KR101172615B1 - Methods for distilling and manufacturing anhydrosugar alcohols - Google Patents
Methods for distilling and manufacturing anhydrosugar alcohols Download PDFInfo
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- KR101172615B1 KR101172615B1 KR1020100128251A KR20100128251A KR101172615B1 KR 101172615 B1 KR101172615 B1 KR 101172615B1 KR 1020100128251 A KR1020100128251 A KR 1020100128251A KR 20100128251 A KR20100128251 A KR 20100128251A KR 101172615 B1 KR101172615 B1 KR 101172615B1
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- alcohol
- sugar
- anhydrosugar
- alcohols
- distillation
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 150000001298 alcohols Chemical class 0.000 title claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000004821 distillation Methods 0.000 claims abstract description 47
- 150000005846 sugar alcohols Chemical class 0.000 claims abstract description 30
- 235000000346 sugar Nutrition 0.000 claims abstract description 21
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 15
- 150000002016 disaccharides Chemical class 0.000 claims abstract description 14
- 239000011259 mixed solution Substances 0.000 claims abstract description 14
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 14
- 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 claims description 23
- 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 claims description 23
- 239000000600 sorbitol Substances 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 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 12
- 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 claims description 11
- 229930195725 Mannitol Natural products 0.000 claims description 11
- 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 claims description 11
- 239000000594 mannitol Substances 0.000 claims description 11
- 235000010355 mannitol Nutrition 0.000 claims description 11
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 claims description 10
- 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 claims description 10
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 10
- 229930006000 Sucrose Natural products 0.000 claims description 10
- 239000008103 glucose Substances 0.000 claims description 10
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims description 10
- -1 aribinose Chemical compound 0.000 claims description 9
- 239000005720 sucrose Substances 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- KLDXJTOLSGUMSJ-UNTFVMJOSA-N (3s,3ar,6s,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-UNTFVMJOSA-N 0.000 claims description 6
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 6
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 6
- 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 claims description 6
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 6
- 229930091371 Fructose Natural products 0.000 claims description 6
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 6
- 239000005715 Fructose Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 6
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 6
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 6
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 6
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 229930182830 galactose Natural products 0.000 claims description 6
- 239000008101 lactose Substances 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 4
- 229960002479 isosorbide Drugs 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- KLDXJTOLSGUMSJ-UHFFFAOYSA-N 2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound OC1COC2C(O)COC21 KLDXJTOLSGUMSJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
- 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 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 229960002920 sorbitol Drugs 0.000 description 20
- 229960001031 glucose Drugs 0.000 description 9
- 239000000843 powder Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 235000016127 added sugars Nutrition 0.000 description 1
- OXQKEKGBFMQTML-UHFFFAOYSA-N alpha-Glucoheptitol Chemical compound OCC(O)C(O)C(O)C(O)C(O)CO OXQKEKGBFMQTML-UHFFFAOYSA-N 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
무수당 알코올의 증류 방법 및 이를 이용한 무수당 알코올의 제조 방법이 제공된다. 상기 증류 방법은, 무수당 알코올을 포함하는 혼합 용액에 당류를 첨가하여 증류하는 단계를 포함하고, 상기 제조 방법은, 당 알코올을 탈수반응시켜 무수당 알코올을 형성하는 단계 및 상기 무수당 알코올을 포함하는 혼합 용액에 당류를 첨가하여 증류하는 단계를 포함한다. 상기 당류는 단당류, 이당류, 및 당 알코올 중에서 선택된 하나 이상을 포함할 수 있다. A distillation method of anhydrosugar alcohol and a method of producing anhydrosugar alcohol using the same are provided. The distillation method includes the step of distilling by adding a saccharide to the mixed solution containing anhydrosugar alcohol, the production method includes the step of dehydrating the sugar alcohol to form anhydrosugar alcohol and the anhydrosugar alcohol And distilling by adding sugar to the mixed solution. The sugar may include one or more selected from monosaccharides, disaccharides, and sugar alcohols.
Description
본 발명은 무수당 알코올의 증류 및 제조 방법에 관한 것으로, 더욱 상세하게는 무수당 알코올의 증류에 당류를 이용하는 무수당 알코올의 증류 방법과 이를 이용한 무수당 알코올의 제조 방법에 관한 것이다.
The present invention relates to a method for distilling and preparing anhydrosugar alcohols, and more particularly, to a method for distilling anhydrosugar alcohols using saccharides for distillation of anhydrosugar alcohols and a method for producing anhydrosugar alcohols using the same.
당 알코올은 당류가 갖는 환원성 말단기에 수소를 부가하여 얻어지는 화합물로서, 탄소수에 따라 테트리톨, 펜티톨, 헥시톨 및 헵티톨로 분류될 수 있다. 그 중에서 탄소수가 6개인 헥시톨에는 소르비톨, 만니톨, 이디톨 등이 속하며 소르비톨과 만니톨은 특히 효용성이 큰 물질이다.The sugar alcohol is a compound obtained by adding hydrogen to the reducing end group of the sugar, and may be classified into tetratriol, pentitol, hexitol and heptitol according to carbon number. Among them, hexitol having 6 carbon atoms belongs to sorbitol, mannitol, iditol, and the like, and sorbitol and mannitol are particularly useful substances.
전분에서 유래한 무수당 알코올은 분자 내 하이드록시기가 두 개인 디올(diol) 형태로 상기 당 알코올로부터 제조될 수 있다. 상기 무수당 알코올은 재생 가능한 천연자원으로부터 유래한 친환경 자원이라는 점에서 오래전부터 많은 관심과 함께 제조 방법에 관한 연구가 진행되어 오고 있다.Anhydrosugar alcohols derived from starch may be prepared from the sugar alcohol in the form of diols having two hydroxyl groups in the molecule. Since the anhydrosugar alcohol is an environmentally friendly resource derived from renewable natural resources, research on the manufacturing method has been conducted with a lot of interest for a long time.
상기 무수당 알코올은 심장 및 혈관 질환 치료, 패치의 접착제, 구강 청정제 등의 약제로 유용하고 화장품 산업에서 조성물의 용매, 식품산업에서 유화제 등으로 사용될 수 있다. 또, 폴리에스테르 고분자와 같은 플라스틱산업에서 매우 유용하며, 폴리에스테르, 폴리에틸렌 테레프탈레이트, 폴리카보네이트, 폴리우레탄 등의 유리전이온도를 올릴 수 있고 강도 개선효과가 있어 생분해성 친환경소재로 활용 가치가 높다. 또, 접착제, 친환경 가소제, 생분해성 고분자, 수용성 락카의 친환경 용매로도 사용될 수 있는 것으로 알려져 있다.The anhydrosugar alcohol is useful as a medicament for treating heart and vascular diseases, adhesives for patches, mouthwashes and the like, and may be used as a solvent for compositions in the cosmetic industry, as an emulsifier in the food industry, and the like. In addition, it is very useful in the plastics industry, such as polyester polymer, and can increase the glass transition temperature of polyester, polyethylene terephthalate, polycarbonate, polyurethane, etc., and has high strength, which is highly useful as a biodegradable eco-friendly material. In addition, it is known that it can also be used as an environmentally friendly solvent of adhesives, eco-friendly plasticizers, biodegradable polymers, water-soluble lacquer.
이와 같이, 무수당 알코올을 산업적으로 다양하게 활용할 수 있지만, 종래 방법으로 무수당 알코올을 제조하면 증류 수율 등이 낮은 문제점이 있어 아직 그 이용이 미흡하다.
As described above, the anhydrosugar alcohol can be used in various industrially. However, when the anhydrosugar alcohol is prepared by the conventional method, there is a problem in that the distillation yield is low and the use thereof is still insufficient.
상기와 같은 문제점을 해결하기 위하여, 본 발명은 증류 수율이 높은 무수당 알코올의 증류 방법을 제공한다.In order to solve the above problems, the present invention provides a distillation method of the anhydrosugar alcohol having a high distillation yield.
본 발명은 상기 증류 방법을 이용한 무수당 알코올의 제조 방법을 제공한다.The present invention provides a method for producing anhydrosugar alcohols using the distillation method.
본 발명의 실시예들에 따른 무수당 알코올의 증류 방법은, 무수당 알코올을 포함하는 혼합 용액에 당류를 첨가하여 증류하는 단계를 포함한다.Distillation method of the anhydrosugar alcohol according to embodiments of the present invention, the distillation by adding a sugar to the mixed solution containing anhydrosugar alcohol.
상기 당류는 단당류, 이당류, 및 당 알코올 중에서 선택된 하나 이상을 포함할 수 있다. 상기 단당류는 글루코오스, 프룩토스, 만노스, 갈락토스, 리보스, 아리비노스, 및 자일로스 중에서 선택된 하나 이상을 포함할 수 있고, 상기 이당류는 수크로스, 말토스, 및 락토스 중에서 선택된 하나 이상을 포함할 수 있으며, 상기 당 알코올은 소르비톨, 만니톨, 및 이디톨 중에서 선택된 하나 이상을 포함할 수 있다.
The sugar may include one or more selected from monosaccharides, disaccharides, and sugar alcohols. The monosaccharide may include one or more selected from glucose, fructose, mannose, galactose, ribose, aribinose, and xylose, and the disaccharide may include one or more selected from sucrose, maltose, and lactose. The sugar alcohol may include at least one selected from sorbitol, mannitol, and iditol.
본 발명의 실시예들에 따른 무수당 알코올의 제조 방법은, 당 알코올을 탈수반응시켜 무수당 알코올을 형성하는 단계 및 상기 무수당 알코올을 포함하는 혼합 용액에 당류를 첨가하여 증류하는 단계를 포함한다.The method for preparing anhydrosugar alcohols according to embodiments of the present invention includes dehydrating a sugar alcohol to form anhydrosugar alcohol and distilling by adding sugar to a mixed solution including the anhydrosugar alcohol. .
상기 당 알코올은 헥시톨을 포함할 수 있다. 상기 헥시톨은 소르비톨, 만니톨, 이디톨, 및 갈락티톨 중에서 선택된 하나 이상을 포함할 수 있다.The sugar alcohol may include hexitol. The hexitol may include one or more selected from sorbitol, mannitol, iditol, and galactitol.
상기 당류는 단당류, 이당류, 및 당 알코올 중에서 선택된 하나 이상을 포함할 수 있다. 상기 단당류는 글루코오스, 프룩토스, 만노스, 갈락토스, 리보스, 아리비노스, 및 자일로스 중에서 선택된 하나 이상을 포함할 수 있다. 상기 이당류는 수크로스, 말토스, 및 락토스 중에서 선택된 하나 이상을 포함할 수 있다. 상기 당 알코올은 소르비톨, 만니톨, 및 이디톨 중에서 선택된 하나 이상을 포함할 수 있다.The sugar may include one or more selected from monosaccharides, disaccharides, and sugar alcohols. The monosaccharide may include one or more selected from glucose, fructose, mannose, galactose, ribose, aribinose, and xylose. The disaccharide may comprise one or more selected from sucrose, maltose, and lactose. The sugar alcohol may include one or more selected from sorbitol, mannitol, and iditol.
상기 무수당 알코올은 이소소르비드(1,4-3,6-디안히드로소르비톨), 이소만니드(1,4-3,6-디안히드로만니톨), 또는 이소이디드(1,4-3,6-디안히드로이디톨)일 수 있다.The anhydrosugar alcohol is isosorbide (1,4-3,6- dianhydrosorbitol), isomannide (1,4-3,6- dianhydromannitol), or isoidide (1,4-3,6 Dianhydroiditol).
상기 탈수반응은 산 촉매에 의해 진행될 수 있다. 상기 산 촉매는, 황산, 염산, 및 인산 중에서 선택된 단일 산이거나, 황산과, p-톨루엔 설폰산, 메탄 설폰산, 에탄 설폰산, 벤젠 설폰산, 나프탈렌 설폰산, 및 황산 알루미늄 중에서 선택된 하나 이상을 포함하는 혼합 산일 수 있다.The dehydration may be carried out by an acid catalyst. The acid catalyst is a single acid selected from sulfuric acid, hydrochloric acid, and phosphoric acid, or at least one selected from sulfuric acid, p-toluene sulfonic acid, methane sulfonic acid, ethane sulfonic acid, benzene sulfonic acid, naphthalene sulfonic acid, and aluminum sulfate. It may be a mixed acid containing.
상기 당류는 상기 당 알코올 100중량부에 대하여 1 ~ 20중량부로 첨가될 수 있다.The sugar may be added in an amount of 1 to 20 parts by weight based on 100 parts by weight of the sugar alcohol.
상기 증류는 150 ~ 250℃의 온도에서 진공 하에 수행될 수 있다.The distillation may be performed under vacuum at a temperature of 150 ~ 250 ℃.
상기 무수당 알코올의 제조 방법은, 상기 증류를 수행하기 전에, 상기 혼합 용액에 알칼리를 첨가하여 중화하는 단계를 더 포함할 수 있다.The method for preparing the anhydrosugar alcohol may further include neutralizing by adding an alkali to the mixed solution before performing the distillation.
상기 무수당 알코올의 제조 방법은, 상기 증류에 의해 얻어진 증류액을 탈색하기 위해 활성탄 처리, 활성백토 처리 및 이온정제 처리 중에서 하나 이상을 수행하는 단계를 더 포함할 수 있다.
The method for preparing anhydrosugar alcohol may further include performing one or more of activated carbon treatment, activated clay treatment and ion purification treatment to decolorize the distillate obtained by the distillation.
본 발명의 실시예들에 따르면, 무수당 알코올의 증류에 당류를 사용하여 증류 효율이 향상될 수 있다. 설비나 공정의 추가없이 증류 수율이 향상될 수 있다. 또 무수당 알코올의 유동성이 현저하게 개선되어 공정이 용이하고 진행될 수 있고, 증류 수율이 향상될 수 있다. 본 발명의 실시예들에 따른 제조 방법에서 사용되는 당류는 바이오매스로서 친환경 녹색산업의 주요 원료인 친환경 물질이며, 전분 등의 활용범위를 확대할 수 있어서 산업적으로 매우 유용하다.
According to embodiments of the present invention, distillation efficiency may be improved by using saccharides for distillation of anhydrosugar alcohol. Distillation yield can be improved without the addition of equipment or processes. In addition, the fluidity of the anhydrosugar alcohol is remarkably improved, so that the process can be easily carried out and the distillation yield can be improved. Sugars used in the manufacturing method according to the embodiments of the present invention is a biomass is an environmentally friendly material that is the main raw material of the eco-friendly green industry, it is very useful industrially to expand the range of application of starch.
이하, 실시예들을 통하여 본 발명을 보다 상세하게 설명한다. 본 발명의 목적, 특징, 장점은 이하의 실시예들을 통해 쉽게 이해될 것이다. 본 발명은 여기서 설명되는 실시예들에 한정되지 않고, 다른 형태로 구체화될 수도 있다. 여기서 소개되는 실시예들은 개시된 내용이 철저하고 완전해질 수 있도록 그리고 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자에게 본 발명의 사상이 충분히 전달될 수 있도록 하기 위해 제공되는 것이다. 따라서, 이하의 실시예들에 의하여 본 발명이 제한되어서는 안 된다.Hereinafter, the present invention will be described in more detail with reference to the following examples. The objects, features and advantages of the present invention will be easily understood by the following embodiments. The present invention is not limited to the embodiments described herein, but may be embodied in other forms. The embodiments disclosed herein are provided so that the disclosure may be thorough and complete, and that those skilled in the art will be able to convey the spirit of the invention to those skilled in the art. Therefore, the present invention should not be limited by the following examples.
본 명세서에서, 무수당 알코올은 당 알코올의 내부 구조에서 하나 이상의 물 분자를 제거하여 얻은 물질을 의미할 수 있다.
In the present specification, the anhydrosugar alcohol may refer to a material obtained by removing one or more water molecules from the internal structure of the sugar alcohol.
본 발명의 실시예들에 따른 무수당 알코올의 증류 방법은, 무수당 알코올을 포함하는 혼합 용액에 당류를 첨가하여 증류하는 단계를 포함할 수 있다. Distillation method of the anhydrosugar alcohol according to embodiments of the present invention, may include the step of distilling by adding a sugar to the mixed solution containing anhydrosugar alcohol.
상기 당류는 단당류, 이당류, 및 당 알코올 중에서 선택된 하나 이상을 포함할 수 있다. 상기 단당류는 글루코오스, 프룩토스, 만노스, 갈락토스, 리보스, 아리비노스, 및 자일로스 중에서 선택된 하나 이상을 포함할 수 있고, 상기 이당류는 수크로스, 말토스, 및 락토스 중에서 선택된 하나 이상을 포함할 수 있으며, 상기 당 알코올은 소르비톨, 만니톨, 및 이디톨 중에서 선택된 하나 이상을 포함할 수 있다.The sugar may include one or more selected from monosaccharides, disaccharides, and sugar alcohols. The monosaccharide may include one or more selected from glucose, fructose, mannose, galactose, ribose, aribinose, and xylose, and the disaccharide may include one or more selected from sucrose, maltose, and lactose. The sugar alcohol may include at least one selected from sorbitol, mannitol, and iditol.
상기와 같이, 무수당 알코올을 포함하는 혼합 용액에 당류를 첨가하여 증류함으로써 증류 수율이 증가될 수 있다.
As described above, the distillation yield may be increased by distillation by adding saccharide to the mixed solution containing anhydrosugar alcohol.
본 발명의 실시예들에 따른 무수당 알코올의 제조 방법은, 상기 무수당 알코올의 증류 방법을 이용한 것으로서, 당 알코올을 탈수반응시켜 무수당 알코올을 형성하는 단계 및 상기 무수당 알코올을 포함하는 혼합 용액에 당류를 첨가하여 증류하는 단계를 포함할 수 있다.The method for preparing anhydrosugar alcohol according to embodiments of the present invention, using the distillation method of the anhydrosugar alcohol, dehydrating the sugar alcohol to form anhydrosugar alcohol and a mixed solution containing the anhydrosugar alcohol It may comprise the step of distilling by adding sugar to.
상기 당 알코올은 헥시톨을 포함할 수 있다. 상기 헥시톨은 소르비톨, 만니톨, 이디톨, 및 갈락티톨 중에서 선택된 하나 이상을 포함할 수 있다.The sugar alcohol may include hexitol. The hexitol may include one or more selected from sorbitol, mannitol, iditol, and galactitol.
상기 당류는 단당류, 이당류, 및 당 알코올 중에서 선택된 하나 이상을 포함할 수 있고, 상기 무수당 알코올의 증류 효율을 향상시킬 수 있다. 상기 단당류는 글루코오스, 프룩토스, 만노스, 갈락토스 등의 육탄당과, 리보스, 아리비노스, 자일로스 등의 오탄당 중에서 선택된 하나 이상을 포함할 수 있다. 상기 이당류는 수크로스, 말토스, 및 락토스 중에서 선택된 하나 이상을 포함할 수 있다. 상기 당 알코올은 소르비톨, 만니톨, 및 이디톨 중에서 선택된 하나 이상을 포함할 수 있다.The sugar may include one or more selected from monosaccharides, disaccharides, and sugar alcohols, and may improve the distillation efficiency of the anhydrosugar alcohol. The monosaccharide may include one or more selected from hexasaccharides such as glucose, fructose, mannose, and galactose, and pentose sugars such as ribose, aribinose, and xylose. The disaccharide may comprise one or more selected from sucrose, maltose, and lactose. The sugar alcohol may include one or more selected from sorbitol, mannitol, and iditol.
상기 당류로 전분에서 유래하는 글루코오스, 사탕수수에서 유래하는 수크로스, 또는 글루코오스에 수첨 반응을 통해 쉽게 제조될 수 있는 소르비톨을 사용하는 것이 바람직하다.As the saccharide, it is preferable to use glucose derived from starch, sucrose derived from sugar cane, or sorbitol which can be easily prepared through a hydrogenation reaction to glucose.
상기 무수당 알코올은 이소소르비드(1,4-3,6-디안히드로소르비톨), 이소만니드(1,4-3,6-디안히드로만니톨), 또는 이소이디드(1,4-3,6-디안히드로이디톨)일 수 있다.The anhydrosugar alcohol is isosorbide (1,4-3,6- dianhydrosorbitol), isomannide (1,4-3,6- dianhydromannitol), or isoidide (1,4-3,6 Dianhydroiditol).
상기 탈수반응은 산 촉매에 의해 진행될 수 있다. 상기 산 촉매는, 황산, 염산, 및 인산 중에서 선택된 단일 산이거나, 황산과, p-톨루엔 설폰산, 메탄 설폰산, 에탄 설폰산, 벤젠 설폰산, 나프탈렌 설폰산, 및 황산 알루미늄 중에서 선택된 하나 이상을 포함하는 혼합 산일 수 있다.The dehydration may be carried out by an acid catalyst. The acid catalyst is a single acid selected from sulfuric acid, hydrochloric acid, and phosphoric acid, or at least one selected from sulfuric acid, p-toluene sulfonic acid, methane sulfonic acid, ethane sulfonic acid, benzene sulfonic acid, naphthalene sulfonic acid, and aluminum sulfate. It may be a mixed acid containing.
상기 당류는 상기 당 알코올 100중량부에 대하여 1 ~ 20중량부로 첨가될 수 있다. 상기 당류의 첨가량이 1 중량부 미만이면 유동성이 크게 개선되지 않아 증류 효율의 향상이 크지 않을 수 있고, 20 중량부 초과이면 증류 효율이 크게 향상되지 않고 당류 첨가량 증가에 따른 경제성이 저하될 수 있다. The sugar may be added in an amount of 1 to 20 parts by weight based on 100 parts by weight of the sugar alcohol. If the amount of the saccharide added is less than 1 part by weight, the fluidity may not be greatly improved, and thus, the distillation efficiency may not be greatly improved. If the amount of the saccharide is added more than 20 parts by weight, the distillation efficiency may not be greatly improved, and the economic efficiency may be reduced due to the increase in the amount of the added sugar.
상기 증류는 150 ~ 250℃의 온도와 5mmHg 이하의 진공 조건에서 수행될 수 있다. 상기 증류 온도가 150℃ 미만이면 높은 순도의 무수당 알코올이 얻어질 수 있으나 무수당 알코올의 증류가 잘 이루어지지 않을 수 있고, 250℃ 초과이면 탄화되거나 고분자 물질이 생성될 수 있고, 발색 물질이 형성되어 색상이 진해지면 탈색이 어려워질 수 있다. 상기 증류는 일반적인 증류기, 예를 들어 박막 증류기 등을 사용하여 수행될 수 있다.The distillation may be carried out at a temperature of 150 ~ 250 ℃ and vacuum conditions of 5mmHg or less. If the distillation temperature is less than 150 ℃ high purity anhydrosugar alcohol may be obtained but distillation of the anhydrosugar alcohol may not be made well, if it is above 250 ℃ carbonized or a polymer material may be formed, the coloring material is formed If the color becomes darker, it may be difficult to discolor. The distillation can be carried out using a common still, for example a thin film still.
상기 증류를 수행하기 전에, 상기 혼합 용액에 알칼리를 첨가하여 중화할 수 있다. 상기 증류에 의해 얻어진 증류액을 탈색하기 위해 활성탄 처리, 활성백토 처리 및 이온정제 처리 중에서 하나 이상을 수행할 수 있다.
Before carrying out the distillation, alkali may be added to the mixed solution to neutralize it. In order to decolorize the distillate obtained by the distillation, one or more of activated carbon treatment, activated clay treatment and ion purification treatment may be performed.
실시예Example 및 And 비교예Comparative example
실시예Example 1 One
당 알코올인 소르비톨 분말(D-소르비톨, ㈜삼양제넥스) 1,200g을 교반기가 부착된 4구 유리 반응기에 넣고 온도를 110℃로 승온하여 녹였다. 상기 반응기에 진한 황산(덕산화공, 95%) 12g과 메탄 설폰산(시그마, 70%) 7.2g을 각각 투입한 후에 반응 온도를 135℃로 승온하였다. 온도를 유지하며 4시간 동안 3mmHg의 진공 조건에서 탈수 반응을 진행하여 상기 소르비톨을 무수당 알코올인 이소소르비드로 전환시켰다. 상기 무수당 알코올로의 전환율은 89.5%이었다. 1,200 g of sorbitol powder (D-sorbitol, Samyang Genex Co., Ltd.), a sugar alcohol, was placed in a four-necked glass reactor equipped with a stirrer, and the temperature was raised to 110 ° C to dissolve. After adding 12 g of concentrated sulfuric acid (duk oxide, 95%) and 7.2 g of methane sulfonic acid (Sigma, 70%) to the reactor, the reaction temperature was raised to 135 ° C. The sorbitol was converted to anhydrosugar alcohol, isosorbide, by dehydration under vacuum at 3 mmHg for 4 hours while maintaining the temperature. The conversion to the anhydrosugar alcohol was 89.5%.
상기 반응기의 온도를 110℃로 낮춘 후에 상기 탈수 반응이 진행된 혼합 용액에 50% 수산화나트륨 용액(삼전순약)을 31.2g 첨가하여 중화시켰다. 중화가 완료된 상기 혼합 용액에 유동성 향상을 위한 당류로서 당 알코올인 소르비톨 분말 60g을 넣고 교반하여 용융시킨 후 온도를 220℃로 승온하면서 3mmHg의 진공 하에 증류시켰다. 이렇게 얻어진 증류액의 양을 측정하고 고성능 액체 크로마토분석기(HPLC, high performance liquid chromatography)로 무수당 알코올의 순도를 측정하였다. 무수당 알코올의 증류 수율은 68.0%이었고, 순도는 96.2%이었다.
After the temperature of the reactor was lowered to 110 ° C., 31.2 g of 50% sodium hydroxide solution (Samjeon Pure Chemical Co., Ltd.) was neutralized by adding the mixed solution in which the dehydration reaction proceeded. 60 g of sorbitol powder, a sugar alcohol, was added to the mixed solution of neutralization as a saccharide for improving fluidity, stirred and melted, and then distilled under vacuum of 3 mmHg while raising the temperature to 220 ° C. The amount of the distillate thus obtained was measured and the purity of the anhydrosugar alcohol was measured by high performance liquid chromatography (HPLC). The distillation yield of the anhydrosugar alcohol was 68.0%, and the purity was 96.2%.
실시예Example 2 2
유동성 향상을 위한 당류로서 소르비톨 분말 120.0g을 사용한 것을 제외하고는 실시예 1과 동일하게 수행하였다. 무수당 알코올의 증류 수율은 69.6%이었고, 순도는 96.1%이었다.
The same procedure as in Example 1 was conducted except that 120.0 g of sorbitol powder was used as a saccharide for improving flowability. The distillation yield of the anhydrosugar alcohol was 69.6%, and the purity was 96.1%.
실시예Example 3 3
유동성 향상을 위한 당류로서 소르비톨 분말 180.0g을 사용한 것을 제외하고는 실시예 1과 동일하게 수행하였다. 무수당 알코올의 증류 수율은 70.7%이었고, 순도는 96.0%이었다.
The same procedure as in Example 1 was conducted except that 180.0 g of sorbitol powder was used as a saccharide for improving flowability. The distillation yield of the anhydrosugar alcohol was 70.7%, and the purity was 96.0%.
실시예 4 Example 4
유동성 향상을 위한 당류로서 소르비톨 분말 240.0g을 사용한 것을 제외하고는 실시예 1과 동일하게 수행하였다. 무수당 알코올의 증류 수율은 71.2%이었고, 순도는 96.0%이었다.
The same procedure as in Example 1 was carried out except that 240.0 g of sorbitol powder was used as a saccharide for improving flowability. The distillation yield of the anhydrosugar alcohol was 71.2%, and the purity was 96.0%.
실시예Example 5 5
유동성 향상을 위한 당류로서 단당류인 글루코오스 분말(무수결정포도당, ㈜삼양제넥스) 120.0g을 사용한 것을 제외하고는 실시예 1과 동일하게 수행하였다. 무수당 알코올의 증류 수율은 65.2%이었고, 순도는 95.9%이었다.
It was carried out in the same manner as in Example 1 except that 120.0 g of glucose powder (anhydrous glucose, Samyang Genex Co., Ltd.), a monosaccharide, was used as a saccharide for improving fluidity. The distillation yield of the anhydrosugar alcohol was 65.2%, and the purity was 95.9%.
실시예Example 6 6
유동성 향상을 위한 당류로서 이당류인 수크로스 분말(백설탕, ㈜삼양사) 120.0g을 사용한 것을 제외하고는 실시예 1과 동일하게 수행하였다. 무수당 알코올의 증류 수율은 64.6%이었고, 순도는 95.9%이었다.
The same procedure as in Example 1 was performed except that 120.0 g of a disaccharide, sucrose powder (white sugar, Samyang Co., Ltd.) was used as a sugar for improving fluidity. The distillation yield of the anhydrosugar alcohol was 64.6%, and the purity was 95.9%.
비교예Comparative example 1 One
유동성 향상을 위한 당류를 사용하지 않은 것을 제외하고는 실시예 1과 동일하게 수행하였다. 무수당 알코올의 증류 수율은 56.7%이었고, 순도는 96.2%이었다.
The same procedure as in Example 1 was carried out except that no saccharide for improving the fluidity was used. The distillation yield of the anhydrosugar alcohol was 56.7%, and the purity was 96.2%.
상기 실시예 1~5 및 비교예 1에서 제조된 무수당 알코올에서의 전환율 분석은 가스 크로마토분석기(GC, gas chromatography, HP5890)를 이용하여 실시하였고, 순도 분석은 고성능 액체 크로마토분석기(HPLC, high performance liquid chromatography, HP1100)를 이용하여 실시하였다. 측정된 무수당 알코올의 순도 및 증류 수율을 아래 표 1에 나타내었다.Conversion rate analysis in the anhydrosugar alcohols prepared in Examples 1 to 5 and Comparative Example 1 was carried out using a gas chromatography (GC, gas chromatography, HP5890), purity analysis was performed by high performance liquid chromatography (HPLC, high performance) liquid chromatography, HP1100). The purity and distillation yield of the anhydrosugar alcohols measured are shown in Table 1 below.
전환율(%): 생성된 무수당 알코올 몰수 / 투입된 헥시톨 몰수 x 100% Conversion: Number of moles of anhydrosugar alcohol produced / number of moles of hexitol added x 100
순도(%): 증류액 내 무수당 알코올 중량 / 증류액 중량 x 100Purity (%): weight of anhydrosugar alcohol in distillate / weight of distillate x 100
증류 수율(%): 증류액 내 무수당 알코올 몰수 / 투입된 헥시톨 몰수 x 100
Distillation yield (%): Number of moles of anhydrosugar alcohol in distillate / Number of moles of hexitol added x 100
(당 알코올 100중량부 기준)Added amount of sugar
(Based on 100 parts by weight of sugar alcohol)
상기 표 1에 나타난 바와 같이, 당 알코올이 탈수 반응에 의해 무수당 알코올로 전환된 후 유동성 향상을 위한 당류를 첨가하여 증류를 수행함으로써 증류 수율이 증가하는 것을 알 수 있다.
As shown in Table 1, it can be seen that the distillation yield is increased by the sugar alcohol is converted to anhydrosugar alcohol by the dehydration reaction, and then distillation is performed by adding sugars for improving fluidity.
이제까지 본 발명에 대한 구체적인 실시예들을 살펴보았다. 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자는 본 발명이 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 변형된 형태로 구현될 수 있음을 이해할 수 있을 것이다. 그러므로 개시된 실시예들은 한정적인 관점이 아니라 설명적인 관점에서 고려되어야 한다. 본 발명의 범위는 전술한 설명이 아니라 특허청구범위에 나타나 있으며, 그와 동등한 범위 내에 있는 모든 차이점은 본 발명에 포함된 것으로 해석되어야 할 것이다.
Hereinafter, specific embodiments of the present invention have been described. Those skilled in the art will appreciate that the present invention can be implemented in a modified form without departing from the essential features of the present invention. Therefore, the disclosed embodiments should be considered in an illustrative rather than a restrictive sense. The scope of the present invention is shown in the claims rather than the foregoing description, and all differences within the scope will be construed as being included in the present invention.
Claims (15)
상기 당류는 단당류, 이당류, 및 당 알코올 중에서 선택된 하나 이상을 포함하는 것을 특징으로 하는 무수당 알코올의 증류 방법.In claim 1,
The saccharide is a distillation method of anhydrosugar alcohols, characterized in that it comprises at least one selected from monosaccharides, disaccharides, and sugar alcohols.
상기 단당류는 글루코오스, 프룩토스, 만노스, 갈락토스, 리보스, 아리비노스, 및 자일로스 중에서 선택된 하나 이상을 포함하고,
상기 이당류는 수크로스, 말토스, 및 락토스 중에서 선택된 하나 이상을 포함하며,
상기 당 알코올은 소르비톨, 만니톨, 및 이디톨 중에서 선택된 하나 이상을 포함하는 것을 특징으로 하는 무수당 알코올의 증류 방법.In claim 2,
The monosaccharide comprises one or more selected from glucose, fructose, mannose, galactose, ribose, aribinose, and xylose,
The disaccharide comprises one or more selected from sucrose, maltose, and lactose,
The sugar alcohol distillation method of the anhydrosugar alcohol, characterized in that it comprises at least one selected from sorbitol, mannitol, and iditol.
상기 무수당 알코올을 포함하는 혼합 용액에 당류를 첨가하여 증류하는 단계를 포함하는 무수당 알코올의 제조 방법.Dehydrating the sugar alcohol to form anhydrosugar alcohol; And
Method for producing anhydrosugar alcohol comprising the step of distilling by adding a saccharide to the mixed solution containing the anhydrosugar alcohol.
상기 당 알코올은 헥시톨을 포함하는 것을 특징으로 하는 무수당 알코올의 제조 방법.In claim 4,
The sugar alcohol is a method for producing anhydrosugar alcohols, characterized in that it comprises hexitol.
상기 헥시톨은 소르비톨, 만니톨, 이디톨, 및 갈락티톨 중에서 선택된 하나 이상을 포함하는 것을 특징으로 하는 무수당 알코올의 제조 방법.In claim 5,
The hexitol is a method for producing anhydrosugar alcohols, characterized in that it comprises at least one selected from sorbitol, mannitol, iditol, and galactitol.
상기 당류는 단당류, 이당류, 및 당 알코올 중에서 선택된 하나 이상을 포함하는 것을 특징으로 하는 무수당 알코올의 제조 방법.In claim 4,
The sugar is a method of producing anhydrosugar alcohols, characterized in that it comprises one or more selected from monosaccharides, disaccharides, and sugar alcohols.
상기 단당류는 글루코오스, 프룩토스, 만노스, 갈락토스, 리보스, 아리비노스, 및 자일로스 중에서 선택된 하나 이상을 포함하고,
상기 이당류는 수크로스, 말토스, 및 락토스 중에서 선택된 하나 이상을 포함하며,
상기 당 알코올은 소르비톨, 만니톨, 및 이디톨 중에서 선택된 하나 이상을 포함하는 것을 특징으로 하는 무수당 알코올의 제조 방법.In claim 7,
The monosaccharide comprises one or more selected from glucose, fructose, mannose, galactose, ribose, aribinose, and xylose,
The disaccharide comprises one or more selected from sucrose, maltose, and lactose,
The sugar alcohol is a method for producing anhydrosugar alcohols, characterized in that it comprises at least one selected from sorbitol, mannitol, and iditol.
상기 무수당 알코올은 이소소르비드(1,4-3,6-디안히드로소르비톨), 이소만니드(1,4-3,6-디안히드로만니톨), 또는 이소이디드(1,4-3,6-디안히드로이디톨)인 것을 특징으로 하는 무수당 알코올의 제조 방법.In claim 4,
The anhydrosugar alcohol is isosorbide (1,4-3,6- dianhydrosorbitol), isomannide (1,4-3,6- dianhydromannitol), or isoidide (1,4-3,6 -Dianhydroiditol). The process for producing anhydrosugar alcohols.
상기 탈수반응은 산 촉매에 의해 진행되는 것을 특징으로 하는 무수당 알코올의 제조 방법.In claim 4,
The dehydration reaction is a process for producing anhydrosugar alcohols, characterized in that the acid catalyst.
상기 산 촉매는,
황산, 염산, 및 인산 중에서 선택된 단일 산이거나,
황산과, p-톨루엔 설폰산, 메탄 설폰산, 에탄 설폰산, 벤젠 설폰산, 나프탈렌 설폰산, 및 황산 알루미늄 중에서 선택된 하나 이상을 포함하는 혼합 산인 것을 특징으로 하는 무수당 알코올의 제조 방법.In claim 10,
The acid catalyst,
Is a single acid selected from sulfuric acid, hydrochloric acid, and phosphoric acid,
A sulfuric acid and a mixed acid comprising at least one selected from p-toluene sulfonic acid, methane sulfonic acid, ethane sulfonic acid, benzene sulfonic acid, naphthalene sulfonic acid, and aluminum sulfate.
상기 당류는 상기 당 알코올 100중량부에 대하여 1 ~ 20중량부로 첨가되는 것을 특징으로 하는 무수당 알코올의 제조 방법.In claim 4,
The sugar is a method for producing anhydrosugar alcohols, characterized in that added to 1 to 20 parts by weight based on 100 parts by weight of the sugar alcohol.
상기 증류는 150 ~ 250℃의 온도에서 진공 하에 수행되는 것을 특징으로 하는 무수당 알코올의 제조 방법.In claim 4,
The distillation is a method for producing anhydrosugar alcohols, characterized in that carried out under vacuum at a temperature of 150 ~ 250 ℃.
상기 증류를 수행하기 전에, 상기 혼합 용액에 알칼리를 첨가하여 중화하는 단계를 더 포함하는 무수당 알코올의 제조 방법.In claim 4,
Before performing the distillation, the method of producing anhydrosugar alcohol further comprising the step of neutralizing by adding alkali to the mixed solution.
상기 증류에 의해 얻어진 증류액을 탈색하기 위해 활성탄 처리, 활성백토 처리 및 이온정제 처리 중에서 하나 이상을 수행하는 단계를 더 포함하는 무수당 알코올의 제조 방법.
In claim 4,
The method for producing anhydrosugar alcohol further comprising the step of performing at least one of activated carbon treatment, activated clay treatment and ion purification treatment to decolorize the distillate obtained by the distillation.
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| KR20120066904A (en) | 2012-06-25 |
| WO2012081785A1 (en) | 2012-06-21 |
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