JP2008536003A - Mcr含有量の少ない原油生成物の製造方法及び触媒 - Google Patents
Mcr含有量の少ない原油生成物の製造方法及び触媒 Download PDFInfo
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- JP2008536003A JP2008536003A JP2008506576A JP2008506576A JP2008536003A JP 2008536003 A JP2008536003 A JP 2008536003A JP 2008506576 A JP2008506576 A JP 2008506576A JP 2008506576 A JP2008506576 A JP 2008506576A JP 2008536003 A JP2008536003 A JP 2008536003A
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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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- CZDSWLXAULJYPZ-UHFFFAOYSA-J molybdenum(4+);dicarbonate Chemical compound [Mo+4].[O-]C([O-])=O.[O-]C([O-])=O CZDSWLXAULJYPZ-UHFFFAOYSA-J 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
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- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
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- 238000001935 peptisation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
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- 150000008117 polysulfides Polymers 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 239000011275 tar sand Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
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Abstract
【解決手段】原油原料を1種以上の触媒と接触させて原油生成物を含む全生成物を製造する方法。原油生成物は25℃、0.101MPaにおいて液体混合物である。原油生成物のMCR含有量は原油原料のMCR含有量の90%以下である。原油生成物の他の1つ以上の特性を原油原料のそれぞれの特性に比べて10%以上変化できる。
【選択図】図1
Description
本発明は、一般には原油原料(crude feed)を処理するためのシステム、方法及び触媒に関する。更に詳しくは、ここで説明する特定の実施態様は、原油原料を、25℃、0.101MPaにおいて液体混合物であって、原油原料のそれぞれの特性と比べて変化した1種以上の特性を有する原油生成物を含む全生成物に転化するためのシステム、方法、及び触媒に関する。
原油を経済的に輸送できないか、或いは従来の設備を用いて処理できないような不適当な特性を1つ以上有する原油(crude)は、普通、“不利な原油”と言われている。
幾つかの実施態様では、本発明は、ミクロ炭素残留物(MCR)含有量(ASTM法D4530で測定)が原油原料1g当たり0.0001g以上である原油原料を1種以上の触媒と接触させて、25℃、0.101MPaにおいて液体混合物である原油生成物を含む全生成物を製造する工程であって、触媒の少なくとも1種は周期表第6欄の1種以上の金属及び/又は周期表第6欄の1種以上の金属の1種以上の化合物であり、中央値細孔径が110Åを超える細孔サイズ分布を有し、かつ細孔径(ASTM法D4282で測定)が350Å以上の細孔が細孔容積(ASTM法D4282で測定)の10%以下を与える細孔容積を有する該工程、及び原油生成物のMCR含有量が原油原料のMCR含有量に対し90%以下となるように、接触条件を制御する工程を含む原油生成物の製造方法を提供する。
幾つかの実施態様では本発明は、前記実施態様の1つ以上を組合わせて、水素の存在下で接触させる工程も提供する。
更なる実施態様では原油生成物は、ここで説明した方法及びシステムのいずれかにより得られる。
更なる実施態様では、ここで説明した方法及びシステムのいずれかにより輸送用燃料、加熱用燃料、潤滑剤又は化学薬品が得られる。
本発明の利点は、以下の詳細な説明により、更に添付図面を参照して当業者に明らかになろう。
図1は、接触システムの一実施態様の概略図である。
図2A及び2Bは、2つの接触帯を有する接触システムの一実施態様の概略図である。
図3A及び3Bは、3つの接触帯を有する接触システムの一実施態様の概略図である。
図4は、分離帯と接触システムとを組合わせた一実施態様の概略図である。
図5は、配合帯と接触システムとを組合わせた一実施態様の概略図である。
図6は、分離帯と接触システムと配合帯とを組合わせた一実施態様の概略図である。
前記課題は、ここで説明したシステム、方法及び触媒を用いて対応できる。例えば原油原料のMCR含有量及び/又は窒素含有量に比べてMCR含有量及び/又は窒素含有量の少ない原油生成物は、原油原料を、中央値細孔径が110Åを超える細孔サイズ分布を有し、かつ細孔径が350Å以上の細孔が細孔容積の10%以下を与える細孔容積を有する触媒と接触させて製造される。原油原料の窒素含有量に比べて窒素含有量の少ない原油生成物は、原油原料を未焼成触媒と接触させて製造される。原油原料の有機酸金属塩中の金属含有量に比べて有機酸金属塩中の金属含有量の少ない原油生成物は、原油原料を、第5〜10欄金属及びθ−アルミナを含む触媒と接触させて製造される。原油原料のMCR含有量に比べてMCR含有量の少ない原油生成物は、原油原料を正味(bulk)金属触媒と接触させて製造される。
“ASTM”とは、American Standard Testing and Materialsを言う。
“API比重”とは、15.5℃(60°F)でのAPI比重を言う。API比重はASTM法D6822で測定する。
原油原料及び原油生成物の水素原子%及び炭素%は、ASTM法D5291で測定する。
“バインダー”とは、小粒子と組合わせて、これより大きい物質(例えばブロック又はペレット)を形成する基質を言う。
“正味金属触媒”とは、少なくとも1種の金属を含む触媒を言い、担体又は支持体を必要としない。
“第X欄金属”とは、周期表第X欄の1種以上の金属及び/又は周期表第X欄の1種以上の金属の1種以上の化合物を言う。ここで第X欄は周期表の欄番号(例えば1〜12)に相当する。例えば“第6欄金属”とは、周期表第6欄の1種以上の金属及び/又は周期表第6欄の1種以上の金属の1種以上の化合物を言う。
“原油原料/全生成物混合物”とは、処理中、触媒を接触させる混合物を言う。
“蒸留物”とは、0.101MPaにおいて204℃(400°F)〜343℃(650°F)の沸点範囲分布を有する炭化水素を言う。蒸留物含有量はASTM法D5307で測定する。
“LHSV”とは、触媒の全容積当たり液体供給原料の容積割合(速度)を言い、時間(h−1)で表す。触媒の全容積は、ここで説明した接触帯中の全ての触媒の容積を合計して算出する。
“周期表”とは、International Union of Pure and Applied Chemistry(IUPAC)で2003年11月に規定された周期表を言う。
“ナフサ”とは、0.101MPaにおいて38℃(100°F)〜200℃(392°F)の沸点範囲分布を有する炭化水素を言う。ナフサ含有量は、ASTM法D5307で測定する。
“Ni/V/Fe含有量”とは、ニッケル、バナジウム、鉄、又はそれらの組合わせの含有量を言う。Ni/V/Fe含有量はASTM法D5708で測定する。
“Nm3/m3 ”とは、原油原料1m3当たりガスの標準m3を言う。
“非凝縮性ガス”とは、STPにおいてガスである成分及び/又は成分の混合物を言う。
平均細孔径=(40,000×合計細孔容積cm3/g)/(表面積m2/g)
“SCFB”とは、原油原料1バレル当たりガスの標準立方フィートを言う。
触媒の“表面積”は、ASTM法D3663で測定する。
“VGO”とは、沸点範囲分布が0.101MPaにおいて343℃(650°F)〜538℃(1000°F)の炭化水素を言う。VGO含有量はASTM法D5307で測定する。
“粘度”とは、37.8℃(100°F)での動粘度を言う。粘度はASTM法D445で測定する。
原油は、炭化水素含有配合物から製造及び/又は乾留(retort)し、次いで安定化してよい。原油は、一般に固体、半固体、及び/又は液体である。原油は生原油(crude oil)を含有してよい。安定化法としては、限定されるものではないが、原油から非凝縮性ガス、水、塩、固体又はそれらの組合わせを除去して、安定化原油を形成する方法が挙げられる。このような安定化は、多くの場合、製造及び/又は乾留場所又はその近辺で行ってよい。
図2及び図3は、2つ又は3つの接触帯を有する接触システム100の実施態様の概略図である。図2A、2Bにおいて、接触システム100は上流接触帯102及び下流接触帯114を有する。図3A、3Bでは、接触帯102、114、116を有する。図2A、3Aでは、接触帯102、114、116は一反応器中で別々の接触帯として示す。原油原料は原油原料導管104経由で上流接触帯102に入る。
特定の実施態様では原油生成物における有機酸金属塩中のアルカリ金属及びアルカリ土類金属の含有量は、原油原料における有機酸金属塩中のアルカリ金属及びアルカリ土類金属の含有量は、原油生成物1g当たり約1×10−7〜約5×10−5g、約5×10−7〜約1×10−5g、又は約1×10−6〜約5×10−6gの範囲である。
幾つかの実施態様では原油生成物は、ナフサを原油生成物1g当たり0.001g以上又は0.01g以上含有してよい。他の実施態様では原油生成物は、ナフサを原油生成物1g当たり0.6g以下又は0.8g以下の含有量で含有してよい。
特定の実施態様では原油生成物のVGO含有量は、原油生成物1g当たり約0.00001〜約0.8g、約0.001〜約0.5g、約0.005〜約0.4g、又は約0.01〜約0.3gの範囲である。
担持触媒は、一般に公知の触媒製造法を用いて製造される。触媒製造法の例は、Gabrielov等のUSP 6,218,333、Gabrielov等のUSP 6,290,841、Boon等のUSP 5,744,025、及びBhan等の米国特許出願公告No.2003/0111391に記載されている。
幾つかの実施態様では金属溶液は、鉱酸及び/又は有機酸を用いてpH3以下の所望のpHに調節してよい。鉱酸としては、限定されるものではないが、燐酸、硝酸、硫酸又はそれらの混合物が挙げられる。
第一触媒、第二触媒、第三触媒、第四触媒及び第五触媒の他の実施態様は、特にここで説明したように、作る、及び/又は使用してよい。
ここで説明した触媒は、原油原料/全生成物混合物の安定性を維持しながら、及び/又は触媒の寿命を維持しながら、MCR含有量低下、及び/又は高温高圧での粘度低下を容易にする可能性が或る。
アルミナ/シリカ混合物550g、焼成アルミナ微粉26g、水585g及び16M硝酸8gを35分間、磨砕してアルミナ/シリカ支持体を製造した。このアルミナ/シリカ混合物は、支持体1g当たり、アルミナ/シリカ混合物(Criterion Catalysts and Technologies LP)0.98g以上を、アルミナ/シリカ混合物1g当たりシリカ(Criterion Catalysts and Technologies LP)0.02g以下と配合して、製造した。得られた磨砕混合物を、直径1.94mm及び3.28mmのダイプレートで押し出し、次いで強熱減量が初期押出物に対し27〜30重量%になるまで93℃(200°F)〜121℃(250°F)の範囲の温度で熱処理した。強熱減量は、押出物を540℃で15〜50分加熱した後、押出物の相対重量損失量を測定して行なった。押出物を更に918℃(1685°F)で1時間熱処理した。支持体の平均細孔径は125Å、表面積は281m2/g、細孔容積は0.875cm3/g、また細孔は支持体の合計細孔容積の0.9%を与える直径350Å以上の細孔であった。例1は、90Å以上の平均細孔径を有すると共に、細孔径350Å以上の細孔が支持体の細孔容積の15%以下を与える細孔容積を有する支持体の製造例を示す。
次のようにして触媒を製造した。例1に記載の方法で製造したアルミナ/シリカ支持体を、以下のようにして製造したモリブデン/ニッケル/燐含浸溶液に含浸した。(NH4)2Mo2O7 62.34g、MoO3 17.49g、30%H2O2 12.22g、及び脱イオン水50.47gを配合してスラリーを形成し、第一溶液を作った。このスラリーにMEA(3.0g)を、溶解熱を制御するのに充分な速度で加えた。固体が溶解するまでスラリーを64℃(147°F)に加熱した後、室温に冷却した。第一溶液のpHは5.34であった。
例2は、中央値細孔径が110Åを超える細孔サイズ分布を有すると共に、細孔径が350Å以上の細孔が合計細孔容積の10%以下を与える細孔容積を有する第6欄金属触媒の製造法を示す。また本例は、90Å以上の平均細孔径を有すると共に、細孔径が350Å以上の細孔が合計細孔容積の15%以下を与える細孔容積を有する支持体から第6欄金属触媒を製造する方法も示す。
中央にサーモウエルを配置した管状反応器にサーモカップルを備えて触媒床中の温度を測定した。触媒床は、反応器のサーモウエルと内壁間の空間に触媒及び炭化珪素(20−グリッド、Stanford Materials、カナダのAliso Viejo)を充填して形成した。このような炭化珪素は、ここで説明した処理条件下では触媒特性があっても、低いと考えられる。全ての触媒を等容量の炭化珪素とブレンドしてから、この混合物を反応器の接触帯部に入れた。
アルミナ粉末(Criterion Catalysts and Technologies LP)550g、焼成アルミナ微粉26g、水585g及び16M硝酸8gを35分間、磨砕してアルミナ支持体を製造した。この磨砕混合物を、直径1.94mm及び3.28mmのダイプレートで押し出し、次いで強熱減量が初期押出物に対し27〜30重量%になるまで93℃(200°F),107℃(225°F)〜121℃(250°F)の範囲の温度で熱処理した。強熱減量は、例1に記載したように行なった。押出物を更に918℃(1685°F)で1時間熱処理した。支持体は、平均細孔径が186.4Å、細孔容積が0.868m3/ml、また支持体の合計細孔容積の13.3%を与える細孔径350Å以上の細孔を有していた。例4は、90Å以上の平均細孔径を有すると共に、細孔径350Å以上の細孔が支持体の細孔容積の15%以下を与える細孔容積を有する支持体の製造例を示す。
例4に記載の方法で製造したアルミナ支持体を、以下のようにして製造したモリブデン/コバルト/燐含浸溶液に含浸した。MoO3(22.95g)を85重量%H3PO4(12.67g)と配合し、82℃(180°F)に加熱してモリブデン/燐溶液を形成した。このモリブデン/燐溶液にCo(OH)2(29.83g)を加え、得られたモリブデン/コバルト/燐溶液を100℃に加熱した。このモリブデン/コバルト/燐溶液にクエン酸モノハイドレート(21.5g)を加え、100℃に加熱し、この温度で1時間維持した。得られた溶液の容積を252mlに減らして、モリブデン/コバルト/燐含浸溶液を製造した。含浸溶液のpHは3.22であった。
例5は、中央値細孔径が110Åを超える細孔サイズ分布を有すると共に、細孔径が350Å以上の細孔が合計細孔容積の10%以下を与える細孔容積を有する第6欄金属触媒の製造法を示す。また本例は、90Å以上の平均細孔径を有すると共に、細孔径が350Å以上の細孔が合計細孔容積の15%以上を与える細孔容積を有する支持体から第6欄金属触媒を製造する方法も示す。
反応装置(接触帯の内容物は除く)、原油原料、触媒の硫化方法、全生成物の分離方法、接触条件、接触時間、及び原油生成物は、例3に記載のものと同じである。
第4表に原油生成物の特性をまとめた。
101 原油原料供給部
102 上流接触帯
104 原油供給導管
106 ガス導管
108 下流分離帯
112 原油生成物導管
114 下流接触帯
116 追加の下流接触帯
120 上流分離帯
122 原油導管
124 分離帯
126 追加の原油原料導管
130 配合帯
132 流れ導管
134 ブレンド導管
140 配合帯
148 接触システム
Claims (24)
- ミクロ炭素残留物(MCR)含有量(ASTM法D4530で測定)が原油原料1g当たり0.0001g以上である原油原料を1種以上の触媒と接触させて、25℃、0.101MPaにおいて液体混合物である原油生成物を含む全生成物を製造する工程であって、触媒の少なくとも1種は周期表第6欄の1種以上の金属及び/又は周期表第6欄の1種以上の金属の1種以上の化合物であり、中央値細孔径が110Åを超える細孔サイズ分布を有し、かつ細孔径(ASTM法D4282で測定)が350Å以上の細孔が細孔容積(ASTM法D4282で測定)の10%以下を与える細孔容積を有する該工程、及び
原油生成物のMCR含有量が原油原料のMCR含有量に対し90%以下となるように、温度、圧力、水素源の流れ、原油原料流又はそれらの組合わせからなる接触条件を制御する工程、
を含む原油生成物の製造方法。 - 原油生成物のMCR含有量が原油原料のMCR含有量に対し80%以下、50%以下、30%以下、又は10%以下である請求項1に記載の方法。
- 原油原料のMCR含有量が、原油原料1g当たり0.0001〜0.5g、0.005〜0.1g、又は0.01〜0.05gである請求項1又は2に記載の方法。
- 第6欄金属触媒が、周期表第7〜10欄の1種以上の金属及び/又は周期表第7〜10欄の1種以上の金属の1種以上の化合物を更に含む請求項1〜3のいずれか1項に記載の方法。
- 第6欄金属触媒が、周期表第10欄の1種以上の金属及び/又は周期表第10欄の1種以上の金属の1種以上の化合物を更に含む請求項1〜4のいずれか1項に記載の方法。
- 第6欄金属触媒が、周期表第15欄の1種以上の元素及び/又は周期表第15欄の1種以上の元素の1種以上の化合物を更に含む請求項1〜5のいずれか1項に記載の方法。
- 第6欄金属触媒が、更に支持体を含み、該支持体がγ−アルミナを、支持体1g当たり0.8g以上、0.9g以上、又は0.95g以上含む請求項1〜6のいずれか1項に記載の方法。
- 接触が水素源の存在下で行なわれ、水素源の流れの接触条件が、原油生成物を製造するため、制御される請求項1〜7のいずれか1項に記載の方法。
- 接触中の原油原料/全生成物混合物のP値が1.5以上である請求項1〜8のいずれか1項に記載の方法。
- 原油生成物を原油原料と同じか又は異なる原油と配合してブレンドを形成する工程を更に含む請求項1〜9のいずれか1項に記載の方法。
- 前記原油生成物又はブレンドを処理して、輸送用燃料、加熱用燃料、潤滑剤又は化学薬品を製造する工程を更に含む請求項1〜10のいずれか1項に記載の方法。
- 支持体と、周期表第6欄の1種以上の金属、及び/又は周期表第6欄の1種以上の金属の1種以上の化合物とを含む触媒であって、中央値細孔径が110Åを超える細孔サイズ分布を有し、かつ細孔径(ASTM法D4282で測定)が350Å以上の細孔が細孔容積(ASTM法D4282で測定)の10%以下を与える細孔容積を有する該触媒。
- 支持体が、γ−アルミナを、支持体1g当たり0.8g以上、0.9g以上、又は0.95g以上更に含む請求項12に記載の触媒。
- 支持体は、平均細孔径が90Å以上の細孔サイズ分布を有し、かつ細孔径(ASTM法D4282で測定)が350Å以上の細孔が細孔容積(ASTM法D4282で測定)の15%以下を与える細孔容積を有する請求項12又は13に記載の触媒。
- 周期表第15欄の1種以上の元素及び/又は周期表第15欄の1種以上の元素の1種以上の化合物を更に含む請求項12〜14のいずれか1項に記載の触媒。
- 周期表第5欄の1種以上の金属及び/又は周期表第5欄の1種以上の金属の1種以上の化合物を、第5欄金属の合計重量として計算して、触媒1g当たり0.001g以下更に含む請求項12〜15のいずれか1項に記載の触媒。
- 90Å以上の平均細孔径を有し、かつ細孔径(ASTM法D4282で測定)が350Å以上の細孔が細孔容積(ASTM法D4282で測定)の15%以下を与える細孔容積を有する支持体に、周期表第6欄の1種以上の金属及び/又は周期表第6欄の1種以上の金属の1種以上の化合物を含む溶液を配合することを特徴とする触媒の製造方法。
- 前記金属溶液のpHが3以下である請求項17に記載の方法。
- 前記金属溶液が、周期表第7〜10欄の1種以上の金属及び/又は周期表第7〜10欄の1種以上の金属の少なくとも1種の化合物を更に含む請求項17又は18に記載の方法。
- 前記金属溶液が、周期表第15欄の1種以上の元素及び/又は1種以上の周期表第15欄元素の1種以上の化合物を更に含む請求項17〜19のいずれか1項に記載の方法。
- 前記金属溶液が1種以上の鉱酸を更に含む請求項17〜20のいずれか1項に記載の方法。
- 前記金属溶液が1種以上の有機酸成分を更に含む請求項17〜21のいずれか1項に記載の方法。
- 前記金属溶液が過酸化水素を更に含む請求項17〜22のいずれか1項に記載の方法。
- 前記金属溶液がアミンを更に含む請求項17〜23のいずれか1項に記載の方法。
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- 2006-04-07 CA CA2604012A patent/CA2604012C/en not_active Expired - Fee Related
- 2006-04-07 BR BRPI0610670A patent/BRPI0610670B1/pt not_active IP Right Cessation
- 2006-04-07 WO PCT/US2006/013328 patent/WO2006110660A1/en active Application Filing
- 2006-04-07 RU RU2007141710/04A patent/RU2424275C2/ru not_active IP Right Cessation
- 2006-04-07 US US11/400,542 patent/US7918992B2/en not_active Expired - Fee Related
- 2006-04-07 CN CN200680014647.3A patent/CN101166808B/zh not_active Expired - Fee Related
- 2006-04-11 NL NL2000050A patent/NL2000050C2/nl not_active IP Right Cessation
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JP2015506829A (ja) * | 2011-12-21 | 2015-03-05 | イエフペ エネルジ ヌヴェルIfp Energies Nouvelles | 少なくとも1種の有機添加剤を用いて調製される、第viii族金属をベースとする触媒の調製方法、および前記触媒を用いる選択的水素化方法 |
Also Published As
Publication number | Publication date |
---|---|
BRPI0610670B1 (pt) | 2016-01-19 |
NL2000050C2 (nl) | 2007-07-27 |
CN101166808B (zh) | 2013-03-27 |
RU2424275C2 (ru) | 2011-07-20 |
US7918992B2 (en) | 2011-04-05 |
US20110160044A1 (en) | 2011-06-30 |
US8481450B2 (en) | 2013-07-09 |
CA2604012C (en) | 2013-11-19 |
JP2013067808A (ja) | 2013-04-18 |
BRPI0610670A2 (pt) | 2012-10-30 |
NO20075770L (no) | 2007-11-09 |
US20060231465A1 (en) | 2006-10-19 |
WO2006110660A1 (en) | 2006-10-19 |
EP1874897A1 (en) | 2008-01-09 |
RU2007141710A (ru) | 2009-05-20 |
CN101166808A (zh) | 2008-04-23 |
CA2604012A1 (en) | 2006-10-19 |
NL2000050A1 (nl) | 2006-10-12 |
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