CS211585B1 - Method of chromatographic separation of alditoles - Google Patents
Method of chromatographic separation of alditoles Download PDFInfo
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- CS211585B1 CS211585B1 CS805579A CS805579A CS211585B1 CS 211585 B1 CS211585 B1 CS 211585B1 CS 805579 A CS805579 A CS 805579A CS 805579 A CS805579 A CS 805579A CS 211585 B1 CS211585 B1 CS 211585B1
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- CS
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- Prior art keywords
- alditols
- chromatographic separation
- mixture
- cycle
- alditoles
- Prior art date
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- 229920001223 polyethylene glycol Polymers 0.000 title claims description 19
- 238000013375 chromatographic separation Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 150000005846 sugar alcohols Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 12
- 238000010828 elution Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 3
- 239000003729 cation exchange resin Substances 0.000 claims description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 9
- 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 8
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 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 5
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 5
- 235000010355 mannitol Nutrition 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- JVWLUVNSQYXYBE-UHFFFAOYSA-N Ribitol Natural products OCC(C)C(O)C(O)CO JVWLUVNSQYXYBE-UHFFFAOYSA-N 0.000 description 4
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 4
- -1 Borate ions Chemical class 0.000 description 3
- 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 3
- 229930195725 Mannitol Natural products 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 3
- 238000005341 cation exchange Methods 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 229960002920 sorbitol Drugs 0.000 description 3
- OXQKEKGBFMQTML-KVTDHHQDSA-N volemitol Chemical compound OC[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-KVTDHHQDSA-N 0.000 description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 3
- 239000000811 xylitol Substances 0.000 description 3
- 235000010447 xylitol Nutrition 0.000 description 3
- 229960002675 xylitol Drugs 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-altritol Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 description 2
- OXQKEKGBFMQTML-UHFFFAOYSA-N D-glycero-D-gluco-heptitol Natural products OCC(O)C(O)C(O)C(O)C(O)CO OXQKEKGBFMQTML-UHFFFAOYSA-N 0.000 description 2
- 239000004386 Erythritol Substances 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HEBKCHPVOIAQTA-IMJSIDKUSA-N L-arabinitol Chemical compound OC[C@H](O)C(O)[C@@H](O)CO HEBKCHPVOIAQTA-IMJSIDKUSA-N 0.000 description 2
- FBPFZTCFMRRESA-UNTFVMJOSA-N L-iditol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO FBPFZTCFMRRESA-UNTFVMJOSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 235000019414 erythritol Nutrition 0.000 description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 2
- 229940009714 erythritol Drugs 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- OXQKEKGBFMQTML-BIVRFLNRSA-N perseitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-BIVRFLNRSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- WXYXERHRDKEISL-ZXZARUISSA-N (2R,4S)-1,2,4,5-tetrahydroxypentan-3-one Chemical compound OC[C@H](O)C(=O)[C@H](O)CO WXYXERHRDKEISL-ZXZARUISSA-N 0.000 description 1
- FBPFZTCFMRRESA-FBXFSONDSA-N Allitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-FBXFSONDSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
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- Saccharide Compounds (AREA)
Description
POPIS VYNÁLEZU
K AUTORSKÉMU OSVEDČENIU ČESKOSLOVENSKÁSOCIALISTICKÁREPUBLIKA< 19 )
/22/ Přihlášené 23 11 79/21/ /PV 8055-7 9/ 211585 (11) (Bl) (51) Int. Cl.3B 01 D 15/08
ÚŘAD PRO VYNÁLEZYA OBJEVY (.40) Zverejnené 31 07 81(45) Vydané 15.03 83 (75)
Autor vynálezu PETRUS LADISLAV ing. CSc., BÍLIK VOJTECH RNDr. CSc. ,
KUNIAK ÍUDOVÍT ing. CSc., BRATISLAVA (54) Spósob chromatografického delenia alditolov
Vynález sa týká chromatografického' delenia alditolov na štipci katexu v lantanitom cykleza použitia vody ako elučného činidla.
Prakticky všetky delenia zmesí alditolov sú založené na chromatografických metódach.Boritanové ióny ako zložky chromatografického systému využívá papierova chromatografia/fe. R. Barker, D. C. C. Sraith, Chera. and Ind. 1954, 19; Stankovič, V. Bílik, M. Kedoroňko, J. Kanigsteín, Chem. Zvěsti 29, 685 chromatografia elúciou bor itanovými puframi na stlpcoch anexu v boritanovom cykle B. Foster, Adv. Varbohyd. Chem.12, 114 /1957ij a aktív- neho uhlia a celistu fS. A. Barker, E. J. Bouřné, 0. Theander, J. Chem. Soc. 1 95 5, 42767·Vzájorané rozdelenie niektorých alditolov bolo dosiahnuté na stlpcoch Fullerovej zeminy a ce-lulózy /U. W. Binkley, Adv. Carbohyd. Chem. 1 0 , 54 * * * * * * * * * * * * 67 /1955/7» na anexe v síranovom cykle /0. Sa-muelson, H. Strb*mberg, Carbohyd. Res. 3., .89 /1 966/ a na katexoch v lítnom, vápenatom a bárna- tom cykle /J. K. N. Jones, R. A. Wall, Canad. J. Chem. 38 , 2290 / 1 960/: 0 . Samuelson, H.
StrSmberg, Acta Chem. Scand . 2 2, 1 252 / 1 968/; S. J. Angyal, G. S. Bethell, R. J. Beveridge,Carnohyd. Res. 73 , 9 /1979/; A. J. Melája, L. Hamalaineh, Ger. 2 418 801 , C. A. 82., 73 397 / 1975/; A. J. Melaja,L. Hamalainen, L. Rantanen, U. S. 3 928 1 93 , C. A. 8 5 , 35 1 31 / 1 976/.Navrhovaný sposo.b delenia je v převedení velmi jednoduchý a umožňuje účinné vzájomné rozdele- nie alditolov, i takých /napr. galaktitol - glucitol,. manitol - altritol/, ktoré nife je mož-né rozdělit na katexoch cyklízovaných katiónmi alkalických kovov a kovov alkalických zemin.
Podstata sposobu chromatografického delenia alditolov podlá vynálezu spočívá v tom, že zmes alditolov sa chromatografuje elúciou vodou na stípčí katexu v lantanitom cykle. Výhodou navrhovaného sposobu chromatografického delenia alditolov je,xže 211585 211585 2 umožňuje rychle a účinné rozdelenie zmesí tetritolov, pentitolov, hexitolov, heptito-lov, připadne zmesí alditolov s rOznym počtom atómov uhlíka v molekule» dovoluje až 5až 15 váhové zataženie chromatografickej náplně'zmesou aldi.tolov /počítanéna vzduchosuchý ionomenič/, elúcia vodou odstraňuje technické fažkosti s používáním,resp. finálny-m odstráňovanímpufrovacích roztokov a organických rozpúštadiel ako elučných systémóv, ? .·získajú sa alditoly s vysokým stupňom čistoty, . κ / chromatografickú náplň je možné opakované používať bez regenerácie a bez poklesu účin-nosti deleniá prakticky na lubóvolný počet delení. Přiklad l
Zmes .A ’/alitol, D-manitol, D-altritol, galaktitol, D-glucitol, L-iditol/, resp. zmes B/ribitol, L-arabinitol, xylitol, pentaery tr i to 1, galaktitol/, zmes, C /erytritol, D-treitol,·D-glucitol, D-glycero-D-talohepcitol, D-glycero-D-galaktoheptitol/, zmes D /glycerol, D-treitol, D-xylitol, galaktitol, Ď-glycero-D-taloheptitol/ každý alditol á 0,1 g/ sachromatografujú prí teplote miestnosti ná štipci /90 x 0,9 cm/ionomeniča Dowex 50 W, X-8, 200 - 400 mesh'v La-cykle elúciou vodou pri prietoku 15 ml.h · Relativné elučné objemyVr jednotlivých alditolov vztahované na elučný objem pentaerytritolu V » 54 ml, Vr = 1,00sú uvedené v tabulke 1.
Relátívne elučné objemy alditolov pri chromatografii na Dowexe 50 W v La-cykle elúciou vodou
Alditol V r glycerol • 0,99 erytritol 0,97 D-treitol 1,48 ribitol /adonit/ 0,89 L-arabinitol. 1 ,39 D-xylitol 2,52 alitol 0,91 D-manitol 1,20 D-altritol 1 ,35 galaktitol /dulcit/ 1,98 D-glucitol' /eorbit/ ‘2,50 L-iditol 3,15 D-glycero-D-taloheptitol /volemit/ 1,17 D-glycero-D-galaktoheptitol /perzeit/ 1,70 pentaerytritol 1 ,00 Příklad
Zmes /4 g/ D-[2-2h] manitolu a D-[2-2lJ glucitolu /získaná redukciou D-fruktózy deuterí-dom boritosodným, po deionizácii katexom, zahuštění a trojnásobnom odpaření destilačnéhozvyšku s metanolom/ sa chromatografuje na.štipci katexu v La-cykle uvedenom v příklade 1elúciou vodou pri prietoku 18 ml.h čím sanavzájom rozdělia nezreagovaná. východiskováD-fruktoza /0,1 g, elučný objem 34 až 36 ml/^, D-[2-2H]manitol /1,9 g, 54 až 88 ml/ a1D-[2-2H] glucitol /1,9 g, 100 až'16*5 ml/.
Claims (1)
- 3 211585 Příklad 3 Zmes /0,8 g/[3-^h] ribitolu a xylitolu /získaná redukciou erytro-3-pentulózy deuteridom boritosodným/ sa chromatografuje na stípci katexu v La-cykle uvedenom v příklade1 elúciou vodou pri prietoku 40 ml.h \ čím sa získá C3-2Hj ribitol /0,4 g, elučný objem40 až 60 ml/ a [3~h] xylitol /0,4 g 110 až 155 ml/. Uvedený sposob chromatografického delenia alditolov na katexe v lantanitom cykleumožňuje jednoduché a vysokoúcinné delenie zložitých zmesí alditolov, ktoré sú zaujímavépre potravinářsky prieraysel a izotopicky značné pre sledovanie chemických a biochemickýchreakc-ií . Súčasne je možné tento sposob použiť pri preparatívnej príprave niektorých vzácnýchalditolov a v analytíckej chémii sacharidov. PREDMET VYNÁLEZU SpOsob chromatografického delenia alditolov vyznačujúci sa tým, že zmes alditolov sachromatografuje elúciou vodou na štipci katexu v lantanitom cykle. SeyerogrefU. n. p~ sévod 7, Most
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS805579A CS211585B1 (en) | 1979-11-29 | 1979-11-29 | Method of chromatographic separation of alditoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS805579A CS211585B1 (en) | 1979-11-29 | 1979-11-29 | Method of chromatographic separation of alditoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS211585B1 true CS211585B1 (en) | 1982-02-26 |
Family
ID=5430632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS805579A CS211585B1 (en) | 1979-11-29 | 1979-11-29 | Method of chromatographic separation of alditoles |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS211585B1 (cs) |
-
1979
- 1979-11-29 CS CS805579A patent/CS211585B1/cs unknown
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