CA1150655A - Methode de production de glucosone - Google Patents

Methode de production de glucosone

Info

Publication number: CA1150655A
Authority: CA; Canada
Prior art keywords: zone; hydrogen peroxide; glucose; alkene; glucosone
Prior art date: 1981-07-22
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

CA000382228A

Other languages

English (en)

Inventor

John A. Maselli

Robert O. Horwath

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.)

Standard Brands Inc

Original Assignee

Standard Brands Inc

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.)

1981-07-22

Filing date

1981-07-22

Publication date

1983-07-26

1981-07-22 Application filed by Standard Brands Inc filed Critical Standard Brands Inc

1981-07-22 Priority to CA000382228A priority Critical patent/CA1150655A/fr

1983-07-26 Application granted granted Critical

1983-07-26 Publication of CA1150655A publication Critical patent/CA1150655A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 30
DCNMIDLYWOTSGK-HSUXUTPPSA-N D-glucosone Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C=O DCNMIDLYWOTSGK-HSUXUTPPSA-N 0.000 title claims abstract description 20
230000008569 process Effects 0.000 title abstract description 13
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 46
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 21
239000008103 glucose Substances 0.000 claims abstract description 21
239000012528 membrane Substances 0.000 claims abstract description 21
150000001336 alkenes Chemical class 0.000 claims abstract description 18
108010001816 pyranose oxidase Proteins 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract 4
230000001590 oxidative effect Effects 0.000 claims abstract 3
238000006243 chemical reaction Methods 0.000 claims description 27
229930091371 Fructose Natural products 0.000 claims description 20
239000005715 Fructose Substances 0.000 claims description 20
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 20
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 6
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
108090000790 Enzymes Proteins 0.000 description 9
102000004190 Enzymes Human genes 0.000 description 9
239000000047 product Substances 0.000 description 8
239000000356 contaminant Substances 0.000 description 7
230000002255 enzymatic effect Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
150000003944 halohydrins Chemical class 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
230000005012 migration Effects 0.000 description 5
238000013508 migration Methods 0.000 description 5
229920002472 Starch Polymers 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
241000993286 Mucidula mucida Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
235000013305 food Nutrition 0.000 description 3
-1 halide ion Chemical class 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
239000008107 starch Substances 0.000 description 3
241001529717 Corticium <basidiomycota> Species 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241000222640 Polyporus Species 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
230000001012 protector Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
244000221226 Armillaria mellea Species 0.000 description 1
235000011569 Armillaria mellea Nutrition 0.000 description 1
241000228230 Aspergillus parasiticus Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
108010035722 Chloride peroxidase Proteins 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
241001492300 Gloeophyllum trabeum Species 0.000 description 1
241001631175 Gluconobacter roseus Species 0.000 description 1
108010093096 Immobilized Enzymes Proteins 0.000 description 1
241000222342 Irpex Species 0.000 description 1
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
241001147496 Mazzaella flaccida Species 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241001452227 Radulodon casearius Species 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
241000222355 Trametes versicolor Species 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000009471 action Effects 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229920006218 cellulose propionate Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
238000011109 contamination Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
235000021433 fructose syrup Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002303 glucose derivatives Chemical class 0.000 description 1
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
239000000413 hydrolysate Substances 0.000 description 1
210000001822 immobilized cell Anatomy 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000013638 trimer Substances 0.000 description 1
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
229910001935 vanadium oxide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

CA000382228A 1981-07-22 1981-07-22 Methode de production de glucosone Expired CA1150655A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000382228A CA1150655A (fr)	1981-07-22	1981-07-22	Methode de production de glucosone

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000382228A CA1150655A (fr)	1981-07-22	1981-07-22	Methode de production de glucosone

Publications (1)

Publication Number	Publication Date
CA1150655A true CA1150655A (fr)	1983-07-26

Family

ID=4120496

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000382228A Expired CA1150655A (fr)	1981-07-22	1981-07-22	Methode de production de glucosone

Country Status (1)

Country	Link
CA (1)	CA1150655A (fr)

1981
- 1981-07-22 CA CA000382228A patent/CA1150655A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-07-26	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20000726

Publication	Publication Date	Title
EP0054066B1 (fr)	1984-10-24	Procede de fabrication de glucozone
US4440855A (en)	1984-04-03	Process for preparing L-glucosone
Huwig et al.	1994	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 (fr)	1984-09-26	Procede a hydrate de carbone
Nishizawa et al.	2000	A forced‐flow membrane reactor for transfructosylation using ceramic membrane
CA1195276A (fr)	1985-10-15	Procede de preparation du glucosone
US4908311A (en)	1990-03-13	Process for enzymatic preparation of cellooligosaccharides
EP0054067B1 (fr)	1985-09-18	Proced de fabrication de fructose
FI79557B (fi)	1989-09-29	Foerfarande foer isomerisering av glukos till fruktos.
US6500649B2 (en)	2002-12-31	Process for the conversion of organic materials, particularly saccharide materials, comprising an enzymatic oxidation step in the presence of ruthenium or palladium
CA1150655A (fr)	1983-07-26	Methode de production de glucosone
CA1083988A (fr)	1980-08-19	Procede (d'isomerisation enzymatique) produisant beaucoup de mannitol
CA1150656A (fr)	1983-07-26	Methode de production de carbohydrates
EP0200095B1 (fr)	1990-08-29	Amylase immobilisée formant un malto-oligosaccharide et procédé de production de malto-oligosaccharides en utilisant ledit enzyme
KR0131134B1 (ko)	1998-04-11	고수율, 고순도 이소말토 올리고당의 제조방법
CA1169376A (fr)	1984-06-19	Procede de fabrication du fructose
JP3916682B2 (ja)	2007-05-16	配糖体の製造方法
KR950009832B1 (ko)	1995-08-29	지모모나스 모빌리스 sg11을 이용한 글루코산 및 글루시톨의 제조방법
US4582803A (en)	1986-04-15	Staged immobilized amyloglucosidase and immobilized glucose isomerase in producing fructose from thinned starch
KR0130938B1 (ko)	1998-04-11	고농도 갈락토올리고당의 제조방법
JP2798920B2 (ja)	1998-09-17	イソマルトオリゴ糖含有シラップの製造方法
JPS5937959B2 (ja)	1984-09-12	ブドウ糖濃度向上法
KR950012619B1 (ko)	1995-10-19	새로운 복합감미료의 제조방법
HU182758B (en)	1984-03-28	Process for preparing glucosone and if desired fructose therefrom
CS233867B1 (cs)	1985-03-14	Způsob oxidace D-glukosy na D-glukonovou kyselinu