CA1108632A - Obtention d'oxyde d'ethylene - Google Patents

Obtention d'oxyde d'ethylene

Info

Publication number: CA1108632A
Authority: CA; Canada
Prior art keywords: silver; complexing agent; amine; ethylene; catalyst
Prior art date: 1975-12-29
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

Application number

CA359,163A

Other languages

English (en)

Inventor

Stanley B. Cavitt

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.)

Texaco Development 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.)

1975-12-29

Filing date

1980-08-27

Publication date

1981-09-08

1975-12-29 Priority claimed from US05/644,704 external-priority patent/US4102820A/en

1976-12-24 Priority claimed from CA268,764A external-priority patent/CA1093053A/fr

1980-08-27 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1980-08-27 Priority to CA359,163A priority Critical patent/CA1108632A/fr

1981-09-08 Application granted granted Critical

1981-09-08 Publication of CA1108632A publication Critical patent/CA1108632A/fr

Status Expired legal-status Critical Current

Links

IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title claims abstract description 16
238000004519 manufacturing process Methods 0.000 title claims description 4
229910052709 silver Inorganic materials 0.000 claims abstract description 84
239000004332 silver Substances 0.000 claims abstract description 84
239000003054 catalyst Substances 0.000 claims abstract description 70
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 52
238000000034 method Methods 0.000 claims abstract description 49
150000001412 amines Chemical class 0.000 claims abstract description 43
-1 silver car-boxylate Chemical class 0.000 claims abstract description 39
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 30
239000005977 Ethylene Substances 0.000 claims abstract description 30
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 24
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 23
239000003112 inhibitor Substances 0.000 claims abstract description 14
229910001882 dioxygen Inorganic materials 0.000 claims abstract description 13
229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 12
239000001569 carbon dioxide Substances 0.000 claims abstract description 12
239000003039 volatile agent Substances 0.000 claims abstract description 9
239000012808 vapor phase Substances 0.000 claims abstract description 7
238000002485 combustion reaction Methods 0.000 claims abstract description 3
239000000463 material Substances 0.000 claims description 36
239000008139 complexing agent Substances 0.000 claims description 27
XNGYKPINNDWGGF-UHFFFAOYSA-L silver oxalate Chemical group [Ag+].[Ag+].[O-]C(=O)C([O-])=O XNGYKPINNDWGGF-UHFFFAOYSA-L 0.000 claims description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
230000008569 process Effects 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 14
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 13
229920000768 polyamine Polymers 0.000 claims description 13
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
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 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 10
239000011148 porous material Substances 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
239000007789 gas Substances 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
230000003381 solubilizing effect Effects 0.000 claims description 9
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims description 4
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical group NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
125000001033 ether group Chemical group 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
150000002780 morpholines Chemical class 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 2
YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 claims 2
150000004885 piperazines Chemical class 0.000 claims 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
150000002763 monocarboxylic acids Chemical class 0.000 claims 1
239000000758 substrate Substances 0.000 abstract description 23
238000006735 epoxidation reaction Methods 0.000 abstract description 5
150000003378 silver Chemical class 0.000 abstract description 5
239000003795 chemical substances by application Substances 0.000 abstract description 4
229940009188 silver Drugs 0.000 description 69
239000000243 solution Substances 0.000 description 61
229940093470 ethylene Drugs 0.000 description 23
239000008367 deionised water Substances 0.000 description 15
229910021641 deionized water Inorganic materials 0.000 description 15
239000002002 slurry Substances 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
229960004424 carbon dioxide Drugs 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
229960003903 oxygen Drugs 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000003085 diluting agent Substances 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
238000005070 sampling Methods 0.000 description 7
238000001816 cooling Methods 0.000 description 6
229920001281 polyalkylene Polymers 0.000 description 6
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
229910017974 NH40H Inorganic materials 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000001035 drying Methods 0.000 description 5
229940012017 ethylenediamine Drugs 0.000 description 5
238000005470 impregnation Methods 0.000 description 5
229910000069 nitrogen hydride Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
229910001220 stainless steel Inorganic materials 0.000 description 5
239000010935 stainless steel Substances 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000002360 explosive Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical class [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000005979 thermal decomposition reaction Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
238000001994 activation Methods 0.000 description 2
230000004913 activation Effects 0.000 description 2
125000004103 aminoalkyl group Chemical group 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000000151 deposition Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
238000007654 immersion Methods 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000005416 organic matter Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
230000002028 premature Effects 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
229930195734 saturated hydrocarbon Natural products 0.000 description 2
CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 2
229940071536 silver acetate Drugs 0.000 description 2
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 2
229910001958 silver carbonate Inorganic materials 0.000 description 2
229960001124 trientine Drugs 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 1
PAOXFRSJRCGJLV-UHFFFAOYSA-N 2-[4-(2-aminoethyl)piperazin-1-yl]ethanamine Chemical compound NCCN1CCN(CCN)CC1 PAOXFRSJRCGJLV-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
DCCXSCIRSRPUJX-UHFFFAOYSA-N 2-oxopropanoic acid;silver Chemical compound [Ag].CC(=O)C(O)=O DCCXSCIRSRPUJX-UHFFFAOYSA-N 0.000 description 1
XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical compound CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
235000019628 coolness Nutrition 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
LGQRIMRZKJJQTC-UHFFFAOYSA-L disilver;propanedioate Chemical compound [Ag+].[Ag+].[O-]C(=O)CC([O-])=O LGQRIMRZKJJQTC-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
ZEWAYSHJQFFWIH-UHFFFAOYSA-N ethane-1,2-diamine;silver Chemical compound [Ag].NCCN ZEWAYSHJQFFWIH-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
QATBRNFTOCXULG-UHFFFAOYSA-N n'-[2-(methylamino)ethyl]ethane-1,2-diamine Chemical compound CNCCNCCN QATBRNFTOCXULG-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000002683 reaction inhibitor Substances 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229940071575 silver citrate Drugs 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
RUJQWQMCBPWFDO-UHFFFAOYSA-M silver;2-hydroxyacetate Chemical compound [Ag+].OCC([O-])=O RUJQWQMCBPWFDO-UHFFFAOYSA-M 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
FTNNQMMAOFBTNJ-UHFFFAOYSA-M silver;formate Chemical compound [Ag+].[O-]C=O FTNNQMMAOFBTNJ-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
QUTYHQJYVDNJJA-UHFFFAOYSA-K trisilver;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Ag+].[Ag+].[Ag+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QUTYHQJYVDNJJA-UHFFFAOYSA-K 0.000 description 1
238000013022 venting Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1

Landscapes

Catalysts (AREA)

CA359,163A 1975-12-29 1980-08-27 Obtention d'oxyde d'ethylene Expired CA1108632A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA359,163A CA1108632A (fr)	1975-12-29	1980-08-27	Obtention d'oxyde d'ethylene

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US05/644,704 US4102820A (en)	1975-12-29	1975-12-29	Silver catalyst for ethylene epoxidation
US644,704		1975-12-29
US69708876A	1976-06-16	1976-06-16
US697,088		1976-06-16
CA268,764A CA1093053A (fr)	1975-12-29	1976-12-24	Production d'oxyde d'ethylene
CA359,163A CA1108632A (fr)	1975-12-29	1980-08-27	Obtention d'oxyde d'ethylene

Publications (1)

Publication Number	Publication Date
CA1108632A true CA1108632A (fr)	1981-09-08

Family

ID=27425969

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA359,163A Expired CA1108632A (fr)	1975-12-29	1980-08-27	Obtention d'oxyde d'ethylene

Country Status (1)

Country	Link
CA (1)	CA1108632A (fr)

1980
- 1980-08-27 CA CA359,163A patent/CA1108632A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-09-08	MKEX	Expiry

Publication	Publication Date	Title
CA1093542A (fr)	1981-01-13	Catalyseur modifie a base d'oxyde d'ethylene
AU682207B2 (en)	1997-09-25	Process for preparing silver catalyst
US4102820A (en)	1978-07-25	Silver catalyst for ethylene epoxidation
CA1197226A (fr)	1985-11-26	Catalyseurs a l'argent, leur preparation, et leur emploi en production de l'oxyde d'ethylene
CA2697771C (fr)	2018-09-04	Support pour catalyseur d'oxyde d'olefine
US4342667A (en)	1982-08-03	Process for preparing a silver catalyst
US4321206A (en)	1982-03-23	Ethylene oxide production
US4206128A (en)	1980-06-03	Ethylene oxide production
KR101324286B1 (ko)	2013-11-01	저농도 산화 성분의 존재하의 불활성 기체 중에서의 하소
US7507844B2 (en)	2009-03-24	Nanometer scale restructuring of alumina carrier surface and catalysts for the production of alkene oxides
CA1250277A (fr)	1989-02-21	Procede pour la preparation de catalyseurs a base d'argent
CA1093053A (fr)	1981-01-06	Production d'oxyde d'ethylene
US4374260A (en)	1983-02-15	Ethylene oxide production
CA1190213A (fr)	1985-07-09	Catalyseur a l'argent, et methode de fabrication de l'oxyde d'ethylene
US6673949B2 (en)	2004-01-06	Process for the epoxidation of hydrocarbons
CA1133884A (fr)	1982-10-19	Procede d'obtention d'un catalyseur a base d'oxyde d'ethylene
CA1108632A (fr)	1981-09-08	Obtention d'oxyde d'ethylene
CA1138408A (fr)	1982-12-28	Procede d'obtention d'un catalyseur argentique
US5602070A (en)	1997-02-11	Process for preparing silver catalyst
US4235757A (en)	1980-11-25	Ethylene epoxidation catalyst