WO1996040609A1 - Production of levulinic acid from carbohydrate-containing materials - Google Patents

Production of levulinic acid from carbohydrate-containing materials Download PDF

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Publication number
WO1996040609A1
WO1996040609A1 PCT/US1996/007231 US9607231W WO9640609A1 WO 1996040609 A1 WO1996040609 A1 WO 1996040609A1 US 9607231 W US9607231 W US 9607231W WO 9640609 A1 WO9640609 A1 WO 9640609A1
Authority
WO
WIPO (PCT)
Prior art keywords
reactor
carbohydrate
seconds
levulinic acid
containing material
Prior art date
Application number
PCT/US1996/007231
Other languages
English (en)
French (fr)
Inventor
Stephen W. Fitzpatrick
Original Assignee
Biofine Incorporated
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 Biofine Incorporated filed Critical Biofine Incorporated
Priority to EP96914708A priority Critical patent/EP0873294B1/en
Priority to AU57985/96A priority patent/AU5798596A/en
Priority to CA002223600A priority patent/CA2223600C/en
Priority to DE69620240T priority patent/DE69620240T2/de
Publication of WO1996040609A1 publication Critical patent/WO1996040609A1/en
Priority to NO975727A priority patent/NO308464B1/no

Links

Classifications

    • 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
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48—Furfural
    • C07D307/50—Preparation from natural products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides

Definitions

  • Examples 4 and 5 pertain to conversion of a partially or non-bleached kraft paper sludge.
  • the cellulose content of this sludge has been measured to be 80% by weight on average. That is, 100 lbs of bone dry sludge contains 80 lbs of cellulose which is available for conversion to levulinic acid.
  • Example 6 pertains to conversion of raw wood flour. The cellulose content of this has been measured to be, on average, 42% by weight. That is, 100 lbs of bone dry sludge contains 42 lbs of cellulose which is available for conversion to levulinic acid.
  • EXAMPLE 4 1.02 liters per minute of a 1.0% by weight slurry of paper sludge originating from a non-bleached Kraft pulping process containing 1.15% by weight of the aqueous portion sulfuric acid is fed to the reactor system.
  • the first stage tubular reaction is fifteen feet in length and 0.41 inches in inside diameter.
  • High pressure steam is injected into the process stream at an average rate of 0.476 liters per minute (condensed volume) as it passes into the tubular reactor.
  • the residence time of the reaction mixture in the first stage tubular reactor is 14 seconds.
  • the mixture passes through the pressure let ⁇ down valve and flashes directly into the second stage reactor vessel via the dip tube.
  • the second stage reactor is a 10 inch I.D.
  • the liquid product outflow containing levulinic acid was measured at 1.34 liters per minute and the vent outflow was measured at 0.02 liters per minute after condensation.
  • the levulinic acid and glucose concentration in the liquid outflow was measured at steady state after three and a half hours of operation.
  • the yield of levulinic acid was calculated to be 71% of theoretical. No levulinic acid was measured in the vent stream.
  • EXAMPLE 6 0.70 liters per minute of a 10% by weight slurry of hardwood flour containing 5.0% by weight of the aqueous portion sulfuric acid is fed to the reactor system.
  • the first stage tubular reactor is fifteen feet in length and 0.41 inches in inside diameter. High pressure steam is injected into the process stream at an average rate of 0.65 liters per minute (condensed volume) as it passes into the tubular reactor.
  • the residence time of the reaction mixture in the first stage tubular reactor is 15.7 seconds.
  • the mixture passes through the pressure let-down valve and flashes directly into the second stage reactor vessel via the dip tube.
  • the second stage reactor is a 10 inch I.D. (Schedule 20 pipe section) vessel of overall length 27 inches.
  • the liquid product outflow containing levulinic acid was measured at 1.15 liters per minute and the vent outflow was measured at 0.23 liters per minute after condensation.
  • the levulinic acid concentration in the liquid outflow was measured by analysis to be 1.05% at steady state.
  • the product outflow from the reactor system was therefore calculated to be 0.0121 kg per minute representing a yield of levulinic acid of 62% of theoretical.
  • a small quantity (0.000069 Kg per min) of levulinic acid was measured in the vent stream this was accounted for as additional yield.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/US1996/007231 1995-06-07 1996-05-17 Production of levulinic acid from carbohydrate-containing materials WO1996040609A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP96914708A EP0873294B1 (en) 1995-06-07 1996-05-17 Production of levulinic acid from carbohydrate-containing materials
AU57985/96A AU5798596A (en) 1995-06-07 1996-05-17 Production of levulinic acid from carbohydrate-containing ma terials
CA002223600A CA2223600C (en) 1995-06-07 1996-05-17 Production of levulinic acid from carbohydrate-containing materials
DE69620240T DE69620240T2 (de) 1995-06-07 1996-05-17 Herstellung von levulinsäure aus kohlenhydrathaltigen materialien
NO975727A NO308464B1 (no) 1995-06-07 1997-12-05 Fremstilling av levulinsyre fra karbohydratholdige materialer

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/475,630 US5608105A (en) 1995-06-07 1995-06-07 Production of levulinic acid from carbohydrate-containing materials
US08/475,630 1995-06-07

Publications (1)

Publication Number Publication Date
WO1996040609A1 true WO1996040609A1 (en) 1996-12-19

Family

ID=23888434

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/007231 WO1996040609A1 (en) 1995-06-07 1996-05-17 Production of levulinic acid from carbohydrate-containing materials

Country Status (8)

Country Link
US (1) US5608105A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP0873294B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU5798596A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA2223600C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE69620240T2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IN (1) IN185298B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NO (1) NO308464B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO1996040609A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

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US7378549B2 (en) 2004-01-26 2008-05-27 Shell Oil Company Process for the reactive extractive extraction of levulinic acid
RU2339612C1 (ru) * 2007-07-25 2008-11-27 Институт химии и химической технологии СО РАН Способ получения левулиновой кислоты кислотно-каталитической конверсией сахарозы
US7501062B2 (en) 2005-02-22 2009-03-10 Shell Oil Company Process for permeation enhanced reactive extraction of levulinic acid
CN102030646A (zh) * 2010-11-18 2011-04-27 郑州大学 一种纤维素类物质水解直接转化生成乙酰丙酸乙酯的工艺
US8053468B2 (en) 2005-11-22 2011-11-08 Segetis, Inc. Glycerol levulinate ketals and their use
US8138371B2 (en) 2009-03-11 2012-03-20 Biofine Technologies Llc Production of formic acid
WO2012131027A1 (en) 2011-04-01 2012-10-04 Dsm Ip Assets B.V. Process for the preparation of alkanoic acid esters in a carbonylation process using palladium bidentate biphosphate ligands
WO2012131028A1 (en) 2011-04-01 2012-10-04 Dsm Ip Assets B.V. Process to produce adipic acid and diesters thereof in a carbonylation process using palladium bidentate biphosphate ligands
EP2537840A1 (en) 2011-06-21 2012-12-26 DSM IP Assets B.V. Process to produce valerolactone from levulinic acid
EP2573064A1 (en) 2011-09-23 2013-03-27 DSM IP Assets B.V. Process to produce alkenoic acid esters from lactones
WO2013092408A1 (en) 2011-12-20 2013-06-27 Dsm Ip Assets B.V. Process to produce alkenoic acid esters from lactones
WO2013107904A1 (en) 2012-01-19 2013-07-25 Dsm Ip Assets B.V. Process to produce alkanoic acid esters in a carbonylation process using lewis acids as acid promotor
US8575367B2 (en) 2008-09-25 2013-11-05 Segetis, Inc. Ketal ester derivatives
CN104311411A (zh) * 2014-09-15 2015-01-28 淮阴师范学院 多级酸水解制备乙酰丙酸的方法
US9073841B2 (en) 2012-11-05 2015-07-07 Segetis, Inc. Process to prepare levulinic acid
US10618864B2 (en) 2011-11-23 2020-04-14 Gfbiochemicals Ip Assets B.V. Process to prepare levulinic acid

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US7378549B2 (en) 2004-01-26 2008-05-27 Shell Oil Company Process for the reactive extractive extraction of levulinic acid
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US8492433B2 (en) 2005-11-22 2013-07-23 Segetis, Inc. Glycerol levulinate ketals and their use in the manufacture of polyurethanes, and polyurethanes formed therefrom
US8053468B2 (en) 2005-11-22 2011-11-08 Segetis, Inc. Glycerol levulinate ketals and their use
US8906961B2 (en) 2005-11-22 2014-12-09 Segetis, Inc. Glycerol levulinate ketals and their use in the manufacture of polyurethanes, and polyurethanes formed therefrom
US8178701B2 (en) 2005-11-22 2012-05-15 Segetis, Inc. Glycerol levulinate ketals and their use
RU2339612C1 (ru) * 2007-07-25 2008-11-27 Институт химии и химической технологии СО РАН Способ получения левулиновой кислоты кислотно-каталитической конверсией сахарозы
US9206275B2 (en) 2008-09-25 2015-12-08 Segetis, Inc. Ketal ester derivatives
US8575367B2 (en) 2008-09-25 2013-11-05 Segetis, Inc. Ketal ester derivatives
US8765998B2 (en) 2009-03-11 2014-07-01 Biofine Technology, Llc Production of formic acid
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CA2223600C (en) 2004-02-10
DE69620240T2 (de) 2002-11-14
AU5798596A (en) 1996-12-30
NO308464B1 (no) 2000-09-18
DE69620240D1 (de) 2002-05-02
NO975727D0 (no) 1997-12-05
US5608105A (en) 1997-03-04
EP0873294B1 (en) 2002-03-27
IN185298B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 2000-12-23
NO975727L (no) 1998-02-04
CA2223600A1 (en) 1996-12-19
EP0873294A1 (en) 1998-10-28
EP0873294A4 (en) 1999-05-26

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