JPH04506338A - Method for removing water miscible substances from glycoside mixtures - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Background of the invention: Method for removing water miscible substances from glycoside mixtures The present invention generally removes unnecessary polysaccharides and other hydrophilic components from hydrophobic compounds containing them. Methods for removing glycoside surfactants 7/hydrophobic alcohols from chemical compositions, in particular or from other hydrophobic solvent compositions or polysaccharide-containing mixed hydrophobic alcohols/glycans. The present invention relates to a method for removing cocidal surfactants from compositions. In one embodiment, the invention The method involves separating hydrophobic alcohols from the desired glycoside surfactant product by evaporation. Before releasing the crude polysaccharide-containing hydrophobic alcohol/glycoside surfactant reaction product A method for producing a glycoside surfactant, which involves applying the polysaccharide removal technique described above to a mixture. nothing.

According to this method, the hydrophobic aglycone substituent has an average of at least 9 carbon atoms. including children, the average degree of polymerization (D, P,) is at least 1, 2, and unnecessary polymerization Substantially free of sugar components (i.e., 0 based on the total weight of glycoside surfactants) ．． 5% by weight or less) and has a degree of polymerization of 10 or more. Novel glycoside containing 5% by weight or less (preferably 1% by weight or less) of glycoside species A surfactant composition is obtained. This method produces purified substances for specific uses It is useful for purifying alkyl polyglycoside products for the purpose of purifying alkyl polyglycoside products.

Long chain alkyl monoglycosides and long chain alkyl polyglycosides and their The mixture (hereinafter collectively referred to as "glycoside surfactants") is a known substance. It is known to have surfactant properties and has a wide range of domestic and industrial uses. Known to be useful in applications. Furthermore, in the presence of acid catalysts, long-chain amines are Hydrolysis of alcohol to saccharide reactants (e.g., monosaccharides or Glycoside surfactants can be produced by reacting with is also known.

A method for producing alkyl glycoside compositions is disclosed in U.S. Pat. No. 3,219,656; Same No. 3.547.828, Same No. 3.598.865, Same No. 3,707,53 No. 5, No. 3.772,269, No. 3,839.318, No. 4.349 ．． 669, No. 4,393,203, No. 4.472.170, No. 4. 510.306, 4,597.770, 4.704.453, 4.704.453, No. 4,713.447, European Patent Application No. 0092355, oo9e9t 7 and 0132043.

In the acid-catalyzed reaction process of sugar reactants/long chain alcohols mentioned above, chemical A substantial stoichiometric excess of long chain alcohol reactant is used. The first manufactured i.e., the reaction product obtained without intervening separation, fractional distillation or purification operations. The mixture typically contains a substantial amount of residual unreacted long chain alcohol, a major amount on a mole percent basis. monoglycosides of long-chain alcohols as glycoside molecular species, gradually decreasing Various mole percentages or proportions of long chain alcohol polyglycoside species with high degree of polymerization, Mass but varying amounts of chemically bonded (i.e. covalently bonded) length Polysaccharide by-products without chain alcohol molecules and species such as catalysts and processing aids Contains various substances.

According to various prior art techniques, vacuum distillation, organic solvent (e.g. acetone) extraction or fractionation are used. Various techniques such as distillation, and thin film (or coated film) distillation (4) It is common to remove residual unreacted long-chain alcohols from the reaction mixture by is being carried out.

The long chain (fatty) alcohol is removed from the reaction mixture by one of the following methods: distillation or evaporation. When removed from the alkyl glycoside, polysaccharide byproducts and other less volatile substances remains in the product. .

The above polysaccharide by-products and The presence of other impurities may lead to the development of unacceptable properties (e.g. high viscosity), dark color and insoluble production of particulate matter and/or reaction mixtures using coated film or thin film evaporators. Fouling of heat transfer surfaces during the evaporative removal of unreacted fatty alcohols can occur.

Additionally, in some applications, alkyl glycosides with low content of non-alkyl glycoside materials may be used. A cid surfactant product is required. The method of the present invention involves the use of alkyl glycoside interfaces. Concentration of certain non-alkyl glycoside hydrophilic or water-miscible components in the active agent product can be used to reduce

The problem mentioned above is that the polysaccharide by-products and other hydrophilic compounds are first removed by water-immiscible solvents. By contacting the product in solution or the reaction mixture with water, the alkyl glycosyl Extracted from hydrophobic reaction mixtures containing cid surfactants or long-chain alcohols, and The resulting aqueous phase is then substantially removed by a method of separating it from the water-immiscible solvent phase. It was also discovered that it can be obtained.

That is, in one aspect, the present invention provides long-chain hydrophobic alcohols and/or glycans. Unwanted polysaccharides from hydrophobic substances containing polysaccharide substances mixed with lycoside surfactants This is an aqueous contact method for removing similar substances. This method involves the formation of a separate aqueous phase a sufficient amount of water and the hydrophobic composition (for the formation of a separate polysaccharide-rich aqueous phase). ) closely for a period of time sufficient to extract at least a portion of the polysaccharide material from the hydrophobic composition. The resulting polysaccharide-rich aqueous composition is then removed from the hydrophobic composition. It includes things. The present invention removes substantial amounts of polysaccharide by-products from a water-immiscible solvent phase. Preferably removed.

In another aspect of the invention, long chain alkyl glycosides, polyglycosides or or glycoside surfactant composition is dissolved in a water-immiscible solvent and contacted with water. Extracts water-immiscible substances in alkyl glycoside or alkyl polyglycoside products. put out Water is present in an amount that is at least sufficient to form a separate aqueous phase. Mizufu A miscible solvent is the alcohol from which the aglycone moiety of the glycosidic surfactant is derived. It can be.

In another embodiment of the invention, the aqueous solution of glycoside surfactant is immiscible with water. The glycoside surfactant is water-immiscible by contacting it with a compatible solvent for glycoside surfactants. Distribute into a compatible solvent. Hydrophilic impurities remain in the aqueous phase.

In another aspect, the invention provides: (a) Reacting a long-chain hydrophobic alcohol and a saccharide reactant at high temperature in the presence of an acid catalyst. to remove unreacted long-chain hydrophobic alcohols, glycoside surfactants, and polysaccharide byproducts. (b) producing a hydrophobic reaction product mixture comprising: (b) a neutralized reaction product mixture and water; and from about 1 to about 50 parts by weight of water per 100 parts by weight of the reaction product mixture. to extract at least a portion of the polysaccharide by-product from the reaction product mixture into water. The reaction product mixture is treated by contacting for a sufficient period of time and then separated. forming a polysaccharide-containing aqueous phase and a purified hydrophobic reaction product phase; (c) separating the polysaccharide-containing aqueous phase from the purified hydrophobic reaction product phase, and (d) Substantially all unreacted hydrophobic alcohol is then removed from the purified hydrophobic reaction product phase. remove the rule The present invention relates to a method for producing a glycoside surfactant comprising steps.

The method of the invention is substantially free of hydrophilic polysaccharide components and other hydrophilic impurities. a long chain hydrophobic alcoholic composition (or comprising at least a substantially reduced amount) provide a way to obtain Furthermore, the present invention satisfactorily provides a coated film type evaporator. can be processed from glycoside surfactants to hydrophobic alcohols. The melt is separated to provide a melt having a relatively lower viscosity than it would otherwise have. the presence and/or formation of insoluble particles is avoided during the evaporation process. Glycoside surfactant/long chain to avoid contamination (or carbonization) of the heat transfer surface of A means for obtaining a hydrophobic alcohol solution is also provided.

The above process is particularly universal for use, especially for those with an average of 9fl or more Hydrophobic alcohols having more (especially 10, 11 or more) carbon atoms and/or an average of 9 or more charcoals (especially 10, 11 or more) Effective when used with glycoside surfactants that have elementary atoms in their aglycone moieties. It is true. When used as such, this process an average of at least 9 (preferably at least an average of 10 or 11) carbons in atoms, and the average degree of polymerization is small (both are 1.2, and the total glycoside surfactant 0.5% by weight or less (preferably 0.25% by weight or less, more preferably 0.25% by weight or less, based on weight) 0.1% by weight or less, most preferably 0.01% by weight or less) hydrophilic polysaccharide component and a degree of polymerization of 5% by weight or less (preferably 1% by weight or less) of 10 or more. Provided are novel glycoside surfactant compositions comprising polyglycoside species.

According to the present invention, solutions of long-chain hydrophobic alcohols that can be suitably prepared and/or Glycoside surfactants that can be suitably treated or purified by Formula: RO(R'O), (Z), (A) [wherein the hydrophobic aglycone substituent R is 8 to 30 (preferably 10 to 24, more preferably 10 to 18) carbon g atoms ) containing monovalent organic groups (e.g., alkyl, hydroxyalkyl, alkenyl, Roxyalkenyl, 7aryl, alkylaryl, hydroxyalkylary monovalent, such as aryl, arylalkyl, alkenylaryl, arylalkyl, etc. saturated aliphatic, unsaturated aliphatic or aromatic group), O is an oxygen atom, R1 is a carbon atom 2% hydrocarbon groups containing 2 to 4 (preferably -R1 (1- group is ethylene oxide) , propylene oxide, or random or block combinations thereof ), y is a number with an average value of O to 12 (preferably y is O), 2 is a number with up to 5 carbon atoms. or 6 reducing substances (e.g., glucose, fructose, mannose, galactose). Coutose, gulose, gulose, allose, aldose, idose, arabino groups derived from cosyl group), and X represents the average degree of polymerization, P, with an average value of 1 to 5 (preferably is a number from 1 to 3). ].

Particularly preferred glycoside surfactants include those in which the glycodyl group Z is arabinose, xylo glucose, mannose, galactose or mixtures thereof (especially glucose) The aglycone group R has about 10 to about 18 carbon atoms (specifically about 12 to about 18 monovalent aliphatic groups, and the average value of X is about 1,1 to 25 ( In particular, it includes compounds where 1, 2 to 1°8).

This treatment or purification method is suitable for relatively more hydrophobic glycoside surfactants (e.g. For example, the hydrophobic aglycone group R contains at least 11 or 12 carbon atoms, with an average degree of polymerization X of about 1.5 or less (i.e. , carried out on them) and should be treated as such is a hydrophobic alcoholic solution containing relatively small amounts of glycoside surfactant solids (e.g. Preferably, the glycoside surfactant is about 5 to about 40° of the hydrophobic alcoholic solution. from about 5% to about 35%, more preferably from about 5% to about 30% by weight). It is particularly efficient and effective when In fact, comparing the above processing or purification methods, in combination with less hydrophobic glycoside surfactants and/or at higher concentrations. glycosidic surfactants (i.e., containing higher amounts of glycosidic surfactant solids) It can be suitably used in combination with a glycoside interface. The loss (i.e. partitioning or dissolution) of activator into the resulting separated aqueous phase is slightly increased. less desirable in that it involves or is characterized by

The novel glycoside surfactant compositions that can be prepared according to the present invention have hydrophobic On average there are at least 9 aglycone substituents R, preferably at least 10 or 11 carbon atoms), and the average degree of polymerization (i.e. the average value of X) is small (both 1 ．． 2, and 0.5% by weight or less (preferably is 0.25% by weight or less, more preferably 0.1% by weight or less, most preferably 0. 01% by weight or less) and hydrophilic polysaccharide components of 5% by weight or less (preferably 2% by weight or less) 4-506338 (6) % by weight or less, more preferably 1% by weight or less) of polyglycoside species [degree of polymerization (i.e., That is, it corresponds to formula (A) except that the value of X of each molecule is 10 or more. It is a substance that contains a chemical compound. Generally, the glycoside surfactant component (A) is It accounts for the major weight proportion (i.e. 50% or more) of the composition and is often the component ( A) is at least 90% by weight of the composition (more preferably at least about 93% by weight) %, most preferably at least about 95% by weight).

In a further aspect of the invention, the above-mentioned long-chain alkyl glycosylation containing hydrophilic impurities is provided. surfactant products (few alkyl groups (both containing 8 carbon atoms) are water-immiscible solvent or alkyl glycoside surfactant in the presence of a suitable amount of water. Water separated from a separate phase, a water-immiscible solvent phase, by dissolving or extracting it in an aqueous solvent Alkyl glycoside surfactants recovered from phases and water-immiscible or hydrophobic solvents It can form a sex agent.

The water-immiscible solvent is the same hydrophobic alcohol or alcohol in which the aglycone group is formed. Hydrophobic alcohols such as toluene, xylene, di-n-butyl ether and It may be a solvent such as perchlorethylene or perchlorethylene. Aluminum after contacting the mixture with water The water-immiscible solvent has a low boiling point so that it can be easily separated from the kill glycoside composition. It is preferable to have.

The separated aqueous phase contains water-soluble or hydrophilic impurities (e.g. catalyst salts) and certain Contains dissolved alkyl glycoside substances. Alkyl glycoside substances are primarily It is an alkyl glycoside substance having a high degree of concentration, that is, a high value of X in the above formula.

This allows long-chain hydrophobic alcohols to be used to prepare the glycoside surfactants described above. preferably 8 to 30 pieces (preferably 10 to 24 pieces, more preferably 10 to 18 pieces, Most preferably m aliphatic alcohols containing 12 to 18 carbon atoms.

Saccharide reactants that can be used for the preparation of the above glycoside surfactants include, for example For example glucose, galactose, mannose, xylose, arabinose and Reduced monosaccharide substances containing 5 to 6 carbon atoms, such as fructose, and By water splitting, lower alkyl glycosides (e.g. methyl glycoside, ethyl glycoside) monosaccharides, oligosaccharides such as glycosides, propyl glycosides, butyl glycosides, etc.) Sugars [(e.g. sucrose, maltose, maltotriose, lactose, robiose, melibiose, cellobiose, raffinose, stathiose, etc.) and polysaccharide-forming substances such as starch. Such sugar reactants are It can be used in a dry (e.g. anhydrous) state or, if desired, as an aqueous solution thereof. can be done.

Hydrophobic alcohol reactants and saccharide reactants to form glycoside surfactants The reaction is typically carried out at elevated temperatures in the presence of an acid catalyst. Generally, this reaction is Preferably carried out at a temperature of about 80 to about 160°C, more preferably about 90 to about 12°C. It is carried out at a temperature of 0°C.

Acid catalysts preferably used here include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and hypophosphorous acid. Strong mineral acids such as para-toluenesulfonic acid, methanesulfonic acid, trifluorometa mono- or polyalkylene sulfonic acid, dodecylbenzenesulfonic acid, etc. organic acids such as aryl mono- or polysulfonic acids, and macroreticular polymers. Giant network acid ion exchange resins such as sulfonic acid ion exchange resins and perfluorosulfonic acid resins Contains exchange resin. Such acidic catalysts typically have a amount of 0.0005 to 0.03 mol (preferably 0.002 to 0.015 mol) used in

The reaction between the saccharide reactant and the alcohol reactant according to the present invention is characterized in that the alcohol molecule is is a condensation reaction in which a water molecule is released or generated in each case when it reacts with a molecule of sugar . Since such reactions are reversible, equilibrium is typically It is desirable to remove water from the reaction mixture during the reaction in order to transfer it to the product.

Reactions are usually carried out at pressures that facilitate water removal while simultaneously maintaining the desired reaction temperature. It is carried out completely. Generally, the reaction is carried out at 1-100 mmHg (preferably 10-5 Qa It is advantageously carried out at a pressure of (v+Hg x absolute pressure).

Typically, the reaction process described above is carried out for 1 to 20 hours (preferably 2 to 10 hours). be exposed.

The amount of undesirable polysaccharide by-products generated during the reaction process is determined by 6338 (7) For example, the nature or type and purity of the alcohol and sugar reactants used; the catalysts selected and the reaction conditions used, the control and conduct of the ongoing reactions; the degree of care taken in the average degree of polymerization of the glycoside surfactant product to be produced; (D, P, X, i.e. the average value of rxJ), etc. Ru. However, in general, the amount of undesirable polysaccharide by-products generated is increase in the average glycoside surfactant product, P, (i.e., the average rxJ value) and It can be noted that both increase gradually. Medium glue.

Relatively pure reactants and well-performed and carefully controlled reaction sites with carefully selected catalysts. Even in cases where the amount of polysaccharide by-products varies as a function of P, It can be expected that: the amount of polysaccharide by-products generated Average, P, (wt%, based on glycoside surfactant weight) 1.1 at least Approximately 0.6% 1.2 At least about 1.2% 1.3 At least about 1.8% 1.4 At least about 2.4% 1.5 At least about 3.0% 1.6 At least about 3.6% At the end of the reaction, neutralize the acid catalyst (e.g. in the case of an insoluble acidic ion exchange resin) can be removed from the reaction mixture (by centrifugation or filtration). or If the catalyst is a substantially water-soluble material, during the aqueous extraction process described below, the following removal leaving it in an unneutralized state (i.e. with undesirable polysaccharide by-products) for removal Can be done.

In this latter case, the extraction/separation operation is preferably carried out to minimize hydrolytic back reactions. It is carried out under relatively low temperature and short time conditions in order to maintain the temperature.

As already mentioned, an important feature of the present invention is that the aqueous contacting procedure enables the preparation of hydrophobic compositions (e.g. For example, long chain hydrophobic alcohol compositions, the above sugar reactant/hydrophobic alcohol reaction products Mixed long-chain hydrophobic alcohol/glycoside surfactants such as crude process reaction products glycoside surfactant compositions, and solutions of glycoside surfactant compositions). It consists in removing similar substances.

According to the method of the invention, a hydrophobic composition is an amount of water sufficient to extract at least a substantial amount of the unwanted polysaccharide material from the product; The hydrophobic composition is contacted for a sufficient period of time (preferably repeatedly) to obtain The aqueous phase is then separated from the hydrophobic composition.

Naturally, the amount of water used in the foregoing procedure will vary from the hydrophobic composition to the desired amount or is controlled or adjusted to be sufficient to remove the proportion of water-soluble substances, and sufficient to cross the aqueous saturation point of the hydrophobic composition and form a separate aqueous phase. Must be. Typically, the amount of water used is 100 parts of hydrophobic composition. water to about 1 to about 50 (preferably about 2 to about 40, more preferably about 2 to about 3 0) parts by weight.

In a preferred embodiment of the invention, the aqueous contacting procedure comprises: 10 to 40 (preferably 20 to 30) parts by weight of water in the polysaccharide-containing hydrophobic composition 10 0 parts by weight and in the second aqueous contacting step between 5 and 25 (preferably 10-20) parts by weight of water is used per 100 parts by weight of the hydrophobic composition. In particular, it is carried out as a two or three stage) process. Alternatively, centrifugation countercurrent Extraction/separation techniques can be used.

The temperature and pressure conditions under which the above aqueous contacting operations are carried out are not particularly critical, but typically , the contact is carried out at a temperature of 25-120 (preferably 45-90) °C and 600-100 °C. It is carried out at a pressure of 0 (preferably 700-900) mmHg (absolute pressure).

The time for which the aqueous contact/separation operation is carried out is not particularly critical, but typically ranges from 1 to 18 (preferably 2 to 8) hours. In the case of centrifugal countercurrent method, seconds are sufficient. I understand.

Separating the aqueous phase from the hydrophobic composition following the contacting process described above may include, for example, Separate the two phases into upper and lower layers and then separate one layer from the other (e.g. by tilting separation (by filtration, draining one layer, etc.) or using centrifugation. It can also be carried out by any convenient conventional method. However, one In a particularly preferred embodiment, the extraction and separation steps are continuous using countercurrent centrifugation. Do it on a regular basis (or semi-continuously).

Examples of polysaccharide-containing hydrophobic compositions that can be suitably treated by the above process include For example, long-chain hydrophobic alcohols, relatively water-insoluble glycoside surfactants, and hydrophobic alcohols. Hydrophobic substances such as alcohol/glycoside surfactant solutions and water-immiscible solvent solutions including any composition having a water-soluble polysaccharide component dispersed or dissolved in the water-soluble polysaccharide component.

Hydrophobic compositions suitably treated according to the present invention are particularly characterized by ( a) 95 to 50 (preferably 90 to 60) parts by weight of a long chain hydrophobic alcohol or a water-immiscible solvent, (b) 4 to 45 (preferably 8 to 35) parts by weight of a glycoside world; a surfactant, and (c) 0.5 to 10 (often 1.0 to 8) parts by weight of any of the above. Compositions comprising saccharide substances are included.

As already mentioned, the method of the present invention initially includes in the hydrophobic composition of interest Particularly effective in removing bulk quantities of polysaccharide substances. i.e., for example, hydrophobic composition If the product initially contains from about 1 to about 10% by weight of polysaccharide material, based on total weight, The polysaccharide content is preferably below 1% by weight based on the total weight according to the extraction process. 0.3% by weight or less, more preferably 0.1% by weight or less) be able to.

During the process described above, the hydrophobic composition is treated or treated with a glycoside surfactant. Water-immiscible solvent solutions are naturally saturated with small amounts, typically trace amounts, of water. prescribed In an example, the exact quantitative amount of water absorbed into a hydrophobic or water-immiscible composition is Absorption depends on the nature, type, degree of hydrophobicity and temperature of the particular composition involved. The amount of water extracted is typically no more than about 25% (by weight) of the extracted hydrophobic composition. (typically less than about 151 i%). Water-immiscible solvents and process temperatures should be chosen to minimize the amount of water absorbed.

If desired, a small amount of water can be left in the extracted hydrophobic composition (if water removal is necessary). If necessary, they can be easily and conveniently removed by evaporation in a thin film extractor. can. Operating conditions for thin film evaporators for water removal purposes typically range from about 50 to a temperature of about 250°C (preferably about 130°C to about 220°C) and a temperature of about 100°C to about 1 000 (preferably about 200 to about 760) mmHg (absolute pressure).

It is preferable to operate at relatively high temperatures to avoid foam formation during the water removal process. Yes.

The hydrophobic composition comprises a glycoside surfactant (e.g., a glycoside surfactant). containing long-chain hydrophobic alcohol solutions (such as reaction products obtained from the preparation process). Separation of long-chain hydrophobic allules from glycosidic surfactants It is often desirable to do so. Separation is typically carried out using a thin film evaporator at approximately 1 An operating temperature of 30 to 300°C (preferably about 150 to about 250°C) and about 0.1 Conveniently carried out at a pressure of ~30 (preferably about 1 to about 15) mmHg (absolute). I can.

As mentioned above, this method eliminates unacceptable soiling or alcohol without carbonization and without the formation of insoluble particles during the evaporation procedure. can be processed in a thin film evaporator to separate the surfactant from the surfactant. The fact that a glycoside surfactant/long-chain hydrophobic alcohol solution can be obtained is due to the present invention. Benefits and advantages of Ming.

Naturally, the glycoside surfactant products produced according to the present invention can be used in any of a wide variety of It can be used suitably for household, industrial, cosmetic and agricultural purposes, and the produced raw materials Commercial glycoside surfactants are already known to be useful and have applications. . Typically, the glycoside surfactant is about 30 to about 70% by weight based on the total weight of the aqueous solution. % (preferably from about 40 to about 60% by weight) of glycoside surfactant. Produced and sold as an aqueous solution.

The present invention will be explained in more detail using the following examples. All parts unless otherwise specified and percentages are by weight; all temperatures are in °C.

Example 1 Anhydrous dextrose and C1! , cps and CI4 alcohol mixture. Strauss:alcohol weight ratio is about 6, temperature is about 105℃, about 1 mol% ( The reaction was carried out for about 8 hours in the presence of a para-toluenesulfonic acid catalyst (based on dextrose). 01□-1 having the composition shown in Table A below, in an alcohol mixture. A solution containing CI2-I and alkyl glycoside (average degree of polymerization, P approximately 1.4) was added to The reaction was followed by neutralization to pH approximately 7 using an aqueous sodium hydroxide solution. profit 100 parts by weight of the reaction mixture was stirred at a temperature of 60° C. and under a pressure of 735 mmHH. Stir and add 2 parts by weight of water to the stirred reaction mixture. Next, the resulting water-containing mixture is The temperature was increased to 105°C and maintained at that temperature for 30 minutes, during which time the reaction mixture A solid substance formed in the material. Solid material is removed from the mixture by filtration and analyzed It was found that it had the composition shown in column C of Table A. When the filtrate was also analyzed, Table A showed It was found that it had the composition shown in column B.

The resulting filtrate was stirred at a temperature of 105°C and a pressure of 735 mmHg, and the pressure was reduced to The temperature was gradually lowered to 3QmmHg over 40 minutes, and the filtrate was kept under that condition for 20 minutes. Water was removed by maintenance. The obtained dehydrated filtrate has the composition shown in Dl [in Table A]. I found out.

The dehydrated filtrate was poured into Leybold-Heraeus! ! ! ! Concentrated using a cloth membrane evaporator (at a temperature of 205°C and a pressure of 1 mmHg (absolute)). Most of the unreacted CI2-14 alcohol was removed by condensation. Obtained concentrated CI The 2-14 alkyl glyconde product may have the composition shown in Ell of Table A. Understood.

Drying substance polydextrose A41I of dextrose! The value of and the value of column B As can be seen by comparison, the aqueous contact operation trose by more than 2.5 times (i.e. 9.76% to 3.60% by dry matter weight) %).

In this example, at 80° C., the initial hydrophobic composition is shown in Table B below. 1212 parts of water (i.e., 30 parts of water per 100 parts of hydrophobic composition) (i.e., with vigorous shaking). DeLaval chestnut With a system separator [GYROTEST type, 3450 rpm], At 80° C., the separated aqueous fluid phase formed was separated from the hydrophobic phase.

The clear hydrophobic top layer is collected from the cream separator and mixed with a second portion of deionized water (hydrophobic 15 parts of water per 100 parts of the composition) and mixed intimately again (this time at 70°C). The resulting mixture was separated using the cream separator described above.

The obtained second hydrophobic upper layer was collected, and at 60°C, 1 part by weight per 100 parts by weight of the hydrophobic phase was collected. Mix vigorously with 5 parts by weight of deionized water and cream the resulting aqueous and hydrophobic phase. They were separated from each other by a separator.

Analysis of the resulting hydrophobic top layer (contacted twice with water) reveals 10.4% by weight of absorbed water. It was found to contain (1G) Dehydration was performed at 210° C. under atmospheric pressure using a film evaporator.

The resulting dehydrated composition was then evaporated using a Reybord-Herois evaporator to remove most of the long-chain alcohol. It was concentrated at 200° C. under a pressure of 1 mmHH to remove coal components. obtained Reverse phase liquid chromatography (RPLC) of evaporated glucoside surfactant products The approximate composition measured by the method is shown in Table B below. As can be seen from the results shown in this table. In the initial hydrophobic glycoside surfactant/unreacted long chain alcohol reaction mixture, polar substances (i.e. salts, catalysts, dextrose and polydextrose) ) is removed during the three-step contact process.

Be international search report 1++eun+n*+l^”””AII’PCT/EP89101556 International Coordination inspection report

Claims (31)

[Claims] 1. Glycosidic surfactants, hydrophobic water-immiscible substances containing from 8 to 30 carbon atoms Alcohol, glycoside surfactant phase solvent and water; water is the glycoside surfactant phase solvent. less than 50% by weight of active substance and solvent to form a separate water-containing phase. be present in sufficient quantity so that at least some of the hydrophilic substances at the glycosidic interface The contact time should be sufficient for separation from the activator and the water-containing phase should be separated from the solvent phase. A method for removing hydrophilic substances from a glycosidic surfactant comprising separating . 2. The solvent phase comprises at least one aliphatic monohydric alcohol containing from 8 to 30 carbon atoms. 2. The method of claim 1, comprising one. 3. The solvent phase is (a) 95 to 50% by weight, based on the total weight of the composition before contact with water; % long chain hydrophobic alcohol, (b) 4-45% by weight glycoside surfactant and and (c) 1 to 10% by weight of a polysaccharide material. 4. The solvent phase is at least an aliphatic monohydric alcohol containing 10 to 24 carbon atoms. 4. The method according to any one of claims 1 to 3, further comprising one type. 5. Glycoside surfactants are Formula: RO(R1O)y(Z)x(A) [In the formula, R is a monovalent organic group containing 8 to 30 carbon atoms, O is an oxygen atom, and R1 is 2 a divalent hydrocarbon group containing ~4 carbon atoms, y is a number with an average value of 0 to 12, Z is a group derived from a reducing sugar containing 5 or 6 carbon atoms, and x is 1 to 5 represents a number with an average value of ] 2. The method according to claim 1, comprising at least one compound represented by: 6. in the glycosidic substance (A), R is a monovalent aliphatic group containing 10 to 24 carbon atoms; , y is 0 and x represents a number having an average value of 1 to 3. 7. The method according to claim 1, wherein 1 to 50 parts by weight of water is brought into contact with 100 parts by weight of the solvent phase. Law. 8. The solvent phase initially weighs between 0.5 and 8 weight based on the total weight of the solvent phase before contacting with water. % polysaccharide by-product. 9. The solvent phase, after contact with water, contains no more than 0.3% by weight based on the total weight of the solvent phase composition. 9. The method of claim 8, comprising a polysaccharide by-product of. 10. A method according to claim 1, carried out at a temperature in the range of 25 to 120<0>C. 11. The test is carried out by contacting the polysaccharide-containing solvent phase with water for 0.01 to 18 hours. The method described in claim 1. 12. (a) Reacting a long-chain hydrophobic alcohol and a sugar reactant at high temperature in the presence of an acid catalyst. Correspondingly, unreacted long-chain hydrophobic alcohols, glycoside surfactants and polysaccharide adjuncts are producing a hydrophobic reaction product mixture containing an organism; (b) Neutralize the reaction product mixture, and add the neutralized reaction product mixture and water to an amount of water. polysaccharide by-product, with 1 to 50 parts by weight based on 100 parts by weight of the reaction product mixture. in the water for a sufficient period of time to extract at least a portion of the reaction product mixture from the reaction product mixture. The reaction product mixture is treated by contacting the reaction product mixture, thereby separating different forming a polysaccharide-containing aqueous phase and a purified hydrophobic reaction product phase; (c) a purified hydrophobic reaction product phase; separating the polysaccharide-containing aqueous phase from the product phase; and (d) Then remove unreacted long-chain hydrophobic alcohol from the purified hydrophobic reaction product phase. do A method for producing a glycoside surfactant, comprising: 13. The long chain hydrophobic alcohol is a monohydric aliphatic alcohol containing 8 to 30 carbon atoms. 13. The method according to claim 12, wherein 14. A claim in which the saccharide reactant comprises a reduced monosaccharide containing 5 or 6 carbon atoms. The method according to item 13. 15. Saccharide reactants and long-chain hydrophobic alcohols for the preparation of glycosidic surfactants The reaction with 15. The method according to claim 14, which is carried out in. 16. The hydrophobic reaction product formed in step (a) is based on the total weight of the composition (a ) 95-50% by weight long chain hydrophobic alcohol, (b) 4-45% by weight glycosidic and (c) 1 to 10% by weight of a polysaccharide by-product. How to put it on. 17. 13. A method according to claim 12, wherein step (b) is carried out at a temperature of 25 to 120<0>C. 18. Claim 12, wherein the separation of step (c) and step (b) are carried out in a countercurrent centrifuge. Method described. 19. The water-immiscible solvent comprises an unreacted long-chain hydrophobic alcohol and is glycoside surfactant products using a thin film evaporator operated under reduced pressure. 2. The method of claim 1, wherein the method is removed from 20. Thin film evaporator 20. The method according to claim 19, wherein the method is operated at a pressure of (counterpressure). 21. Monohydric aliphatic alcohols in which the long chain hydrophobic alcohol contains 10 to 24 carbon atoms 21. The method according to claim 20, wherein 22. The hydrophobic reaction product mixture of step (a) is from 1.5 to 8, based on the total weight of the composition. 13. The method of claim 12, comprising % by weight polysaccharide by-product. 23. After contact with water and separation therefrom of the resulting polysaccharide-containing aqueous phase, hydrophobic The reaction product mixture contains no more than 0.3% by weight of polysaccharide by-products based on the total weight of the composition. 23. The method of claim 22, comprising: 24. The produced glycoside surfactant has the formula: RO(R1O)y(Z)x(A ) [In the formula, R is a monovalent organic group containing 8 to 30 carbon atoms, O is an oxygen atom, and R1 is 2 a divalent hydrocarbon group containing ~4 carbon atoms, y is a number with an average value of 0 to 12, Z is a group derived from a reducing sugar containing 5 or 6 carbon atoms, and x is 1 to 5 represents a number with an average value of ] 13. The method according to claim 12, wherein the compound is a compound represented by: 25. In the glycoside surfactant (A), R contains 10 to 24 carbon atoms. 24. A monovalent organic group comprising: y is 0 and x is a number having an average value of 1 to 3; How to put it on. 26. (a) Formula: RO(R1O)y(Z)x(A) [wherein, R is 8 to 30 carbons] a hydrophobic aglycone substituent comprising a monovalent organic group containing an elementary atom; O is an oxygen atom; R1 is a divalent hydrocarbon group containing 2 to 4 carbon atoms, y has an average value of 0 to 12 , Z is a group derived from a reducing sugar containing 5 or 6 carbon atoms, and x represents a number having an average value of 1 to 5. ] The glycoside surfactant molecule is (b) the total average value of x is at least 1.2, and as the total average value, the hydrophobic aglycone substituent R contains at least 9 carbon atoms; Hydrophilic polysaccharide component of 0.5% by weight or less based on the total weight of surfactant and 5% by weight Glycoside species (A) containing polyglycoside species (A) in which individual x of % or less is greater than 10 Cocidal composition. 27. The hydrophobic aglycone substituents R contain on average at least 10 carbon atoms. 27. The composition of claim 26, comprising: 28. The composition contains no more than 0.25% by weight of parent based on the total weight of glycoside surfactants. 27. The composition of claim 26, comprising an aqueous saccharide component. 29. A polyglycoside surfactant species (A) in which each x is larger than 10 27. The composition of claim 26, comprising up to 2% by weight. 30. Claim 26 wherein the glycoside surfactant represented by (a) accounts for the total weight of the composition. 27. A composition according to claim 26, comprising at least 90% by weight. 31. Water-immiscible solvents include aromatic solvents, chlorinated solvents and water-immiscible alcohols. The method according to claim 1, comprising at least one selected from the group consisting of: