TW314524B - - Google Patents
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- Publication number
- TW314524B TW314524B TW083109655A TW83109655A TW314524B TW 314524 B TW314524 B TW 314524B TW 083109655 A TW083109655 A TW 083109655A TW 83109655 A TW83109655 A TW 83109655A TW 314524 B TW314524 B TW 314524B
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- TW
- Taiwan
- Prior art keywords
- patent application
- reaction
- application scope
- membrane
- item
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 238000001704 evaporation Methods 0.000 claims description 25
- 230000008020 evaporation Effects 0.000 claims description 24
- -1 alkyl glucosamine Chemical compound 0.000 claims description 18
- 239000012528 membrane Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 238000006206 glycosylation reaction Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000008103 glucose Substances 0.000 claims description 6
- 238000011049 filling Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 102000051325 Glucagon Human genes 0.000 claims 1
- 108060003199 Glucagon Proteins 0.000 claims 1
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims 1
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 claims 1
- 229960004666 glucagon Drugs 0.000 claims 1
- 229960002442 glucosamine Drugs 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 1
- 230000001502 supplementing effect Effects 0.000 claims 1
- 239000010408 film Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000000855 fermentation Methods 0.000 description 10
- 230000004151 fermentation Effects 0.000 description 10
- 229930182478 glucoside Natural products 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 229930182470 glycoside Natural products 0.000 description 7
- 230000000149 penetrating effect Effects 0.000 description 5
- 230000013595 glycosylation Effects 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- 239000012465 retentate Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-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
- WYUFTYLVLQZQNH-JAJWTYFOSA-N Ethyl beta-D-glucopyranoside Chemical compound CCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WYUFTYLVLQZQNH-JAJWTYFOSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JVAZJLFFSJARQM-RMPHRYRLSA-N (2r,3r,4s,5s,6r)-2-hexoxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JVAZJLFFSJARQM-RMPHRYRLSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- 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
- ZVKPGHYZRCHUJO-UHFFFAOYSA-N 4-ethenoxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=C(C(=O)OC=C)C=C1 ZVKPGHYZRCHUJO-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-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
- 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
- 239000004698 Polyethylene Substances 0.000 description 1
- 229930006000 Sucrose Natural products 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
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000011068 loading method Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000005373 pervaporation Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000010457 zeolite Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/36—Pervaporation; Membrane distillation; Liquid permeation
- B01D61/362—Pervaporation
- B01D61/3621—Pervaporation comprising multiple pervaporation steps
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/1893—Membrane reactors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00105—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling
- B01J2219/00114—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling involving reactant slurries
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
Description
314524 A7 ______B7_ 五、發明説明(1 ) 本發明係有闞製備烷基釀苷的方法,其係在酸性觸媒存 在中’用酵與醣反應或用高碳數酵與低碳數烷基醣苷反應 ;且本發明亦有鼷如此所製成的烷基釀苷,及其在界面活 性組合物中的用途。此外,本發明也有闞實施本發明方法 的装置。 在酸性觸媒中*用釀和酵經由_苷化或用低碳數烷基藤 苷和高碳數酵進行再釀苷化Μ製備烷基釀苷係已知重。布 克博士(Dr Th. Bocher)和希姆教授(Prof Dr T. T h i e m )在 T e n s i d e S u r f . . D e t. , V ο 1 . 2 6,Ν ο . 5 , 318-324 (1989)中發表遇有醑許多種烷基釀苷合成的評論 Ο 烷基醣苷製備中的問題之一為要將反應中形成的水快速 脫除Μ使反應速率成為經濟上可接受者。 經濟部中央標準局員工消費合作社印袋 (請先《讀背面之注意事項再填寫本頁) 頃發現經由採用全蒸發方式埋續脫除掉反應水可Μ在更 高反應速率和更高的最後轉化率之下得到烷基釀苷。於全 蒸發中,係將液體給料(含有一更具穿透性成份及一較低 穿透性成份)保持與穿透膜接觸並維持跨膜壓力降。需被 脫除掉的成份從給料液體中出來並通過該《。通遇該膜且 為蒸氣形式的穿透物可在低溫冷凝回收或用移動氣體流將 其帶走。 較佳者,該膜的穿透物側係保持在5 me Hg(0.67 KPa) 大小的低壓。分雛單元所保留的殘餘給料稱為保留物或濃 縮物。於蒸氣全蒸發程序中,給料混合物先蒸發後,將蒸 氣沿著膜通過。 -4- 本紙張尺度適用中國國家標準(CNS ) A4规格(2丨0X297公釐) 314524 a? B7 五、發明説明(2 ) 全蒸發方法在W. S. Winston Ho和K. K. Sirkar, ”薄膜 手冊"(Membrane Handbook}, Van Nostrund Reinhold P u b 1 i s h i n g C o r* p . , N e w Y o r k , 1 9 9 2 , 1 0 5 - 1 5 9 頁中有較 詳细地說明。 綜上所述,本發明係有闞一種製備烷基醣苷的方法*其 係在酸性觸媒存在中*用酵與_反應,或用高碳數酵與低 碳数烷基釀苷反應,該方法的特徽在於在該方法装置中安 裝至少一傾全蒸發膜使得反應水可透a該膜而從反應混合 物中連鑛脫除掉。 可用於本發明方法中的_較佳者包括水溶性單釀,例如 葡萄糖,果糖,半乳糖,甘霣糖,木糖,阿拉伯耱等,及 較佳者水溶性多醣,如蔗糖,麥芽糖,麥芽三糖*乳糖等 ,和軍_與多_的混合物等。該釀物質較佳者是Μ在要形 成烷基醣的酵中之漿液或分散液形式使用。最好是使用葡 萄耱和果糖。 所用的酵為具有1到6個碳原子的單羥基,飽和,直鐽 或支鍵酵,例如甲酵,乙酵,丙酵,異丙酵,丁酵*及其 混合物等。此外,也可Κ使用多羥基飽和脂族酵*如乙二 酵*丙二酵,甘油等*於這種情況中會形成羥烷基醣苷。 經濟部中央標準局員工消費合作杜印製 (請先聞讀背面之注意事項再填寫本夏) 可用的低碳數烷基釀苷為h-Ce烷基醣苷,如甲基醣脊 ,乙基醣苷,己基_苷等。 用於本發明再_苷化反應中的高碳數酵係選自具有8至 24個碳原子的直鍵或支鍵單羥基酵,如辛醇•十二烷酵等 -5 - 本紙張尺度逍用中國國家揉準(CNS ) Α4規格(2!0><297公釐) 314524 A7 B7 五、發明説明(3 ) 。通常係用具有12至18個碳原子的脂肪醇混合物。 (請先聞讀背面之注$項再填寫本頁) 一般而言,係採用60C至180= 的反應溫度,且較佳者 係在8〇υ至ΐ4〇υ 完成該反應。該反應可在超大氣壓,大 氣壓和次大氣壓等懕力下進行。另外,也可以施加惰性氣 圍。至於該酸性觸媒*可W使用液體或固體,無機或有機 酸,如硫酸,磷酸,磺酸,離子交換樹脂(如,苯乙烯二 乙烯基苯類型者),酸活化漂白土,酸性沸石(如,高孔 洞容積的氧化矽-氧化鋁裂解觸媒> ,及上述之混合物等 。該觸媒也可以提供成在反應器内的所謂固定床形式,使 用離子交換樹脂作為觸媒有其優點,亦即,該膜不會受到 酸侵害•因而在缠當膜的選擇上有更大的彈性。 該反應可在攪拌播式反應器或一系列攪拌檐式反應器内 進行,不通也可以在膠凝膜蒸發器中進行。該反應器後面 接著全蒸發單元•從該軍元可將保留物循環到反應器内。 穿透物可再接受進一步處理。於必要時,可在反應器與全 蒸發軍元之間装設一過滹軍元。 經濟部中央標準局貝工消費合作社印製 全蒸發作用係透過全蒸發膜而進行的。該膜可為任何市 面上可得種類,只要其對反應混合物具有足夠抗性即可。 全蒸發膜典型者為多層膜,包括一活性(改質)聚乙烯酵外 層,可為聚丙烯腈層的孔洞背層及可為不嫌型聚_,如聚 (對苯二甲酸乙烯酯)的支架層。·此外,也可κ使用其他 逋當類型的薄膜。另外的方式,可將該活性全蒸發膜接著 到陶瓷微漶模組的内表面。為了從本發明方法得到最佳結 果,在該膜低壓側的壓力可適當地為1至100毫巴,較佳 -6- 本紙張尺度逍用中國國家標準(CNS ) Α4規格(210X297公釐) 31452#8 中文說明書修正頁(86年7月) 13109655號專利申請案
經濟部中央標準局貝工消費合作社印製 五、發明説明() 者為1至20毫巴。 該全蒸發較佳者是在得到透明反應混合物時起始。 實施本發明方法的適當裝置包括一醣苷化或再醣苷化反 應器,將醣或低碳數烷基瑭苷及醇或高碳數酵給入的工具 ’和’適需要選用的將惰性氣體給到反應器内的工具,及 一全蒸發装置’其係連接到反應器K從其中接收_苷化或 再醣苷化反應產物混合物,且其包含一全蒸發膜,將反應 水從全蒸發装置取出的工具和將反應混合物保留物從全蒸 發裝置循環到反應器内部的工具。 較佳者,在全蒸發裝置的作用過程中,醣苷化或再醣苷 化反應混合物中不含固體醣或觸媒,且為達到此目的,最 好是在反應器與全蒸發裝置之間裝設一過濾單元。 本發明至此要用下面的實施例予K閫明。 騸式簡罝說明 圖1係顯示列於實例1之二則反應之轉化率與時間的關 係,一則反應具全蒸發及一則不具全蒸發。圖中顯示全蒸 發之應用使達到較高之終轉化率且需較短的製程時間達到 特定轉化率。圖2係顯示相同反應之反應介質的水量。不 具全蒸發時,水量於反應期間不斷增加。將全蒸發裝置與 反應器偶合則水濃度首先增加,然後達到最大量及接著於 反應期間不斷減少。
當倫例T 將0.945公斤的葡萄糖與0.5重量3ί(Μ葡萄糖重量計) 的對-甲苯磺酸混合並將該混合物加到已裝著1 2 0 0克無水 -7- 本紙張尺度適用中國國家標準(CNS ) Α4規格(210Χ 297公釐) 丨裝 訂 ^ 線 (請先閱讀背面之注意事項再填寫本頁) 第83109655號專利申請案 中文說明書修正頁(86年7月) A7 B7 8b. 7.11 年月曰補免 五、發明説明() 乙酵的5升容積不銹鋦套層容器内。該容器裝著一變速攪 拌器及必需的输入管和输出管。將乙醇漿液中的葡萄糖與 1415克的無水乙醇混合並將混合物於搜拌下加熱到100 t 直到所有葡萄糖都溶解在反應混合物中為止。於反應混合 物已到達100T:溫度後兩小時,將其於22小時期間連續地 泵取過全蒸發膜的表面(Celfa CMC-Α膜,活性面積0.04平 方米,註冊商標,產自CM-CELFA Membrantrenntechnik AG . S w i t z e r丨a n d )及循環到反應容器。在該全蒸發膜给料 測的壓力為2巴。而於該膜另一側則用一真空泵保持在1 裝 訂 線 (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印裝 本紙張尺度適用中國國家標準(CNS ) Α4規格(210Χ 297公釐) 314524 kl _B7_ 五、發明説明(5 ) 毫巴壓力。將膜所脫除出來的水冷凝並收集在一玻璃燒瓶 内0 於一第二實驗中,係在相同條件下進行該反應,但沒有 使用全蒸發裝置。圖1示出兩實驗所得轉化率與時間的闞 係。可K看出有施用全蒸發時,可得到較高的最後轉化率 且達到某一轉化率所需的程序時間也較短。 圖2所示為反應混合物中的水含量。在沒有全蒸發時* 該水含量會在反應過程中逐漸增加。而有全蒸發裝置配合 反應器之情況下,水濁度會先增高,達到一最高點,然後 於反應過程中逐漸減低。反應混合物中有較低水含霣時會 減低逆化學反應的速率,因而對於乙基葡萄糖苷的形成得 到較高的總反應速率。
g life 例 I 重複實施例I *但此次係使用不同的全蒸發膜(Car-bone-Lorraine Type CL 1000, 註 冊商標 ,產自 Le Car-bone-Lorraine S.A.,法國,巴黎)。於24小時後》得到 98.9X的乙基葡萄糖苷轉化率;反應器內的水含量為0.20 重量X且穿透物中的水濃度為52.4重量X (水通量為0.03公 斤/平方米小時)。 經濟部中央標準局貝工消費合作社印袋 (請先閱讀背面之注意事項再填寫本頁) 若對某一反應器尺寸安置更多的膜面積時,會Μ更高的 速率從反應器脫除水份,促成更高反應速率和更高的平衡 轉化率。不過*同時*該全蒸發單元會更昂貴。因此之故 *對某一反應器尺寸會有一具經濟最遘性膜尺寸。此外, 在減低反應器装載*因而增高贓面積與反應器尺寸之間的 比例時*可達到較高的反臛速率及更高的最後轉化率。 -8 - 本紙張尺度適用中國國家揉準(CNS ) Α4规格(210X297公釐)
Claims (1)
- 第83109655號專利申請案 中文申請專利範圍修正本(86年7月) A8 B8 C8 D8 86, 7a 11 六、申請專利範圍 5 . 6 . 補充 一種製備烷基葡糖苦之方法I其係在酸性觸媒存在下, 以具有1至6個碳原子的單羥基醇與葡萄糖反應(;糖苷 化反應),其特徵在於在該方法裝置中裝設至少一個全 蒸發膜使得反應水可透過該膜從反應混合物中連續被移 除° 根據申請專利範圍第1項之方法,其中該糖脊化反應係 在60Ϊ:至1801C 溫度下進行。 根據申請專利範圍第2項之方法,其中該糖苷化反應係 在80C至14〇υ 溫度下進行。 根據申請專利範圍第1項之方法,其中該全蒸發膜包含 聚乙烯醇活性層,聚丙烯腈背層和不織型聚酯負載層。 根據申請專利範圍第1項之方法,其中該全蒸發膜係接 附在陶瓷微漶膜的内側表面上。 根據申請專利範圍第1項之方法,其中在該全蒸發膜低 壓力側的壓力為1至100毫巴。 根據申請專利範圍第1項之方法,其中於全蒸發作用期 間,無固體葡糖苦或催化劑在通過全蒸發膜加工前藉通 過過滤裝置經過反應混合物而存在於反應混合物中。 ---------^------1Τ------# (請先聞讀背面之注意事項再填寫本頁) 經濟部中央標準局貝工消費合作社印製 1 - 本紙張尺度適用中國國家標準(CNS ) Α4規格(210 X 297公釐)
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JP3051833B2 (ja) * | 1997-05-23 | 2000-06-12 | 花王株式会社 | アルキルグリコシドの製造方法 |
DE19802277A1 (de) * | 1998-01-22 | 1999-07-29 | Henkel Kgaa | Verfahren zur Herstellung von kurzkettigen Alkyl- und/oder Alkenyloligoglykosiden |
NL1009218C2 (nl) | 1998-05-20 | 1999-11-24 | Akzo Nobel Nv | Bereiding van een polymeer onder toepassing van een anorganisch membraan met een kleine gemiddelde poriegrootte. |
EP1167333A3 (en) * | 2000-06-26 | 2002-07-31 | F. Hoffmann-La Roche Ag | Process and manufacturing equipment for preparing acetals and ketals |
US6528025B1 (en) | 2000-06-26 | 2003-03-04 | Roche Vitamins Inc. | Process of manufacturing equipment for preparing acetals and ketals |
DE10041577A1 (de) * | 2000-08-24 | 2002-03-14 | Inst Technologie Der Kohlenhyd | Verfahren zur Herstellung von Alkylglycosiden, insbesondere Alkylfructosiden |
DE102004025195A1 (de) * | 2004-05-22 | 2005-12-08 | Goldschmidt Gmbh | Verfahren zur Herstellung von Alkylglycosiden |
CN104418923B (zh) * | 2013-08-23 | 2016-07-06 | 河北科技大学 | 一种烷基糖苷精制漂白方法及设备 |
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US4987225A (en) * | 1988-12-23 | 1991-01-22 | Henkel Kommanditgesellschaft Auf Aktien | Removal of water miscible materials from glycoside mixtures |
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US5496932A (en) * | 1993-04-14 | 1996-03-05 | Henkel Corporation | Process for the production of alkylpolyglycoside |
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ZA947143B (en) | 1996-03-15 |
JPH09502705A (ja) | 1997-03-18 |
EP0719270B1 (en) | 1997-04-23 |
ES2102251T3 (es) | 1997-07-16 |
WO1995007915A1 (en) | 1995-03-23 |
CN1045606C (zh) | 1999-10-13 |
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