JP5553889B2 - 希薄エチレンをオリゴマー化する方法 - Google Patents
希薄エチレンをオリゴマー化する方法 Download PDFInfo
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- JP5553889B2 JP5553889B2 JP2012503469A JP2012503469A JP5553889B2 JP 5553889 B2 JP5553889 B2 JP 5553889B2 JP 2012503469 A JP2012503469 A JP 2012503469A JP 2012503469 A JP2012503469 A JP 2012503469A JP 5553889 B2 JP5553889 B2 JP 5553889B2
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- ethylene
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- alumina
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Classifications
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
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- C07C2/10—Catalytic processes with metal oxides
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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
- C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
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- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/888—Tungsten
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- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
- B01J38/12—Treating with free oxygen-containing gas
- B01J38/30—Treating with free oxygen-containing gas in gaseous suspension, e.g. fluidised bed
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C11/02—Alkenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
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- C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
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- C07C2/08—Catalytic processes
- C07C2/24—Catalytic processes with metals
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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
- C10G11/00—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10G11/10—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils with stationary catalyst bed
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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
- C10G11/00—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10G11/14—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils with preheated moving solid catalysts
- C10G11/18—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils with preheated moving solid catalysts according to the "fluidised-bed" technique
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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
- C10G57/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one cracking process or refining process and at least one other conversion process
- C10G57/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one cracking process or refining process and at least one other conversion process with polymerisation
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
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- C—CHEMISTRY; METALLURGY
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- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
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- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
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Description
[0008]本発明の更なる特徴及び有利な点は、ここに与える発明の詳細な説明、図面、及び特許請求の範囲から明らかとなるであろう。
[0023]本発明者らは、乾性ガスエチレン流中の多くの不純物によってオリゴマー化触媒が被毒する可能性があることを見出した。水素及び一酸化炭素は金属部位を還元して不活性にする可能性がある。二酸化炭素及びアンモニアは触媒上の酸部位を攻撃する可能性がある。硫化水素は触媒上の金属を攻撃して金属硫化物を形成する可能性がある。アセチレンは触媒又は装置上で重合して粘着する可能性がある。
実施例1:
[0051]本発明の別の触媒に関して上記に示した手順により、アモルファスシリカ−アルミナ油滴下球状基材上のニッケル及びタングステンを合成した。金属は、触媒の1.5重量%のニッケル及び11重量%のタングステンを含んでいた。球状の基材は3.175mmの直径を有していた。触媒は、3のシリカ−アルミナ比、0.641g/mLの密度、及び371m2/gの表面積を有していた。
[0052]CICCによって提供された2.6のシリカ−アルミナ比を有するアモルファスシリカ−アルミナ及びCatapalの商標で提供された擬ベーマイトを85−15の重量比で混合することによって、押出アモルファスシリカ−アルミナを合成した。擬ベーマイトは、アモルファスシリカ−アルミナと混合する前に硝酸によって解膠させた。ドウを湿潤させるのに十分な量のAntaroxの商標で提供された界面活性剤及び水を混合物に加えた。触媒ドウを、円筒形ダイプレート内の1.59mmの開口を通して押出し、小片に破砕した後、550℃においてか焼した。85重量%のシリカ−アルミナ及び15重量%のアルミナから構成される最終触媒は、1.92のシリカ−アルミナ比を有し、368m2/gの表面積を有していた。
[0053]3.37gのNi(NO3)2・6H2Oを32.08gの脱イオン水中に溶解した。ニッケル溶液を4回に分けて加え、添加の間に激しく振盪することによって、ニッケル溶液を実施例2の押出アモルファスシリカ−アルミナと接触させた。明緑色の押出物が得られた。次に、押出物を110℃において3時間乾燥し、次に2℃/分で500℃に昇温して500℃において3時間保持することによってか焼し、次に室温に冷却することによって、ニッケル金属を酸化物に転化させた。明灰色の押出物は1.5重量%のニッケルを含むことが分かった。
[0054]シリカ−アルミナ比が40となるようなMTTゼオライトの試料をZeolyst Corporationから得た。MTTゼオライトを擬ベーマイトと混合し、円筒形ダイプレート内の3.175mmの開口を通して押出した後、550℃においてか焼した。最終触媒は80重量%のMTTゼオライト及び20重量%のアルミナから構成されていた。
[0055]実施例1の触媒を、280℃、6,895kPa(1000psig)、58OGHSV(オレフィンガスの空間速度)において、10mLの触媒上での固定床運転でオレフィンオリゴマー化に関して試験した。供給流は30重量%のC2H4及び70重量%のCH4から構成されていた。結果を表Iに示す。
[0056]実施例2の触媒を、280℃、6,895kPa(1000psig)、586OGHSVにおいて、10mLの触媒上での固定床運転でオレフィンオリゴマー化に関して試験した。供給流は23重量%のC2H4、14重量%のC2H6、35重量%のCH4、13重量%のH2、13重量%のN2、1重量%のCO、1.5重量%のCO2、10wppmのH2Sから構成されており、オリゴマー化反応に供給する前に25℃及び3,447kPa(500psig)において水蒸気で飽和した。結果を表I及び図2に示す。
[0057]実施例3の触媒を、280℃、6,895kPa(1000psig)、586OGHSVにおいて、10mLの触媒上での固定床運転でオレフィンオリゴマー化に関して試験した。供給流は23重量%のC2H4、14重量%のC2H6、35重量%のCH4、13重量%のH2、13重量%のN2、1重量%のCO、1.5重量%のCO2、10wppmのH2Sから構成されており、オリゴマー化反応に供給する前に25℃及び3,447kPa(500psig)において水蒸気で飽和した。結果を表I及び図2に示す。運転27〜44時間の間に、1ppmのNH3も供給流に加えた。転化率又は選択率の変化は見られなかった。
[0058]供給流中のH2Sの濃度が10wppmではなく50wppmであった他は、実施例7の実験を繰り返した。結果を表I及び図2に示す。
[0060]実施例4の触媒を、280℃、6,895kPa(1000psig)、586OGHSVにおいて、10mLの触媒上での固定床運転でオレフィンオリゴマー化に関して試験した。供給流は23重量%のC2H4、14重量%のC2H6、35重量%のCH4、13重量%のH2、13重量%のN2、1重量%のCO、1.5重量%のCO2、10wppmのH2Sから構成されており、オリゴマー化反応に供給する前に25℃及び3,447kPa(500psig)において水蒸気で飽和させた。結果を表I及び図3に示す。
[0062]実施例4の触媒を、280℃、6,895kPa(1000psig)、613OGHSVにおいて、10mLの触媒上での固定床運転でオレフィンオリゴマー化に関して試験した。供給流は30重量%のC2H4及び70重量%のCH4から構成されていた。運転21時間目に、水素を加えて27重量%のC2H4、63重量%のCH4、及び10重量%のH2から構成される供給流を得た。運転45時間目に、H2中の500wppmのNH3を加えて、27重量%のC2H4、63重量%のCH4、10重量%のH2、及び50wppmのNH3の供給流を得た。結果を表I及び図4に示す。
[0064]アンモニア温度プログラム脱離(アンモニアTPD)試験は、250mgの触媒試料をまず、100mL/分の流速のヘリウム雰囲気中、20体積%の酸素の存在下において、5℃/分の速度で550℃の温度に加熱することを含む。1時間保持した後、ヘリウムを用いて15分間系をフラッシングし、試料を150℃に冷却する。次に、試料を40mL/分のヘリウム中においてパルス状のアンモニアで飽和させた。用いるアンモニアの全量は、試料上の全ての酸部位を飽和するのに必要な量を大きく超えるものである。試料を40mL/分のヘリウムで8時間パージして、物理吸着したアンモニアを除去した。ヘリウムパージを継続しながら、温度を10℃/分の速度で600℃に最終温度に上昇させた。較正熱伝導度検出器を用いて脱離したアンモニアの量を観測した。積分によってアンモニアの全量を求めた。
[0071]当業者であれば、上記の記載から本発明の本質的特徴を容易に確認することができ、本発明の精神及び範囲から逸脱することなく、それを種々の用法及び条件に適合させるために本発明の種々の変更及び修正を行うことができる。
Claims (10)
- エチレンのオリゴマー化方法であって、
5〜50重量%のエチレン、並びに少なくとも0.1重量%の一酸化炭素、少なくとも1wppmの硫化水素、少なくとも1wppmのアンモニア、少なくとも5重量%の水素、及び少なくとも0.1重量%の二酸化炭素からなる群から選択される少なくとも1種類の不純物を含む供給流を提供すること;
該供給流を、周期律表第VIII族及び第VIB属からなる群から選択される金属を有するアモルファスシリカ−アルミナ基材を含む触媒と接触させること;及び
該供給流中のエチレンの少なくとも40重量%をより重質の炭化水素に転化させること;
を含む方法。 - 請求項1に記載の方法であって、該触媒が30以下のシリカ−アルミナ比を有する方法。
- 請求項1に記載の方法であって、該触媒が、0.5〜15重量%のニッケルを含浸させたアモルファスシリカ−アルミナ基材である方法。
- 請求項1に記載の方法であって、該触媒がアンモニア温度プログラム脱離試験によって測定して少なくとも0.15の低温酸性度比を有する方法。
- 請求項1に記載の方法であって、該供給流が0.5重量%以下のプロピレンを含む方法。
- 請求項1に記載の方法であって、該接触工程をエチレンに関する臨界圧力より高い圧力で行う方法。
- 請求項1に記載の方法であって、該供給流が、
分解触媒を重質炭化水素供給流と接触させて、該重質炭化水素をより低い分子量を有する分解生成物に分解すること;及び
該分解生成物を、5〜50重量%のエチレンを含む希薄エチレン流を含む複数の生成物流に分離すること;
により得られ、該希薄エチレン流を4,826〜7,584kPaの圧力に圧縮することを含む方法。 - 請求項7に記載の方法であって、該接触工程を触媒の固定床内で行う方法。
- 請求項7に記載の方法であって、該方法が、
該接触工程を行うための流体接触分解反応器;
該分解生成物を該反応器から排出するための生成物出口;
該分解生成物を該複数の生成物流に分離するための、該生成物出口と連通している生成物回収セクション;
該希薄エチレン流を圧縮するための、該生成物回収セクションと連通している圧縮機;及び
該希薄エチレン流中のエチレンをより重質の炭化水素にオリゴマー化するための、該圧縮機と連通している固定床オリゴマー化反応器;
を含む装置で行われる方法。 - 請求項9に記載の方法であって、該装置が、該生成物出口と連通している主カラム受容器、該希薄エチレン流を含む一次オフガス流を与えるための、主カラム受容器と連通している一次吸収器を更に含む方法。
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US12/416,029 US8575410B2 (en) | 2009-03-31 | 2009-03-31 | Process for oligomerizing dilute ethylene |
US12/416,029 | 2009-03-31 | ||
US12/416,026 | 2009-03-31 | ||
US12/416,026 US8748681B2 (en) | 2009-03-31 | 2009-03-31 | Process for oligomerizing dilute ethylene |
US12/416,032 | 2009-03-31 | ||
US12/416,032 US8021620B2 (en) | 2009-03-31 | 2009-03-31 | Apparatus for oligomerizing dilute ethylene |
PCT/US2010/026889 WO2010117539A2 (en) | 2009-03-31 | 2010-03-11 | Process for oligomerizing dilute ethylene |
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US5009851A (en) * | 1988-05-31 | 1991-04-23 | Mobil Oil Corporation | Integrated catalytic reactor system with light olefin upgrading |
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EP0734766B1 (en) * | 1995-03-29 | 2001-08-29 | Koa Oil Company, Limited | Olefin oligomerization catalyst, process for preparing the same, and olefin oligomerization process using the same |
WO1996034072A1 (en) * | 1995-04-27 | 1996-10-31 | Abb Lummus Global Inc. | Process for converting olefinic hydrocarbons using spent fcc catalyst |
US6660812B2 (en) * | 2000-07-13 | 2003-12-09 | Exxonmobil Chemical Patents Inc. | Production of olefin derivatives |
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US7525002B2 (en) * | 2005-02-28 | 2009-04-28 | Exxonmobil Research And Engineering Company | Gasoline production by olefin polymerization with aromatics alkylation |
-
2010
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- 2010-03-11 CN CN201080023632.XA patent/CN102448913B/zh active Active
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WO2010117539A2 (en) | 2010-10-14 |
EP2414310A2 (en) | 2012-02-08 |
EP2414310A4 (en) | 2015-04-29 |
TW201040251A (en) | 2010-11-16 |
KR101358589B1 (ko) | 2014-02-04 |
TWI412585B (zh) | 2013-10-21 |
CN102448913B (zh) | 2015-01-28 |
JP2012522109A (ja) | 2012-09-20 |
CN102448913A (zh) | 2012-05-09 |
WO2010117539A3 (en) | 2011-01-13 |
KR20120001795A (ko) | 2012-01-04 |
CN104276911A (zh) | 2015-01-14 |
MX2011010303A (es) | 2011-10-11 |
BRPI1013710A2 (pt) | 2016-04-05 |
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