Mechanoenzymatic biosurfactant synthesis

Abstract

The present invention relates to a method for mechanoenzymatically preparing non-ionic ester surfactants on the basis of fatty acids / fatty acid alcohols and sugars, sugar alcohols or sugar acids, wherein a mixture of fatty acid starting materials and sugar starting materials of the ester surfactants and an enzyme are subjected to a kneading treatment in an extruder in order to form the ester surfactants. The method specified allows for the economical preparation of corresponding ester surfactants with short reaction times and with substantial to even complete exclusion of organic solvents. The present invention also relates to non-ionic ester surfactants which can be prepared or have been prepared by the method according to the invention, and to the use of an extruder for preparing non-ionic ester surfactants on the basis of fatty acids / fatty acid alcohols and sugars, sugar alcohols or sugar acids by means of mechanoenzymatic conversion.

Description

[0001] September 3, 2025

[0002] Technikum Laubholz GmbH M / TLH-018-PC BL / cbe / mu

[0003] Mechanoenzymatic biosurfactant synthesis

[0004] Description

[0005] The present invention relates to a process for the mechanoenzymatic production of non-ionic ester surfactants based on fatty acids / fatty acid alcohols and sugars, sugar alcohols, or sugar acids, wherein a mixture of fatty acid and sugar starting materials of the ester surfactants and an enzyme are subjected to kneading in an extruder to form the ester surfactants. The present invention further relates to non-ionic ester surfactants that can be produced or have been produced according to the process according to the invention, and to the use of an extruder for the production of non-ionic ester surfactants based on fatty acids and sugars, sugar alcohols, or sugar acids by means of mechanoenzymatic reaction.

[0006] State of the art

[0007] Non-ionic ester surfactants based on fatty acids and sugars or sugar alcohols play a major role as emulsifiers in the food industry and in cosmetic and pharmaceutical products. One example of such a non-ionic surfactant is sorbitan monolaurate, which is also approved as a food additive under the number E 493. E493 is produced by the esterification of lauric acid and sorbitol at elevated temperatures (140°C and above).

[0008] One problem with the traditional production of such non-ionic surfactants is the comparatively high amount of energy required for the reaction. For example, if the reaction is carried out at higher temperatures, sugar degradation can occur under acidic conditions, which reduces the yield of the process. Furthermore, side reactions can lead to discoloration, which M / TLH-018-PC

[0009] 2 subsequently have to be removed from the product with considerable effort.

[0010] US Patent 4297290 A describes a process for the production of sorbitan monolaurate, in which, in a first step, sorbitol is reacted with p-toluenesulfonic acid at a temperature of approximately 120°C to form the corresponding anhydrous sugar alcohol. The resulting anhydrous sugar alcohol is then reacted with sodium hydroxide and lauric acid at 200°C for a reaction time of 4 hours to produce sorbitan monolaurate. The product is subsequently bleached with hydrogen peroxide.

[0011] An alternative to the production of non-ionic surfactants such as sorbitan monolaurate is the enzymatic reaction of sorbitol with lauric acid. For example, US 10,081,748 B2 describes the production of sorbitol monoesters by transesterification of the corresponding fatty acid vinyl esters with lipase enzymes in acetone. While this process yields the desired product in relatively high yields (approximately 70%) at temperatures below 50°C, it also requires relatively long reaction times of about 48 hours. Further disadvantages of this process include the use of fatty acid vinyl esters, which must first be produced from the corresponding fatty acids, and the reaction in acetone as an organic solvent, which is cost-inefficient and necessitates additional technical effort to prevent solvent emissions during production.

[0012] Another method for the production of sugar-fatty acid esters, also based on an enzymatically catalyzed reaction, is described in WO 2020 / 200879 Al. In this method, an enzyme immobilized on a support is used as a stationary phase, over which a solution of glucose and lauric acid is passed at elevated temperature. This method also requires the use of an organic solvent.

[0013] Against this background, there is a need for a process for the production of non-ionic surfactants based on sugars, sugar alcohols, sugar acids and fatty acids, in which the non-ionic surfactants are classified under M / TLH-018-PC

[0014] 3 can be produced under comparatively mild conditions and with a largely complete exclusion of organic solvents.

[0015] In R. Hollenbach et al., ACS Sustainable ern. Eng. 2022, 10, pp. 10192-202, a mechanoenzymatic process for the production of sugar esters is described, in which the sugars are reacted with vinyl fatty acid esters under enzyme catalysis. Solvents such as 2-methyl-2-butanol, ethyl acetates, acetone, and (-)-menthol (as a deeply eutectic solvent) were used. The reactions were carried out in a ball mill with reaction times ranging from 5 to 90 minutes.

[0016] While the process described by Hollenbach already requires very small amounts of solvent, this process is also not economically optimal due to the fatty acid vinyl ester used as a starting material and the comparatively long processing time. Furthermore, the process is limited to batch processing because it is carried out in a ball mill.

[0017] Therefore, there is also a need for a manufacturing process for non-ionic surfactants of the type described, in which fatty acids can be used in unmodified form, i.e., as pure fatty acids, and in which the desired product is obtained with the shortest possible reaction time. Furthermore, there is a need for a process that can be carried out as a continuous process.

[0018] The present invention addresses this need.

[0019] Detailed description of the invention

[0020] In the investigations underlying this invention, it was surprisingly found that a mechanoenzymatic direct reaction of sugars, sugar alcohols, or sugar acids with fatty acids or fatty acid alcohols can be achieved by kneading a mixture of the starting materials and an added enzyme catalyst in an extruder. In such a reaction, the M / TLH-018-PC

[0021] 4

[0022] The use of solvents was avoided, and a comparatively high conversion rate could be achieved with very short reaction times.

[0023] Accordingly, the present invention relates in a first aspect to a process for the mechanoenzymatic production of non-ionic ester surfactants based on fatty acids or fatty acid alcohols and sugars, sugar alcohols or sugar acids, wherein a mixture of fatty acid and sugar starting materials of the ester surfactants and an enzyme are subjected to a kneading treatment in an extruder to form the ester surfactants.

[0024] In this context, "mechanoenzymatic" refers to a process carried out in the presence of an enzyme, in which the reaction mixture is mechanically processed. According to the invention, it is preferred that the conversion of the starting materials in the mixture to ester surfactants occurs essentially or exclusively through the mechanoenzymatic reaction, and not through upstream or downstream steps. "Essentially" here means that at least 80%, and preferably at least 90%, of the total ester surfactants formed are to be produced by the mechanoenzymatic reaction.

[0025] In the following description, the terms “starting material”, “starting material” and “starting product” are used synonymously.

[0026] Fatty acid starting materials include both the fatty acids themselves and the fatty acid alcohols. In the context of the invention described here, the use of fatty acids is preferred over fatty acid alcohols. In other words, the specified process preferably produces ester surfactants that are obtainable from fatty acids and sugars or sugar alcohols.

[0027] Regarding the temperature of the reaction, the present invention is not subject to any significant limitations, with the preferred application being that the reaction mixture is in a liquid state. On the other hand, the temperature should not be so high that relevant decomposition of the sugars or sugar alcohols occurs during the mechanoenzymatic treatment. To bring the reaction mixture into such a state, M / TLH-018-PC

[0028] 5

[0029] To achieve the desired shape, a small amount of solvent (i.e., up to 50 wt% of the total mixture, preferably 20 wt% of the total mixture or less, and more preferably 10 wt% of the total mixture or less) can be added. However, it is particularly preferred, and with regard to economic considerations, if no solvent is added to the reaction mixture for the reaction in the extruder (a liquid reaction mixture in the melt is possible in this case).

[0030] Regarding the "liquid state," it should be noted that this refers only to the reacting components; that is, a "liquid state" exists in the context of the described invention even if the reaction mixture contains an enzyme immobilized on a solid support that is not dissolved in the reaction mixture. In the context of the present invention, a solvent is a chemical compound that facilitates the achievement of a liquid state of the reaction mixture but does not participate in the reaction. Since the reaction is an "esterification," water is expediently excluded as a solvent in larger quantities, i.e., more than 5% by weight of the mixture processed in the mechanoenzymatic treatment.

[0031] According to the invention, the temperature at which the mixture of fatty acid and sugar starting materials for the ester surfactants and an enzyme is subjected to kneading is not subject to any relevant restrictions. However, since, as mentioned, it is advantageous for the reaction mixture to be in liquid form for the reaction, it is preferred that the reaction be carried out at an elevated temperature, i.e., at least 40°C. On the other hand, the temperature should not be so high as to cause significant degradation of the enzyme or the sugars, i.e., preferably not more than 170°C and more preferably not more than 150°C. A preferred temperature range for the kneading treatment can be specified as 70 to 150°C and more preferably 80 to 120°C. Alternatively or additionally, it is preferred that the fatty acid and sugar starting materials are present in the form of a melt.

[0032] The residence time in the extruder is also not subject to any relevant restrictions in the context of the process described here, and can be adjusted by a person skilled in the art with regard to maximizing the conversion of the M / TLH-018-PC.

[0033] 6

[0034] Starting materials are suitably adjusted to the desired non-ionic ester surfactants. In most cases, a maximum treatment residence time of 60 minutes is sufficient, although residence times in the range of 2.5 to 20 minutes, and especially 3 to 12 minutes, can be considered particularly suitable. Those skilled in the art are aware of a certain dependency between residence time and treatment temperature (at a higher treatment temperature, a shorter residence time may be sufficient for the same conversion than at a lower treatment temperature).

[0035] The screw feed speed at which the extruder is operated in the process according to the invention can also be adjusted by a person skilled in the art within a suitable range. In the investigations underlying this invention, a screw feed speed in the range of 20 to 400 revolutions per minute, and in particular 25 to 300 revolutions per minute or 30 to 100 revolutions per minute, has proven to be particularly advantageous. However, since the screw feed speed and the residence time are also in a certain relationship to each other, screw feed speeds outside these ranges can also lead to good conversion rates.

[0036] The fatty acid and sugar starting materials can be used in a ratio suitable for the production of the non-ionic ester surfactants, for example in a ratio in the range of 1:3 to 3:1, preferably in the range of 1:2 to 2:1 and further preferably in the range of 1:1.5 to 1.5:1.

[0037] For the process according to the invention, it is preferred if the fatty acid and sugar starting materials of the non-ionic ester surfactants are used in a ratio as close to equimolar as possible, so that the formation of undesirable byproducts is suppressed or subsequent separation of excess starting material is avoided. Accordingly, it is particularly preferred for the kneading process if the fatty acid and sugar starting materials of the non-ionic ester surfactants are mixed in a molar ratio in the range of 1:1.2 to 1.2:1, more preferably 1:1.1 to 1.1:1, and even more preferably in a ratio of approximately 1:1, and fed in this form to the kneading process in the extruder. M / TLH-018-PC

[0038] 7

[0039] The enzyme is expediently added to the reaction mixture in an amount that ensures the fastest possible conversion of the starting materials while still guaranteeing an economical process. Accordingly, within the scope of the process described here, it is preferred that the enzyme for the kneading treatment be included in the mixture in an amount of 2 to 15 wt.%, more preferably 5 to 12 wt.%, and even more preferably 7 to 10 wt.%, if the enzyme is immobilized on a solid support. This weight refers to the proportion of the enzyme to the total mass of the mixture. The mass of the "enzyme" also includes any solid supports on which the actually catalytically active enzyme is immobilized.

[0040] Alternatively or additionally, it is preferred if the enzyme is used in an amount of 10,000 to 100,000 enzyme units, more preferably 20,000 to 80,000 enzyme units, and even more preferably 30,000 to 60,000 enzyme units (1 enzyme unit = the amount of enzyme that converts 1 pmol of substrate per minute; the substrate is the substrate specified by the manufacturer for the lipase in question, e.g., propyl laurate, from which lauric acid is cleaved).

[0041] Enzymes that can be used in the process according to the invention for the production of ester surfactants include, in particular, lipases such as Candida antarctica lipase B (commercially available, for example, as Novozym® 435, for example from Strem Chemicals, Inc.), Thermomyces lanuginosus lipase, Porcine pancreas lipase, Aspergillus oryzae lipase, or Candida rugosa lipase. Alternatively, acyltransferases can also be used in the process.

[0042] With regard to the type of extruder used in the process according to the invention, the present invention is not subject to any relevant restrictions; that is, any type of extruder in which a kneading treatment can be carried out can be used. In a preferred embodiment, the extruder is selected from the group comprising single-screw extruders, twin-screw extruders, and multi-screw extruders. Alternatively or additionally, within the scope of the specified process, it is advantageous for the extruder to have several kneading zones, for example, 2 to 5 kneading zones, or at least 3 kneading zones, and in particular 3 to 10 kneading zones. M / TLH-018-PC

[0043] 8

[0044] As an alternative to an extruder, a device for mechanoenzymatic treatment can also be used in the process according to the invention, in which the mixture can be treated mechanically and at elevated temperature, and which is not an extruder in the strict sense. Such a device is, for example, a LIST kneader, so that processes described herein are also intended to be encompassed in which a LIST kneader is used for the mechanoenzymatic treatment instead of an extruder.

[0045] It is still preferred if the extruder has alternating screw zones (i.e., zones where material is only conveyed) and kneading zones, as well as reverse screw elements. Reverse screw elements are not required, however, and an extruder without such elements in the screw configuration can also be used. The temperature in the different zones can be the same or different, and it is advantageous if the temperature at the extruder feed is lower than in a zone where the maximum temperature set in the extruder is reached. Furthermore, it is advantageous if the temperature in a final zone of the extruder (after which the reaction mixture is discharged) is lower than in a zone where the maximum temperature set in the extruder is reached.

[0046] As mentioned above, non-ionic ester surfactants based on fatty acids / fatty acid alcohols and sugars, sugar alcohols, or sugar acids can be produced using the process according to the invention. In these surfactants, the fatty acids / fatty acid alcohols form the lipophilic part of the surfactant, and the sugars, sugar alcohols, or sugar acids form the hydrophilic part. Particularly preferred non-ionic ester surfactants produced using the process according to the invention are those of the formula ROC(O)R. 1 or RC(O)OR 2 , where RO is the residue of a sugar or sugar alcohol, RC(O)O is a sugar acid, OC(O)R 1 a fatty acid residue and OR 2 a fatty acid alcohol residue, wherein the sugar is a C5 or C6 sugar or a disaccharide based on C5 and / or C6 sugars, the sugar acid and the sugar alcohol are a sugar acid or a sugar alcohol derived therefrom.

[0047] The fatty acid used as a starting material is an organic compound whose carboxylic acid function is modified with an M / TLH-018-PC.

[0048] 9

[0049] are substituted with an alkyl group. Suitable alkyl groups that, together with the carboxylic acid function (-CO2H), form the fatty acid, include, for example, the following: n-pentyl, n-hexyl, n-heptyl, n-octyl (alkyl group of caprylic acid), n-nonyl (alkyl group of pelargonic acid), n-decyl (alkyl group of capric acid), n-lauryl, iso-pentyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-lauryl, 2,2-dimethylpropyl, 4-methyl-2-pentyl, 2,3-dimethylpentyl, 3-ethyl-2-pentyl, and 3-ethyl-5-methyloctyl. Other examples of saturated alkyl groups include n-undecanyl, n-dodecanyl, n-tridecanyl (alkane of myristic acid), n-tetradecanyl, n-pentadecanyl (alkane of palmitic acid), n-hexadecanyl (alkane of margaric acid), n-heptadecanyl (alkane of stearic acid), n-octadecanyl, n-nonadecanyl (alkane of aric acid), n-icosanyl, 4-methyldodecanyl, and 3-ethyl-5-methylpentadecanyl.

[0050] Unsaturated fatty acids that can be used in non-ionic ester surfactants include fatty acids substituted at the carboxylic acid function with an alkylene group selected from the group comprising n-pentenyl, n-hex-2-enyl, n-hept-3-enyl, n-oct-4-enyl, n-non-5-enyl, n-dec-6-enyl, n-dodec-3,6,-dienyl, n-heptadec-9-enyl (alkene residue of oleic acid), iso-pentenyl, iso-hexenyl, iso-heptenyl, iso-octenyl, iso-nonenyl, iso-decenyl, iso-dodecenyl, 3,3,3-trimethylpropenyl, 4-methyl-2-pentenyl, 2,3-dimethylpent-2-enyl. 3-Ethyl-2-pentenyl, 2-Isopropyl-2,2-dimethylpentynyl, and 3-Ethyl-5-methyloct-2,4-dienyl. Other examples of unsaturated alkyl groups include n-Heptadec-3,6-dienyl, n-Heptadec-8,1-dienyl, 3-Isopropyl-2,4-dimethylpentynyl, and 3,3,3-trimethylheptadecynyl.

[0051] Fatty acids substituted with a hydroxy-alkyl group at the carboxylic acid function can also be used for the production of non-ionic ester surfactants. The hydroxy-alkyl group is preferably selected from the group comprising hydroxy-pentyl, hydroxy-hexyl, hydroxy-heptyl, hydroxy-octyl, hydroxy-nonyl, hydroxy-decyl, hydroxy-lauryl, hydroxy-undecanyl, hydroxy-dodecanyl, hydroxy-tridecanyl, hydroxy-tetradecanyl, hydroxy-pentadecanyl, hydroxy-hexadecanyl, hydroxy-heptadecanyl, hydroxy-octadecanyl, hydroxy-nonadecanyl, and hydroxy-icosanyl. For hydroxycarboxylic acids, it is advantageous if the hydroxy group is positioned at the α- or β-carbon atom relative to the carboxylic acid. M / TLH-018-PC

[0052] 10

[0053] In the context of the process according to the invention, it is preferred if the fatty acid is an unbranched or branched saturated or unsaturated fatty acid with a carbon chain length in the range of 5 to 20, and particularly 8 to 20. A particularly preferred option is an unbranched or branched saturated or unsaturated fatty acid selected from caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, caproleic acid, undecylenic acid, myristoleic acid, palmitoleic acid, and oleic acid.

[0054] In general, for the specified non-ionic ester surfactants containing a C5 or C6 sugar as a hydrophilic residue, it is preferred that the C5 or C6 sugar be selected from the group comprising xylose, arabinose, glucose, galactose, mannose, sorbose, and fructose. Sugar acids that may be used include, for example, glucuronic acid, galacturonic acid, xuloronic acid, gluconic acid, galactonic acid, mannosugaric acid, or xylonic acid, preferably in the respective D-form, and preferably D-gluconic acid, D-glucuronic acid, and D-mannosugaric acid. Suitable sugar alcohols include, in particular, xylitol, mannitol, and sorbitol. The specified sugars, sugar alcohols, and sugar acids are characterized by high natural availability and correspondingly low cost. For example, glucose is available by enzymatic degradation of starch or cellulose.Hexoses, such as mannose, glucose, and galactose, and pentoses, particularly in the form of xylose or arabinose, are obtainable through the degradation of hemicelluloses, which are obtained as a byproduct of the separation of lignocellulosic materials such as wood. The term "disaccharide based on C5 and / or C6 sugars" includes disaccharides based on two C6 sugars, disaccharides based on two C5 sugars, and disaccharides based on one C6 and one C5 sugar. Such disaccharides are preferably those based on C6 sugars such as sucrose, maltose, isomaltose, lactose, or cellobiose, and especially sucrose, maltose, or lactose. A suitable disaccharide based on one C6 and one C5 sugar is, for example, sambubiose.

[0055] For the production of a non-ionic ester surfactant of the formula RC(O)OR 2A nonpolar fatty acid alcohol is used as the group, which is linked to a sugar acid via an ester bond. The fatty acid alcohol can preferably be produced by reducing one of the fatty acids mentioned above. (See M / TLH-018-PC.)

[0056] Eleven preferred fatty acid alcohols can be specified, those in which R 2 The term refers to the residue of an unbranched or branched saturated or unsaturated fatty acid alcohol with a carbon chain length in the range of 10 to 20. Most preferably, the fatty acid alcohol is a fatty acid alcohol obtainable by reduction of capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, caproleic acid, undecylenic acid, myristoleic acid, palmitoleic acid, oleic acid, or hydroxydecanoic acid.

[0057] After passing through the extruder, the produced non-ionic surfactant can be isolated by separating any unreacted starting materials from the reaction and the enzyme used. This can be achieved in one or more steps by extracting the unreacted sugars, sugar alcohols, sugar acids, and fatty acids, for example, by exploiting differences in polarity (unreacted sugars, sugar alcohols, or sugar acids are significantly more polar than the produced ester surfactants, while the fatty acids or fatty acid alcohols are significantly less polar). Similarly, the enzymes can be separated along with the sugars, sugar alcohols, sugar acids, and fatty acids (enzymes on a solid support can be easily filtered off; pure enzymes can be separated from the ester surfactants using a suitable solvent).Separated starting materials and enzymes can subsequently be reintroduced into the process according to the invention as starting materials.

[0058] If a solvent is used for extraction or separation of the ester surfactants from the enzymes used in the reaction, for example by filtering off the enzyme, this solvent can subsequently be removed to isolate the ester surfactant from the filtrate.

[0059] Another aspect of the present invention relates to a non-ionic ester surfactant which can be produced or has been produced according to a process as described above.

[0060] A further aspect of the present invention relates to the use of an extruder for the production of non-ionic ester surfactants based on M / TLH-018-PC.

[0061] 12

[0062] Fatty acids and sugars, sugar alcohols, or sugar acids are converted via mechanoenzymatic reaction. Preferably, a mixture of fatty acid and sugar starting materials for the ester surfactants and an enzyme is used in an extruder to form the ester surfactants.

[0063] A further aspect of the present invention relates to the use of monosaccharides produced from hemicellulose for the production of non-ionic ester surfactants, wherein the monosaccharides are subjected to a mechanoenzymatic reaction with a fatty acid, preferably in an extruder.

[0064] For the specified uses, even if not explicitly stated here, embodiments and configurations that are indicated as preferred, suitable or expedient in connection with the above-described method are also preferred, suitable or expedient, unless this results in an obvious contradiction in meaning.

[0065] The present invention is illustrated in more detail below by means of some exemplary embodiments, which, however, should not be considered in any way as limiting the scope of protection of the claims or of the application on which they are based:

[0066] Example:

[0067] To a mixture of 52.4 g (0.261 mol) lauric acid and 47.6 g sorbitol (0.261 mol) 10 g of Novozym 435 (50,000 rpm) are added. This mixture is then fed into an extruder (twin-screw extruder with 5 mixing zones). The kneading zones consist of a combination of forward-kneading and reverse-kneading elements. The extruder operates at a speed of 30 rpm with a residence time of 4 minutes. The middle section of the extruder is set to a temperature of 110°C, and the feed section is set to a temperature of 70°C. A long-helix conveying element is positioned at the feed point.

[0068] The melt contained at the extruder outlet is suspended in ethyl acetate. For qualitative determination of the conversion, the suspension is applied to an M / TLH-018-PC

[0069] 13

[0070] Thin-layer chromatography plates were applied and eluted with a mixture of 65 / 10 / 1 chloroform / methanol / water and stained with a thymol staining reagent consisting of 0.1 g / L thymol in ethanol-sulfuric acid 19:1 (v:v). The formation of a significant amount of sorbitol laurate could be detected on the developed plates.

[0071] Analogous tests with Thermomyces lanuginosus lipase and Candida rugosa lipase show comparable conversion rates to sorbitol laurate.

Claims

M / TLH-018-PC 14 Claims 1. A method for the mechanoenzymatic production of non-ionic ester surfactants based on fatty acids / fatty acid alcohols and sugars, sugar alcohols or sugar acids, wherein a mixture of fatty acid and sugar starting materials of the ester surfactants and an enzyme are subjected to a kneading treatment in an extruder to form the ester surfactants.

2. Method according to claim 1, characterized in that the mixture of fatty acid and sugar starting materials of the non-ionic ester surfactants and an enzyme is exposed to a temperature in the range of 70 to 150°C and preferably 80 to 120°C during the kneading treatment and / or that the fatty acid and sugar starting materials are present in the form of a melt.

3. Method according to claim 1 or 2, characterized in that the mixture is treated with a residence time of the mixture in the extruder of at least 60 min, preferably in the range of 2.5 to 10 min and more preferably 3 to 8 min.

4. Method according to at least one of claims 1 to 3, characterized in that the extruder is operated with a screw speed in the range of 20 to 100 revolutions / min and preferably 25 to 60 revolutions / min.

5. Method according to at least one of the preceding claims, characterized in that the fatty acid and sugar starting materials of the non-ionic ester surfactants for the kneading treatment are mixed in a molar ratio in the range of 1:3 to 3:1, preferably 1:2 to 2:1, more preferably 1:1.5 to 1.5:1, even more preferably 1:1.2 to 1.2:1, even more preferably 1:1.1 to 1.1:1 and even more preferably in a ratio of about 1:

1.

6. Method according to at least one of the preceding claims, characterized in that the enzyme for kneading treatment is included in the mixture in an amount of 2 to 15 wt.% and preferably 5 to 12 wt.%. M / TLH-018-PC 15 7. Method according to at least one of the preceding claims, characterized in that the kneading treatment is carried out in an extruder selected from the group comprising single-screw extruders, twin-screw extruders and multi-screw extruders, or in a LIST kneader and / or an extruder with several kneading zones, preferably at least 3 kneading zones and further preferably 3 to 10 kneading zones, is used.

8. Method according to at least one of the preceding claims, characterized in that, within the framework of the method, ester surfactants of the formula ROC(O)R are used. 1 or RC(O)OR 2 are produced, where RO is the residue of a sugar or sugar alcohol, RC(O)O is a sugar acid, OC(O)R1 a fatty acid residue and OR 2 a fatty acid alcohol residue, wherein the sugar is a C5 or C6 sugar or a disaccharide based on C5 and / or C6 sugars, and the sugar acid and sugar alcohol are a sugar acid and a sugar alcohol derived therefrom, respectively.

9. The method according to claim 8, characterized in that the C5 or C6 sugar or the disaccharide based on C5 and / or C6 sugars, the sugar acid and the sugar alcohol is one or more selected from the group comprising xylose, arabinose, rhamnose, glucose, galactose, mannose, sorbose, fructose, sucrose, maltose, isomaltose, lactose, sambubiose, xyluronic acid, glucuronic acid, galacturonic acid, xylitol, arabitol, mannitol, sorbitol, gluconic acid, galactonic acid and xylonic acid.

10. Method according to at least one of the preceding claims, characterized in that the fatty acid is an unbranched or branched saturated or unsaturated fatty acid with a C-chain length in the range of 8 to 20, preferably selected from caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, caproleic acid, undecylenic acid, myristoleic acid, palmitoleic acid and oleic acid or the residue of a branched fatty acid with one or more methyl side chains or the residue of a β-hydroxy fatty acid. M / TLH-018-PC 16 11. Method according to at least one of the preceding claims, characterized in that the fatty acid alcohol is a fatty acid alcohol with a C-chain length in the range of 10 to 20, which is preferably selected from fatty acid alcohols of capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, caproleic acid, undecylenic acid, myristoleic acid, palmitoleic acid, oleic acid, or hydroxydecanoic acid.

12. A method according to at least one of the preceding claims, characterized in that the non-ionic ester surfactant is isolated by extracting the sugars, sugar alcohols or sugar acids and fatty acids / fatty acid alcohols not reacted in the reaction from the mixture treated in the extruder, dissolving the produced non-ionic ester surfactants and filtering off the enzymes, and optionally removing the solvent from the filtrate.

13. Non-ionic ester surfactant produced by a process according to any one of claims 1 to 12.

14. Use of an extruder for the production of non-ionic ester surfactants based on fatty acids / fatty acid alcohols and sugars, sugar alcohols or sugar acids by means of mechanoenzymatic reaction, preferably wherein a mixture of fatty acid and sugar starting materials of the ester surfactants and an enzyme is treated in an extruder to form the ester surfactants.

15. Use of monosaccharides produced from hemicellulose for the production of non-ionic ester surfactants, wherein the monosaccharides are subjected to a mechanoenzymatic reaction with a fatty acid, preferably in an extruder.