CA1266052A - Methode d'epoxydation engendrant un oligomere a faible teneur d'olefine en sous-produit - Google Patents

Methode d'epoxydation engendrant un oligomere a faible teneur d'olefine en sous-produit

Info

Publication number: CA1266052A
Authority: CA; Canada
Prior art keywords: propylene; tbhp; ppm; molybdenum; range
Prior art date: 1984-12-31
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 - Fee Related

Application number

CA000483290A

Other languages

English (en)

Inventor

Edward Thomas Marquis

William Alan Smith

Kenneth Patrick Keating

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Huntsman Specialty Chemicals Corp

Original Assignee

Texaco Development Corp

Priority date (The priority date 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 date listed.)

1984-12-31

Filing date

1985-06-06

Publication date

1990-02-20

1985-06-06 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1990-02-20 Application granted granted Critical

1990-02-20 Publication of CA1266052A publication Critical patent/CA1266052A/fr

2007-02-20 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 87
239000006227 byproduct Substances 0.000 title claims abstract description 17
230000008569 process Effects 0.000 title abstract description 28
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract description 23
230000015572 biosynthetic process Effects 0.000 title abstract description 6
150000001336 alkenes Chemical class 0.000 title description 31
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims abstract description 139
239000003054 catalyst Substances 0.000 claims abstract description 122
229910052750 molybdenum Inorganic materials 0.000 claims abstract description 82
239000011733 molybdenum Substances 0.000 claims abstract description 82
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 78
238000006243 chemical reaction Methods 0.000 claims abstract description 68
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 55
239000000047 product Substances 0.000 claims abstract description 33
125000002947 alkylene group Chemical group 0.000 claims abstract description 21
150000001875 compounds Chemical class 0.000 claims abstract description 20
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 87
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 85
WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 claims description 30
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 28
239000000376 reactant Substances 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 11
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 4
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract description 29
238000006735 epoxidation reaction Methods 0.000 abstract description 22
-1 LOW OLEFIN Chemical class 0.000 abstract description 16
150000002432 hydroperoxides Chemical class 0.000 abstract description 16
238000004821 distillation Methods 0.000 abstract description 5
229940095050 propylene Drugs 0.000 description 78
235000016768 molybdenum Nutrition 0.000 description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 14
WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 10
QMPVWZAMOBOJSY-UHFFFAOYSA-N 2-ethylhexan-1-ol;molybdenum Chemical compound [Mo].CCCCC(CC)CO QMPVWZAMOBOJSY-UHFFFAOYSA-N 0.000 description 9
239000000539 dimer Substances 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
239000012263 liquid product Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
230000007423 decrease Effects 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
125000004429 atom Chemical group 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
230000008901 benefit Effects 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
229910000619 316 stainless steel Inorganic materials 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
QGAVSDVURUSLQK-UHFFFAOYSA-N ammonium heptamolybdate Chemical compound N.N.N.N.N.N.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Mo].[Mo].[Mo].[Mo].[Mo].[Mo].[Mo] QGAVSDVURUSLQK-UHFFFAOYSA-N 0.000 description 4
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
238000011084 recovery Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000004711 α-olefin Substances 0.000 description 4
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000010960 commercial process Methods 0.000 description 3
230000003247 decreasing effect Effects 0.000 description 3
238000000895 extractive distillation Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
239000000463 material Substances 0.000 description 3
239000005078 molybdenum compound Substances 0.000 description 3
150000002752 molybdenum compounds Chemical class 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241001279686 Allium moly Species 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
229910017974 NH40H Inorganic materials 0.000 description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000002411 adverse Effects 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
FIXLYHHVMHXSCP-UHFFFAOYSA-H azane;dihydroxy(dioxo)molybdenum;trioxomolybdenum;tetrahydrate Chemical compound N.N.N.N.N.N.O.O.O.O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O FIXLYHHVMHXSCP-UHFFFAOYSA-H 0.000 description 2
230000006399 behavior Effects 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 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
238000005187 foaming Methods 0.000 description 2
RYPKRALMXUUNKS-UHFFFAOYSA-N hex-2-ene Chemical class CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
230000006872 improvement Effects 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000001282 iso-butane Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
229960004063 propylene glycol Drugs 0.000 description 2
235000013772 propylene glycol Nutrition 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011669 selenium Substances 0.000 description 2
229910052709 silver Inorganic materials 0.000 description 2
239000004332 silver Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
229910052720 vanadium Inorganic materials 0.000 description 2
229940045605 vanadium Drugs 0.000 description 2
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
QIJNJJZPYXGIQM-UHFFFAOYSA-N 1lambda4,2lambda4-dimolybdacyclopropa-1,2,3-triene Chemical compound [Mo]=C=[Mo] QIJNJJZPYXGIQM-UHFFFAOYSA-N 0.000 description 1
XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical group CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
WCMSFBRREKZZFL-UHFFFAOYSA-N 3-cyclohexen-1-yl-Benzene Chemical class C1CCCC(C=2C=CC=CC=2)=C1 WCMSFBRREKZZFL-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
206010015137 Eructation Diseases 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical group BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001334 alicyclic compounds Chemical class 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
XUFUCDNVOXXQQC-UHFFFAOYSA-L azane;hydroxy-(hydroxy(dioxo)molybdenio)oxy-dioxomolybdenum Chemical compound N.N.O[Mo](=O)(=O)O[Mo](O)(=O)=O XUFUCDNVOXXQQC-UHFFFAOYSA-L 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000001935 cyclohexenes Chemical class 0.000 description 1
238000011161 development Methods 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229960004756 ethanol Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000003631 expected effect Effects 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
238000007373 indentation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000002751 molybdenum Chemical class 0.000 description 1
230000007935 neutral effect Effects 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
150000002894 organic compounds Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
150000004685 tetrahydrates Chemical class 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Landscapes

Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000483290A 1984-12-31 1985-06-06 Methode d'epoxydation engendrant un oligomere a faible teneur d'olefine en sous-produit Expired - Fee Related CA1266052A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US68767884A	1984-12-31	1984-12-31
US687,678		1984-12-31

Publications (1)

Publication Number	Publication Date
CA1266052A true CA1266052A (fr)	1990-02-20

Family

ID=24761365

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000483290A Expired - Fee Related CA1266052A (fr)	1984-12-31	1985-06-06	Methode d'epoxydation engendrant un oligomere a faible teneur d'olefine en sous-produit

Country Status (2)

Country	Link
JP (1)	JPH0246584B2 (fr)
CA (1)	CA1266052A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9102641B2 (en)	2007-03-22	2015-08-11	Sumitomo Chemical Company Limited	Method for producing propylene oxide

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001151764A (ja) *	1999-11-19	2001-06-05	Nof Corp	エポキシ化合物の製造方法

1985
- 1985-06-06 CA CA000483290A patent/CA1266052A/fr not_active Expired - Fee Related
- 1985-12-27 JP JP29336485A patent/JPH0246584B2/ja not_active Expired - Lifetime

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9102641B2 (en)	2007-03-22	2015-08-11	Sumitomo Chemical Company Limited	Method for producing propylene oxide

Also Published As

Publication number	Publication date
JPH0246584B2 (ja)	1990-10-16
JPS61161274A (ja)	1986-07-21

Legal Events

Date	Code	Title	Description
2003-02-20	MKLA	Lapsed

Publication	Publication Date	Title
US3953362A (en)	1976-04-27	Molybdenum salt catalysts and methods of preparing them
EP0560488B1 (fr)	1997-05-28	Procédé d'époxydation
US5750741A (en)	1998-05-12	Preparation of oxirane compounds with titanasilsesquioxane catalysts
US4891437A (en)	1990-01-02	Olefin epoxidation of olefins in a polar medium
US5093506A (en)	1992-03-03	Removal of acidic contaminants from tertiary butyl hydroperoxide
EP0608093B1 (fr)	1996-10-09	Procédé d'époxydation pour la préparation d'un oxyde d'oléfine et d'un alcool
EP0193682B1 (fr)	1990-03-07	Synthèse de complexes molybdène/alkylène-glycol utilisables comme catalyseurs d'époxydation
US5151530A (en)	1992-09-29	Treatment of tertiary butyl hydroperoxide distillation fraction to remove acidic contaminants
US4046783A (en)	1977-09-06	Method of olefin epoxidation
US4650886A (en)	1987-03-17	Synthesis of ammonium molybdate/alkanol complexes
US4483997A (en)	1984-11-20	Olefin epoxidation with inorganic metal phosphate enhanced catalyst
EP0264184B1 (fr)	1990-12-19	Complexes molybdène/métal alcalin/éthylèneglycol utilisables comme catalyseurs d'époxydation et leur methode de préparation
US4845251A (en)	1989-07-04	Epoxidation in the presence of molybdenum/alkali metal/ethylene glycol complexes [useful as epoxidation catalysts]
EP0188912B2 (fr)	1998-03-04	Procédé d'époxidation de propylène
US5118822A (en)	1992-06-02	Olefin epoxidation using a perrhenate catalyst and an organic hydroperoxide
US5107067A (en)	1992-04-21	Catalytic reaction of propyelne with tertiary butyl hydroperoxide
US5128492A (en)	1992-07-07	Precipitation of molybdenum
CA1278306C (fr)	1990-12-27	Epoxydation des olefines en milieu polaire
EP0192895B1 (fr)	1989-12-27	Synthèse des complexes molybdène-alcool utilisables comme catalyseurs d'époxydation
CA1278305C (fr)	1990-12-27	Configuration de reacteur pour la production d'oxyde d'alkylene
CA1266054A (fr)	1990-02-20	Procede d'epoxydation utilisant un faible rapport olefine/hydroperoxyde
US4093636A (en)	1978-06-06	Epoxidation of olefinic compounds
US5670674A (en)	1997-09-23	Production of oxirane compounds
CA1266053A (fr)	1990-02-20	Methode d'epoxydation sur catalyseurs au molybdene
EP3377467B1 (fr)	2020-03-25	Sources d'alimentation pour procédés de production de butanediol

CA1266052A - Methode d'epoxydation engendrant un oligomere a faible teneur d'olefine en sous-produit - Google Patents

Info

Links

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=24761365

Family Applications (1)

Country Status (2)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

Similar Documents

Legal Events