) | 2002-05-02 | 2003-04-29 | Process for the epoxidation of olefins |
| EP03722565.3A EP1499602B2 (en) | 2002-05-02 | 2003-04-29 | Process for the epoxidation of olefins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE60304169D1 DE60304169D1 (de) | 2006-05-11 |
| DE60304169T2 DE60304169T2 (de) | 2007-05-10 |
| DE60304169T3 true DE60304169T3 (de) | 2015-01-08 |
Family
ID=28799680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60304169.8T Expired - Lifetime DE60304169T3 (de) | 2002-05-02 | 2003-04-29 | Verfahren zur epoxidierung von olefinen |
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) |
Families Citing this family (35)
| 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 |
| MD4364C1 (ro) * | 2015-02-17 | 2016-03-31 | Институт Химии Академии Наук Молдовы | Catalizator de epoxidare heterogenă a (+)-3-carenei |
| 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 |
| CN110003138B (zh) * | 2019-04-26 | 2021-05-25 | 江苏扬农化工集团有限公司 | 一种用分子筛催化反应脱除hppo工艺中醛酮的方法 |
| 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 |
| CN113968829B (zh) * | 2020-07-24 | 2024-02-09 | 中国石油化工股份有限公司 | 一种丙烯环氧化方法和一种环氧化系统 |
| CN113968831B (zh) * | 2020-07-24 | 2024-02-09 | 中国石油化工股份有限公司 | 环氧丙烷精制方法和环氧丙烷物流的分离方法和环氧化反应产物分离方法及丙烯环氧化方法 |
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| CN119019347B (zh) * | 2023-05-26 | 2025-12-12 | 中国石油化工股份有限公司 | 一种分离粗环氧丙烷中甲缩醛的方法 |
| CN119192100A (zh) * | 2023-06-26 | 2024-12-27 | 中国石油化工股份有限公司 | 环氧丙烷的制备方法和制备环氧丙烷的装置 |
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|---|---|---|---|---|
| US3860662A (en) * | 1967-11-20 | 1975-01-14 | Halcon International Inc | Process for treating the product mixture from the epoxidation of olefinic hydrocarbons |
| JPS5846490B2 (ja) * | 1979-12-12 | 1983-10-17 | 日本合成アルコ−ル株式会社 | 不純アルコ−ルの精製法 |
| US5106458A (en) * | 1991-07-26 | 1992-04-21 | Texaco Chemical Company | Method for the purification of propylene oxide |
| IT1250756B (it) * | 1991-08-02 | 1995-04-21 | Eniricerche Spa | Procedimento per la produzione di ossidi olefinici |
| US5166372A (en) * | 1992-02-07 | 1992-11-24 | Arco Chemical Technology, L.P. | Epoxidation process |
| US5214168A (en) * | 1992-04-30 | 1993-05-25 | Arco Chemical Technology, L.P. | Integrated process for epoxide production |
| CA2137310C (en) * | 1993-12-20 | 2004-02-17 | John C. Jubin Jr. | Catalytic converter and method for highly exothermic reactions |
| US5463090A (en) * | 1994-10-27 | 1995-10-31 | Arco Chemical Technology, L.P. | Integrated process for epoxide production |
| US5693834A (en) * | 1995-03-15 | 1997-12-02 | Arco Chemical Technology, L.P. | Integrated process for epoxidation |
| IT1283455B1 (it) * | 1996-07-19 | 1998-04-21 | Enichem Spa | Procedimento per la preparazione di epossidi da olefine |
| US5863391A (en) * | 1997-08-15 | 1999-01-26 | Arco Chemical Technology, L.P. | Purification of a methanol stream |
| PT1074548E (pt) * | 1999-08-06 | 2006-08-31 | Repsol Quimica Sa | Processo para a producao continua de oxido de propileno e outros oxidos de alcenos |
| EP1122248A1 (de) * | 2000-02-07 | 2001-08-08 | Degussa AG | Verfahren zur Epoxidierung von Olefinen |
| IT1318549B1 (it) * | 2000-06-01 | 2003-08-27 | Eni Spa | Processo per la produzioni in continuo di acqua ossigenata. |
| IT1318550B1 (it) * | 2000-06-01 | 2003-08-27 | Eni Spa | Catalizzatore e processo per la sintesi diretta di acqua ossigenata. |
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2002
- 2002-05-02 EP EP02009869A patent/EP1359148A1/en not_active Withdrawn
-
2003
- 2003-04-28 MY MYPI20031593A patent/MY135540A/en unknown
- 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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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 |
| 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 |
| RU2322442C2 (ru) | 2008-04-20 |
| JP5183009B2 (ja) | 2013-04-17 |
| DE60304169D1 (de) | 2006-05-11 |
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