JP4777895B2 - ジイソブチレンプロセス - Google Patents
ジイソブチレンプロセス Download PDFInfo
- Publication number
- JP4777895B2 JP4777895B2 JP2006533963A JP2006533963A JP4777895B2 JP 4777895 B2 JP4777895 B2 JP 4777895B2 JP 2006533963 A JP2006533963 A JP 2006533963A JP 2006533963 A JP2006533963 A JP 2006533963A JP 4777895 B2 JP4777895 B2 JP 4777895B2
- Authority
- JP
- Japan
- Prior art keywords
- diisobutylene
- zeolite
- isobutylene
- sulfur impurities
- catalyst
- 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 - Fee Related
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Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
- C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
-
- 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
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/28—Catalytic processes with hydrides or organic compounds with ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C9/00—Aliphatic saturated hydrocarbons
- C07C9/14—Aliphatic saturated hydrocarbons with five to fifteen carbon atoms
- C07C9/16—Branched-chain hydrocarbons
- C07C9/21—2, 2, 4-Trimethylpentane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- C07C2531/08—Ion-exchange resins
- C07C2531/10—Ion-exchange resins sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Materials For Medical Uses (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
米国特許第5,877,372号にしたがって190°Fの温度でイソブチレンを二量化してイソオクタン中ジイソブチレン(DIB)49.2重量%およびトリイソブチレン(TIB)1.5重量%の流れを製造する。生成物のジイソブチレン流れは700ppbの硫黄を含む。
イソオクタン中ジイソブチレン(DIB)49.2%、トリイソブチレン(TIB)1.5%を含むフィード流れの水素化をNi/SiO2触媒(Engelhard 3298E(使用前にH2中で還元)30cc、LHSV=5/時、リサイクル/フレッシュ=1、400psig、80℃)を使用してピストン流反応器中で行った。フィードの流れはHouston−Atlas硫黄分析器を使用して分析して700ppbの硫黄を含む。運転の最初の900時間の間に、DIB転化率は99.9%から98.7%に低下し、TIB転化率は100から68%に減退した。900時間後、13Xモレキュラーシーブを使用(100cc)して硫黄吸着床を取りつけた。吸着剤出口のフィード流れの分析により硫黄濃度が50ppb以下に減少することが明らかになった。硫黄が減少する結果として、DIB転化率が99.3%に増加して安定し、一方TIB転化率は80%に増加して同様に安定する。性能の劣化は300時間の運転後にしか観測されず、この時点で吸着剤出口の硫黄濃度は>300ppbとなる。吸着剤は空気中500℃に24時間か焼することにより再生可能である。
Claims (8)
- (a)スルホン酸樹脂触媒の存在下にイソブチレンをオリゴマー化して少量の硫黄不純物を含むジイソブチレンの流れを生成させること;次いで
(b)該ジイソブチレンの流れをゼオライト13Xの細孔サイズ以上であって15オングストロンまでの平均細孔サイズを有する細孔の大きなゼオライトと接触させて硫黄不純物の量が減少したジイソブチレン生成物を生成させること;を含む方法。 - 前記細孔の大きなゼオライトがゼオライトXである、請求項1記載の方法。
- 前記細孔の大きなゼオライトがゼオライトYである、請求項1記載の方法。
- 細孔の大きなゼオライトがナトリウム形態にある、請求項1記載の方法。
- 硫黄不純物の量が減少したジイソブチレン生成物を水素化触媒の存在下に水素化してイソオクタンを形成させる追加の工程(c)を含む請求項1記載の方法。
- 前記水素化触媒が担持ニッケル触媒である、請求項5記載の方法。
- (a)スルホン酸樹脂触媒の存在下にイソブチレンをオリゴマー化して少量の硫黄不純物を含むジイソブチレンの流れを生成させること;
(b)前記ジイソブチレンの流れを、ゼオライトXおよびゼオライトYからなる群から選ばれるゼオライト13Xの細孔サイズ以上であって15オングストロンまでの平均細孔サイズを有する細孔の大きなゼオライトと接触させて硫黄不純物の量が減少したジイソブチレン生成物を生成させること;および
(c)硫黄不純物の量が減少したジイソブチレン生成物を水素化触媒の存在下で水素化してイソオクタンを生成させること;を含む方法。 - 前記水素化触媒が担持ニッケル触媒である、請求項7記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/681,395 US7012167B2 (en) | 2003-10-08 | 2003-10-08 | Diisobutylene process |
US10/681,395 | 2003-10-08 | ||
PCT/US2004/031051 WO2005037739A1 (en) | 2003-10-08 | 2004-09-22 | Diisobutylene process |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007508302A JP2007508302A (ja) | 2007-04-05 |
JP4777895B2 true JP4777895B2 (ja) | 2011-09-21 |
Family
ID=34422270
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006533963A Expired - Fee Related JP4777895B2 (ja) | 2003-10-08 | 2004-09-22 | ジイソブチレンプロセス |
Country Status (11)
Country | Link |
---|---|
US (1) | US7012167B2 (ja) |
EP (1) | EP1670737B1 (ja) |
JP (1) | JP4777895B2 (ja) |
KR (1) | KR20060130022A (ja) |
CN (1) | CN100387558C (ja) |
AT (1) | ATE468311T1 (ja) |
BR (1) | BRPI0415112A (ja) |
CA (1) | CA2538731C (ja) |
DE (1) | DE602004027275D1 (ja) |
ES (1) | ES2342938T3 (ja) |
WO (1) | WO2005037739A1 (ja) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR036902A1 (es) | 2001-10-24 | 2004-10-13 | Exxonmobil Chem Patents Inc | Un proceso para la oligomerizacion de un material de alimentacion olefinico, usos de un limite en el nivel de azufre en el material de alimentacion, una mezcla oligomerica olefinica, y un ester o una composicion polimerica plastificada |
JP2011505490A (ja) | 2007-12-03 | 2011-02-24 | ジーヴォ,インコーポレイテッド | 再生可能組成物 |
US8193402B2 (en) * | 2007-12-03 | 2012-06-05 | Gevo, Inc. | Renewable compositions |
EP2070894A1 (en) | 2007-12-12 | 2009-06-17 | BP p.l.c. | A process for the conversion of n-butanol of n-butanol to di-isobutene and pentene |
EP2070896A1 (en) | 2007-12-12 | 2009-06-17 | BP p.l.c. | A process for the conversion of n-butanol to di-isobutene and propene |
EP2105428A1 (en) | 2007-12-12 | 2009-09-30 | BP p.l.c. | A process for the conversion of n-butanol to di-isobutene |
US8067655B2 (en) * | 2008-05-29 | 2011-11-29 | Lyondell Chemical Technology, L.P. | Diisobutylene process |
JP2012518658A (ja) * | 2009-02-24 | 2012-08-16 | ジーヴォ,インコーポレイテッド | 再生可能なブタジエンおよび再生可能なイソプレンの製造方法 |
JP2013506717A (ja) * | 2009-10-06 | 2013-02-28 | ジーヴォ,インコーポレイテッド | 再生可能なイソブタノールをp−キシレンに選択的に変換するための総合プロセス |
EP2521705A4 (en) | 2010-01-08 | 2014-06-18 | Gevo Inc | INTEGRATED METHODS OF MANUFACTURING RENEWABLE CHEMICALS |
WO2011140560A1 (en) | 2010-05-07 | 2011-11-10 | Gevo, Inc. | Renewable jet fuel blendstock from isobutanol |
EP2699618A4 (en) | 2011-04-19 | 2014-12-17 | Gevo Inc | VARIATIONS OF A PRINS REACTION FOR THE PREPARATION OF 2,5-DIMETHYLHEXADIENE FROM ISOBUTANOL |
CN107663147B (zh) * | 2016-07-29 | 2019-07-23 | 万华化学集团股份有限公司 | 一种分离叔丁醇与二异丁烯的方法和系统 |
CN108218654A (zh) * | 2018-02-12 | 2018-06-29 | 安徽海德化工科技有限公司 | 一种利用异丁醇制备异辛烷的方法 |
CN108658763A (zh) * | 2018-06-21 | 2018-10-16 | 岳阳富和科技有限公司 | 一种利用醋酸混合c4生成异辛烯,再加氢生产高纯异辛烷的制造方法 |
CN111217662B (zh) * | 2018-11-27 | 2022-11-18 | 中国石油化工股份有限公司 | 一种异丁烯叠合-加氢制备异辛烷的方法 |
CN111217661B (zh) * | 2018-11-27 | 2022-11-18 | 中国石油化工股份有限公司 | 一种异丁烯叠合-加氢制备异辛烷的方法 |
CN110578057B (zh) * | 2019-09-16 | 2020-08-04 | 中国原子能科学研究院 | 乏燃料后处理用稀释剂的制备方法 |
CN113929549B (zh) * | 2020-06-29 | 2023-12-08 | 中国石油化工股份有限公司 | 一种混合碳四选择性叠合方法 |
DE112021006329T5 (de) * | 2020-12-04 | 2023-09-14 | Sabic Global Technologies B.V. | Herstellung von isooctan aus feldbutan |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4100220A (en) * | 1977-06-27 | 1978-07-11 | Petro-Tex Chemical Corporation | Dimerization of isobutene |
JP2000279816A (ja) * | 1999-03-12 | 2000-10-10 | Agip Petroli Spa | 炭化水素混合物の品質改良用触媒組成物 |
JP2004505008A (ja) * | 1999-12-23 | 2004-02-19 | エクソンモービル ケミカル パテンツ インコーポレイテッド | イソブテンの選択的二量化方法 |
JP2004123714A (ja) * | 2002-08-06 | 2004-04-22 | Oxeno Olefinchemie Gmbh | n−ブテン含有の炭化水素流中でイソブテンをオリゴマー化する方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
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US3351635A (en) | 1966-03-14 | 1967-11-07 | Halcon International Inc | Epoxidation process |
US3510538A (en) | 1967-12-15 | 1970-05-05 | Atlantic Richfield Co | Continuous process for dehydration of tertiary butyl alcohol |
US4155945A (en) | 1978-07-24 | 1979-05-22 | Cities Service Company | Continuous process for dehydration of tertiary butyl alcohol |
US4165343A (en) | 1978-07-28 | 1979-08-21 | Cities Service Conmpany | Dehydration of tertiary butyl alcohol |
US4447668A (en) | 1982-03-29 | 1984-05-08 | Chemical Research & Licensing Company | Process for producing high purity isoolefins and dimers thereof by dissociation of ethers |
NL8901239A (nl) * | 1989-05-18 | 1990-12-17 | Meern Bv Engelhard De | Katalysator voor hydrogenering en/of dehydrogenering. |
US5625109A (en) | 1994-11-21 | 1997-04-29 | Gupta; Vijai P. | Liquid phase dehydration of tertiary butyl alcohol |
DE19629903A1 (de) * | 1996-07-24 | 1998-01-29 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Buten-Oligomeren aus Feldbutanen |
US5877372A (en) | 1997-11-21 | 1999-03-02 | Arco Chemical Technology, L.P. | Isobutylene oligomerization using isooctane diluent |
US6376731B1 (en) | 2000-01-14 | 2002-04-23 | Arco Chemical Technology, L.P. | Selective olefin oligomerization |
-
2003
- 2003-10-08 US US10/681,395 patent/US7012167B2/en not_active Expired - Fee Related
-
2004
- 2004-09-22 KR KR1020067006124A patent/KR20060130022A/ko active IP Right Grant
- 2004-09-22 JP JP2006533963A patent/JP4777895B2/ja not_active Expired - Fee Related
- 2004-09-22 ES ES04784768T patent/ES2342938T3/es active Active
- 2004-09-22 BR BRPI0415112-7A patent/BRPI0415112A/pt not_active IP Right Cessation
- 2004-09-22 AT AT04784768T patent/ATE468311T1/de not_active IP Right Cessation
- 2004-09-22 DE DE602004027275T patent/DE602004027275D1/de active Active
- 2004-09-22 WO PCT/US2004/031051 patent/WO2005037739A1/en active Application Filing
- 2004-09-22 CN CNB2004800287330A patent/CN100387558C/zh not_active Expired - Fee Related
- 2004-09-22 CA CA2538731A patent/CA2538731C/en not_active Expired - Fee Related
- 2004-09-22 EP EP04784768A patent/EP1670737B1/en not_active Not-in-force
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4100220A (en) * | 1977-06-27 | 1978-07-11 | Petro-Tex Chemical Corporation | Dimerization of isobutene |
JP2000279816A (ja) * | 1999-03-12 | 2000-10-10 | Agip Petroli Spa | 炭化水素混合物の品質改良用触媒組成物 |
JP2004505008A (ja) * | 1999-12-23 | 2004-02-19 | エクソンモービル ケミカル パテンツ インコーポレイテッド | イソブテンの選択的二量化方法 |
JP2004123714A (ja) * | 2002-08-06 | 2004-04-22 | Oxeno Olefinchemie Gmbh | n−ブテン含有の炭化水素流中でイソブテンをオリゴマー化する方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20060130022A (ko) | 2006-12-18 |
US7012167B2 (en) | 2006-03-14 |
CA2538731A1 (en) | 2005-04-28 |
WO2005037739A1 (en) | 2005-04-28 |
DE602004027275D1 (de) | 2010-07-01 |
CN1863753A (zh) | 2006-11-15 |
CN100387558C (zh) | 2008-05-14 |
CA2538731C (en) | 2011-07-12 |
ES2342938T3 (es) | 2010-07-19 |
EP1670737A1 (en) | 2006-06-21 |
ATE468311T1 (de) | 2010-06-15 |
BRPI0415112A (pt) | 2006-11-28 |
US20050080305A1 (en) | 2005-04-14 |
EP1670737B1 (en) | 2010-05-19 |
JP2007508302A (ja) | 2007-04-05 |
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