US3875140A - Process for the preparation of fructose - Google Patents
Process for the preparation of fructose Download PDFInfo
- 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
- Authority
- 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
Links
- 229930091371 Fructose Natural products 0.000 title claims abstract description 37
- 239000005715 Fructose Substances 0.000 title claims abstract description 37
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title description 2
- 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 31
- -1 aryl boric acid Chemical compound 0.000 claims abstract description 26
- 239000004327 boric acid Substances 0.000 claims abstract description 23
- 239000008103 glucose Substances 0.000 claims abstract description 23
- 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 claims abstract description 13
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 11
- 239000000243 solution Substances 0.000 claims description 36
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 9
- 235000000346 sugar Nutrition 0.000 claims description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
- BBJIQHIAPXAMSJ-UHFFFAOYSA-N (2-ethenylphenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC=C1C=C BBJIQHIAPXAMSJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920000620 organic polymer Polymers 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical class OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 claims description 2
- GZCGUPFRVQAUEE-KVTDHHQDSA-N aldehydo-D-mannose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-KVTDHHQDSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 abstract description 9
- 239000003513 alkali Substances 0.000 abstract description 3
- 235000010338 boric acid Nutrition 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 18
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012670 alkaline solution Substances 0.000 description 5
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000010414 supernatant solution Substances 0.000 description 3
- SXLHAMYMTUEALX-UHFFFAOYSA-N (4-methoxyphenoxy)boronic acid Chemical compound COC1=CC=C(OB(O)O)C=C1 SXLHAMYMTUEALX-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- UHGZXUCJYHCRQS-UHFFFAOYSA-N (2-nitrophenoxy)boronic acid Chemical class OB(O)OC1=CC=CC=C1[N+]([O-])=O UHGZXUCJYHCRQS-UHFFFAOYSA-N 0.000 description 1
- DQVXWCCLFKMJTQ-UHFFFAOYSA-N (4-methylphenoxy)boronic acid Chemical compound CC1=CC=C(OB(O)O)C=C1 DQVXWCCLFKMJTQ-UHFFFAOYSA-N 0.000 description 1
- HEFOGCNQSDTNKM-UHFFFAOYSA-N (6-sulfonylcyclohexa-2,4-dien-1-yl)oxyboronic acid Chemical compound S(=O)(=O)=C1C(C=CC=C1)OB(O)O HEFOGCNQSDTNKM-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- SYTWAQPMXUCWRY-WNJXEPBRSA-N CO[C@@]([C@@H]([C@H](C=O)O)O)(O)[C@H](O)CO Chemical compound CO[C@@]([C@@H]([C@H](C=O)O)O)(O)[C@H](O)CO SYTWAQPMXUCWRY-WNJXEPBRSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000005619 boric acid group Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940116441 divinylbenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- LZTBZQSQFMLGQH-UHFFFAOYSA-N naphthalen-1-yloxyboronic acid Chemical compound C1=CC=C2C(OB(O)O)=CC=CC2=C1 LZTBZQSQFMLGQH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02J—CIRCUIT ARRANGEMENTS OR SYSTEMS FOR SUPPLYING OR DISTRIBUTING ELECTRIC POWER; SYSTEMS FOR STORING ELECTRIC ENERGY
- H02J13/00—Circuit 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
- H02J13/00004—Circuit 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.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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 (show.php) |
| AT (1) | AT329472B (show.php) |
| DE (1) | DE2229064A1 (show.php) |
| FR (1) | FR2189512B1 (show.php) |
| GB (1) | GB1369185A (show.php) |
Cited By (13)
| 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)
| 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 |
-
1972
- 1972-06-15 DE DE2229064A patent/DE2229064A1/de active Pending
-
1973
- 1973-05-30 US US365356A patent/US3875140A/en not_active Expired - Lifetime
- 1973-06-11 GB GB2769473A patent/GB1369185A/en not_active Expired
- 1973-06-13 FR FR7321456A patent/FR2189512B1/fr not_active Expired
- 1973-06-14 AT AT523873A patent/AT329472B/de not_active IP Right Cessation
Patent Citations (7)
| 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 (14)
| 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 |
| 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 |
|---|---|
| FR2189512A1 (show.php) | 1974-01-25 |
| AT329472B (de) | 1976-05-10 |
| DE2229064A1 (de) | 1973-12-20 |
| ATA523873A (de) | 1975-07-15 |
| GB1369185A (en) | 1974-10-02 |
| FR2189512B1 (show.php) | 1977-02-11 |
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