US3547828A - Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols - Google Patents

Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols Download PDF

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Publication number
US3547828A
US3547828A US759259A US3547828DA US3547828A US 3547828 A US3547828 A US 3547828A US 759259 A US759259 A US 759259A US 3547828D A US3547828D A US 3547828DA US 3547828 A US3547828 A US 3547828A
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alkyl
parts
mixture
alcohol
glucoside
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Richard C Mansfield
James L Rainey
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Rohm and Haas Co
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Rohm and Haas Co
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/12—Polysaccharides, e.g. cellulose, biopolymers

Definitions

  • the invention is concerned with the preparation of alkyl oligosaccharide mixtures whose components have the structure RO(C H O H Where R is selected from the group consisting of aliphatic hydrocarbon radicals ranging from C H to C H and m in the oligosaccharide portion, O(C H O H, is at least 2, but averages 3 or more, glycosyl units. One of the glycosyl units is connected through its first carbon atom to the alkyl group, R.
  • Another object of the invention is the preparation of surface active compositions consisting of mixtures of alkyl oligosaccharides, alkyl glucosides and alkanols.
  • alkyl oligosaccharides are highly effective hydrotropes for alkyl glucosides and mixtures of alkyl glucosides and alkanols. They are readily soluble in strongly alkaline solutions, thus facilitating the formulation of surface active materials in highly alkaline liquid systems. They, as well as mixtures thereof with alkyl glucosides and alkanols, also are useful as textile detergents, particularly in alkaline systems.
  • R ranges from C to C in contrast with the values for R in the present invention which range from C to C
  • the value for m in these maltosides is 2, but unlike the critical requirement for the compositions of the present invention the value for m does not average at least 3.
  • Hori Yakugaku Zasshi, 78, 999 (1955) [C.A., 53, 3073 (1959)]
  • Hori Yakugaku Zasshi, 78, 999 (1955) [C.A., 53, 3073 (1959)]
  • the value for m in those compounds is 2, but does not average at least 3 and thereby fails to meet the essential requirement of the present invention.
  • a lower alkyl glucoside preferably butyl glucoside
  • An acid catalyst is employed in the amount of from about 0.0005 mol per mol of glucose to about 0.05 mol/mol of glucose.
  • the preferred catalyst is H 50 although HCl, HNO p-toluene sulfonic acid, methanesulfonic acid, and other acid, electronaccepting compounds of the group generally classed as Lewis acids, may be employed. If sulfuric acid is employed as a catalyst it is preferred to use from 0.1 to 2.0 g./mol glucose (0.001 to 0.02 mol/mol glucose). If butanol or other lower alkanol is employed the preferred amount would be from 2 to 6 mols/mol glucose.
  • the reaction is carried out at or above room temperature, preferably from to 120 C., by refluxing until the mixture is clear and the glucose is in solution. Alternatively, the water of reaction may be removed during the reflux either by distillation with or without a reflux splitter or by azeotropic separation using hexane, heptane, or other such azeotroping agents.
  • the higher alcohol When conversion of the glucose to butyl glucoside has taken place, or when the reaction mixture is clear, the higher alcohol is added and the excess lower alkanol removed, the removal operation being facilitated by reducing the pressure in order to speed the distillation and keep the distillation temperature from getting too high.
  • the amount of higher alcohol added generally will be from 0.5 to 4.0 mols/mol glucose, it being dependent upon the final composition desired, the average molecular weight of the higher alkyl oligosaccharides which are formed being inversely proportional to the amount of the higher alcohol used. That is, oligomers with relatively high molecular weights are formed if the mol ratio of alcohol to glucose is relatively low, and vice versa.
  • an alcohol interchange reaction (transacetalation), already started, is continued by holding the reaction mixture at elevated temperatures under vacuum (if desired) so as continually to remove the lower alkanol as it and the higher alkyl glucosides and oligosaccharides are formed.
  • the components of the mixtures of alkyl oligosaccharides, alkyl glucosides and alkanols which can be prepared in accordance with the present invention may vary as follows. For each parts by weight of the surface active mixture there may be present:
  • components (a), (b) and (c) are present in fixed ratios to each other as stated. Those values are not absolute, however, for there may be present inert materials, such as lower alkyl glycosides, which make up the balance of the composition.
  • the manner in which these ratios are varied is controlled by the amount of lower alcohol removed.
  • the extent of reaction can be determined by a vapor phase chromatographic method of a sample at any time.
  • the final composition of the product thus is a result not only of the amount of higher alcohol used but also the extent of the transacetalation reaction.
  • the final composition may contain varying amounts of butyl glycosides which, although they do not contribute significantly to surface activity, in some cases they do insure desirable physical properties.
  • Lauryl glucoside d (1 part) and 0121125 oligosaccharide (1 part) C12I%5 oligosaccharide by the mol ratio of alcohol/ glucose and the extent of the transacetalation reaction it is possible to control the nature of the end products of the invention so as to produce compositions with properties that are suitable for the intended use of the product. For example, increased higher alcohol content lowers the products solubility in water and in alkaline solutions, but may cause an improvement in the solubility, or at least lower the viscosity of the product, so that it will be highly useful in a lubricating oil or cosmetic formulation.
  • Materials with relatively high alkyl glucoside contents exhibit good textile detergency although they may not be as soluble in alkaline solutions or as good hydrotropes for other nonionic surfactants as those containing less alkyl glucoside and more alkyl oligosaccharide.
  • a mixture containing a relatively large amount of lauryl glucoside may have solubility properties that are similar to a mixture containing a relatively large amount of a C disaccharide.
  • the novel alkyl oligosaccharide compositions from mixtures thereof along with alcohols and alkyl glucosides, this may be simply done by precipitating the alkyl oligosaccharides with a non-solvent such as acetone.
  • the isolated oligosaccharides are useful as hydrotropes for alkyl glucosides and other surface active agents.
  • Lauryl glucoside prepared from dodeeyl alcohol and glucose and purified in a manner similar to lauryl glucoside Analysis:
  • EXAMPLE 1 Preparation of lauryl glucoside-lauryl oligosaccharidelauryl alcohol mixture
  • EXAMPLE 2 Preparation of octadecyl oligosaccharide A mixture of 180 parts of glucose, 444 parts of butanol, 40 parts of hexane and 2 parts of concentrated sulfuric acid was reacted in a flask with an attached water separator while the water of reaction was collected and butyl glycosides were formed. There was then added 540 parts of stearyl alcohol, and butanol was distilled out. The mixture was maintained at 100105 C./4-5 mm. Hg. while the alcohol interchange reaction took place. The mixture was neutralized with 50% aqueous sodium hydroxide. The product was washed seven times with 3 liter portions of acetone.
  • EXAMPLE 4 Preparation of a mixture of alcohols, alkyl glucosides and alkyl oligosaccharides in which the alkyl group of each component is a mixture of C H and C H
  • a mixture of parts of glucose, 111 parts of butanol, about 4 parts of hexane and 0.25 part of concentrated sulfuric acid was stirred and refluxed while 10 parts of water was collected in a water separator.
  • the mixture was held at 110 C./ 10 millimeters of mercury while butanol was removed by distillation and the alcohol interchange reaction was taking place.
  • the mixture was then neutralized with 5 parts of 50% sodium hydroxide solution. It was diluted with parts of heptane and a practically clear solution resulted.
  • a sample was removed for evaluation as a surfactant in gasoline.
  • EXAMPLE 4a Preparation of a mixture of octadecyl alcohol, octadecyl glucoside and octadecyl oligosaccharides
  • EXAMPLE 5 Preparation of a mixture of a quaternary ammonium cat- 1on1c surface active agent and an alkyl glucoside-alkyl oligosaccharide-alkanol mixture
  • EXAMPLE 6 Preparation of various mixtures of alkanols, alkyl glucosides and alkyl oligosaccharides
  • the general procedure, already described, for synthesizing a mixture of alkanols, alkyl glucosides, and alkyl oligosaccharides from glucose and a higher alcohol via a butyl glycoside intermediate was used to prepare a variety of products.
  • the alcohol used in these experiments was a commercially available mixture comprised predominantly of dodecyl and tridecyl alcohols, leading to the formation of C H and C H alkanols, alkyl glycosides and alkyl oligosaccharides.
  • Various mol ratios of alcohol/glucose were used, the products were analyzed by vapor phase chromatography of the trimethylsilyl derivatives, and the results are shown in Table II below:
  • EXAMPLE 7 The same general preparative method was used to prepare a series of alkyl oligosaccharide-alkyl glucoside-alkanol mixtures. These crude mixtures were washed with acetone to remove the alcohol and alkyl glucoside. The residual alkyl oligosaccharide mixtures were analyzed by vapor phase chromatography of the trimethylsilyl derivatives and are shown in the following table.
  • a mixture consisting essentially of alkyl oligosaccharides, alkyl glucosides and alkanols, the surface active ingredients of which mixture, for each 100 parts by weight present, consists of:
  • ROH is a mixture of H25C120H, H27C13OH, H29C140H and H31C15OH; is a mixture Of H25C1ZOG, H27C13OG, H29C14OG, and H C OG; and R'O(C H O H is a mixture of 25 1z e 1o 5)m 2'1 1a 6 10 5)m 29 14 6 10 5)m and H31C150 6 10 s)m

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Saccharide Compounds (AREA)
  • Detergent Compositions (AREA)
US759259A 1968-09-03 1968-09-03 Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols Expired - Lifetime US3547828A (en)

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US75925968A 1968-09-03 1968-09-03

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BE (1) BE737973A (enrdf_load_stackoverflow)
DE (1) DE1943689A1 (enrdf_load_stackoverflow)
FR (1) FR2017240A1 (enrdf_load_stackoverflow)
GB (1) GB1284456A (enrdf_load_stackoverflow)
NL (1) NL6913461A (enrdf_load_stackoverflow)

Cited By (163)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3839318A (en) * 1970-09-27 1974-10-01 Rohm & Haas Process for preparation of alkyl glucosides and alkyl oligosaccharides
US3912713A (en) * 1973-08-29 1975-10-14 Scholten Honig Research Nv Guar gum derivatives and process for preparation
US4196201A (en) * 1977-05-18 1980-04-01 L'oreal Non-irritating eye make-up remover composition
JPS58104625A (ja) * 1981-07-13 1983-06-22 ザ・プロクタ−・エンド・ギヤンブル・カンパニ− 起泡性界面活性剤組成物
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US4483779A (en) * 1982-04-26 1984-11-20 The Procter & Gamble Company Detergent compositions comprising polyglycoside and polyethoxylate surfactants and anionic fluorescer
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NL6913461A (enrdf_load_stackoverflow) 1970-03-05

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