DE10137784A1 - Verfahren zur Herstellung von Alkenoxiden aus Alkenen - Google Patents
Verfahren zur Herstellung von Alkenoxiden aus AlkenenInfo
- Publication number
- DE10137784A1 DE10137784A1 DE10137784A DE10137784A DE10137784A1 DE 10137784 A1 DE10137784 A1 DE 10137784A1 DE 10137784 A DE10137784 A DE 10137784A DE 10137784 A DE10137784 A DE 10137784A DE 10137784 A1 DE10137784 A1 DE 10137784A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrocarbon
- adsorber
- adsorbent
- gas
- oxygen
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims abstract description 15
- 150000001336 alkenes Chemical class 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 50
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 49
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 38
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 30
- 239000003463 adsorbent Substances 0.000 claims abstract description 27
- 230000003647 oxidation Effects 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000001301 oxygen Substances 0.000 claims abstract description 22
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 15
- 230000003197 catalytic effect Effects 0.000 claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 239000007789 gas Substances 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 238000001179 sorption measurement Methods 0.000 claims description 20
- 238000003795 desorption Methods 0.000 claims description 13
- 239000012495 reaction gas Substances 0.000 claims description 9
- 239000010457 zeolite Substances 0.000 claims description 7
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 238000006884 silylation reaction Methods 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 19
- 229910052739 hydrogen Inorganic materials 0.000 description 19
- 229910001868 water Inorganic materials 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000008929 regeneration Effects 0.000 description 9
- 238000011069 regeneration method Methods 0.000 description 9
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000012876 carrier material Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 5
- 239000003570 air Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 229910001882 dioxygen Inorganic materials 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000002336 sorption--desorption measurement Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 238000003980 solgel method Methods 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012694 precious metal precursor Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
-
- 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
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10137784A DE10137784A1 (de) | 2001-08-02 | 2001-08-02 | Verfahren zur Herstellung von Alkenoxiden aus Alkenen |
| SG200204324A SG105552A1 (en) | 2001-08-02 | 2002-07-12 | Process for the preparation of alkene oxides from alkenes |
| EP02016266A EP1281706A1 (de) | 2001-08-02 | 2002-07-23 | Verfahren zur Herstellung von Alkenoxiden aus Alkenen |
| CA002396530A CA2396530A1 (en) | 2001-08-02 | 2002-07-30 | Process for the preparation of alkene oxides from alkenes |
| CN02127366A CN1405160A (zh) | 2001-08-02 | 2002-07-30 | 由烯烃制备烯烃氧化物的方法 |
| BR0202972-3A BR0202972A (pt) | 2001-08-02 | 2002-07-30 | Processo para a preparação de óxidos de alqueno a partir de alquenos |
| JP2002223271A JP2003176280A (ja) | 2001-08-02 | 2002-07-31 | 炭化水素の触媒部分酸化 |
| US10/210,693 US20030045734A1 (en) | 2001-08-02 | 2002-07-31 | Process for the preparation of alkene oxides from alkenes |
| PL02355268A PL355268A1 (en) | 2001-08-02 | 2002-07-31 | Catalytic process for partial oxidation of hydrocarbons |
| MXPA02007459A MXPA02007459A (es) | 2001-08-02 | 2002-08-01 | Proceso para la preparacion de oxidos de alqueno a partir de alquenos. |
| KR1020020045551A KR20030013300A (ko) | 2001-08-02 | 2002-08-01 | 알켄으로부터 알켄 옥사이드를 제조하는 방법 |
| RU2002120525/04A RU2002120525A (ru) | 2001-08-02 | 2002-08-01 | Способ выделения алкиленоксидов из реакционной смеси, полученной каталитическим частичным окислением алкенов в присутствии кослорода и, по крайней мере, одного восстановителя |
| HU0202560A HUP0202560A2 (hu) | 2001-08-02 | 2002-08-02 | Eljárás alkén-oxidok előállítására alkénekből |
| HK03104955.2A HK1052700A1 (zh) | 2001-08-02 | 2003-07-09 | 由烯烴製備烯烴氧化物的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10137784A DE10137784A1 (de) | 2001-08-02 | 2001-08-02 | Verfahren zur Herstellung von Alkenoxiden aus Alkenen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10137784A1 true DE10137784A1 (de) | 2003-02-13 |
Family
ID=7694057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10137784A Withdrawn DE10137784A1 (de) | 2001-08-02 | 2001-08-02 | Verfahren zur Herstellung von Alkenoxiden aus Alkenen |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20030045734A1 (enExample) |
| EP (1) | EP1281706A1 (enExample) |
| JP (1) | JP2003176280A (enExample) |
| KR (1) | KR20030013300A (enExample) |
| CN (1) | CN1405160A (enExample) |
| BR (1) | BR0202972A (enExample) |
| CA (1) | CA2396530A1 (enExample) |
| DE (1) | DE10137784A1 (enExample) |
| HK (1) | HK1052700A1 (enExample) |
| HU (1) | HUP0202560A2 (enExample) |
| MX (1) | MXPA02007459A (enExample) |
| PL (1) | PL355268A1 (enExample) |
| RU (1) | RU2002120525A (enExample) |
| SG (1) | SG105552A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10137826A1 (de) * | 2001-08-02 | 2003-02-13 | Bayer Ag | Verfahren zur Herstellung und Isolierung von Alkenoxiden aus Alkenen |
| NL1020603C2 (nl) * | 2002-05-15 | 2003-11-18 | Tno | Werkwijze voor het drogen van een product met behulp van een regeneratief adsorbens. |
| JP4824569B2 (ja) | 2003-10-16 | 2011-11-30 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | アルキレンオキサイド製造用の増強された安定性、効率及び／又は活性を有する触媒 |
| US6884898B1 (en) * | 2003-12-08 | 2005-04-26 | Arco Chemical Technology, L.P. | Propylene oxide process |
| US7238817B1 (en) * | 2006-02-22 | 2007-07-03 | Lyondell Chemical Technology, L.P. | Direct epoxidation process |
| EP2532411A1 (de) | 2011-06-10 | 2012-12-12 | Süd-Chemie AG | Druckwechseladsorptionsverfahren |
| CN110201487B (zh) * | 2019-06-24 | 2021-06-25 | 浙江天采云集科技股份有限公司 | 一种乙烯法制环氧乙烷中高纯度高收率甲烷致稳气净化与再利用方法 |
| CN114082383B (zh) * | 2021-12-27 | 2023-08-08 | 红宝丽集团泰兴化学有限公司 | 环氧化反应稳定性的提升方法及提升装置 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2172025A (en) * | 1939-09-05 | Manufacture ofethylene oxide | ||
| US4692535A (en) * | 1986-12-22 | 1987-09-08 | Atlantic Richfield Company | Purification of propylene oxide |
| EP0557116B1 (en) * | 1992-02-20 | 1996-12-18 | Arco Chemical Technology, Inc. | Lower alkylene oxide purification |
| ZA935853B (en) * | 1992-08-21 | 1994-06-10 | Boc Group Inc | Process for producing hydrocarbon partial oxidation products |
| JP4646409B2 (ja) * | 1999-04-08 | 2011-03-09 | ダウ グローバル テクノロジーズ インコーポレイティド | 酸化された金触媒を使用してオレフィンをオレフィンオキシドにハイドロ酸化するための方法 |
| DE10137826A1 (de) * | 2001-08-02 | 2003-02-13 | Bayer Ag | Verfahren zur Herstellung und Isolierung von Alkenoxiden aus Alkenen |
| DE10137783A1 (de) * | 2001-08-02 | 2003-02-13 | Bayer Ag | Verfahren zur Herstellung von Epoxiden aus Alkenen |
| DE10139531A1 (de) * | 2001-08-10 | 2003-02-20 | Bayer Ag | Verfahren zur Epoxidierung von Kohlenwasserstoffen |
-
2001
- 2001-08-02 DE DE10137784A patent/DE10137784A1/de not_active Withdrawn
-
2002
- 2002-07-12 SG SG200204324A patent/SG105552A1/en unknown
- 2002-07-23 EP EP02016266A patent/EP1281706A1/de not_active Withdrawn
- 2002-07-30 CN CN02127366A patent/CN1405160A/zh active Pending
- 2002-07-30 BR BR0202972-3A patent/BR0202972A/pt not_active Application Discontinuation
- 2002-07-30 CA CA002396530A patent/CA2396530A1/en not_active Abandoned
- 2002-07-31 US US10/210,693 patent/US20030045734A1/en not_active Abandoned
- 2002-07-31 PL PL02355268A patent/PL355268A1/xx not_active Application Discontinuation
- 2002-07-31 JP JP2002223271A patent/JP2003176280A/ja active Pending
- 2002-08-01 KR KR1020020045551A patent/KR20030013300A/ko not_active Withdrawn
- 2002-08-01 MX MXPA02007459A patent/MXPA02007459A/es not_active Application Discontinuation
- 2002-08-01 RU RU2002120525/04A patent/RU2002120525A/ru not_active Application Discontinuation
- 2002-08-02 HU HU0202560A patent/HUP0202560A2/hu unknown
-
2003
- 2003-07-09 HK HK03104955.2A patent/HK1052700A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL355268A1 (en) | 2003-02-10 |
| HK1052700A1 (zh) | 2003-09-26 |
| MXPA02007459A (es) | 2005-06-20 |
| CA2396530A1 (en) | 2003-02-02 |
| RU2002120525A (ru) | 2004-02-20 |
| HUP0202560A2 (hu) | 2004-01-28 |
| JP2003176280A (ja) | 2003-06-24 |
| BR0202972A (pt) | 2003-05-27 |
| HU0202560D0 (enExample) | 2002-10-28 |
| CN1405160A (zh) | 2003-03-26 |
| EP1281706A1 (de) | 2003-02-05 |
| US20030045734A1 (en) | 2003-03-06 |
| KR20030013300A (ko) | 2003-02-14 |
| SG105552A1 (en) | 2004-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69824148T2 (de) | Verfahren, Katalysator und Vorrichtung zur Herstellung von Acetaldehyd aus Essigsäure | |
| Bienholz et al. | Selective hydrogenolysis of glycerol over copper catalysts both in liquid and vapour phase: Correlation between the copper surface area and the catalyst's activity | |
| DE10241529A1 (de) | Adsorptionsmasse und Verfahren zur Entfernung von Kohlenmonoxid aus Stoffströmen | |
| EP2035118B1 (de) | Verfahren zur entfernung von co aus stoffströmen | |
| EP3529227B1 (en) | Process for producing dienes | |
| CN106673977B (zh) | 一种乙醇直接脱氢制备乙醛的催化剂、制备方法及其应用 | |
| DE10137784A1 (de) | Verfahren zur Herstellung von Alkenoxiden aus Alkenen | |
| DE69206961T2 (de) | Verfahren zur Dehydrierung von Kohlenwasserstoffen und von sauerstoffenthaltenden Kohlenwasserstoffen | |
| EP2285488B1 (de) | Verfahren zur herstellung von gesättigten ethern durch hydrierung ungesättigter ether | |
| DE19847629A1 (de) | Verfahren zur Oxidation einer mindestens eine C-C-Doppelbindung aufweisenden organischen Verbindung | |
| EP1281705A2 (de) | Verfahren zur Herstellung von Epoxiden aus Alkenen | |
| DE10137826A1 (de) | Verfahren zur Herstellung und Isolierung von Alkenoxiden aus Alkenen | |
| DE102005055588A1 (de) | Verfahren zur Isolierung von N2O | |
| CN1124887C (zh) | 碳纳米管促进铜－基甲醇合成催化剂及其制备方法 | |
| EP1477225A1 (de) | Katalysator | |
| DE19845857A1 (de) | Verfahren zur katalytischen Oligomerisierung von Monoolefinen | |
| Abduh et al. | Selective oxidation of cumene into 2-phenyl-2-propanol and acetophenone over activated carbon supported Co1. 5PW12O40 material | |
| Ko et al. | Efficient direct synthesis of 2-ethylhexanal from n-butyraldehyde and hydrogen using palladium modified base catalysts | |
| DE10030637A1 (de) | Katalysatoren auf Basis Erdalkalititanat als Träger für metallisches Gold zur selektiven Oxidation von Kohlenwasserstoffen | |
| CN1305983A (zh) | 香叶醇气相选择氧化制备柠檬醛的方法 | |
| Moens et al. | Oxidation chemistry with nitrous oxide | |
| Petró et al. | Factors influencing activity and selectivity of Palladium Catalystst | |
| DE1197442B (de) | Verfahren zur Herstellung von alpha, beta-ungesaettigten Aldehyden oder Ketonen | |
| DE10300526A1 (de) | Silberhaltige Katalysatoren zur Umsetzung von Substraten mit C-C-Doppelbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |