CN106366216A - 一种双活性磺酸基蔗渣木聚糖磺柳酸酯的合成方法 - Google Patents
一种双活性磺酸基蔗渣木聚糖磺柳酸酯的合成方法 Download PDFInfo
- Publication number
- CN106366216A CN106366216A CN201610945262.4A CN201610945262A CN106366216A CN 106366216 A CN106366216 A CN 106366216A CN 201610945262 A CN201610945262 A CN 201610945262A CN 106366216 A CN106366216 A CN 106366216A
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- Prior art keywords
- bagasse xylan
- acid ester
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- acid
- xylan
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- 229920001221 xylan Polymers 0.000 title claims abstract description 79
- 241000609240 Ambelania acida Species 0.000 title claims abstract description 73
- 239000010905 bagasse Substances 0.000 title claims abstract description 73
- -1 xylan salicylsulfonic acid ester Chemical class 0.000 title claims abstract description 49
- 238000010189 synthetic method Methods 0.000 title claims abstract description 7
- 230000000694 effects Effects 0.000 title abstract description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 32
- 150000004823 xylans Chemical class 0.000 claims abstract description 30
- 239000012043 crude product Substances 0.000 claims abstract description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 7
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011734 sodium Substances 0.000 claims abstract description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims description 28
- 238000004458 analytical method Methods 0.000 claims description 23
- 239000002244 precipitate Substances 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
- 238000009835 boiling Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 238000013019 agitation Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000012423 maintenance Methods 0.000 claims description 3
- BCTWNMTZAXVEJL-UHFFFAOYSA-N phosphane;tungsten;tetracontahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W] BCTWNMTZAXVEJL-UHFFFAOYSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 abstract description 19
- 230000032050 esterification Effects 0.000 abstract description 17
- 238000000034 method Methods 0.000 abstract description 6
- 230000004071 biological effect Effects 0.000 abstract description 4
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 3
- 230000036436 anti-hiv Effects 0.000 abstract description 2
- 239000013078 crystal Substances 0.000 abstract description 2
- 230000001954 sterilising effect Effects 0.000 abstract description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000012374 esterification agent Substances 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000004659 sterilization and disinfection Methods 0.000 abstract 1
- 238000000967 suction filtration Methods 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 18
- 239000012086 standard solution Substances 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000019635 sulfation Effects 0.000 description 5
- 238000005670 sulfation reaction Methods 0.000 description 5
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- 150000004804 polysaccharides Chemical class 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 2
- 238000002479 acid--base titration Methods 0.000 description 2
- 238000007385 chemical modification Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 208000012826 adjustment disease Diseases 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Paper (AREA)
Abstract
Description
Claims (1)
Priority Applications (1)
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CN201610945262.4A CN106366216B (zh) | 2016-10-26 | 2016-10-26 | 一种双活性磺酸基蔗渣木聚糖磺柳酸酯的合成方法 |
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CN201610945262.4A CN106366216B (zh) | 2016-10-26 | 2016-10-26 | 一种双活性磺酸基蔗渣木聚糖磺柳酸酯的合成方法 |
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CN106366216A true CN106366216A (zh) | 2017-02-01 |
CN106366216B CN106366216B (zh) | 2019-11-26 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2019128410A1 (zh) * | 2017-12-26 | 2019-07-04 | 中国药科大学 | 木聚糖酯化产物在制备预防或治疗炎症性疾病及癌症药物中的应用 |
Citations (5)
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CN101942041A (zh) * | 2010-09-16 | 2011-01-12 | 桂林理工大学 | 一种硫酸酯化蔗渣木聚糖的制备方法 |
CN102875698A (zh) * | 2012-10-30 | 2013-01-16 | 桂林理工大学 | 氨基三磺酸钠水相酯化法合成蔗渣木聚糖硫酸酯的方法 |
CN104610469A (zh) * | 2015-03-08 | 2015-05-13 | 桂林理工大学 | 抗金黄色葡萄球菌双活性没食子酸-硫酸酯化蔗渣木聚糖的合成方法 |
CN104628882A (zh) * | 2015-03-08 | 2015-05-20 | 桂林理工大学 | 一种磺酸基蔗渣木聚糖邻苯二甲酸酯的合成方法 |
CN105777943A (zh) * | 2016-04-14 | 2016-07-20 | 南京工业大学 | 一种利用微通道反应装置制备木聚糖硫酸酯的方法 |
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2016
- 2016-10-26 CN CN201610945262.4A patent/CN106366216B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101942041A (zh) * | 2010-09-16 | 2011-01-12 | 桂林理工大学 | 一种硫酸酯化蔗渣木聚糖的制备方法 |
CN102875698A (zh) * | 2012-10-30 | 2013-01-16 | 桂林理工大学 | 氨基三磺酸钠水相酯化法合成蔗渣木聚糖硫酸酯的方法 |
CN104610469A (zh) * | 2015-03-08 | 2015-05-13 | 桂林理工大学 | 抗金黄色葡萄球菌双活性没食子酸-硫酸酯化蔗渣木聚糖的合成方法 |
CN104628882A (zh) * | 2015-03-08 | 2015-05-20 | 桂林理工大学 | 一种磺酸基蔗渣木聚糖邻苯二甲酸酯的合成方法 |
CN105777943A (zh) * | 2016-04-14 | 2016-07-20 | 南京工业大学 | 一种利用微通道反应装置制备木聚糖硫酸酯的方法 |
Non-Patent Citations (3)
Title |
---|
J.E. CASTANHEIRO等: ""Esterification of acetic acid by isoamylic alcohol over catalytic membranes of poly(vinyl alcohol) containing sulfonic acid groups"", 《APPLIED CATALYSIS》 * |
李和平等: ""双活性磺酸基蔗渣木聚糖邻苯二甲酸酯的合成与表征"", 《化学反应工程与工艺》 * |
李和平等: ""氨基三磺酸钠水相酯化法合成蔗渣木聚糖硫酸酯"", 《化学反应工程与工艺》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019128410A1 (zh) * | 2017-12-26 | 2019-07-04 | 中国药科大学 | 木聚糖酯化产物在制备预防或治疗炎症性疾病及癌症药物中的应用 |
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Application publication date: 20170201 Assignee: GUILIN XINYU GE INDUSTRY Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2023980044185 Denomination of invention: A Synthesis Method of Double Active Sulfonic Acid Bagasse Xylan Sulfonate Granted publication date: 20191126 License type: Common License Record date: 20231025 |
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Application publication date: 20170201 Assignee: Guangxi Kaitian agricultural new technology Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2023980045085 Denomination of invention: A Synthesis Method of Double Active Sulfonic Acid Bagasse Xylan Sulfonate Granted publication date: 20191126 License type: Common License Record date: 20231030 Application publication date: 20170201 Assignee: Guangxi conglomeration Energy Technology Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2023980045081 Denomination of invention: A Synthesis Method of Double Active Sulfonic Acid Bagasse Xylan Sulfonate Granted publication date: 20191126 License type: Common License Record date: 20231030 |