JP4728577B2 - オレフィンのオリゴマー化の方法 - Google Patents
オレフィンのオリゴマー化の方法 Download PDFInfo
- Publication number
- JP4728577B2 JP4728577B2 JP2003538102A JP2003538102A JP4728577B2 JP 4728577 B2 JP4728577 B2 JP 4728577B2 JP 2003538102 A JP2003538102 A JP 2003538102A JP 2003538102 A JP2003538102 A JP 2003538102A JP 4728577 B2 JP4728577 B2 JP 4728577B2
- Authority
- JP
- Japan
- Prior art keywords
- oligomerization
- sulfur
- feedstock
- olefin
- branching
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7042—TON-type, e.g. Theta-1, ISI-1, KZ-2, NU-10 or ZSM-22
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7026—MFS-type, e.g. ZSM-57
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/80—Mixtures of different zeolites
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/20—Sulfiding
-
- 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
- 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
- C07C2/08—Catalytic processes
- C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
-
- 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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
- B01J2229/186—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself not in framework positions
-
- 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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/34—Reaction with organic or organometallic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
タイプI RCH=CH2
タイプII RCH=CHR’
タイプIII RRC=CH2
タイプIV RR’C=CHR’’
タイプV RR’C=CR’’R’’’
(式中、R、R’、R’’及びR’’’はアルキル基である)
である5種の骨格構造に分類される。オレフィン種は、プロトンNMR分析により特定される。特に、制御された平均分岐度と組み合わされて、本発明のオリゴマー生成物は、伝統的な、例えば、担持された燐酸触媒での方法により生成されたオリゴマー生成物より利点を有する。それらの利点は、主に、より低い平均分岐度及びタイプVオレフィンのより低い割合であり、オリゴマー組成物をオキソ法(ヒドロホルミル化)に付す場合の望ましい反応性のために、オリゴマー生成物を、その後の処理、より高級のアルコール、アルデヒド及び酸製造、のために、より適するものにさせる。
下記の実施例は本発明を例示し、部及び%は、他に示されていなければ、重量に基いている。
として表わされる。
本実施例では、市販のZSM−22触媒[アルミナに担持されたZSM−22(75%)]で、6.8時間−1の毎時重量空間速度において、40℃における水に通過させることにより水和された、60乃至65%のブテン類/35乃至40%のブタン供給原料においてブテンオリゴマー化を行なった。反応器流体をガスクロマトグラフィー(GC)により分析し、供給原料及び生成物のオレフィン/パラフィン比を比較し、変換率を決定した。液体生成物を、オレフィン類をパラフィンに水素化するためのプラチナ触媒を有するGC装置で分析し、炭素数及び骨格を決定した。比較試料のC1及びC3において、純粋な(すなわち、硫黄非含有の)ブテン供給原料を用い、比較試料のC2及び実施例1において、20ppmの硫黄(16ppmの硫化ジメチル、1.5ppmの硫化ジエチル、残量は、硫化メチルエチル及びメルカプタン類)を含有する精油所供給原料を用いた。
本実施例は、プロペンオリゴマー化において、ZSM−57の活性度における硫黄の影響及びその影響における高温の作用を示す。
実施例2の純粋な供給原料に7ppmの硫化エチルを添加し、実施例2において用いられた触媒により、168℃において、オリゴマー化を行った。生成物流れは、約66%のノネン類、11%のドデセン類及び9重量%のヘキセン類を含有し、ノネン類の分岐度は2.0であった。変換率は93%であった。
Claims (7)
- 350℃までの温度、5から10MPaの範囲の圧力、0.1から20時間−1の範囲のオレフィン毎時空間速度を含むオリゴマー化条件下で、プロペン、ブテン類、ペンテン類及び、またはヘキセン類を含有し、かつ硫化水素、硫黄含有飽和脂肪族化合物、及びそれらの混合物から選ばれる、1乃至100容量ppmの、少なくとも1つの硫黄含有化合物を含有するオレフィン系供給原料を、TONとMFS構造種の篩から選ばれる少なくとも1つの結晶質分子篩を含有する触媒と接触させること、その際のオリゴマー化の温度が、TON構造種の篩については少なくとも190℃であり、MFS構造種の篩については、少なくとも160℃であり、及び硫黄含有化合物を含有しないオレフィン系供給原料を用い、本方法のオリゴマー化の温度よりも低いオリゴマー化の温度を用いる点で本方法と異なっているオリゴマー化の方法の実施後に回収される同一のオリゴマーの分岐度と比較して低い分岐度を有する少なくとも1つのオレフィンオリゴマーを含有する生成物を回収することを含む、オレフィン系供給原料のオリゴマー化の方法。
- 少なくとも200℃の温度においてTON構造種の分子篩を含有する触媒を用いて行われる請求項1に記載の方法。
- 結晶質分子篩が、H−ZSM−22及びH−ZSM−57の混合物を含有する、請求項1に記載の方法。
- 供給原料をオリゴマー化に付す前に供給原料の硫黄含量が低減されている、請求項1乃至3のいずれか1請求項に記載の方法。
- 硫黄含有化合物が、硫化水素、硫化ジメチル、硫化ジエチル、硫化エチルメチル、硫化n−プロピル、1−プロパンチオール、2−プロパンチオール、1−ブタンチオール、1,1−メチルエチルチオール、二硫化エチルメチル、二硫化ジメチル及びテトラヒドロチオフェンから選ばれる少なくとも1つの化合物を含有する、請求項1乃至4のいずれか1請求項に記載の方法。
- 前記回収した生成物がオリゴマーヘキセン混合物、オリゴマーノネン混合物及びオリゴマードデセン混合物から選ばれるオリゴマーオレフィン混合物を含有する、請求項1乃至5のいずれかの1請求項による方法。
- 供給原料が、 オリゴマーを含有する、請求項1乃至6のいずれか1請求項に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01309013 | 2001-10-24 | ||
EP01309032.9 | 2001-10-24 | ||
EP01309032 | 2001-10-24 | ||
EP01309013.9 | 2001-10-24 | ||
PCT/GB2002/004776 WO2003035584A1 (en) | 2001-10-24 | 2002-10-23 | Process for the oligomerization of olefins |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010228704A Division JP2011042799A (ja) | 2001-10-24 | 2010-10-08 | オリゴマー化反応の生成物の分岐度を制御する方法 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2005506374A JP2005506374A (ja) | 2005-03-03 |
JP2005506374A5 JP2005506374A5 (ja) | 2010-12-09 |
JP4728577B2 true JP4728577B2 (ja) | 2011-07-20 |
Family
ID=26077182
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003538102A Expired - Lifetime JP4728577B2 (ja) | 2001-10-24 | 2002-10-23 | オレフィンのオリゴマー化の方法 |
JP2010228704A Pending JP2011042799A (ja) | 2001-10-24 | 2010-10-08 | オリゴマー化反応の生成物の分岐度を制御する方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010228704A Pending JP2011042799A (ja) | 2001-10-24 | 2010-10-08 | オリゴマー化反応の生成物の分岐度を制御する方法 |
Country Status (6)
Country | Link |
---|---|
US (2) | US7186874B2 (ja) |
EP (2) | EP2311787B1 (ja) |
JP (2) | JP4728577B2 (ja) |
CN (1) | CN1319913C (ja) |
WO (1) | WO2003035584A1 (ja) |
ZA (1) | ZA200402835B (ja) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2311787B1 (en) * | 2001-10-24 | 2019-01-09 | ExxonMobil Chemical Patents Inc. | Process for the oligomerisation of olefins |
US20070255081A1 (en) * | 2003-12-18 | 2007-11-01 | Exxonmobil Chemical Company | Catalysed Reactions |
GB0412151D0 (en) | 2004-06-01 | 2004-06-30 | Exxonmobil Chem Patents Inc | Olefin oligomerization process |
GB0412139D0 (en) | 2004-06-01 | 2004-06-30 | Exxonmobil Chem Patents Inc | Olefin oligomerization process |
GB0510887D0 (en) * | 2005-05-31 | 2005-07-06 | Exxonmobil Chem Patents Inc | Oligomerization using molecular sieve catalysts |
GB0511051D0 (en) * | 2005-05-31 | 2005-07-06 | Exxonmobil Chem Patents Inc | Molecular sieve catalyst treatment |
WO2007040812A1 (en) * | 2005-09-30 | 2007-04-12 | Exxonmobil Chemical Patents Inc. | Oligomerization reaction |
WO2009103393A2 (en) * | 2008-02-22 | 2009-08-27 | Exxonmobil Chemical Patents Inc. | High metal content molecular sieves and their manufacture |
US8476350B2 (en) * | 2008-12-24 | 2013-07-02 | Exxonmobil Research And Engineering Company | Triglyceride plasticizer and process of making |
WO2010079018A1 (en) * | 2009-01-08 | 2010-07-15 | Exxonmobil Chemical Patents Inc. | Improvements in or relating to alcohols |
US20110184105A1 (en) * | 2009-09-29 | 2011-07-28 | Exxonmobil Research And Engineering Company | Phenylene Oxo-Diester Plasticizers and Methods of Making |
US8921590B2 (en) | 2009-12-15 | 2014-12-30 | Exxonmobil Chemical Patents Inc. | Oligomerisation process |
US8771815B2 (en) | 2009-12-17 | 2014-07-08 | Exxonmobil Research And Engineering Company | Process for making triglyceride plasticizer |
US8568846B2 (en) * | 2009-12-24 | 2013-10-29 | Exxonmobil Research And Engineering Company | Process for making polyol neoalkylester plasticizers from neo acids |
EP2404980A1 (en) | 2010-07-08 | 2012-01-11 | Total Raffinage Marketing | Hydrocarbon feedstock average molecular weight increase |
KR20140019318A (ko) | 2010-12-28 | 2014-02-14 | 토탈 라피나쥬 마케팅 | 니트릴 함유 탄화수소 공급원료, 이의 제조방법 및 용도 |
WO2013104614A1 (en) | 2012-01-09 | 2013-07-18 | Total Raffinage Marketing | Method for the conversion of low boiling point olefin containing hydrocarbon feedstock |
US9359456B2 (en) | 2012-09-24 | 2016-06-07 | Exxonmobil Chemical Patents Inc. | Catalytic hydroformylation of vinyl terminated polyolefins |
US9284387B2 (en) | 2012-09-24 | 2016-03-15 | Exxonmobil Chemical Patents Inc. | Hydroamination of aldehyde-containing macromonomers |
EP3008015A1 (en) * | 2013-06-10 | 2016-04-20 | ExxonMobil Chemical Patents Inc. | A process for making molecular sieves |
DE102014209536A1 (de) * | 2014-05-20 | 2015-11-26 | Evonik Degussa Gmbh | Herstellung qualitativ hochwertiger Oxo-Alkohole aus unsteten Rohstoffquellen |
CN110300740A (zh) * | 2017-03-15 | 2019-10-01 | 埃克森美孚化学专利公司 | 低聚方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5869821A (ja) * | 1981-09-25 | 1983-04-26 | シエブロン・リサ−チ・コンパニ− | 気体オレフインのオリゴマ−化方法 |
JPS59206485A (ja) * | 1983-04-26 | 1984-11-22 | モ−ビル・オイル・コ−ポレ−シヨン | オレフイン性原料をオリゴメリゼ−シヨンしてより重質な炭化水素を製造する接触転化方法及び装置 |
JPS6172618A (ja) * | 1984-08-21 | 1986-04-14 | モービル オイル コーポレーシヨン | ゼオライト、その合成方法及びそれを用いた有機転化反応 |
JPH03210392A (ja) * | 1989-11-16 | 1991-09-13 | Mobil Oil Corp | 軽質オレフィンの改質方法 |
Family Cites Families (12)
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US3527838A (en) * | 1969-01-13 | 1970-09-08 | Shell Oil Co | Ethylene oligomerization |
US4556477A (en) | 1984-03-07 | 1985-12-03 | Mobil Oil Corporation | Highly siliceous porous crystalline material ZSM-22 and its use in catalytic dewaxing of petroleum stocks |
JPH0429136Y2 (ja) | 1988-07-11 | 1992-07-15 | ||
US5157201A (en) * | 1990-06-22 | 1992-10-20 | Exxon Chemical Patents Inc. | Process for adsorbing sulfur species from propylene/propane using regenerable adsorbent |
ATE131467T1 (de) * | 1990-07-27 | 1995-12-15 | Exxon Chemical Patents Inc | Behandlung von kohlenwasserstoffen |
EP0757976A3 (en) | 1992-01-30 | 1998-01-28 | Exxon Chemical Patents Inc. | Alkene oligomerisation with crystals of H-ZSM or ZSM catalysts |
ATE166039T1 (de) | 1992-06-05 | 1998-05-15 | Exxon Chemical Patents Inc | Zsm 22 zeolith |
GB9225183D0 (en) * | 1992-12-02 | 1993-01-20 | British Petroleum Co Plc | Process for the production of branched olefins |
WO1995022516A1 (en) * | 1994-02-22 | 1995-08-24 | Exxon Chemical Patents Inc. | Oligomerization and catalysts therefor |
WO1999052631A1 (en) * | 1998-04-15 | 1999-10-21 | Shell Internationale Research Maatschappij B.V. | CATALYST SYSTEM FOR α-OLEFIN OLIGOMERIZATION |
WO2001074970A2 (en) * | 2000-04-03 | 2001-10-11 | Chevron U.S.A. Inc. | Improved conversion of syngas to distillate fuels |
EP2311787B1 (en) * | 2001-10-24 | 2019-01-09 | ExxonMobil Chemical Patents Inc. | Process for the oligomerisation of olefins |
-
2002
- 2002-10-23 EP EP10189203.2A patent/EP2311787B1/en not_active Expired - Lifetime
- 2002-10-23 CN CNB028211081A patent/CN1319913C/zh not_active Expired - Fee Related
- 2002-10-23 US US10/492,705 patent/US7186874B2/en not_active Expired - Fee Related
- 2002-10-23 WO PCT/GB2002/004776 patent/WO2003035584A1/en active Application Filing
- 2002-10-23 EP EP02770093.9A patent/EP1438275B1/en not_active Expired - Lifetime
- 2002-10-23 JP JP2003538102A patent/JP4728577B2/ja not_active Expired - Lifetime
-
2004
- 2004-04-15 ZA ZA2004/02835A patent/ZA200402835B/en unknown
-
2007
- 2007-01-09 US US11/651,160 patent/US7541507B2/en not_active Expired - Fee Related
-
2010
- 2010-10-08 JP JP2010228704A patent/JP2011042799A/ja active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5869821A (ja) * | 1981-09-25 | 1983-04-26 | シエブロン・リサ−チ・コンパニ− | 気体オレフインのオリゴマ−化方法 |
JPS59206485A (ja) * | 1983-04-26 | 1984-11-22 | モ−ビル・オイル・コ−ポレ−シヨン | オレフイン性原料をオリゴメリゼ−シヨンしてより重質な炭化水素を製造する接触転化方法及び装置 |
JPS6172618A (ja) * | 1984-08-21 | 1986-04-14 | モービル オイル コーポレーシヨン | ゼオライト、その合成方法及びそれを用いた有機転化反応 |
JPH03210392A (ja) * | 1989-11-16 | 1991-09-13 | Mobil Oil Corp | 軽質オレフィンの改質方法 |
Also Published As
Publication number | Publication date |
---|---|
EP2311787B1 (en) | 2019-01-09 |
CN1319913C (zh) | 2007-06-06 |
US7186874B2 (en) | 2007-03-06 |
US7541507B2 (en) | 2009-06-02 |
EP1438275A1 (en) | 2004-07-21 |
ZA200402835B (en) | 2005-02-23 |
WO2003035584A1 (en) | 2003-05-01 |
EP1438275B1 (en) | 2016-05-18 |
JP2011042799A (ja) | 2011-03-03 |
EP2311787A1 (en) | 2011-04-20 |
JP2005506374A (ja) | 2005-03-03 |
US20050014630A1 (en) | 2005-01-20 |
CN1575266A (zh) | 2005-02-02 |
US20070191654A1 (en) | 2007-08-16 |
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