DE2622316A1 - Verfahren zur herstellung einer glucose und mannose enthaltenden loesung - Google Patents
Verfahren zur herstellung einer glucose und mannose enthaltenden loesungInfo
- Publication number
- DE2622316A1 DE2622316A1 DE19762622316 DE2622316A DE2622316A1 DE 2622316 A1 DE2622316 A1 DE 2622316A1 DE 19762622316 DE19762622316 DE 19762622316 DE 2622316 A DE2622316 A DE 2622316A DE 2622316 A1 DE2622316 A1 DE 2622316A1
- Authority
- DE
- Germany
- Prior art keywords
- glucose
- mannose
- catalyst
- weight
- 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.)
- Withdrawn
Links
- 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 title claims description 92
- 239000008103 glucose Substances 0.000 title claims description 88
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title description 3
- 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 title 1
- 239000003054 catalyst Substances 0.000 claims description 60
- 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 claims description 55
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 25
- 229910052750 molybdenum Inorganic materials 0.000 claims description 24
- 239000011733 molybdenum Substances 0.000 claims description 24
- 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 description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 description 44
- 238000006345 epimerization reaction Methods 0.000 description 33
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 30
- 229930195725 Mannitol Natural products 0.000 description 30
- 239000000594 mannitol Substances 0.000 description 30
- 229960001855 mannitol Drugs 0.000 description 30
- 235000010355 mannitol Nutrition 0.000 description 30
- 238000005984 hydrogenation reaction Methods 0.000 description 27
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 15
- 239000000600 sorbitol Substances 0.000 description 15
- 229920002261 Corn starch Polymers 0.000 description 14
- 239000008120 corn starch Substances 0.000 description 14
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 235000000346 sugar Nutrition 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 10
- 150000001720 carbohydrates Chemical class 0.000 description 10
- 235000014633 carbohydrates Nutrition 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 9
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000003957 anion exchange resin Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 229910052707 ruthenium Inorganic materials 0.000 description 8
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 4
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- 229960004903 invert sugar Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SRBFZHDQGSBBOR-SOOFDHNKSA-N D-ribopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-SOOFDHNKSA-N 0.000 description 3
- 229930091371 Fructose Natural products 0.000 description 3
- 239000005715 Fructose Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052901 montmorillonite Inorganic materials 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LKDRXBCSQODPBY-IANNHFEVSA-N D-sorbose Chemical compound OCC1(O)OC[C@@H](O)[C@H](O)[C@H]1O LKDRXBCSQODPBY-IANNHFEVSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WQZGKKKJIJFFOK-JFNONXLTSA-N L-mannopyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-JFNONXLTSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- -1 molybdate ions Chemical class 0.000 description 2
- 238000011027 product recovery Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011684 sodium molybdate Substances 0.000 description 2
- 235000015393 sodium molybdate Nutrition 0.000 description 2
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- 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
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WQZGKKKJIJFFOK-CBPJZXOFSA-N D-Gulose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-CBPJZXOFSA-N 0.000 description 1
- BJHIKXHVCXFQLS-PUFIMZNGSA-N D-psicose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C(=O)CO BJHIKXHVCXFQLS-PUFIMZNGSA-N 0.000 description 1
- LKDRXBCSQODPBY-OEXCPVAWSA-N D-tagatose Chemical compound OCC1(O)OC[C@@H](O)[C@H](O)[C@@H]1O LKDRXBCSQODPBY-OEXCPVAWSA-N 0.000 description 1
- WQZGKKKJIJFFOK-ZZWDRFIYSA-N L-glucose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-ZZWDRFIYSA-N 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
- 241001465754 Metazoa Species 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- GZCGUPFRVQAUEE-KAZBKCHUSA-N aldehydo-D-talose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-KAZBKCHUSA-N 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000013736 caramel Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 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
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/26—Hexahydroxylic alcohols
-
- 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
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/578,548 US4029878A (en) | 1975-05-19 | 1975-05-19 | Process for preparing mannitol from glucose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2622316A1 true DE2622316A1 (de) | 1976-12-02 |
Family
ID=24313343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762622316 Withdrawn DE2622316A1 (de) | 1975-05-19 | 1976-05-19 | Verfahren zur herstellung einer glucose und mannose enthaltenden loesung |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4029878A (enExample) |
| JP (1) | JPS51141807A (enExample) |
| BE (1) | BE842004A (enExample) |
| BR (1) | BR7602485A (enExample) |
| CA (1) | CA1071194A (enExample) |
| DE (1) | DE2622316A1 (enExample) |
| FI (1) | FI761413A7 (enExample) |
| FR (1) | FR2311846A1 (enExample) |
| GB (1) | GB1506534A (enExample) |
| IT (1) | IT1121717B (enExample) |
| LU (1) | LU74981A1 (enExample) |
| MX (1) | MX3400E (enExample) |
| NL (1) | NL7605329A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0288847A2 (de) | 1987-04-30 | 1988-11-02 | BASF Aktiengesellschaft | Kontinuierliches Verfahren zur Epimerisierung von Zuckern, insbesondere von D-Arabinose zu D-Ribose |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292451A (en) * | 1978-03-30 | 1981-09-29 | Ici Americas Inc. | High mannitol process (alkaline hydrogenation in presence of alkali metal carbonate) |
| US4421568A (en) * | 1981-08-26 | 1983-12-20 | Hydrocarbon Research, Inc. | Process for making L-sugars and D-fructose |
| US4471114A (en) * | 1982-12-30 | 1984-09-11 | Union Carbide Corporation | Separation of mannose by selective adsorption on zeolitic molecular sieves |
| USRE33105E (en) * | 1982-12-30 | 1989-10-31 | Uop | Separation of mannose by selective adsorption on zeolitic molecular sieves |
| DE3622643A1 (de) * | 1986-07-05 | 1988-01-14 | Basf Ag | Verbessertes verfahren zur epimerisierung von zuckern, insbesondere von d-arabinose zu d-ribose |
| US4718405A (en) * | 1986-07-25 | 1988-01-12 | Uop Inc. | Enhancing L-glucose yield: epimerization of L-mannose by molybdate in presence of epimerization inhibitors |
| US4815445A (en) * | 1988-02-09 | 1989-03-28 | Allied-Signal Inc. | Solid catalysts for epimerization of aldoses; continuous interconversion of epimeric sugars |
| JP2784230B2 (ja) * | 1988-02-09 | 1998-08-06 | ユーオーピー・インコーポレーテッド | エピマーアルドースおよびアルドース同族体の連続相互変換に用いる固体触媒 |
| DE3818198A1 (de) * | 1988-05-28 | 1989-12-21 | Basf Ag | Verfahren zur herstellung niederer mehrwertiger alkohole |
| US5162517A (en) * | 1989-10-14 | 1992-11-10 | Bayer Aktiengesellschaft | Process for the preparation of epimer-free sugar alcohols from the group consisting of xylitol, sorbitol (D-glucitol), 4-O-β-D-galactopyranosyl-D-glucitol and 4-O-α-D-glucopyranosyl-D-sorbitol |
| US5334253A (en) * | 1990-11-13 | 1994-08-02 | Lloyd Berg | Solution of certain five and six carbon atom carbohydrates |
| FR2694019B1 (fr) * | 1992-07-22 | 1994-10-14 | Roquette Freres | Procédé de fabrication de mannitol. |
| US5433793A (en) * | 1993-07-30 | 1995-07-18 | Uop | Preparation of high purity D-allose from D-glucose |
| GB9421894D0 (en) * | 1994-10-31 | 1994-12-14 | Cerestar Holding Bv | Catalyst regeneration |
| US6140498A (en) * | 1998-11-17 | 2000-10-31 | Xyrofin Oy | Process for the continuous production of high purity L-ribose |
| AU3228100A (en) * | 1999-02-10 | 2000-08-29 | Eastman Chemical Company | Corn fiber for the production of advanced chemicals and materials |
| TWI383809B (zh) * | 2005-06-29 | 2013-02-01 | Otsuka Pharma Co Ltd | 含有西洛他唑（ｃｉｌｏｓｔａｚｏｌ）之口腔崩解粉末 |
| FR2949296B1 (fr) * | 2009-09-01 | 2011-11-18 | Roquette Freres | Procede de remplacement total ou partiel du talc dans les chewing-gums |
| BR112012020404B1 (pt) * | 2010-02-15 | 2018-10-02 | Cargill Inc | processo para epimerização de sacarídeos, uso de um microdispositivo e uso de mano-oligossacarídeos |
| BE1021455B1 (nl) * | 2012-11-22 | 2015-11-26 | Syral Belgium Nv | Werkwijze voor het verwerken van substraten die een uitgangsstof voor mannitol omvatten. |
| CN104045670B (zh) * | 2013-03-15 | 2017-06-06 | 大连中科格莱克生物科技有限公司 | 一种甘露糖的制备方法 |
| CN114522705B (zh) * | 2022-02-18 | 2023-12-12 | 常州大学 | 用于糖差向异构化反应的水相稳定的高效负载型固体酸催化剂及其应用 |
| CN115746063A (zh) * | 2022-11-29 | 2023-03-07 | 中国农业科学院饲料研究所 | 一种饲用d-甘露糖及其制备方法与应用 |
| CN115784838A (zh) * | 2022-12-07 | 2023-03-14 | 浙江华康药业股份有限公司 | 一种利用晶体葡萄糖联产甘露醇晶体和山梨醇晶体的方法 |
| CN119350358B (zh) * | 2024-12-27 | 2025-03-18 | 山东百龙创园生物科技股份有限公司 | 一种联产异山梨醇和甘露醇的方法及获得的产品和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1990245A (en) * | 1926-11-18 | 1935-02-05 | Ig Farbenindustrie Ag | Production of polyhydric alcohols |
| US2280975A (en) * | 1938-08-17 | 1942-04-28 | Atlas Powder Co | Hydrogenation of invertible saccharides |
| US2642462A (en) * | 1948-06-14 | 1953-06-16 | Atlas Powder Co | Process for continuous hydrogenation of sugars |
| US2759023A (en) * | 1952-11-03 | 1956-08-14 | Scholten Chemische Fab | Process of manufacturing polyhydric alcohols by catalytic reduction of carbohydrates |
| JPS5195006A (en) * | 1975-02-13 | 1976-08-20 | Mannitsuto oyobi sorubitsutokongobutsuno seizoho |
-
1975
- 1975-05-19 US US05/578,548 patent/US4029878A/en not_active Expired - Lifetime
-
1976
- 1976-03-29 MX MX000125U patent/MX3400E/es unknown
- 1976-04-07 CA CA249,721A patent/CA1071194A/en not_active Expired
- 1976-04-23 BR BR2485/76A patent/BR7602485A/pt unknown
- 1976-05-12 JP JP51053380A patent/JPS51141807A/ja active Granted
- 1976-05-17 GB GB20197/76A patent/GB1506534A/en not_active Expired
- 1976-05-18 FR FR7614973A patent/FR2311846A1/fr active Granted
- 1976-05-19 FI FI761413A patent/FI761413A7/fi not_active Application Discontinuation
- 1976-05-19 DE DE19762622316 patent/DE2622316A1/de not_active Withdrawn
- 1976-05-19 NL NL7605329A patent/NL7605329A/xx not_active Application Discontinuation
- 1976-05-19 LU LU74981A patent/LU74981A1/xx unknown
- 1976-05-19 BE BE167172A patent/BE842004A/xx unknown
- 1976-05-19 IT IT23408/76A patent/IT1121717B/it active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0288847A2 (de) | 1987-04-30 | 1988-11-02 | BASF Aktiengesellschaft | Kontinuierliches Verfahren zur Epimerisierung von Zuckern, insbesondere von D-Arabinose zu D-Ribose |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7605329A (nl) | 1976-11-23 |
| CA1071194A (en) | 1980-02-05 |
| FI761413A7 (enExample) | 1976-11-20 |
| US4029878A (en) | 1977-06-14 |
| BR7602485A (pt) | 1977-01-25 |
| IT1121717B (it) | 1986-04-23 |
| MX3400E (es) | 1980-10-30 |
| AU1244476A (en) | 1977-10-06 |
| BE842004A (fr) | 1976-11-19 |
| JPS5640700B2 (enExample) | 1981-09-22 |
| FR2311846A1 (fr) | 1976-12-17 |
| GB1506534A (en) | 1978-04-05 |
| LU74981A1 (enExample) | 1977-01-19 |
| FR2311846B1 (enExample) | 1980-02-15 |
| JPS51141807A (en) | 1976-12-07 |
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