JP2014523855A - 銀含有編物でメタノールをホルムアルデヒドへ酸化的脱水素する方法 - Google Patents
銀含有編物でメタノールをホルムアルデヒドへ酸化的脱水素する方法 Download PDFInfo
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- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 88
- 239000004332 silver Substances 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 title claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims description 132
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title description 66
- 239000004744 fabric Substances 0.000 title description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 64
- 239000000835 fiber Substances 0.000 claims abstract description 34
- 150000001298 alcohols Chemical class 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 235000019256 formaldehyde Nutrition 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003570 air Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000005868 electrolysis reaction Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- -1 alkaryl alcohol Chemical compound 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- CUHVTYCUTYWQOR-UHFFFAOYSA-N formaldehyde Chemical compound O=C.O=C CUHVTYCUTYWQOR-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
-
- 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
- B01J23/50—Silver
-
- 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
- B01J35/31—Density
-
- 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
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
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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
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
- B01J35/58—Fabrics or filaments
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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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
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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
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
- B01J35/56—Foraminous structures having flow-through passages or channels, e.g. grids or three-dimensional monoliths
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
従来の触媒と比較して、C1〜C10アルデヒド、殊にホルムアルデヒドの改善された収量(例えば、ホルムアルデヒドに対するより高い選択性および例えばより僅かな触媒質量の際の同等なメタノール転化率)。
層厚および材料密度に関連して触媒充填の改善された均一性。
前記成形体、殊に線材/繊維構造体の幾何学的形状の意図的な調節、当該構造体の直径、および前記成形体の密度による本発明による触媒成形体の触媒特性に対する影響の可能性。
実施例1
ガス状水/メタノール混合物(水/メタノールのモル比率:1.0)を空気(140Nl/h)および窒素(50Nl/h)と、メタノール対酸素のモル比率が2.5である程度に混合した。この混合物を前記反応器の前方にある予熱器中で140℃に加熱し、引続き銀含有編物触媒上に導いた。前記触媒は、10mmの高さおよび20mmの直径を有する円筒形成形体から成り立っていた。前記成形体は、0.05mmの繊維直径を有する圧縮された銀製ウールから成り立っていた(前記成形体の密度:3g/cm3;空隙率:75%)。前記試験を断熱運転形式で20mmの内径を有する石英ガラス反応器中で実施した。前記反応器の断熱性は、受動的な隔離によって達成され、かつ補正加熱を完全に省略した。銀触媒で断熱的に実施された反応の着火を保証するために、メタノール/水/空気/窒素混合物を300℃に加熱し、その際に前記温度でメタノール/酸素のモル比は、7:1であり、かつ300Nl/hの窒素が計量供給された。断熱的着火が300℃で行なわれた。引続き、少しずつ水/メタノール/空気/窒素の上記組成物を計量供給した。計量供給量および予熱器温度を上記の記載と同様に調節した場合には、前記触媒床は、断熱的反応が着火された際に595℃の温度を達成した。95000h-1の触媒のガス負荷量が達成された。前記触媒床から流出する生成物混合物を熱交換器で120℃へ冷却した。前記生成物混合物の組成をガスクロマトグラフィーによって分析した。記載された条件下で99%のメタノール転化率および90%のホルムアルデヒド選択率が達成された。従来利用された、電気分解により製造された銀粒質物触媒(画分の大きさ0.5〜2mm)は、99%のメタノール転化率の際に87%のホルムアルデヒド選択率を達成した。
出発物質の計量供給および触媒の着火に関して試験の実施は、別記しない限り実施例1に相当した。触媒として、圧縮された銀製網からなる三次元的円筒形成形体を使用した。銀線材の直径は、0.076mmであった。触媒成形体の高さは、20mmであり、その直径は、20mmであった。記載された条件下で、98%のメタノール転化率および90%のホルムアルデヒド選択率が達成された。従来利用された、電気分解により製造された銀粒質物触媒(画分の大きさ0.5〜2mm)は、98%のメタノール転化率の際に87%のホルムアルデヒド選択率を達成した。
出発物質の計量供給および触媒の着火に関して試験の実施は、別記しない限り実施例1に相当した。触媒として、編織されかつ引続き圧縮された銀線材からなる三次元的円筒形成形体が使用された。前記銀線材の直径は、0.1mmであった。前記の圧縮された編物の密度は、3g/cm3であった。前記触媒成形体の高さは、10mmであり、その直径は、20mmであった。記載された条件下で96%のメタノール転化率および91%のホルムアルデヒド選択率が達成された。従来利用された、電気分解により製造された銀粒質物触媒(画分の大きさ0.5〜2mm)は、96%のメタノール転化率の際に90%のホルムアルデヒド選択率を達成した。
Claims (8)
- 銀含有繊維および/または銀含有糸の空間内での三次元的な変形および/または配置によって得られる触媒成形体でC1〜C10アルコールを酸化的脱水素することによって、C1〜C10アルデヒドを製造する方法であって、当該銀含有繊維および/または当該銀含有糸の基本的に矩形または正方形の横断面の平均直径または平均的な対角線の長さが30μm〜200μmの範囲内にあることを特徴とする、前記方法。
- C1〜C10アルデヒドは、ホルムアルデヒドであり、およびC1〜C10アルコールは、メタノールであることを特徴とする、請求項1記載の方法。
- 前記銀含有繊維および/または前記銀含有糸の基本的に矩形または正方形の横断面の平均直径または平均的な対角線の長さは、30μm〜150μmの範囲内にあることを特徴とする、請求項1または2記載の方法。
- 前記銀含有繊維および/または前記銀含有糸の基本的に矩形または正方形の横断面の平均直径または平均的な対角線の長さは、30μm〜70μmの範囲内にあることを特徴とする、請求項1または2記載の方法。
- 成形された銀含有繊維および/または銀含有糸は、2g/cm3〜4g/cm3の範囲内の密度を有することを特徴とする、請求項1から4までのいずれか1項に記載の方法。
- 空間内での三次元的な変形および/または配置は、乱雑に行なわれるか、または整然と行なわれることを特徴とする、請求項1から5までのいずれか1項に記載の方法。
- 成形された銀含有繊維および/または銀含有糸は、乱雑に存在しかつもつれ合った塊の形で存在することを特徴とする、請求項1から6までのいずれか1項に記載の方法。
- 成形された銀含有繊維および/または銀含有糸は、整然としておりかつ編物または網の形で存在することを特徴とする、請求項1から6までのいずれか1項に記載の方法。
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EP11163635.3 | 2011-04-26 | ||
EP11163635 | 2011-04-26 | ||
PCT/EP2012/057190 WO2012146528A1 (de) | 2011-04-26 | 2012-04-19 | Verfahren zur oxidativen dehydrierung von methanol zu formaldehyd an silberhaltigen gestricken |
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EP (1) | EP2701841B1 (ja) |
JP (1) | JP2014523855A (ja) |
KR (1) | KR20140027300A (ja) |
CN (1) | CN103492071B (ja) |
AR (1) | AR086063A1 (ja) |
BR (1) | BR112013027184A2 (ja) |
CA (1) | CA2833915A1 (ja) |
DK (1) | DK2701841T3 (ja) |
ES (1) | ES2544839T3 (ja) |
PL (1) | PL2701841T3 (ja) |
PT (1) | PT2701841E (ja) |
WO (1) | WO2012146528A1 (ja) |
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JP2015514754A (ja) * | 2012-04-20 | 2015-05-21 | メディシナル バイオコンバージェンス リサーチ センター | 新規アミノピリジン誘導体の癌予防又は治療用途 |
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EP3585515A1 (de) | 2017-02-24 | 2020-01-01 | Basf Se | Silber-katalysatorsystem mit verringertem druckabfall zur oxidativen dehydrierung von alkoholen |
EP3539657A1 (en) | 2018-03-14 | 2019-09-18 | Basf Se | Improved catalysts comprising silver based intermetallic compounds |
WO2020099390A1 (en) | 2018-11-13 | 2020-05-22 | Basf Se | Catalyst bed comprising silver catalyst bodies and process for the oxidative dehydrogenation of olefinically unsaturated alcohols |
WO2023099727A1 (en) | 2021-12-03 | 2023-06-08 | Basf Se | Process for preparing isoprenal and/or prenal |
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- 2012-04-19 JP JP2014506825A patent/JP2014523855A/ja not_active Ceased
- 2012-04-19 PL PL12716396T patent/PL2701841T3/pl unknown
- 2012-04-19 WO PCT/EP2012/057190 patent/WO2012146528A1/de active Application Filing
- 2012-04-19 CN CN201280020040.1A patent/CN103492071B/zh not_active Expired - Fee Related
- 2012-04-19 EP EP12716396.2A patent/EP2701841B1/de not_active Not-in-force
- 2012-04-19 ES ES12716396.2T patent/ES2544839T3/es active Active
- 2012-04-19 PT PT127163962T patent/PT2701841E/pt unknown
- 2012-04-19 KR KR1020137030951A patent/KR20140027300A/ko not_active Application Discontinuation
- 2012-04-19 DK DK12716396.2T patent/DK2701841T3/en active
- 2012-04-19 BR BR112013027184A patent/BR112013027184A2/pt not_active IP Right Cessation
- 2012-04-19 CA CA2833915A patent/CA2833915A1/en not_active Abandoned
- 2012-04-25 AR ARP120101434A patent/AR086063A1/es unknown
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US3678139A (en) * | 1968-02-02 | 1972-07-18 | Du Pont | Conversion of methanol to formaldehyde using a bismuth molybdate on silica catalyst |
US4076754A (en) * | 1976-01-20 | 1978-02-28 | E. I. Du Pont De Nemours And Company | Formaldehyde manufacturing process |
JPS5439018A (en) * | 1977-08-02 | 1979-03-24 | Akzo Nv | Process for preparing isocyanate from formamide |
JPS5885834A (ja) * | 1981-11-04 | 1983-05-23 | バイエル・アクチエンゲゼルシヤフト | ホルムアルデヒドの製造法 |
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JP2015514754A (ja) * | 2012-04-20 | 2015-05-21 | メディシナル バイオコンバージェンス リサーチ センター | 新規アミノピリジン誘導体の癌予防又は治療用途 |
Also Published As
Publication number | Publication date |
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CN103492071A (zh) | 2014-01-01 |
CN103492071B (zh) | 2015-08-12 |
WO2012146528A1 (de) | 2012-11-01 |
EP2701841A1 (de) | 2014-03-05 |
EP2701841B1 (de) | 2015-06-17 |
KR20140027300A (ko) | 2014-03-06 |
PL2701841T3 (pl) | 2015-11-30 |
DK2701841T3 (en) | 2015-09-21 |
AR086063A1 (es) | 2013-11-13 |
PT2701841E (pt) | 2015-08-03 |
BR112013027184A2 (pt) | 2016-12-27 |
CA2833915A1 (en) | 2012-11-01 |
ES2544839T3 (es) | 2015-09-04 |
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