US3875140A - Process for the preparation of fructose - Google Patents

Process for the preparation of fructose Download PDF

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Publication number
US3875140A
US3875140A US365356A US36535673A US3875140A US 3875140 A US3875140 A US 3875140A US 365356 A US365356 A US 365356A US 36535673 A US36535673 A US 36535673A US 3875140 A US3875140 A US 3875140A
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US
United States
Prior art keywords
boric acid
fructose
solution
glucose
reaction
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 - Lifetime
Application number
US365356A
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English (en)
Inventor
Sidney Alan Barker
Peter John Somers
Brian William Hatt
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.)
Roche Diagnostics GmbH
Original Assignee
Boehringer Mannheim GmbH
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Filing date
Publication date
Application filed by Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH
Application granted granted Critical
Publication of US3875140A publication Critical patent/US3875140A/en
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Classifications

    • CCHEMISTRY; METALLURGY
    • C13SUGAR INDUSTRY
    • C13KSACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K11/00Fructose
    • HELECTRICITY
    • H02GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
    • H02JCIRCUIT ARRANGEMENTS OR SYSTEMS FOR SUPPLYING OR DISTRIBUTING ELECTRIC POWER; SYSTEMS FOR STORING ELECTRIC ENERGY
    • H02J13/00Circuit arrangements for providing remote indication of network conditions, e.g. an instantaneous record of the open or closed condition of each circuitbreaker in the network; Circuit arrangements for providing remote control of switching means in a power distribution network, e.g. switching in and out of current consumers by using a pulse code signal carried by the network
    • H02J13/00004Circuit arrangements for providing remote indication of network conditions, e.g. an instantaneous record of the open or closed condition of each circuitbreaker in the network; Circuit arrangements for providing remote control of switching means in a power distribution network, e.g. switching in and out of current consumers by using a pulse code signal carried by the network characterised by the power network being locally controlled

Definitions

  • ABSTRACT Fructose is produced by the isomerization of glucose and/or mannose by a process comprising isomerizing the glucose or mannose in an alkali solution containing an aryl boric acid.
  • the present invention relates to a process for the production of fructose by the isomerization of glucose or mannose in alkaline solution.
  • the present invention comprises a process for the isomerization of glucose and/or mannose in alkaline solution, wherein the solution contains an aryl boric acid.
  • the solution contains an aryl boric acid.
  • fructose yields of up to and beyond 80% can be obtained.
  • the boric acid there can be used, for example, phenyl boric acid, naphthyl boric acid, alkoxyphenyl boric acids, such as 4-methoxyphenyl boric acid, nitrophenyl boric acids or sulfonated phenyl or naphthyl boric acids.
  • the process can be carried out especially advantageously when the aryl boric acid is a component of an insoluble organic polymer.
  • Such insoluble polymers can be obtained, for example, by polymerizing a vinylphenyl boric acid or a derivative thereof with itself or with styrene or a similar compound or by fixing an aryl boric acid, via a further substituent, on to a reactive carricr material, for example, by fixing a sulfonylphenyl boric acid on to an anion exchanger resin.
  • the process according to the present invention can be carried out with the use of glucose solutions with a concentration of up to or it is especially advantageous to use 20-25% glucose solutions.
  • glucose solutions with a concentration of up to or it is especially advantageous to use 20-25% glucose solutions.
  • pure glucose there can also be used appropriate crude starch hydrolyzates or invert sugar solutions from which a part of the fructose has been removed in known manner.
  • the reaction temperature used is usually between about 20 and 80C and preferably between and C. In the case of higher temperatures, the decomposition of the fructose and of the aryl boric acids becomes more noticeable as a disturbing side reaction and, at comparatively low temperatures, the rate of the reaction is, as is to be expected, lower so that the reaction is uneconomic.
  • the reaction solution should contain about l/2 to 1 mole of aryl boric acid in order to bring about a maximum formation of fructose.
  • the yield of fructose is impaired and, when using higher amounts of aryl boric acid, the rate of reaction drops very considerably, which is surprising and which naturally impairs the economy of the process.
  • the .separation of the fructose formed from the reaction solution can be carried out in known manner, for example, by separation by means of an ion exchanger or by precipitation of the fructose from a neutral solution in the form of calcium fructosate.
  • the aryl boric acid is added to the reaction solution in the form of a component of an insoluble polymer, the fructose formed is preponderantly also fixed in complex form on the resin and can be removed with the resin from the reaction solution.
  • dilute hydrochloric acid there is obtained a fructose-enriched solution which can then be further worked up in known manner.
  • Process as claimed in claim 4 wherein the process is carried out at a temperature of between and 6.
US365356A 1972-06-15 1973-05-30 Process for the preparation of fructose Expired - Lifetime US3875140A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2229064A DE2229064A1 (de) 1972-06-15 1972-06-15 Verfahren zur herstellung von fruktose

Publications (1)

Publication Number Publication Date
US3875140A true US3875140A (en) 1975-04-01

Family

ID=5847774

Family Applications (1)

Application Number Title Priority Date Filing Date
US365356A Expired - Lifetime US3875140A (en) 1972-06-15 1973-05-30 Process for the preparation of fructose

Country Status (5)

Country Link
US (1) US3875140A (de)
AT (1) AT329472B (de)
DE (1) DE2229064A1 (de)
FR (1) FR2189512B1 (de)
GB (1) GB1369185A (de)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2627111A1 (de) * 1975-06-17 1976-12-30 Ici Ltd Verfahren zur umsetzung von aldose oder aldosederivaten zu ketose oder ketosederivaten
US4096036A (en) * 1976-06-15 1978-06-20 Standard Brands Incorporated Method for the separation of water soluble polyols
US4173558A (en) * 1977-06-30 1979-11-06 Am International, Inc. Non-aqueous polymeric dispersion alkyl methacrylate copolymers in mixtures of organic solvents and glossy coatings produced therefrom
US4173559A (en) * 1977-06-30 1979-11-06 Am International, Inc. Non-aqueous polymeric dispersion of alkyl methacrylate and alkyl acrylate copolymers in mixtures of cyclohexane and alcohols and matte coatings produced therefrom
US4199374A (en) * 1978-12-22 1980-04-22 Chimicasa Gmbh Process of preparing crystalline fructose from high fructose corn syrup
US4199373A (en) * 1979-04-13 1980-04-22 Chimicasa Gmbh Process for the manufacture of crystalline fructose
US4273922A (en) * 1980-03-21 1981-06-16 The United States Of America As Represented By The Secretary Of Agriculture Ketose sugars from aldose sugars
US4663449A (en) * 1982-11-16 1987-05-05 Imperial Chemical Industries Plc Process for effecting aldose to ketose conversion
US5230742A (en) * 1987-02-02 1993-07-27 A. E. Staley Manufacturing Co. Integrated process for producing crystalline fructose and high-fructose, liquid-phase sweetener
US5234503A (en) * 1987-02-02 1993-08-10 A.E. Saley Manufacturing Co. Integrated process for producing crystalline fructose and a high-fructose, liquid-phase sweetener
US5350456A (en) * 1987-02-02 1994-09-27 A. E. Staley Manufacturing Company Integrated process for producing crystalline fructose and a high fructose, liquid-phase sweetener
US5656094A (en) * 1987-02-02 1997-08-12 A.E. Staley Manufacturing Company Integrated process for producing crystalline fructose and a high-fructose, liquid phase sweetener
US20100204651A1 (en) * 2009-02-06 2010-08-12 Mark Stringham Automatic safety occluder

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2746889A (en) * 1954-07-27 1956-05-22 Staley Mfg Co A E Interconversion of sugars using anion exchange resins
US2818851A (en) * 1956-02-07 1958-01-07 Joseph X Khym Separation and analysis of polyhydroxy substances
US3431253A (en) * 1966-09-06 1969-03-04 Us Army Fructose formation from glucose
US3432345A (en) * 1966-04-07 1969-03-11 Union Starch & Refining Co Inc Production of fructose from dextrose
US3514327A (en) * 1967-09-27 1970-05-26 Us Army Isomerization of glucose,maltose,and lactose with amino compounds
US3558355A (en) * 1968-07-12 1971-01-26 Eisai Co Ltd Process for enhancement of sweetness of sugars
US3684574A (en) * 1970-04-20 1972-08-15 Anheuser Busch Method of producing sweet syrup by resin isomerization of dextrose syrup

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2746889A (en) * 1954-07-27 1956-05-22 Staley Mfg Co A E Interconversion of sugars using anion exchange resins
US2818851A (en) * 1956-02-07 1958-01-07 Joseph X Khym Separation and analysis of polyhydroxy substances
US3432345A (en) * 1966-04-07 1969-03-11 Union Starch & Refining Co Inc Production of fructose from dextrose
US3431253A (en) * 1966-09-06 1969-03-04 Us Army Fructose formation from glucose
US3514327A (en) * 1967-09-27 1970-05-26 Us Army Isomerization of glucose,maltose,and lactose with amino compounds
US3558355A (en) * 1968-07-12 1971-01-26 Eisai Co Ltd Process for enhancement of sweetness of sugars
US3684574A (en) * 1970-04-20 1972-08-15 Anheuser Busch Method of producing sweet syrup by resin isomerization of dextrose syrup

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2627111A1 (de) * 1975-06-17 1976-12-30 Ici Ltd Verfahren zur umsetzung von aldose oder aldosederivaten zu ketose oder ketosederivaten
US4096036A (en) * 1976-06-15 1978-06-20 Standard Brands Incorporated Method for the separation of water soluble polyols
US4173558A (en) * 1977-06-30 1979-11-06 Am International, Inc. Non-aqueous polymeric dispersion alkyl methacrylate copolymers in mixtures of organic solvents and glossy coatings produced therefrom
US4173559A (en) * 1977-06-30 1979-11-06 Am International, Inc. Non-aqueous polymeric dispersion of alkyl methacrylate and alkyl acrylate copolymers in mixtures of cyclohexane and alcohols and matte coatings produced therefrom
US4199374A (en) * 1978-12-22 1980-04-22 Chimicasa Gmbh Process of preparing crystalline fructose from high fructose corn syrup
US4199373A (en) * 1979-04-13 1980-04-22 Chimicasa Gmbh Process for the manufacture of crystalline fructose
US4273922A (en) * 1980-03-21 1981-06-16 The United States Of America As Represented By The Secretary Of Agriculture Ketose sugars from aldose sugars
JPS57114597A (en) * 1980-03-21 1982-07-16 Us Agriculture Manufacture of ketose sugar
JPH0132833B2 (de) * 1980-03-21 1989-07-10 Us Agriculture
US4663449A (en) * 1982-11-16 1987-05-05 Imperial Chemical Industries Plc Process for effecting aldose to ketose conversion
US5230742A (en) * 1987-02-02 1993-07-27 A. E. Staley Manufacturing Co. Integrated process for producing crystalline fructose and high-fructose, liquid-phase sweetener
US5234503A (en) * 1987-02-02 1993-08-10 A.E. Saley Manufacturing Co. Integrated process for producing crystalline fructose and a high-fructose, liquid-phase sweetener
US5350456A (en) * 1987-02-02 1994-09-27 A. E. Staley Manufacturing Company Integrated process for producing crystalline fructose and a high fructose, liquid-phase sweetener
US5656094A (en) * 1987-02-02 1997-08-12 A.E. Staley Manufacturing Company Integrated process for producing crystalline fructose and a high-fructose, liquid phase sweetener
US20100204651A1 (en) * 2009-02-06 2010-08-12 Mark Stringham Automatic safety occluder

Also Published As

Publication number Publication date
AT329472B (de) 1976-05-10
GB1369185A (en) 1974-10-02
ATA523873A (de) 1975-07-15
FR2189512A1 (de) 1974-01-25
FR2189512B1 (de) 1977-02-11
DE2229064A1 (de) 1973-12-20

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