NO832271L - Fremgangsmaate for fremstilling av organoglykosidblandinger - Google Patents
Fremgangsmaate for fremstilling av organoglykosidblandingerInfo
- Publication number
- NO832271L NO832271L NO832271A NO832271A NO832271L NO 832271 L NO832271 L NO 832271L NO 832271 A NO832271 A NO 832271A NO 832271 A NO832271 A NO 832271A NO 832271 L NO832271 L NO 832271L
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- water
- alcohol
- starch
- saccharide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 51
- 229920002472 Starch Polymers 0.000 claims abstract description 41
- 235000019698 starch Nutrition 0.000 claims abstract description 41
- 239000008107 starch Substances 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 31
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 16
- 239000005017 polysaccharide Substances 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 239000012429 reaction media Substances 0.000 claims abstract description 14
- 239000006184 cosolvent Substances 0.000 claims abstract description 6
- 150000004676 glycans Chemical class 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 26
- 239000002270 dispersing agent Substances 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 19
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 229960001031 glucose Drugs 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- -1 alkyl glycosides Chemical class 0.000 abstract description 48
- 229930182470 glycoside Natural products 0.000 abstract description 45
- 150000001298 alcohols Chemical class 0.000 abstract description 7
- 239000003377 acid catalyst Substances 0.000 abstract description 3
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- 238000002474 experimental method Methods 0.000 description 37
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- 150000002338 glycosides Chemical class 0.000 description 13
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
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- 238000004519 manufacturing process Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 239000000706 filtrate Substances 0.000 description 3
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- 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
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 150000001323 aldoses Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
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- 238000006073 displacement reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
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- 239000012066 reaction slurry Substances 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-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
- 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
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- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011345 viscous material 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39622882A | 1982-07-08 | 1982-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO832271L true NO832271L (no) | 1984-01-09 |
Family
ID=23566388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO832271A NO832271L (no) | 1982-07-08 | 1983-06-22 | Fremgangsmaate for fremstilling av organoglykosidblandinger |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0099183A1 (pt) |
| JP (1) | JPS5946295A (pt) |
| AU (1) | AU1619483A (pt) |
| BR (1) | BR8303624A (pt) |
| DK (1) | DK309783A (pt) |
| NO (1) | NO832271L (pt) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4557729A (en) * | 1984-05-24 | 1985-12-10 | A. E. Staley Manufacturing Company | Color stabilization of glycosides |
| EP0319616B1 (en) * | 1987-11-30 | 1995-01-11 | HENKEL CORPORATION (a Delaware corp.) | Glycoside preparation |
| DE3623246A1 (de) * | 1986-07-10 | 1988-01-14 | Huels Chemische Werke Ag | Verfahren zur herstellung von butyloligoglycosiden |
| DE3624863A1 (de) * | 1986-07-23 | 1988-01-28 | Huels Chemische Werke Ag | Verfahren zur gewinnung von butyloligoglycosiden |
| US4996306A (en) * | 1988-04-05 | 1991-02-26 | Henkel Kommanditgesellschaft Auf Aktien | Glycoside preparation directly from aqueous saccharide solutions or syrups |
| DE3827534A1 (de) * | 1988-08-13 | 1990-02-22 | Henkel Kgaa | Verfahren zur herstellung von alkylglucosidverbindungen aus oligo- und/oder polysacchariden |
| DE3900590A1 (de) * | 1989-01-11 | 1990-07-12 | Henkel Kgaa | Verfahren zur herstellung von alkylglucosiden |
| US5476924A (en) * | 1989-01-27 | 1995-12-19 | Duke University | Protecting group for acetals and methods of using the same in the activation of saccharides |
| DE4006192A1 (de) * | 1990-02-28 | 1991-08-29 | Huels Chemische Werke Ag | Verfahren zur herstellung von kohlenhydrattensiden |
| DE4034074A1 (de) * | 1990-10-26 | 1992-04-30 | Huels Chemische Werke Ag | Verfahren zur herstellung von alkylglycosiden und alkyloligoglycosiden |
| US5512666A (en) * | 1994-07-22 | 1996-04-30 | Henkel Corporation | Process for making alkyl polyglycosides |
| WO2015101454A1 (en) | 2013-12-30 | 2015-07-09 | Unilever N.V. | Detergent composition |
| WO2023213524A1 (en) | 2022-05-06 | 2023-11-09 | Unilever Ip Holdings B.V. | Detergent composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2390507A (en) * | 1941-01-21 | 1945-12-11 | Corn Prod Refining Co | Production of alkyl glycosides |
| US4223129A (en) * | 1978-09-01 | 1980-09-16 | A. E. Staley Manufacturing Company | Continuous process for making alkyl aldosides from starch or other carbohydrates |
-
1983
- 1983-06-15 EP EP83303451A patent/EP0099183A1/en not_active Withdrawn
- 1983-06-22 NO NO832271A patent/NO832271L/no unknown
- 1983-06-23 AU AU16194/83A patent/AU1619483A/en not_active Abandoned
- 1983-07-05 DK DK309783A patent/DK309783A/da not_active Application Discontinuation
- 1983-07-06 BR BR8303624A patent/BR8303624A/pt unknown
- 1983-07-08 JP JP12457083A patent/JPS5946295A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BR8303624A (pt) | 1984-02-14 |
| DK309783A (da) | 1984-01-09 |
| DK309783D0 (da) | 1983-07-05 |
| AU1619483A (en) | 1984-01-12 |
| JPS5946295A (ja) | 1984-03-15 |
| EP0099183A1 (en) | 1984-01-25 |
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