CA1301752C - Decoloration de glycosides - Google Patents

Decoloration de glycosides

Info

Publication number: CA1301752C
Authority: CA; Canada
Prior art keywords: glycoside; hydrogenation; color; catalyst; composition
Prior art date: 1988-04-18
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.): Expired - Lifetime

Application number

CA000564361A

Other languages

English (en)

Inventor

Robert S. Mcdaniel, Jr.

Patrick M. Mccurry

Rolland W.P. Short

Paul R. Glor

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Henkel Corp

Original Assignee

Henkel Corp

Priority date (The priority date 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 date listed.)

1988-04-18

Filing date

1988-04-18

Publication date

1992-05-26

1988-04-18 Application filed by Henkel Corp filed Critical Henkel Corp

1988-04-18 Priority to CA000564361A priority Critical patent/CA1301752C/fr

1992-05-26 Application granted granted Critical

1992-05-26 Publication of CA1301752C publication Critical patent/CA1301752C/fr

2009-05-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229930182470 glycoside Natural products 0.000 title claims abstract description 89
150000002338 glycosides Chemical class 0.000 title claims abstract description 87
238000004042 decolorization Methods 0.000 title description 2
239000003054 catalyst Substances 0.000 claims abstract description 62
239000000203 mixture Substances 0.000 claims abstract description 59
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 51
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 43
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims abstract description 35
230000008569 process Effects 0.000 claims abstract description 34
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 31
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 25
239000001257 hydrogen Substances 0.000 claims abstract description 21
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
-1 alkali metal aluminum hydride Chemical class 0.000 claims abstract description 20
229910052759 nickel Inorganic materials 0.000 claims abstract description 19
229910052763 palladium Inorganic materials 0.000 claims abstract description 14
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 10
229910052697 platinum Inorganic materials 0.000 claims abstract description 10
239000002663 humin Substances 0.000 claims abstract description 8
239000012279 sodium borohydride Substances 0.000 claims abstract description 7
229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 7
150000001340 alkali metals Chemical class 0.000 claims abstract description 5
239000012280 lithium aluminium hydride Substances 0.000 claims abstract description 3
229930182478 glucoside Natural products 0.000 claims description 24
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
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KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 6
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
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150000004676 glycans Polymers 0.000 description 1
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SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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239000012285 osmium tetroxide Substances 0.000 description 1
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150000002941 palladium compounds Chemical class 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
150000004804 polysaccharides Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
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238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
150000008223 ribosides Chemical class 0.000 description 1
GTCKPGDAPXUISX-UHFFFAOYSA-N ruthenium(3+);trinitrate Chemical compound [Ru+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GTCKPGDAPXUISX-UHFFFAOYSA-N 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
235000015500 sitosterol Nutrition 0.000 description 1
229950005143 sitosterol Drugs 0.000 description 1
NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
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235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
235000016831 stigmasterol Nutrition 0.000 description 1
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BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
239000010902 straw Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000008202 talosides Chemical class 0.000 description 1
229910002058 ternary alloy Inorganic materials 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
UDKYUQZDRMRDOR-UHFFFAOYSA-N tungsten Chemical compound [W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W][W] UDKYUQZDRMRDOR-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Saccharide Compounds (AREA)

CA000564361A 1988-04-18 1988-04-18 Decoloration de glycosides Expired - Lifetime CA1301752C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000564361A CA1301752C (fr)	1988-04-18	1988-04-18	Decoloration de glycosides

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000564361A CA1301752C (fr)	1988-04-18	1988-04-18	Decoloration de glycosides

Publications (1)

Publication Number	Publication Date
CA1301752C true CA1301752C (fr)	1992-05-26

Family

ID=4137856

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000564361A Expired - Lifetime CA1301752C (fr)	1988-04-18	1988-04-18	Decoloration de glycosides

Country Status (1)

Country	Link
CA (1)	CA1301752C (fr)

1988
- 1988-04-18 CA CA000564361A patent/CA1301752C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2002-05-27	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 20020527

Publication	Publication Date	Title
EP0338151B1 (fr)	1994-08-03	Décoloration des glycosides
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US4430253A (en)	1984-02-07	Sulfide-modified ruthenium catalyst
EP0306650B1 (fr)	1991-11-27	Procédé pour la préparation d'alkylglycosides
CA2180896A1 (fr)	1997-01-12	Composition d'acide polyhydroxycarboxylique derivee de maltodextrines par oxydation a l'aide d'un oxydant renfermant de l'oxygene
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JP3139686B2 (ja)	2001-03-05	アルキルグリコシドおよびアルキルポリグリコシドの製造方法
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NL1000511C2 (nl)	1998-08-12	Werkwijze voor de bereiding van isomaltitol.
US3691100A (en)	1972-09-12	Tungsten oxide promoted and supported nickel catalyst
US4382150A (en)	1983-05-03	Method for hydrogenating aqueous solutions of carbohydrates
CA1301752C (fr)	1992-05-26	Decoloration de glycosides
US6156543A (en)	2000-12-05	Method for preparing surface-active agents
JP2614079B2 (ja)	1997-05-28	グリコシドの脱色
CA2108091A1 (fr)	1994-04-11	Procede de separation de solutions d'alcool gras-alkyl-polyglycosides
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DE3850960T2 (de)	1994-12-22	Entfärbung von Glycosiden.
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JP3142049B2 (ja)	2001-03-07	アルキルグリコシドの製造方法
US5312907A (en)	1994-05-17	Glycosiduronic acids
US3046312A (en)	1962-07-24	Process for making erythritol and ethylene glycol from polymeric dialdehydes