JP4892488B2 - ジイソブチレンの製造方法 - Google Patents
ジイソブチレンの製造方法 Download PDFInfo
- Publication number
- JP4892488B2 JP4892488B2 JP2007543025A JP2007543025A JP4892488B2 JP 4892488 B2 JP4892488 B2 JP 4892488B2 JP 2007543025 A JP2007543025 A JP 2007543025A JP 2007543025 A JP2007543025 A JP 2007543025A JP 4892488 B2 JP4892488 B2 JP 4892488B2
- Authority
- JP
- Japan
- Prior art keywords
- isobutylene
- solid adsorbent
- diisobutylene
- sulfonic acid
- feed stream
- 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
Links
Classifications
-
- 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
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
- C07C11/09—Isobutene
-
- 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
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Materials For Medical Uses (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Catalysts (AREA)
Description
CatB−B精油所イソブチレン(95重量%)およびt−ブチルアルコール(TBA、5重量%)を含むイソブチレン反応供給原料を、スルホン化したイオン交換樹脂を入れた1インチの固定床反応器(30g、ピュロライトCT275、WHSV=2.1/時、93℃)に供給する(63g/時で)。イソブチレン反応供給原料の流速は63g/時(2.1WHSV)である。CatB-B精油所イソブチレンはイソブチレン16.78重量%、イソブタン28.37重量%、n−ブタン13.55重量%、1−ブテン13.07重量%、1,3-ブタジエン0.33重量%、トランス2−ブテン14.26重量%、シス2−ブテン10.37重量%、プロパン1.17重量%、プロピレン1.41重量%、1−ペンテン0.69重量%、S15ppmおよびN65ppmを含む。反応器は3ゾーン炉を使用して93℃に維持され、生成物流は反応開始後の種々の時間にGCによって分析した。
CatB-B精油所イソブチレン(95重量%)およびt−ブチルアルコール(TBA、5重量%)を含むイソブチレン反応供給原料を、22℃でのオリゴマー化に先立って、90gのUOP13XHPモレキュラーシーブ吸着材を充填した1インチステンレス管に最初に供給する以外は実施例1の手順を繰り返した。該供給原料(吸着材と接触後S8〜10ppmおよびN11ppmを含んでいた)を13Xモレキュラーシーブ吸着材中、次いでオリゴマー化反応器中に連続的に通過させた。
Claims (10)
- (a)ターシャリーブタノールおよび/または水を含むイソブチレンの供給原料流であって、硫黄および/または窒素不純物を含む供給原料流を固体吸着材と接触させて硫黄および/または窒素不純物の量を減らした接触したイソブチレンを生成させる工程、ここで前記固体吸着材は、モレキュラーシーブ、酸化アルミニウム、酸化シリコン、シリカーアルミナ、スルホン酸樹脂、およびそれらの混合物からなる群から選ばれるものであり、および
(b)前記接触したイソブチレンをスルホン酸樹脂触媒の存在下にオリゴマー化してジイソブチレンを生成させる工程、
を含む製造方法。 - 前記固体吸着材が13Xモレキュラーシーブ、ZSM−5、ゼオライトX、ゼオライトYおよびそれらの混合物からなる群から選ばれる、請求項1記載の製造方法。
- 前記固体吸着材が13Xモレキュラーシーブを含む、請求項1記載の製造方法。
- 前記イソブチレンの供給原料流が、流動接触分解による原油の精製中に得られるC 4 流である、請求項1記載の製造方法。
- 水素化触媒の存在下でジイソブチレンを水素化してイソオクタンを生成させることをさらに含む請求項1記載の製造方法。
- 前記水素化触媒が担持ニッケル触媒である、請求項5記載の製造方法。
- 前記固体吸着材が13Xモレキュラーシーブ、ZSM−5、ゼオライトX、ゼオライトY、およびそれらの混合物からなる群から選ばれる、請求項5記載の製造方法。
- 前記固体吸着材が13Xモレキュラーシーブを含む、請求項5記載の製造方法。
- 前記イソブチレンの供給原料流が流動接触分解による原油の精製中に得られるC 4 流である、請求項8記載の製造方法。
- 前記イソブチレンの供給原料流を、20〜60℃の温度下に少なくとも1種の固体吸着材床を液相で通過させることにより、供給原料流を固体吸着材と接触させる請求項1記載の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/994,513 | 2004-11-22 | ||
US10/994,513 US20060111598A1 (en) | 2004-11-22 | 2004-11-22 | Diisobutylene process |
PCT/US2005/032332 WO2006057692A1 (en) | 2004-11-22 | 2005-09-09 | Diisobutylene process |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008520664A JP2008520664A (ja) | 2008-06-19 |
JP4892488B2 true JP4892488B2 (ja) | 2012-03-07 |
Family
ID=35541593
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007543025A Expired - Fee Related JP4892488B2 (ja) | 2004-11-22 | 2005-09-09 | ジイソブチレンの製造方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US20060111598A1 (ja) |
EP (1) | EP1814833B1 (ja) |
JP (1) | JP4892488B2 (ja) |
KR (1) | KR20070084335A (ja) |
CN (1) | CN101061083A (ja) |
AT (1) | ATE414052T1 (ja) |
BR (1) | BRPI0518454A2 (ja) |
CA (1) | CA2588989A1 (ja) |
DE (1) | DE602005011042D1 (ja) |
ES (1) | ES2314720T3 (ja) |
WO (1) | WO2006057692A1 (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080029437A1 (en) * | 2006-08-02 | 2008-02-07 | Exxonmobil Research And Engineering Company | Olefin upgrading process with guard bed regeneration |
FR2918297B1 (fr) * | 2007-07-06 | 2011-03-25 | Inst Francais Du Petrole | Purification d'une coupe olefinique par adsorption sur des cogranules alumine-faujasite. |
US8715490B2 (en) | 2009-12-23 | 2014-05-06 | Uop Llc | Low metal biomass-derived pyrolysis oils and processes for producing the same |
CN104211558B (zh) * | 2013-05-31 | 2016-09-14 | 中国科学院兰州化学物理研究所苏州研究院 | 一种由二异丁烯制备对二甲苯联产异辛烷的方法 |
WO2015137422A1 (ja) * | 2014-03-13 | 2015-09-17 | 出光興産株式会社 | オレフィンのオリゴマー化触媒及びオレフィン二量体の製造方法 |
EP3964492A1 (en) * | 2020-09-05 | 2022-03-09 | Indian Oil Corporation Limited | A process and apparatus for production and separation of alcohols and oligomerization of hydrocarbon feedstock |
CN113636903B (zh) * | 2021-08-12 | 2023-03-03 | 万华化学集团股份有限公司 | 一种异丁烯齐聚制备三异丁烯的方法 |
CN114349588B (zh) * | 2021-12-29 | 2023-09-19 | 万华化学集团股份有限公司 | 一种异辛烷、异构十二烷和异构十六烷的制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5444604A (en) * | 1977-08-26 | 1979-04-09 | Inst Francais Du Petrole | Method of converting steam cracking c4 olefin fraction to isooctane and butane |
JPH02306926A (ja) * | 1989-05-05 | 1990-12-20 | Huels Ag | オレフインのオリゴマー化方法 |
JP2001524458A (ja) * | 1997-11-21 | 2001-12-04 | アルコ・ケミカル・テクノロジー・エル・ピー | イソブチレンをオリゴマー化する方法 |
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 (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US4100220A (en) * | 1977-06-27 | 1978-07-11 | Petro-Tex Chemical Corporation | Dimerization of isobutene |
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 |
US4575567A (en) * | 1982-07-06 | 1986-03-11 | Uop Inc. | Adsorbent regeneration in etherification processes |
US5120881A (en) * | 1988-11-22 | 1992-06-09 | Exxon Chemical Patents Inc | Removal of nitrogenous components of a hydrocarbon feedstream |
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 |
IT1311512B1 (it) * | 1999-03-12 | 2002-03-13 | Agip Petroli | Composizione catalitica per l'upgrading di miscele idrocarburiche. |
GB9930402D0 (en) * | 1999-12-23 | 2000-02-16 | Exxon Chemical Patents Inc | Selective removal of isobutene from C4 olefinic feedstocks |
US6376731B1 (en) * | 2000-01-14 | 2002-04-23 | Arco Chemical Technology, L.P. | Selective olefin oligomerization |
EP1620376B1 (en) * | 2003-03-24 | 2016-12-07 | ExxonMobil Chemical Patents Inc. | Alkylation of an aromatic hydrocarbon feedstock with its pretreatment via two different molecular sieves |
-
2004
- 2004-11-22 US US10/994,513 patent/US20060111598A1/en not_active Abandoned
-
2005
- 2005-09-09 BR BRPI0518454-1A patent/BRPI0518454A2/pt not_active IP Right Cessation
- 2005-09-09 ES ES05796524T patent/ES2314720T3/es active Active
- 2005-09-09 EP EP05796524A patent/EP1814833B1/en not_active Not-in-force
- 2005-09-09 WO PCT/US2005/032332 patent/WO2006057692A1/en active Search and Examination
- 2005-09-09 AT AT05796524T patent/ATE414052T1/de not_active IP Right Cessation
- 2005-09-09 DE DE602005011042T patent/DE602005011042D1/de active Active
- 2005-09-09 CA CA002588989A patent/CA2588989A1/en not_active Abandoned
- 2005-09-09 JP JP2007543025A patent/JP4892488B2/ja not_active Expired - Fee Related
- 2005-09-16 CN CNA2005800399472A patent/CN101061083A/zh active Pending
- 2005-09-16 KR KR1020077011268A patent/KR20070084335A/ko not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5444604A (en) * | 1977-08-26 | 1979-04-09 | Inst Francais Du Petrole | Method of converting steam cracking c4 olefin fraction to isooctane and butane |
JPH02306926A (ja) * | 1989-05-05 | 1990-12-20 | Huels Ag | オレフインのオリゴマー化方法 |
JP2001524458A (ja) * | 1997-11-21 | 2001-12-04 | アルコ・ケミカル・テクノロジー・エル・ピー | イソブチレンをオリゴマー化する方法 |
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 |
---|---|
DE602005011042D1 (de) | 2008-12-24 |
US20060111598A1 (en) | 2006-05-25 |
WO2006057692A8 (en) | 2007-07-26 |
KR20070084335A (ko) | 2007-08-24 |
WO2006057692A1 (en) | 2006-06-01 |
CN101061083A (zh) | 2007-10-24 |
EP1814833B1 (en) | 2008-11-12 |
BRPI0518454A2 (pt) | 2008-11-18 |
ATE414052T1 (de) | 2008-11-15 |
CA2588989A1 (en) | 2006-06-01 |
EP1814833A1 (en) | 2007-08-08 |
ES2314720T3 (es) | 2009-03-16 |
JP2008520664A (ja) | 2008-06-19 |
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