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GB627293A - Improvements in and relating to the hydrogenation of furfural - Google Patents

Improvements in and relating to the hydrogenation of furfural

Info

Publication number
GB627293A
GB627293A GB597646A GB597646A GB627293A GB 627293 A GB627293 A GB 627293A GB 597646 A GB597646 A GB 597646A GB 597646 A GB597646 A GB 597646A GB 627293 A GB627293 A GB 627293A
Authority
GB
United Kingdom
Prior art keywords
aluminium
catalyst
cobalt
copper
furfural
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
Application number
GB597646A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB597646A priority Critical patent/GB627293A/en
Priority to DE1948P0000589 priority patent/DE827804C/en
Publication of GB627293A publication Critical patent/GB627293A/en
Expired legal-status Critical Current

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
    • 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
    • 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
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • 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
    • B01J25/00—Catalysts of the Raney type
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B01J27/232—Carbonates
    • 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

Landscapes

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

Abstract

Furfural is hydrogenated continuously in the liquid phase at a raised pressure in the presence of a foraminate copper or foraminate cobalt catalyst to yield, according to the conditions, furfuryl alcohol, tetrahydrofurfuryl alcohol, 1 : 2- and 1 : 5-pentanediols and pentanols. Suitable catalysts are obtainable, as described in Specifications 611,987 and 621,749, by alloying cobalt or copper with a metal of greater solubility in acid or alkali, and treating the alloy in granule form with an acid or alkaline solution, according to the alloying metal used. Suitable alloying metals are aluminium, zinc and silicon. The catalysts may be used in alkalised or unalkalised form and the alkali, if used, may be present in the catalyst or included in the feed; alkalies derived from alkali or alkaline-earth metals or magnesium are suitable. Specified catalysts are obtained by treating a granulated 55 : 45 copper-aluminium or 30 : 70 cobalt-aluminium alloy with dilute caustic soda at about 100 DEG C. p until 20 per cent of the aluminium content has been removed. Examples of the use of the catalysts are given, and Specification 605,922 also is referred to.ALSO:Furfural is hydrogenated continuously in the liquid phase at a raised pressure in the presence of a foraminate copper or foraminate cobalt catalyst to yield, according to the conditions, furfuryl alcohol, tegrahydrofurfuryl alcohol, 1 : 2- and 1 : 5-pentanediols and pentanols. These products are obtained at successively increasing temperatures, but the temperature necessary in any particular case depends on the nature and age of the catalyst, a higher temperature being required as the catalyst ages. Suitable catalysts are obtainable as described in Specifications 611,987, [Group III], and 621,749, by alloying cobalt or copper with a metal of greater solubility in acid or alkali, and treating the alloy in granule form with an acid or alkaline solution, according to the alloying metal used. Suitable alloying metals are aluminium, zinc and silicon. The catalysts may be used in alkalised or unalkalised form and the alkali, if used, may be present in the catalyst or included in the feed; alkalies derived from alkali or alkaline-earth metals or magnesium are suitable. Specified catalysts are obtained by treating a granulated 55 : 45 copper-aluminium or 30 : 70 cobalt-aluminium alloy with dilute caustic soda at about 100 DEG C. until 20 per cent of the aluminium content has been removed. In examples of the use of a foraminate cobalt-aluminium catalyst; (1) furfural at 15 DEG C. and 250 atm. yields furfuryl alcohol; (2) a mixture of equal parts of furfural and tetrahydrofurfuryl alcohol at 50 DEG C. and 250 atm. yields substantially pure tetrahydrofurfuryl alcohol. In examples of the use of a foraminate copper-aluminium catalyst; (3) furfural at 80 DEG C. and 250 atm. yields furfuryl alcohol; (4) furfural at 120 DEG C. and 250 atm. yields a mixture of 1 : 2- and 1 : 5-pentanediols while at 150 DEG C. some pentanols also are obtained. The use of pressures of 50-400 atm. is mentioned, and Specification 605,922 also is referred to.
GB597646A 1946-02-26 1946-02-26 Improvements in and relating to the hydrogenation of furfural Expired GB627293A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB597646A GB627293A (en) 1946-02-26 1946-02-26 Improvements in and relating to the hydrogenation of furfural
DE1948P0000589 DE827804C (en) 1946-02-26 1948-11-25 Process for the hydrogenation of furfural

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB597646A GB627293A (en) 1946-02-26 1946-02-26 Improvements in and relating to the hydrogenation of furfural

Publications (1)

Publication Number Publication Date
GB627293A true GB627293A (en) 1949-08-05

Family

ID=9806125

Family Applications (1)

Application Number Title Priority Date Filing Date
GB597646A Expired GB627293A (en) 1946-02-26 1946-02-26 Improvements in and relating to the hydrogenation of furfural

Country Status (2)

Country Link
DE (1) DE827804C (en)
GB (1) GB627293A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2768978A (en) * 1952-08-28 1956-10-30 Du Pont Continuous process for making 1, 5-pentanediol from tetrahydrofurfuryl alcohol
US2768979A (en) * 1952-07-10 1956-10-30 Du Pont Production of 1, 5-pentanediol from furfural
CN102675260A (en) * 2012-05-30 2012-09-19 山东一诺生化科技有限公司 Continuous preparation method of tetrahydrofurfuryl alcohol
CN102911011A (en) * 2011-08-03 2013-02-06 中国科学院大连化学物理研究所 Method for preparing 1,5-pentadiol by means of selective hydrogenolysis of tetrahydrofurfuryl alcohol
CN102924232A (en) * 2012-10-19 2013-02-13 珠海凯美科技有限公司 Method for producing 1,2-pentadiol in one-step hydrogenation by furaldehyde
CN102942448A (en) * 2012-12-10 2013-02-27 南京工业大学 Method for continuously preparing 1, 5-pentanediol from tetrahydrofurfuryl alcohol
WO2013073705A1 (en) * 2011-11-18 2013-05-23 宇部興産株式会社 Method for producing high-purity 1,5-pentanediol
KR101432638B1 (en) * 2012-12-12 2014-09-22 한국화학연구원 A PROCESS FOR PREPARING 1,5-PENTANEDIOL AND δ-VALEROLACTONE FROM TETRAHYDROFURFURYL ALCOHOL

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE918325C (en) * 1952-04-29 1954-09-23 Glanzstoff Ag Process for the hydrogenation of tetrahydrofurfuryl alcohol
WO2012152849A1 (en) * 2011-05-09 2012-11-15 Symrise Ag Method for producing 1-2-pentanediol
WO2015174249A1 (en) * 2014-05-16 2015-11-19 宇部興産株式会社 Method for producing 1,2-pentanediol using biomass starting material and use thereof

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2768979A (en) * 1952-07-10 1956-10-30 Du Pont Production of 1, 5-pentanediol from furfural
US2768978A (en) * 1952-08-28 1956-10-30 Du Pont Continuous process for making 1, 5-pentanediol from tetrahydrofurfuryl alcohol
CN102911011A (en) * 2011-08-03 2013-02-06 中国科学院大连化学物理研究所 Method for preparing 1,5-pentadiol by means of selective hydrogenolysis of tetrahydrofurfuryl alcohol
WO2013073705A1 (en) * 2011-11-18 2013-05-23 宇部興産株式会社 Method for producing high-purity 1,5-pentanediol
CN103906726A (en) * 2011-11-18 2014-07-02 宇部兴产株式会社 Method for producing high-purity 1,5-pentanediol
US8940946B2 (en) 2011-11-18 2015-01-27 Ube Industries, Ltd. Method for producing high-purity 1,5-pentanediol
CN102675260A (en) * 2012-05-30 2012-09-19 山东一诺生化科技有限公司 Continuous preparation method of tetrahydrofurfuryl alcohol
CN102924232A (en) * 2012-10-19 2013-02-13 珠海凯美科技有限公司 Method for producing 1,2-pentadiol in one-step hydrogenation by furaldehyde
CN102924232B (en) * 2012-10-19 2014-09-17 珠海凯美科技有限公司 Method for producing 1,2-pentadiol in one-step hydrogenation by furaldehyde
CN102942448A (en) * 2012-12-10 2013-02-27 南京工业大学 Method for continuously preparing 1, 5-pentanediol from tetrahydrofurfuryl alcohol
KR101432638B1 (en) * 2012-12-12 2014-09-22 한국화학연구원 A PROCESS FOR PREPARING 1,5-PENTANEDIOL AND δ-VALEROLACTONE FROM TETRAHYDROFURFURYL ALCOHOL

Also Published As

Publication number Publication date
DE827804C (en) 1952-01-14

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