NO129294B - - Google Patents
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- NO129294B NO129294B NO03728/70*[A NO372870A NO129294B NO 129294 B NO129294 B NO 129294B NO 372870 A NO372870 A NO 372870A NO 129294 B NO129294 B NO 129294B
- Authority
- NO
- Norway
- Prior art keywords
- xylose
- methanol
- water
- cellulose
- hydrolyzate
- Prior art date
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- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 89
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 47
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 21
- 239000001913 cellulose Substances 0.000 claims description 15
- 229920002678 cellulose Polymers 0.000 claims description 15
- 229920005610 lignin Polymers 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000012141 concentrate Substances 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 6
- 235000007319 Avena orientalis Nutrition 0.000 claims description 5
- 239000011121 hardwood Substances 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 241000209761 Avena Species 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000000284 extract Substances 0.000 description 17
- 239000006188 syrup Substances 0.000 description 11
- 235000020357 syrup Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 9
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 9
- 239000002023 wood Substances 0.000 description 9
- 239000000811 xylitol Substances 0.000 description 9
- 235000010447 xylitol Nutrition 0.000 description 9
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 9
- 229960002675 xylitol Drugs 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 8
- 229920002488 Hemicellulose Polymers 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 150000001720 carbohydrates Chemical class 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 150000002972 pentoses Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 5
- 235000014633 carbohydrates Nutrition 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002402 hexoses Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 description 4
- -1 alkane carboxylic acid Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 150000002772 monosaccharides Chemical class 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- 150000004804 polysaccharides Chemical class 0.000 description 4
- 235000018185 Betula X alpestris Nutrition 0.000 description 3
- 235000018212 Betula X uliginosa Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910001023 sodium amalgam Inorganic materials 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000218631 Coniferophyta 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 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
- 241000218922 Magnoliophyta Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 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
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium 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
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 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 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 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
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
-
- 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
- C13K13/002—Xylose
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Description
Fremgangsmåte for fremstilling av xylose. Process for the production of xylose.
Xylitt, som er et søtningsstoff, ble hittil fremstilt ved hydrering av xylose som ble fremstilt ved hydrolyse av til-gjengelige xylan- og celluloseholdige materialer med konsen-trerte eller fortynnede syrer. Den på denne måten erholdte xylosen har den ulempen at den forekommer i en blanding av pentoser, heksoser og lignin. Disse blandinger kan bare med storste vanskelighet og med store utbyttetap oppdeles i sine enkelte komponenter. Denne separasjons- og rensingsprosess har dertil vist seg å-være kostbar og tidskrevende. Xylitol, which is a sweetener, was hitherto produced by the hydration of xylose which was produced by the hydrolysis of available xylan- and cellulose-containing materials with concentrated or dilute acids. The xylose obtained in this way has the disadvantage that it occurs in a mixture of pentoses, hexoses and lignin. These mixtures can only be separated into their individual components with great difficulty and with great loss of yield. This separation and purification process has also proven to be expensive and time-consuming.
Xylose overfores til xylitt ved reduksjon. Reduksjonen av aldehyd- eller ketogrupper i et reduserende sukker, som f.eks. reduksjonen av xylose til xylitt, kan- gjennomfores ved hjelp av katalytiske eller kjemisk kjente metoder. Man har f.eks. redusert xylose til xylitt ved hjelp av natriumamalgam eller ved hjelp av hydrogen-gass i nærvær av en nikkelkatalysator. Denne reaksjonen kan imidlertid bare gjennomfores med ren xylose, da små forurensninger, særlig lignin, forgifter kata-lysatoren. Reduksjonen bringes derved til opphor og en videre reduksjon umuliggjbres. Xylose is transferred to xylitol by reduction. The reduction of aldehyde or keto groups in a reducing sugar, such as the reduction of xylose to xylitol can be carried out using catalytic or chemically known methods. One has e.g. reduced xylose to xylitol by means of sodium amalgam or by means of hydrogen gas in the presence of a nickel catalyst. However, this reaction can only be carried out with pure xylose, as small impurities, especially lignin, poison the catalyst. The reduction is thereby brought to an end and a further reduction is made impossible.
For å overvinne disse ulemper, er det for fremstillingen av xylose foreslått å anvende utgangsmaterialer med hoyt xylose-innhold og lavt lignininnhold. Disse materialer er imidlertid temmelig kostbare. Dertil må forurensninger i xylosen fraskilles, og dette betyr hoye utbyttetap og kostbare og tidskrevende prosesser. Det har derfor lengs vært et behov for en fremgangsmåte, som ut fra billige cellulosematerialer var i stand til å gi en praktisk talt kjemisk ren xylose uten å måtte anvende vanskelig gjennomførbare separasjons-prosesser. Den foreliggende oppfinnelse muliggjor fremstillingen av en praktisk talt ren xylose som kan anvendes for direkte overforing til xylitt. Denne xylosen kan fremstilles av xylan- og celluloseholdige materialer. For å felle ut ligninet behandler man forst disse materialer med et surt hydrolysemiddel i en vandig losning. Den erholdte vandige losningen lar man derefter gjennomstrømme en ione-veksler. Eluatet torkes og opploses i metanol, hvorved xylose erholdes To overcome these disadvantages, it is proposed for the production of xylose to use starting materials with a high xylose content and low lignin content. However, these materials are quite expensive. In addition, contaminants in the xylose must be separated, and this means high yield losses and expensive and time-consuming processes. There has therefore long been a need for a method which, based on cheap cellulose materials, was able to produce a practically chemically pure xylose without having to use difficult-to-implement separation processes. The present invention enables the production of a practically pure xylose which can be used for direct conversion to xylitol. This xylose can be produced from xylan- and cellulose-containing materials. To precipitate the lignin, these materials are first treated with an acidic hydrolysis agent in an aqueous solution. The aqueous solution obtained is then allowed to flow through an ion exchanger. The eluate is dried and dissolved in methanol, whereby xylose is obtained
i krystallinsk form. Den på denne måten isolerte krystallinske xylosen kan opploses i vann, og på vanlig måte hydreres til xylitt. in crystalline form. The crystalline xylose isolated in this way can be dissolved in water and hydrated to xylitol in the usual way.
Fremgangsmåten ifolge oppfinnelsen vedrorer således fremstillingen av krystallinsk xylose ved hydrolysering av xylan og celluloseholdige materialer, fraskilling av hydrolysatet fra ligninene, rensing av hydrolysatet ved å la dette gjennomstromme en ioneveksler, konsentrering: av hydrolysatet samt isolering av krystallinsk xylose fra konsentratet og er karakterisert ved at det rensede hydrolysatet oppkonsentreres til et vanninnhold på 5 - 15 vekts-%, og at xylosen utfelles fra konsentratet ved tilsetning av minst 0,5 ml metanol pr. g konsentrat, og at den krystallinske xylosen isoleres fra den metanolholdige lbsningen. The method according to the invention thus relates to the production of crystalline xylose by hydrolyzing xylan and cellulose-containing materials, separating the hydrolyzate from the lignins, purifying the hydrolyzate by passing it through an ion exchanger, concentrating: the hydrolyzate and isolating crystalline xylose from the concentrate and is characterized by the purified hydrolyzate is concentrated to a water content of 5 - 15% by weight, and that the xylose is precipitated from the concentrate by adding at least 0.5 ml of methanol per g concentrate, and that the crystalline xylose is isolated from the methanol-containing solution.
Den ifolge oppfinnelsen fremstilte xylosen oppviser en så The xylose produced according to the invention exhibits a
hoy renhetsgrad at den uten videre rensing kan hydreres til xylitt, og dette kan gjores uten risiko for. at hydreringen skal opphore. Ved hjelp av denne fremgangsmåten kan man dessuten erholde en praktisk ren xylose fra de vandige hemicellu-loseekstraktene, og dette uten å måtte anvende kostbare og vanskelig gjennomforbare separasjons- og rensingsprosesser. Slike vandige hemicelluloseekstrakter er f.eks. tre-ekstrakter, hvilke representerer avfallsprodukter i celluloseindustrien. high degree of purity that it can be hydrated to xylitol without further purification, and this can be done without risk of that the hydration should stop. With the help of this method, a practically pure xylose can also be obtained from the aqueous hemicellulose extracts, and this without having to use expensive and difficult separation and purification processes. Such aqueous hemicellulose extracts are e.g. wood extracts, which represent waste products in the cellulose industry.
Ifolge oppfinnelsen erholdes xylose som er isolert fra hemicelluloseholdige materialer. For fremstillingen av xylose kan man anvende xylan- eller celluloseholdig materiale. Dette hemicelluloseholdige materiale inneholder vanligvis ligniner og karbohydrater, dvs. blandinger av monomere og polymere former av sakkarider, f.eks. heksoser og pentoser. Materialene, som skal anvendes, kan foreligge i torket eller malt form eller i form av et vandig ekstrakt. According to the invention, xylose is obtained which is isolated from hemicellulose-containing materials. For the production of xylose, xylan- or cellulose-containing material can be used. This hemicellulosic material usually contains lignins and carbohydrates, i.e. mixtures of monomeric and polymeric forms of saccharides, e.g. hexoses and pentoses. The materials to be used can be in dried or ground form or in the form of an aqueous extract.
Egnede hemicelluloseholdige materialer for gjennomføring av fremgangsmåten ifolge oppfinnelsen er f.eks. angiospermer, Suitable hemicellulose-containing materials for carrying out the method according to the invention are e.g. angiosperms,
dvs. såvel enkimbladede planter, som gress (f.eks. havre, bagasse eller mais) som også tokimbladede planter, som bartrær og lovtrær, f.eks. bok, poppel, bjork og or). Av disse utgangsmaterialer foretrekkes bjorkeved, som kan erholdes i store mengder og som dessuten representerer liten okonomisk verdi. Særlig egnede er nysnittede og lufttorkede.bjorkeved-spon, spelthavre og maiskolber. i.e. both monocotyledonous plants, such as grass (e.g. oats, bagasse or maize) as well as dicotyledonous plants, such as conifers and deciduous trees, e.g. beech, poplar, birch and alder). Of these starting materials, birch wood is preferred, which can be obtained in large quantities and which also represents little economic value. Particularly suitable are freshly cut and air-dried birch wood shavings, spelled oats and maize cobs.
De ifolge oppfinnelsen som utgangsstoffer anvendte cellulose-holdige produkter kan f.eks. være ekstrakter, som erholdes ved behandling av hemicellulosemateriale med vann eller vanndamp ved temperaturer fra 110 - 190°C og ved et trykk på The cellulose-containing products used as starting materials according to the invention can e.g. be extracts, which are obtained by treating hemicellulose material with water or steam at temperatures from 110 - 190°C and at a pressure of
1,05 - 1,40 kg/cm 2. Vanndampen hhv. vannet ekstraherer de i 1.05 - 1.40 kg/cm 2. The water vapor or the water they extract in
cellulosematerialet forekommende karbohydrater og lignin. carbohydrates and lignin present in the cellulose material.
De erholdte ekstrakter inneholder vanligvis ligniner, polysakkarider og monosakkarider. The extracts obtained usually contain lignins, polysaccharides and monosaccharides.
Monosakkaridene er f.eks. pentoser og heksoser, som glukose, mannose, galaktose, xylose og arabinose. Polysakkaridene er f.eks. de polymere formene av heksoser og pentoser. Vanligvis inneholder de vandige ekstraktene hemicelluloseholdige materialer, f.eks. inneholder de vandige tre-ekstraktene (beregnet på torrstoffinnholdet) 5-30 vekts-% ligniner og 95 - 70 vekts-% karbohydrater inklusive polysakkarider og monosakkarider. De vandige, hemicelluloseholdige ekstraktene inneholder vanligvis 10 - 40 vekts-% xylose, beregnet på eks-traktets torrstoffinnhold. The monosaccharides are e.g. pentoses and hexoses, such as glucose, mannose, galactose, xylose and arabinose. The polysaccharides are e.g. the polymeric forms of hexoses and pentoses. Usually the aqueous extracts contain hemicellulosic materials, e.g. the aqueous wood extracts (calculated on the dry matter content) contain 5-30% by weight lignins and 95-70% by weight carbohydrates including polysaccharides and monosaccharides. The aqueous, hemicellulose-containing extracts usually contain 10-40% xylose by weight, calculated on the dry matter content of the extract.
De vandige hemicelluloseholdige ekstraktene -fremstilles som regel i form av en vandig losning eller et konsentrat med et torrstoffinnhold på 10 - 30 vekts-% og et vanninnhold på 90 - 70 vekts-%. Mengden torrstoffandel i treekstrakten varierer med årstiden, tresorten og treets behandlingsmåte. F.eks. erholder man mer pentose fra hårdtre enn fra myktre. Karbohydratene i hydrolysatet fra hårdtre er fortrinnsvis pentoser. På den annen side består karbohydratene i ekstraktene fra myktre hovedsakelig av heksoser. The aqueous hemicellulose-containing extracts - are usually produced in the form of an aqueous solution or a concentrate with a dry matter content of 10 - 30% by weight and a water content of 90 - 70% by weight. The amount of dry matter in the wood extract varies with the season, the type of wood and the way the wood is treated. E.g. more pentose is obtained from hardwood than from softwood. The carbohydrates in the hydrolyzate from hardwood are preferably pentoses. On the other hand, the carbohydrates in the softwood extracts consist mainly of hexoses.
De ovennevnte ekstrakter representerer avfallsprodukter i celluloseindustrien. The above extracts represent waste products in the cellulose industry.
I det forste trinnet av den foreliggende fremgangsmåten hydrolyseres xylan- og celluloseholdige materialer med et surt hydrolysemiddel. For dette kan man anvende et eller annet surt hydrolysemiddel, f.eks. en uorganisk mineralsyre, som svovelsyre og saltsyre eller en organisk syre, f.eks. en halo-genert lavere alkankarboksylsyre, som trikloreddiksyre og monokloreddiksyre. Uorganiske syrer, f.esks. svovelsyre, foretrekkes vanligvis. De uorganiske syrene kan anvendes enten i fortynnet eller i konsentrert form. Deit sure hydrolysemidlet kan foreligge i sin vandige losning i en mengde på 1 vekts- In the first step of the present method, xylan- and cellulose-containing materials are hydrolysed with an acidic hydrolysis agent. For this, one can use some kind of acid hydrolysis agent, e.g. an inorganic mineral acid, such as sulfuric and hydrochloric acid or an organic acid, e.g. a halogenated lower alkane carboxylic acid, such as trichloroacetic acid and monochloroacetic acid. Inorganic acids, e.g. sulfuric acid, is usually preferred. The inorganic acids can be used either in diluted or concentrated form. The acidic hydrolysis agent can be present in its aqueous solution in an amount of 1 wt.
% til 20 vekts-%, beregnet på torrstoffinnholdet i % to 20% by weight, calculated on the dry matter content in
cellulosematerialet som skal hydrolyseres. Ved syrebehandlin-gen hydrolyseres polysakkaridene til monosakkarider, og ligninene omdannes til uloselig materiale, som kan fjernes ved filtrering. Hydrolysen kan gjennomfores ved romtemperatur, f.eks. ved ca. 20°C. En hoyere temperatur, f.eks. 55- 150°C, er imidlertid foretrukket. Hydrolysen kan foretas ved såvel atmosfærisk trykk som også ved hoyere trykk. Det foretrekkes å gjennomfore hydrolysen ved hoyere trykk, dvs. ved 0,5 - 10 kg/cm . the cellulose material to be hydrolysed. During the acid treatment, the polysaccharides are hydrolysed into monosaccharides, and the lignins are converted into insoluble material, which can be removed by filtration. The hydrolysis can be carried out at room temperature, e.g. at approx. 20°C. A higher temperature, e.g. 55-150°C, however, is preferred. The hydrolysis can be carried out at atmospheric pressure as well as at higher pressure. It is preferred to carry out the hydrolysis at higher pressures, i.e. at 0.5 - 10 kg/cm .
Det ved filteringen erholdte klare vandige hydrolysatet filtreres gjennom en ione-veksler. Til dette kan man anvende en eller annen kation- eller anion-veksler. The clear aqueous hydrolyzate obtained by filtration is filtered through an ion exchanger. For this, one can use one or another cation or anion exchanger.
De anvendte anionveksler-resinater er f.eks. korsforgrenede polystyroler,.som inneholder kvartære ammoniumgrupper eller substituerte aminogrupper, som -N (C3Hg)2-grupper, aminogrupper som inneholder polykondensasjonsprodukter av fenol og formaldehyd, polymerisasjonsprodukter av aromatiske aminer og formaldehyd, guanidin/formaldehyd- resinater, polyaminer og fenol/ formaldehyd-resinater. Disse anionveksler-resinater forekommer i handelen under folgende merker: The anion exchanger resinates used are e.g. cross-branched polystyrenes, containing quaternary ammonium groups or substituted amino groups, such as -N (C3Hg)2 groups, amino groups containing polycondensation products of phenol and formaldehyde, polymerization products of aromatic amines and formaldehyde, guanidine/formaldehyde resinates, polyamines and phenol/formaldehyde resinates. These anion exchanger resinates are available in the trade under the following brands:
Som kationvekslere kan man anvende ett eller annet veksler-resinat. Foretrukkede kationveksler-resinater er atomære sulfonsyrekationveksler-resinater, som f.eks. resinater av polystyrolsulfonsyretype, som forekommer i handelen under merket "Amberlite IR-120" og "Dowex 50". As cation exchangers, one can use one or another exchanger resinate. Preferred cation exchange resinates are atomic sulfonic acid cation exchange resinates, such as e.g. resinates of the polystyrene sulfonic acid type, which appear in the trade under the brands "Amberlite IR-120" and "Dowex 50".
Ifolge en foretrukket utforelsesform filtreres den vandige losningen forst gjennom en kationveksler og derefter gjennom en anionveksler. Den vandige lbsningen kan imidlertid også filtreres gjennom enten en kationveksler eller en anionveksler. According to a preferred embodiment, the aqueous solution is first filtered through a cation exchanger and then through an anion exchanger. However, the aqueous solution can also be filtered through either a cation exchanger or an anion exchanger.
Ifolge oppfinnelsen ble det videre oppnådd at den vandige losningen avfarges ved filtrering gjennom ioneveksleren og at eventuelle medrevne ligninpartikler fjernes. According to the invention, it was further achieved that the aqueous solution is decoloured by filtration through the ion exchanger and that any entrained lignin particles are removed.
Ifolge oppfinnelsen tbrkes til slutt det fra ioneveksleren erholdte eluatet til et vanninnhold på 5 - 15 vekts-%. Tbrk-r ningsmetoden er valgfri og kan f.eks., bestå i en fordampning, trommeltbrkning eller spraytbrkning. Fordampningen kan fore- According to the invention, the eluate obtained from the ion exchanger is finally used to a water content of 5 - 15% by weight. The drying method is optional and can, for example, consist of evaporation, drum drying or spray drying. The evaporation can occur
tas ved hoyere temperaturer og redusert trykk. Det torkede produktet kan enten foreligge som et pulver med ca. 5 vekts-% vann eller som en seigtflytende sirup med c:a. 15 vekts-% vann. taken at higher temperatures and reduced pressure. The dried product can either be available as a powder with approx. 5% by weight of water or as a viscous syrup with approx. 15% by weight water.
Det på denne måten tbrkede eluatet behandles derefter med metanol. Det tbrkede eluatets pH-verdi skal ligge mellom 4 og 8. Denne kan, hvis nbdvendig, korrigeres ved tilsetning av små mengder av et alkali- eller jordalkalimetallhydroksyd eller et alkalimetall- eller jordalkalimetallsalt. For dette kan man anvende f.eks. natriumhydroksyd, kaliumhydroksyd, kalsiumhydroksyd, magnesiumhydroksyd, natriumbikarbonat, natrium-fosfat eller kalsiumkarbonat. Korrigeringen av pH-verdien kan foretas såvel for som efter tbrkningen av eluatet. The eluate obtained in this way is then treated with methanol. The pH value of the diluted eluate must lie between 4 and 8. This can, if necessary, be corrected by adding small amounts of an alkali or alkaline earth metal hydroxide or an alkali metal or alkaline earth metal salt. For this, you can use e.g. sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, sodium bicarbonate, sodium phosphate or calcium carbonate. The correction of the pH value can be carried out both before and after the use of the eluate.
Det tbrkede eluatet bringes i losning ved tilsetning av metanol. Den anvendte mengden metanol skal være tilstrekkelig for å opp-lbse det tbrkede eluatet. Det er nbdvendig med minst 0,5 ml metanol pr. lg tbrket eluat. Det kan imidlertid også anvendes et stbrre overskudd av metanol, f.eks. 100 ml metanol pr. lg tbrket eluat. Mengder på mer enn 100 ml metanol pr. 1 g tbrket eluat anvendes sjelden da det herved ikke oppnås noen fordeler. The diluted eluate is brought into solution by adding methanol. The amount of methanol used must be sufficient to dissolve the diluted eluate. At least 0.5 ml of methanol per Ig used eluate. However, a greater excess of methanol can also be used, e.g. 100 ml of methanol per Ig used eluate. Quantities of more than 100 ml of methanol per 1 g of used eluate is rarely used as no benefits are achieved.
Det tbrkede eluatet kan blandes på vanlig måte med metanolen. Temperatur og trykk er herved ikke kritiske. The diluted eluate can be mixed in the usual way with the methanol. Temperature and pressure are not critical here.
Tilsetningen av metanol kan skje ved romtemperatur eller også The addition of methanol can take place at room temperature or also
ved hoyere eller lavere temperaturer. En temperatur på at higher or lower temperatures. A temperature of
10 - 50°C er imidlertid foretrukket. However, 10 - 50°C is preferred.
Det ble funnet at metanol oppldser samtlige materialer i den hydrolyserte og tidligere gjennom ioneveksler filtrerte vandige ekstrakten, med unntagelse av den i ekstrakten forekommende xylose. I metanolen, som inneholder hele ekstrakten, erholdes derfor praktisk talt ren krystallinsk xylose. Den således erholdte xylosen er fri for samtlige i det opprinnelige cellulosematerialet forekommende forurensninger, og er således praktisk talt kjemisk ren. It was found that methanol dissolves all materials in the hydrolysed and previously filtered through ion exchanger aqueous extract, with the exception of the xylose present in the extract. In the methanol, which contains the entire extract, practically pure crystalline xylose is therefore obtained. The xylose thus obtained is free of all impurities occurring in the original cellulose material, and is thus practically chemically pure.
Xylosen, som er utkrystallisert i metanol-losningen, avskilles The xylose, which has crystallized out in the methanol solution, is separated
på vanlig måte ved filtrering og omdannes i xylitt. in the usual way by filtration and converted into xylitol.
For hydrering anvendes de vanlige metoder for omdannelse av For hydration, the usual methods for conversion of
et aldehyd eller keton til en alkohol. Den krystallinske xylosen hydreres vanligvis i et vandig medium til xylitt. Hydreringen kan foretas på kjemisk eller katalytisk veg, an aldehyde or ketone to an alcohol. The crystalline xylose is usually hydrated in an aqueous medium to xylitol. The hydrogenation can be carried out chemically or catalytically,
f.eks. ved hjelp av natriumamalgam eller et komplekst metall-hydrid, som litiumborhydrid eller natriumborhydrid, fortrinnsvis med hydrogen og en edelmetallkatalysator, som platina eller palladium. e.g. using sodium amalgam or a complex metal hydride, such as lithium borohydride or sodium borohydride, preferably with hydrogen and a noble metal catalyst, such as platinum or palladium.
De folgende eksempler illustrerer oppfinnelsen. The following examples illustrate the invention.
EKSEMPEL 1 EXAMPLE 1
Hydrolyse av utgangsmaterialet Hydrolysis of the starting material
235 ml vann tilsettes 200 g Masonexsirup (et vandig tre-ekstrakt) med folgende sammensetning: 235 ml of water is added to 200 g of Masonex syrup (an aqueous wood extract) with the following composition:
Masonexsirupen blandes med vannet og dette tilsettes 8,8 ml konsentrert svovelsyre. Den erholdte morkebrune, seigtflytende lbsningen deles i fire deler og oppvarmes 3,5 timer ved 120°C i fire lukkede 200 ml tykkveggede glasskolber. De svartbrune hydrolysatene avkjoles, forenes, nøytraliseres med 11,9 g kalsiumhydroksyd og filtreres. Den klare lbsningen filtreres gjennom en ionevekslingssbyle, som inneholder 350 ml Permutit DR (et anionisk kondensert fenylendiamin/formaldehydresinat), med en hastighet på 6 ml/min. Det klare eluatet er svakt gul-farget, ioneveksler-resinatet vaskes med 1400 ml vann. Eluatet forenes med vaskevannet og konsentreres under redusert trykk til 200 ml. Det gjenværende bunnfallet (torrstoffinnhold: 5,6 g) , som består av kalsiumfiltrat, avf.Lltreres og vaskes med en liten mengde vann. Filtratet inneholder 30,6 g xylose. The Masonex syrup is mixed with the water and 8.8 ml of concentrated sulfuric acid is added to this. The obtained dark brown, viscous solution is divided into four parts and heated for 3.5 hours at 120°C in four closed 200 ml thick-walled glass flasks. The black-brown hydrolysates are cooled, combined, neutralized with 11.9 g of calcium hydroxide and filtered. The clear solution is filtered through an ion exchange bubble, containing 350 ml of Permutit DR (an anionic condensed phenylenediamine/formaldehyde resinate), at a rate of 6 ml/min. The clear eluate is slightly yellow-coloured, the ion exchanger resinate is washed with 1400 ml of water. The eluate is combined with the washing water and concentrated under reduced pressure to 200 ml. The remaining precipitate (dry matter content: 5.6 g), which consists of calcium filtrate, is filtered off and washed with a small amount of water. The filtrate contains 30.6 g of xylose.
EKSEMPEL 2 EXAMPLE 2
Fremstilling av xylose Production of xylose
Det ifolge eksempel 1 fremstilte filtratet inndampes under redusert trykk ved 45°c. Den erholdte sirupen (31,9 g) opploses i 25,0 ml metanol, tilsettes noen pode-krystaller av D-xylose og omrbres 1 time ved romtemperatur. Under omrbring avkjbles krystall-suspensjonen 5 timer i et is/vann-bad. Suspensjonen får derefter stå kalt 5 dager og filtreres der-eftér. Den erholdte xylosen vaskes tre ganger med hver gang 15 ml -10°C kald metanol og tbrkes under redusert trykk ved 35°C til konstant vekt erholdes. The filtrate prepared according to example 1 is evaporated under reduced pressure at 45°c. The resulting syrup (31.9 g) is dissolved in 25.0 ml of methanol, a few seed crystals of D-xylose are added and stirred for 1 hour at room temperature. During stirring, the crystal suspension is cooled for 5 hours in an ice/water bath. The suspension is then allowed to stand cold for 5 days and then filtered. The xylose obtained is washed three times with each time 15 ml -10°C cold methanol and dried under reduced pressure at 35°C until a constant weight is obtained.
EKSEMPEL 3 EXAMPLE 3
480,0 g vann tilsettes 59 ml konsentrert saltsyre (37 vekts-%) og 120,0 g tbrket, malt spelthavre med folgende sammensetning: 480.0 g of water is added to 59 ml of concentrated hydrochloric acid (37% by weight) and 120.0 g of dried, ground spelled oats with the following composition:
Den erholdte suspensjonene hydrolyseres 3 timer ved 118 - 120°. Den erholdte blandingen avkjbles og sentrifugeres. De faste stoffene vaskes med 400 ml vann. Det erholdte klare og gule filtratet, som inneholder 25,8 g xylose, avioniseres på den måten at det efter hverandre får gjennomstromme to ioneveksler-soyler, hvorved den forste sbylen er fylt med 70 ml Amberlite IR-120 (H<+>) og den andre soylen inneholder 170 ml Amberlite IRA-93 (0H~). Filtreringshastigheten er 7 ml/min. Hver soyle vaskes med 150 ml vann. Det med vaskevannet forenede eluatet konsentreres under redusert trykk ved 40 - 44°C til en sirup (vekt 42,8 g, vanninnhold 4,1 g). Sirupen tilsettes 43,9 ml metanol. Den erholdte gule lbsningen avkjbles til -10°C og ved denne temperaturen omrbres 48 timer. Den krystallinske xylose-holdige suspensjonen filtreres, vaskes fire ganger med hver gang 10 ml -10°C kald metanol og tbrkes til konstant vekt erholdes. Man erholder 18,0 g xylose [renhetsgrad: 94,0%; utbytte: 14%, beregnet på anvendt spelthavre]. The obtained suspensions are hydrolysed for 3 hours at 118 - 120°. The resulting mixture is cooled and centrifuged. The solids are washed with 400 ml of water. The resulting clear and yellow filtrate, which contains 25.8 g of xylose, is deionized in such a way that it is allowed to flow through two ion exchange coils one after the other, whereby the first coil is filled with 70 ml of Amberlite IR-120 (H<+>) and the second soil contains 170 ml of Amberlite IRA-93 (0H~). The filtration rate is 7 ml/min. Each soil is washed with 150 ml of water. The eluate combined with the washing water is concentrated under reduced pressure at 40 - 44°C to a syrup (weight 42.8 g, water content 4.1 g). 43.9 ml of methanol is added to the syrup. The yellow solution obtained is cooled to -10°C and stirred at this temperature for 48 hours. The crystalline xylose-containing suspension is filtered, washed four times with each time 10 ml -10°C cold methanol and used until a constant weight is obtained. 18.0 g of xylose is obtained [purity: 94.0%; yield: 14%, calculated on spelled oats used].
EKSEMPEL 4 EXAMPLE 4
Hydrolyse av utgangsmateriale Hydrolysis of starting material
517 ml vann tilsettes 100 g Masonexsirup (et vandig tre-ekstrakt) med folgende sammensetning: 517 ml of water is added to 100 g of Masonex syrup (an aqueous wood extract) with the following composition:
Masonexsirupen blandes med vann og tilsettes 4,4 ml konsen- The Masonex syrup is mixed with water and 4.4 ml of concen-
trert svovelsyre. 100 ml av denne lbsningen, som inneholder 16,7 g Masonexsirup, oppvarmes 6 timer ved. 120°C i en lukket, tykkvegget 200 ml glasskolbe. Det erholdte svartbrune hydro- triturated sulfuric acid. 100 ml of this solution, which contains 16.7 g of Masonex syrup, is heated for 6 hours by 120°C in a closed, thick-walled 200 ml glass flask. The obtained black-brown hydro-
lysatet avkjbles, filtreres og vaskes med 80 ml vann. Det inneholder 2,63 g xylose. Filtratet filtreres gjennom 120 ml Amberlite IR-120 (H<+>) og derefter gjennom 120 ml Amberlite IRA-93 (0H~). Hver ionevekslersbyle vaskes med 500 ml vann. the lysate is cooled, filtered and washed with 80 ml of water. It contains 2.63 g of xylose. The filtrate is filtered through 120 ml of Amberlite IR-120 (H<+>) and then through 120 ml of Amberlite IRA-93 (0H~). Each ion exchanger bubble is washed with 500 ml of water.
EKSEMPEL 5 EXAMPLE 5
Fremstilling av xylose Production of xylose
Det ifolge eksempel 4 fremstilte" eluatet slåes sammen med vaske-lbsningene og inndampes under redusert trykk ved 45°C, hvorved man erholder 7,2 g sirup som inneholder 1 g vann. Denne sirupen opploses i 7,0 ml metanol. Lbsningen innpodes med noen pode-krystaller av D-xylose. Lbsningen omrbres 5 timer i et is- The "eluate prepared according to example 4" is combined with the washing solutions and evaporated under reduced pressure at 45°C, whereby 7.2 g of syrup containing 1 g of water is obtained. This syrup is dissolved in 7.0 ml of methanol. The solution is inoculated with some seed crystals of D-xylose The solution is stirred for 5 hours in an ice-
vann-bad og får stå 5 dager avkjblt. Den erholdte suspen- water-bath and allowed to stand for 5 days unrefrigerated. The obtained suspension
sjonen filtreres. Den gjenværende xylosen vaskes 3 ganger med hver gang 5 ml -10°C kald metanol og tbrkés under redusert trykk ved 35°C til konstant vekt erholdes. Man erholder 0,26 g xylose med en renhetsgrad på 94,4%. tion is filtered. The remaining xylose is washed 3 times with each time 5 ml -10°C cold methanol and dried under reduced pressure at 35°C until a constant weight is obtained. 0.26 g of xylose with a degree of purity of 94.4% is obtained.
Claims (3)
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US86335869A | 1969-10-02 | 1969-10-02 |
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CH (1) | CH541531A (en) |
DE (1) | DE2047897B2 (en) |
FI (1) | FI51375C (en) |
FR (1) | FR2064865A5 (en) |
GB (1) | GB1273497A (en) |
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US6675495B2 (en) | 1997-10-30 | 2004-01-13 | Valeurs Bois Industrie | Method for drying saw timber and device for implementing said method |
CN101824054B (en) * | 2009-06-30 | 2012-01-04 | 山东福田药业有限公司 | Xylose production and purification process |
-
1970
- 1970-09-18 CH CH1387470A patent/CH541531A/en not_active IP Right Cessation
- 1970-09-29 DE DE2047897A patent/DE2047897B2/en not_active Withdrawn
- 1970-10-01 FR FR7035489A patent/FR2064865A5/fr not_active Expired
- 1970-10-01 FI FI702678A patent/FI51375C/en active
- 1970-10-01 NO NO03728/70*[A patent/NO129294B/no unknown
- 1970-10-01 GB GB46711/70A patent/GB1273497A/en not_active Expired
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DE2047897B2 (en) | 1978-06-08 |
ZA706756B (en) | 1971-07-28 |
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FR2064865A5 (en) | 1971-07-23 |
GB1273497A (en) | 1972-05-10 |
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