DE2350668C2 - Verfahren zur Gewinnung von kristallinem, nicht mehr als etwa 0,1 Gew.% Xylose enthaltendem Xylit - Google Patents
Verfahren zur Gewinnung von kristallinem, nicht mehr als etwa 0,1 Gew.% Xylose enthaltendem XylitInfo
- Publication number
- DE2350668C2 DE2350668C2 DE2350668A DE2350668A DE2350668C2 DE 2350668 C2 DE2350668 C2 DE 2350668C2 DE 2350668 A DE2350668 A DE 2350668A DE 2350668 A DE2350668 A DE 2350668A DE 2350668 C2 DE2350668 C2 DE 2350668C2
- Authority
- DE
- Germany
- Prior art keywords
- xylose
- xylitol
- weight
- water
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 title claims description 89
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 title claims description 46
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 title claims description 46
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 title claims description 44
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 title claims description 44
- 239000000811 xylitol Substances 0.000 title claims description 44
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 title claims description 44
- 229960002675 xylitol Drugs 0.000 title claims description 44
- 235000010447 xylitol Nutrition 0.000 title claims description 44
- 238000000034 method Methods 0.000 title claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 238000001640 fractional crystallisation Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002488 Hemicellulose Polymers 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 241000609240 Ambelania acida Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 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 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000565362 Fraxinus velutina Species 0.000 description 1
- 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 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003741 xylose derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US29640472A | 1972-10-10 | 1972-10-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2350668A1 DE2350668A1 (de) | 1974-04-25 |
DE2350668C2 true DE2350668C2 (de) | 1983-02-17 |
Family
ID=23141871
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2350668A Expired DE2350668C2 (de) | 1972-10-10 | 1973-10-09 | Verfahren zur Gewinnung von kristallinem, nicht mehr als etwa 0,1 Gew.% Xylose enthaltendem Xylit |
Country Status (17)
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4066711A (en) * | 1976-03-15 | 1978-01-03 | Suomen Sokeri Osakeyhtio (Finnish Sugar Company) | Method for recovering xylitol |
EP1075795B1 (en) * | 1999-08-10 | 2003-04-09 | Ajinomoto Co., Inc. | Process for producing xylitol of high purity |
EP4330492A1 (en) | 2021-04-26 | 2024-03-06 | Illinois Tool Works, Inc. | Template |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2917390A (en) * | 1959-12-15 | apel etal | ||
DE1813834A1 (de) * | 1968-12-11 | 1970-07-09 | Schoenemann Dr Karl | Verfahren zur Gewinnung von Xylit |
-
1973
- 1973-10-02 ZA ZA737731A patent/ZA737731B/xx unknown
- 1973-10-03 GB GB4611373A patent/GB1413032A/en not_active Expired
- 1973-10-04 AU AU61001/73A patent/AU477100B2/en not_active Expired
- 1973-10-08 NL NLAANVRAGE7313799,A patent/NL185775B/xx not_active IP Right Cessation
- 1973-10-09 CH CH1435873A patent/CH581593A5/xx not_active IP Right Cessation
- 1973-10-09 IT IT53020/73A patent/IT997758B/it active
- 1973-10-09 DE DE2350668A patent/DE2350668C2/de not_active Expired
- 1973-10-09 SE SE7313716A patent/SE405723B/xx unknown
- 1973-10-09 DK DK547673A patent/DK152723C/da not_active IP Right Cessation
- 1973-10-09 FI FI3124/73A patent/FI59241C/fi active
- 1973-10-09 NO NO3920/73A patent/NO140666C/no unknown
- 1973-10-09 JP JP48113739A patent/JPS5088008A/ja active Pending
- 1973-10-09 FR FR7335964A patent/FR2202069B1/fr not_active Expired
- 1973-10-09 BE BE136477A patent/BE805830A/xx not_active IP Right Cessation
- 1973-10-09 BR BR7853/73A patent/BR7307853D0/pt unknown
- 1973-10-09 CA CA182,827A patent/CA996139A/en not_active Expired
- 1973-10-10 IE IE01810/73A patent/IE38959B1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
BE805830A (fr) | 1974-04-09 |
DK152723C (da) | 1988-09-26 |
AU6100173A (en) | 1975-04-10 |
JPS5088008A (US07655688-20100202-C00086.png) | 1975-07-15 |
CH581593A5 (US07655688-20100202-C00086.png) | 1976-11-15 |
DE2350668A1 (de) | 1974-04-25 |
IE38959L (en) | 1974-04-10 |
ZA737731B (en) | 1974-09-25 |
NO140666B (no) | 1979-07-09 |
NL185775B (nl) | 1990-02-16 |
FI59241C (fi) | 1981-07-10 |
DK152723B (da) | 1988-05-02 |
IE38959B1 (en) | 1978-07-05 |
CA996139A (en) | 1976-08-31 |
FR2202069A1 (US07655688-20100202-C00086.png) | 1974-05-03 |
SE405723B (sv) | 1978-12-27 |
BR7307853D0 (pt) | 1974-07-18 |
IT997758B (it) | 1975-12-30 |
GB1413032A (en) | 1975-11-05 |
FI59241B (fi) | 1981-03-31 |
NL7313799A (US07655688-20100202-C00086.png) | 1974-04-16 |
FR2202069B1 (US07655688-20100202-C00086.png) | 1978-09-29 |
AU477100B2 (en) | 1976-10-14 |
NO140666C (no) | 1979-10-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
OD | Request for examination | ||
D2 | Grant after examination | ||
8363 | Opposition against the patent | ||
8331 | Complete revocation |