CA2081942C - Production de catalyseurs pour la production d'alkenylalcanoates - Google Patents

Production de catalyseurs pour la production d'alkenylalcanoates

Info

Publication number: CA2081942C
Authority: CA; Canada
Prior art keywords: catalyst; sodium; potassium; palladium; catalysts
Prior art date: 1991-11-18
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

CA002081942A

Other languages

English (en)

Other versions

CA2081942A1 (fr

Inventor

William J. Bartley

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.)

Union Carbide Chemicals and Plastics Technology LLC

Original Assignee

Union Carbide Chemicals and Plastics Technology LLC

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.)

1991-11-18

Filing date

1992-11-02

Publication date

1997-07-22

1991-05-06 Priority to US07/696,215 priority Critical patent/US5185308A/en

1991-11-18 Priority claimed from US07/793,131 external-priority patent/US5179056A/en

1991-11-18 Priority claimed from US07/793,129 external-priority patent/US5179057A/en

1991-11-18 Priority to US07/793,131 priority patent/US5179056A/en

1991-11-18 Priority to US07/793,129 priority patent/US5179057A/en

1992-03-30 Priority to DE69226626T priority patent/DE69226626T2/de

1992-03-30 Priority to AU13900/92A priority patent/AU643132B2/en

1992-03-30 Priority to AU13911/92A priority patent/AU649117B2/en

1992-03-30 Priority to NZ242166A priority patent/NZ242166A/xx

1992-03-30 Priority to ES92302781T priority patent/ES2118788T3/es

1992-03-30 Priority to EP92302781A priority patent/EP0569624B1/fr

1992-03-30 Priority to HU9201056A priority patent/HU212042B/hu

1992-03-30 Priority to CA002064444A priority patent/CA2064444C/fr

1992-03-30 Priority to AT92302781T priority patent/ATE169520T1/de

1992-03-30 Priority claimed from CN92103424A external-priority patent/CN1036377C/zh

1992-03-30 Priority to PL92294028A priority patent/PL168717B1/pl

1992-03-30 Priority to CN92102172A priority patent/CN1058480C/zh

1992-03-30 Priority claimed from JP07415592A external-priority patent/JP3369209B2/ja

1992-03-30 Priority to JP07415592A priority patent/JP3369209B2/ja

1992-09-28 Priority to US07/952,280 priority patent/US5342987A/en

1992-10-07 Priority to US07/957,143 priority patent/US5274181A/en

1992-11-02 Priority to CA002081942A priority patent/CA2081942C/fr

1992-11-02 Application filed by Union Carbide Chemicals and Plastics Technology LLC filed Critical Union Carbide Chemicals and Plastics Technology LLC

1994-05-03 Publication of CA2081942A1 publication Critical patent/CA2081942A1/fr

1996-01-13 Priority to CN96101006A priority patent/CN1085950C/zh

1997-07-22 Publication of CA2081942C publication Critical patent/CA2081942C/fr

1997-07-22 Application granted granted Critical

2012-11-02 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 254
125000003342 alkenyl group Chemical group 0.000 title claims abstract description 28
238000004519 manufacturing process Methods 0.000 title abstract description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 113
229910052708 sodium Inorganic materials 0.000 claims abstract description 67
239000011734 sodium Substances 0.000 claims abstract description 67
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 claims abstract description 64
238000000034 method Methods 0.000 claims abstract description 62
229910052763 palladium Inorganic materials 0.000 claims abstract description 56
230000000694 effects Effects 0.000 claims abstract description 44
229910052700 potassium Inorganic materials 0.000 claims abstract description 37
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 34
239000010931 gold Substances 0.000 claims abstract description 34
239000011591 potassium Substances 0.000 claims abstract description 33
229910052737 gold Inorganic materials 0.000 claims abstract description 32
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 28
238000006243 chemical reaction Methods 0.000 claims abstract description 13
239000007789 gas Substances 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
239000001301 oxygen Substances 0.000 claims abstract description 10
229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
150000001336 alkenes Chemical class 0.000 claims abstract description 6
239000007858 starting material Substances 0.000 claims abstract description 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 49
239000000243 solution Substances 0.000 claims description 32
230000001376 precipitating effect Effects 0.000 claims description 29
235000011056 potassium acetate Nutrition 0.000 claims description 24
239000002245 particle Substances 0.000 claims description 23
239000003795 chemical substances by application Substances 0.000 claims description 22
238000005406 washing Methods 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
229910001868 water Inorganic materials 0.000 claims description 17
150000002344 gold compounds Chemical class 0.000 claims description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
239000007864 aqueous solution Substances 0.000 claims description 14
239000003638 chemical reducing agent Substances 0.000 claims description 12
238000001035 drying Methods 0.000 claims description 12
150000001768 cations Chemical class 0.000 claims description 5
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
238000006073 displacement reaction Methods 0.000 claims description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 31
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
-1 organic acid salt Chemical class 0.000 description 15
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 11
239000002184 metal Substances 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
239000001632 sodium acetate Substances 0.000 description 11
235000017281 sodium acetate Nutrition 0.000 description 11
229910052783 alkali metal Inorganic materials 0.000 description 10
239000000203 mixture Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
238000001556 precipitation Methods 0.000 description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
239000005977 Ethylene Substances 0.000 description 7
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
239000004115 Sodium Silicate Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000005470 impregnation Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910000510 noble metal Inorganic materials 0.000 description 5
235000011118 potassium hydroxide Nutrition 0.000 description 5
235000019795 sodium metasilicate Nutrition 0.000 description 5
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 5
229910052911 sodium silicate Inorganic materials 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
239000012190 activator Substances 0.000 description 4
239000011324 bead Substances 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
239000011148 porous material Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
150000001242 acetic acid derivatives Chemical class 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910000272 alkali metal oxide Inorganic materials 0.000 description 3
229910052910 alkali metal silicate Inorganic materials 0.000 description 3
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
229910052793 cadmium Inorganic materials 0.000 description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
150000002343 gold Chemical class 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
238000009616 inductively coupled plasma Methods 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
150000002736 metal compounds Chemical class 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000002344 surface layer Substances 0.000 description 3
KGYLMXMMQNTWEM-UHFFFAOYSA-J tetrachloropalladium Chemical compound Cl[Pd](Cl)(Cl)Cl KGYLMXMMQNTWEM-UHFFFAOYSA-J 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
229910020175 SiOH Inorganic materials 0.000 description 2
239000004280 Sodium formate Substances 0.000 description 2
229910045601 alloy Inorganic materials 0.000 description 2
239000000956 alloy Substances 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000011068 loading method Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003112 potassium compounds Chemical class 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000002791 soaking Methods 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
235000019254 sodium formate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
229910000619 316 stainless steel Inorganic materials 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
229910001020 Au alloy Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
229910003803 Gold(III) chloride Inorganic materials 0.000 description 1
239000004594 Masterbatch (MB) Substances 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910004806 Na2 SiO3.9H2 O Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000004645 aluminates Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
159000000006 cesium salts Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000013480 data collection Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
238000009795 derivation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000003353 gold alloy Substances 0.000 description 1
RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
RFLFDJSIZCCYIP-UHFFFAOYSA-L palladium(2+);sulfate Chemical compound [Pd+2].[O-]S([O-])(=O)=O RFLFDJSIZCCYIP-UHFFFAOYSA-L 0.000 description 1
229910000364 palladium(II) sulfate Inorganic materials 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 description 1
239000004331 potassium propionate Substances 0.000 description 1
235000010332 potassium propionate Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
235000019353 potassium silicate Nutrition 0.000 description 1
RWMKSKOZLCXHOK-UHFFFAOYSA-M potassium;butanoate Chemical compound [K+].CCCC([O-])=O RWMKSKOZLCXHOK-UHFFFAOYSA-M 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000010802 sludge Substances 0.000 description 1
235000011091 sodium acetates Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/58—Platinum group metals with alkali- or alkaline earth metals
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/48—Silver or gold
- B01J23/52—Gold
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/06—Washing

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA002081942A 1991-05-06 1992-11-02 Production de catalyseurs pour la production d'alkenylalcanoates Expired - Fee Related CA2081942C (fr)

Priority Applications (19)

Application Number	Priority Date	Filing Date	Title
US07/696,215 US5185308A (en)	1991-05-06	1991-05-06	Catalysts and processes for the manufacture of vinyl acetate
US07/793,131 US5179056A (en)	1991-05-06	1991-11-18	Production of alkenyl alkanoate catalysts
US07/793,129 US5179057A (en)	1991-05-06	1991-11-18	Catalysts for alkenyl alkanoate production
JP07415592A JP3369209B2 (ja)	1991-05-06	1992-03-30	酢酸ビニルを製造するための触媒および方法
CN92102172A CN1058480C (zh)	1991-05-06	1992-03-30	乙酸乙烯酯的制备方法
AU13911/92A AU649117B2 (en)	1991-05-06	1992-03-30	Catalysts and process for the manufacture of vinyl acetate
NZ242166A NZ242166A (en)	1991-11-18	1992-03-30	Alkenyl alkanoate catalyst with reduced sodium content and preparation thereof
ES92302781T ES2118788T3 (es)	1991-05-06	1992-03-30	Catalizadores y procesos para la preparacion de acetato de vinilo.
EP92302781A EP0569624B1 (fr)	1991-05-06	1992-03-30	Catalyseurs et procédés pour la préparation de l'acétate de vinyle
HU9201056A HU212042B (en)	1991-05-06	1992-03-30	Process for preparing shell impregnated catalyst containing gold and palladium, and for preparing vinyl-acetate with said catalyst
CA002064444A CA2064444C (fr)	1991-05-06	1992-03-30	Catalyseurs utilises dans la fabrication de l'acetate de vinyle, et procedes connexes
AT92302781T ATE169520T1 (de)	1991-05-06	1992-03-30	Katalysatoren und verfahren für die herstellung von vinylacetat
DE69226626T DE69226626T2 (de)	1991-05-06	1992-03-30	Katalysatoren und Verfahren für die Herstellung von Vinylacetat
PL92294028A PL168717B1 (pl)	1991-05-06	1992-03-30	winyluUrzad Patentowy Rzeczypospolitej Polskiej PL
AU13900/92A AU643132B2 (en)	1991-11-18	1992-03-30	Alkenyl alkanoate catalyst process
US07/952,280 US5342987A (en)	1991-05-06	1992-09-28	Alkenyl alkanoate production
US07/957,143 US5274181A (en)	1991-05-06	1992-10-07	Catalysts and processes for the manufacture of vinyl acetate
CA002081942A CA2081942C (fr)	1991-11-18	1992-11-02	Production de catalyseurs pour la production d'alkenylalcanoates
CN96101006A CN1085950C (zh)	1991-05-06	1996-01-13	用于制造乙酸乙烯酯的催化剂

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US07/793,131 US5179056A (en)	1991-05-06	1991-11-18	Production of alkenyl alkanoate catalysts
US07/793,129 US5179057A (en)	1991-05-06	1991-11-18	Catalysts for alkenyl alkanoate production
JP07415592A JP3369209B2 (ja)	1991-05-06	1992-03-30	酢酸ビニルを製造するための触媒および方法
CN92103424A CN1036377C (zh)	1991-11-18	1992-03-30	链烯基链烷酸酯催化剂制造方法
CA002081942A CA2081942C (fr)	1991-11-18	1992-11-02	Production de catalyseurs pour la production d'alkenylalcanoates

Publications (2)

Publication Number	Publication Date
CA2081942A1 CA2081942A1 (fr)	1994-05-03
CA2081942C true CA2081942C (fr)	1997-07-22

Family

ID=27508477

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002081942A Expired - Fee Related CA2081942C (fr)	1991-05-06	1992-11-02	Production de catalyseurs pour la production d'alkenylalcanoates

Country Status (1)

Country	Link
CA (1)	CA2081942C (fr)

1992
- 1992-11-02 CA CA002081942A patent/CA2081942C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2081942A1 (fr)	1994-05-03

Legal Events

Date	Code	Title	Description
1992-11-02	EEER	Examination request
2007-11-02	MKLA	Lapsed

Publication	Publication Date	Title
US5179056A (en)	1993-01-12	Production of alkenyl alkanoate catalysts
CA2064412C (fr)	1997-10-14	Obtention d'un catalyseur pour la preparation d'alcanoate d'alcenyle
US5179057A (en)	1993-01-12	Catalysts for alkenyl alkanoate production
CA2064444C (fr)	2001-08-21	Catalyseurs utilises dans la fabrication de l'acetate de vinyle, et procedes connexes
KR100575967B1 (ko)	2006-05-02	칼륨 오레이트로 제조된, 금속 팔라듐 및 금을 포함하는비닐 아세테이트 제조용 촉매
RU2261142C2 (ru)	2005-09-27	Катализатор и способ получения винилацетата
RU2132230C1 (ru)	1999-06-27	Способ получения катализатора для синтеза винилацетата и способ получения винилацетата
KR0142192B1 (ko)	1998-07-01	알릴 아세테이트의 제조방법
KR100589992B1 (ko)	2006-06-15	금속 팔라듐, 구리 및 금을 포함하는 비닐 아세테이트촉매 및 이의 제조방법
KR20060077908A (ko)	2006-07-05	비닐 아세테이트 제조용 촉매 및 그의 용도
US5274181A (en)	1993-12-28	Catalysts and processes for the manufacture of vinyl acetate
KR100575968B1 (ko)	2006-05-02	금속 팔라듐, 구리 및 금을 포함하는 비닐 아세테이트촉매 및 그의 제조방법
US5342987A (en)	1994-08-30	Alkenyl alkanoate production
EP0563414B1 (fr)	1997-02-26	Procédé de préparation de catalyseur pour la production d'un alcanoate d'alkenyle
RU2204548C2 (ru)	2003-05-20	Способ получения катализатора для производства винилацетата (варианты), способ получения винилацетата
CA2081942C (fr)	1997-07-22	Production de catalyseurs pour la production d'alkenylalcanoates
CA2081937C (fr)	1997-07-22	Catalyseurs servant a l'obtention d'alcanoate d'alcenyle
AU762149B2 (en)	2003-06-19	Vinyl acetate catalyst comprising palladium, gold, copper and any of certain fourth metals
MXPA00011854A (en)	2001-09-07	Vinyl acetate catalyst comprising metallic palladium and gold prepared with potassium aurate
MXPA00011853A (en)	2001-09-07	Vinyl acetate catalyst comprising metallic palladium, copper and gold and preparation thereof