JPH04295491A - Production of alkylglycoside - Google Patents
Production of alkylglycosideInfo
- Publication number
- JPH04295491A JPH04295491A JP3058597A JP5859791A JPH04295491A JP H04295491 A JPH04295491 A JP H04295491A JP 3058597 A JP3058597 A JP 3058597A JP 5859791 A JP5859791 A JP 5859791A JP H04295491 A JPH04295491 A JP H04295491A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- sugar
- higher alcohol
- aging
- unreacted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 235000000346 sugar Nutrition 0.000 claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000010409 thin film Substances 0.000 claims abstract description 11
- 239000003377 acid catalyst Substances 0.000 claims abstract description 10
- 229930182470 glycoside Natural products 0.000 claims description 27
- -1 alkyl glycoside Chemical class 0.000 claims description 25
- 230000005070 ripening Effects 0.000 claims description 6
- 150000002338 glycosides Chemical class 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims 1
- 230000032683 aging Effects 0.000 abstract description 12
- 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 abstract description 7
- 239000007795 chemical reaction product Substances 0.000 abstract description 7
- 239000008103 glucose Substances 0.000 abstract description 7
- 239000011552 falling film Substances 0.000 abstract description 3
- 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 3
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 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 7
- 229960001031 glucose Drugs 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 6
- JDRSMPFHFNXQRB-CMTNHCDUSA-N Decyl beta-D-threo-hexopyranoside Chemical compound CCCCCCCCCCO[C@@H]1O[C@H](CO)C(O)[C@H](O)C1O JDRSMPFHFNXQRB-CMTNHCDUSA-N 0.000 description 5
- 229940073499 decyl glucoside Drugs 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 150000008163 sugars Chemical class 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002772 monosaccharides Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 150000004804 polysaccharides Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WQZGKKKJIJFFOK-CBPJZXOFSA-N D-Gulose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-CBPJZXOFSA-N 0.000 description 1
- WQZGKKKJIJFFOK-WHZQZERISA-N D-aldose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-WHZQZERISA-N 0.000 description 1
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 description 1
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 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
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- WQZGKKKJIJFFOK-VSOAQEOCSA-N L-altropyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-VSOAQEOCSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 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 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 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
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 125000000129 anionic group Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution 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
- 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 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000002663 humin Substances 0.000 description 1
- 125000002887 hydroxy group Chemical class [H]O* 0.000 description 1
- 150000002453 idose derivatives Chemical class 0.000 description 1
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 1
- 229940029339 inulin Drugs 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside 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]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明はアルキルグリコシドの製
造方法に関し、詳しくは色相が良好なアルキルグリコシ
ドの製造方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing alkyl glycosides, and more particularly to a method for producing alkyl glycosides with good hue.
【０００２】0002
【従来の技術及び発明が解決しようとする課題】糖誘導
体界面活性剤であるアルキルグリコシドは低刺激性界面
活性剤であり、しかも非イオン性界面活性剤であるにも
拘わらず、それ自身安定な泡を生成するだけではなく、
他の陰イオン性界面活性剤に対して泡安定剤として作用
することが知られており、近年注目されつつある。しか
し、アルキルグリコシドは上記の如く新たな界面活性剤
として注目すべき性質を有しているにも拘わらず、その
実際の製造には多くの困難が伴う。[Prior Art and Problems to be Solved by the Invention] Alkyl glycosides, which are sugar derivative surfactants, are mild surfactants, and even though they are nonionic surfactants, they are themselves stable. In addition to generating bubbles,
It is known to act as a foam stabilizer for other anionic surfactants, and has been attracting attention in recent years. However, although alkyl glycosides have remarkable properties as new surfactants as described above, their actual production is accompanied by many difficulties.
【０００３】アルキルグリコシドは糖類と高級アルコー
ルとの反応によって製造されるが、その中で最も大きい
問題は製造工程における種々の操作によって色相の劣化
が容易に発生することである。[0003] Alkyl glycosides are produced by the reaction of sugars and higher alcohols, but the biggest problem is that the hue easily deteriorates due to various operations in the production process.
【０００４】そのため、従来より製造工程における色相
劣化を防ぐ方法が研究されており、いくつかの解決方法
が提案されている。例えば、まず高級アルコールと単糖
類との反応によりアルキルグリコシドを生成する反応の
段階において、特開昭５９−１３９３９７号公報に記載
されているように酸触媒と還元剤とよりなる酸触媒組成
物の存在下反応を行う方法、欧州特許第０１３２０４３
号明細書に記載されているように触媒としてアニオン活
性剤の酸形を用いる方法、また欧州特許第０１３２０４
６ 号明細書に記載されているように反応を停止するに
際し有機塩基による中和を行う方法等が提案されている
。また、生成したアルキルグリコシドを未反応の回収ア
ルコールと蒸留にて分離する段階ではアルキルグリコシ
ドの高い粘度及び不良な熱安定性ゆえに特に色相の劣化
が著しいため粘度減少剤を添加する方法（特開昭６２−
１９２３９６号公報）の提案がなされているが、いずれ
の方法によっても得られるアルキルグリコシドの色相は
、満足すべきものではなかった。[0004] For this reason, methods for preventing hue deterioration in the manufacturing process have been studied, and several solutions have been proposed. For example, in the reaction stage of producing an alkyl glycoside by reacting a higher alcohol with a monosaccharide, an acid catalyst composition consisting of an acid catalyst and a reducing agent is used, as described in JP-A-59-139397. Method for carrying out reactions in the presence, European Patent No. 0132043
A method using the acid form of an anionic activator as a catalyst as described in EP 0 132 04
As described in Specification No. 6, a method of neutralizing with an organic base upon stopping the reaction has been proposed. In addition, in the step of separating the generated alkyl glycoside from the unreacted recovered alcohol by distillation, the color deterioration is particularly significant due to the high viscosity and poor thermal stability of the alkyl glycoside, so a method of adding a viscosity reducer (JP-A-Show) 62-
192396), but the hue of the alkyl glycoside obtained by either method was not satisfactory.
【０００５】また、特開昭４７−１６４１３ 号公報で
は分離に先立ってアルキルグリコシド製造反応生成物を
水酸基形の塩基性陰イオン交換樹脂と接触させることに
より色相良好なアルキルグリコシドを得ることを提案し
ているが、この場合にはアミン臭発生による匂いの劣化
の懸念があった。更に、特開昭６１−３３１９３ 号公
報では製造により最終的に得られたアルキルグリコシド
を過酸化水素及び二酸化硫黄源を用いて漂白することを
提示しているが、この場合には色相とは別に匂いの面で
の劣化や保存安定性不良といった新たな問題が発生し抜
本的な解決策とは言えない。また特開平１−２９０６９
２号公報には、有色フミンを含んだグリコシド組成物を
水素又は水素化ホウ素ナトリウムなどの水素源と接触さ
せることにより、グリコシド組成物の色を改良する方法
が提案されている。[0005] Furthermore, JP-A-47-16413 proposes that an alkyl glycoside with a good hue can be obtained by contacting the alkyl glycoside production reaction product with a basic anion exchange resin in the form of a hydroxyl group prior to separation. However, in this case, there was a concern that the odor would deteriorate due to the generation of amine odor. Furthermore, JP-A No. 61-33193 proposes bleaching the alkyl glycoside finally obtained by production using a hydrogen peroxide and sulfur dioxide source, but in this case, apart from the hue, New problems arise such as deterioration in odor and poor storage stability, so this cannot be called a fundamental solution. Also, JP-A-1-29069
No. 2 proposes a method for improving the color of a glycoside composition by bringing the glycoside composition containing colored humins into contact with hydrogen or a hydrogen source such as sodium borohydride.
【０００６】このように、色相良好なアルキルグリコシ
ドを製造するために種々の方法の提案が行われているが
、得られたアルキルグリコシドの色相が、未だ満足すべ
きものではなかったり、あるいは匂いの劣化が発生する
など、いずれの方法も色相及び匂いの両方を満足する方
法ではなかった。[0006] As described above, various methods have been proposed for producing alkyl glycosides with good hue, but the hue of the obtained alkyl glycosides is still unsatisfactory, or there is a problem with odor deterioration. None of the methods satisfies both color and odor, such as the occurrence of .
【０００７】アルキルグリコシドの色相劣化は溶解した
未反応糖およびその分解により生成する酸性成分および
フラン誘導体等の着色原因物質であることが主であるが
、糖と高級アルコールを反応させて、反応率（糖の消費
量基準）が９０％以上に達しても、反応生成物内には１
０００〜３０００ｐｐｍ の溶解した未反応糖が残存し
ている。またこの段階から着色が急速に進み、しかも反
応は脱水律速に移行している。従って、反応率が９０％
以上に達した時点で効率的な脱水を行い未反応糖を迅速
に低減させる事が課題であった。Deterioration of the hue of alkyl glycosides is mainly due to coloring substances such as dissolved unreacted sugars, acidic components generated by their decomposition, and furan derivatives. Even if the (sugar consumption standard) reaches 90% or more, there is still 1
000-3000 ppm of dissolved unreacted sugar remains. Furthermore, coloration progresses rapidly from this stage, and moreover, the reaction has shifted to dehydration rate-limiting. Therefore, the reaction rate is 90%
The challenge was to perform efficient dehydration to quickly reduce unreacted sugars when the above-mentioned amount was reached.
【０００８】[0008]
【課題を解決するための手段】本発明者らは、上記課題
を解決すべく鋭意研究の結果、酸触媒を使用して糖と高
級アルコールとを反応させた後、熱履歴が小さく、かつ
脱水効率の良い薄膜状態で熟成反応を行うことにより溶
解した未反応糖を迅速に低減できることを見出し、本発
明を完成した。[Means for Solving the Problems] As a result of intensive research to solve the above problems, the present inventors have found that after reacting sugar and higher alcohol using an acid catalyst, the heat history is small and dehydration is achieved. The present invention was completed based on the discovery that dissolved unreacted sugars can be rapidly reduced by carrying out an efficient aging reaction in a thin film state.
【０００９】即ち、本発明は、糖と高級アルコールとを
用いてアルキルグリコシドを製造するに際し、酸触媒を
使用して糖と高級アルコールとを反応させた後、薄膜状
態で熟成反応を行うことを特徴とするアルキルグリコシ
ドの製造方法を提供するものである。That is, the present invention, when producing an alkyl glycoside using a sugar and a higher alcohol, involves reacting the sugar and the higher alcohol using an acid catalyst and then carrying out an aging reaction in a thin film state. The present invention provides a method for producing a characteristic alkyl glycoside.
【００１０】本発明の熟成反応により、アルキルグリコ
シド中に溶解している未反応糖の含有量を１０００ ｐ
ｐｍ以下とすることが好ましく、５００ ｐｐｍ 以下
とすることが更に好ましい。溶解している未反応糖が１
０００ ｐｐｍを越えると、後の未反応高級アルコール
留去工程において色相劣化が大きくなる。By the ripening reaction of the present invention, the content of unreacted sugar dissolved in the alkyl glycoside can be reduced to 1000 p.
It is preferably at most pm, and more preferably at most 500 ppm. Dissolved unreacted sugar is 1
If it exceeds 000 ppm, hue deterioration will increase in the subsequent step of distilling off unreacted higher alcohols.
【００１１】本発明の糖と高級アルコールとの反応に用
いられる酸触媒としては、パラトルエンスルホン酸、硫
酸、リン酸、強酸性イオン交換樹脂等が挙げられる。酸
触媒の使用量は糖１モル当たり０．００１ 〜０．１０
モルが好ましく、この範囲未満では反応速度が著しく低
下し、この範囲を越えるとアルキルグリコシドの色相が
良好でなくなる。[0011] Examples of the acid catalyst used in the reaction of sugar and higher alcohol of the present invention include para-toluenesulfonic acid, sulfuric acid, phosphoric acid, and strongly acidic ion exchange resins. The amount of acid catalyst used is 0.001 to 0.10 per mole of sugar.
The amount is preferably molar; if it is less than this range, the reaction rate will be significantly reduced, and if it exceeds this range, the color of the alkyl glycoside will not be good.
【００１２】本発明の製造法の原料となる糖類としては
単糖類、オリゴ糖類あるいは多糖類が使用される。単糖
類の具体例としてはアルドース類、例えばアロース、ア
ルトロース、グルコース、マンノース、グロース、イド
ース、ガラクトース、タロース、リボース、アラビノー
ス、キシロース、リキソースなどが挙げられる。オリゴ
糖類の具体例としては、マルトース、ラクトース、スク
ロース、マルトトリオースなどが挙げられる。多糖類の
具体例としてはヘミセルロース、イヌリン、デキストリ
ン、デキストラン、キシラン、デンプン、加水分解デン
プンなどが挙げられる。これらのうち好ましいものは、
炭素数６以下の還元糖である。Monosaccharides, oligosaccharides, or polysaccharides are used as raw materials for the production method of the present invention. Specific examples of monosaccharides include aldoses, such as allose, altrose, glucose, mannose, gulose, idose, galactose, talose, ribose, arabinose, xylose, and lyxose. Specific examples of oligosaccharides include maltose, lactose, sucrose, maltotriose, and the like. Specific examples of polysaccharides include hemicellulose, inulin, dextrin, dextran, xylan, starch, and hydrolyzed starch. Among these, the preferred one is
It is a reducing sugar with 6 or fewer carbon atoms.
【００１３】本発明の製造法の原料となる高級アルコー
ルとしては、直鎖もしくは分岐鎖の炭素数８〜２２の飽
和又は不飽和アルコール又はそのアルキレンオキサイド
付加物が好ましく用いられる。As the higher alcohol serving as a raw material for the production method of the present invention, linear or branched saturated or unsaturated alcohols having 8 to 22 carbon atoms or alkylene oxide adducts thereof are preferably used.
【００１４】本発明において、原料の仕込み比は、糖１
モルに対して、高級アルコール２〜１０モル倍が好まし
く、この範囲未満であれは反応率が低下し、この範囲を
越える場合でも、この範囲内の場合と比較して技術的あ
るいは経済的見地より何等メリットはない。[0014] In the present invention, the charging ratio of raw materials is sugar 1
It is preferable to use 2 to 10 times the mole of higher alcohol.If it is less than this range, the reaction rate will decrease, and even if it exceeds this range, it will be more difficult from a technical or economic point of view than if it is within this range. There is no benefit whatsoever.
【００１５】本発明において、糖と高級アルコールとを
反応させる際の反応は回分方式、連続方式のいずれでも
良く、反応器としては回分式および連続式攪拌槽、懸濁
気泡塔、管型反応器等が用いられる。この時の反応温度
は７０〜１４０ ℃が好ましく、更に好ましくは９０〜
１２０ ℃である。反応温度が１４０ ℃より高いと色
相劣化が大きいばかりではなく、未反応糖同士の縮合物
の生成が多く品質上好ましくない。一方、７０℃未満で
は反応速度が極端に遅くなる。[0015] In the present invention, the reaction between sugar and higher alcohol may be carried out either batchwise or continuously, and the reactor may be a batchwise or continuous stirring tank, a suspension bubble column, or a tubular reactor. etc. are used. The reaction temperature at this time is preferably 70 to 140°C, more preferably 90 to 140°C.
The temperature is 120°C. When the reaction temperature is higher than 140° C., not only is the hue significantly deteriorated, but also a large amount of condensation products between unreacted sugars is produced, which is unfavorable in terms of quality. On the other hand, below 70°C, the reaction rate becomes extremely slow.
【００１６】本発明においては、酸触媒を使用して糖と
高級アルコールとを反応させた後に熟成反応を行うが、
この熟成反応は反応率が９０％以上に達した時点で行う
ことが好ましい。熟成反応は薄膜状態で行い、反応液の
熟成反応は反応液を循環する回分方式、又は連続方式の
いずれの方式でも行うことができる。用いられる薄膜反
応器としては、流下液膜式反応器、上昇液膜式反応器、
ワイプトフィルム蒸発器、ドラム蒸発器等が挙げられる
。
膜厚みは装置によって異なるが、５ｍｍ以下、好ましく
は２ｍｍ以下である。In the present invention, a ripening reaction is carried out after the sugar and higher alcohol are reacted using an acid catalyst.
This aging reaction is preferably carried out when the reaction rate reaches 90% or more. The aging reaction is carried out in a thin film state, and the aging reaction of the reaction solution can be carried out either in a batch system in which the reaction solution is circulated or in a continuous system. Thin film reactors used include falling film reactors, rising film reactors,
Examples include wiped film evaporators and drum evaporators. The film thickness varies depending on the device, but is 5 mm or less, preferably 2 mm or less.
【００１７】上記のような薄膜反応器を用いることによ
り、以下に示すようなメリットがある。
１） 熟成反応は脱水律速の反応であるから、脱水効
率（蒸発効率）の高い薄膜反応器を用いることにより、
反応時間が短縮できる。
２） 薄膜反応器は伝熱効率が良く、熱履歴が小さく
、熱による着色が抑えられる。The use of the thin film reactor as described above has the following advantages. 1) Since the aging reaction is a dehydration rate-limiting reaction, by using a thin film reactor with high dehydration efficiency (evaporation efficiency),
Reaction time can be shortened. 2) Thin film reactors have good heat transfer efficiency, small thermal history, and can suppress coloring due to heat.
【００１８】熟成反応の温度は６０〜１３０ ℃が好ま
しく、更に好ましくは７０〜１１０ ℃である。反応温
度が１３０ ℃より高いと、色相の劣化が大きいばかり
ではなく、アルキルグリコシドの平均縮合度が増大し、
所望の品質のものを得ることが困難になる。一方、６０
℃未満では反応速度が遅くなる。The temperature of the aging reaction is preferably 60 to 130°C, more preferably 70 to 110°C. If the reaction temperature is higher than 130°C, not only will the hue deteriorate significantly, but also the average degree of condensation of the alkyl glycoside will increase.
It becomes difficult to obtain products of desired quality. On the other hand, 60
Below ℃, the reaction rate becomes slow.
【００１９】[0019]
【実施例】以下、実施例により本発明を更に詳細に説明
するが、本発明はこれらの実施例に限定されるものでは
ない。EXAMPLES The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples.
【００２０】実施例１
（ａ） ｎ− デシルアルコール ８００ｇと無水グ
ルコース１８０ｇ及びパラトルエンスルホン酸一水塩０
．６６ｇを２リットル攪拌槽で １１０℃、系内圧力４
０ｍｍＨｇで反応を行った。
その際、反応生成水を効率良く除去する為に、反応液中
に窒素を２００ｍｌ／ｍｉｎ で吹き込んだ。加熱し６
時間の反応後、反応率が９４％に達した。溶解している
未反応グルコースの量は２５００ ｐｐｍであり、色相
はＡＰＨＡ１２０ であった。
（ｂ） 上記反応液を内径２５ｍｍ、管長１０００ｍｍ
の流下式薄膜反応器にて循環流量１．５ リットル／ｍ
ｉｎ 、温度９０℃、系内圧力２０ｍｍＨｇで２時間熟
成反応を行った。反応終了後、減圧を解除し、ＮａＯＨ
０．１２ ｇで中和した後、未反応グルコース等の固
形物を濾別し、反応生成物としての濾液を９００ ｇ得
た。溶解している未反応グルコースの量は４５０ ｐｐ
ｍ であり、色相はＡＰＨＡ２００ 〜１５０ であっ
た。Example 1 (a) 800 g of n-decyl alcohol, 180 g of anhydrous glucose, and 0 g of paratoluenesulfonic acid monohydrate
．． 66g in a 2 liter stirring tank at 110℃, system pressure 4
The reaction was carried out at 0 mmHg. At this time, nitrogen was blown into the reaction solution at a rate of 200 ml/min in order to efficiently remove the water produced by the reaction. Heat 6
After reaction time, the reaction rate reached 94%. The amount of dissolved unreacted glucose was 2500 ppm, and the color was APHA120. (b) Pour the above reaction solution into a tube with an inner diameter of 25 mm and a tube length of 1000 mm.
Circulation flow rate 1.5 liters/m in a falling film reactor
The aging reaction was carried out for 2 hours at a temperature of 90° C. and an internal pressure of 20 mmHg. After the reaction is completed, the reduced pressure is released and the NaOH
After neutralizing with 0.12 g, solids such as unreacted glucose were filtered off to obtain 900 g of a filtrate as a reaction product. The amount of dissolved unreacted glucose is 450 pp
m, and the hue was APHA200-150.
【００２１】（ｃ） 上記反応生成物を１６０ ℃、０
．５ ｍｍＨｇの蒸留条件でデシルグルコシド２５０
ｇと未反応ｎ−デシルアルコール６５０ ｇとに分離し
た。得られたデシルグルコシドを水に溶解し３５％水溶
液を調整して色相を測定した。(c) The above reaction product was heated at 160°C and 0
．． Decyl glucoside 250 under distillation conditions of 5 mmHg
g and 650 g of unreacted n-decyl alcohol. The obtained decyl glucoside was dissolved in water to prepare a 35% aqueous solution, and the hue was measured.
【００２２】比較例１
実施例１（ｂ） における熟成反応を攪拌槽で３時間行
う以外は実施例１と同様にしてデシルグルコシドを得、
同様に色相を測定した。Comparative Example 1 Decyl glucoside was obtained in the same manner as in Example 1, except that the ripening reaction in Example 1(b) was carried out in a stirring tank for 3 hours.
Hue was measured in the same manner.
【００２３】比較例２
実施例１（ａ） と同様にして得た反応液を、減圧解除
後、ＮａＯＨ０．１２ ｇで中和した後、未反応グルコ
ース等の固形物を濾別し、実施例１（ｃ） と同様な方
法でデシルグルコシドを得、同様に色相を測定した。Comparative Example 2 A reaction solution obtained in the same manner as in Example 1(a) was neutralized with 0.12 g of NaOH after releasing the reduced pressure, and solids such as unreacted glucose were filtered off. Decyl glucoside was obtained in the same manner as in 1(c), and the hue was measured in the same manner.
【００２４】表１に実施例１および比較例１〜２におけ
る熟成反応開始時の溶解している未反応グルコースの量
、反応液の色相、および未反応ｎ−デシルアルコール除
去後３５％デシルグルコシド水溶液としたものの色相に
ついて評価した結果を示した。Table 1 shows the amount of unreacted glucose dissolved at the start of the ripening reaction, the hue of the reaction solution, and the 35% aqueous decyl glucoside solution after removing unreacted n-decyl alcohol in Example 1 and Comparative Examples 1 and 2. The results of evaluating the hue of the
【００２５】[0025]
【表１】[Table 1]
【００２６】[0026]
【発明の効果】本発明の方法によると、糖と高級アルコ
ールとを反応させた反応物中の溶解未反応糖を迅速に低
減することができ、色相の良好なアルキルグリコシドを
製造することができる。[Effects of the Invention] According to the method of the present invention, dissolved unreacted sugar in the reaction product of sugar and higher alcohol can be rapidly reduced, and alkyl glycosides with good color can be produced. .
Claims (2)
ルグリコシドを製造するに際し、酸触媒を使用して糖と
高級アルコールとを反応させた後、薄膜状態で熟成反応
を行うことを特徴とするアルキルグリコシドの製造方法
。Claim 1: An alkyl glycoside characterized in that when producing an alkyl glycoside using a sugar and a higher alcohol, the sugar and the higher alcohol are reacted using an acid catalyst, and then a ripening reaction is carried out in a thin film state. Method for producing glycosides.
ド中に溶解している未反応糖の含有量が１０００ ｐｐ
ｍ以下である請求項１記載の製造方法。[Claim 2] The content of unreacted sugar dissolved in the alkyl glycoside obtained by the ripening reaction is 1000 pp.
2. The manufacturing method according to claim 1, wherein the particle diameter is less than or equal to m.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3058597A JPH04295491A (en) | 1991-03-22 | 1991-03-22 | Production of alkylglycoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3058597A JPH04295491A (en) | 1991-03-22 | 1991-03-22 | Production of alkylglycoside |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04295491A true JPH04295491A (en) | 1992-10-20 |
Family
ID=13088913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3058597A Pending JPH04295491A (en) | 1991-03-22 | 1991-03-22 | Production of alkylglycoside |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04295491A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007176893A (en) * | 2005-12-28 | 2007-07-12 | Kao Corp | Method for producing alkylgalactoside |
| JP2008156271A (en) * | 2006-12-22 | 2008-07-10 | Kao Corp | Method for producing alkylgalactoside |
| JP2011079773A (en) * | 2009-10-07 | 2011-04-21 | Kao Corp | Method for producing glycoside |
-
1991
- 1991-03-22 JP JP3058597A patent/JPH04295491A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007176893A (en) * | 2005-12-28 | 2007-07-12 | Kao Corp | Method for producing alkylgalactoside |
| JP2008156271A (en) * | 2006-12-22 | 2008-07-10 | Kao Corp | Method for producing alkylgalactoside |
| JP2011079773A (en) * | 2009-10-07 | 2011-04-21 | Kao Corp | Method for producing glycoside |
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