JP6866344B2 - 酢酸ビニルモノマー生成のための高い幾何学的表面積の触媒 - Google Patents
酢酸ビニルモノマー生成のための高い幾何学的表面積の触媒 Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims description 208
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 title claims description 20
- 230000015572 biosynthetic process Effects 0.000 title claims description 5
- 238000000034 method Methods 0.000 claims description 46
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 42
- 239000000463 material Substances 0.000 claims description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 24
- 229910052737 gold Inorganic materials 0.000 claims description 20
- 229910052763 palladium Inorganic materials 0.000 claims description 20
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 239000000377 silicon dioxide Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000012495 reaction gas Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 235000011056 potassium acetate Nutrition 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 2
- 239000010931 gold Substances 0.000 description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
- 238000001035 drying Methods 0.000 description 23
- 238000001125 extrusion Methods 0.000 description 20
- 238000005516 engineering process Methods 0.000 description 13
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- 239000000203 mixture Substances 0.000 description 10
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- 150000003839 salts Chemical class 0.000 description 8
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- 230000000052 comparative effect Effects 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 241000219793 Trifolium Species 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 1
- 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 1
- 241000736305 Marsilea quadrifolia Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000005465 channeling Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- -1 gold (III) tetrachloride Chemical compound 0.000 description 1
- RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 1
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
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Description
本出願は、2015年7月22日に出願された米国仮特許第62/195,499号に対する優先権を主張するものであり、その全体の開示は、いかなる及び全ての目的で参照により本明細書に組み込まれる。
本技術は、概して、酢酸ビニルモノマー生成の分野に関連する。より具体的には、触媒は、酢酸ビニルモノマーの合成に対して極めて活性に富み、高い選択性を提示する。本技術はまた、触媒を作製する方法及び触媒に関与するプロセスを提供する。
態様では、外面、約60重量%〜約99重量%のシリカ、約1.0重量%〜約5.0重量%のアルミナを含む支持体、外面に隣接する支持体内に配置される触媒層であって、Pd、Au、及び酢酸カリウム(KOAc)を更に含む触媒層、約130m2/g〜約300m2/gのブルナウアー−エメット−テラー表面積、及び約550m2/m3〜約1500m2/m3の充填層体積当たりの幾何学的表面積(GSA/PBV)を含む触媒が提供され、そこで、(a)KOAcは、触媒の約60kg/m3〜約150kg/m3であるか、または(b)触媒層は、約50μm〜約150μmの平均厚さを有するか、または(c)KOAcが触媒の約60kg/m3〜約150kg/m3であり、触媒層が約50μm〜約150μmの平均厚さを有する。いくつかの実施形態では、KOAcは、触媒の約65kg/m3〜約100kg/m3であり得る。上記の実施形態のいずれかにおいて、触媒層は、約50μm〜約550μmの厚さであり得る。
したがって、例えば、1〜3個の原子を有する基は、1、2、または3個の原子を有する基を指す。同様に、1〜5個の原子を有する基は、1、2、3、4、または5個の原子を有する基を指す、等。
球形触媒に関して、球形触媒の幾何学的表面積(GSA)は、原則的に4π(r)2であり、そこで、「r」は、球形触媒の直径の半分である。
この押出物触媒の集合体からの触媒の質量当たりの幾何学的表面積を決定するために、質量対長さの線形相関が、>50の押出物の質量及び長さを測定することによって評価され得る。押出物触媒に関して、図3に示される通り、図2で使用された有心四葉形押出物触媒の長さと質量との間に強い相関がある。図2の長さ分配、及び図3の直線質量対長さ相関を使用して、図2における150の押出物触媒の同じ分配に対する質量当たりの幾何学的表面積が、例えば、方程式2を使用することによって計算され得る。「粒子の質量i」は、図3の直線質量対長さ相関から見ることができる。
質量当たりの幾何学的表面積を使用してGSA/PBVを得るために、問題になっている触媒系(例えば、特定の押出物の種類、球形触媒、等)の充填層密度が測定される。充填層密度は、いかなる及び全ての目的で参照により全体として本明細書に組み込まれる、ASTM−D4164−82に記載される方法を含むが、これに限定されない、様々な方法によって決定され得る。質量当たりの幾何学的表面積(m2/gの単位)を充填層密度(g/m3の単位での「質量/容積」)で乗算すると、方程式3に示される通り、GSA/PBVを提供するために質量単位が相殺される。
本技術の2つの触媒(触媒1及び触媒2)と比較触媒(「比較」)との組成物及び特性が、以下の表1に提供される。SiO2及びAl2O3を、約0.1重量%の検出限界を有するX線蛍光によって決定した。Pd、Au、及びKを、誘導結合プラズマ原子発光分析によって決定した。測定された全てのカリウムは、酢酸カリウムからであると仮定した。
VAM生成を、ガスチャネリングを排除するために触媒粒子空隙を充填する炭化ケイ素を有する等温固定層反応器において評価し、図1及び2の結果は、150℃での操作の20時間後である。反応器に対する操作条件は、表2に提供される。
A.触媒であって、
外面と、
約60重量%〜約99重量%のシリカと、
約1.0重量%〜約5.0重量%のアルミナと、
を含む支持体と、
外面に隣接する支持体内に配置される触媒層であって、Pd、Au、及び酢酸カリウム(KOAc)を更に含む触媒層と、
約130m2/g〜約300m2/gのブルナウアー−エメット−テラー表面積と、
約550m2/m3〜約1500m2/m3の充填層体積当たりの幾何学的表面積と、
を含む触媒であって、
(a)KOAcは、触媒の約60kg/m3〜約150kg/m3であるか、または
(b)触媒層は、約50μm〜約150μmの平均厚さを有するか、または
(c)KOAcは、触媒の約60kg/m3〜約150kg/m3であり、触媒層は、約50μm〜約150μmの平均厚さを有する、
触媒。
B.KOAcが、触媒の約65kg/m3〜約100kg/m3である、A項の触媒。
C.触媒層が、約50μm〜約550μmの平均厚さを有する、A項またはB項の触媒。
D.触媒層が、約100μm〜約400μmの平均厚さを有する、A〜C項のいずれか1項の触媒。
E.触媒層が、約100μm〜約200μmの平均厚さを有する、A〜D項のいずれか1項の触媒。
F.アルミナが、約1.0重量%〜約3.0重量%である、A〜E項のいずれか1項の触媒。
G.触媒中のPdが、約3g/L〜約15g/Lである、A〜F項のいずれか1項の触媒。
H.触媒中のAuが、約0.9g/L〜約7.0g/Lである、A〜G項のいずれか1項の触媒。
I.PdのAuに対する質量比が、約3.5:1〜約2.0:1である、A〜H項のいずれか1項の触媒。
J.触媒のブルナウアー−エメット−テラー表面積が、約200m2/g〜約250m2/gである、A〜I項のいずれか1項の触媒。
K.触媒の充填層体積当たりの幾何学的表面積が、約600m2/m3〜約1500m2/m3である、A〜J項のいずれか1項の触媒。
L.触媒の充填層体積当たりの幾何学的表面積が、約800m2/m3〜約1300m2/m3である、A〜K項のいずれか1項の触媒。
M.触媒の空隙率が、約35%〜約55%である、A〜L項のいずれか1項の触媒。
N.触媒は、円筒形、球形、管状、複小葉形、輪状、星形、鞍状、溝付き形、または畝状の少なくとも1つを含む形状である、A〜M項のいずれか1項の触媒。
O.触媒層を除いて、支持体は、Pd、Au、及びKOAcを実質的に含まない、A〜N項のいずれか1項の触媒。
P.A〜O項のいずれか1項の触媒を作製する方法であって、Pd及びAuを有する外面を含む支持体材料に浸透して、外面に隣接する支持体材料内に配置される金属含有層を提供することを含み、
支持体材料は、
約60重量%〜約99重量%のシリカと、
約1.0重量%〜約5.0重量%のアルミナとを含み、
金属含有層は、Pd及びAuを更に含む、方法。
Q.支持体材料に浸透することは、支持体材料を、Pdの塩、Auの塩、またはそれらの混合物を含む塩類溶液に接触させることを含む、P項の方法。
R.塩類溶液に接触させることに続いて、支持体材料に浸透することは、支持体材料を塩基性溶液に接触させることを含む、Q項の方法。
S.浸透ステップに続く洗浄ステップを更に含む、P〜R項のいずれか1項の方法。
T.浸透ステップに続いて支持体材料を乾燥させることを更に含む、P〜S項のいずれか1項の方法。
U.浸透ステップに続く乾燥は、約40℃〜約250℃の温度で生じる、T項の方法。
V.洗浄ステップに続いて支持体材料を乾燥させることを更に含む、S〜U項のいずれか1項の方法。
W.洗浄ステップに続く乾燥は、約40℃〜約250℃の温度で生じる、V項の方法。
X.金属含有層を還元剤に曝すことを更に含む、P〜W項のいずれか1項の方法。
Y.曝すステップは、約15℃〜約500℃の温度で生じる、X項の方法。
Z.方法は、金属含有層をKOAcに含浸させることを更に含む、P〜Y項のいずれか1項の方法。
AA.含浸ステップが、曝すステップの前に生じる、Z項の方法。
AB.含浸ステップが、曝すステップの後に生じる、Z項の方法。
AC.含浸ステップに続いて支持体材料を乾燥させることを更に含む、Z〜AB項のいずれか1項の方法。
AD.酢酸ビニルモノマーを生成するために、反応ガスを、A〜O項のいずれか1項の触媒に接触させることを含むプロセスであって、反応ガスは、エチレン、酢酸、及びO2を含む、プロセス。
Claims (13)
- 酢酸ビニルモノマーの合成用の触媒であって、
外面と、
60重量%〜99重量%のシリカと、
1.0重量%〜5.0重量%のアルミナと、
を含む支持体と、
前記外面に隣接する前記支持体内に配置された触媒層であって、Pd、Au、及び酢酸カリウム(KOAc)を更に含む、触媒層と、
130m2/g〜300m2/gのブルナウアー−エメット−テラー(BET)表面積と、
550m2/m3〜1500m2/m3の、充填層体積当たりの幾何学的表面積と、
を含み、
(a)前記KOAcは、前記触媒の60kg/m3〜90kg/m3であるか、または
(c)前記KOAcは、前記触媒の60kg/m3〜90kg/m3であり、かつ前記触媒層は、50μm〜150μmの平均厚さを有し、
Pdが3g/L〜15g/Lで前記触媒中に存在し、かつAuが0.9g/L〜7.0g/Lで前記触媒中に存在する、
前記触媒。 - 前記KOAcが、前記触媒の65kg/m3〜90kg/m3である、請求項1に記載の触媒。
- 前記触媒層が、100μm〜150μmの平均厚さを有する、請求項1または2に記載の触媒。
- 前記アルミナが1.0重量%〜3.0重量%で前記触媒中に存在する、請求項1から3までの何れか1項に記載の触媒。
- PdのAuに対する質量比が、3.5:1〜2.0:1である、請求項1から4までの何れか1項に記載の触媒。
- 前記触媒の前記ブルナウアー−エメット−テラー(BET)表面積が、200m2/g〜250m2/gである、請求項1から5までの何れか1項に記載の触媒。
- 前記触媒の前記充填層体積当たりの幾何学的表面積が、800m2/m3〜1300m2/m3である、請求項1から6までの何れか1項に記載の触媒。
- 前記触媒の空隙率が、35%〜55%である、請求項1から7までの何れか1項に記載の触媒。
- 前記触媒層を除いて、前記支持体は、Pd、Au、及びKOAcを実質的に含まない、請求項1から8までの何れか1項に記載の触媒。
- 前記触媒は、円筒形、球形、管状、複小葉形、輪状、星形、鞍状、溝付き形、または畝状のうちの少なくとも1つを含む形状である、請求項1から9までの何れか1項に記載の触媒。
- 反応ガスを、請求項1〜10のいずれか1項に記載の触媒に接触させて、酢酸ビニルモノマーを製造することを含むプロセスであって、前記反応ガスは、エチレン、酢酸、及びO2を含む、前記プロセス。
- 酢酸ビニルモノマーの合成用の触媒であって、
外面と、
60重量%〜99重量%のシリカと、
1.0重量%〜5.0重量%のアルミナと、
を含む支持体と、
前記外面に隣接する前記支持体内に配置された触媒層であって、Pd、Au、及び酢酸カリウム(KOAc)を更に含む、触媒層と、
130m2/g〜300m2/gのブルナウアー−エメット−テラー(BET)表面積と、
550m2/m3〜1500m2/m3の、充填層体積当たりの幾何学的表面積と、
を含み、
前記触媒の空隙率は、35%〜55%であり
(a)前記KOAcは、前記触媒の60kg/m3〜150kg/m3であるか、または
(b)前記触媒層は、50μm〜150μmの平均厚さを有するか、または
(c)前記KOAcは、前記触媒の60kg/m3〜150kg/m3であり、かつ前記触媒層は、50μm〜150μmの平均厚さを有する、
前記触媒。 - 外面を含む支持体材料にPd及びAuを浸透させて、外面に隣接する支持体材料内に配置される金属含有層を提供することを有し、
前記支持体材料は、
60重量%〜99重量%のシリカと、
1.0重量%〜5.0重量%のアルミナと、
を含み、
前記金属含有層はさらにPdおよびAuを含有する、請求項12に記載の触媒の作製方法。
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Publication number | Priority date | Publication date | Assignee | Title |
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Family Cites Families (167)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3284851A (en) | 1964-02-03 | 1966-11-15 | Zernay Henry James | Extruding means having rotary head |
US3920578A (en) | 1968-06-12 | 1975-11-18 | Du Pont | Colloidal silica-based binder vehicles and gels |
US3857780A (en) | 1972-05-22 | 1974-12-31 | W Gustafson | Hydroforming petroleum fractions in gas phase using shaped catalyst particles |
SE420596B (sv) | 1975-03-25 | 1981-10-19 | Osaka Packing | Formad kropp av amorf kiseldioxid, eventuellt innehallande kalciumkarbonat, sett att framstella en formad kropp av amorf kiseldioxid samt partikel av amorf kiseldioxid for framstellning av en formad kropp |
US4142994A (en) | 1975-10-20 | 1979-03-06 | Filtrol Corporation | Shaped catalyst support |
DE2903193C3 (de) | 1979-01-27 | 1981-07-02 | Basf Ag, 6700 Ludwigshafen | Verwendung eines Katalysators aus Kobaltoxid und/oder Nickeloxid sowie Molybdäntrioxid und Tonerde für die hydrierende Raffination von Erdölkohlenwasserstoffen |
SU865792A1 (ru) | 1979-09-07 | 1981-09-23 | Предприятие П/Я Р-6518 | Способ получени шарикового силикагел |
JPS56141842A (en) | 1980-04-07 | 1981-11-05 | Kanegafuchi Chem Ind Co Ltd | Catalyst formed in novel cylindrical shape |
JPS57171435A (en) | 1981-04-14 | 1982-10-22 | Noritake Co Ltd | Alumina catalyst carrier for partial oxidation and prepatation thereof |
US4441990A (en) | 1982-05-28 | 1984-04-10 | Mobil Oil Corporation | Hollow shaped catalytic extrudates |
JPS5946132A (ja) | 1982-09-06 | 1984-03-15 | Nippon Shokubai Kagaku Kogyo Co Ltd | メタクロレイン合成用触媒 |
US4780446A (en) | 1982-09-30 | 1988-10-25 | W. R. Grace & Co. | Alumina-silica cogel |
US4510262A (en) | 1983-10-17 | 1985-04-09 | W. R. Grace & Co. | Doubly promoted catalyst with high geometric surface area |
US4541996A (en) | 1983-10-17 | 1985-09-17 | W. R. Grace & Co. | Process for utilizing catalyst with high geometric surface area |
US4510263A (en) | 1983-10-17 | 1985-04-09 | W. R. Grace & Co. | Catalyst with high geometric surface area alumina extrudate and catalyst with high geometric surface area |
US4937394A (en) | 1984-04-23 | 1990-06-26 | Mallinckrodt, Inc. | Silica catalyst supports for hydration of ethylene to ethanol |
GB8412276D0 (en) | 1984-05-14 | 1984-06-20 | Telephone Cables Ltd | Manufacture of optical fibre cable |
DE3437641A1 (de) | 1984-10-13 | 1986-04-17 | Kanthal GmbH, 6082 Mörfelden-Walldorf | Abgas-katalysator |
DE3539195A1 (de) | 1984-11-08 | 1986-05-07 | Chevron Research Co., San Francisco, Calif. | Hydroprocessing-katalysator bestimmter geometrischer gestalt |
US4631267A (en) | 1985-03-18 | 1986-12-23 | Corning Glass Works | Method of producing high-strength high surface area catalyst supports |
US4631268A (en) | 1985-03-18 | 1986-12-23 | Corning Glass Works | Preparation of monolithic catalyst support structures having an integrated high surface area phase |
JPS6268546A (ja) | 1985-09-19 | 1987-03-28 | Nippon Oil Co Ltd | 触媒担体の製造方法 |
US4673664A (en) | 1985-10-07 | 1987-06-16 | American Cyanamid Company | Shape for extruded catalyst support particles and catalysts |
GB8527663D0 (en) | 1985-11-08 | 1985-12-11 | Ici Plc | Catalyst precursors |
JPH0661463B2 (ja) | 1986-12-01 | 1994-08-17 | 松下電器産業株式会社 | 担体および触媒体 |
DE3643248A1 (de) | 1986-12-18 | 1988-06-30 | Basf Ag | Silberkatalysator, seine herstellung und verwendung |
GB8722459D0 (en) | 1987-09-24 | 1987-10-28 | Shell Int Research | Silica extrudates |
US4868150A (en) | 1987-12-22 | 1989-09-19 | Rhone-Poulenc Inc. | Catalyst support material containing lanthanides |
EP0355231B1 (en) | 1988-08-17 | 1995-02-08 | Toa Nenryo Kogyo Kabushiki Kaisha | Heat-resistant catalyst carrier moldings and catalysts for combustion |
FR2635987B1 (fr) | 1988-09-02 | 1993-10-15 | Rhone Poulenc Chimie | Catalyseurs pour le traitement des effluents gazeux et procede de traitement de ces effluents |
US5004709A (en) | 1989-03-16 | 1991-04-02 | Allied-Signal Inc. | High surface area silicon nitride and use thereof |
US4950628A (en) | 1989-04-19 | 1990-08-21 | Corning Incorporated | Material and process to produce low thermal expansion cordierite structures |
DE3930534A1 (de) | 1989-09-13 | 1991-03-21 | Degussa | Verfahren zur herstellung von acrolein durch katalytische gasphasenoxidation von propen |
GB8925979D0 (en) | 1989-11-16 | 1990-01-04 | Shell Int Research | Process for the preparation of extrudates,extrudates,and use of the extrudates |
AT400687B (de) | 1989-12-04 | 1996-02-26 | Plansee Tizit Gmbh | Verfahren und strangpresswerkzeug zur herstellung eines rohlings mit innenliegenden bohrungen |
DE4018512A1 (de) | 1990-06-09 | 1991-12-12 | Wacker Chemie Gmbh | Zylindrisch geformter katalysator und dessen verwendung bei der oxichlorierung von ethylen |
DE69101032T2 (de) | 1990-07-03 | 1994-08-11 | Kuraray Co | Katalysator und Verfahren zur Herstellung von ungesättigten Estern. |
DE4128201A1 (de) | 1991-08-26 | 1993-03-04 | Hoechst Ceram Tec Ag | Reaktionsrohr aus aluminiumoxid und verfahren zu seiner herstellung |
DE4142902A1 (de) | 1991-12-23 | 1993-06-24 | Sued Chemie Ag | Formlinge auf der basis von pyrogener kieselsaeure |
IT1256156B (it) | 1992-10-06 | 1995-11-29 | Montecatini Tecnologie Srl | Catalizzatore in granuli particolarmente per la deidrogenazione ossidativa di metanolo a formaldeide |
US5861353A (en) | 1992-10-06 | 1999-01-19 | Montecatini Tecnologie S.R.L. | Catalyst in granular form for 1,2-dichloroethane synthesis |
JP3458428B2 (ja) | 1992-10-21 | 2003-10-20 | 株式会社豊田中央研究所 | 多孔体の製造方法 |
DE4242227A1 (de) | 1992-12-15 | 1994-06-16 | Heraeus Quarzglas | Katalysatorträger und Verfahren für seine Herstellung |
US5507980A (en) | 1993-07-06 | 1996-04-16 | Aristech Chemical Corporation | Basic inorganic binders |
US5466652A (en) | 1994-02-22 | 1995-11-14 | The Standard Oil Co. | Process for the preparation of vinyl acetate catalyst |
US5633066A (en) | 1994-03-21 | 1997-05-27 | Corning Incorporated | Honeycomb structures having non-parallel cells and method of making |
DE19501891C1 (de) * | 1995-01-23 | 1996-09-26 | Degussa | Verfahren zur Herstellung eines Trägerkatalysators und seine Verwendung für die Produktion von Vinylacetat |
IT1282267B1 (it) | 1995-03-14 | 1998-03-16 | Montecatini Tecnologie Srl | Catalizzatori e supporti per catalizzatori ottenuti per pastigliatura |
DE19519616A1 (de) | 1995-05-29 | 1996-12-05 | Marc Andreas De Ruiter | Spezielle Form von Körpern mit adsorbierenden Eigenschaften und ihre mögliche Verbindung zu festen Gebilden |
DE19533484A1 (de) | 1995-09-12 | 1997-03-13 | Basf Ag | Monomodale und polymodale Katalysatorträger und Katalysatoren mit engen Porengrößenverteilungen und deren Herstellverfahren |
IT1276155B1 (it) | 1995-11-21 | 1997-10-27 | Montecatini Tecnologie Srl | Catalizzatori per l'ossiclorurazione dell'etilene,procedimento per la loro preparazione e procedimento di ossiclorurazione impiegante gli |
IT1283207B1 (it) | 1996-03-08 | 1998-04-16 | Montecatini Tecnologie Srl | Catalizzatori per la deidrogenazione di etilbenzene a stirene |
US5935896A (en) | 1996-05-02 | 1999-08-10 | Basf Aktiengesellschaft | Catalyst supports and catalysts for dehydrocyanation reactions and processes for producing them |
DE19619961A1 (de) | 1996-05-17 | 1997-11-20 | Degussa | Preßlinge auf Basis von pyrogen hergestelltem Siliciumdioxid |
FI104202B1 (fi) | 1997-09-05 | 1999-11-30 | Kemira Metalkat Oy | Katalysaattorikennorakenne |
JPH11236602A (ja) | 1998-02-24 | 1999-08-31 | Hitachi Metals Ltd | 螺旋状孔を有する棒材の製造方法およびその製造装置 |
DE19828491A1 (de) * | 1998-06-26 | 1999-12-30 | Degussa | Formkörper auf Basis von Siliciumdioxid |
JP2000135437A (ja) | 1998-10-30 | 2000-05-16 | Catalysts & Chem Ind Co Ltd | 水素化処理触媒およびその製造方法 |
GB9825109D0 (en) | 1998-11-16 | 1999-01-13 | Dytech Corp Ltd | Porous ceramic matrices |
IT1306194B1 (it) | 1999-01-08 | 2001-05-30 | Sued Chemie Mt Srl | Catalizzatori per reazioni esotermiche su letto fisso. |
ATE296163T1 (de) * | 1999-04-08 | 2005-06-15 | Albemarle Netherlands Bv | Verfahren zur sulfidierung eines organischen stickstoff und carbonyl enthaltenden hydrobehandlungskatalysators |
IT1312337B1 (it) | 1999-05-07 | 2002-04-15 | Agip Petroli | Composizione catalitica per l'upgrading di idrocarburi aventi punti di ebollizione nell'intervallo della nafta |
FR2793706B1 (fr) | 1999-05-18 | 2001-08-03 | Total Raffinage Distribution | Support catalytique a base d'oxyde d'un metal du groupe ivb de la classification periodique des elements, sa preparation et ses utilisations |
DE19924453A1 (de) | 1999-05-28 | 2001-01-18 | Grace Gmbh & Co Kg | Formkörper aus Silicagel und porösen amorphen Mischoxiden, Verfahren zu ihrer Herstellung und deren Verwendung |
FR2795341B1 (fr) | 1999-06-25 | 2001-08-17 | Inst Francais Du Petrole | Catalyseur contenant une zeolithe chargee en element des groupes vib et/ou viii et son utilisation en hydroraffinage et hydrocraquage de coupes hydrocarbonees |
AU5616900A (en) | 1999-06-29 | 2001-01-31 | Abb Lummus Global Inc. | Process for coating metal fibrous material |
DE10048219A1 (de) | 2000-02-10 | 2002-04-11 | Sued Chemie Ag | Katalysator für die Hydrierung von ungesättigten Kohlenwasserstoffen |
US6569318B2 (en) | 2000-02-23 | 2003-05-27 | Institut Francais Du Petrole | Process for conversion of hydrocarbons on a catalyst with controlled acidity |
DE10009017A1 (de) | 2000-02-25 | 2001-09-06 | Basf Ag | Geformte Katalysatoren |
JP4252188B2 (ja) | 2000-03-13 | 2009-04-08 | 独立行政法人科学技術振興機構 | 螺旋の向きが制御された螺旋構造を有する有機無機複合体の製造方法 |
US6794332B2 (en) * | 2000-07-07 | 2004-09-21 | Saudi Basic Industries Corporation | Highly selective shell impregnated catalyst of improved space time yield for production of vinyl acetate |
EP1184077B1 (en) | 2000-08-30 | 2005-10-19 | Haldor Topsoe A/S | Hydrotreating catalyst particles |
CN1150996C (zh) | 2000-09-29 | 2004-05-26 | 中国石油化工股份有限公司 | 加氢催化剂载体及其制备方法和用途 |
JP2002177793A (ja) | 2000-10-02 | 2002-06-25 | Nippon Soken Inc | セラミック担体およびセラミック触媒体 |
JP4731668B2 (ja) | 2000-10-17 | 2011-07-27 | 株式会社豊田中央研究所 | 多孔質成形体の製造方法 |
US20020179887A1 (en) | 2001-05-01 | 2002-12-05 | Yongxian Zeng | Supported perovskite-type oxides and methods for preparation thereof |
US20020198429A1 (en) | 2001-05-18 | 2002-12-26 | Conoco Inc. | Inducing turbulent flow in catalyst beds |
AU2002331370B2 (en) | 2001-08-01 | 2006-12-21 | Shell Internationale Research Maatschappij B.V. | Shaped trilobal particles |
US6764755B2 (en) | 2001-12-17 | 2004-07-20 | Advanced Technology Materials, Inc. | Channelized sorbent media, and methods of making same |
FR2834655B1 (fr) | 2002-01-17 | 2004-12-03 | Sicat | COMPOSITES ZEOLITHE/SiC ET LEUR UTILISATION EN CATALYSE |
JP2003210981A (ja) | 2002-01-18 | 2003-07-29 | Iwao Jiki Kogyo Kk | シリカ担体及びその製造方法 |
JP3821223B2 (ja) | 2002-05-24 | 2006-09-13 | 独立行政法人科学技術振興機構 | 金属酸化物ナノチューブ及びその製法 |
MY139580A (en) | 2002-06-07 | 2009-10-30 | Shell Int Research | Shaped catalyst particles for hydrocarbon synthesis |
US7005118B2 (en) | 2002-07-25 | 2006-02-28 | Instituto Mexicano Del Petroleo | Synthetic mesoporous material with radially assembled nanotubes |
EP1386664B1 (en) | 2002-07-31 | 2016-05-11 | Ineos Technologies (Vinyls) Limited | A hollow parallelepiped pellet suitable as carrier of catalysts for selective exothermic reactions |
RU2326734C2 (ru) | 2002-11-04 | 2008-06-20 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Продолговатые формованные частицы, применение в качестве катализатора или носителя катализатора |
WO2004108329A1 (en) | 2003-06-04 | 2004-12-16 | Seco Tools Ab | Method and device for manufacturing a blank for a tool |
KR100715296B1 (ko) | 2003-07-29 | 2007-05-08 | 가부시끼가이샤 도꾸야마 | 중세공성 실리카 미립자 및 그 제조 방법 |
CN1513600A (zh) | 2003-08-19 | 2004-07-21 | 丁章云 | 一种催化剂活性载体及其制备 |
PL380018A1 (pl) | 2003-12-19 | 2006-12-11 | Celanese International Corporation | Warstwowy materiał nośnika do katalizatorów |
TW201236755A (en) | 2003-12-19 | 2012-09-16 | Celanese Int Corp | Halide free precursors for catalysts |
DE102004006113A1 (de) | 2004-02-06 | 2005-08-25 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von Trägern für Katalysatoren |
EP1740060A1 (en) | 2004-04-05 | 2007-01-10 | Danisco A/S | Enzymatic process for acrylamide reduction in foodstuffs |
US7297402B2 (en) | 2004-04-15 | 2007-11-20 | Shell Oil Company | Shaped particle having an asymmetrical cross sectional geometry |
DE102004034039B4 (de) | 2004-07-13 | 2008-04-17 | Technamation Technical Europe Gmbh | Extrusionsverfahren und Extruder für zellulosehaltiges Material |
US7320778B2 (en) | 2004-07-21 | 2008-01-22 | Catacel Corp. | High-performance catalyst support |
JP2008522873A (ja) | 2004-12-09 | 2008-07-03 | コーニング インコーポレイテッド | ハニカム押出ダイの製造 |
MX2007008025A (es) | 2004-12-30 | 2007-09-04 | Grace Gmbh & Co Kg | Cuerpos adsorbentes flexibles. |
JP2006263635A (ja) | 2005-03-25 | 2006-10-05 | Sumitomo Metal Mining Co Ltd | 高比表面積の無機質固化体及びその製造方法 |
DE102005019596A1 (de) | 2005-04-27 | 2006-11-02 | Süd-Chemie AG | Katalysatorträger |
US8318627B2 (en) | 2005-08-10 | 2012-11-27 | Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg | Process for preparation of a catalyst carrier |
TW200719968A (en) | 2005-10-31 | 2007-06-01 | Sued Chemie Ag | Catalyst molding for partial oxidation reactions |
US7761994B2 (en) | 2006-05-17 | 2010-07-27 | Air Products And Chemicals, Inc. | Reactor with expandable structure providing improved heat transfer |
US20080023863A1 (en) | 2006-07-31 | 2008-01-31 | Schlumberger Technology Corporation | Method and apparatus for extrusion of profiled helical tubes |
WO2008019581A1 (fr) | 2006-08-11 | 2008-02-21 | China Petroleum & Chemical Corporation | Alumine ayant une structure poreuse complexe, et catalyseur et procédé d'hydrogénation sélective de l'essence de craquage |
DE102006046538A1 (de) | 2006-09-29 | 2008-04-03 | Vladimir Volchkov | Katalysatorträger und seine Fertigungsverfahren |
TW200902144A (en) | 2006-11-11 | 2009-01-16 | Uop Llc | Oxidation processes using functional surface catalyst composition |
WO2008060974A2 (en) | 2006-11-11 | 2008-05-22 | Uop Llc | Dehydrogenation processes using functional surface catalyst composition |
TW200843846A (en) | 2006-11-11 | 2008-11-16 | Uop Llc | Oxidation processes using functional surface catalyst composition |
TW200836830A (en) | 2006-11-11 | 2008-09-16 | Uop Llc | Hydrogenation processes using functional surface catalyst composition |
TW200843851A (en) | 2006-11-11 | 2008-11-16 | Uop Llc | Hydrogenation Processes Using Functional Surface Catalyst Composition |
WO2008060980A2 (en) | 2006-11-11 | 2008-05-22 | Uop Llc | Oxidation processes using functional surface catalyst composition |
TW200902143A (en) | 2006-11-11 | 2009-01-16 | Uop Llc | Dehydrogenation processes using functional surface catalyst composition |
TW200836829A (en) | 2006-11-11 | 2008-09-16 | Uop Llc | Functional surface catalyst composition |
TW200836831A (en) | 2006-11-11 | 2008-09-16 | Uop Llc | Selective hydrogenation processes using functional surface catalyst composition |
WO2008060993A2 (en) | 2006-11-11 | 2008-05-22 | Uop Llc | Selective hydrogenation processes using functional surface catalyst composition |
TW200843848A (en) | 2006-11-11 | 2008-11-16 | Uop Llc | Hydrogenation processes using functional surface catalyst composition |
EP2086673A2 (en) | 2006-11-11 | 2009-08-12 | Uop Llc | Selective hydrogenation processes using functional surface catalyst composition |
BRPI0718718A2 (pt) | 2006-11-11 | 2013-12-03 | Uop Llc | Composição de catalisador |
WO2008060969A2 (en) | 2006-11-11 | 2008-05-22 | Uop Llc | Dehydrogenation processes using functional surface catalyst composition |
DE102006058800A1 (de) * | 2006-12-13 | 2008-06-19 | Wacker Chemie Ag | Verfahren zur Herstellung von Katalysatoren und deren Verwendung für die Gasphasenoxidation von Olefinen |
CA2714818A1 (en) | 2007-01-18 | 2008-07-24 | Janssen Pharmaceutica Nv | Catalyst, catalyst precursor, catalyst carrier, preparation and use of thereof in fischer-tropsch synthesis |
JP4724796B2 (ja) | 2007-01-25 | 2011-07-13 | 住友化学株式会社 | 成形体およびその製造方法ならびに押出成形機 |
DE102007025444A1 (de) * | 2007-05-31 | 2008-12-11 | Süd-Chemie AG | VAM-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung |
DE102007025442B4 (de) * | 2007-05-31 | 2023-03-02 | Clariant International Ltd. | Verwendung einer Vorrichtung zur Herstellung eines Schalenkatalysators und Schalenkatalysator |
DE102007025362A1 (de) * | 2007-05-31 | 2008-12-11 | Süd-Chemie AG | Dotierter Pd/Au-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung |
CN101376832B (zh) | 2007-08-27 | 2012-09-12 | 中国石油化工股份有限公司 | 一种沸腾床加氢处理催化剂的制备方法 |
CN101376830B (zh) | 2007-08-27 | 2012-06-27 | 中国石油化工股份有限公司 | 一种加氢处理催化剂载体及其制备方法 |
CN101168440B (zh) | 2007-09-27 | 2011-07-20 | 上海交通大学 | 一种二氧化硅介孔材料及其制备方法 |
JP2009190964A (ja) | 2007-10-15 | 2009-08-27 | Ibiden Co Ltd | ハニカム構造体の製造方法 |
CN101224409B (zh) | 2007-10-18 | 2011-06-15 | 烟台博瑞特精细化工有限公司 | 一种高吸附值微粉硅胶生产方法 |
CN101433863B (zh) | 2007-11-15 | 2012-08-29 | 中国石油化工股份有限公司 | 一种复合氧化物载体及其制备方法 |
WO2009071863A2 (fr) | 2007-11-30 | 2009-06-11 | Saint-Gobain Centre De Recherches Et D'etudes Europeen | Poudre nanometrique |
US20100279846A1 (en) | 2007-12-27 | 2010-11-04 | Stephen Dahar | Phase stable metal oxide article and process of making the same |
JP5566881B2 (ja) | 2008-03-26 | 2014-08-06 | 株式会社日本触媒 | エチレンオキシド製造用触媒および該触媒を用いたエチレンオキシドの製造方法 |
FR2931705B1 (fr) | 2008-05-28 | 2010-09-03 | Inst Francais Du Petrole | Catalyseur a base d'un materiau amorphe comprenant du silicium a porosite hierarchisee et organisee et procede ameliore de traitement de charges hydrocarbonees |
FR2931818B1 (fr) | 2008-05-28 | 2012-11-30 | Inst Francais Du Petrole | Procede d'oligomerisation des olefines legeres utilisant un catalyseur a base d'un materiau amorphe a porosite hierarchisee et organisee |
FR2931708B1 (fr) | 2008-05-28 | 2014-03-14 | Inst Francais Du Petrole | Catalyseur a base d'un materiau cristallise a porosite hierarchisee et organisee et son utilisation en oligomerisation des olefines legeres |
JP5816088B2 (ja) | 2008-09-04 | 2015-11-18 | ラムス テクノロジー インク | オレフィン異性化およびメタセシス触媒 |
DE102008042064A1 (de) | 2008-09-12 | 2010-03-18 | Basf Se | Verfahren zur Herstellung von geometrischen Katalysatorformkörpern |
DE102008042061A1 (de) | 2008-09-12 | 2010-03-18 | Basf Se | Verfahren zur Herstellung von geometrischen Katalysatorformkörpern |
DE102008054586A1 (de) | 2008-12-12 | 2010-06-17 | Basf Se | Verfahren zur kontinuierlichen Herstellung von geometrischen Katalysatorformkörpern K |
EP2198958B1 (en) | 2008-12-17 | 2017-11-08 | Clariant Prodotti (Italia) SpA | Catalysts for oxychlorination of ethylene to 1.2-dichloroethane |
ITMI20082333A1 (it) | 2008-12-29 | 2010-06-30 | Sud Chemie Catalysts Italia S R L | Precursori di catalizzatori di ossiclorurazione dell'etilene a dicloroetano. |
CN101767790B (zh) | 2008-12-31 | 2012-01-25 | 中国石油化工股份有限公司 | 一种双孔分布氧化硅的合成方法 |
US8748681B2 (en) | 2009-03-31 | 2014-06-10 | Uop Llc | Process for oligomerizing dilute ethylene |
US20110172088A1 (en) | 2009-04-24 | 2011-07-14 | Uop Llc | Functional Surface Catalyst Composition |
JP2011140210A (ja) | 2009-06-24 | 2011-07-21 | Sumitomo Chemical Co Ltd | 成形体およびその製造方法、並びに触媒およびその製造方法 |
EP2448741A1 (en) | 2009-06-30 | 2012-05-09 | 3M Innovative Properties Company | Extrusion die element, extrusion die and method for making multiple stripe extrudate from multilayer extrudate |
US8647099B2 (en) | 2010-02-26 | 2014-02-11 | Corning Incorporated | Extrudate transport apparatus having a free floating roller assembly |
GB201003549D0 (en) | 2010-03-04 | 2010-04-21 | Johnson Matthey Plc | Sorbents |
JP5667778B2 (ja) | 2010-03-30 | 2015-02-12 | 住友化学株式会社 | 触媒担体の製造方法および触媒担体 |
CN102309998B (zh) | 2010-07-07 | 2013-05-01 | 中国石油化工股份有限公司 | 一种氧化铝载体的制备方法 |
DE102010026462A1 (de) * | 2010-07-08 | 2012-01-12 | Süd-Chemie AG | Verfahren zur Herstellung eines Schalenkatalysators und Schalenkatalysator |
WO2012018598A1 (en) | 2010-07-26 | 2012-02-09 | Waters Technologies Corporation | Superficially porous materials comprising a substantially nonporous core having narrow particle size distribution; process for the preparation thereof; and use thereof for chromatographic separations |
US20120034688A1 (en) | 2010-08-04 | 2012-02-09 | Griffin Stephen E | True nucleic acid amplification |
GB201014950D0 (en) | 2010-09-08 | 2010-10-20 | Johnson Matthey Plc | Catalyst manufacturing method |
CN102397795B (zh) | 2010-09-13 | 2014-03-19 | 中国石油化工股份有限公司 | 环氧乙烷生产用银催化剂的载体、其制备方法、由其制成的银催化剂及其应用 |
JP2012091358A (ja) | 2010-10-26 | 2012-05-17 | Sumitomo Chemical Co Ltd | 押出成形機とこれを用いる成形体の製造方法 |
CN102463141B (zh) | 2010-11-02 | 2015-05-06 | 中国石油化工股份有限公司 | 一种氧化铝载体、其制备方法、由其制成的银催化剂及其应用 |
CN102463142B (zh) | 2010-11-04 | 2013-10-09 | 中国石油化工股份有限公司 | 一种加氢催化剂载体及其制备方法 |
US20120115967A1 (en) | 2010-11-08 | 2012-05-10 | Shell Oil Company | Fischer-tropsch catalysts |
DE102010052126A1 (de) | 2010-11-22 | 2012-05-24 | Süd-Chemie AG | Katalysatorformkörper für durchströmte Festbettreaktoren |
CN102485847B (zh) | 2010-12-03 | 2014-06-04 | 中国石油天然气股份有限公司 | 一种石油蜡加氢精制的方法 |
RU2446878C1 (ru) | 2011-04-11 | 2012-04-10 | Учреждение Российской академии наук Институт катализа им. Г.К. Борескова Сибирского отделения РАН | Катализатор, способ приготовления носителя, способ приготовления катализатора и способ окисления монооксида углерода |
CN202570186U (zh) | 2011-09-30 | 2012-12-05 | 中国石油化工股份有限公司 | 醋酸烯丙酯催化剂的载体 |
JP6392218B2 (ja) | 2012-07-02 | 2018-09-19 | ビーエーエスエフ コーポレーション | 酢酸ビニルモノマーの製造のための方法及び複合触媒 |
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EP3325144A1 (en) | 2018-05-30 |
US20180207619A1 (en) | 2018-07-26 |
RU2722157C1 (ru) | 2020-05-27 |
US20210069679A1 (en) | 2021-03-11 |
CN117138838A (zh) | 2023-12-01 |
CN107847913A (zh) | 2018-03-27 |
JP7066028B2 (ja) | 2022-05-12 |
KR20180023008A (ko) | 2018-03-06 |
SA518390761B1 (ar) | 2022-05-09 |
US20200108370A1 (en) | 2020-04-09 |
JP2021104508A (ja) | 2021-07-26 |
US10864500B2 (en) | 2020-12-15 |
JP2018521850A (ja) | 2018-08-09 |
KR102604873B1 (ko) | 2023-11-23 |
US10525448B2 (en) | 2020-01-07 |
EP3325144A4 (en) | 2019-01-16 |
WO2017015487A1 (en) | 2017-01-26 |
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