CS274022B1 - 0-acetyl-(4-0-methyl-alpha-d-glucorono)-beta-d-xylan - Google Patents
0-acetyl-(4-0-methyl-alpha-d-glucorono)-beta-d-xylan Download PDFInfo
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- CS274022B1 CS274022B1 CS760888A CS760888A CS274022B1 CS 274022 B1 CS274022 B1 CS 274022B1 CS 760888 A CS760888 A CS 760888A CS 760888 A CS760888 A CS 760888A CS 274022 B1 CS274022 B1 CS 274022B1
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- Prior art keywords
- xylan
- methyl
- acetyl
- glucorono
- minutes
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- 229920001221 xylan Polymers 0.000 title claims abstract description 30
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006467 substitution reaction Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 abstract 2
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 description 7
- 229920002488 Hemicellulose Polymers 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 150000004804 polysaccharides Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 102100032843 Beta-2-syntrophin Human genes 0.000 description 1
- 108050004003 Beta-2-syntrophin Proteins 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 241000726768 Carpinus Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
- 241000219000 Populus Species 0.000 description 1
- 150000004075 acetic anhydrides Chemical class 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
at)at)
Účelom riešenia je příprava novej zlúčeniny O-acetyl(4-0-metyl- -D-glukuróno) /3 -D-xylánu s lepšími vlastnosťami. Uvedený účel sa dosiahne O-acetyl-(4-0-metyl- ©4 -D-glukuróno)- /3 -D-xylánom na báze základných štrukturálnych jednotiek všeobecných vzorcov,kde R znamená vodík alebo acetylovú skupinu so stupňom substitúcie 0,1 až 1,5, pripravitel'ný tak, že (4-0-metyl- ob -D-glukuróno)- /5 -D-xylánu sa aktivuje v rozpúšťadle, kyselině trifluoroctovej po dobu alespoň 5 minút pri teplote 10 až 30 c a následné sa acetyluje anhydridom kyseliny octovej pri teplote 10 až 30 C po dobu 5 až 300 minút, pričom vzájomný hmotnostný poměr (4-0-metyl-ov -D-glukuróno)- /3 -D-xylánu, kyseliny trifluoroctovej a anhydridů kyseliny octovej je 1 : 0,8 až 25 ! 0,7 až 25. O-Acetyl-(4-0-metyl- oO -D-glukuróno)- /3 -D-xylán má použitie v chemickom priemysle.The purpose of the solution is to prepare a novel compound O-acetyl (4-O-methyl-D-glucuron) / 3-D-xylan with better properties. This is achieved by O-acetyl- (4-O-methyl-4-D-glucurono) - 3-D-xylan based on basic structural units of the general formulas wherein R is hydrogen or acetyl with a degree of substitution of 0.1 to 1.5, obtainable by (4-O-methyl-ob-D-glucurono) -? - D-xylan being activated in a solvent, trifluoroacetic acid for at least 5 minutes at a temperature of 10 to 30 c and subsequent is acetylated with acetic anhydride at 10 to 30 ° C for 5 to 300 minutes, the ratio by weight of (4-O-methyl-D-glucurono) -? -D-xylan, trifluoroacetic acid and acetic anhydride to each other being 1: 0.8 to 25! 0.7 to 25. O-Acetyl- (4-O-methyl-10-D-glucurono) - 3 -D-xylan has utility in the chemical industry.
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CS 274022 BlCS 274022 Bl
Vynález sa týká O-acetyl-(4-0-metyl- -D-glukuróno)- -D-xylánu.The present invention relates to O-acetyl- (4-O-methyl-D-glucurono) -D-xylan.
Polysacharidy nachádzajú čoraz vačšie uplatnenie v praxi (P. A. Stanford, J. Baird: The Polysaccharides, Academie Press, New York, 1983, vol. 2, str. 411). Okrem celulózy nachádzajú uplatnenie aj necelulózové polysacharidy. V mnohých prípadoch je nutné modifikovat' hydroxylové skupiny týchto zlúčenín, aby sa stali rozpustné vo vodě aj nevodných rozpúšťadlách. Toto umožní ich použitie ako přísady do farbív, lakov, filmotvorných zlúčenín, plniv, pomocných chemikálií a ako medziproduktov pre 9alŠie modifikácie a aplikácie. Doteráz známe postupy acylácie hemicelulóz modifikujú substrát v heterogénnej fáze alebo používajú rozpúštadlá degradujúce substrát /CS AO 210 220; N. I. Nikitin: Chimija dřeva, SNTL, Praha, 1956, str. 195; P. E. Gardner, Μ. Y. Chány: Tappi 57 (8), 71 (1974); J. Kocourek, C. E. Ballou: J. Bacteriol. 100, 1175 (1989)/. Nevýhodou týchto postupov je vysoký stupeň substitúcie a nízké výťažky produktu. Starým postupom acetylácie hemicelulóz sa získal produkt s vysokým stupňom substitúcie (DS^2). Doteráz sa nepřipravil O-acetyl-(4-O-acetyl- oo -D-glukuróno)- /3 -D-xylán so stupňom substitúcie nižším ako 1-5.Polysaccharides find increasing use in practice (P.A. Stanford, J. Baird: The Polysaccharides, Academic Press, New York, 1983, vol. 2, p. 411). In addition to cellulose, non-cellulosic polysaccharides also find application. In many cases, it is necessary to modify the hydroxyl groups of these compounds to become soluble in both water and non-aqueous solvents. This will allow them to be used as additives to dyes, lacquers, film-forming compounds, fillers, auxiliary chemicals and as intermediates for further modifications and applications. The hitherto known acylation procedures of hemicelluloses modify the substrate in a heterogeneous phase or use substrate degrading solvents / CS AO 210 220; NI Nikitin: Chimija dreva, SNTL, Prague, 1956, p. 195; P. E. Gardner, Μ. Y. Khan: Tappi 57 (8), 71 (1974); J. Kocourek, C.E. Ballou: J. Bacteriol. 100, 1175 (1989)]. A disadvantage of these processes is the high degree of substitution and low product yields. The old hemicellulose acetylation procedure yielded a product with a high degree of substitution (DS ^ 2). To date, O-acetyl- (4-O-acetyl-β-D-glucurono) - β-D-xylan with a degree of substitution of less than 1-5 has not been prepared.
Tieto nevýhody odstraňuje tento vynález. Podstatou vynálezu je O-acetyl-(4-O-metyl- íX/ -D-glukuróno)-./3 -D-xylán na báze základných štrukturálnych jednotiek všeobecných vzorcovThese disadvantages are overcome by the present invention. The present invention provides O-acetyl- (4-O-methyl-1 H -D-glucurono) -. Beta.-D-xylan based on the basic structural units of the general formulas
kde R znamená sodík alebo acetylovú skupinu so stupňom substitúcie 0,1 až 1,5, pripravitel'ný tak, že (4-O-metyl- ob -D-glukuróno)- /3 -D-xylán sa aktivuje v rozpúšťadle, kyselině trifluoroctovej po dobu aspoň 5 minút pri teplote 10 až 30 c a následné acetyluje anhydridom kyseliny octovej pri teplote 10 až 30 ’c po dobu 5 až 300 minút, pričom vzájomný hmotnostný poměr (4-O-metyl- e</ -D-glukuróno,-.£> -D-xylánu, kyseliny trifluoroctovej a anhydridů kyseliny octovej je 1 : 0,8 až 25 : 0,7 až 25.wherein R is sodium or acetyl having a degree of substitution of 0.1 to 1.5, obtainable by (4-O-methyl-ob-D-glucuronium) -? - D-xylan being activated in a solvent, acid trifluoroacetic acid for at least 5 minutes at a temperature of 10 to 30 c and subsequently acetylated with acetic anhydride at a temperature of 10 to 30 ° C for a period of 5 to 300 minutes, the relative weight ratio of (4-O-methyl-ε-D-glucuron, The? -D-xylan, trifluoroacetic acid and acetic anhydrides are 1: 0.8 to 25: 0.7 to 25.
Výhodou O-acetyl-(4-O-metyl- οϋ -D-glukuróno,- -D-xylánu so stupňom substitúcie 0,1 až 1,5 acetylových skupin oproti doteráz známým O-acetyl derivátom hemicelulóz je, že sa dajú použiť ako substráty pre dalšiu modifikáciu, ako aj rozpustností vo vodě a vačšom množstve rozpúštíadiel a ich zmesi.An advantage of O-acetyl- (4-O-methyl- οϋ -D-glucuronium, -D-xylan with a degree of substitution of 0.1 to 1.5 acetyl groups over the prior art O-acetyl derivatives of hemicelluloses is that they can be used as substrates for further modification, as well as water solubility and more solvents and mixtures thereof.
Uvedené příklady demonstrujú, ale neobmedzujú predmet vynálezu.The examples given illustrate, but do not limit the scope of the invention.
Příklad 1 g (4-O-Metyl- -D-glukuróno)- /3 -D-xylánu z bukového dřeva sa rozpúšťa 2 hodiny pri teplote 20 *C v 27 g kyseliny trifluoroctovej za intenzívneho miešania. Potom sa přidá 7,7 g anhydridů kyseliny octovej a mieša sa počas 2 hodin. Reakcia sa zastaví přenesením reakčnej zmesi do dialyzačného čreva za súčasného zriedenia s vodou. Po oddialyCS 274022 Bl zování nízkomolekulárnych reakčných zložiek sa lyofilizáoiou získá 2,6 g vzduchosuchého produktu so stupňom substitúcie 1,3.EXAMPLE 1 1 g of (4-O-Methyl-D-glucurono) - [beta] -D-xylan from beechwood were dissolved in 27 g of trifluoroacetic acid under vigorous stirring at 20 DEG C. for 2 hours. Then 7.7 g of acetic anhydride are added and stirred for 2 hours. The reaction is stopped by transferring the reaction mixture to the dialysis gut while diluting with water. After separating the low molecular weight reactants, 2.6 g of an air-dry product with a degree of substitution of 1.3 are obtained by lyophilization.
Příklad 2Example 2
Postupuje sa ako v příklade 1 s tým rozdielom, že sa použije 0,7 g (4-O-metyl- oO. -D-glukuróno)- fa -D-xylánu z brezy a aktivuje sa s 17 g kyseliny trifluoroctovej po dobu 5 minút pri teplote 20 ‘c. Potom sa přidá 2,6 g anhydridu kyseliny octovej a acetyluje sa 15 minút pri teplote 20 *C. Získá sa 1,2 g O-acetyl-(4-O-metyl- cKz-D-glukuróno) - /3 -D-xylánu so stupňom substitúcie 0,5.The procedure is as in Example 1 except that 0.7 g of (4-O-methyl-o, -D-glucuron) -f-D-xylan from birch is used and activated with 17 g of trifluoroacetic acid for 5 hours. minutes at 20 ° C. 2.6 g of acetic anhydride are then added and acetylated for 15 minutes at 20 ° C. 1.2 g of O-acetyl- (4-O-methyl-cis-D-glucuron) -? - D-xylan with a degree of substitution of 0.5 are obtained.
Příklad 3Example 3
Postupuje sa ako v příklade 1 s tým rozdielom, že sa 1,4 g (4-O-metyl- «O-D-glukuróno)-/3 -D-xylánu z habru aktivuje v 28 g kyseliny trifluoroctovej pri teplote 10 *C, acetyluje 1,6 g anhydridu kyseliny octovej pri teplote 10 ’c počas 4 hodin. Získá sa 1,1 g O-acetyl- (4-O-metyl- -D-glukoróno) - /3 -D-xylánu so stupňom substitúcie 0,9.The procedure is as in Example 1 except that 1.4 g of (4-O-methyl-4-O-glucurono) - 3-D-xylan from hornbeam is activated in 28 g of trifluoroacetic acid at 10 ° C, acetylated 1.6 g of acetic anhydride at 10 DEG C. for 4 hours. 1.1 g of O-acetyl- (4-O-methyl-D-glucorono) -? - D-xylan with a degree of substitution of 0.9 are obtained.
Příklad 4Example 4
Postupuje sa ako v příklade 1 s tým rozdielom, že sa 1,1 g (4-O-metyl-<x> -D-glukuróno)- fa) -D-xylánu z topol'a, aktivuje 14,3 g kyseliny trifluoroctovej pri teplote 30 c po dobu 5 minút a acetyluje s 4,6 g anhydridu kyseliny octovej po dobu 15 minút pri teplo te 30 ’c. Po izolácii sa získá 1,5 g O-acetyl-(4-O-metyl-cK/ -D-glukuróno)- /3 -D-xylánu so stupňom substitúcie 1,4.The procedure is as in Example 1 except that 1.1 g of (4-O-methyl- [x] -D-glucuronol) -α-D-xylan from poplar is activated with 14.3 g of trifluoroacetic acid. at 30 ° C for 5 minutes and acetylated with 4.6 g acetic anhydride for 15 minutes at 30 ° C. After isolation, 1.5 g of O-acetyl- (4-O-methyl-cis-D-glucurono) - 3-D-xylan with a degree of substitution of 1.4 are obtained.
Přiklad 5Example 5
Postupuje sa ako v příklade 1 s tým rozdielom, že sa použije 1 g (4-0-metyl-oCz -D-glukuróno)- fa) -D-xylánu z dubu a aktivuje sa s 18 g kyseliny trifluoroctovej v priebehu 5 minút za miešania. K vzorke sa přidá 0,2 g anhydridu kyseliny octovej a acetyluje sa po dobu 15 minút. Po izolácii produktu ako v příklade 1 sa získá 0,9 g O-acetyl-(4-0-metyl- oR, -D-glukuróno)- -D-xylánu so stupňom substitúcie 0,5.The procedure is as in Example 1 except that 1 g (4-O-methyl-oC of -D-glucuron) -α) -D-xylan from oak is used and activated with 18 g of trifluoroacetic acid over 5 minutes with stirring. 0.2 g of acetic anhydride is added to the sample and acetylated for 15 minutes. After isolation of the product as in Example 1, 0.9 g of O-acetyl- (4-O-methyl-oR, -D-glucurono) -D-xylan with a degree of substitution of 0.5 is obtained.
O-Acetyl-(4-O-metyl- ofJ -D-glukuróno)- /3 ”D~xylán m3že nájsť široké použitie v chemickom priemysle ako filmotvorný materiál, medziprodukt v organickéj chémii, přísada do lakov, pomocných prostriedkov v textilnom priemysle a pracích prostriedkoch.O-Acetyl- (4-O-methyl-η-D-glucuron) - / 3'D-xylan can be used widely in the chemical industry as a film-forming material, an intermediate in organic chemistry, lacquer additive, textile aids and detergents.
PREDMET VYNÁLEZUOBJECT OF THE INVENTION
O-Acetyl-(4-O-metyl- 00 -D-glukuróno,- /3 -D-xylán na báze štrukturálnych jednotiek všeobecných vzorcov ^0O-Acetyl- (4-O-methyl- 00- D-glucuronium) - β-D-xylan based on structural units of formulas
Claims (5)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS760888A CS274022B1 (en) | 1988-11-21 | 1988-11-21 | 0-acetyl-(4-0-methyl-alpha-d-glucorono)-beta-d-xylan |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS760888A CS274022B1 (en) | 1988-11-21 | 1988-11-21 | 0-acetyl-(4-0-methyl-alpha-d-glucorono)-beta-d-xylan |
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| Publication Number | Publication Date |
|---|---|
| CS760888A1 CS760888A1 (en) | 1990-08-14 |
| CS274022B1 true CS274022B1 (en) | 1991-04-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS760888A CS274022B1 (en) | 1988-11-21 | 1988-11-21 | 0-acetyl-(4-0-methyl-alpha-d-glucorono)-beta-d-xylan |
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| Country | Link |
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| CS (1) | CS274022B1 (en) |
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1988
- 1988-11-21 CS CS760888A patent/CS274022B1/en unknown
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| Publication number | Publication date |
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| CS760888A1 (en) | 1990-08-14 |
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