• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The present invention relates to an improved method for producing sophorolactone, to compositions comprising sophorolactone obtained by this method, and to use of the sophorolactone. In particular, the invention relates to new compositions for hard surface cleaners.
    公开号:BE1019942A3
    申请号:E2012/0386
    申请日:2012-06-06
    公开日:2013-02-05
    发明作者:Dirk Develter；Steve Fleurackers；Mark Renkin
    申请人:Ecover Belgium N V；
    IPC主号:
    专利说明:

    • IMPROVED SOPHOROLACTON COMPOSITIONS, PREPARATION METHOD AND USE
    The present invention relates to an improved method for producing sophorolactone, to compositions comprising sophorolactone obtained by this method, and to use of the sophorolactone. In particular, the invention relates to new compositions for hard surface cleaners.
    Sophorolipids are sufficiently known as surfactants that can be produced through microbial cultivation. Sophorolipids are interesting as they are derived from renewable resources and are biodegradable after use. Known methods have the disadvantage that mixtures are of various forms, mainly acid (I) and lactone forms (II) as depicted. The R groups depicted are hydrogen or an acetyl group. The chain length n is 2 to 16 carbon atoms. A typical chain length is 16 to 18 chain lengths; that is. n = 1315.
    The ratio in which both forms occur can indeed be controlled in function of the substrate choice for the microorganism and the fermentation conditions. But the production of a composition with a specific desired ratio is difficult. Since properties and functionalities of the sophorolipid forms vary depending on the nature and ratio of the homologues present, further product development is considerably more difficult and complicated.
    The lactone form (II) of sophorolipids has been documented as the most active, both in terms of surface tension reduction and antimicrobial activity.
    But this shape is not easy to isolate. For example, it is known that acetyl bonds in sophorolipids are chemically unstable and easily hydrolyze on heating. Alkaline solutions should also be avoided since these conditions lead to the formation of the fully deacetylated acid form.
    Consequently, there is still a need in the industry for improved sophorolactone production processes, with improved selectivity for sophorolactone, easy to apply, economically viable and environmentally friendly, in particular without the use of organic solvents.
    Methods for the isolation of either the acid or lactone form were studied. EP209783 for example describes a process in which an alcohol extraction is applied. This process is very time-consuming and costly. Moreover, an organic solvent extraction does not fit into the ecological story of biosurfactants, which includes sophorolipids.
    It is the object of the present invention to provide an improved sophorolactone synthesis suitable for isolating sophorolactone without having to resort to organic solvents and complex cleaning or purification methods and suitable for use as an active substance in cleaning agents , in particular hard surface cleaning products.
    This object is achieved with the technical features of the characterizing part of the first claim.
    With the present invention, it has been surprisingly found that production of an oil-free preculture, keeping fatty acid below a guide value, both by controlling substrate supply and fermentation levels, direct the process to selective formation of the lactone form. Since little acid is present to keep the lactone in emulsion, crystal growth is promoted and the lactone can be easily isolated from the aqueous solution.
    The lower presence of the acid sophorolipid form further has the advantage that the mixture foams less. Foam control is facilitated, even to the extent that anti-foaming additive becomes unnecessary. This is an additional advantage, since these means are difficult to remove. The reduced foaming also has the advantage that more of the reactor volume can be occupied by the reaction mixture. Less space needs to be provided for foaming.
    Preferably the method is used using the best known sophorolipid producing microorganisms Candida bombicola or Candida apicoia. Alternatives can be provided by Candida bogoriensis, Candida batistae and Wickerhamilella domercqiae.
    The method starts by pre-cultivating Candida bombicola or Candida apicola cells in the absence of an oily substrate until a stationary growth phase is reached. This turned out to be advantageous to increase the sophorolactone yield.
    A fermentation step then takes place. Hereby a reaction mixture of water, pre-culture cells, a sugar and a substrate metabolizable by the cells is brought together in an amount and under conditions, so that the cells metabolize the sugar and substrate. Sophorolactone and fatty acid are thereby formed.
    Carbohydrates are selected as sugar that can be assimilated by Candida species. Sugars suitable for use in the invention are glucose, sucrose and raffinose.
    Furthermore, the substrate is supplied to the cells so that fatty acid levels are kept below a predetermined level. For Candida bombicola this was set at a minimum of 10 g / l. The threshold value is preferably below 8 g / l, preferably between 1-5 g / l, expressed in weight of acid per liter of reaction mixture. If the formation of fatty acid and the fatty acid content in the reaction mixture are kept below this limit value, at least a part of the sophorolactone formed in the reaction mixture will crystallize.
    In a preferred form, the substrate is a triglyceride; preferably a triglyceride of saturated or unsaturated fatty acids with 16 or 18 carbon atoms; preferably a vegetable oil, most preferably rapeseed oil.
    The substrate is preferably supplied to the reaction mixture in a continuous manner. More preferably, a so-called "fed-batch" system is used. This has the advantage that the nutritional environment required for the fermentation can be kept approximately constant during the course of a reaction batch.
    Furthermore, it is advantageous to provide a heating step in which the reaction mixture is heated to a temperature of 60 ° C-90 ° C, preferably 70 ° C. This melts the present sophorolactone crystals. The yeast cells are killed at this temperature, so that the temperature step has a pasteurization effect.
    The molten sophorolactone is allowed to sediment, then it is easily removable from the reactor. It is sufficient to remove the lower phase from the reactor. The separation of this crude sophorolactone composition and removal from the reactor proceeds without using an organic solvent.
    The inventors further developed a method to further increase the sophorolactone content in the composition. Again, no organic solvent was used. Tevèns did not have to resort to complex purification techniques, such as chromatography, which are difficult to apply on an industrial scale. The resulting product is free from traces of organic solvent.
    A method according to an embodiment of the invention has the advantage that it is easy and simple to implement. It results in less complex sophorolipid mixtures than methods of the prior art. An advantage is the higher yield of sophorolactone. Suppressing the fatty acid content has the effect that no emulsion is formed and the lactone form does not go into solution.
    Dry sophorolactone, so substantially free of water, is obtained as follows. The crude sophorolactone composition, which was left warm from the reactor, is cooled until a solid forms. Due to the presence of water in the crude product, it is typically in the form of a paste.
    The solid is then dispersed in water at a temperature of 5 ° C-25 ° C, preferably 10 ° C-15 ° C, more preferably 10 ° C. Expressed in weight percent, a water to solid ratio of 0.5-15 is used. The choice of this amount of water ensures that sophorolipids present in acid form dissolve well as opposed to sophorolipids present in lactone form. The poor water solubility of the lactone form is enhanced at a lower temperature. The lactone present crystallizes. The result is an aqueous dispersion of sophorolactone crystals.
    Descaled water is preferably used. Calcium ions present in the water would otherwise form calcium salts with the sophorolipids present in acid form. This is undesirable since it makes valorisation more difficult.
    Water and crystals are separated, for example by decantation or centrifugation. The dispersion and separation step are preferably repeated several times, preferably up to 10 times. It is important that a temperature below 40 ° C, preferably 30 ° C, is maintained. This has the consequence that the lactone present does not melt. Keeping the lactone in crystal form has the advantage that the separation of acid and lactone form is easy and smooth and the amount of water in the lactone is reduced to a minimum.
    The resulting sophorolactone composition is then dried to remove the remaining water. The composition can be dried by spray drying, drum drying, convection drying, thin film evaporation, vacuum drying, flaking, extrusion or casting. The result is a dry sophorolactone, substantially free of water.
    The substrate preferably is corn steep liquor, a triglyceride, isostearic acid, isostearic alcohol, or a protected ester of formula H- (CH2) n-O-CO- (CH2) m-COOH with a carbon chain length (n + m + 2) from 16-18. A more detailed description of the protected esters can be found in EP1953237.
    Corn steep liquor, a by-product from the corn starch industry, is preferably used as a substrate.
    In a preferred form of a method according to the invention, the Candida species is Candida bombicola mutant strain M18, M30 or M33; preferably Candida bombicola M30. These microorganisms have been modified and provide a further increase in sophorolactone production.
    Preferably, the residual substrate content in a composition obtained according to the method is less than 1 weight percent. The term residual substrate means the sum of non-metabolized substrate and metabolites with the exception of the sophorolipids themselves; so triglycerides, fatty acids, fatty alcohol, fatty acid methyl esters.
    Most preferably in a composition, a residual content is less than 0.2 weight percent fatty acid. The availability of a low residual fatty acid sophorolactone provides access to new formulations.
    The dry form can be used advantageously in dishwashing and washing formulas in tablet or powder form. Standard tablets or powder typically have a basic pH, around pH 10.
    In the prior art, for example EP1411111, the addition of a liquid sophorolipid mixture to an alkaline powder is described. Such compositions are not stable as they spontaneously hydrolyze in the presence of water to sophorolipids in acid form. Moreover, these acids are known for their increased foaming behavior with respect to sophorolipids in lactone form. As a result, a formulation that is expected to be low-foaming will, in time, show a higher than expected foaming when used. This is especially undesirable in formulas where foaming should be limited, such as in powders and tablets for dishwashers and washing machines. Dishwashers and dishwashers are characterized by frequent mechanical actions. Applied to a foam-forming formulation, foam formation is thereby encouraged. Abundant foam formation can lead to device blockages. Consequently, it is desirable to have low-foaming compositions that retain their foaming behavior over time.
    A dry one. Sophorolactone composition obtainable with an embodiment of the method according to the invention satisfies this. She . is characterized by a reduced sensitivity to hydrolysis and thus improved storage stability. Addition to a standard tablet or powder form yields products that retain their foaming behavior over time.
    Preferably, the composition in tablet or powder form comprises the following dry sophorolactone composition: 70-100% by weight of sophorolactone, 0-1% by weight of sophorolipid acid, and less than 0.2% by weight of fatty acid. The composition is characterized by a pH 8.0-14.0 measured on a 1% aqueous solution of the composition.
    The limited water solubility is characteristic of sophorolactone. This limits the usability in liquid formulations. To this end, the invention provides a solution by providing a solution-enhancing agent, in particular sophorolipid acid obtained by hydrolysis of a sophorolactone composition according to an embodiment of the invention.
    In a third aspect, the invention provides a method for preparing a partially hydrolyzed, sophorolactone composition. To this end, one starts from a sophorolactone composition with the following composition: 70-100% by weight of sophorolactone, 0-1% by weight of sophorolipid acid, and less than 0.2% by weight of fatty acid. This composition is available with a method according to an embodiment of the invention, as previously described. 0.5 to 1.0 equivalent of base is then added to this composition. This results in a sophorolipid mixture in which the sophorolactone present at the start was partially hydrolysed to sophorolipid acid. In other words, a partially hydrolyzed sophorolactone composition.
    This method has the advantage that it provides easy access to compositions with a predetermined lactone / acid ratio. Consequently, the foam behavior of a formulation can be tuned. The acid form improves the solubility of the present lactone form.
    In a preferred form, 0.6-0.7 equivalents of base are used for the hydrolysis. These compositions show the largest decrease in.
    surface tension and are therefore interesting for use in detergent formulations.
    The partial hydrolyzate is preferably rich in the sophorolactone form, most preferably of the total amount of sophorolipids present in the hydrolyzate, 39% -45% sophorolipidic acid and 61% -55% sophorolactone, expressed as a weight percentage relative to the total amount of sophorolipids in the composition. At the same time, less than 0.2% by weight of fatty acid is present, expressed as a percentage by weight of the total composition.
    In a further aspect, the invention provides some uses.
    Preferably a composition according to a preferred form of the invention is used as a surface, active substance in a composition for cleaning hard surfaces selected from a window cleaner, a tile cleaner, a degreaser, a dishwasher product and WC cleaner. This has the advantage that in existing formulations one or more surfactants can be replaced by a surfactant with a better ecological profile.
    Preferably a composition according to a preferred form of the invention is used, as a foam-breaking agent for one or more non-glycolipid surfactants in a detergent composition selected from a window cleaner, a tile cleaner, a degreaser, a dishwasher product and washing machine product. Research has shown that sophorolactone in combination with one or more non-glycolipid surfactants produces a foam behavior in which initially sudden rising foam is formed followed by a rapidly decreasing foam. This is advantageous since on the one hand it gives the consumer an indication of the product. was actually dosed to water and is effective. In addition, the foam can be removed quickly, as opposed to a slowly collapsing foam where the time required for removing the foam is greater. This makes the composition extremely suitable for use in certain cleaning agents, in particular those for hard surfaces, to the exclusion of those where a rich foam is desired, such as with hand dishwashing detergents.
    In a preferred form, a composition according to a preferred form of the invention is used in a glass cleaning agent, most preferably a window cleaner. Sophorolactone has the advantage that it leaves few streaks. An additional advantage is that it has an anti-evaporating effect.
    Preferably the amount of the sophorolipid composition relative to the total weight of the composition is 0.05-10.0 weight percent.
    Preferably, the weight ratio of the sophorolipid composition to the one or more non-glycolipid surfactants is 1: 7 to 10: 1.
    The invention will now be further elucidated with reference to the following example, without however being limited thereto.
    Example 1: effect of the pre-culture
    In a first experiment, prior to the fermentation step, Candida bombicola ATCC 22144 cells were cultured for 72 hours at 25 ° C in 4 Erlenmeyer flasks with 1 liter of medium each with composition as listed in Table 1.
    Table 1: Corn steep liquor medium (CSL)
    In contrast to known disclosures, preculture is essentially oil-free substrate. In addition, the stationary phase was used instead of the exponential growth phase. After 72 hours the preculture is used to inoculate a sterilized Biostat U50 (Sartorius BBI Sytems) with 40 liters of sterile medium with the same composition as the preculture. A double fed batch fermentation was used at 110-130 revolutions per minute (rpm), 25 ° C, 0.5 bar and pH 3.5. Aeration is set at 1 vvm (amount of air introduced relative to the working volume of the bioreactor), reduced to 0.1 vvm after 40 hours to suppress excessive foaming, and again increased after 180 hours to 1.3 vvm. Immediately after inoculation, 3.33 g / l rapeseed oil (Bioplanet, food grade) was added. After 24 hours the continuous feed was fixed at 1 g / lh The feed was checked in function of the residual oil and the residual oleic acid, aimed at an oleic acid content of 1-5 g / l, at all times preventing concentrations above 8 g / l l go. The presence of residual oil in the fermentation broth was measured by heating a sample of fermentation fluid to 80 ° C and by visual inspection to determine whether an oil layer was formed. Glucose in solid form was added as soon as the concentration went below 20 g / l. Glycerol increased linearly from 0 g / l after 24 hours to about 35 g / l at 264 h. This glycerol profile and the complete disappearance of residual oil are good indicators for a correct fermentation. The most pronounced sophorolipid synthesis took place during the first 160 hours of fermentation with 240 g / l of oil added. With further addition, sophorolipids were formed at a lower rate, with an increased risk of overdosing the oil and with a steep increase in the broth viscosity. The sophorolipids were present as crystals during fermentation, as appeared under the microscope (X100 magnification). After 165 hours, 299 g / l of sophorolipids were formed at a speed of 1.81 g / l.h and a substrate conversion of 0.71. At that time, 5 g / l residual oleic acid was present, as measured by a hexane extraction. An HPLC-ELSD analysis was performed according to the method described by Steve Fleurackers in Eur. J. Lipid Sei. Techn, 108 (1): 5-12, 2006. This analysis showed that virtually no acid sophorolipids were present at a retention time of 24.4 minutes. The peak corresponding to the lactone form was about 50 times that of the acid form.
    After 330 hours, 403 g / l sophorolipids were formed at a rate of 1.22 g / l.h and a substrate conversion of 0.75. The residual oil content had dropped to 2 g / l and the acid / lactone ratio remained stable with mainly a single HPLC peak.
    The fermenter was then heated to 90 ° C to melt the crystals and obtain an oily layer that after cooling was easily separated from the broth by draining the fermenter the following morning. Once stored in vessels, the sophorolipid crystallized back and took the form of a hard solid.
    Additional experiments (2-3) were performed in which the culture medium, substrate and growth stage were changed. The results are summarized in Table 2.
    When comparing Experiments 1 and 3, both using rapeseed oil as a substrate, and 2 versus 3 where the latter worked with a preculture in the exponential growth phase and with an oily substrate, it becomes clear that the use of a corn steep-based medium liquor results in a substantial increase in production speed. The sophorolipids present are in crystalline form, which is important as it allows the isolation of lactone. The fermentation in experiment 1 was inoculated with a preculture of the stationary phase to which no oil substrate was added, confirming the hypothesis of a considerable number of previous experiments that this is advantageous for a maximum yield of sophorolipids in the lactone form.
    Table 2: Fermentation experiments
    Additional experiments (data not shown) each yielded low amounts of sophorolipids in acid form (D100 FB22: 11%, D100 FB23: 15%, D100 FB24: 13%) when working with a stationary and oil-free preculture. A summary of the experimental conditions and results is shown in Table 3.
    Table 3: Experimental conditions and results
    Example 2: effect of fatty acid control during fermentation
    Three flasks with 1500 ml pre-culture medium were each inoculated with Candida bombicola. After 72 hours of incubation at 25 ° C, the contents of the three flasks were pooled for inoculation of the seed tank. The development and morphology of the inocculum shake flasks was in line with the results of the lab-scale experiments. Limited foaming was observed for approximately 36 hours. No strange growth was observed.
    The seed fermentation was inoculated with approximately 4.5 I, 72 h old, shake flask material. After a somewhat slow start, the seed tank developed well. After 66 hours, still in the stationary phase, approximately 1 m3 of seed tank material was used to inoculate the fermenter. No strange growth was observed.
    The main fermentation was inoculated with approximately 1 m3 of the 2.2 m3 seed tank material, 66h old. During the process, non-sterile rapeseed oil was continuously fed while glucose was added in shots. For operational reasons, within a time frame of 198-216 hours, the main fermentation was terminated at 204 hours after inoculation. The weight of the broth at this time was about 41 tons, of which 31 volume% was a sophorolipid mixture that sedimented on heating.
    The dosage of glucose was based on the actual remaining glucose concentration of the broth, which was not lower than 60 g / l during the total course of the fermentation. Divided over 5 shots, 5639 kg of pure glucose was administered. Together with a batch administration of 2593 kg, a total of 8232 kg of glucose was added to the process.
    Due to a defective process control, the maximum permissible 10 g / l fatty acid of the broth was not taken into account in the rapeseed oil diet. The feeding was started immediately after inoculation, a total of 6300 kg of rapeseed oil were added. Eight hours before the end of the fermentation, the rapeseed oil feed was stopped.
    The resulting product remained liquid. Sophorolactone could not be selectively withdrawn from the reaction broth without the use of organic solvents.
    Another deviating observation was a moisture content of 45%. Crude sophorolactone obtained by a method according to an embodiment of the invention usually results in crude sophorolactone with a water content of 35-40%.
    Measurements of the remaining substrate in the final product showed that the fatty acid content of the broth must have been at least 4%.
    The determination of the remaining substrate content was advantageously carried out as follows: a sophorolactone sample of 200 g was liquefied by heating to 60 ° C. It was then extracted twice with the same volume of n-hexane in a separatory funnel. Evaporation of the pooled extracts yielded the bulk amount of the residual free fatty acid. The content was determined by weighing the obtained amount of residue and calculating the amount obtained in relation to the original weight of the sample.
    It is an advantage that the sophorolipids were available in liquid form, since it greatly accelerated the rate of phase separation, from about a day in the case of solid sophorolactone as a starting material, to half an hour before the liquid material. Furthermore, the inventors found that the use of cyclohexane instead of n-hexane resulted in a co-extraction of an unacceptable amount of sophorolactone. This was not the case with the use of n-hexane.
    Example 3: hydrolysis stability sophorolactone »
    To test the hydrolysis stability of the obtained sophorolactone, a sample of a non-aqueous sophorolactone solution was stored at 4 ° C and at 40 ° C for two months. Figure 1 is a graphical representation of a chromatogram taken before storage (black line) and after storage (gray curve) at 4 ° C. Figure 2 shows the results after 2 months at 40 ° C. In both cold storage and warm storage, almost overlapping Chromatograms were recorded in comparison with the measurement result for storage.
    The solutions are storage stable as evidenced by the substantial absence of a peak at a retention time of 30.5 minutes in the gray overlay graph which would indicate the presence of acid sophorolipid derived from hydrolyzed lactone.
    Example 4: reduction of surface tension of hydrolyzate
    This is illustrated with reference to Table 4 below which shows the static surface tension of aqueous solutions with increasing lactone content. Successively the surface tension of water is compared with that of lactone to which no base was added, fully hydrolysed lactone and partially hydrolysed lactone where hydrolysis was achieved by adding 0.6 to 2 equivalents of KOH per mole of lactone. Partial alkaline hydrolysis means that less than 3 moles of KOH per mole of lactone were added. Consequently, the three ester compounds present, i.e., the lactone bond and. two acetyl ester bonds, hydrolysed to form a mixture of different sophorolipids. It can be clearly seen that the surface tension was lowest in solutions obtained by 0.6-0.7 equivalents of base addition. This is advantageous for use in detergent formulations.
    Table 4: Measurements of the static surface tension on aqueous solutions with increasing lactone content
    Example 5: dishwashing powder formulation
    A min. 98% by weight of sophorolactone powder obtained by a method according to an embodiment of the invention was used for the formulation of a dishwashing powder.
    The basis was a standard formulation with 9.43% sodium citrate. 2H 2 O; 3.08% percarbonate; 2.72% sodium carbonate; , 2.05% sodium silicate; 1.05% sodium bicarbonate, 0.77% sodium polyaspartate; 0.62% tetra acetyl ethylene diamine (TAED) and 1.4% surfactant. As surfactant, either sophorolactone or a low-foaming alkyl polyglucoside, trade name Simulsol AS48, available from Seppic SA, was added.
    20 grams of dishwashing powder was dosed into a ZDF211 dishwasher and program D 50 ° C eco was carried out. In the dishwashers there were 7 types of plates (available at CFT, Vlaardingen, the Netherlands) mounted in a stainless steel frame. The results obtained are summarized in Table 5.
    Table 5: Stain removal efficacy of Simulsol AS48 relative to lactone on a series of stains.
    Rs = Y reflection value for contaminated; Rw = Y reflection value for crops
    The results above show that despite the low solubility, the sophorolactone was superior to Simulsol AS48.
    Example 6: storage stability hard surface cleaner
    A stock solution was prepared with -, 7.5% partially hydrolyzed sophorolipids, 5% surfactant (Glucopon 215), 3% ethanol and 0.5% glycerol monocaprylate. The pH of the formulation was adjusted to 6.3 with citrate and lactic acid. This stock solution was divided into five equal portions (Sample I-V). An increasing amount of oleic acid was added to four of the samples, in particular steel V-V, to simulate the effect of residual substrate on the stability of the final product.
    The samples were then divided into three. These sub-samples were stored at 4 ° C, 20 ° C or 40 ° C for 4 weeks. At the end of the four weeks, these substituents were visually inspected and assessed for their stability. The results are summarized in Table 6. Stable samples (referred to as "OK") remained homogeneous after storage under the described conditions, without separate layers being formed, without phase separation or sedimentation; this in contrast to unstable samples (referred to as "NOK").
    Table 6: Shelf life data of samples with different levels of oleic acid, measured at different temperatures.
    As appears from. Table 6 remaining substrate levels influence the storage stability of a cleaning agent. For this type of formulation it is recommended to keep the remaining substrate content below 0.2% of the final product, or 2.7% expressed on the sophorolipid. Formulations without a second surfactant, such as Glucopon 215 in this example, will be even more sensitive to remaining substrate levels, especially with regard to fatty acid.
    Example 7: window cleaner
    A preparation according to an embodiment of the invention suitable for cleaning glass surfaces, preferably windows, is for example as indicated in Table 7.
    Table 7: Example composition for window cleaner according to an embodiment of the invention
    Example 8: anti-fog composition
    One half of a mirror was treated with a 10% aqueous solution of a 10% solution of sophorolactone in ethanol and dried. The other half of the mirror was treated with a 10% solution of ethanol. Once dried, the mirror was held above boiling water to observe condensation or evaporation effects. The treated portion was not visibly covered with condensation and retained its mirror properties, while the untreated portion was completely covered with condensed water.
    In a preferred embodiment of the invention, the treated surface is glass or plastic film. The anti-fog composition as described above can be applied to films for food packaging, greenhouses, shower cabins and the like.
    权利要求:
    Claims (11)
    [1]
    A method for the selective preparation of a sophorolactone composition comprising the steps of: - pre-cultivating Candida bombicola or Candida apicola cells in the absence of an oily substrate until a stationary growth phase is achieved, - fermenting a reaction mixture with said cells, a sugar and a substrate, in an amount and under conditions, so that said cells metabolize sugar and substrate and thereby form sophorolactone and fatty acid, continuous feeding of said substrate to said cells wherein the formation of fatty acid and fatty acid levels in said reaction mixture is below 10 g / 1, resulting in the crystallization of at least a portion of said sophorolactone present in the reaction mixture, heating of said reaction mixture to a temperature of 60 ° C-90 ° C, whereby the sophorolactone crystals are melted, sedimentation of the fused sophorolactone to form a crude sophorolactone together assaying and removing the crude sophorolactone composition from the remaining reaction mixture without using an organic solvent. ~
    [2]
    A method according to claim 1, further comprising the steps of: - cooling said crude sophorolactone composition to a solid, such as a paste, - dispersing said solid in water, preferably descaled water, at a temperature of 5-25 ° C, using a water to solid ratio, expressed in weight percent of 0.5-15, forming an aqueous dispersion of sophorolactone crystals, - separating the crystals from the water, - repeating the dispersion 0 and 10 times and separating a temperature below 40 ° C continued, - drying the resulting sophorolactone composition until an anhydrous sophorolactone composition is obtained.
    [3]
    The method according to claim 1 or 2, wherein the substrate is selected from corn steep liquor, a triglyceride, isostearic acid, isostearic alcohol, and a protected ester of formula H- (CH 2) n-0-CO- (CH 2) m - C00H with a carbon chain length (n + m + 2) of 16-18.
    [4]
    The method of any one of claims 1-3 above, wherein the Candida species is Candida bombicola mutant strain M18, M30 or M33; preferably Candida bombicola M30.
    [5]
    A formulation in tablet or powder form, comprising an anhydrous sophorolactone composition obtainable by a method according to any one of claims 2 to 4, with the following composition: 70-100% by weight of sophorolactone, 0-1% by weight of sophorolipidic acid, and <0.2% by weight of fatty acid, and wherein a 1% aqueous solution of the formulation has a pH of 8.0-14.0.
    [6]
    A method for preparing a partially hydrolyzed, sophorolactone composition, comprising the steps of: - providing a sophorolactone composition, obtainable by a method according to any one of claims 1 to 4, with composition: 70-100% by weight of sophorolactone, 0-1% by weight sophorolipid acid <0.2% by weight of fatty acid, and - adding 0.5-1.0 equivalents of base to the aforementioned sophorolactone composition.
    [7]
    The method of claim 6, wherein 0.6-0.7 equivalents of base are used.
    [8]
    Partially hydrolyzed, sophorolactone composition, obtainable by a method according to claim 6 or 7, with composition 39% -45% sophorolipidic acid 61% -55% sophorolactone, expressed as a weight percentage relative to the total amount of sophorolipids in the composition, and less than 0.2% by weight of fatty acid expressed in relation to the total composition.
    [9]
    Use of a composition according to claim 8, as a surfactant in a composition for cleaning hard surfaces selected from a window cleaner, a tile cleaner, a degreaser, a dishwasher product and WC cleaner.
    [10]
    Use of a composition according to claim 8, as a foam-breaking agent for one or more non-glycolipid surfactants in a detergent composition selected from a window cleaner, a tile cleaner, a degreaser, a dishwasher product and washing machine product.
    [11]
    The use according to claim 9 or 10, wherein the amount of the sophorolipid composition relative to the total weight of the composition is 0.05-10.0 weight percent.
    类似技术:
    公开号 | 公开日 | 专利标题
    BE1019942A3|2013-02-05|IMPROVED SOPHOROLACTON COMPOSITIONS, METHOD OF PREPARATION AND USE.
    US8664373B2|2014-03-04|Method for producing sophorose lipid
    Foley et al.2012|Derivation and synthesis of renewable surfactants
    Roelants et al.2019|Production and applications of sophorolipids
    Fleurackers2006|On the use of waste frying oil in the synthesis of sophorolipids
    JP2018514222A|2018-06-07|Semi-continuous process for producing rhamnolipids with high yield and high titer
    Morya et al.2013|Production and characterization of low molecular weight sophorolipid under fed-batch culture
    US6433152B1|2002-08-13|Sophoroselipids, method for their production and use
    AU2021269323A1|2021-12-09|Fatty acid esters against infections in fermentations
    JP2007252279A|2007-10-04|Method for highly efficiently producing mannosylerythritol lipid
    FR2692593A1|1993-12-24|A process for the production of acetylated sophorolipids in their acid form from a substantial substrate and an oil or an ester.
    FR2754829A1|1998-04-24|PROCESS FOR THE PRODUCTION OF SOPHOROLIPIDS BY CYCLIC FERMENTATION USING ESTERS OF FATTY ACIDS OR OILS
    JP4924840B2|2012-04-25|Mannosyl erythritol lipid and method for producing the same
    WO2012167813A1|2012-12-13|Improved sophorolactone production
    JP4735971B2|2011-07-27|Mannosyl erythritol lipid production method
    EP2718454A1|2014-04-16|Improved sophorolactone production
    Ashby et al.2019|Sophorolipids: Unique microbial glycolipids with vast application potential
    JP2020529203A|2020-10-08|Improved production of ramnolipide using at least two carbon sources
    EP3271369A1|2018-01-24|Method for producing d-galacturonic acid derivatives and compositions directly from pectins
    US8729319B2|2014-05-20|Method for producing higher alcohol
    EP0625182A1|1994-11-23|Stable pumpable synthetic detergent composition and process for the storage thereof.
    EP2220202B1|2016-10-05|Laundry product
    DK169342B1|1994-10-10|Esters of glycosides of monosaccharides, a process for preparing them, and cleaning agents or cleansers which comprise these esters
    JP2008301748A|2008-12-18|Method for producing glycolipid
    EP2220201B1|2017-04-12|Laundry product
    同族专利:
    公开号 | 公开日
    US10287615B2|2019-05-14|
    WO2012168325A1|2012-12-13|
    US20140194336A1|2014-07-10|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    EP1411111A1|2001-06-27|2004-04-21|Saraya Co., Ltd.|Low foaming detergent compositions|
    EP1953237A1|2007-02-01|2008-08-06|Ecover N.V.|A method for the production of short chained glycolipids|
    WO2009141407A2|2008-05-21|2009-11-26|Ecolife B.V.|A method for the production of medium-chain sophorolipids|
    DE3526417A1|1985-07-24|1987-02-05|Wella Ag|COSMETIC PRODUCTS CONTAINING SOPHOROSELIPID LACTON AND ITS USE|
    CA2060698C|1991-02-12|1997-09-30|Peter J. Hall|Detergent compositions|
    US5559089A|1992-03-12|1996-09-24|The Procter & Gamble Company|Low-dosage automatic dishwashing detergent with monopersulfate and enzymes|
    FR2699928B1|1992-12-30|1995-01-27|Inst Francais Du Petrole|Composition containing a surfactant compound and sophorolipids and method for decontaminating a porous medium polluted by hydrocarbons.|
    DE19518982A1|1995-05-29|1996-12-05|Hoechst Ag|Novel glucose and sophoroselipids, a process for their preparation and their use|
    FR2740779B1|1995-11-08|1997-12-05|Rhone Poulenc Chimie|COMPOSITION BASED ON ENZYME AND SOPHOROLIPIDE IN LACTONE FORM AND USE THEREOF IN DETERGENT FORMULATIONS FOR THE WASHING OF LAUNDRY|
    FR2754829B1|1996-10-18|1998-12-11|Inst Francais Du Petrole|PROCESS FOR PRODUCING SOPHOROLIPIDS BY CYCLIC FERMENTATION WITH SUPPLY OF FATTY ACID ESTERS OR OILS|
    DE19749413A1|1997-11-07|1999-05-12|Hoechst Ag|Novel sophorose lipids, process for their preparation and use|
    FR2779057B1|1998-05-29|2001-06-15|Inst Francais Du Petrole|USE OF SOPHOROLIPIDS COMPRISING DIACETYLATED LACTONS AS A STIMULATOR OF THE METABOLISM OF FIBROBLASTS OF THE SKIN|
    FR2789330B1|1999-02-10|2001-03-09|Agro Ind Rech S Et Dev Ard|STABLE EMULSION, PROCESS FOR PREPARING THE SAME, AND AGENT THEREFOR, WHICH INCLUDES FATTY ALCOHOL AND POLYGLYCOSIDES|
    WO2004044216A1|2002-11-06|2004-05-27|Polytechnic University|Antimicrobial properties of various forms of sophorolipids|
    US7939489B2|2002-12-23|2011-05-10|Avon Products, Inc.|Oil absorbent topical compositions and methods for using same|
    PT1445302E|2003-01-28|2006-10-31|Ecover N V|DETERGENT COMPOSITIONS|
    US7556654B1|2004-10-15|2009-07-07|Naturell|Methods for cleaning materials|
    US8664373B2|2008-10-28|2014-03-04|Kaneka Corporation|Method for producing sophorose lipid|
    DE102009045077A1|2009-09-29|2011-03-31|Evonik Goldschmidt Gmbh|Use of sophorolipids and their derivatives in combination with pesticides as adjuvant / additive for crop protection and industrial non-crop sector|
    WO2011120776A1|2010-03-31|2011-10-06|Unilever Plc|Mild to the skin, foaming detergent composition|
    EP2555620A4|2010-04-05|2013-10-23|Politechnic Inst Univ New York|Sophorolipid analog compositions|
    EP2718411B1|2011-06-06|2019-09-11|Ecover Co-ordination Center N.V.|Sophorolactone compositions and uses thereof|EP2718411B1|2011-06-06|2019-09-11|Ecover Co-ordination Center N.V.|Sophorolactone compositions and uses thereof|
    DE102011090030A1|2011-12-28|2013-07-04|Evonik Industries Ag|Aqueous hair and skin cleansing compositions containing biosurfactants|
    US20170051197A1|2014-04-21|2017-02-23|Cargill, Incorporated|Sophorlipid-containing compositions having reduced pour point temperature|
    WO2017157659A1|2016-03-18|2017-09-21|Evonik Degussa Gmbh|Granulate comprising an inorganic solid carrier with at least one biosurfactant contained thereon|
    CN109678914B|2018-12-25|2021-12-07|合肥工业大学|Method for pretreating sophorolipid fermentation liquor and separating and purifying sophorolipids with different structures|
    WO2021229017A1|2020-05-13|2021-11-18|Bio Base Europe Pilot Plant|Efficient synthesis of omega-glycosides and alkyl glycosides|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    EP2011059310|2011-06-06|
    PCT/EP2011/059306|WO2012167813A1|2011-06-06|2011-06-06|Improved sophorolactone production|
    PCT/EP2011/059310|WO2012167815A1|2011-06-06|2011-06-06|Sophorolactone compositions and uses thereof|
    EP2011059306|2011-06-06|
    [返回顶部]