CA1150655A - Process for making glucosone - Google Patents
Process for making glucosoneInfo
- Publication number
- CA1150655A CA1150655A CA000382228A CA382228A CA1150655A CA 1150655 A CA1150655 A CA 1150655A CA 000382228 A CA000382228 A CA 000382228A CA 382228 A CA382228 A CA 382228A CA 1150655 A CA1150655 A CA 1150655A
- Authority
- CA
- Canada
- Prior art keywords
- zone
- hydrogen peroxide
- glucose
- alkene
- glucosone
- 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
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
PROCESS FOR MAKING GLUCOSONE
ABSTRACT OF THE DISCLOSURE
Disclosed are methods of producing glucosone which comprises enzymatically oxidizing glucose with glucose-2-oxidase in a first: zone and separating the concomitantly produced hydrogen peroxide from said first zone through a semi-permeable membrane into a second zone wherein an alkene is reacted with said hydrogen peroxide to form oxygenated products of said alkene, said membrane being permeable only to compounds of a molecular weight of less than about 100.
ABSTRACT OF THE DISCLOSURE
Disclosed are methods of producing glucosone which comprises enzymatically oxidizing glucose with glucose-2-oxidase in a first: zone and separating the concomitantly produced hydrogen peroxide from said first zone through a semi-permeable membrane into a second zone wherein an alkene is reacted with said hydrogen peroxide to form oxygenated products of said alkene, said membrane being permeable only to compounds of a molecular weight of less than about 100.
Description
PROCESS FOR ~ KING GLUCOSONE
This invention is concerned with a new and useful process for the prttl~ t;on of ~lucosone and m^re particulall for the production glucosone from which food-grade fructose 5 can be obtained.
Colr~nercial methods for the production of fructose, a commercially important sweetner, primarily involve a two-step process, the first, hydrolysis of a polysaccharide such as starch to produce glucose and the second, isomerization of the 10 so-produced glucose to form fructose. The latter step, as is well-known, produces a mixture of glucose and fructose from which it is difficult to separate the desired product, fructose. The commercial separation method involves the use of crystallization techniques which are costly and time-consuming.
15 More detailed description of the various methods of isomerizing glucose can be found in the literature, e.g. U.S. Patent 3,788,945, and 3,616,221.
Glucose can also be converted to fructose by the action of an enzyme, designated glucose-2-oxidase, to form 20 glucosone (D-arabino-2-hexosulose) which in turn can be re-duced to fructose with zinc and acetic acid ~Folia Micriobiol.
23, 292-298 (1978) and Czechoslovakian Patent No. 175897 to Volc et al.].
The reaction of glucose-2-oxidase with glucose to 25 produce glucosone also yields hydrogen peroxide in equimolar amount. The use of the so-produced hydrogen peroxide in the conversion of alkenes to corresponding halohydrins and epoxides has been proposed in European Patent Application 7176. In the published application, the in situ formation of hydrogen 30 peroxide is proposed by inclusion of glucose-2-oxidase and glucose in the reaction mixture which includes a halogenating ~ '.
.
.
, .
:
: : , . . :
6~5 enzyme and a source of inorganic halide into which the selected alkene is to be introduced. me disclosure of the European patent application further indicates that the glucosone product of the enzymatic oxidation of glucose can be converted to fructose by simple chemical hydrogenation.
However, fructose produced by the said process can be contaminated with significant amounts of by-products from both the enzymatic conversion of glucose ar.d the alkene conversion reaction. In particular, the latter reaction produces halohydrins and alkylene oxides, e.g. ethylene oxide, which are highly toxic material even at levels in the region of parts per million. mus, fructose produced by such a process will require careful and costly purification to attain food-grade purity. Further, the potential for contamination of fructose by virtue of secondary reactions during the initial processing state is quite high due to the highly reactive products, halohydrins and alkyleneoxides, and substantial purification procedures are required to assure the high level purity required for food-grade fructose.
SUWMARY QF THE INVENTION
This invention provides a method for the production of glucosone by enzymatic oxidation of glucose to glucosone in a reaction zone from which hydrogen peroxide is removed by use of a hydrogen peroxide-permeable m~mbrane into a second reaction zone where the hydrogen peroxide is reacted with an alkene to convert the alkene to an oxidation product.
In accordance with one embodiment of the invention, the alkene is converted to a glycol by reaction with hydrogen peroxide. mis reaction is catalyzed by os~ium, vanadium or chromium oxide or by ultraviolet light in accordance with the procedure described J.A.C.S. 58, 1302 (1936); 59, 543, 2342, 2345 (1937), .~
' .' ' ~ - .
- ,:
1 In accordance with a second embodiment of the inven-tion, the alkene is converted to a halohydrin and then to an alkylene oxide or glycol corresponding to the ~ri gi nAl ~l ken~.
reactant by reaction with hydrogen peroxide, a halogenating 5enzyme and a halide ion source, to form the halohydrin which is then converted to an epoxide or glycol, by the methods described in European patent app:Lication 7176.
The membranes employed in the present process are for the prupose of establishing two separate zones and per-lOmitting migration of hydrogen peroxide from the first to thesecond zone. The membranes therefore should be of suitable pore size to selectively permit hydrogen peroxide migration, but to preclude passage of larger molecules in the first reaction zone. Such membranes are readily available commercially and 15can be defined in terms of the molecular weight of solute particles to pass through the membrane. In the present inven-tion, membranes which permit substances of a molecular weight of less than about 100 are to be used, and preferably less than 50.
The migration or passage of hydrogen peroxide through the aforesaid membrane is accomplished through establishment of an equilibrium predicated on the relative concentrations of H202 on each side of the membrane. As the concentration of hydrogen peroxide in the first zone increases, the H202 25tends to migrate to the secon zone until equilibriu~ is rees-stablished. The reaction with an alkene in the second zone increases the rate of flow of hydrogen peroxide through the membrane by offsetting the equilibrium in the direction of the second zone, 3o .
' ' ~ ' ' -- ~ .. ..
.-1 Employing the present process results in considerable advantage particularly in the further processing of glucosone to fructose. The migration of hydr~g~n p~roxlde from the flrst reaction zone of course affects the rate of the enzymatic oxi-sdation of glucose so that the reaction tends to be more complete and the reaction times can be shorter than normally required.
Further, the first reaction zone is essentially free of con-taminants that will accumulate primarily in the second reaction zone where the so produced hydrogen peroxide is reacted. The glucosone solution produced in the first reaction zone can be used as such in the hydrogenation step or can be concentrated or otherwise processed as desired. The glucosone solution is substantially free of contaminants other than some unreacted glucose, or glucose dimer or trimer, and whatever contaminants that may have been introduced in the original glucose charge.
Vsually, the glucose charge will be a hydrolysate of a natural product containing glucose units, most commonly starch, which will contain soluble contaminants such as other carbohydrates, e.g. maltose, formed in the starch hydrolysis.
Accordingly, the reduction of the reaction product of the first zone will provide a product, fructose, which will be comparatively free of contaminants that effect food grade status for the product, the contaminants being derived only from the glucose natural sources, e.g. starches such as corn 25starch.
The alkene reaction zone also is cleaner than attain-able when both reactions are conducted in the same reactor.
PREFERRED EMBODIMENTS
The membranes to be used in the present process are any of those commonly employed in aqueous systems and include a wide variety. Most commonly, the membranes will be comprised of nylon, a styrene polymer, usually polystyrene teflon, or a cellulose ester such as cellulose acetate or propionate.
In a first embodiment, the membrane is fitted into a reactor to provide two zones in a manner to preclude unintended mixing of the contents of the two zones. In a second embodiment, separate reactors can be coupled with the selected membrane providing the requisite interface in the coupling. For maximum migration of hydrogen peroxide from the first zone to the second zone, membranes of significant exposed surface area are of course preferred for which reason the first embodiment is more preferable.
The glucose-2-oxidase enzyme can be provided in the form of the enzyme solution in water, immobilized enzyme or immobilized cells or mycelium or the free cells or mycelium. Most commonly since the enzyme is intracellular, the cells or mycelium of the selected microorganism are used by merely suspending them in the reaction solution. Promoters and protectors for the enzyme can also be present. For example, as described in the aforesaid Folia Microbiol. 23, 292-298 tl978), the presence of fluoride ;~
ion promotes the enzymatic oxidation of glucose with 0. mucida.
Protectors for enzymes can also be used, e.g. Co, Mn and Mg salts.
~1 -.~' , 1 The enzymatic oxidation reaction is carried out until substantially complete as can be determined by monitoring the mixture using aliquots to test for glucose c~ntent~ or hy colorimetric determination of glucosone or by determination of 5 of hydrogen peroxide. Usually, reaction periods of about 24-48 hours are sufficent, de~ending on enzyme potency or activity.
A wide variety of micxoorganisms can be used to pro-duce the glucose-2-oxidase employed in the present process.
For example, the following organisms are described in the 10 literature for this purpose:
I Aspergillus parasiticus [siochem. J. 31, 1033 (1937)]
II Iridophycus flaccidum [Science 124, 171 (1956)]
III Oudemansiella mucida ~Folia Microbiol. 13, 334 (1968) ibid. 23, 292-298 (1978)]
IV Gluconobacter roseus ~J. Gen Appl. Microbiol. 1,152 (1955)]
V Polyporus obtusus [Biochem. Biophys. Acta 167, 501 (1968)]
VI Corticium caeruleum [Phytochemistry 1977 Vol. 16, p 1895-7]
The temperature for the enzymatic oxidation reaction 20 is not critical. The reaction can be conducted at room tempera-ture, or even somewhat higher than room temperature where the enzyme system employed is of reasonable heat stability. In particular, it is preferable to operate at 50C. ~nd above.
with heat stable enzyme systems in which range bacterial infection 25 of the reaction mixture is minimized. Alternatively, the enzy-matic reaction mixture can contain antibacterial agents to pre-clude extensive bacterial growth.
The first reaction zone of course should contain no significant amounts of a reducing agent for hydrogen peroxide 30 so that the beneficial results of the present process can be realised. Thus~ the system should be substantially free of ~ reducing agents for n202 t i e. d ~IOn reducing system.
5~
During the course of the present process, it is possible for some diffusion of material from the second reaction zone into the first zone, especially where anions, cations or low molecular weight compounds are present in the second zone, but such diffusion is not significant under the present conditions.
The procuedures employed for the conversion of alkenes to oxygenated products are those described in the hereinbefore described references.
The reduction of glucosone to fructose is accomplished by known procedures including chemical reduction as with zinc and acetic acid as well as catalytic hydrogenation, with the usual metal catalysts. Of these, the preferred metal catalyst is Raney Ni since its use is compatible with the desired food grade of fructose, i.e. no residues or contaminants are left by this catalyst.
In the usual procedure employed, the glucosone is hydrogenated at elevated pressure and temperature over the selected metal catalyst until the desired degree of hydrogenation has been achieved. Pressures can range from 100 to 700 atmoshpere and even higher while the temperature can range up to about 200C. Preferred is 100 to 150C. and a pressure of about 500 atmospheres.
The following example illustrates the invention.
36~5 Mycelium of o. mucida are grown in accordance with Example 1 of Czechoslovakian patent 175897 and the equivalent of 15 g. (dry weight) of the mycelium is susPended in 3 L.
5o~ 2.5% glucose solution o~o5rl NaF in one zone of a 10 L.
reactor fitted with a hydrogen perioxide-permeable membrane to form two zones. In the second zone, ethylene gas is hubbled through an aqueous solution of chloroperoxidase and halide ion buffered with a phosphate buffer (O.lM potassium phosphate) as described in European patent application 7176 (Examples 1-18).
The suspension in the first zone is mixed at 25C.
and aerated with oxygen. After 24 hours the mycelium is then separated from the solution in the first zone and resulting clear solution is then hydrogenated over Raney Ni at 500 atmos-15pheres hydrogen gas and 100C. The aqueous mixture is filteredclear of the catalyst, decolorized with carbon, deionized with ion-exchange (anionic and cationic) and concentrated to a fructose syrup at reduced pressure. Alternatively, the aqueous mixture is concentrated and fructose allowed to crystallize.
The fructose obtained as either syrup or crystalline product is of food grade quality.
The halohydrins oktained by the reaction in the second zone are converted to the corresponding epoxides by treatment with sodium hydroxide.
Essentially the same results are obtained when O. mucida is replaced with the following organisms:
- Polyporus obtusus Radulum casearium Lenzites Trabea Irpex flanus Polyporus versicolor Pellic~laria ~ilamentosa Armillaria mellea Schizophyleum com~une Corticium caeruleum .
.
This invention is concerned with a new and useful process for the prttl~ t;on of ~lucosone and m^re particulall for the production glucosone from which food-grade fructose 5 can be obtained.
Colr~nercial methods for the production of fructose, a commercially important sweetner, primarily involve a two-step process, the first, hydrolysis of a polysaccharide such as starch to produce glucose and the second, isomerization of the 10 so-produced glucose to form fructose. The latter step, as is well-known, produces a mixture of glucose and fructose from which it is difficult to separate the desired product, fructose. The commercial separation method involves the use of crystallization techniques which are costly and time-consuming.
15 More detailed description of the various methods of isomerizing glucose can be found in the literature, e.g. U.S. Patent 3,788,945, and 3,616,221.
Glucose can also be converted to fructose by the action of an enzyme, designated glucose-2-oxidase, to form 20 glucosone (D-arabino-2-hexosulose) which in turn can be re-duced to fructose with zinc and acetic acid ~Folia Micriobiol.
23, 292-298 (1978) and Czechoslovakian Patent No. 175897 to Volc et al.].
The reaction of glucose-2-oxidase with glucose to 25 produce glucosone also yields hydrogen peroxide in equimolar amount. The use of the so-produced hydrogen peroxide in the conversion of alkenes to corresponding halohydrins and epoxides has been proposed in European Patent Application 7176. In the published application, the in situ formation of hydrogen 30 peroxide is proposed by inclusion of glucose-2-oxidase and glucose in the reaction mixture which includes a halogenating ~ '.
.
.
, .
:
: : , . . :
6~5 enzyme and a source of inorganic halide into which the selected alkene is to be introduced. me disclosure of the European patent application further indicates that the glucosone product of the enzymatic oxidation of glucose can be converted to fructose by simple chemical hydrogenation.
However, fructose produced by the said process can be contaminated with significant amounts of by-products from both the enzymatic conversion of glucose ar.d the alkene conversion reaction. In particular, the latter reaction produces halohydrins and alkylene oxides, e.g. ethylene oxide, which are highly toxic material even at levels in the region of parts per million. mus, fructose produced by such a process will require careful and costly purification to attain food-grade purity. Further, the potential for contamination of fructose by virtue of secondary reactions during the initial processing state is quite high due to the highly reactive products, halohydrins and alkyleneoxides, and substantial purification procedures are required to assure the high level purity required for food-grade fructose.
SUWMARY QF THE INVENTION
This invention provides a method for the production of glucosone by enzymatic oxidation of glucose to glucosone in a reaction zone from which hydrogen peroxide is removed by use of a hydrogen peroxide-permeable m~mbrane into a second reaction zone where the hydrogen peroxide is reacted with an alkene to convert the alkene to an oxidation product.
In accordance with one embodiment of the invention, the alkene is converted to a glycol by reaction with hydrogen peroxide. mis reaction is catalyzed by os~ium, vanadium or chromium oxide or by ultraviolet light in accordance with the procedure described J.A.C.S. 58, 1302 (1936); 59, 543, 2342, 2345 (1937), .~
' .' ' ~ - .
- ,:
1 In accordance with a second embodiment of the inven-tion, the alkene is converted to a halohydrin and then to an alkylene oxide or glycol corresponding to the ~ri gi nAl ~l ken~.
reactant by reaction with hydrogen peroxide, a halogenating 5enzyme and a halide ion source, to form the halohydrin which is then converted to an epoxide or glycol, by the methods described in European patent app:Lication 7176.
The membranes employed in the present process are for the prupose of establishing two separate zones and per-lOmitting migration of hydrogen peroxide from the first to thesecond zone. The membranes therefore should be of suitable pore size to selectively permit hydrogen peroxide migration, but to preclude passage of larger molecules in the first reaction zone. Such membranes are readily available commercially and 15can be defined in terms of the molecular weight of solute particles to pass through the membrane. In the present inven-tion, membranes which permit substances of a molecular weight of less than about 100 are to be used, and preferably less than 50.
The migration or passage of hydrogen peroxide through the aforesaid membrane is accomplished through establishment of an equilibrium predicated on the relative concentrations of H202 on each side of the membrane. As the concentration of hydrogen peroxide in the first zone increases, the H202 25tends to migrate to the secon zone until equilibriu~ is rees-stablished. The reaction with an alkene in the second zone increases the rate of flow of hydrogen peroxide through the membrane by offsetting the equilibrium in the direction of the second zone, 3o .
' ' ~ ' ' -- ~ .. ..
.-1 Employing the present process results in considerable advantage particularly in the further processing of glucosone to fructose. The migration of hydr~g~n p~roxlde from the flrst reaction zone of course affects the rate of the enzymatic oxi-sdation of glucose so that the reaction tends to be more complete and the reaction times can be shorter than normally required.
Further, the first reaction zone is essentially free of con-taminants that will accumulate primarily in the second reaction zone where the so produced hydrogen peroxide is reacted. The glucosone solution produced in the first reaction zone can be used as such in the hydrogenation step or can be concentrated or otherwise processed as desired. The glucosone solution is substantially free of contaminants other than some unreacted glucose, or glucose dimer or trimer, and whatever contaminants that may have been introduced in the original glucose charge.
Vsually, the glucose charge will be a hydrolysate of a natural product containing glucose units, most commonly starch, which will contain soluble contaminants such as other carbohydrates, e.g. maltose, formed in the starch hydrolysis.
Accordingly, the reduction of the reaction product of the first zone will provide a product, fructose, which will be comparatively free of contaminants that effect food grade status for the product, the contaminants being derived only from the glucose natural sources, e.g. starches such as corn 25starch.
The alkene reaction zone also is cleaner than attain-able when both reactions are conducted in the same reactor.
PREFERRED EMBODIMENTS
The membranes to be used in the present process are any of those commonly employed in aqueous systems and include a wide variety. Most commonly, the membranes will be comprised of nylon, a styrene polymer, usually polystyrene teflon, or a cellulose ester such as cellulose acetate or propionate.
In a first embodiment, the membrane is fitted into a reactor to provide two zones in a manner to preclude unintended mixing of the contents of the two zones. In a second embodiment, separate reactors can be coupled with the selected membrane providing the requisite interface in the coupling. For maximum migration of hydrogen peroxide from the first zone to the second zone, membranes of significant exposed surface area are of course preferred for which reason the first embodiment is more preferable.
The glucose-2-oxidase enzyme can be provided in the form of the enzyme solution in water, immobilized enzyme or immobilized cells or mycelium or the free cells or mycelium. Most commonly since the enzyme is intracellular, the cells or mycelium of the selected microorganism are used by merely suspending them in the reaction solution. Promoters and protectors for the enzyme can also be present. For example, as described in the aforesaid Folia Microbiol. 23, 292-298 tl978), the presence of fluoride ;~
ion promotes the enzymatic oxidation of glucose with 0. mucida.
Protectors for enzymes can also be used, e.g. Co, Mn and Mg salts.
~1 -.~' , 1 The enzymatic oxidation reaction is carried out until substantially complete as can be determined by monitoring the mixture using aliquots to test for glucose c~ntent~ or hy colorimetric determination of glucosone or by determination of 5 of hydrogen peroxide. Usually, reaction periods of about 24-48 hours are sufficent, de~ending on enzyme potency or activity.
A wide variety of micxoorganisms can be used to pro-duce the glucose-2-oxidase employed in the present process.
For example, the following organisms are described in the 10 literature for this purpose:
I Aspergillus parasiticus [siochem. J. 31, 1033 (1937)]
II Iridophycus flaccidum [Science 124, 171 (1956)]
III Oudemansiella mucida ~Folia Microbiol. 13, 334 (1968) ibid. 23, 292-298 (1978)]
IV Gluconobacter roseus ~J. Gen Appl. Microbiol. 1,152 (1955)]
V Polyporus obtusus [Biochem. Biophys. Acta 167, 501 (1968)]
VI Corticium caeruleum [Phytochemistry 1977 Vol. 16, p 1895-7]
The temperature for the enzymatic oxidation reaction 20 is not critical. The reaction can be conducted at room tempera-ture, or even somewhat higher than room temperature where the enzyme system employed is of reasonable heat stability. In particular, it is preferable to operate at 50C. ~nd above.
with heat stable enzyme systems in which range bacterial infection 25 of the reaction mixture is minimized. Alternatively, the enzy-matic reaction mixture can contain antibacterial agents to pre-clude extensive bacterial growth.
The first reaction zone of course should contain no significant amounts of a reducing agent for hydrogen peroxide 30 so that the beneficial results of the present process can be realised. Thus~ the system should be substantially free of ~ reducing agents for n202 t i e. d ~IOn reducing system.
5~
During the course of the present process, it is possible for some diffusion of material from the second reaction zone into the first zone, especially where anions, cations or low molecular weight compounds are present in the second zone, but such diffusion is not significant under the present conditions.
The procuedures employed for the conversion of alkenes to oxygenated products are those described in the hereinbefore described references.
The reduction of glucosone to fructose is accomplished by known procedures including chemical reduction as with zinc and acetic acid as well as catalytic hydrogenation, with the usual metal catalysts. Of these, the preferred metal catalyst is Raney Ni since its use is compatible with the desired food grade of fructose, i.e. no residues or contaminants are left by this catalyst.
In the usual procedure employed, the glucosone is hydrogenated at elevated pressure and temperature over the selected metal catalyst until the desired degree of hydrogenation has been achieved. Pressures can range from 100 to 700 atmoshpere and even higher while the temperature can range up to about 200C. Preferred is 100 to 150C. and a pressure of about 500 atmospheres.
The following example illustrates the invention.
36~5 Mycelium of o. mucida are grown in accordance with Example 1 of Czechoslovakian patent 175897 and the equivalent of 15 g. (dry weight) of the mycelium is susPended in 3 L.
5o~ 2.5% glucose solution o~o5rl NaF in one zone of a 10 L.
reactor fitted with a hydrogen perioxide-permeable membrane to form two zones. In the second zone, ethylene gas is hubbled through an aqueous solution of chloroperoxidase and halide ion buffered with a phosphate buffer (O.lM potassium phosphate) as described in European patent application 7176 (Examples 1-18).
The suspension in the first zone is mixed at 25C.
and aerated with oxygen. After 24 hours the mycelium is then separated from the solution in the first zone and resulting clear solution is then hydrogenated over Raney Ni at 500 atmos-15pheres hydrogen gas and 100C. The aqueous mixture is filteredclear of the catalyst, decolorized with carbon, deionized with ion-exchange (anionic and cationic) and concentrated to a fructose syrup at reduced pressure. Alternatively, the aqueous mixture is concentrated and fructose allowed to crystallize.
The fructose obtained as either syrup or crystalline product is of food grade quality.
The halohydrins oktained by the reaction in the second zone are converted to the corresponding epoxides by treatment with sodium hydroxide.
Essentially the same results are obtained when O. mucida is replaced with the following organisms:
- Polyporus obtusus Radulum casearium Lenzites Trabea Irpex flanus Polyporus versicolor Pellic~laria ~ilamentosa Armillaria mellea Schizophyleum com~une Corticium caeruleum .
.
Claims (8)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method of producing glucosone which comprises enzymatically oxidizing glucose with glucose-2-oxidase in a first zone and separating the concomitantly produced hydrogen peroxide from said first zone through a semi-permeable membrane into a second zone wherein an alkene is reacted with said hydrogen peroxide to form oxygenated products of said alkene, said membrane being permeable only to compounds of a molecular weight of less than about 100.
2. The method according to Claim 1 wherein the product of said reaction of an alkene with hydrogen peroxide is a glycol.
3. The method according to Claim 1 wherein the product of said reaction of an alkene with hydrogen peroxide is the corresponding alkylene oxide.
4. The method according to Claim 1 where said membrane is permeable only to compounds of a molecular weight of less than about 50.
5. A method of producing fructose which comprises the steps of a) producing glucosone which comprises enzymatically oxidizing glucose with glucose-2-oxidase in a first zone and separating the concomitantly produced hydrogen peroxide from said first zone through a semi-permeable membrane into a second zone wherein an alkene is reacted with said hydrogen peroxide to form oxygenated products of said alkene, said membrane being permeable only to compounds of a molecular weight of less than about 100, and b) reducing the so-produced glucosone to obtain fructose.
6. The method according to Claim 5 wherein the reduction is effected by catalytic hydrogenation.
7. The method according to Claim 6 wherein the catalyst is Raney Ni.
8. The method according to Claim 5 wherein the filtered reaction mixture obtained in Step a is employed in Step b.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000382228A CA1150655A (en) | 1981-07-22 | 1981-07-22 | Process for making glucosone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000382228A CA1150655A (en) | 1981-07-22 | 1981-07-22 | Process for making glucosone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1150655A true CA1150655A (en) | 1983-07-26 |
Family
ID=4120496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000382228A Expired CA1150655A (en) | 1981-07-22 | 1981-07-22 | Process for making glucosone |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1150655A (en) |
-
1981
- 1981-07-22 CA CA000382228A patent/CA1150655A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0054066B1 (en) | Process for making glucosone | |
| US4440855A (en) | Process for preparing L-glucosone | |
| Huwig et al. | Laboratory procedures for producing 2-keto-D-glucose, 2-keto-D-xylose and 5-keto-D-fructose from D-glucose, D-xylose and L-sorbose with immobilized pyranose oxidase of Peniophora gigantea | |
| EP0056038B1 (en) | Carbohydrate process | |
| CA1195276A (en) | Process for production of glucosone | |
| Nishizawa et al. | A forcedâflow membrane reactor for transfructosylation using ceramic membrane | |
| US4908311A (en) | Process for enzymatic preparation of cellooligosaccharides | |
| GB2381524A (en) | Synthesis of xylitol from ribulose | |
| GB2179946A (en) | Process for producing sugar mixture having high fructo-oligosaccharide content | |
| EP0054067B1 (en) | Process for making fructose | |
| FI79557B (en) | FOERFARANDE FOER ISOMERISERING AV GLUKOS TILL FRUKTOS. | |
| US6500649B2 (en) | Process for the conversion of organic materials, particularly saccharide materials, comprising an enzymatic oxidation step in the presence of ruthenium or palladium | |
| CA1150655A (en) | Process for making glucosone | |
| CA1083988A (en) | High mannitol process (enzymatic isomerization) | |
| CA1150656A (en) | Carbohydrate process | |
| EP0200095B1 (en) | Immobilized maltooligosaccharide-forming amylase and process for the production of maltooligosaccharide using said enzyme | |
| KR0131134B1 (en) | Preparation process of isomalto oligo saccharide in hign yield and high purity | |
| CA1169376A (en) | Process for making fructose | |
| JP3916682B2 (en) | Method for producing glycoside | |
| US4582803A (en) | Staged immobilized amyloglucosidase and immobilized glucose isomerase in producing fructose from thinned starch | |
| JP2798920B2 (en) | Process for producing syrup containing isomaltooligosaccharide | |
| JPS5937959B2 (en) | How to improve glucose concentration | |
| KR0130938B1 (en) | Preparation process of high concentrated galacto-oligo-saccharide | |
| KR950009832B1 (en) | New microorganim zymomonas mobilis cp4 and producing method of d-glucitol and d-gluconic acid | |
| HU182758B (en) | Process for preparing glucosone and if desired fructose therefrom |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20000726 |