CA1183481A - Process for making d-fructose - Google Patents
Process for making d-fructoseInfo
- Publication number
- CA1183481A CA1183481A CA000409397A CA409397A CA1183481A CA 1183481 A CA1183481 A CA 1183481A CA 000409397 A CA000409397 A CA 000409397A CA 409397 A CA409397 A CA 409397A CA 1183481 A CA1183481 A CA 1183481A
- Authority
- CA
- Canada
- Prior art keywords
- glucose
- fructose
- mannose
- mannitol
- solution
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/02—Monosaccharides
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K11/00—Fructose
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Seasonings (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
The present invention provides a method for producing D-fructose and D-glucose. The method comprises the steps of epimerizing D-glucose to a mixture of D-glucose and D-mannose, separating the D-glucose from the mixture, hydrogenating the D-mannose in a fixed catalyst bed to provide D-mannitol, oxidizing the D-mannitol to provide a D-fructose solution and crystallizing the solution to provide D fructose crystals.
The present invention provides a method for producing D-fructose and D-glucose. The method comprises the steps of epimerizing D-glucose to a mixture of D-glucose and D-mannose, separating the D-glucose from the mixture, hydrogenating the D-mannose in a fixed catalyst bed to provide D-mannitol, oxidizing the D-mannitol to provide a D-fructose solution and crystallizing the solution to provide D fructose crystals.
Description
~3~
BACKGROUND OF THE INVENTION
This invention relates to a method for commercially producing a sweetener for foodstuffs and more particularly to a method for producing D-fructose.
It has been known that sugars, i.e., D-sugars such as D-glucose, D-fructose and D-saccharose and others have been useful as sweeteners. According to U.S.
Patents 2,753l279 and 2,845,369, the intermediate product, D-mannitol was oxidized to provide D-fructose.
~wever, this process was discontinued since its cost was excessive and impractical for producing the sweetener, D-fructose, commercially.
The production of synthetic sweeteners such as D-sugars has been done commercially. However, since there is a need for producing sugars such as D-fructose on a commercial basis that would be both economical and practical, the present method for producing such sugars is provided.
-The present invention provides a method for producing D-~ruatose and D-glucose. The method comprises the ~teps of epimerizing D-glucose to a mixtuxe o D-ylucose and D-mannose, separating the D-glucose fr~m the m;xtuxe, hydrogenating the D-mannose in a ~ixed catalyst bed to provide D-mannitol, oxidiz-in~ the D~mannitol to provide a D-fructose solution and 3n cr~8tall~zing the solut~on `to provide D-ructose crystals.
BRIEF DESCRIPTION OF THE DR~ING
The present invention will be understood more clearly by considerlng the following description in con~unction with the drawing, wherein:
":
~ ~r~
~3481 FIG. 1 is a flow diagram illustrating the process for producing D-fructose and D-glucose according to the present invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
Referring to FIG. l, there is shown a flow diagram illustratin~ the present process for producing D-fructose and D-glucose. D-fructose is a sweetener for most foodstuffs.
FIG. 1 shows the step-wise process for producing D-fructose and D-glucose. According to the present process, an aqueous solution of D-glucose is first epimerized to a mixture of D-glucose and D~mannose, preferably in a fixed catalyst bed. This mixture is then passed to a fractional crystallizer where the D-glucose is separated from the mixture, i.e., D-mannose, and recycled to the epimerization zone to be further epimerized. After the separation of the D-glucose, the D-mannose is hydrogenated to provide a solution of D-mannitol.
The ~-mannitol, in solution, is then treated with oxygen or a~r in the presence of oxidizing microbes, i.e., Gluconohacter suboxydans which are also referred to as cetobacter suboxydans. The mannitol after being oxygenated, pro~ides a solution of D-fructose which is treated, i.e., crystallized into crystals.
~here may be unoxidized D-mannitol passed with ; 30 the D-~ructose solution to the crystallizer. This unoxidized, i.e., residual, D-mannitol is then recycled to the oxidation zone to be oxidized with that being passed from the hydrogenation zone.
:' ~3~
The catalyst of the fixed bed in which th~
D-glucose is epimerized, is preferably silicotungstic acid on silica gel. There are other catalysts which may be used in this epimerization process which include molybdic acid on silica gel, phosphomolybdic acid on silica gel, and similar derivatives of molybdenum and tungsten, on a silica gel that is preferably acid washed. This same fixed catalyst bed is used in the hydrogenation of D-mannose to D-mannitol.
The epimerization process, where D-mannose is produced, uses a 10 to 70~ aqueous D-glucose solution and most preferably, a 50 to 70% aqueous D-glucose solution at 100-125C., and a pH of 3 to 5 and a reaction time of 30 to 120 minutes. Also, in place of the pure D-glucose, solutions of crude start hydrolyzate can be used for producing the D-mannitol and eventually D-fructose.
In the hydrogenation of D-mannose with the fixed catalyst bed, the hydrogen flow rate is related to the liquid feed rate and by the quantity of catalyst used, as the hydrogen gas flo~ provides for carrying the feed liquid dropleks through the fixed-catalyst type beds to achieve intimate contact with the catalyst particles.
The liquid ~eed rate in the present hydrogenation ranges ~rom about 0.3 to about 10.0 g./hr./g. of catalyst, and preferably from about 0.4 to about 8.0 ~.~hr.~g. of catalysk. ~ccordingly, t:he ratio o~
hydrogen yas to liquid ~eed rate at s~.andard conditions ranges from about 500 tto about 5000 for achieving ~atis~actory conversion of D~mannose to D-mannitol.
'~57' 3gt~31 The aerobic fermenting bacteria include:
Gluconobacter suboxydans (subsp. suboxydans). The amount of suboxydans used is generally related to the amount of D-mannitol being oxidized. This amount ranges from about 20 g to about 80 g./liter reactor ~olume~hr.
The conditions under which the D-mannose is hydrogenated to D-mannitol in the fixed catalyst bed is at a temperature ranging from about 100 to about 150C. and a pressure ranging from about 500 to about 2000 psig hydrogen partial pressure.
D-fructose may be utilized as a sweetening material for foodstuffs of all kinds. The D-fructose is a sweetening agent which is calorific and is twice as sweet as saccharose. Thus, only half as much D-fructose is needed to sweeten foodstuffs.
BACKGROUND OF THE INVENTION
This invention relates to a method for commercially producing a sweetener for foodstuffs and more particularly to a method for producing D-fructose.
It has been known that sugars, i.e., D-sugars such as D-glucose, D-fructose and D-saccharose and others have been useful as sweeteners. According to U.S.
Patents 2,753l279 and 2,845,369, the intermediate product, D-mannitol was oxidized to provide D-fructose.
~wever, this process was discontinued since its cost was excessive and impractical for producing the sweetener, D-fructose, commercially.
The production of synthetic sweeteners such as D-sugars has been done commercially. However, since there is a need for producing sugars such as D-fructose on a commercial basis that would be both economical and practical, the present method for producing such sugars is provided.
-The present invention provides a method for producing D-~ruatose and D-glucose. The method comprises the ~teps of epimerizing D-glucose to a mixtuxe o D-ylucose and D-mannose, separating the D-glucose fr~m the m;xtuxe, hydrogenating the D-mannose in a ~ixed catalyst bed to provide D-mannitol, oxidiz-in~ the D~mannitol to provide a D-fructose solution and 3n cr~8tall~zing the solut~on `to provide D-ructose crystals.
BRIEF DESCRIPTION OF THE DR~ING
The present invention will be understood more clearly by considerlng the following description in con~unction with the drawing, wherein:
":
~ ~r~
~3481 FIG. 1 is a flow diagram illustrating the process for producing D-fructose and D-glucose according to the present invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
Referring to FIG. l, there is shown a flow diagram illustratin~ the present process for producing D-fructose and D-glucose. D-fructose is a sweetener for most foodstuffs.
FIG. 1 shows the step-wise process for producing D-fructose and D-glucose. According to the present process, an aqueous solution of D-glucose is first epimerized to a mixture of D-glucose and D~mannose, preferably in a fixed catalyst bed. This mixture is then passed to a fractional crystallizer where the D-glucose is separated from the mixture, i.e., D-mannose, and recycled to the epimerization zone to be further epimerized. After the separation of the D-glucose, the D-mannose is hydrogenated to provide a solution of D-mannitol.
The ~-mannitol, in solution, is then treated with oxygen or a~r in the presence of oxidizing microbes, i.e., Gluconohacter suboxydans which are also referred to as cetobacter suboxydans. The mannitol after being oxygenated, pro~ides a solution of D-fructose which is treated, i.e., crystallized into crystals.
~here may be unoxidized D-mannitol passed with ; 30 the D-~ructose solution to the crystallizer. This unoxidized, i.e., residual, D-mannitol is then recycled to the oxidation zone to be oxidized with that being passed from the hydrogenation zone.
:' ~3~
The catalyst of the fixed bed in which th~
D-glucose is epimerized, is preferably silicotungstic acid on silica gel. There are other catalysts which may be used in this epimerization process which include molybdic acid on silica gel, phosphomolybdic acid on silica gel, and similar derivatives of molybdenum and tungsten, on a silica gel that is preferably acid washed. This same fixed catalyst bed is used in the hydrogenation of D-mannose to D-mannitol.
The epimerization process, where D-mannose is produced, uses a 10 to 70~ aqueous D-glucose solution and most preferably, a 50 to 70% aqueous D-glucose solution at 100-125C., and a pH of 3 to 5 and a reaction time of 30 to 120 minutes. Also, in place of the pure D-glucose, solutions of crude start hydrolyzate can be used for producing the D-mannitol and eventually D-fructose.
In the hydrogenation of D-mannose with the fixed catalyst bed, the hydrogen flow rate is related to the liquid feed rate and by the quantity of catalyst used, as the hydrogen gas flo~ provides for carrying the feed liquid dropleks through the fixed-catalyst type beds to achieve intimate contact with the catalyst particles.
The liquid ~eed rate in the present hydrogenation ranges ~rom about 0.3 to about 10.0 g./hr./g. of catalyst, and preferably from about 0.4 to about 8.0 ~.~hr.~g. of catalysk. ~ccordingly, t:he ratio o~
hydrogen yas to liquid ~eed rate at s~.andard conditions ranges from about 500 tto about 5000 for achieving ~atis~actory conversion of D~mannose to D-mannitol.
'~57' 3gt~31 The aerobic fermenting bacteria include:
Gluconobacter suboxydans (subsp. suboxydans). The amount of suboxydans used is generally related to the amount of D-mannitol being oxidized. This amount ranges from about 20 g to about 80 g./liter reactor ~olume~hr.
The conditions under which the D-mannose is hydrogenated to D-mannitol in the fixed catalyst bed is at a temperature ranging from about 100 to about 150C. and a pressure ranging from about 500 to about 2000 psig hydrogen partial pressure.
D-fructose may be utilized as a sweetening material for foodstuffs of all kinds. The D-fructose is a sweetening agent which is calorific and is twice as sweet as saccharose. Thus, only half as much D-fructose is needed to sweeten foodstuffs.
Claims (6)
1. A method for producing D-fructose from D-glucose, which comprises the steps of:
a) epimerizing D-glucose to a mixture of D-glucose and D-mannose;
b) separating said D-glucose from the mixture of D-mannose;
c) hydrogenating said D-mannose to provide D-mannitol;
d) oxidizing said D-mannitol to provide a solution of D-fructose; and e) crystallizing said D-fructose solution to provide crystals of D-fructose.
a) epimerizing D-glucose to a mixture of D-glucose and D-mannose;
b) separating said D-glucose from the mixture of D-mannose;
c) hydrogenating said D-mannose to provide D-mannitol;
d) oxidizing said D-mannitol to provide a solution of D-fructose; and e) crystallizing said D-fructose solution to provide crystals of D-fructose.
2. The method according to claim 1, wherein said D-glucose is in a 10 to 70% aqueous solution.
3. The method according to claim 1, wherein the epimerization of said D-glucose takes place in a fixed catalyst bed of silicotungstic acid on silica gel.
4. The method according to claim 1, wherein said D-mannose is hydrogenated in a fixed catalyst bed at a temperature ranging from about 100 to about 150°C.
5. The method according to claim 1, wherein said D-glucose is replaced by a solution of crude starch hydrolyzate.
6. The method according to claim 1, wherein the oxidation of D-mannitol and D-fructose is carried out with an oxygen containing gas in the presence of Gluconobacter suboxydans.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29609581A | 1981-08-26 | 1981-08-26 | |
| US296,095 | 1981-08-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1183481A true CA1183481A (en) | 1985-03-05 |
Family
ID=23140584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000409397A Expired CA1183481A (en) | 1981-08-26 | 1982-08-13 | Process for making d-fructose |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5843991A (en) |
| CA (1) | CA1183481A (en) |
| DE (1) | DE3228883A1 (en) |
| ES (1) | ES8307293A1 (en) |
| FR (1) | FR2512059A1 (en) |
| GB (1) | GB2105336B (en) |
| MX (1) | MX7613E (en) |
| ZA (1) | ZA826053B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4421568A (en) * | 1981-08-26 | 1983-12-20 | Hydrocarbon Research, Inc. | Process for making L-sugars and D-fructose |
| JPH0619293Y2 (en) * | 1984-08-30 | 1994-05-18 | 神鋼電機株式会社 | Brushless motor magnetic pole position detector |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2753279A (en) * | 1954-07-02 | 1956-07-03 | Abbott Lab | Ion exchange purification of fructose solution |
| US2845369A (en) * | 1955-08-29 | 1958-07-29 | Abbott Lab | Ion exchange purification of fructose solution |
| IT1048565B (en) * | 1975-05-15 | 1980-12-20 | Archifar Ind Chim Trentino | AROMATIC AMINAS |
| JPS5277007A (en) * | 1975-12-19 | 1977-06-29 | Towa Kasei Kogyo Kk | Method of producing aqueous hexose and hexoseealcohol containing solution |
| US4421568A (en) * | 1981-08-26 | 1983-12-20 | Hydrocarbon Research, Inc. | Process for making L-sugars and D-fructose |
-
1982
- 1982-08-03 DE DE19823228883 patent/DE3228883A1/en not_active Withdrawn
- 1982-08-13 CA CA000409397A patent/CA1183481A/en not_active Expired
- 1982-08-17 GB GB08223680A patent/GB2105336B/en not_active Expired
- 1982-08-20 MX MX82896U patent/MX7613E/en unknown
- 1982-08-20 ZA ZA826053A patent/ZA826053B/en unknown
- 1982-08-25 JP JP57146296A patent/JPS5843991A/en active Pending
- 1982-08-26 ES ES515286A patent/ES8307293A1/en not_active Expired
- 1982-08-26 FR FR8214665A patent/FR2512059A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5843991A (en) | 1983-03-14 |
| ZA826053B (en) | 1983-07-27 |
| ES515286A0 (en) | 1983-06-01 |
| GB2105336B (en) | 1985-06-12 |
| GB2105336A (en) | 1983-03-23 |
| MX7613E (en) | 1990-03-27 |
| ES8307293A1 (en) | 1983-06-01 |
| FR2512059A1 (en) | 1983-03-04 |
| DE3228883A1 (en) | 1983-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |