KR20130128478A - 글리세린의 탈수 반응에 의한 아크롤레인 및/또는 아크릴산의 제조용 촉매 및 방법 - Google Patents
글리세린의 탈수 반응에 의한 아크롤레인 및/또는 아크릴산의 제조용 촉매 및 방법 Download PDFInfo
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- KR20130128478A KR20130128478A KR1020137027958A KR20137027958A KR20130128478A KR 20130128478 A KR20130128478 A KR 20130128478A KR 1020137027958 A KR1020137027958 A KR 1020137027958A KR 20137027958 A KR20137027958 A KR 20137027958A KR 20130128478 A KR20130128478 A KR 20130128478A
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- Prior art keywords
- catalyst
- catalyst composition
- impregnation
- solution
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 110
- 239000003054 catalyst Substances 0.000 title claims abstract description 101
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 235000011187 glycerol Nutrition 0.000 title claims abstract description 52
- 238000006297 dehydration reaction Methods 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 26
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 22
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 81
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 239000011964 heteropoly acid Substances 0.000 claims abstract description 36
- 230000018044 dehydration Effects 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 30
- 230000000737 periodic effect Effects 0.000 claims abstract description 26
- 150000001768 cations Chemical class 0.000 claims abstract description 23
- 238000001354 calcination Methods 0.000 claims abstract description 20
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- 239000008247 solid mixture Substances 0.000 claims abstract description 17
- 238000001035 drying Methods 0.000 claims abstract description 11
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- 239000010936 titanium Substances 0.000 claims description 12
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
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- 239000011261 inert gas Substances 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
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- AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- 239000008367 deionised water Substances 0.000 description 6
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- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 239000011733 molybdenum Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
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- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
- 239000010937 tungsten Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010574 gas phase reaction Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
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- TTZGICPOSYHERT-UHFFFAOYSA-N [Si](O)(O)(O)O.[Mo] Chemical compound [Si](O)(O)(O)O.[Mo] TTZGICPOSYHERT-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
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- 238000006555 catalytic reaction Methods 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
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- 229910052732 germanium Inorganic materials 0.000 description 2
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- BCTWNMTZAXVEJL-UHFFFAOYSA-N phosphane;tungsten;tetracontahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] BCTWNMTZAXVEJL-UHFFFAOYSA-N 0.000 description 2
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- 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 description 1
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- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
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- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000001694 spray drying Methods 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
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
-
- 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
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/12—Silica and alumina
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0205—Impregnation in several steps
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C47/22—Acryaldehyde; Methacryaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/78—Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin or cold insoluble globulin [CIG]
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6887—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids from muscle, cartilage or connective tissue
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6893—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids related to diseases not provided for elsewhere
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
- G01N2333/705—Assays involving receptors, cell surface antigens or cell surface determinants
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Hematology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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- Cell Biology (AREA)
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- Gastroenterology & Hepatology (AREA)
- Biophysics (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/JP2009/067115 WO2011033689A1 (en) | 2009-09-18 | 2009-09-18 | Catalyst and process for preparing acrolein and/or acrylic acid by dehydration reaction of glycerin |
Related Parent Applications (1)
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| KR1020127008519A Division KR101399376B1 (ko) | 2009-09-18 | 2009-09-18 | 글리세린의 탈수 반응에 의한 아크롤레인 및/또는 아크릴산의 제조용 촉매 및 방법 |
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| KR1020127008519A Expired - Fee Related KR101399376B1 (ko) | 2009-09-18 | 2009-09-18 | 글리세린의 탈수 반응에 의한 아크롤레인 및/또는 아크릴산의 제조용 촉매 및 방법 |
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Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2013008279A1 (en) * | 2011-07-14 | 2013-01-17 | Nippon Kayaku Kabushiki Kaisha | Process for preparing catalyst used in production of acrolein and/or acrylic acid and process for preparing acrolein and/or acrylic acid by dehydration reaction of glycerin |
| WO2013017904A1 (en) * | 2011-07-29 | 2013-02-07 | Arkema France | Improved process of dehydration reactions |
| US20140206527A1 (en) * | 2011-07-29 | 2014-07-24 | Nippon Kayaku Kabushiki Kaisha | Catalyst For Preparing Acrolein And Acrylic Acid By Dehydration Of Glycerin, And Its Production Process |
| JP2013075842A (ja) * | 2011-09-29 | 2013-04-25 | Nippon Shokubai Co Ltd | アクロレインの製造方法、アクリル酸の製造方法、および親水性樹脂の製造方法 |
| US9422377B2 (en) | 2011-09-29 | 2016-08-23 | Nippon Shokubai Co., Ltd. | Process for producing acrolein, acrylic acid and derivatives thereof |
| WO2013056268A2 (en) * | 2011-10-06 | 2013-04-18 | Celanese International Corporation | Hydrogenation catalysts prepared from polyoxometalate precursors and process for using same to produce ethanol |
| WO2013084258A1 (en) * | 2011-12-06 | 2013-06-13 | Nippon Kayaku Kabushiki Kaisha | Catalyst for the manufacturing of acrylic acid and a process for producing acrylic acid by using the catalyst |
| CN104159883A (zh) * | 2012-03-07 | 2014-11-19 | 麦兰特公司 | α,β-不饱和羧酸及其酯的制备 |
| FR2989684B1 (fr) | 2012-04-18 | 2014-10-31 | Arkema France | Procede de fabrication d'acroleine et/ou d'acide acrylique a partir de glycerol |
| FR2997398B1 (fr) * | 2012-10-30 | 2014-11-21 | Adisseo France Sas | Procede de preparation de l’acroleine a partir de glycerol |
| KR101616528B1 (ko) | 2013-07-16 | 2016-04-28 | 주식회사 엘지화학 | 글리세린 탈수반응용 촉매, 이의 제조 방법 및 아크롤레인의 제조 방법 |
| WO2015046716A1 (ko) * | 2013-09-30 | 2015-04-02 | 주식회사 엘지화학 | 글리세린 탈수반응용 촉매, 이의 제조 방법 및 아크롤레인의 제조 방법 |
| KR101606191B1 (ko) | 2013-09-30 | 2016-03-24 | 주식회사 엘지화학 | 글리세린 탈수반응용 촉매, 이의 제조 방법 및 아크롤레인의 제조 방법 |
| KR20150055402A (ko) | 2013-11-13 | 2015-05-21 | 주식회사 엘지화학 | 글리세린 탈수반응용 촉매의 제조 방법 및 아크롤레인의 제조 방법 |
| KR101629003B1 (ko) | 2013-11-18 | 2016-06-09 | 주식회사 엘지화학 | 글리세린 탈수반응용 촉매, 이의 제조 방법 및 아크롤레인의 제조 방법 |
| FR3017617B1 (fr) | 2014-02-19 | 2016-02-12 | Arkema France | Procede de production d'acide acrylique bio-source |
| US9796648B2 (en) | 2014-05-02 | 2017-10-24 | University Of Tennessee Research Foundation | Glycerol dehydration methods and products thereof |
| WO2016026763A1 (en) | 2014-08-18 | 2016-02-25 | Basf Se | Process for preparing acrylic acid using a heterogeneous alumina catalyst |
| CN104892382B (zh) * | 2015-05-28 | 2017-08-11 | 珠海凯美科技有限公司 | 甘油液相氧化制备丙烯醛的方法 |
| KR102052708B1 (ko) | 2015-12-22 | 2019-12-09 | 주식회사 엘지화학 | 글리세린 탈수 반응용 촉매, 이의 제조 방법 및 상기 촉매를 이용한 아크롤레인의 제조 방법 |
| WO2017111392A1 (ko) * | 2015-12-22 | 2017-06-29 | 주식회사 엘지화학 | 글리세린 탈수 반응용 촉매, 이의 제조 방법 및 상기 촉매를 이용한 아크롤레인의 제조 방법 |
| WO2017111391A1 (ko) * | 2015-12-23 | 2017-06-29 | 주식회사 엘지화학 | 글리세린으로부터 아크릴산의 제조방법 |
| KR102044428B1 (ko) | 2015-12-23 | 2019-12-02 | 주식회사 엘지화학 | 글리세린으로부터 아크릴산의 제조방법 |
| KR102164613B1 (ko) * | 2016-03-28 | 2020-10-12 | 주식회사 엘지화학 | 글리세린 탈수 반응용 촉매, 이의 제조 방법 및 상기 촉매를 이용한 아크롤레인의 제조 방법 |
| WO2019139071A1 (ja) * | 2018-01-12 | 2019-07-18 | 積水化学工業株式会社 | 触媒及びその製造方法、並びに前記触媒を用いたジエン化合物の製造方法 |
| CN109433266A (zh) * | 2018-11-29 | 2019-03-08 | 东北师范大学 | 赖氨酸修饰的三中心POMs催化氧化甘油制备乳酸的技术 |
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| JP2001232207A (ja) | 2000-02-24 | 2001-08-28 | Idemitsu Petrochem Co Ltd | アルカン類の酸化脱水素触媒及びこれを用いたオレフィン類あるいは含酸素化合物の製造方法 |
| KR100413801B1 (ko) | 2001-10-30 | 2004-01-03 | 삼성전자주식회사 | 전도성 무기 나노 입자 함유 고분자 전해질 및 이를채용한 연료전지 |
| CN1301152C (zh) * | 2004-06-04 | 2007-02-21 | 南京工业大学 | 一种用于乙酸和正丁醇液相酯化反应的脱铝usy沸石负载杂多酸盐催化剂的制备方法 |
| FR2882053B1 (fr) | 2005-02-15 | 2007-03-23 | Arkema Sa | Procede de deshydratation du glycerol en acrolene |
| FR2882052B1 (fr) * | 2005-02-15 | 2007-03-23 | Arkema Sa | Procede de deshydratation du glycerol en acroleine |
| FR2884818B1 (fr) | 2005-04-25 | 2007-07-13 | Arkema Sa | Procede de preparation d'acide acrylique a partir de glycerol |
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| CN100528349C (zh) * | 2005-12-21 | 2009-08-19 | 中国科学院山西煤炭化学研究所 | 二甲醚氧化合成甲缩醛的催化剂及制法和应用 |
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| FR2897059B1 (fr) | 2006-02-07 | 2008-04-18 | Arkema Sa | Procede de preparation d'acide acrylique |
| FR2897058B1 (fr) | 2006-02-07 | 2008-04-18 | Arkema Sa | Procede de preparation d'acroleine |
| KR20090087095A (ko) | 2006-11-28 | 2009-08-14 | 드미트리 드미트리에비치 겐킨 | 조직의 세포외공간에서 증가된 데옥시리보핵산 함량과 관련된 인간 질병을 치료하는 방법 및 이 방법을 수행하기 위한 약학 제제 |
| FR2909999B1 (fr) | 2006-12-19 | 2009-04-03 | Arkema France | Procede de preparation d'acide acrylique a partir de glycerol |
| DE102007004350A1 (de) * | 2007-01-29 | 2008-07-31 | Evonik Degussa Gmbh | Verfahren zur Regenerierung eines Katalysators |
| FR2912742B1 (fr) | 2007-02-16 | 2010-03-05 | Arkema France | Procede de synthese d'acrylonitrile a partir de glycerol |
| US20090054538A1 (en) | 2007-08-24 | 2009-02-26 | Peterson Thomas H | Chemical production processes, systems, and catalyst compositions |
| JP5297450B2 (ja) * | 2008-04-16 | 2013-09-25 | 日本化薬株式会社 | グリセリンの脱水反応によるアクロレイン及びアクリル酸の製造用触媒と、その製造法 |
| WO2009127889A1 (en) * | 2008-04-16 | 2009-10-22 | Arkema France | Process for manufacturing acrolein from glycerol |
| WO2011046232A1 (en) * | 2009-10-15 | 2011-04-21 | Nippon Kayaku Kabushiki Kaisha | Process for preparing catalyst used in production of unsaturated aldehyde and/or unsaturated carboxylic acid by dehydration reaction of glycerin, and catalyst obtained |
-
2009
- 2009-09-18 US US13/496,339 patent/US20130053595A1/en not_active Abandoned
- 2009-09-18 IN IN2381DEN2012 patent/IN2012DN02381A/en unknown
- 2009-09-18 JP JP2012529412A patent/JP5784609B2/ja active Active
- 2009-09-18 WO PCT/JP2009/067115 patent/WO2011033689A1/en not_active Ceased
- 2009-09-18 EP EP13191431.9A patent/EP2695672B1/en active Active
- 2009-09-18 KR KR1020137027958A patent/KR20130128478A/ko not_active Abandoned
- 2009-09-18 BR BR112012006076-7A patent/BR112012006076A2/pt not_active Application Discontinuation
- 2009-09-18 SG SG2012018800A patent/SG179188A1/en unknown
- 2009-09-18 BR BR122013017195-9A patent/BR122013017195A2/pt not_active Application Discontinuation
- 2009-09-18 CN CN2009801625040A patent/CN102655931A/zh active Pending
- 2009-09-18 KR KR1020127008519A patent/KR101399376B1/ko not_active Expired - Fee Related
- 2009-09-18 EP EP09801291A patent/EP2477736A1/en not_active Withdrawn
-
2014
- 2014-09-19 US US14/491,433 patent/US9162954B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| SG179188A1 (en) | 2012-04-27 |
| EP2477736A1 (en) | 2012-07-25 |
| EP2695672A3 (en) | 2014-04-30 |
| KR20120093853A (ko) | 2012-08-23 |
| BR112012006076A2 (pt) | 2020-08-18 |
| JP2013505119A (ja) | 2013-02-14 |
| US9162954B2 (en) | 2015-10-20 |
| CN102655931A (zh) | 2012-09-05 |
| US20130053595A1 (en) | 2013-02-28 |
| KR101399376B1 (ko) | 2014-05-27 |
| WO2011033689A1 (en) | 2011-03-24 |
| JP5784609B2 (ja) | 2015-09-24 |
| EP2695672A2 (en) | 2014-02-12 |
| IN2012DN02381A (enExample) | 2015-08-21 |
| EP2695672B1 (en) | 2023-09-06 |
| BR122013017195A2 (pt) | 2020-09-24 |
| US20150005526A1 (en) | 2015-01-01 |
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