EP2512654A1 - Herstellung eines palladium-gold-katalysators - Google Patents
Herstellung eines palladium-gold-katalysatorsInfo
- Publication number
- EP2512654A1 EP2512654A1 EP10779908A EP10779908A EP2512654A1 EP 2512654 A1 EP2512654 A1 EP 2512654A1 EP 10779908 A EP10779908 A EP 10779908A EP 10779908 A EP10779908 A EP 10779908A EP 2512654 A1 EP2512654 A1 EP 2512654A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- extrudate
- palladium
- cellulose
- titania
- produce
- 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.)
- Ceased
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 47
- 229910052737 gold Inorganic materials 0.000 title claims abstract description 37
- 239000010931 gold Substances 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 76
- 229920002678 cellulose Polymers 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 44
- 239000001913 cellulose Substances 0.000 claims abstract description 42
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000001301 oxygen Substances 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000001354 calcination Methods 0.000 claims abstract description 19
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000005977 Ethylene Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 23
- -1 methyl 2-hydroxypropyl Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002344 gold compounds Chemical class 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 150000002941 palladium compounds Chemical class 0.000 claims description 7
- 239000012190 activator Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 abstract description 13
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 abstract description 11
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract description 4
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 235000010980 cellulose Nutrition 0.000 description 33
- 235000010215 titanium dioxide Nutrition 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000001307 helium Substances 0.000 description 5
- 229910052734 helium Inorganic materials 0.000 description 5
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 238000006137 acetoxylation reaction Methods 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000010981 drying operation Methods 0.000 description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000011800 void material Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 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
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JTWZVKMWOCBJEV-KLLFFGQPSA-N ethane-1,2-diol (2S,3R,4R,5S,6R)-2-(hydroxymethyl)-6-[(2S,3R,4S,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol (2S,3S,4R,5S,6S)-2,3,4-trimethoxy-6-(methoxymethyl)-5-[(2R,3S,4R,5S,6S)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxyoxane Chemical compound OCCO.OC[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](O)O[C@H]2CO)[C@@H](O)[C@H](O)[C@H]1O.COC[C@@H]1O[C@H](O[C@H]2[C@H](COC)O[C@H](OC)[C@@H](OC)[C@@H]2OC)[C@@H](OC)[C@H](OC)[C@H]1OC JTWZVKMWOCBJEV-KLLFFGQPSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- BBKFSSMUWOMYPI-UHFFFAOYSA-N gold palladium Chemical compound [Pd].[Au] BBKFSSMUWOMYPI-UHFFFAOYSA-N 0.000 description 1
- RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940080262 sodium tetrachloroaurate Drugs 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B30/00—Compositions for artificial stone, not containing binders
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; Oxides or hydroxides thereof
-
- 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
- B01J23/54—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
- B01J23/66—Silver or 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
-
- 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
- B01J6/00—Heat treatments such as Calcining; Fusing ; Pyrolysis
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/38—Polysaccharides or derivatives thereof
- C04B24/383—Cellulose or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
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Definitions
- the invention relates to a method of preparing a palladium-gold catalyst containing a titania extrudate.
- Palladium-gold catalysts are useful in the oxidation of ethylene or propylene in the presence of acetic acid to produce vinyl acetate or allyl acetate. Acetoxylation is commonly conducted in the vapor phase using a supported palladium-gold catalyst. Palladium-gold catalysts containing titania carriers are known (U.S. Pat. No. 6,022,823; U.S. Pat. Appl. Pub. Nos. 2008/0146721 and 2008/0281 122; copending application serial number 1 1/801 ,935 filed May 1 1 , 2007). Acetoxylation is preferably conducted in a fixed-bed reactor.
- titania is produced as a fine powder. To prepare catalysts suitable for fixed-bed reactions, it is necessary to form titania powder into particles, such as spheres, tablets, extrudates, and the like. Despite many efforts in developing methods for producing titania extrudates in the past, many are not suitable for commercial production because of their poor processibility. Therefore, there is a continued need to develop new processes for making titania extrudates that can be used as carriers for palladium-gold catalysts (see, e.g., co-pending application Docket No. 01-2767A [serial number has not yet been assigned] filed on December 16, 2009).
- the invention is a method for preparing a palladium-gold catalyst.
- the method comprises (a) mixing titania, a carboxyalkyl cellulose, and a hydroxyalkyl cellulose to form a dough; (b) extruding the dough to produce an extrudate; (c) calcining the extrudate to produce a calcined extrudate; (d) impregnating the calcined extrudate with a palladium compound and a gold compound to produce an impregnated extrudate; and (e) calcining the impregnated extrudate to produce the palladium-gold catalyst.
- the invention also includes a process for producing vinyl
- I acetate comprising reacting ethylene, oxygen, and acetic acid in the presence of a palladium-gold catalyst.
- the invention is a method for preparing a palladium-gold catalyst containing a titania carrier.
- the method comprises mixing titania, a carboxyalkyi cellulose, and a hydroxyalkyl cellulose to form a dough.
- Suitable titanias can be rutile, anatase, brookite, or a mixture of them.
- the titania is an anatase.
- Titanias may be produced by the chloride process, the sulfate process, the hydrothermal process, or the flame hydrolysis of titanium tetrachloride.
- suitable titanias include TiONA® DT-51 , DT-52, DT-51 D, DT-40, and DT-20 of Millennium Inorganic Chemicals.
- the functional properties of carboxyalkyi celluloses depend on the degree of substitution of the cellulose structure (i.e., how many of the hydroxy! groups are substituted), as well as the chain length of the cellulose backbone and the degree of clustering of the substituents.
- the average number of substituted hydroxyl groups per glucose unit in cellulose derivatives is referred to as the degree of substitution (DS).
- DS degree of substitution
- a carboxymethyl celluloses is used.
- Preferred carboxymethyl celluloses have a degree of substitution of 0.5 to 0.9 (D. B. Braun and M. R. Rosen, Rheoloav Modifiers Handbook: Practical Use and Applications (2000) William Andrew Publishing, pp. 109-131 ).
- Carboxymethyl celluloses are known as extrusion aids (U.S. Pat. Nos. 5,884,138 and 6,709,570; U.S. Pat. Appl. Pub. No. 2008/0146721 ).
- Carboxyalkyl cellulose, R H, alkyl
- the method also uses a hydroxyalkyl cellulose.
- a hydroxyalkyl cellulose is a derivative of cellulose in which some of the hydroxyl groups in the repeating glucose units are hydroxyalkylated. Some of the hydroxyl groups in a hydroxyalkyl cellulose may also be alkylated.
- the hydroxyalkyl group is selected from the group consisting of 2- hydroxyethyl, 2-hydroxypropyl, and mixtures thereof. More preferably the hydroxyalkyl cellulose is alkylated. Most preferably, the hydroxyalkyl cellulose is selected from the group consisting of methyl 2-hydroxyethyl cellulose, methyl 2- hydroxypropyl cellulose, and mixtures thereof. Preferably, the degree of methyl substitution is from 1 to 2, more preferably from 1.5 to 1.8; and the 2-hydroxyethyl or 2-hydroxypropyl molar substitution is from 0.1 to 0.3.
- METHOCELTM K4M cellulose derivative a product of Dow Chemical Company and having a methyl substitution of 1.4 and a hydroxypropyl molar substitution of 0.21 , is preferably used.
- Hydroxyalkyi celluloses are known as extrusion aids (U.S. Pat. Nos. 5,884,138, 6,316,383, and 6,709,570).
- the weight ratio of the carboxyalkyi cellulose to the titania is preferably from
- the weight ratio of the hydroxyalkyi cellulose to the titania is preferably from 0.1 :100 to 2.5:100, more preferably from 0.2:100 to 2:100, most preferably from 0.5:100 to 1 :100.
- the weight ratio of the carboxyalkyi cellulose to the hydroxyalkyi cellulose is preferably from 5:1 to 1 :2, more preferably from 3:1 to 1 :1.
- the method comprises mixing titania, the carboxyalkyi cellulose, and the hydroxyalkyi cellulose to form a dough.
- a solvent may be used. Suitable solvents include water, alcohols, ethers, esters, amides, aromatic compounds, halogenated compounds, and the like, and mixtures thereof. Preferred solvents are water and alcohols.
- a titania sol may be used as a source of the titania.
- a titania sol is a colloidal suspension of titania particles in a liquid.
- a titania sol can be prepared by hydrolyzing a titania precursor. Suitable titania precursors include titanium salts, titanium halides, titanium alkoxides, titanium oxyhalides, and the like.
- the method comprises extruding the dough to produce an extrudate by an operation called extrusion.
- Extrusion is a process in which a dough is pushed through a die or an orifice to create long objects of a fixed cross-section. Extrusion is commonly used to process plastics or food, and to form adsorbents, catalysts, or catalyst carriers. Any conventional extruder may be used. A suitable screw-type extruder is described in "Particle Size Enlargement," Handbook of Powder Technology, vol. 1 (1980) pp. 112-22.
- the carboxyalkyi cellulose and the hydroxyalkyi cellulose are used as extrusion aids.
- An extrusion aid helps the mixing, mulling, and extruding operation and may improve the mechanical and/or physical properties of the extrudate such as crushing strength, surface area, pore size, or pore volume.
- the extrudate comprising titania, the carboxyalkyi cellulose and the hydroxyalkyi cellulose has a smooth outer surface. They do not tend to stick to each other while being formed, dried, and calcined, which is suitable for large scale production.
- extrusion aids may be used to form the dough.
- suitable extrusion aids include alkyl amines, carboxylic acids, alkyl ammonium compounds, amino alcohols, starch, polyacrylates, polymethacrylates, poly( vinyl alcohol)s, poly(vinylpyrrolidone)s, po!y(amino acid)s, polyethers, poly(tetrahydrofuran)s, metal carboxylates, and the like, and mixtures thereof.
- Preferred poly(alkylene oxide)s are poly(ethylene oxide)s, poly( ropylene oxide)s, or copolymers of ethylene oxide and propylene oxide.
- Organic extrusion aids are usually removed by calcination.
- the extrudate is optionally dried after it is formed.
- the drying operation removes at least a portion of the solvents from the extrudate.
- the drying operation may be performed at 30 to 200°C at atmospheric pressure or under vacuum.
- the drying may occur in air or an inert atmosphere. Sometimes, it is preferable to raise the drying temperature slowly so the extrudate will not be cracked or weakened.
- the method comprises calcining the extrudate to produce a calcined extrudate.
- the calcination is carried out in an oxygen-containing gas to burn off the organic materials (e.g., residual solvent and extrusion aids) contained in the extrudate.
- the calcination may be carried out at 400 to 1000°C, more preferably from 450 to 800°C, most preferably from 650 to 750°C.
- a calcined extrudate after the calcination contains less than 0.5 wt% carbon. Preferably, it contains less than 0.1 wt% carbon.
- the method comprises impregnating the calcined extrudate with a palladium compound and a gold compound to produce an impregnated extrudate.
- Suitable palladium compounds include palladium chloride, sodium chloropalladate, palladium nitrate, palladium sulfate, the like, and mixtures thereof.
- Suitable gold compounds include auric chloride, tetrachloroauric acid, sodium tetrachloroaurate, the like, and mixtures thereof.
- the impregnated extrudate may comprise from 0.1 wt% to 3 wt% of palladium and from 0.1 wt% to 3 wt% of gold and has a weight ratio of palladium to gold within the range of 5:1 to 1 :3. More preferably, the impregnated extrudate comprises 0.5 wt% to 1.5 wt% of palladium and 0.25 wt% to 0.75 wt% of gold.
- a fixing agent may preferably be added to the extrudate while it is being impregnated. Fixing agents help to bind the palladium compound and the gold compound to the extrudate. Suitable fixing agents include alkali metal, alkaline earth metal, or ammonium compounds, for example, their hydroxides, carbonates, bicarbonates, metasilicates, and the like, and mixtures thereof.
- the impregnation method can be used to produce the impregnated extrudate.
- the calcined extrudate may be simultaneously or successively impregnated with the palladium compound, the gold compound, and optionally a fixing agent.
- it is impregnated with aqueous solutions although other impregnating solvents may be used.
- the impregnated extrudate is preferably washed with water or other solvents to remove any halide (e.g., chloride) from the extrudate.
- halide e.g., chloride
- the method optionally comprises drying the impregnated extrudate.
- the impregnated extrudate can be dried at 50 to 150°C at atmospheric pressure or under vacuum, primarily to remove at least a portion of the solvents.
- the drying may occur in air or an inert gas at atmospheric pressure or under vaccum. Sometimes, it is important to raise the drying temperature slowly to prevent the extrudate from losing its mechanical strength.
- the method comprises calcining the impregnated extrudate, preferably after it is dried first, to produce the palladium-gold catalyst.
- the calcination of the impregnated extrudate occurs at an elevated temperature in a non-reducing atmosphere.
- the calcination of the impregnated extrudate is carried out at a temperature of 150 to 600°C.
- Suitable non-reducing gases used for the calcination include inert or oxidizing gases such as helium, nitrogen, argon, neon, oxygen, air, carbon dioxide, the like, and mixtures thereof.
- the calcination is carried out in an atmosphere of nitrogen, oxygen, or air, or mixtures thereof.
- the palladium-gold catalyst obtained from the calcination step is preferably chemically reduced to generate a reduced palladium-gold catalyst.
- the reduction is usually performed by contacting the palladium-gold catalyst with a reducing agent.
- Suitable reducing agents include hydrogen, carbon monoxide, hydrocarbons, olefins, aldehydes, alcohols, hydrazine, the like, and mixtures thereof. Hydrogen, ethylene, propylene, alkaline hydrazine and alkaline formaldehyde are preferred reducing agents and ethylene and hydrogen are particularly preferred.
- Temperatures employed for the reduction can range from 20 to 700°C.
- hydrogen is the reducing agent
- a gas mixture containing hydrogen and another gas such as argon, helium, nitrogen, or the like, is usually used.
- the reduction temperature with hydrogen is preferably in the range of 300 to 700°C, more preferably in the range of 450 to 550°C.
- the pailadium-gold catalyst prepared according to the invention can be used for the acetoxylation of an olefin, such as ethylene or propylene, to produce an acetoxylated olefin such as vinyl acetate or allyl acetate.
- a promoted palladium-gold catalyst which can be produced by adding an activator to the reduced palladium-gold catalyst, is used in the acetoxylation reaction.
- An activator is an alkali or alkaline earth metal compound, examples of which are hydroxides, acetates, nitrates, carbonates, and bicarbonates of potassium, sodium, cesium, magnesium, barium, and the like. Potassium salts are preferred activators.
- the activator content may be in the range of 0 to 15 wt%, preferably 1.5 to 10 wt% of the catalyst.
- the invention also include a process for preparing vinyl acetate, comprising reacting a feed comprising ethylene, oxygen, and acetic acid in the presence of the palladium-gold catalyst, preferably in the presence of the reduced palladium-gold catalyst, more preferably in the presence of the promoted palladium-gold catalyst.
- the feed typically comprise 20 to 70 mol% ethylene, 2 to 8 mol% oxygen, and 2 to 20 mol% acetic acid.
- the feed may comprise a diluent.
- suitable diluents inciude propane, nitrogen, helium, argon, carbon dioxide, the like, and mixtures thereof.
- the reaction is generally performed at a temperature in the range of 100 to 250°C, preferably 125 to 200°C and under a pressure of 15 to 500 psig.
- the dough produced is placed in the hopper of a Bonnot 2-inch extruder (The Bonnot Company) equipped with a die face of 25 holes with a diameter of 1/8 inch.
- the extrusion is performed at a rate of approximately 0.25 kg/mi n.
- the extrudates produced have smooth outer surface and there is minimal sticking each other occuring. Almost no feathering is observed.
- the extrudates are piled 1 inch deep on a collection tray and dried in air at
- the calcination temperature is raised from room temperature to 500°C at a rate of 2°C/min, held at 500°C for 2 h, raised from 500°C to 700°C at a rate of 10°C/min, held at 700°C for 3 h, then lowered to room temperature.
- the crush strength of the calcined titania extrudate is measured with a Chatillon crush strength analyzer (Model DPP 50). The force necessary for failure in 25 measurements is averaged to give the reported value.
- Bulk density is measured by placing 40 g of the calcined extrudates in a 100-mL graduated cylinder ( ⁇ nominal outer diameter). The graduated cylinder is tapped until the apparent volume no longer changes, and then this value is divided into the mass to calculate the bulk density.
- Void age is determined by adding the pellets to 50 mL water in a second graduated cylinder and then tapping until all voids are filled. The resulting water level is subtracted from the total volume of the water and the pellets taken separately to determine the void volume occupied by water.
- Total pore volume is determined by pouring the mixture through a sieve basket, shaking to remove excess water and then weighing the wet extrudates. The increase in mass over the initial 40 g of extrudates divided by the density of water is taken as the measure of the pore volume.
- Example 2 The procedure of Example 1 is repeated with the formulation shown in Table 1. The extrudates are droopy as they exit the die face of the extruder and tend to stick to each other as they lay on the collection tray. COMPARATIVE EXAMPLE 3
- Example 1 The procedure of Example 1 is repeated with the formulation shown in Table 1.
- the extrudates are droopy as they exit the die face of the extruder and tend to stick to each other as they lay on the collection tray.
- Example 2 The procedure of Example 1 is repeated, except that the formulation is as follows: DT-51 (2000 g), TAMOLTM 1124 dispersant (a hydrophilic polyelectrolyte copolymer from The Dow Chemical Company, 32.6 g), METHOCELTM K4M cellulose derivative (54.6 g), lactic acid (6 g), water (950 g), aqueous ammonium hydroxide (14.8 M, 70 g).
- TAMOLTM 1124 dispersant a hydrophilic polyelectrolyte copolymer from The Dow Chemical Company, 32.6 g
- METHOCELTM K4M cellulose derivative 54.6 g
- lactic acid (6 g)
- water 950 g
- aqueous ammonium hydroxide 14.8 M, 70 g
- Example 4 The procedure of Example 4 is repeated, except that alumina (DISPERAL® P2, available from Sasol, 20 g) is used.
- alumina DISPERAL® P2, available from Sasol, 20 g
- the extrudates are droopy as they exit the die face of the extruder and tend to stick to each other as they lay on a metal tray.
- the calcined extrudate contains 1 wt% alumina and 99 wt% titania. Table 2
- Example 1 The procedure of Example 1 is repeated, except that the formulation is as follows: DT51 (300 g), TAMOLTM 1 124 dispersant (5 g), WALOCELTM C cellulose (6 g), METHOCELTM K4M cellulose derivative (6 g), lactic acid (4.5 g), water (155 g), and aqueous ammonium hydroxide (14.8 M, 11 g).
- the extrudates have smooth outer surface. Minimal feathering is observed. Almost no extrudate is observed to stick to others.
- Example 6 The procedure of Example 6 is repeated, except that the formulation is shown in Table 3. The extrudates slump upon exiting the die. They stick to each other on the collection tray.
- Example 6 The procedure of Example 6 is repeated, except that the formulation is shown in Table 3.
- the extrudates do not tend to stick to each other after laying the on the collection tray. However, they appear to be feathering. Table 3
- NaHCOa powder (27 g) is slowly added to an aqueous solution containing Na 2 PdCV3H 2 0 (31.4 g), NaAuCI 4 '2H 2 0 (11.3 g), and water (235.4 g). The mixture is stirred at room temperature for 10 min. The solution is sprayed with a pipette on calcined titania extrudates prepared in Example 1 (1000 g) while they are being tumbled in a rotating flask. Once the impregnation is finished, the rotating flask is heated to about 100°C with a heat gun. The impregnated extrudates are tumbled for another 30 min at 100°C, then placed in an oven at 80°C for 2 h before they are cooled to room temperature.
- the dried extrudates are washed with warm water (50-80°C) until no chloride can be detected by mixing the wash filtrate solution with a 1 wt% silver nitrate solution to observe precipitation.
- the catalyst is dried at 80 to 100°C to remove water. Then they are heated at 230°C for 3 h in air, and at 230°C for 30 min under a nitrogen flow. The temperature is raised to 500°C under a flow of 10 mol% hydrogen in nitrogen gas, and held for 3 h before it is cooled to room temperature.
- the extrudates are washed with an aqueous solution containing 10 wt% potassium acetate and 1 wt% potassium hydroxide (10 L).
- the washed extrudates are dried under nitrogen at 125°C for 2 h.
- a palladium-gold catalyst is obtained. It contains 0.93 wt% Pd, 0.54 wt% Au, and 1.5 wt% K.
- the palladium-gold catalyst prepared in Example 9 is tested for vinyl acetate production in a fixed-bed reactor (stainless steel, 1 inch O.D.).
- the reactor is charged with a mixture of the catalyst (10 g) and an inert alpha alumina cylindrical pellets (1/8" in diameter, surface area 4 m 2 /g, pore volume 0.25 mUg, 25 g).
- the feed contains 46.1 mol% helium, 33.9 mo!% ethylene, 11.48 mol% acetic acid, 4.2 mol% oxygen, and 4.2 mol% nitrogen.
- the reactor pressure is 80 psig and the space velocity relative to the volume of the catalyst is 3050 h "1 at standard temperature and pressure.
- the reactor is cooled using a fluidized sand bath, the temperature of which is set at 130°C.
- the product stream is analyzed by gas chromatography (GC).
- Oxygen conversion, oxygen selectivity, oxygen yield to vinyl acetate, and ethylene selectivity to vinyl acetate between 75 to 100 h on stream are calculated from the GC results and listed in Table 4.
- Oxygen conversion is calculated by dividing the amount of oxygen consumed by the total amount of oxygen fed to the reactor.
- Oxygen selectivity to vinyl acetate is the amount of oxygen consumed in making vinyl acetate divided by the total amount of oxygen consumed.
- Oxygen yield to vinyl acetate is the product of oxygen conversion multiplied by oxygen selectivity.
- Ethylene selectivity to vinyl acetate is the amount of ethylene consumed in making vinyl acetate divided by the total amount of ethylene consumed.
- Catalyst productivity is the grams of vinyl acetate produced per liter of the catalyst per hour.
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US12/653,592 US8273682B2 (en) | 2009-12-16 | 2009-12-16 | Preparation of palladium-gold catalyst |
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US8273682B2 (en) | 2009-12-16 | 2012-09-25 | Lyondell Chemical Technology, L.P. | Preparation of palladium-gold catalyst |
US8329611B2 (en) | 2009-12-16 | 2012-12-11 | Lyondell Chemical Technology, L,P. | Titania-containing extrudate |
US8507720B2 (en) | 2010-01-29 | 2013-08-13 | Lyondell Chemical Technology, L.P. | Titania-alumina supported palladium catalyst |
JP2013514175A (ja) * | 2009-12-16 | 2013-04-25 | ライオンデル ケミカル テクノロジー、 エル.ピー. | パラジウム−金触媒の調製 |
EP2703078A1 (de) * | 2012-09-03 | 2014-03-05 | Saudi Basic Industries Corporation | Photokatalysator enthaltend Gold-Palladium-Legierung, Verfahren zu dessen Herstellung und Photolysesystem |
US20140081040A1 (en) * | 2012-09-20 | 2014-03-20 | Lyondell Chemical Technology, L.P. | Process for pre-treatment of a catalyst support and catalyst prepared therefrom |
KR101964275B1 (ko) | 2015-09-01 | 2019-04-01 | 주식회사 엘지화학 | 아크릴산 제조용 촉매 제조방법 및 이로부터 제조되는 촉매 |
WO2019122075A1 (en) * | 2017-12-20 | 2019-06-27 | Basf Se | Catalyst and process for preparing dimethyl ether |
CN112517065B (zh) * | 2019-09-18 | 2023-05-02 | 中国石油化工股份有限公司 | 乙烯气相法醋酸乙烯工艺催化剂制备方法 |
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US4551295A (en) * | 1984-04-26 | 1985-11-05 | Corning Glass Works | Process for mixing and extruding ceramic materials |
DE4012479A1 (de) * | 1990-04-19 | 1991-10-24 | Degussa | Titandioxidpresslinge, verfahren zu ihrer herstellung sowie ihre verwendung |
US5582670A (en) * | 1992-08-11 | 1996-12-10 | E. Khashoggi Industries | Methods for the manufacture of sheets having a highly inorganically filled organic polymer matrix |
GB9305066D0 (en) * | 1993-03-12 | 1993-04-28 | British American Tobacco Co | Improvements relating to filtration materials |
JP3833731B2 (ja) * | 1995-01-20 | 2006-10-18 | 触媒化成工業株式会社 | アンモニアの分解方法 |
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US6022823A (en) | 1995-11-07 | 2000-02-08 | Millennium Petrochemicals, Inc. | Process for the production of supported palladium-gold catalysts |
US5884138A (en) | 1996-06-10 | 1999-03-16 | Corning Incorporated | Method for improving the stiffness of extrudates |
JP3636912B2 (ja) * | 1997-12-25 | 2005-04-06 | 株式会社日本触媒 | エチレンオキシド製造用触媒の製造方法 |
DE19828491A1 (de) | 1998-06-26 | 1999-12-30 | Degussa | Formkörper auf Basis von Siliciumdioxid |
US6709570B1 (en) | 1999-09-27 | 2004-03-23 | Shell Oil Company | Method for preparing a catalyst |
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DE10163180A1 (de) * | 2001-12-21 | 2003-07-10 | Degussa | Trägerkatalysator |
US6677261B1 (en) * | 2002-07-31 | 2004-01-13 | Corning Incorporated | Alumina-bound high strength ceramic honeycombs |
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US8168562B2 (en) * | 2006-02-02 | 2012-05-01 | Lyondell Chemical Technology, L.P. | Preparation of palladium-gold catalysts |
DE102006022866A1 (de) * | 2006-05-16 | 2007-11-22 | Glatt Systemtechnik Gmbh | Kohlenstoff-Granulat, Verfahren zu dessen Herstellung und dessen Verwendung |
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