DE102004061016A1 - Halogenidhaltige Alkaliwolframate enthaltende Katalysatoren zur Synthese von Alkylmercaptan und Verfahren zu ihrer Herstellung - Google Patents
Halogenidhaltige Alkaliwolframate enthaltende Katalysatoren zur Synthese von Alkylmercaptan und Verfahren zu ihrer Herstellung Download PDFInfo
- Publication number
- DE102004061016A1 DE102004061016A1 DE102004061016A DE102004061016A DE102004061016A1 DE 102004061016 A1 DE102004061016 A1 DE 102004061016A1 DE 102004061016 A DE102004061016 A DE 102004061016A DE 102004061016 A DE102004061016 A DE 102004061016A DE 102004061016 A1 DE102004061016 A1 DE 102004061016A1
- Authority
- DE
- Germany
- Prior art keywords
- halide
- tungstate
- alkali
- catalyst according
- catalyst
- 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.)
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- 239000003054 catalyst Substances 0.000 title claims abstract description 76
- 150000004820 halides Chemical class 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000008569 process Effects 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000001340 alkali metals Chemical class 0.000 title claims description 37
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 32
- 230000015572 biosynthetic process Effects 0.000 title abstract description 11
- 238000003786 synthesis reaction Methods 0.000 title abstract description 10
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000003513 alkali Substances 0.000 claims abstract description 30
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 13
- -1 alkyl mercaptans Chemical class 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 238000005470 impregnation Methods 0.000 claims description 31
- 229910052792 caesium Inorganic materials 0.000 claims description 27
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 26
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 12
- 229910052721 tungsten Inorganic materials 0.000 claims description 12
- 239000010937 tungsten Substances 0.000 claims description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- 239000012876 carrier material Substances 0.000 claims description 11
- 229910052701 rubidium Inorganic materials 0.000 claims description 11
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000011591 potassium Substances 0.000 claims description 8
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 238000001354 calcination Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000012018 catalyst precursor Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002484 inorganic compounds Chemical class 0.000 claims description 2
- 229910010272 inorganic material Inorganic materials 0.000 claims description 2
- 150000003658 tungsten compounds Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000006835 compression Effects 0.000 claims 1
- 238000007906 compression Methods 0.000 claims 1
- 238000001125 extrusion Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000011521 glass Substances 0.000 description 15
- 230000000694 effects Effects 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 9
- 238000000465 moulding Methods 0.000 description 9
- 239000008187 granular material Substances 0.000 description 8
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 description 6
- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000013022 venting Methods 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 239000013543 active substance Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000001663 caesium Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/08—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by replacement of hydroxy groups or etherified or esterified hydroxy groups
-
- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/30—Tungsten
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/132—Halogens; Compounds thereof with chromium, molybdenum, tungsten or polonium
-
- 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
-
- 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
- B01J37/0215—Coating
-
- 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
- B01J37/0215—Coating
- B01J37/0221—Coating of particles
-
- 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
- B01J37/024—Multiple impregnation or coating
- B01J37/0248—Coatings comprising impregnated particles
-
- 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
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/396—Distribution of the active metal ingredient
- B01J35/397—Egg shell like
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/633—Pore volume less than 0.5 ml/g
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/635—0.5-1.0 ml/g
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/638—Pore volume more than 1.0 ml/g
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004061016A DE102004061016A1 (de) | 2004-12-18 | 2004-12-18 | Halogenidhaltige Alkaliwolframate enthaltende Katalysatoren zur Synthese von Alkylmercaptan und Verfahren zu ihrer Herstellung |
| EP05813888A EP1824595B1 (de) | 2004-12-18 | 2005-11-24 | Halogenidhaltige caesiumwolframate enthaltende katalysatoren zur synthese von alkylmercaptan und verfahren zu ihrer herstellung |
| CN2005800433717A CN101080272B (zh) | 2004-12-18 | 2005-11-24 | 包括含卤化物碱金属钨酸盐的用于合成烷基硫醇的催化剂及其制备方法 |
| BRPI0515792-7A BRPI0515792A (pt) | 2004-12-18 | 2005-11-24 | catalisadores compreendendo tungstatos alcalinos contendo haleto e processos para a preparação de um catalisador de suporte e de alquilmercaptanos |
| DE502005010114T DE502005010114D1 (de) | 2004-12-18 | 2005-11-24 | Halogenidhaltige caesiumwolframate enthaltende katalysatoren zur synthese von alkylmercaptan und verfahren zu ihrer herstellung |
| ES05813888T ES2351195T3 (es) | 2004-12-18 | 2005-11-24 | Catalizadores que comprenden wolframatos de cesio que contienen halogenuros para la síntesis de alquil-mercaptanos, y proceso para producción de los mismos. |
| PCT/EP2005/012598 WO2006063669A1 (de) | 2004-12-18 | 2005-11-24 | Halogenidhaltige alkaliwolframate enthaltende katalysatoren zur synthese von alkylmercaptan und verfahren zu ihrer herstellung |
| CA002591037A CA2591037A1 (en) | 2004-12-18 | 2005-11-24 | Catalysts comprising halide-containing alkali tungstates for synthesizing alkyl mercaptane, and method for the production thereof |
| AT05813888T ATE477848T1 (de) | 2004-12-18 | 2005-11-24 | Halogenidhaltige caesiumwolframate enthaltende katalysatoren zur synthese von alkylmercaptan und verfahren zu ihrer herstellung |
| MX2007007169A MX2007007169A (es) | 2004-12-18 | 2005-11-24 | Catalizadores que comprenden tungstatos alcali que contienen haluro para sinterizar alquilmercaptanos, y metodo para la produccion de los mismos. |
| JP2007545867A JP5026985B2 (ja) | 2004-12-18 | 2005-11-24 | アルキルメルカプタンを合成するためのハロゲン化物含有のアルカリ金属タングステン酸塩を含む触媒及びその製造方法 |
| RU2007127217/04A RU2384364C2 (ru) | 2004-12-18 | 2005-11-24 | Катализаторы, которые содержат галогенидсодержащие вольфраматы щелочных металлов, для синтеза алкилмеркаптанов и способ их приготовления |
| US11/304,438 US8022254B2 (en) | 2004-12-18 | 2005-12-15 | Catalysts comprising halide-containing alkali tungstates for the synthesis of alkylmercaptan, and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004061016A DE102004061016A1 (de) | 2004-12-18 | 2004-12-18 | Halogenidhaltige Alkaliwolframate enthaltende Katalysatoren zur Synthese von Alkylmercaptan und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004061016A1 true DE102004061016A1 (de) | 2006-06-22 |
Family
ID=35822630
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004061016A Withdrawn DE102004061016A1 (de) | 2004-12-18 | 2004-12-18 | Halogenidhaltige Alkaliwolframate enthaltende Katalysatoren zur Synthese von Alkylmercaptan und Verfahren zu ihrer Herstellung |
| DE502005010114T Expired - Lifetime DE502005010114D1 (de) | 2004-12-18 | 2005-11-24 | Halogenidhaltige caesiumwolframate enthaltende katalysatoren zur synthese von alkylmercaptan und verfahren zu ihrer herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502005010114T Expired - Lifetime DE502005010114D1 (de) | 2004-12-18 | 2005-11-24 | Halogenidhaltige caesiumwolframate enthaltende katalysatoren zur synthese von alkylmercaptan und verfahren zu ihrer herstellung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8022254B2 (https=) |
| EP (1) | EP1824595B1 (https=) |
| JP (1) | JP5026985B2 (https=) |
| CN (1) | CN101080272B (https=) |
| AT (1) | ATE477848T1 (https=) |
| BR (1) | BRPI0515792A (https=) |
| CA (1) | CA2591037A1 (https=) |
| DE (2) | DE102004061016A1 (https=) |
| ES (1) | ES2351195T3 (https=) |
| MX (1) | MX2007007169A (https=) |
| RU (1) | RU2384364C2 (https=) |
| WO (1) | WO2006063669A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006032635A1 (de) * | 2006-07-13 | 2008-01-17 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Alkylmercaptanen in einem Mehrzonenfestbettreaktor |
| DE102007024576A1 (de) | 2007-05-25 | 2009-05-20 | Evonik Degussa Gmbh | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan aus kohlenstoff- und wasserstoffhaltigen Verbindungen |
| DE102009027837A1 (de) | 2009-07-20 | 2011-01-27 | Evonik Degussa Gmbh | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan aus kohlenstoffhaltigen Verbindungen, Schwefel und Wasserstoff |
| CN102993067A (zh) * | 2012-12-24 | 2013-03-27 | 贵州大学 | 一种制备甲硫醇的方法 |
| CN103007924B (zh) * | 2012-12-24 | 2015-07-08 | 贵州大学 | 一种催化剂的制备方法 |
| EP3187261A1 (de) | 2015-12-30 | 2017-07-05 | Evonik Degussa GmbH | Verfahren zur herstellung eines ein alkalimetall und eines übergangsmetall in oxidierter form enthaltenden katalysators |
| BR112018071639A2 (pt) | 2016-05-31 | 2019-02-12 | Novus International, Inc. | processo para produção de metil mercaptano a partir de sulfeto de dimetila |
| EP3689451A1 (en) * | 2019-01-29 | 2020-08-05 | Evonik Operations GmbH | Catalyst for the synthesis of alkyl mercaptan and process for its preparation |
| CN110724077A (zh) * | 2019-11-19 | 2020-01-24 | 山东益丰生化环保股份有限公司 | 一种1,2,3-三巯基乙基硫代丙烷的制备方法 |
| CN115608353B (zh) * | 2022-10-12 | 2024-03-01 | 山东新和成氨基酸有限公司 | 用于合成烷基硫醇的催化剂及其制备方法、烷基硫醇的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820062A (en) * | 1954-08-11 | 1958-01-14 | Pure Oil Co | Preparation of organic thiols |
| US3373097A (en) * | 1965-02-16 | 1968-03-12 | Interior Usa | Method for separation of a metalcontaining halide phase from a gangue-containing silicate phase and electrolysis of halide phase to obtain the metal |
| DE3125061C2 (de) | 1981-06-26 | 1984-03-15 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Acrolein bzw. Methacrolein durch katalytische Oxidation von Propylen bzw. Isobutylen oder tertiär-Butanol in sauerstoffhaltigen Gasgemischen |
| SU1608923A1 (ru) * | 1988-01-26 | 1996-11-10 | Специальное конструкторско-технологическое бюро катализаторов с опытным заводом | Способ приготовления катализатора для синтеза метилмеркаптана |
| RU2056940C1 (ru) * | 1992-03-26 | 1996-03-27 | Специальное конструкторско-технологическое бюро катализаторов с опытным заводом | Способ получения катализатора для синтеза метилмеркаптана и диметилсульфида |
| DE19639520C2 (de) * | 1996-09-26 | 1998-10-01 | Degussa | Katalysator, Verfahren zu seiner Herstellung und Verwendung zur Synthese von Alkylmercaptanen |
| DE19639584A1 (de) * | 1996-09-26 | 1998-04-23 | Degussa | Katalysator, Verfahren zu seiner Herstellung und Verwendung zur Synthese von Methylmercaptan |
| DE10319739A1 (de) * | 2003-04-30 | 2004-11-18 | Basf Ag | Katalysator zur Herstellung von Methylmercaptan aus Methanol und Schwefelwasserstoff |
| DE10338887A1 (de) * | 2003-08-23 | 2005-03-17 | Degussa Ag | Katalysator zur Synthese von Alkylmercaptan und Verfahren zu seiner Herstellung |
| DE102004037739A1 (de) * | 2004-08-04 | 2006-03-16 | Degussa Ag | Wolframat enthaltende Katalysatoren zur Synthese von Alkylmercaptan und Verfahren zu ihrer Herstellung |
-
2004
- 2004-12-18 DE DE102004061016A patent/DE102004061016A1/de not_active Withdrawn
-
2005
- 2005-11-24 CA CA002591037A patent/CA2591037A1/en not_active Abandoned
- 2005-11-24 CN CN2005800433717A patent/CN101080272B/zh not_active Expired - Fee Related
- 2005-11-24 WO PCT/EP2005/012598 patent/WO2006063669A1/de not_active Ceased
- 2005-11-24 RU RU2007127217/04A patent/RU2384364C2/ru not_active IP Right Cessation
- 2005-11-24 BR BRPI0515792-7A patent/BRPI0515792A/pt not_active Application Discontinuation
- 2005-11-24 MX MX2007007169A patent/MX2007007169A/es active IP Right Grant
- 2005-11-24 AT AT05813888T patent/ATE477848T1/de not_active IP Right Cessation
- 2005-11-24 ES ES05813888T patent/ES2351195T3/es not_active Expired - Lifetime
- 2005-11-24 DE DE502005010114T patent/DE502005010114D1/de not_active Expired - Lifetime
- 2005-11-24 JP JP2007545867A patent/JP5026985B2/ja not_active Expired - Fee Related
- 2005-11-24 EP EP05813888A patent/EP1824595B1/de not_active Expired - Lifetime
- 2005-12-15 US US11/304,438 patent/US8022254B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP5026985B2 (ja) | 2012-09-19 |
| WO2006063669A1 (de) | 2006-06-22 |
| EP1824595A1 (de) | 2007-08-29 |
| JP2008523967A (ja) | 2008-07-10 |
| US8022254B2 (en) | 2011-09-20 |
| EP1824595B1 (de) | 2010-08-18 |
| CN101080272A (zh) | 2007-11-28 |
| DE502005010114D1 (de) | 2010-09-30 |
| ES2351195T3 (es) | 2011-02-01 |
| CA2591037A1 (en) | 2006-06-22 |
| RU2007127217A (ru) | 2009-01-27 |
| CN101080272B (zh) | 2012-07-04 |
| US20060135816A1 (en) | 2006-06-22 |
| RU2384364C2 (ru) | 2010-03-20 |
| BRPI0515792A (pt) | 2008-08-05 |
| ATE477848T1 (de) | 2010-09-15 |
| MX2007007169A (es) | 2007-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: DEGUSSA GMBH, 40474 DUESSELDORF, DE |
|
| 8127 | New person/name/address of the applicant |
Owner name: EVONIK DEGUSSA GMBH, 40474 DUESSELDORF, DE |
|
| R005 | Application deemed withdrawn due to failure to request examination |
Effective date: 20111220 |