BR0309690B1 - Processo para a epoxidação de olefinas - Google Patents
Processo para a epoxidação de olefinas Download PDFInfo
- Publication number
- BR0309690B1 BR0309690B1 BRPI0309690-4A BR0309690A BR0309690B1 BR 0309690 B1 BR0309690 B1 BR 0309690B1 BR 0309690 A BR0309690 A BR 0309690A BR 0309690 B1 BR0309690 B1 BR 0309690B1
- Authority
- BR
- Brazil
- Prior art keywords
- product
- process according
- stream
- solvent
- hydrogenation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 72
- 230000008569 process Effects 0.000 title claims abstract description 61
- 238000006735 epoxidation reaction Methods 0.000 title claims abstract description 55
- 239000000047 product Substances 0.000 claims abstract description 96
- 239000002904 solvent Substances 0.000 claims abstract description 80
- 239000003054 catalyst Substances 0.000 claims abstract description 70
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 69
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 52
- 150000001336 alkenes Chemical class 0.000 claims abstract description 37
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 32
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 20
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 163
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 82
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 45
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 238000004821 distillation Methods 0.000 claims description 22
- 239000001294 propane Substances 0.000 claims description 21
- 238000000926 separation method Methods 0.000 claims description 19
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 18
- 238000012545 processing Methods 0.000 claims description 18
- 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
- 238000009835 boiling Methods 0.000 claims description 15
- 239000012535 impurity Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 238000000895 extractive distillation Methods 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- 239000006227 byproduct Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052681 coesite Inorganic materials 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 229910052906 cristobalite Inorganic materials 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- 239000008188 pellet Substances 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 229910052697 platinum 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
- 229910052682 stishovite Inorganic materials 0.000 claims description 3
- 229910052905 tridymite Inorganic materials 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-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
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 20
- 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 9
- 230000009849 deactivation Effects 0.000 description 8
- 150000001728 carbonyl compounds Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- -1 peroxide compounds Chemical class 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-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
- 239000002798 polar solvent Substances 0.000 description 4
- 239000010970 precious metal Substances 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 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
- 230000008901 benefit Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000012043 crude product Substances 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
- 239000002243 precursor Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical class 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
- 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
- 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
- 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
- 229910052799 carbon Inorganic materials 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
- 238000010924 continuous production Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XKZGGGYFMSBEJK-UHFFFAOYSA-N 1,1-dimethoxyethane;lead Chemical compound [Pb].COC(C)OC XKZGGGYFMSBEJK-UHFFFAOYSA-N 0.000 description 1
- LGTUXDWECPSIQO-UHFFFAOYSA-N 1-hydroperoxypropan-2-ol Chemical compound CC(O)COO LGTUXDWECPSIQO-UHFFFAOYSA-N 0.000 description 1
- CGHALRGHFXEMJB-UHFFFAOYSA-N 2-hydroperoxypropan-1-ol Chemical compound OCC(C)OO CGHALRGHFXEMJB-UHFFFAOYSA-N 0.000 description 1
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 description 1
- CPARISZOCHEKFP-UHFFFAOYSA-N COCOC.C(=O)O Chemical compound COCOC.C(=O)O CPARISZOCHEKFP-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011324 bead Substances 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009477 fluid bed granulation 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
- 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
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000011017 operating method Methods 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- YSZUKWLZJXGOTF-UHFFFAOYSA-N propane Chemical compound CCC.CCC YSZUKWLZJXGOTF-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
- 239000002994 raw material Substances 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
- 238000011160 research Methods 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
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000011877 solvent mixture 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
- 238000012546 transfer Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02009869A EP1359148A1 (en) | 2002-05-02 | 2002-05-02 | Process for the epoxidation of olefins |
| EP02009869.5 | 2002-05-02 | ||
| PCT/EP2003/004442 WO2003093255A1 (en) | 2002-05-02 | 2003-04-29 | Process for the epoxidation of olefins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR0309690A BR0309690A (pt) | 2005-03-15 |
| BR0309690B1 true BR0309690B1 (pt) | 2015-01-06 |
Family
ID=28799680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0309690-4A BR0309690B1 (pt) | 2002-05-02 | 2003-04-29 | Processo para a epoxidação de olefinas |
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 |
|---|---|---|---|---|
| KR101363833B1 (ko) * | 2005-12-27 | 2014-02-14 | 바스프 에스이 | 프로펜의 에폭시화 방법 |
| ITMI20052491A1 (it) * | 2005-12-27 | 2007-06-28 | Basf Ag | Un procedimento per la epossidazione del 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 |
| KR101771387B1 (ko) | 2014-07-29 | 2017-08-24 | 에보닉 데구사 게엠베하 | 올레핀의 에폭시화 방법 |
| MD4364C1 (ro) * | 2015-02-17 | 2016-03-31 | Институт Химии Академии Наук Молдовы | Catalizator de epoxidare heterogenă a (+)-3-carenei |
| MY165609A (en) | 2015-04-28 | 2018-04-16 | Evonik Degussa Gmbh | Process for the epoxidation of propene |
| KR102648446B1 (ko) | 2015-11-25 | 2024-03-15 | 에보닉 오퍼레이션스 게엠베하 | 프로펜 및 과산화수소로부터 프로필렌 글리콜의 제조 방법 |
| 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 |
| EP3380459B1 (en) | 2015-11-26 | 2020-01-01 | Evonik Operations GmbH | Process for the epoxidation of an olefin |
| EA035589B1 (ru) | 2015-11-26 | 2020-07-13 | Эвоник Оперейшнс Гмбх | Способ эпоксидирования пропена |
| KR102648943B1 (ko) | 2015-11-26 | 2024-03-18 | 에보닉 오퍼레이션스 게엠베하 | 프로펜의 에폭시화를 위한 방법 및 반응기 |
| WO2017093204A1 (en) * | 2015-12-02 | 2017-06-08 | Evonik Degussa Gmbh | Process for the epoxidation of propene |
| 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 |
| MY183767A (en) | 2016-01-19 | 2021-03-12 | Evonik Operations Gmbh | Process for the epoxidation of an olefin |
| 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 |
| CN108884065B (zh) | 2016-03-21 | 2022-06-07 | 赢创运营有限公司 | 丙烯的环氧化方法 |
| 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 |
| 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 |
| 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 |
| CN113968830B (zh) * | 2020-07-24 | 2024-01-09 | 中国石油化工股份有限公司 | 环氧丙烷物流的分离方法和环氧化反应产物分离方法以及丙烯环氧化方法 |
| CN113968772B (zh) * | 2020-07-24 | 2024-08-13 | 中国石油化工股份有限公司 | 提纯方法及设备和混合物流处理方法和装置以及制备环氧化物的方法和环氧化反应系统 |
| CN112679318A (zh) * | 2020-12-28 | 2021-04-20 | 胜帮科技股份有限公司 | 一种环氧丙烷生产过程中循环溶剂的净化回收装置及方法 |
| CN113636914B (zh) * | 2021-09-14 | 2024-04-12 | 湖南长炼新材料科技股份公司 | 一种丙烯环氧化回收醇溶剂的处理方法 |
| CN115869957A (zh) * | 2021-09-28 | 2023-03-31 | 中国石油化工股份有限公司 | 催化剂及其制备方法和烯烃环氧化反应的回收溶剂加氢精制的方法 |
| 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 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP1074548B1 (en) * | 1999-08-06 | 2006-01-11 | Repsol Quimica S.A. | A method for continuous production of propylene oxide and other alkene oxides |
| EP1122248A1 (de) * | 2000-02-07 | 2001-08-08 | Degussa AG | Verfahren zur Epoxidierung von Olefinen |
| IT1318550B1 (it) * | 2000-06-01 | 2003-08-27 | Eni Spa | Catalizzatore e processo per la sintesi diretta di acqua ossigenata. |
| IT1318549B1 (it) * | 2000-06-01 | 2003-08-27 | Eni Spa | Processo per la produzioni in continuo di acqua ossigenata. |
-
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 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 PL PL371503A patent/PL213135B1/pl unknown
- 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 EP EP03722565.3A patent/EP1499602B2/en not_active Expired - Lifetime
- 2003-04-29 RU RU2004135312/04A patent/RU2322442C2/ru active
- 2003-04-29 BR BRPI0309690-4A patent/BR0309690B1/pt not_active IP Right Cessation
- 2003-04-29 AU AU2003229745A patent/AU2003229745A1/en not_active Abandoned
- 2003-04-29 WO PCT/EP2003/004442 patent/WO2003093255A1/en not_active Ceased
- 2003-04-29 DE DE60304169.8T patent/DE60304169T3/de not_active Expired - Lifetime
- 2003-04-29 KR KR1020047017566A patent/KR100814310B1/ko not_active Expired - Fee Related
- 2003-04-29 ES ES03722565T patent/ES2258718T5/es not_active Expired - Lifetime
-
2004
- 2004-11-01 ZA ZA2004/08821A patent/ZA200408821B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR100814310B1 (ko) | 2008-03-18 |
| DE60304169T2 (de) | 2007-05-10 |
| CN1649858A (zh) | 2005-08-03 |
| WO2003093255A1 (en) | 2003-11-13 |
| EP1499602A1 (en) | 2005-01-26 |
| CA2483447C (en) | 2011-08-09 |
| AU2003229745A1 (en) | 2003-11-17 |
| CA2483447A1 (en) | 2003-11-13 |
| EP1359148A1 (en) | 2003-11-05 |
| PL371503A1 (en) | 2005-06-27 |
| RU2004135312A (ru) | 2005-10-10 |
| AU2003229745A8 (en) | 2003-11-17 |
| BR0309690A (pt) | 2005-03-15 |
| KR20050016382A (ko) | 2005-02-21 |
| DE60304169T3 (de) | 2015-01-08 |
| ES2258718T3 (es) | 2006-09-01 |
| ZA200408821B (en) | 2005-11-30 |
| JP2005526844A (ja) | 2005-09-08 |
| PL213135B1 (pl) | 2013-01-31 |
| DE60304169D1 (de) | 2006-05-11 |
| MY135540A (en) | 2008-05-30 |
| ATE321034T1 (de) | 2006-04-15 |
| JP5183009B2 (ja) | 2013-04-17 |
| EP1499602B1 (en) | 2006-03-22 |
| EP1499602B2 (en) | 2014-11-26 |
| ES2258718T5 (es) | 2015-03-10 |
| CN1294125C (zh) | 2007-01-10 |
| RU2322442C2 (ru) | 2008-04-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BR0309690B1 (pt) | Processo para a epoxidação de olefinas | |
| JP4705373B2 (ja) | 粗製プロペンオキサイドの精製方法 | |
| EP1565449B1 (en) | Process for the epoxidation of olefins | |
| JP2005526844A5 (enExample) | ||
| CA2416554A1 (en) | Process for the continuous production of an olefinic oxide using hydrogen peroxide | |
| WO2018205244A1 (en) | Process for the epoxidation of propene | |
| US7141683B2 (en) | Process for the epoxidation of olefins | |
| US7169945B2 (en) | Process for the epoxidation of olefins | |
| RU2853621C1 (ru) | Способ эпоксидирования пропена | |
| EA044186B1 (ru) | Способ эпоксидирования пропена | |
| EP3438101A1 (en) | Process for the epoxidation of propene | |
| HK40019857A (en) | Process for the epoxidation of propene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B25D | Requested change of name of applicant approved |
Owner name: UHDE GMBH. (DE) , DEGUSSA GMBH (DE) Free format text: NOME ALTERADO DE: DEGUSSA AG |
|
| B25D | Requested change of name of applicant approved |
Owner name: UHDE GMBH. (DE) , EVONIK DEGUSSA GMBH (DE) Free format text: NOME ALTERADO DE: DEGUSSA GMBH |
|
| B25G | Requested change of headquarter approved |
Owner name: UHDE GMBH. (DE) , EVONIK DEGUSSA GMBH (DE) Free format text: ENDERECO ALTERADO CONFORME SOLICITADO NA PETICAO NO 020100037415/RJ DE 29/04/2010. |
|
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 10 (DEZ) ANOS CONTADOS A PARTIR DE 06/01/2015, OBSERVADAS AS CONDICOES LEGAIS. |
|
| B21F | Lapse acc. art. 78, item iv - on non-payment of the annual fees in time |
Free format text: REFERENTE A 16A ANUIDADE. |
|
| B24J | Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12) |
Free format text: EM VIRTUDE DA EXTINCAO PUBLICADA NA RPI 2512 DE 26-02-2019 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDA A EXTINCAO DA PATENTE E SEUS CERTIFICADOS, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |