WO2009069714A1 - フラン化合物の製造方法 - Google Patents

フラン化合物の製造方法 Download PDF

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Publication number
WO2009069714A1
WO2009069714A1 PCT/JP2008/071579 JP2008071579W WO2009069714A1 WO 2009069714 A1 WO2009069714 A1 WO 2009069714A1 JP 2008071579 W JP2008071579 W JP 2008071579W WO 2009069714 A1 WO2009069714 A1 WO 2009069714A1
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Prior art keywords
compound
furan compound
production
furan
furfural
Prior art date
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PCT/JP2008/071579
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English (en)
French (fr)
Inventor
Miki Sugita
Hideto Tsuji
Toru Okoshi
Original Assignee
Mitsubishi Chemical Corporation
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Publication date
Priority claimed from JP2007311127A external-priority patent/JP5315679B2/ja
Application filed by Mitsubishi Chemical Corporation filed Critical Mitsubishi Chemical Corporation
Priority to CN2008801176329A priority Critical patent/CN101874026B/zh
Publication of WO2009069714A1 publication Critical patent/WO2009069714A1/ja

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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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/42—Platinum
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/58—Platinum group metals with alkali- or alkaline earth metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D307/08—Preparation of tetrahydrofuran
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C07D307/44—Furfuryl alcohol
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    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • 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
    • 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
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/613—10-100 m2/g
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/63—Pore volume
    • B01J35/633—Pore volume less than 0.5 ml/g
    • 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
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • 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
    • B01J37/16—Reducing
    • B01J37/18—Reducing with gases containing free hydrogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Furan Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

　フルフラール化合物からフラン化合物を製造するにあたり、触媒の活性が経時的に低下することを抑制し、安定的にフルフラール化合物を転化せしめて、高効率にフラン化合物を製造する方法を提供する。フラン化合物の製造方法は、フルフラール化合物原料を、Ｚｒ、Ｈｆから選ばれる少なくとも１種の元素、および、８、９、１０族から選ばれる少なくとも１種の金属元素を含有する触媒の存在下で脱カルボニル化反応させる工程を備える。
PCT/JP2008/071579 2007-11-30 2008-11-27 フラン化合物の製造方法 WO2009069714A1 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN2008801176329A CN101874026B (zh) 2007-11-30 2008-11-27 呋喃化合物的制备方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2007-311127 2007-11-30
JP2007311149 2007-11-30
JP2007311127A JP5315679B2 (ja) 2007-11-30 2007-11-30 フラン化合物の製造方法
JP2007-311149 2007-11-30

Publications (1)

Publication Number Publication Date
WO2009069714A1 true WO2009069714A1 (ja) 2009-06-04

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Application Number Title Priority Date Filing Date
PCT/JP2008/071579 WO2009069714A1 (ja) 2007-11-30 2008-11-27 フラン化合物の製造方法

Country Status (2)

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CN (2) CN101874026B (ja)
WO (1) WO2009069714A1 (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101967133A (zh) * 2010-09-10 2011-02-09 西南化工研究设计院 一种糠醛脱羰制呋喃工艺
CN102256956A (zh) * 2008-12-18 2011-11-23 纳幕尔杜邦公司 蒸汽相脱羰基方法
WO2016158706A1 (ja) * 2015-03-27 2016-10-06 三菱化学株式会社 フラン化合物の製造方法及びフルフラール組成物
US10173994B2 (en) 2012-07-03 2019-01-08 Xyleco, Inc. Conversion of biomass

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014061731A1 (ja) * 2012-10-18 2014-04-24 三菱化学株式会社 テトラヒドロフランの製造方法
CA2939397A1 (en) 2014-03-31 2015-10-08 Shell Internationale Research Maatschappij B.V. Process for the production of furan and its derivatives
JP6575126B2 (ja) * 2014-05-08 2019-09-18 三菱ケミカル株式会社 フルフラールの製造方法及びフランの製造方法
CN108467374A (zh) * 2018-02-11 2018-08-31 浙江大学 在固定床反应器中进行糠醛加氢反应制备生物呋喃的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5841828A (ja) * 1981-09-04 1983-03-11 Sumitomo Chem Co Ltd 有機酸ハロゲン化物の脱カルボニル化方法
US4780552A (en) * 1986-09-23 1988-10-25 Basf Aktiengesellschaft Preparation of furan by decarbonylation of furfural
JP2005527516A (ja) * 2002-03-14 2005-09-15 ビーエーエスエフ アクチェンゲゼルシャフト 触媒及びアミンの製造法

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US3007941A (en) * 1959-12-31 1961-11-07 Du Pont Decarbonylation of furfural
CN1095397C (zh) * 2000-11-09 2002-12-04 中国科学院兰州化学物理研究所 糠醛气相脱羰生产呋喃用催化剂

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5841828A (ja) * 1981-09-04 1983-03-11 Sumitomo Chem Co Ltd 有機酸ハロゲン化物の脱カルボニル化方法
US4780552A (en) * 1986-09-23 1988-10-25 Basf Aktiengesellschaft Preparation of furan by decarbonylation of furfural
JP2005527516A (ja) * 2002-03-14 2005-09-15 ビーエーエスエフ アクチェンゲゼルシャフト 触媒及びアミンの製造法

Non-Patent Citations (4)

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Title
DATABASE CAPLUS Database accession no. 1994:56972 *
DATABASE CASREACT Database accession no. 139:118978 *
HU, YAN-PING ET AL.: "Regeneration of Pd-Ni/ g-A1203 catalysts for the gas-phase decarbonylation of furfural", CHANGCHUN GONGYE DAXUE XUEBAO, ZIRAN KEXUEBAN, vol. 26, no. 2, 2005, pages 92 - 95 *
JUNG, K. J. ET AL.: "Furan by decarbonylation of furfural", INFORMATIONS CHIMIE, vol. 283, 1987, pages 135 - 138 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102256956A (zh) * 2008-12-18 2011-11-23 纳幕尔杜邦公司 蒸汽相脱羰基方法
CN102256956B (zh) * 2008-12-18 2016-03-30 纳幕尔杜邦公司 蒸汽相脱羰基方法
CN101967133A (zh) * 2010-09-10 2011-02-09 西南化工研究设计院 一种糠醛脱羰制呋喃工艺
US10173994B2 (en) 2012-07-03 2019-01-08 Xyleco, Inc. Conversion of biomass
US10457656B2 (en) 2012-07-03 2019-10-29 Xyleco, Inc. Conversion of biomass
WO2016158706A1 (ja) * 2015-03-27 2016-10-06 三菱化学株式会社 フラン化合物の製造方法及びフルフラール組成物
US10125109B2 (en) 2015-03-27 2018-11-13 Mitsubishi Chemical Corporation Method for producing furan compound and furfural composition
US10253008B2 (en) 2015-03-27 2019-04-09 Mitsubishi Chemical Corporation Method for producing furan compound and furfural composition

Also Published As

Publication number Publication date
CN101874026B (zh) 2012-11-21
CN102993139B (zh) 2015-09-16
CN102993139A (zh) 2013-03-27
CN101874026A (zh) 2010-10-27

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