CA2161952A1 - Catalyst and process for using same for the preparation of unsaturated carboxylic acid esters - Google Patents
Catalyst and process for using same for the preparation of unsaturated carboxylic acid estersInfo
- Publication number
- CA2161952A1 CA2161952A1 CA002161952A CA2161952A CA2161952A1 CA 2161952 A1 CA2161952 A1 CA 2161952A1 CA 002161952 A CA002161952 A CA 002161952A CA 2161952 A CA2161952 A CA 2161952A CA 2161952 A1 CA2161952 A1 CA 2161952A1
- Authority
- CA
- Canada
- Prior art keywords
- support
- compounds
- grams
- catalyst
- alkali metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 142
- 238000000034 method Methods 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims description 13
- 150000001733 carboxylic acid esters Chemical class 0.000 title description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 107
- 239000010931 gold Substances 0.000 claims abstract description 75
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 239000000203 mixture Substances 0.000 claims abstract description 61
- 229910052751 metal Inorganic materials 0.000 claims abstract description 58
- 239000002184 metal Substances 0.000 claims abstract description 58
- 229910052737 gold Inorganic materials 0.000 claims abstract description 41
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 38
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 32
- -1 palladium group metals Chemical class 0.000 claims abstract description 28
- 239000010949 copper Substances 0.000 claims abstract description 26
- 229910052802 copper Inorganic materials 0.000 claims abstract description 24
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000002585 base Substances 0.000 claims abstract description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 19
- 239000012808 vapor phase Substances 0.000 claims abstract description 18
- 229910052910 alkali metal silicate Inorganic materials 0.000 claims abstract description 17
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 13
- 150000002148 esters Chemical class 0.000 claims abstract description 13
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 11
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 11
- 239000010941 cobalt Substances 0.000 claims abstract description 11
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052709 silver Inorganic materials 0.000 claims abstract description 11
- 239000004332 silver Substances 0.000 claims abstract description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 10
- 229910052742 iron Inorganic materials 0.000 claims abstract description 10
- 239000011133 lead Substances 0.000 claims abstract description 10
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims abstract description 10
- 230000008021 deposition Effects 0.000 claims abstract description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 69
- 229910052763 palladium Inorganic materials 0.000 claims description 37
- 239000000377 silicon dioxide Substances 0.000 claims description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 13
- 150000002895 organic esters Chemical class 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- 238000000151 deposition Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000032683 aging Effects 0.000 claims 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 6
- 238000009736 wetting Methods 0.000 claims 6
- 150000007524 organic acids Chemical class 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 79
- 239000011324 bead Substances 0.000 description 78
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 72
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- 235000011056 potassium acetate Nutrition 0.000 description 36
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 30
- 239000007864 aqueous solution Substances 0.000 description 30
- 239000008367 deionised water Substances 0.000 description 28
- 229910021641 deionized water Inorganic materials 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 239000007921 spray Substances 0.000 description 17
- 238000005507 spraying Methods 0.000 description 16
- 229910002708 Au–Cu Inorganic materials 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- 238000005470 impregnation Methods 0.000 description 13
- 238000011068 loading method Methods 0.000 description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000005977 Ethylene Substances 0.000 description 11
- 235000019353 potassium silicate Nutrition 0.000 description 11
- 239000004111 Potassium silicate Substances 0.000 description 10
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 10
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 10
- 229910052913 potassium silicate Inorganic materials 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 229940117958 vinyl acetate Drugs 0.000 description 10
- 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 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 8
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 8
- PWUXVUCSHRWOOI-UHFFFAOYSA-J [Na].Cl[Au](Cl)(Cl)Cl Chemical compound [Na].Cl[Au](Cl)(Cl)Cl PWUXVUCSHRWOOI-UHFFFAOYSA-J 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 229910003244 Na2PdCl4 Inorganic materials 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 229910000510 noble metal Inorganic materials 0.000 description 7
- 150000002344 gold compounds Chemical class 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 5
- RLQWHDODQVOVKU-UHFFFAOYSA-N tetrapotassium;silicate Chemical compound [K+].[K+].[K+].[K+].[O-][Si]([O-])([O-])[O-] RLQWHDODQVOVKU-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000004115 Sodium Silicate Substances 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229910017398 Au—Ni Inorganic materials 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000518994 Conta Species 0.000 description 3
- 229910016502 CuCl2—2H2O Inorganic materials 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000001639 calcium acetate Substances 0.000 description 3
- 235000011092 calcium acetate Nutrition 0.000 description 3
- 229960005147 calcium acetate Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000004760 silicates Chemical class 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002265 redox agent Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000019795 sodium metasilicate Nutrition 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- 101150098459 SELENOK gene Proteins 0.000 description 1
- 102100023829 Selenoprotein K Human genes 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- IZPZQHISQHRLFP-UHFFFAOYSA-J [Na+].[Na+].[Na+].[Na+].[Cl-].[Cl-].[Cl-].[Cl-] Chemical compound [Na+].[Na+].[Na+].[Na+].[Cl-].[Cl-].[Cl-].[Cl-] IZPZQHISQHRLFP-UHFFFAOYSA-J 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- YIXUBKJRRPSDRB-UHFFFAOYSA-L barium(2+);hexanoate Chemical compound [Ba+2].CCCCCC([O-])=O.CCCCCC([O-])=O YIXUBKJRRPSDRB-UHFFFAOYSA-L 0.000 description 1
- RKNFJIIYAUSTJA-UHFFFAOYSA-N bis(sulfanylidene)platinum Chemical compound S=[Pt]=S RKNFJIIYAUSTJA-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- ZRIHAIZYIMGOAB-UHFFFAOYSA-N butabarbital Chemical compound CCC(C)C1(CC)C(=O)NC(=O)NC1=O ZRIHAIZYIMGOAB-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- HTXDPTMKBJXEOW-UHFFFAOYSA-N dioxoiridium Chemical compound O=[Ir]=O HTXDPTMKBJXEOW-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PMYUVOOOQDGQNW-UHFFFAOYSA-N hexasodium;trioxido(trioxidosilyloxy)silane Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-][Si]([O-])([O-])O[Si]([O-])([O-])[O-] PMYUVOOOQDGQNW-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910000457 iridium oxide Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- MMBKOHVRHFSAJP-UHFFFAOYSA-M lithium;2,2-dimethylpropanoate Chemical compound [Li+].CC(C)(C)C([O-])=O MMBKOHVRHFSAJP-UHFFFAOYSA-M 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 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
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019351 sodium silicates Nutrition 0.000 description 1
- LHYPLJGBYPAQAK-UHFFFAOYSA-M sodium;pentanoate Chemical compound [Na+].CCCCC([O-])=O LHYPLJGBYPAQAK-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- POWFTOSLLWLEBN-UHFFFAOYSA-N tetrasodium;silicate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-][Si]([O-])([O-])[O-] POWFTOSLLWLEBN-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical group C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8926—Copper and noble 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0207—Pretreatment of the support
Landscapes
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/067,445 US5347046A (en) | 1993-05-25 | 1993-05-25 | Catalyst and process for using same for the preparation of unsaturated carboxylic acid esters |
| US08/067,445 | 1993-05-25 | ||
| PCT/US1994/005382 WO1994027720A1 (en) | 1993-05-25 | 1994-05-11 | Catalyst and process for using same for the preparation of unsaturated carboxylic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2161952A1 true CA2161952A1 (en) | 1994-12-08 |
Family
ID=22076033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002161952A Abandoned CA2161952A1 (en) | 1993-05-25 | 1994-05-11 | Catalyst and process for using same for the preparation of unsaturated carboxylic acid esters |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5347046A (enExample) |
| EP (1) | EP0708684A1 (enExample) |
| JP (1) | JP3698322B2 (enExample) |
| KR (1) | KR960702348A (enExample) |
| CN (1) | CN1123527A (enExample) |
| AU (1) | AU6912994A (enExample) |
| BR (1) | BR9406696A (enExample) |
| CA (1) | CA2161952A1 (enExample) |
| TW (1) | TW254934B (enExample) |
| WO (1) | WO1994027720A1 (enExample) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4323980C1 (de) * | 1993-07-16 | 1995-03-30 | Hoechst Ag | Palladium und Kalium sowie Cadmium, Barium oder Gold enthaltender Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung zur Herstellung von Vinylacetat |
| CA2135021A1 (en) * | 1993-11-19 | 1995-05-20 | David J. Gulliver | Process for the preparation of catalysts for use in the production of vinyl acetate |
| US5665668A (en) * | 1994-01-25 | 1997-09-09 | Grigorova; Bojidara | Method of making a catalyst |
| IL112414A (en) * | 1994-01-25 | 1998-08-16 | Anglo American Res Lab Pty Ltd | Method of preparing a catalyst by impregnating a porous support with a solution |
| DE19501891C1 (de) * | 1995-01-23 | 1996-09-26 | Degussa | Verfahren zur Herstellung eines Trägerkatalysators und seine Verwendung für die Produktion von Vinylacetat |
| US5688993A (en) * | 1995-12-22 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Method for modifying catalyst performance during the gas phase synthesis of vinyl acetate |
| DE19623226A1 (de) * | 1996-06-11 | 1997-12-18 | Basf Ag | Katalysatorsysteme vom Typ der Ziegler-Natta-Katalysatoren |
| US5693586A (en) * | 1996-06-28 | 1997-12-02 | Hoechst Celanese Corporation | Palladium-gold catalyst for vinyl acetate production |
| US5731457A (en) * | 1997-06-03 | 1998-03-24 | Hoechst Celanese Corporation | Vinyl acetate process utilizing a palladium-gold-copper catalyst |
| US5968869A (en) * | 1997-06-03 | 1999-10-19 | Celanese International Corporation | Vinyl acetate catalyst comprising palladium and gold deposited on a copper containing carrier |
| DE19734975A1 (de) * | 1997-08-13 | 1999-03-11 | Hoechst Ag | Schalenkatalysator, Verfahren zu dessen Herstellung sowie Verwendung, insbesondere zur Gasphasenoxidation von Ethylen und Essigsäure zu Vinylacetat |
| US5948724A (en) | 1997-10-28 | 1999-09-07 | Celanese International Corporation | Vinyl acetate catalyst comprising metallic palladium and gold and cupric acetate |
| US6072078A (en) * | 1997-12-12 | 2000-06-06 | Celanese International Corporation | Vinyl acetate production using a catalyst comprising palladium, gold, copper and any of certain fourth metals |
| GB9810928D0 (en) * | 1998-05-22 | 1998-07-22 | Bp Chem Int Ltd | Catalyst and process |
| US6017847A (en) * | 1998-06-02 | 2000-01-25 | Celanese International Corporation | Vinyl acetate catalyst prepared with potassium aurate and comprising metallic palladium and gold on a carrier precoated with copper |
| US6015769A (en) * | 1998-06-02 | 2000-01-18 | Celanese International Corporation | Vinyl acetate catalyst comprising metallic palladium, gold and copper supported on a carrier and prepared with potassium aurate |
| JP2000070718A (ja) * | 1998-06-17 | 2000-03-07 | Nippon Shokubai Co Ltd | ベンジルエステルの製造方法 |
| US6303537B1 (en) | 1999-11-17 | 2001-10-16 | Celanese International Corporation | Vinyl acetate catalyst comprising metallic palladium and gold and prepared utilizing sonication |
| CN1090997C (zh) * | 2000-04-30 | 2002-09-18 | 中国石油化工集团公司 | 一种选择加氢除炔多金属催化剂 |
| US20040242918A1 (en) * | 2000-06-27 | 2004-12-02 | Showa Denko K.K | Support and catalyst for use in producing lower aliphatic carboxylic acid ester, process for producing the catalyst and process for producing lower aliphatic carboxylic acid ester using the catalyst |
| US6534438B1 (en) * | 2000-07-26 | 2003-03-18 | Bp Chemicals Limited | Catalyst composition |
| DE10048844A1 (de) * | 2000-10-02 | 2002-04-11 | Basf Ag | Verfahren zur Herstellung von Platinmetall-Katalysatoren |
| US6576665B2 (en) | 2001-04-03 | 2003-06-10 | Braintree Laboratories, Inc. | Encapsulated calcium acetate caplet and a method for inhibiting gastrointestinal phosphorous absorption |
| TWI255736B (en) * | 2002-02-05 | 2006-06-01 | Basf Ag | A catalyst composition for the oxychlorination of ethylene and its use |
| DE10208254A1 (de) * | 2002-02-26 | 2003-09-04 | Bayer Ag | Katalysator |
| US6620965B1 (en) * | 2002-03-08 | 2003-09-16 | Catalytic Distillation Technologies | Process for vinyl acetate |
| JP5001543B2 (ja) * | 2004-11-17 | 2012-08-15 | 三菱レイヨン株式会社 | パラジウム含有担持触媒の製造方法 |
| US8563032B2 (en) | 2005-12-05 | 2013-10-22 | Roxane Laboratories, Inc. | Formulation and manufacturing process for calcium acetate capsules |
| MY148664A (en) * | 2006-08-30 | 2013-05-31 | Showa Denko Kk | Process for production of catalyst for alkenyl acetate production |
| US7825204B2 (en) * | 2006-12-19 | 2010-11-02 | Lyondell Chemical Technology, L.P. | Inorganic oxide extrudates |
| JP2008173629A (ja) * | 2006-12-20 | 2008-07-31 | Showa Denko Kk | アシルオキシ化反応用触媒およびその製造方法 |
| EP2177267B1 (en) * | 2007-08-13 | 2013-07-31 | Asahi Kasei Chemicals Corporation | Catalyst for carboxylic acid ester production, method for producing the same, and method for producing carboxylic acid ester |
| ES2805305T3 (es) * | 2007-10-26 | 2021-02-11 | Asahi Chemical Ind | Uso de un material de partículas compuestas soportadas, procedimiento de producción de dicho material y procedimiento para producir compuestos usando material de partículas compuestas soportadas como catalizador para síntesis química |
| JP2009220099A (ja) * | 2008-02-20 | 2009-10-01 | Showa Denko Kk | 低級脂肪族カルボン酸製造用触媒の製造方法 |
| US8173830B2 (en) * | 2009-05-07 | 2012-05-08 | Celanese International Corporation | Vinyl ester production from acetylene and carboxylic acid utilizing homogeneous catalyst |
| US20100310441A1 (en) * | 2009-06-05 | 2010-12-09 | Basf Corporation | Catalytic Article for Removal of Volatile Organic Compounds in Low Temperature Applications |
| GB201110850D0 (en) | 2011-03-04 | 2011-08-10 | Johnson Matthey Plc | Catalyst and mehtod of preparation |
| DE102012008715A1 (de) * | 2012-05-03 | 2013-11-07 | Clariant Produkte (Deutschland) Gmbh | Herstellung von Schalenkatalysatoren in einer Beschichtungsvorrichtung |
| DE102012008714A1 (de) * | 2012-05-03 | 2013-11-07 | Clariant Produkte (Deutschland) Gmbh | Vorimprägnierung von Schalenkatalysatoren mit einem Acetat |
| GB201210891D0 (en) * | 2012-06-19 | 2012-08-01 | Johnson Matthey Plc | Catalyst composition |
| TWI510293B (zh) * | 2012-09-19 | 2015-12-01 | Clariant Int Ltd | 用於製造烯基羧酸酯之銅促進殼催化劑，及用於製造該銅促進殼催化劑之方法。 |
| CN106582871B (zh) * | 2015-10-19 | 2020-07-03 | 中国石油化工股份有限公司 | 醋酸烯丙酯生产所用的催化剂 |
| US10596552B2 (en) * | 2017-06-21 | 2020-03-24 | China Petroleum & Chemical Corporation | Catalyst for preparing cumene and use thereof |
| WO2018235705A1 (ja) * | 2017-06-23 | 2018-12-27 | エヌ・イーケムキャット株式会社 | 酢酸ビニル合成用パラジウム－金担持触媒の製造方法 |
| US20210300848A1 (en) * | 2018-09-17 | 2021-09-30 | Sabic Global Technologies B.V. | Catalysts for producing alcohols and ethers from synthesis gas |
| KR102563207B1 (ko) | 2018-10-31 | 2023-08-02 | 에스케이이노베이션 주식회사 | 코발트계 단원자 탈수소화 촉매 및 이를 이용하여 파라핀으로부터 대응되는 올레핀을 제조하는 방법 |
| CN112642480B (zh) * | 2019-10-10 | 2022-12-09 | 中国石油化工股份有限公司 | 乙烯法醋酸乙烯催化剂 |
| KR102844575B1 (ko) * | 2019-11-20 | 2025-08-08 | 에스케이이노베이션 주식회사 | 탈수소화 성형 촉매 및 이를 이용하여 파라핀을 올레핀으로 전환시키는 방법 |
| CN110773163B (zh) * | 2019-12-02 | 2023-07-07 | 上海华谊（集团）公司 | 甲基丙烯醛选择加氢制甲基烯丙醇的催化剂及其制备方法 |
| PL3928864T3 (pl) | 2020-06-25 | 2025-03-31 | Sk Innovation Co., Ltd. | Sposób wytwarzania katalizatorów odwodornienia na bazie kobaltu w postaci pojedynczych atomów, mających ulepszoną stabilność termiczną, oraz sposób wytwarzania olefin z odpowiednich parafin |
| US12064750B2 (en) | 2020-09-17 | 2024-08-20 | Sk Innovation Co., Ltd. | Cobalt-based single-atom dehydrogenation catalysts having high selectivity and regenerability and method for producing corresponding olefins from paraffins using the same |
| EP4252905A4 (en) * | 2020-11-27 | 2024-10-23 | Resonac Corporation | PROCESS FOR MANUFACTURING CATALYST FOR MANUFACTURING VINYL ACETATE AND PROCESS FOR MANUFACTURING VINYL ACETATE |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3190912A (en) * | 1962-05-02 | 1965-06-22 | Nat Distillers Chem Corp | Process for preparing esters |
| BE638489A (enExample) * | 1962-10-11 | |||
| US3277159A (en) * | 1963-06-18 | 1966-10-04 | Union Oil Company Of America | Process for the production of unsaturated esters and acetals from olefins |
| GB1067850A (en) * | 1963-12-13 | 1967-05-03 | Ici Ltd | Improvements in and relating to the production of vinyl acetate |
| US3346624A (en) * | 1964-05-11 | 1967-10-10 | Union Oil Co | Process for the catalytic oxidation of olefins with a group viii noble metal catalyst and oxygen to aldehydes, acetals and unsaturated esters |
| US3531531A (en) * | 1965-06-23 | 1970-09-29 | Du Pont | Process for producing acetaldehyde from ethylene |
| DE1252662B (enExample) * | 1965-06-25 | |||
| US3373189A (en) * | 1965-07-09 | 1968-03-12 | Nat Distillers Chem Corp | Vapor phase process for producing vinyl acetate from ethylene |
| US3607916A (en) * | 1965-12-17 | 1971-09-21 | Asahi Chemical Ind | Process for producing vinyl acetate |
| NL6608559A (enExample) * | 1966-06-21 | 1967-12-22 | ||
| CH495319A (de) * | 1966-12-17 | 1970-08-31 | Bayer Ag | Verfahren zur Herstellung organischer Ester |
| DE1618589A1 (de) * | 1967-04-01 | 1971-02-25 | Knapsack Ag | Verfahren zur Herstellung von Carbonsaeuren |
| US4057575A (en) * | 1967-09-25 | 1977-11-08 | Union Oil Company Of California | Process for the preparation of unsaturated esters |
| US3579569A (en) * | 1967-10-06 | 1971-05-18 | Grace W R & Co | Preparation of vinyl acetate |
| US3471532A (en) * | 1967-10-09 | 1969-10-07 | Union Oil Co | Oxidation of olefins |
| US3650986A (en) * | 1967-12-23 | 1972-03-21 | Knapsack Ag | Carrier catalyst for the manufacture of unsaturated esters of carboxylic acids |
| CH534005A (de) * | 1968-02-01 | 1973-02-28 | Bayer Ag | Verfahren zur Herstellung eines Palladium und Gold enthaltenden Katalysators |
| DE1668114C3 (de) * | 1968-03-15 | 1974-12-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Vinylacetat |
| US3557192A (en) * | 1968-03-18 | 1971-01-19 | Grace W R & Co | Process for preparing unsaturated esters |
| GB1283737A (en) * | 1968-09-04 | 1972-08-02 | Nat Distillers Chem Corp | Method of catalyst preparation |
| FR1596449A (enExample) * | 1968-10-12 | 1970-06-15 | ||
| US3622620A (en) * | 1969-10-27 | 1971-11-23 | Denki Kagaku Kogyo Kk | Method of making vinyl acetate |
| US3939199A (en) * | 1971-01-06 | 1976-02-17 | Hoechst Aktiengesellschaft | Oxacylation of olefins in the gaseous phase |
| US3758551A (en) * | 1971-11-10 | 1973-09-11 | Nat Distillers Chem Corp | Process for the preparation of acrylate and methacrylate esters |
| US3970697A (en) * | 1974-07-01 | 1976-07-20 | National Distillers And Chemical Corporation | Oxidation of ethylene to acetic acid |
| JPS5136413A (en) * | 1974-09-10 | 1976-03-27 | Kuraray Co | Fuhowaesuteru no seizoho |
| US4133962A (en) * | 1975-02-14 | 1979-01-09 | Hoechst Aktiengesellschaft | Process for the preparation of carboxylic acid alkenyl esters |
| GB1571910A (en) * | 1975-12-18 | 1980-07-23 | Nat Distillers Chem Corp | Vinyl acetate process and catalyst therefor |
| DE2601154A1 (de) * | 1976-01-14 | 1977-07-21 | Bayer Ag | Neuer katalysator, seine herstellung und verwendung |
| US4048096A (en) * | 1976-04-12 | 1977-09-13 | E. I. Du Pont De Nemours And Company | Surface impregnated catalyst |
| DE2811211A1 (de) * | 1978-03-15 | 1979-09-27 | Hoechst Ag | Traeger-katalysator fuer die herstellung von ungesaettigten estern aus olefinen (c tief 3 -c tief 10 ), carbonsaeuren und sauerstoff in der gasphase |
| FR2523149A1 (fr) * | 1982-03-15 | 1983-09-16 | Catalyse Soc Prod Francais | Nouveau catalyseur supporte palladium-or, sa preparation et son utilisation dans les reactions d'hydrogenation selective d'hydrocarbures diolefiniques et/ou acetyleniques |
| DE3803900A1 (de) * | 1988-02-09 | 1989-08-17 | Hoechst Ag | Verfahren zur herstellung von vinylacetat |
| US5194417A (en) * | 1991-12-05 | 1993-03-16 | Quantum Chemical Corporation | Pretreatment of palladium-gold catalysts useful in vinyl acetate synthesis |
-
1993
- 1993-05-25 US US08/067,445 patent/US5347046A/en not_active Expired - Lifetime
-
1994
- 1994-05-11 CA CA002161952A patent/CA2161952A1/en not_active Abandoned
- 1994-05-11 JP JP50072295A patent/JP3698322B2/ja not_active Expired - Lifetime
- 1994-05-11 BR BR9406696A patent/BR9406696A/pt not_active Application Discontinuation
- 1994-05-11 WO PCT/US1994/005382 patent/WO1994027720A1/en not_active Ceased
- 1994-05-11 CN CN94192124A patent/CN1123527A/zh active Pending
- 1994-05-11 AU AU69129/94A patent/AU6912994A/en not_active Abandoned
- 1994-05-11 EP EP94917387A patent/EP0708684A1/en not_active Withdrawn
- 1994-05-12 TW TW083104285A patent/TW254934B/zh active
-
1995
- 1995-11-24 KR KR1019950705255A patent/KR960702348A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU6912994A (en) | 1994-12-20 |
| JP3698322B2 (ja) | 2005-09-21 |
| CN1123527A (zh) | 1996-05-29 |
| EP0708684A1 (en) | 1996-05-01 |
| JPH08510685A (ja) | 1996-11-12 |
| TW254934B (enExample) | 1995-08-21 |
| BR9406696A (pt) | 1996-03-19 |
| US5347046A (en) | 1994-09-13 |
| KR960702348A (ko) | 1996-04-27 |
| WO1994027720A1 (en) | 1994-12-08 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |