CA1293496C - Systeme catalytique a faible teneur en sodium pour l'epoxydation d'alcenes - Google Patents

Systeme catalytique a faible teneur en sodium pour l'epoxydation d'alcenes

Info

Publication number: CA1293496C
Authority: CA; Canada
Prior art keywords: catalyst; silver; support; efficiency; redox
Prior art date: 1985-08-12
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

Application number

CA000515866A

Other languages

English (en)

Inventor

Thomas Michael Notermann

Erlind Magnus Thorsteinson

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.)

Dow Technology Investments LLC

Original Assignee

Union Carbide 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.)

1985-08-12

Filing date

1986-08-13

Publication date

1991-12-24

1986-08-13 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1991-12-24 Application granted granted Critical

1991-12-24 Publication of CA1293496C publication Critical patent/CA1293496C/fr

2008-12-24 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 200
150000001336 alkenes Chemical class 0.000 title claims abstract description 66
238000006735 epoxidation reaction Methods 0.000 title claims abstract description 46
239000011734 sodium Substances 0.000 title claims abstract description 43
229910052708 sodium Inorganic materials 0.000 title claims abstract description 41
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 title claims abstract description 40
230000003197 catalytic effect Effects 0.000 title description 26
229910052709 silver Inorganic materials 0.000 claims abstract description 123
239000004332 silver Substances 0.000 claims abstract description 123
238000006243 chemical reaction Methods 0.000 claims abstract description 88
238000000034 method Methods 0.000 claims abstract description 85
150000003839 salts Chemical class 0.000 claims abstract description 48
230000008569 process Effects 0.000 claims abstract description 38
239000007789 gas Substances 0.000 claims abstract description 28
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
239000001301 oxygen Substances 0.000 claims abstract description 20
229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
239000012633 leachable Substances 0.000 claims abstract description 15
239000007787 solid Substances 0.000 claims abstract description 10
239000011949 solid catalyst Substances 0.000 claims abstract 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical group [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 71
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 55
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 28
239000005977 Ethylene Substances 0.000 claims description 27
235000010333 potassium nitrate Nutrition 0.000 claims description 26
239000004323 potassium nitrate Substances 0.000 claims description 13
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
230000002708 enhancing effect Effects 0.000 claims description 3
230000036647 reaction Effects 0.000 abstract description 6
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 121
229940009188 silver Drugs 0.000 description 120
239000000243 solution Substances 0.000 description 67
239000000463 material Substances 0.000 description 62
230000000694 effects Effects 0.000 description 57
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 40
150000001875 compounds Chemical class 0.000 description 37
238000005470 impregnation Methods 0.000 description 35
239000011148 porous material Substances 0.000 description 31
229940093470 ethylene Drugs 0.000 description 26
238000007254 oxidation reaction Methods 0.000 description 26
230000003647 oxidation Effects 0.000 description 25
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 23
239000002904 solvent Substances 0.000 description 22
239000000126 substance Substances 0.000 description 22
229910002092 carbon dioxide Inorganic materials 0.000 description 21
238000004519 manufacturing process Methods 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
238000010438 heat treatment Methods 0.000 description 18
239000008188 pellet Substances 0.000 description 18
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 17
239000000203 mixture Substances 0.000 description 17
239000012071 phase Substances 0.000 description 17
-1 aluminum ion Chemical group 0.000 description 15
239000002245 particle Substances 0.000 description 15
238000002360 preparation method Methods 0.000 description 14
239000000047 product Substances 0.000 description 13
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 12
230000000536 complexating effect Effects 0.000 description 12
239000011591 potassium Substances 0.000 description 12
229910052700 potassium Inorganic materials 0.000 description 12
235000007686 potassium Nutrition 0.000 description 12
229960003975 potassium Drugs 0.000 description 12
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 12
238000012360 testing method Methods 0.000 description 12
238000006722 reduction reaction Methods 0.000 description 11
229910001868 water Inorganic materials 0.000 description 11
239000001569 carbon dioxide Substances 0.000 description 10
150000001768 cations Chemical class 0.000 description 10
239000008139 complexing agent Substances 0.000 description 10
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 10
230000009467 reduction Effects 0.000 description 10
238000011282 treatment Methods 0.000 description 10
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
150000001450 anions Chemical class 0.000 description 9
239000012153 distilled water Substances 0.000 description 9
238000010304 firing Methods 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
239000011737 fluorine Substances 0.000 description 9
235000019000 fluorine Nutrition 0.000 description 9
229940060037 fluorine Drugs 0.000 description 9
230000006872 improvement Effects 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
229960005419 nitrogen Drugs 0.000 description 9
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 8
229940095050 propylene Drugs 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
229930195733 hydrocarbon Natural products 0.000 description 7
150000002430 hydrocarbons Chemical class 0.000 description 7
235000006408 oxalic acid Nutrition 0.000 description 7
150000002924 oxiranes Chemical class 0.000 description 7
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 6
229910052593 corundum Inorganic materials 0.000 description 6
239000010431 corundum Substances 0.000 description 6
230000009849 deactivation Effects 0.000 description 6
229960003750 ethyl chloride Drugs 0.000 description 6
229940012017 ethylenediamine Drugs 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
230000001965 increasing effect Effects 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
239000006187 pill Substances 0.000 description 6
229910001923 silver oxide Inorganic materials 0.000 description 6
238000005406 washing Methods 0.000 description 6
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
230000032683 aging Effects 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
230000007423 decrease Effects 0.000 description 5
150000002222 fluorine compounds Chemical class 0.000 description 5
150000002739 metals Chemical class 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
229910002651 NO3 Inorganic materials 0.000 description 4
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
239000000654 additive Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
230000008901 benefit Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000011575 calcium Substances 0.000 description 4
239000012876 carrier material Substances 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
238000000151 deposition Methods 0.000 description 4
239000012535 impurity Substances 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000011160 research Methods 0.000 description 4
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 4
229910010271 silicon carbide Inorganic materials 0.000 description 4
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 4
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000002411 adverse Effects 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000007942 carboxylates Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000008021 deposition Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
150000002366 halogen compounds Chemical class 0.000 description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
238000012986 modification Methods 0.000 description 3
230000004048 modification Effects 0.000 description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
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238000004904 shortening Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
229910001593 boehmite Inorganic materials 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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230000002939 deleterious effect Effects 0.000 description 2
LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
238000007865 diluting Methods 0.000 description 2
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
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239000012530 fluid Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
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FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
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238000002386 leaching Methods 0.000 description 2
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
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230000002829 reductive effect Effects 0.000 description 2
150000003377 silicon compounds Chemical class 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
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239000002344 surface layer Substances 0.000 description 2
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DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
241000611184 Amphora Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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239000004338 Dichlorodifluoromethane Substances 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
QYHYQHPUNPVNDV-UHFFFAOYSA-N aluminane Chemical compound C1CC[AlH]CC1 QYHYQHPUNPVNDV-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
235000010210 aluminium Nutrition 0.000 description 1
LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 1
230000002528 anti-freeze Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
229910001570 bauxite Inorganic materials 0.000 description 1
229910001680 bayerite Inorganic materials 0.000 description 1
230000002902 bimodal effect Effects 0.000 description 1
HODFCFXCOMKRCG-UHFFFAOYSA-N bitolterol mesylate Chemical compound CS([O-])(=O)=O.C1=CC(C)=CC=C1C(=O)OC1=CC=C(C(O)C[NH2+]C(C)(C)C)C=C1OC(=O)C1=CC=C(C)C=C1 HODFCFXCOMKRCG-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052810 boron oxide Inorganic materials 0.000 description 1
239000011449 brick Substances 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
GKDXQAKPHKQZSC-UHFFFAOYSA-L cadmium(2+);carbonate Chemical class [Cd+2].[O-]C([O-])=O GKDXQAKPHKQZSC-UHFFFAOYSA-L 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000001427 coherent effect Effects 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
230000001609 comparable effect Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229940049920 malate Drugs 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940073584 methylene chloride Drugs 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
CZDSWLXAULJYPZ-UHFFFAOYSA-J molybdenum(4+);dicarbonate Chemical compound [Mo+4].[O-]C([O-])=O.[O-]C([O-])=O CZDSWLXAULJYPZ-UHFFFAOYSA-J 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
LMAZKPOSWVOFGY-FBAUPLQOSA-N orine Natural products CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C=Cc5ccccc5)[C@]6(C)[C@@](O)(CC[C@]6(O)[C@]4(O)CC=C3C2)[C@H](C)OC(=O)C=Cc7ccccc7)O[C@H](C)[C@H]1O LMAZKPOSWVOFGY-FBAUPLQOSA-N 0.000 description 1
229940039748 oxalate Drugs 0.000 description 1
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
238000012856 packing Methods 0.000 description 1
238000005192 partition Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
VSAISIQCTGDGPU-UHFFFAOYSA-N phosphorus trioxide Inorganic materials O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000012495 reaction gas Substances 0.000 description 1
238000010079 rubber tapping Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
150000003378 silver Chemical class 0.000 description 1
229940100890 silver compound Drugs 0.000 description 1
150000003379 silver compounds Chemical class 0.000 description 1
LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
229940044603 styrene Drugs 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 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
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Catalysts (AREA)
Epoxy Compounds (AREA)

CA000515866A 1985-08-12 1986-08-13 Systeme catalytique a faible teneur en sodium pour l'epoxydation d'alcenes Expired - Lifetime CA1293496C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US76506785A	1985-08-12	1985-08-12
US765,067		1985-08-13

Publications (1)

Publication Number	Publication Date
CA1293496C true CA1293496C (fr)	1991-12-24

Family

ID=25072547

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000515866A Expired - Lifetime CA1293496C (fr)	1985-08-12	1986-08-13	Systeme catalytique a faible teneur en sodium pour l'epoxydation d'alcenes

Country Status (1)

Country	Link
CA (1)	CA1293496C (fr)

1986
- 1986-08-13 CA CA000515866A patent/CA1293496C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2008-12-24	MKEX	Expiry

Publication	Publication Date	Title
US4994587A (en)	1991-02-19	Catalytic system for epoxidation of alkenes employing low sodium catalyst supports
US4994588A (en)	1991-02-19	Fluorine-containing catalytic system for expoxidation of alkenes
US4994589A (en)	1991-02-19	Catalytic system for epoxidation of alkenes
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CN1867400B (zh)	2010-04-14	用于烯化氧制备的具有提高稳定性、效率和/或活性的催化剂
KR0147853B1 (ko)	1998-08-17	활성 및/또는 안정성이 개선된 알킬렌 옥사이드 촉매
CA2783604C (fr)	2018-05-01	Procede pour l'initiation d'epoxydation
CA2232942C (fr)	2005-01-04	Procede de preparation de catalyseurs d'epoxydation
US5801259A (en)	1998-09-01	Ethylene oxide catalyst and process
FI89681B (fi)	1993-07-30	Etylenoxidkatalysator och foerfarande foer katalytisk framstaellning av etylenoxid
EP0989976B1 (fr)	2002-04-24	Procede d'epoxydation mettant en oeuvre des catalyseurs sur support d'argent, prealablement traites a l'aide de chlorure organique
RU2328491C2 (ru)	2008-07-10	Способ эпоксидирования олефинов и катализатор для применения в способе
JP2544925B2 (ja)	1996-10-16	銀含有触媒の製造方法
KR101324286B1 (ko)	2013-11-01	저농도 산화 성분의 존재하의 불활성 기체 중에서의 하소
JPH04330938A (ja)	1992-11-18	担持された銀触媒、ならびにその製造方法及び使用方法
JP4866235B2 (ja)	2012-02-01	酸化エチレン触媒
KR102203848B1 (ko)	2021-01-15	에틸렌 옥사이드의 제조 방법
JP3825797B2 (ja)	2006-09-27	エポキシ化触媒
KR102155073B1 (ko)	2020-09-11	후-컨디셔닝 단계를 이용하는 에폭시화 공정
CA2784609A1 (fr)	2011-06-30	Procede d'epoxydation et microstructure
JP3210337B2 (ja)	2001-09-17	３，４−エポキシ−１−ブテンの製造方法
CA1286687C (fr)	1991-07-23	Fabrication de l'oxyde d'alcene
CA2783605A1 (fr)	2011-07-14	Procede pour la production d'oxyde d'olefine
CA1289936C (fr)	1991-10-01	Systeme catalytique au fluor pour l'epoxydation des alkenes
JP2001157839A (ja)	2001-06-12	エポキシド製造用触媒及びその調製方法並びにエポキシドの製造方法