JP4302510B2 - 直鎖率の高いアルコール組成物を調製する方法 - Google Patents
直鎖率の高いアルコール組成物を調製する方法 Download PDFInfo
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- JP4302510B2 JP4302510B2 JP2003503577A JP2003503577A JP4302510B2 JP 4302510 B2 JP4302510 B2 JP 4302510B2 JP 2003503577 A JP2003503577 A JP 2003503577A JP 2003503577 A JP2003503577 A JP 2003503577A JP 4302510 B2 JP4302510 B2 JP 4302510B2
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- Prior art keywords
- weight
- alcohol
- catalyst
- linear
- hydrogen
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Classifications
-
- 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
- C10G2/00—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon
- C10G2/30—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen
- C10G2/32—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- 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
- C10G2/00—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon
- C10G2/30—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen
- C10G2/32—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts
- C10G2/33—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts characterised by the catalyst used
- C10G2/331—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts characterised by the catalyst used containing group VIII-metals
- C10G2/332—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts characterised by the catalyst used containing group VIII-metals of the iron-group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
1種または複数の第1級モノアルコールを含み、その少なくとも60重量%が少なくとも7個の炭素原子含む直鎖第1級モノアルコールからなる、アルコール組成物を調製する方法であって、
(a)コバルトを含むフィッシャー−トロプシュ触媒の存在下、フィッシャー−トロプシュ反応条件の下で一酸化炭素を水素と反応させる段階と、
(b)段階(a)の生成物から、6個以上の炭素原子を含むオレフィンを10〜50重量%の間で含む、少なくとも1つの炭化水素分画を分離する段階と、
(c)段階(b)で得られた1つまたは複数の炭化水素分画を、コバルト源および1種または複数のアルキルホスフィンをベースとするヒドロホルミル化触媒の存在下、ヒドロホルミル化条件の下で、一酸化炭素および水素と接触させる段階と、
(d)アルコール組成物を回収する段階とを
包含するアルコール組成物を調製する方法を提供する。
(1)C11およびC12n−アルカンを少なくとも30重量%、ならびに直鎖C11およびC12モノオレフィン(すなわち、1−オレフィン、2−オレフィン、および内部オレフィンを含む)を15〜50重量%含む炭化水素ストリーム、または
(2)C13およびC14n−アルカンを少なくとも30重量%、ならびに直鎖C13およびC14モノオレフィンを10〜45重量%含む炭化水素ストリーム
を使用すると非常に有利であることが分かった。
(a)C12およびC13直鎖第1級モノアルコールを、70〜90重量%、好ましくは75〜85重量%、
(b)C12およびC13イソアルコールを、10〜30重量%、好ましくは15〜25重量%
(ただし、C12直鎖第1級アルコール対C13直鎖第1級アルコールの重量比が、0.5〜2.0の範囲にある)
を含むアルコール組成物に関する。
(a)C14およびC15直鎖第1級モノアルコールを、55〜80重量%、好ましくは60〜75重量%、
(b)C14およびC15イソアルコールを20〜45重量%、好ましくは25〜40重量%
(ただし、C14直鎖第1級アルコール対C15直鎖第1級アルコールの重量比が、1.0〜3.0の範囲にある)
を含むアルコール組成物に関する。
Claims (8)
- 1種または複数の第1級モノアルコールを含み、少なくともその60重量%が少なくとも7個の炭素原子を含む直鎖第1級モノアルコールからなる、アルコール組成物を調製する方法であって、
(a)コバルトを含むフィッシャー−トロプシュ触媒の存在下、フィッシャー−トロプシュ反応条件の下で一酸化炭素を水素と反応させる段階と、
(b)段階(a)の生成物から、6個以上の炭素原子を含むオレフィンを10〜45重量%の間で含む、少なくとも1つの炭化水素分画を分離する段階と、
(c)段階(b)で得られた1つまたは複数の炭化水素分画を、コバルト源および置換または非置換のモノホスファビシクロアルカン配位子をベースとするヒドロホルミル化触媒の存在下、ヒドロホルミル化条件の下で、一酸化炭素および水素と接触させる段階と、
(d)アルコール組成物を回収する段階とを
包含するアルコール組成物を調製する方法。 - 段階(a)が、チタニアを含む担体上にコバルトを含む触媒の存在下、125〜350℃の範囲の温度、および絶対圧5〜150barの範囲の圧力で、一酸化炭素を水素と反応させることを含む請求項1に記載の方法。
- 段階(b)中の分離が、蒸留処理を含む請求項1または2に記載の方法。
- 段階(c)への供給原料が、C11およびC12n−アルカンを少なくとも30重量%、ならびに直鎖C11およびC12モノオレフィンを20〜45重量%含む、炭化水素ストリームである請求項1から3のいずれか一項に記載の方法。
- 段階(c)への供給原料が、C13およびC14n−アルカンを少なくとも30重量%、ならびに直鎖C13およびC14モノオレフィンを10〜45重量%含む、炭化水素ストリームである請求項1から3のいずれか一項に記載の方法。
- 段階(c)中の水素対一酸化炭素のモル比が、1.0〜5.0の範囲にある請求項1から5のいずれか一項に記載の方法。
- 段階(d)が第1蒸留処理、けん化、水洗処理、および第2蒸留処理の段階を含む請求項1から6のいずれか一項に記載の方法。
- 段階(d)が、さらに水素化精製処理を含む請求項7に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01305087 | 2001-06-12 | ||
PCT/EP2002/006373 WO2002100806A1 (en) | 2001-06-12 | 2002-06-10 | Process for the preparation of a highly linear alcohol composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2004529201A JP2004529201A (ja) | 2004-09-24 |
JP4302510B2 true JP4302510B2 (ja) | 2009-07-29 |
Family
ID=8182019
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003503577A Expired - Fee Related JP4302510B2 (ja) | 2001-06-12 | 2002-06-10 | 直鎖率の高いアルコール組成物を調製する方法 |
Country Status (14)
Country | Link |
---|---|
US (2) | US6657092B2 (ja) |
EP (1) | EP1395532B1 (ja) |
JP (1) | JP4302510B2 (ja) |
CN (1) | CN1232482C (ja) |
AR (1) | AR034461A1 (ja) |
AT (1) | ATE337284T1 (ja) |
AU (1) | AU2002316973B2 (ja) |
DE (1) | DE60214168T2 (ja) |
GC (1) | GC0000393A (ja) |
MX (1) | MXPA03011243A (ja) |
MY (1) | MY128880A (ja) |
RU (1) | RU2291848C2 (ja) |
WO (1) | WO2002100806A1 (ja) |
ZA (1) | ZA200309194B (ja) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040176655A1 (en) * | 2003-02-05 | 2004-09-09 | Ayoub Paul Marie | Methods of preparing branched alkyl aromatic hydrocarbons |
MY143120A (en) | 2003-02-20 | 2011-03-15 | Shell Int Research | A process for the preparation of detergent compounds |
US6982355B2 (en) * | 2003-08-25 | 2006-01-03 | Syntroleum Corporation | Integrated Fischer-Tropsch process for production of linear and branched alcohols and olefins |
MY139122A (en) * | 2003-10-15 | 2009-08-28 | Shell Int Research | Preparation of branched aliphatic alcohols using a process stream from a dehydrogenation-isomerization unit |
US7335802B2 (en) * | 2003-10-15 | 2008-02-26 | Shell Oil Company | Methods of preparing branched aliphatic alcohols |
AR046754A1 (es) * | 2003-12-11 | 2005-12-21 | Shell Int Research | Proceso de preparacion de una composicion de alcohol alcoxilado |
CN1993309B (zh) * | 2004-08-04 | 2010-11-10 | 埃克森美孚化学专利公司 | C8-c10醇的混合物以及衍生的增塑剂和表面活性剂 |
JP2009506105A (ja) * | 2005-08-31 | 2009-02-12 | サソル テクノロジー (プロプリエタリ) リミテッド | 界面活性剤用アルコールの製造方法 |
CN101310856B (zh) * | 2007-05-24 | 2010-10-13 | 中国科学院大连化学物理研究所 | 一种co加氢直接合成高碳伯醇的催化剂及其制备方法 |
CN103521249B (zh) * | 2012-07-05 | 2016-08-24 | 中国科学院大连化学物理研究所 | 一种用于合成气转化的磷化物催化剂和制备方法及其应用 |
KR102363796B1 (ko) * | 2013-03-07 | 2022-02-16 | 게노마티카 인코포레이티드 | 재조합 숙주 세포에 의해 생성된 지방알코올 조성물들의 하류 공정 |
CN105585433B (zh) * | 2014-10-24 | 2017-12-15 | 中国石油化工股份有限公司 | 醋酸乙烯氢甲酰化合成1,3‑丙二醇的方法 |
RU2602239C1 (ru) * | 2015-07-23 | 2016-11-10 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Способ гидроформилирования олефинов с6-с9 в спирты с7-с10 |
US10625245B2 (en) * | 2016-04-04 | 2020-04-21 | Kao Corporation | Method for producing alcohol |
EP3424895A1 (de) | 2017-07-06 | 2019-01-09 | Rheinisch-Westfälische Technische Hochschule (RWTH) Aachen | Verfahren zur herstellung eines treibstoffes für verbrennungsmotoren |
EP4112169A1 (en) | 2021-07-03 | 2023-01-04 | Studiengesellschaft Kohle mbH | Process for converting synthesis gas to higher alcohols |
CN118265688A (zh) * | 2021-12-06 | 2024-06-28 | 陶氏环球技术有限责任公司 | 包含直链十三烷醇的醇混合物 |
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US3239569A (en) | 1960-07-22 | 1966-03-08 | Shell Oil Co | Hydroformylation of olefins |
US3239571A (en) | 1960-07-22 | 1966-03-08 | Shell Oil Co | Hydroformylation of olefins |
US3420898A (en) | 1965-03-29 | 1969-01-07 | Shell Oil Co | Single stage hydroformylation of olefins to alcohols |
US3501515A (en) | 1965-03-29 | 1970-03-17 | Shell Oil Co | Bicyclic heterocyclic tertiary phosphine-cobalt-carbonyl complexes |
US3400163A (en) | 1965-06-30 | 1968-09-03 | Shell Oil Co | Bicyclic heterocyclic sec- and tert-phosphines |
CA2225615A1 (en) * | 1995-06-29 | 1997-01-16 | Sasol Technology (Proprietary) Limited | Process for producing oxygenated products |
EG21174A (en) * | 1996-04-16 | 2000-12-31 | Procter & Gamble | Surfactant manufacture |
-
2002
- 2002-06-06 MY MYPI20022107A patent/MY128880A/en unknown
- 2002-06-08 GC GCP20022052 patent/GC0000393A/en active
- 2002-06-10 JP JP2003503577A patent/JP4302510B2/ja not_active Expired - Fee Related
- 2002-06-10 AT AT02745373T patent/ATE337284T1/de not_active IP Right Cessation
- 2002-06-10 EP EP02745373A patent/EP1395532B1/en not_active Expired - Lifetime
- 2002-06-10 MX MXPA03011243A patent/MXPA03011243A/es active IP Right Grant
- 2002-06-10 WO PCT/EP2002/006373 patent/WO2002100806A1/en active IP Right Grant
- 2002-06-10 CN CNB028119193A patent/CN1232482C/zh not_active Expired - Fee Related
- 2002-06-10 DE DE60214168T patent/DE60214168T2/de not_active Expired - Lifetime
- 2002-06-10 AU AU2002316973A patent/AU2002316973B2/en not_active Ceased
- 2002-06-10 RU RU2004100303/04A patent/RU2291848C2/ru not_active IP Right Cessation
- 2002-06-11 AR ARP020102192A patent/AR034461A1/es not_active Application Discontinuation
- 2002-06-11 US US10/167,209 patent/US6657092B2/en not_active Expired - Lifetime
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2003
- 2003-07-17 US US10/621,816 patent/US6861450B2/en not_active Expired - Fee Related
- 2003-11-26 ZA ZA200309194A patent/ZA200309194B/en unknown
Also Published As
Publication number | Publication date |
---|---|
US6657092B2 (en) | 2003-12-02 |
US6861450B2 (en) | 2005-03-01 |
MY128880A (en) | 2007-02-28 |
WO2002100806A8 (en) | 2004-04-15 |
EP1395532A1 (en) | 2004-03-10 |
GC0000393A (en) | 2007-03-31 |
AR034461A1 (es) | 2004-02-25 |
MXPA03011243A (es) | 2004-02-27 |
CN1232482C (zh) | 2005-12-21 |
RU2291848C2 (ru) | 2007-01-20 |
EP1395532B1 (en) | 2006-08-23 |
ZA200309194B (en) | 2004-06-09 |
DE60214168T2 (de) | 2007-07-19 |
DE60214168D1 (de) | 2006-10-05 |
AU2002316973B2 (en) | 2007-08-02 |
ATE337284T1 (de) | 2006-09-15 |
US20030073750A1 (en) | 2003-04-17 |
RU2004100303A (ru) | 2005-04-10 |
WO2002100806A1 (en) | 2002-12-19 |
US20040019124A1 (en) | 2004-01-29 |
JP2004529201A (ja) | 2004-09-24 |
CN1516685A (zh) | 2004-07-28 |
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