JP4395369B2 - 水添および脱水素方法そしてそれら用の触媒 - Google Patents
水添および脱水素方法そしてそれら用の触媒 Download PDFInfo
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- JP4395369B2 JP4395369B2 JP2003514067A JP2003514067A JP4395369B2 JP 4395369 B2 JP4395369 B2 JP 4395369B2 JP 2003514067 A JP2003514067 A JP 2003514067A JP 2003514067 A JP2003514067 A JP 2003514067A JP 4395369 B2 JP4395369 B2 JP 4395369B2
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Classifications
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- 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
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/16—Clays or other mineral silicates
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- 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
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
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- C—CHEMISTRY; METALLURGY
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- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/44—Hydrogenation of the aromatic hydrocarbons
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
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Description
商品名Promaxon Dの下で商業的に入手可能な結晶性水和ケイ酸カルシウムの押出し加工品に乾燥を500℃の温度で3時間受けさせた。次に、湿式含浸(wet impregnation)技術を用いて、前記乾燥させた支持体に塩化パラジウム(PdCl2)の溶液を染み込ませた。詳細には、65.38gの乾燥させたPromaxon Dを38.23モルの塩化パラジウム水溶液に徐々に接触させたが、前記溶液の量を、この量が前記乾燥させたPromaxon Dの推定吸収容量に相当するように選択した。前記パラジウム塩の量を結果として生じる触媒に含まれる最終的パラジウム含有量が0.3重量%になるように計算した。前記含浸を受けさせた固体に乾燥を真空下25℃で36時間の後に乾燥を110℃の温度で16時間受けさせた。最後に、この触媒に焼成を400℃の温度で3時間受けさせた。
熱分解ガソリンの選択的水添
前記活性化を受けさせた触媒(これはゾノトライトである担体に0.3重量%担持されているPdを含んで成る)を42.2g(75mlの体積を有する)の量で実験室規模の連続細流床(trickle bed)反応槽の中に窒素下で移した。次に、前記触媒に還元を120℃で流れる水素流下で受けさせた。その後、水蒸気分解装置から得た熱分解ガソリン(表2に示す組成および特性を有する)を前記反応槽の中に4.92時−1のLHSV[7.00時−1の時間当たりの重量空間速度(WHSV)に相当(296g/時の質量流量になる)]で通し、それと一緒に水素を40.0Nl/時の流量で通した。水素/ジエンのモル比は4.10であった。その全圧を30バールにし、そして入り口温度を約45℃から約120℃で変えた。
Claims (17)
- 石油化学原料の中の、三重結合を有するアルキン、二重結合を2つ有するジオレフィン、二重結合を2つ以上有するマルチプルオレフィン、二重結合を1つ有する不飽和炭化水素、および芳香核を有する芳香族不飽和炭化水素から選択される不飽和、に水添を受けさせる方法であって、不飽和を有する少なくとも1種の成分を含有する石油化学原料および水素を少なくとも30m2/gの表面積を有していて10から200ミクロンの平均直径を有する実質的に球形の粒子の形態でありかつ前記粒子の中の孔が100から2000オングストロームの直径を有する結晶性ケイ酸カルシウムである支持体に担持されているVIII族の少なくとも1種の金属を含んで成る触媒に3から150バールの圧力下0から550℃の温度で接触させることを含んで成る方法。
- 前記ケイ酸カルシウムが化学組成Ca6Si6O17(OH)2で表される請求項1記載の方法。
- 前記支持体が7.5より高いpHに相当する塩基度を示す請求項1〜2のいずれか記載の方法。
- 前記VIII族の金属がパラジウムを含んで成っていて前記パラジウムが前記支持体に支持型触媒の重量を基準にして0.01から10重量%の量で染み込んでいる請求項1〜3のいずれか記載の方法。
- 前記石油化学原料を前記触媒の上に0.1から100時-1の時間当たりの液体空間速度で通す請求項1〜4のいずれか記載の方法。
- 水添を受けさせる不飽和を有する前記少なくとも1種の成分に対する水素のモル比を0.7から200にする請求項1〜5のいずれか記載の方法。
- 水添を受けさせる不飽和を有する前記少なくとも1種の成分がC4流れの中に入っているブタジエンを含んで成る請求項1〜6のいずれか記載の方法。
- 水添を受けさせる不飽和を有する前記少なくとも1種の成分がC4流れの中に入っているビニルアセチレンおよびエチルアセチレンの中の少なくとも1種を含んで成る請求項1から6のいずれか1項記載の方法。
- 前記C4流れがFCC装置、ビスブレーカー、コーカーまたは水蒸気分解装置に由来する請求項7または請求項8記載の方法。
- 水添を受けさせる不飽和を有する前記少なくとも1種の成分がC3流れの中に入っているメチルアセチレンおよびプロパジエンの中の少なくとも1種を含んで成る請求項1から6のいずれか1項記載の方法。
- 前記C3流れが水蒸気分解装置に由来する請求項10記載の方法。
- 水添を受けさせる不飽和を有する前記少なくとも1種の成分が熱分解ガソリンの中に入っているジオレフィンおよび不飽和芳香族の中の少なくとも1種を含んで成る請求項1から6のいずれか1項記載の方法。
- 水添を受けさせる不飽和を有する前記少なくとも1種の成分が熱分解ガソリンの中に入っているジエンおよびアセチレンの中の少なくとも1種を含んで成る請求項1から6のいずれか1項記載の方法。
- 前記熱分解ガソリンが水蒸気分解装置、コーカー装置またはビスブレーカーに由来するか或はFCC装置に由来する分解を受けた軽質ナフサを含んで成る請求項12または請求項13記載の方法。
- 水添を受けさせる不飽和を有する前記少なくとも1種の成分がスチレン流れの中に入っているフェニルアセチレンを含んで成る請求項1から6のいずれか1項記載の方法。
- 水添を受けさせる不飽和を有する前記少なくとも1種の成分が芳香族が豊富な溜分の中に入っているオレフィンを含んで成る請求項1から6のいずれか1項記載の方法。
- 前記芳香族溜分が改質装置、コーカーまたは水蒸気分解装置に由来する請求項16記載の方法。
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EP01202732A EP1277826A1 (en) | 2001-07-18 | 2001-07-18 | Hydrogenation and dehydrogenation processes and catalysts therefor |
PCT/EP2002/007947 WO2003008519A1 (en) | 2001-07-18 | 2002-07-16 | Hydrogenation and dehydrogenation processes and catalysts therefor |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11584700B2 (en) | 2019-02-28 | 2023-02-21 | Dow Global Technologies Llc | Methods for operating acetylene hydrogenation units in olefin production processes |
Families Citing this family (105)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004021128A1 (de) * | 2004-04-29 | 2005-11-24 | Oxeno Olefinchemie Gmbh | Vorrichtung und Verfahren für die kontinuierliche Umsetzung einer Flüssigkeit mit einem Gas an einem festen Katalysator |
JP4845172B2 (ja) * | 2005-03-30 | 2011-12-28 | 月島機械株式会社 | 有機化合物の断熱冷却式晶析方法及び装置 |
JP4765382B2 (ja) * | 2005-04-18 | 2011-09-07 | トヨタ自動車株式会社 | 耐熱性を備えた複合酸化物の製法 |
JP4835027B2 (ja) * | 2005-04-18 | 2011-12-14 | トヨタ自動車株式会社 | 複合体の製法 |
JP4765381B2 (ja) * | 2005-04-18 | 2011-09-07 | トヨタ自動車株式会社 | 耐熱性を備えた複合酸化物の製法 |
US7655595B2 (en) * | 2006-06-02 | 2010-02-02 | United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Sol-gel based oxidation catalyst and coating system using same |
TW200848158A (en) * | 2006-11-11 | 2008-12-16 | Uop Llc | Dehydrogenation processes using functional surface catalyst composition |
WO2008060971A2 (en) * | 2006-11-11 | 2008-05-22 | Uop Llc | Dehydrogenation processes using functional surface catalyst composition |
WO2008060974A2 (en) * | 2006-11-11 | 2008-05-22 | Uop Llc | Dehydrogenation processes using functional surface catalyst composition |
WO2008140025A1 (ja) * | 2007-05-08 | 2008-11-20 | Kabushiki Kaisha Toyota Chuo Kenkyusho | 排ガス浄化用触媒、それを用いた排ガス浄化装置及び排ガス浄化方法 |
CN101220294B (zh) * | 2007-12-14 | 2013-01-23 | 武汉科技学院 | 润滑油基础油脱酸剂及其使用方法 |
US8268604B2 (en) | 2007-12-20 | 2012-09-18 | Abbott Point Of Care Inc. | Compositions for forming immobilized biological layers for sensing |
US8241697B2 (en) | 2007-12-20 | 2012-08-14 | Abbott Point Of Care Inc. | Formation of immobilized biological layers for sensing |
EP2082802A1 (en) * | 2008-01-25 | 2009-07-29 | Total Petrochemicals Research Feluy | Process for obtaining a catalyst composite |
EP2082803A1 (en) * | 2008-01-25 | 2009-07-29 | Total Petrochemicals Research Feluy | Process for obtaining catalyst composites comprising MeAPO and their use in conversion of organics to olefins |
US8101541B2 (en) * | 2008-07-14 | 2012-01-24 | Sud-Chemie Inc. | Catalyst for dehydrogenation of hydrocarbons |
WO2010013353A1 (en) * | 2008-07-29 | 2010-02-04 | Toyota Jidosha Kabushiki Kaisha | Method for preparing fuel cell electrode catalyst and solid polymer fuel cell |
US7608744B1 (en) | 2008-07-31 | 2009-10-27 | Celanese International Corporation | Ethanol production from acetic acid utilizing a cobalt catalyst |
US8304586B2 (en) | 2010-02-02 | 2012-11-06 | Celanese International Corporation | Process for purifying ethanol |
US8637714B2 (en) | 2008-07-31 | 2014-01-28 | Celanese International Corporation | Process for producing ethanol over catalysts containing platinum and palladium |
US7863489B2 (en) | 2008-07-31 | 2011-01-04 | Celanese International Corporation | Direct and selective production of ethanol from acetic acid utilizing a platinum/tin catalyst |
US8309773B2 (en) | 2010-02-02 | 2012-11-13 | Calanese International Corporation | Process for recovering ethanol |
US8501652B2 (en) | 2008-07-31 | 2013-08-06 | Celanese International Corporation | Catalysts for making ethanol from acetic acid |
US7816565B2 (en) | 2008-07-31 | 2010-10-19 | Celanese International Corporation | Direct and selective production of acetaldehyde from acetic acid utilizing a supported metal catalyst |
US8471075B2 (en) | 2008-07-31 | 2013-06-25 | Celanese International Corporation | Processes for making ethanol from acetic acid |
US8338650B2 (en) | 2008-07-31 | 2012-12-25 | Celanese International Corporation | Palladium catalysts for making ethanol from acetic acid |
US8309772B2 (en) | 2008-07-31 | 2012-11-13 | Celanese International Corporation | Tunable catalyst gas phase hydrogenation of carboxylic acids |
US8680317B2 (en) | 2008-07-31 | 2014-03-25 | Celanese International Corporation | Processes for making ethyl acetate from acetic acid |
US8546622B2 (en) | 2008-07-31 | 2013-10-01 | Celanese International Corporation | Process for making ethanol from acetic acid using acidic catalysts |
CN101658790B (zh) * | 2008-08-28 | 2013-06-12 | 北京三聚环保新材料股份有限公司 | 一种脱氢催化剂的制备方法 |
US20100152507A1 (en) * | 2008-12-16 | 2010-06-17 | Gajda Gregory J | Process for Using Layered Sphere Catalysts with High Accessibility Indexes |
EP2204235A1 (en) * | 2008-12-19 | 2010-07-07 | Total Petrochemicals Research Feluy | Catalyst and process for selective hydrogenation of alkynes and dienes |
EP2204236A1 (en) * | 2008-12-19 | 2010-07-07 | Total Petrochemicals Research Feluy | Catalyst and process for hydrogenation of hydrocarbon feedstocks |
US8178715B2 (en) | 2008-12-31 | 2012-05-15 | Celanese International Corporation | Integrated process for the production of vinyl acetate from acetic acid via acetaldehyde |
EP2223987A1 (en) * | 2009-02-17 | 2010-09-01 | ISP Marl GmbH | Purification of an aromatic fraction containing acetylenes by selective hydrogenation of the acetylenes |
RU2543717C2 (ru) * | 2009-06-11 | 2015-03-10 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ селективного гидрирования и гидрообессеривания пиролизного бензина как исходного материала |
US8450535B2 (en) | 2009-07-20 | 2013-05-28 | Celanese International Corporation | Ethanol production from acetic acid utilizing a cobalt catalyst |
US9192916B2 (en) * | 2009-09-21 | 2015-11-24 | Uop Llc | Selective hydrogenation of dienes in the manufacture of MLAB |
WO2011056248A2 (en) * | 2009-10-26 | 2011-05-12 | Celanese International Corporation | Processes for making ethanol or ethyl acetate from acetic acid using bimetallic catalysts |
US8710277B2 (en) | 2009-10-26 | 2014-04-29 | Celanese International Corporation | Process for making diethyl ether from acetic acid |
US8680321B2 (en) | 2009-10-26 | 2014-03-25 | Celanese International Corporation | Processes for making ethanol from acetic acid using bimetallic catalysts |
EP2493606A2 (en) * | 2009-10-26 | 2012-09-05 | Celanese International Corporation | Catalysts for making ethanol from acetic acid |
RU2549893C2 (ru) * | 2009-10-26 | 2015-05-10 | Селаниз Интернэшнл Корпорейшн | Катализатор для производства этанола путем гидрогенизации уксусной кислоты, содержащий платину-олово на кремнеземной подложке |
EP2336272A1 (en) * | 2009-12-15 | 2011-06-22 | Total Petrochemicals Research Feluy | Debottlenecking of a steam cracker unit to enhance propylene production. |
JP5966244B2 (ja) * | 2009-12-25 | 2016-08-10 | 東ソー株式会社 | 水素化触媒とその製造方法、及びその用途 |
CN102665900B (zh) * | 2009-12-25 | 2015-03-04 | 东曹株式会社 | 氢化催化剂和其制造方法、以及其用途 |
US8211821B2 (en) | 2010-02-01 | 2012-07-03 | Celanese International Corporation | Processes for making tin-containing catalysts |
US8541633B2 (en) | 2010-02-02 | 2013-09-24 | Celanese International Corporation | Processes for producing anhydrous ethanol compositions |
US8858659B2 (en) | 2010-02-02 | 2014-10-14 | Celanese International Corporation | Processes for producing denatured ethanol |
JP2013518705A (ja) | 2010-02-02 | 2013-05-23 | セラニーズ・インターナショナル・コーポレーション | 結晶質担体変性剤を含むエタノール製造用触媒の製造及び使用 |
US8344186B2 (en) | 2010-02-02 | 2013-01-01 | Celanese International Corporation | Processes for producing ethanol from acetaldehyde |
US8932372B2 (en) | 2010-02-02 | 2015-01-13 | Celanese International Corporation | Integrated process for producing alcohols from a mixed acid feed |
US8460405B2 (en) | 2010-02-02 | 2013-06-11 | Celanese International Corporation | Ethanol compositions |
US8747492B2 (en) | 2010-02-02 | 2014-06-10 | Celanese International Corporation | Ethanol/fuel blends for use as motor fuels |
US8668750B2 (en) | 2010-02-02 | 2014-03-11 | Celanese International Corporation | Denatured fuel ethanol compositions for blending with gasoline or diesel fuel for use as motor fuels |
US8728179B2 (en) | 2010-02-02 | 2014-05-20 | Celanese International Corporation | Ethanol compositions |
US8575403B2 (en) | 2010-05-07 | 2013-11-05 | Celanese International Corporation | Hydrolysis of ethyl acetate in ethanol separation process |
US8222466B2 (en) | 2010-02-02 | 2012-07-17 | Celanese International Corporation | Process for producing a water stream from ethanol production |
US8314272B2 (en) | 2010-02-02 | 2012-11-20 | Celanese International Corporation | Process for recovering ethanol with vapor separation |
US8680343B2 (en) | 2010-02-02 | 2014-03-25 | Celanese International Corporation | Process for purifying ethanol |
US8293952B2 (en) * | 2010-03-31 | 2012-10-23 | Exxonmobil Research And Engineering Company | Methods for producing pyrolysis products |
US8680342B2 (en) | 2010-05-07 | 2014-03-25 | Celanese International Corporation | Process for recovering alcohol produced by hydrogenating an acetic acid feed stream comprising water |
US8569551B2 (en) | 2010-05-07 | 2013-10-29 | Celanese International Corporation | Alcohol production process integrating acetic acid feed stream comprising water from carbonylation process |
US8754267B2 (en) | 2010-05-07 | 2014-06-17 | Celanese International Corporation | Process for separating acetaldehyde from ethanol-containing mixtures |
US8704008B2 (en) | 2010-07-09 | 2014-04-22 | Celanese International Corporation | Process for producing ethanol using a stacked bed reactor |
US9272970B2 (en) | 2010-07-09 | 2016-03-01 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
US8664454B2 (en) | 2010-07-09 | 2014-03-04 | Celanese International Corporation | Process for production of ethanol using a mixed feed using copper containing catalyst |
CA2800319A1 (en) | 2010-07-09 | 2012-01-12 | Celanese International Corporation | Finishing reactor for purifying ethanol |
US8710279B2 (en) | 2010-07-09 | 2014-04-29 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
CN102477111B (zh) * | 2010-11-30 | 2013-08-14 | 中国石油化工股份有限公司 | 聚合物加氢方法 |
US8350098B2 (en) | 2011-04-04 | 2013-01-08 | Celanese International Corporation | Ethanol production from acetic acid utilizing a molybdenum carbide catalyst |
US9073816B2 (en) | 2011-04-26 | 2015-07-07 | Celanese International Corporation | Reducing ethyl acetate concentration in recycle streams for ethanol production processes |
WO2012149137A1 (en) | 2011-04-26 | 2012-11-01 | Celanese International Corporation | Process for the production of ethanol from an acetic acid feed and a recycled ethyl acetate feed |
US8592635B2 (en) | 2011-04-26 | 2013-11-26 | Celanese International Corporation | Integrated ethanol production by extracting halides from acetic acid |
US8754268B2 (en) | 2011-04-26 | 2014-06-17 | Celanese International Corporation | Process for removing water from alcohol mixtures |
US8895786B2 (en) | 2011-08-03 | 2014-11-25 | Celanese International Corporation | Processes for increasing alcohol production |
US8658843B2 (en) | 2011-10-06 | 2014-02-25 | Celanese International Corporation | Hydrogenation catalysts prepared from polyoxometalate precursors and process for using same to produce ethanol while minimizing diethyl ether formation |
US8536382B2 (en) | 2011-10-06 | 2013-09-17 | Celanese International Corporation | Processes for hydrogenating alkanoic acids using catalyst comprising tungsten |
US8703868B2 (en) | 2011-11-28 | 2014-04-22 | Celanese International Corporation | Integrated process for producing polyvinyl alcohol or a copolymer thereof and ethanol |
US9233899B2 (en) | 2011-12-22 | 2016-01-12 | Celanese International Corporation | Hydrogenation catalysts having an amorphous support |
US8575406B2 (en) | 2011-12-22 | 2013-11-05 | Celanese International Corporation | Catalysts having promoter metals and process for producing ethanol |
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CN103483121B (zh) * | 2012-06-08 | 2015-02-11 | 中国石油化工股份有限公司 | 一种由汽油制备丁二烯的方法 |
US8772553B2 (en) | 2012-10-26 | 2014-07-08 | Celanese International Corporation | Hydrogenation reaction conditions for producing ethanol |
US10376872B2 (en) | 2017-01-05 | 2019-08-13 | GM Global Technology Operations LLC | Solution-based approach to make porous coatings for sinter-resistant catalysts |
US10562017B2 (en) * | 2017-01-05 | 2020-02-18 | GM Global Technology Operations LLC | Ion adsorption of oxide layers to hinder catalyst sintering |
US10596563B2 (en) | 2017-01-27 | 2020-03-24 | GM Global Technology Operations LLC | Sinter-resistant stable catalyst systems by trapping of mobile platinum group metal (PGM) catalyst species |
KR102324239B1 (ko) * | 2017-11-06 | 2021-11-08 | 한화솔루션 주식회사 | 방향족 화합물의 수소화 반응용 촉매 및 이의 제조방법 |
EP3865558A1 (en) * | 2020-02-14 | 2021-08-18 | BASF Corporation | Process for the hydrogenation of hydrocarbon resins using catalysts with protective coatings |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1156060B (de) * | 1960-10-15 | 1963-10-24 | Bayer Ag | Verfahren zur Herstellung von feindispersen Calciumsilicatfuellstoffen |
US3095461A (en) * | 1961-01-05 | 1963-06-25 | California Research Corp | Preparation of 1-alkenes |
US3804652A (en) * | 1967-12-27 | 1974-04-16 | Chem & Insulating Co Ltd | Method of producing calcium silicate products |
DE2117375A1 (de) * | 1970-04-28 | 1971-12-09 | Agency Of Industrial Science & Technology, Tokio | Verfahren zur Herstellung von leichtem Calciumsilikatmaterial |
US3729429A (en) * | 1970-08-31 | 1973-04-24 | Exxon Research Engineering Co | Layered complex metal silicate compositions and their preparation |
JPS5622812B2 (ja) * | 1971-05-08 | 1981-05-27 | ||
US3751515A (en) * | 1972-03-28 | 1973-08-07 | Goodyear Tire & Rubber | Hydrogenation process |
US3928539A (en) * | 1972-05-05 | 1975-12-23 | Onoda Chem Ind Co Ltd | Method for continuously producing hydrated calcium silicates |
JPS53146997A (en) * | 1976-11-04 | 1978-12-21 | Osaka Patsukingu Seizoushiyo K | Spherical secondary particles of superlight calcium silicate |
JPS55109217A (en) * | 1979-02-09 | 1980-08-22 | Osaka Packing Seizosho:Kk | Calcium silicate and preparing the same |
JPS58176118A (ja) * | 1982-04-07 | 1983-10-15 | Ngk Spark Plug Co Ltd | 珪酸カルシウムの製造法 |
JPS58176117A (ja) * | 1982-04-07 | 1983-10-15 | Ngk Spark Plug Co Ltd | ゾノトライト系珪酸カルシウムの製造方法 |
US4689315A (en) * | 1984-04-14 | 1987-08-25 | Redco N.V. | Amorphous silica particles, a method for producing same, and catalyst thereof |
ES2039347T3 (es) * | 1985-11-29 | 1993-10-01 | Redco N.V. | Agregados de cristales sinteticos de xenotlita y procedimiento para prepararlos. |
JP2579633B2 (ja) * | 1987-04-04 | 1997-02-05 | 三菱化学株式会社 | 一酸化炭素含有廃ガスの処理方法 |
DE4025525A1 (de) * | 1990-08-11 | 1992-02-20 | Hoechst Ag | Traegerkatalysatoren und ein verfahren zu ihrer herstellung |
FR2729968B1 (fr) * | 1995-01-27 | 1997-04-11 | Inst Francais Du Petrole | Procede d'hydrogenation des diolefines et eventuellement des olefines de coupes hydrocarbures riches en composes aromatiques sur des catalyseurs metalliques impregenes de composes organiques soufres |
CN1044379C (zh) * | 1996-07-22 | 1999-07-28 | 中国石油化工总公司 | 一种芳烃加氢催化剂的制备方法 |
EP1277768A1 (en) * | 2001-07-18 | 2003-01-22 | ATOFINA Research | Polymer hydrogenation process |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US11584700B2 (en) | 2019-02-28 | 2023-02-21 | Dow Global Technologies Llc | Methods for operating acetylene hydrogenation units in olefin production processes |
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EP1277826A1 (en) | 2003-01-22 |
KR20040019336A (ko) | 2004-03-05 |
JP2009161766A (ja) | 2009-07-23 |
KR100881933B1 (ko) | 2009-02-06 |
CN100427571C (zh) | 2008-10-22 |
EP1406987A1 (en) | 2004-04-14 |
WO2003008519A1 (en) | 2003-01-30 |
US20040232049A1 (en) | 2004-11-25 |
CN1549851A (zh) | 2004-11-24 |
JP2004535470A (ja) | 2004-11-25 |
US7294604B2 (en) | 2007-11-13 |
US20080257784A1 (en) | 2008-10-23 |
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