surfactants

Abstract

The present invention relates to compounds derivable from the esterification of aliphatic alcohols with furoic acid according to formula (I). The present invention also relates to the use of said compounds as surfactants, compositions containing said compounds, and the preparation of said compounds.

Description

[Technical Field]

[0001] The present invention relates to compounds that can function as surfactants, their use in cleaning agents, and the preparation of said compounds. [Background technology]

[0002] Surfactants are among the most widely used chemical products, commercially available in large quantities and with applications in many different areas, such as household, industrial, agricultural, and personal care products. Due to the large quantities produced, sustainability in terms of raw materials used, synthesis procedures, biodegradability, and formulation are important parameters for assessing the success of surfactants.

[0003] Surfactant design is based on the selection of the chemical structures of the hydrophilic and hydrophobic portions of the surfactant compound. Surfactant evaluation can be achieved by assessing various parameters, such as critical micelle concentration (CMC), Kraft temperature (KP), hard water resistance, foaming ability, solubility, emulsification properties, toxicity, and biodegradability. To achieve a good compromise between all these parameters, many known cleaning agents are formulations of different chemical compounds, where surfactants are the active ingredient, accounting for 15–40% of the formulation, and additives such as builders, chelating agents, and hydrotropes are included to optimize surfactant performance.

[0004] Linear alkylbenzene sulfonates (LAS) are widely used as surfactants in detergent applications, as described in Suri, SK; Thakur, MS; Bhardwaj, S.; J. Am. Oil Chem. Soc. 1993, 70(1), 59–64. https: / / doi.org / 10.1007 / BF02545368. However, to obtain detergent formulations with suitable cleaning properties, LAS must be blended with additives. Some of the additives required to adjust the properties of LAS are considered environmentally harmful. For example, sodium tripolyphosphate (STPP), ethylenediaminetetraacetic acid (EDTA), and sodium nitrilotriacetate are used to increase the hard water resistance of LAS, but are considered toxic to humans and / or aquatic life. Currently, other more environmentally friendly builders, such as zeolite or citric acid, are used, but these additives are more expensive and / or more difficult to incorporate into detergents.

[0005] Additionally, LAS is produced from non-renewable petroleum-based feedstocks. Therefore, bio-based sodium dodecyl sulfate (SDS), which can be produced from renewable resources such as palm kernel, coconut oil, or fatty acids, has been used as an alternative to LAS. However, SDS's utility has been limited by its poor performance in hard water, its high CMC, and, like LAS, the need for expensive and / or environmentally harmful additives to improve performance.

[0006] Alternative surfactants have been proposed in Gassama et al., Green Chem, 2013, 15, 1558-1566, Kraus and ee, J. Surfact. Deterg. (2013) 16:317-320, US20170226075 and US20180327375.

[0007] It remains desirable to provide new surfactants that have improved properties, such as those that are derivable from bio-renewable and / or low-cost feedstocks, that perform well in hard water, that have high solubility and / or low CMC, etc. It is also desirable that the new surfactants be capable of being formulated into cleaning products using fewer builders, chelants, and hydrotropes. Summary of the Invention [Problem to be solved by the invention]

[0008] The present disclosure relates to a novel class of surfactants derived from the esterification of fatty alcohols with furoic acids. [Means for solving the problem]

[0009] In a first aspect of the present invention, there is provided a compound of formula (I):

[0010] [ka]

[0011] (Wherein, R1 is

[0012] [ka]

[0013] X is a cation and R2 is an acyclic C8-C 18 aliphatic groups) is provided.

[0014] A second aspect of the present invention relates to the use of a compound of formula (I) as a surfactant.

[0015] In a third aspect, the present invention provides a composition comprising a compound of formula (I), wherein the composition is a cleaning composition, a personal care composition, an oil recovery composition, a pharmaceutical composition, an agricultural composition or a paint composition.

[0016] In a fourth aspect, the present invention provides a compound of formula (Ia):

[0017] [ka]

[0018] 1. A method for producing a) a compound of formula (II):

[0019] [ka]

[0020] with a sulfonating agent; and b) adding a base to form a compound of formula (Ia) wherein X and R2 are as defined in the first aspect of the invention.

[0021] In a fifth aspect, the present invention provides a compound of formula (Ib):

[0022] [ka]

[0023] 1. A method for producing a) a compound of formula (II):

[0024] [ka]

[0025] with a carboxylating agent, and b) adding an acid to form a compound of formula (Ib) wherein X and R2 are as defined in the first aspect of the invention.

[0026] In a sixth aspect, the present invention provides a composition comprising a compound of formula (I) and sodium dodecyl sulfate.

[0027] In a seventh aspect, the present invention provides a compound of formula (II) wherein R2 is as defined in the first aspect of the invention.

[0028] In an eighth aspect, the present invention provides a compound of formula (II):

[0029] [ka]

[0030] 1. A method for producing Furoic acid can be reacted with a compound of formula (III):

[0031] [ka]

[0032] wherein R2 is as defined in the first aspect of the invention, optionally in the presence of an acid.

[0033] In a ninth aspect, the present invention provides a compound of formula (II):

[0034] [ka]

[0035] 1. A method for producing Furfural can be converted into a compound of formula (III):

[0036] [ka]

[0037] wherein R2 is as defined in the first aspect of the present invention, in the presence of an oxygen source and a catalyst. The present invention provides a method comprising: [Brief explanation of the drawings]

[0038] [Figure 1] - Surface tension measurements at various concentrations - A graph showing the change in surface tension of aqueous solutions of various surfactants as a function of surfactant concentration. [Figure 2] - Droplet formation of water / surfactant solutions in octanol performed at a concentration of surfactant twice the CMC - Images of the drop experiment used to measure the surface tension of surfactant solutions in octanol. [Figure 3] 1 is a graph showing the amount of dodecyl furoate obtained from the reaction between dodecanol and furoic acid in the presence of various catalysts. [Figure 4] 1 is a graph showing how the rate of production of dodecyl furoate is affected by the amount of sulfuric acid catalyst present in the reaction. [Figure 5] 1 is a graph showing how the rate at which octyl furoate is sulfonated by chlorosulfonic acid is affected by reaction temperature. DETAILED DESCRIPTION OF THE INVENTION

[0039] In a first aspect of the present invention, there is provided a compound of formula (I):

[0040] [ka]

[0041] (Wherein, R1 is

[0042] [ka]

[0043] X is a cation and R2 is an acyclic C8-C 18 aliphatic groups) is provided.

[0044] In the compound of formula (I), X is a cation. X may be an alkali metal cation, an alkaline earth metal cation, or an ammonium cation. X may be a sodium cation, a potassium cation, a lithium cation, a calcium cation, a magnesium cation, or an ammonium cation. X may be an alkali metal cation, such as a sodium cation or a potassium cation.

[0045] R2 is acyclic C8-C 18 R2 is a saturated acyclic C8-C 18 Aliphatic groups, e.g., C8-C 18 R2 may be an unsaturated acyclic C8-C 18 Aliphatic groups, e.g., C8-C 18 R2 may be a linear C8-C 18 Therefore, R2 may be a linear C8-C 18 R2 may alternatively be a branched C8-C 18 R2 may also be an unsaturated linear C8-C 18 It may be an aliphatic group.

[0046] R2 contains 8 to 18 carbon atoms. R2 may contain 8 to 16 carbon atoms. R2 is, for example, a C8 aliphatic group, C 12 Aliphatic group or C 16 In fact, R2 may be a linear C8 alkyl group, a linear C 12 Alkyl group or linear C 16 It may be an alkyl group.

[0047] R1 is

[0048] [ka]

[0049] Thus, the compound of formula (I) is a compound of formula (Ia):

[0050] [ka]

[0051] (wherein R2 is the acyclic C8-C 18 The compounds of formula (I) also include compounds of formula (Ib):

[0052] [ka]

[0053] (wherein R2 is the acyclic C8-C 18 aliphatic groups).

[0054] Exemplary compounds of formula (I) are:

[0055] [ka]

[0056] Includes.

[0057] In a second aspect, the present invention relates to the use of the compound of the first aspect of the present invention as a surfactant. The compound of the first aspect, or a mixture of compounds of the first aspect, can be used as a surfactant. The compound of the first aspect of the present invention can be used in a cleaning composition. The compound of the first aspect of the present invention can be used to remove contaminants from surfaces. Exemplary surfaces include ceramic, metal, glass, plastic, fabric, or some combination thereof.

[0058] A third aspect of the present invention relates to providing a compound of the first aspect in a cleaning composition. Accordingly, the cleaning composition may comprise a compound of the first aspect or a mixture of two or more compounds. The cleaning composition may also comprise a carrier and / or one or more additives. For example, the cleaning composition may also comprise one or more builders, chelating agents, or hydrotropes, and combinations thereof. Exemplary builders include zeolites and citric acid. Exemplary chelating agents include sodium tripolyphosphate (STPP), ethylenediaminetetraacetic acid (EDTA), and sodium nitrilotriacetate. Exemplary hydrotropes include urea, tosylates (such as the sodium or potassium salts of toluenesulfonic acid), cumenesulfonates (such as the sodium or ammonium salts of cumenesulfonic acid), and xylenesulfonates (such as the potassium, calcium, or ammonium salts of xylenesulfonic acid). The cleaning composition may be free of hydrotropes. Any of these additives may be included in the final formulation to further enhance the properties of the cleaning agent. In addition to their use in cleaning agents, the compounds of the first aspect may be used as part of personal care compositions, oil recovery compositions, pharmaceutical compositions, drug delivery compositions, agricultural compositions, coating compositions, or paint compositions. The compounds of the first aspect may be used in any formulation or process requiring emulsification (e.g., radical polymerization processes).

[0059] A composition may be provided which comprises a mixture of two or more compounds of the first aspect.

[0060] Mixtures of compounds of the first embodiment that may be provided for use as surfactants and / or in cleaning compositions may contain two or more compounds of the first embodiment. Mixtures of two or more compounds of the first embodiment may also be provided in personal care compositions, oil recovery compositions, pharmaceutical compositions, drug delivery compositions, agricultural compositions, coating compositions, or paint compositions. In such mixtures, the two or more compounds may have R2 groups of different chain lengths. Mixtures may also be provided where R2 is an acyclic C8-C 11 The compound of the first aspect is aliphatic, and R2 is acyclic C 12 ~C 18 The mixture may include a compound of the first embodiment where R2 is acyclic C8 aliphatic, and a compound of the first embodiment where R2 is acyclic C8 aliphatic. 12 ~C 18 The mixture may include compounds of the first aspect where R2 is a linear or branched C8 alkyl (e.g., linear C8 alkyl), and compounds where R2 is a linear or branched C8 alkyl. 12 ~C 18 Alkyl (e.g., linear C 12 ~C 18 The mixture may include compounds where R2 is a linear or branched C8 alkyl (e.g., a linear C8 alkyl), and compounds where R2 is a linear or branched C8 alkyl. 12 ~C 18 Alkyl (e.g., linear C 12 ~C 18 The mixture may include compounds where R2 is a linear or branched C8 alkyl (e.g., a linear C8 alkyl), and compounds where R2 is a linear or branched C8 alkyl. 12 or C 16 Alkyl (e.g., linear C 12 or C 16 The mixture may include compounds where R2 is a linear or branched C8 alkyl (e.g., a linear C8 alkyl), and compounds where R2 is a linear or branched C8 alkyl. 12 Alkyl (e.g., linear C 12 alkyl).

[0061] The mixture is

[0062] [ka]

[0063] Mixtures of two or more of the following, for example:

[0064] [ka]

[0065] Any of the above mixtures may contain the two compounds in a weight ratio of about 2:1 to 1:2, for example about 1:1.

[0066] Synthesis of Compounds of Formula (I) Compounds of formula (I) may be prepared by the following synthetic route:

[0067] [ka]

[0068] (wherein R1 and R2 are as defined above).

[0069] Thus, a fourth aspect of the present invention provides a compound of formula (Ia):

[0070] [ka]

[0071] 1. A method for producing a) a compound of formula (II):

[0072] [ka]

[0073] with a sulfonating agent; and b) adding a base to form a compound of formula (Ia) wherein X and R2 are as described above.

[0074] Step a) of the method involves contacting the compound of Formula (II) with a sulfonating agent. The sulfonating agent may be pyridine / sulfur trioxide complex, oleum, sulfur trioxide, or chlorosulfonic acid. The sulfonating agent (e.g., chlorosulfonic acid) may be provided in at least a stoichiometric amount (1:1 molar ratio) relative to the amount of the compound of Formula (II). The sulfonating agent (e.g., chlorosulfonic acid) may be provided in excess relative to the amount of the compound of Formula (II). For example, the sulfonating agent (e.g., chlorosulfonic acid) may be provided in an amount of 1.05 or more equivalents relative to the amount of the compound of Formula (II).

[0075] Step a) may be carried out with or without a solvent. When a solvent is used, chloroform may be used as the solvent. Liquid sulfur dioxide may also be used as the solvent, for example, liquid sulfur dioxide may be used as the solvent together with solubilized sulfur trioxide as the sulfonating agent.

[0076] Step a) may be carried out at a temperature of 20° C. or higher. For example, a temperature of 60° C. or higher may be used, a temperature in the range of 60° C. to 80° C. may be used, or a temperature in the range of 60° C. to 70° C. may be used.

[0077] Step b) of the process requires the addition of a base to obtain the compound of formula (Ia) as a salt in the form suitable for use as a cleaning agent. The base may be added to achieve neutralization, for example, to reach a pH of 7 or higher. Suitable bases include alkali metal hydroxides or alkali metal carbonates. Suitable alkali metal hydroxides include sodium hydroxide or potassium hydroxide. Suitable alkali metal carbonates include sodium carbonate or potassium carbonate.

[0078] A fifth aspect of the present invention relates to a compound of formula (Ib):

[0079] [ka]

[0080] 1. A method for producing a) a compound of formula (II):

[0081] [ka]

[0082] with a carboxylating agent, and b) adding an acid to form a compound of formula (Ib) wherein X and R2 are as described above.

[0083] Step a) of the process requires contacting a compound of formula (II) with a carboxylating agent. The carboxylating agent may be carbon dioxide. This reaction may be enhanced by providing a mixture of i) a compound of formula (II), ii) carbon dioxide, and iii) an alkali metal carbonate or alkaline earth metal carbonate, or a combination thereof. For example, component iii) may be potassium carbonate or cesium carbonate, or a combination thereof. Step a) may be carried out at a temperature ranging from about 200 to about 300°C and a pressure of about 8 bar to about 40 bar.

[0084] Step b) of the process requires the addition of an acid to obtain the compound of formula (Ia) as a salt in the form in which it is provided for use as a cleaning agent. The acid may be added to achieve neutralization, for example to reach a pH of 7 or less.

[0085] The method for making a compound according to formula (Ia) or formula (Ib) can also include first preparing a compound of formula (II). This can be achieved by forming an ester between an aliphatic alcohol and a furan derivative. For example, a compound of formula (II) can be prepared by converting furoic acid to a compound of formula (III):

[0086] [ka]

[0087] (wherein R2 is an acyclic C8-C 18 The compound may be prepared by contacting a carboxylic acid with a carboxylic acid group (which is an aliphatic group) optionally in the presence of an acid as a catalyst.

[0088] The reaction may be carried out using an excess of furoic acid relative to the amount of compound of formula (III) provided. For example, the furoic acid may be provided in an amount of 1.2 or more equivalents relative to the amount of compound of formula (III). Alternatively, the reaction may be carried out using an excess of compound of formula (III) relative to the amount of furoic acid provided.

[0089] The process may be carried out in the presence of an acid catalyst. The acid catalyst may be a Lewis acid or a Bronsted acid. The acid may be provided in an amount of 0.1 to 10.0 mol %, for example, 0.1 to 5.0 mol %, 0.1 to 2.0 mol %, 0.1 to 1.0 mol %, or 1.0 to 2.0 mol %, based on the amount of the compound of formula (III) provided.

[0090] The acid may be sulfuric acid or a polymer containing sulfonic acid functional groups (well-known examples include Nafion, Aberlyst-15, or Purolite-C450). The acid may be sulfuric acid provided in an amount of 1.0 to 2.0 mol % relative to the amount of compound of formula (III) provided.

[0091] The process may be carried out in the absence of an acid, for example, the process may be carried out at a temperature of 160° C. or greater without a solvent and without an acid.

[0092] The reaction may be carried out with or without a solvent. When the reaction is carried out without a solvent, the reaction may be carried out at a temperature high enough to solubilize the compound of formula (III) in the provided furoic acid. For example, a temperature of 120°C or higher may be used, or a temperature of 140°C or higher may be used, or a temperature in the range of 140°C to 160°C may be used. When the reaction is carried out with a solvent, an aprotic organic solvent may be used. When a solvent is used, the reaction may be carried out at a temperature of 60°C or higher.

[0093] An alternative method for preparing a compound of formula (II) is to convert furfural into a compound of formula (III):

[0094] [ka]

[0095] (wherein R2 is an acyclic C8-C 18 aliphatic groups) in the presence of an oxygen source and a catalyst.

[0096] In this method, a suitable oxygen source may be di-tert-butyl peroxide, hydrogen peroxide, gaseous oxygen, or air. A suitable catalyst may include a noble metal or transition metal. The noble metal or transition metal may be zerovalent or may be part of a metal complex. Suitable noble metal or transition metal complexes include noble metal carbenes or transition metal carbenes. The noble metal or transition metal may be used as a catalyst in bulk or supported on another material. Suitable supports may include carbon, titania, zeolite, or zirconia. Suitable noble metals or transition metals include gold, palladium, platinum, ruthenium, manganese, cobalt, or vanadium. Compositions comprising a compound of formula (I) and sodium dodecyl sulfate (SDS) It has been found that when the compound of formula (I) is provided as part of a mixture with sodium dodecyl sulfate (SDS), the mixture exhibits enhanced aqueous solubility.

[0097] Thus, a sixth aspect of the present invention provides a composition comprising a compound of formula (I) as defined above and SDS. The composition may be provided in various ratios of the compound of formula (I) to SDS, for example, in a weight ratio of the compound of formula (I) to SDS of about 1:6 to about 6:1, respectively. The composition may be provided in a composition in which R1 is

[0098] [ka]

[0099] and R2 is a linear C 12 The compound of formula (I) may comprise an alkyl group, and SDS, wherein the weight ratio is about 6:1.

[0100] The composition comprises:

[0101] [ka]

[0102] and SDS, wherein the mass ratio is about 6:1.

[0103] Compound of formula (II) A seventh aspect of the present invention relates to a compound of formula (II):

[0104] [ka]

[0105] wherein R2 is as defined above. to provide.

[0106] Thus, an eighth aspect of the present invention provides a compound of formula (II):

[0107] [ka]

[0108] 1. A method for producing Furoic acid can be reacted with a compound of formula (III):

[0109] [ka]

[0110] wherein R2 is as defined in the first aspect of the invention, optionally in the presence of an acid. Conditions that may be used to carry out this method are those described above in relation to the fourth and fifth aspects of the invention when the compound of formula (II) is obtained from furoic acid.

[0111] Similarly, a ninth aspect of the present invention relates to a compound of formula (II):

[0112] [ka]

[0113] 1. A method for producing Furfural can be converted into a compound of formula (III):

[0114] [ka]

[0115] wherein R2 is as defined in the first aspect of the invention, in the presence of an oxygen source and a catalyst. Conditions that may be used to carry out this method are those described above in relation to the fourth and fifth aspects of the invention when the compound of formula (II) is obtained from furfural.

[0116] As used herein, the term "aliphatic" includes both saturated and unsaturated non-aromatic hydrocarbons, which may be straight-chain (i.e., unbranched), branched, acyclic, cyclic, or combinations thereof. The term "aliphatic" includes alkyl, alkenyl, alkynyl, cycloalkyl, and cycloalkenyl moieties. As used herein, the term "acyclic" includes both saturated and unsaturated hydrocarbons, which may be straight-chain or branched. Unsaturated acyclic aliphatic moieties contain one or more carbon-carbon double or triple bonds. The term "acyclic aliphatic" includes straight-chain or branched alkyl (fully saturated), alkenyl (containing at least one carbon-carbon double bond), or alkynyl (containing at least one carbon-carbon triple bond) moieties.

[0117] As used herein, the term "sulfonating agent" refers to a reagent that can be used to impart a sulfonic acid group to an organic compound. As used herein, the term "carboxylating agent" refers to a reagent that can be used to impart a carboxylic acid group to an organic compound.

[0118] As used herein, the term "ammonium cation" refers to [NH4] + Cation, primary ammonium cation ([NH3R] + ), secondary ammonium cation ([NH2R]2 + ), tertiary ammonium cation ([NHR3] + ) or quaternary ammonium cation ([NR4] + Each R may independently be a hydrocarbon, such as an aliphatic hydrocarbon, an aromatic hydrocarbon, or a hydrocarbon containing both aliphatic and aromatic moieties. The aliphatic hydrocarbon may be, for example, an alkyl group. The alkyl group may be, for example, a C1-C 18 Alkyl groups, C1-C 12It may be an alkyl group or a C1-C6 alkyl group. When R comprises an aromatic group, for example when R is a phenyl group or a benzyl group, the aromatic group may be optionally substituted, for example with one or more halogens (e.g., fluorine, chlorine, bromine, or iodine), or one or more alkyl groups.

[0119] The term "about" is used herein to mean approximately, within a range, roughly, or around. When the term "about" is used in connection with a numerical range, it modifies that range by extending to the upper and lower boundaries of the stated numerical range. In general, the term "about" is used herein to modify a numerical value above and below the stated value by a variance of 10%.

[0120] Throughout the description and claims of this specification, the words "comprise" and "contain," as well as variations of words such as "comprising" and "comprises," mean "including but not limited to," and are not intended to (and do not) exclude other components. In any of the embodiments described herein, reference to "comprising" also encompasses "consisting essentially of" and "consisting of."

[0121] The present disclosure will now be described in more detail by reference to the following non-limiting examples. [Example]

[0122] Abbreviation: LAS = Linear alkylbenzene sulfonate SDS = sodium dodecyl sulfate; SDBS = sodium dodecylbenzenesulfonate; SAF = alkyl sulfonated furoate material: Furoic acid (98%), 1-octanol (>99%), 1-dodecanol, 1-hexadecanol (99%), oleum (20% SO), chlorosulfonic acid (99%), sulfur trioxide pyridine complex (97%), pharmaceutical grade sodium dodecylbenzenesulfonate (SDBS), and sodium dodecyl sulfate were obtained from Sigma-Aldrich. Octyl furoate (>97%) was obtained from TCI. Dichloromethane (DCM), chloroform, and sulfuric acid (5 M) were obtained from VWR. Chloroform was purified from ethanol by washing with water (three times in a 3:1 ratio) and distilled over phosphorus pentoxide in a distillation column. Solvents were stored in dark containers to avoid decomposition. Unless otherwise noted, all other chemicals were used without purification. [Example]

[0123] Synthesis of octyl furoate Octanol (100 g, 0.768 mol, 1 equiv.) was mixed with furoic acid (103.3 g, 0.926, 1.2 equiv.) in a round-bottom flask, followed by the addition of sulfuric acid (1 mol% relative to octanol, 1.54 ml). The reaction was heated to 140 °C and left until the alcohol was completely consumed (4-5 h). The reaction mixture was diluted with DCM (200 ml) and filtered to remove by-products and unreacted furoic acid. The organic phase was washed with water (400 ml) to remove residual acidity until a neutral pH was reached. Because an emulsion could not be broken down by centrifugation, the addition of sodium chloride or ethanol during washing was necessary to separate the phases. The solvent was removed under vacuum to yield the crude product (90% yield). The product was further purified by distillation under vacuum over activated carbon.

[0124] Octyl furoate: 1 H NMR (DMSO-d6): δ 8 (m, -CC H -O-, ), 7.3, 6.7 (mx 2, 2 x 1H, 2 x CC H -C), 4.23 (t, 2H, OC H2 -CH2 , J HH=6.6 Hz), 1.66, 1.4-1.8 (m, CH2 alkyl chain), 0.86 (m, CH2-CH3). 13 C{ 1 H} NMR (DMSO-d6): δ 159.9 (C=O), 147.8 (CH- C -C=O), 144.6 (O- C H-CH), 119, 113 (-CC H -C H -C), 65 (O- C H2-CH2), 31.7,31.1,29.1,28.7,25.8,22.7 (6 XC, C- C H2-C), 14.4 (-CH2- C H3) ppm. MS (ES, negative mode): m / z = 225.1486. ​​FT-IR: 1705 cm -1 (OC=O expansion / contraction). [Example]

[0125] Synthesis of sulfonated octyl furoate (SAF-8) Octyl furoate (30 g, 0.134 mol) was added to dry chloroform (1 L) and mixed at room temperature until complete dissolution was achieved. The reaction flask was then connected to a bubbler filled with water, through which the generated HCl was vented. Chlorosulfonic acid (CSA) was then added (16.6 g, 0.140 mol, 1.05 equiv.). The reaction was left until no more bubbling was observed in the bubbler, and then 1Analysis by H NMR spectroscopy confirmed the reaction was complete, with complete conversion of the ester and the majority of the CSA reacting (CSA shift: 10.9 ppm). The chloroform was removed under vacuum to give a green solution, which was diluted with water and neutralized to pH 7 with sodium hydroxide solution. The water was then removed under vacuum to give the crude product as a black solid. The product required purification by dissolving in dichloromethane, filtering, and then washing three times with diethyl ether (200 ml) to remove residual sodium sulfate salts (formed by neutralization of excess chlorosulfonic acid) and impurities responsible for the dark color. After washing, the surfactant was obtained as a white powder (70% yield).

[0126] Sulfonated Octyl Furoate: 1 H NMR (D2O): 6.9, 6.7 (mx 2, 2 x 1H, 2 x CC H -C), 4.2 (t, 2H, OC H2 -CH2 , J HH =6.6 Hz), 1.6, 1.34-1.0 (m, CH2 alkyl chain), 0.8 (m, CH2-CH3). 13 C{ 1 H} NMR (D2O): δ158.5 (C=O), 155.8(O- C H-CH,) 144.5 (CH- C -C=O), 118.2-112.2 (-CC H -C H -C), 66.1 (O- C H2-CH2), 31.7,29.2,29.1.2,28.3,25.7,22.6 (6 XC, C- C H2-C), 13.8 (-CH2- C H3) ppm. MS (ES, negative mode): m / z (abundance) = 303.087 (C 13 H 19 O6S - 100%). FT-IR: 1250-1300 cm-1, S=O stretching), 1705 cm -1 (OC=O expansion / contraction). [Example]

[0127] Synthesis of dodecyl furoate Dodecanol (100 g, 0.54 mol, 1 equiv.) was mixed with furoic acid (72.58 g, 0.648, 1.2 equiv.) in a round-bottom flask, followed by the addition of sulfuric acid (1 mol% relative to dodecanol, 1.08 ml). The reaction was heated to 140 °C and left until the alcohol was completely consumed (4-5 h). The reaction mixture was diluted with DCM (200 ml) and filtered to remove by-products and unreacted furoic acid. The organic phase was washed with water (400 ml) to remove residual acidity until a neutral pH was reached. Because an emulsion could not be broken down by centrifugation, the addition of sodium chloride or ethanol during washing was necessary to separate the phases. The solvent was removed under vacuum to yield the crude product (87% yield). The product was further purified by distillation under vacuum over activated carbon.

[0128] Dodecyl furoate: 1 H NMR (DMSO-d6): δ 7.9 (m, -CC H -O-, ), 7.2, 6.7 (mx 2, 2 x 1H, 2 x CC H -C), 4.23 (t, 2H, OC H 2-CH 2, J HH =6.6 Hz), 1.66, 1.4-1.8 (m, C H 2 alkyl chains), 0.86 (m, CH2-C H 3). 13 C{ 1 H} NMR (DMSO-d6): δ159.9 (C=O), 148.2 (CH- C -C=O), 144.5 (O- C H-CH), 119, 112.5 (-CC H -C H -C), 65.7 (O- C H2-CH2), 31.8,29.5,29.2,29.7,28.8,25.9,22.6 (8 XC, C- C H2-C), 14.1 (-CH2-C H3) ppm. MS (ES, negative mode): m / z = 281.2109. FT-IR: 1705 cm -1 (OC=O expansion / contraction). [Example]

[0129] Synthesis of sulfonated dodecyl furoate (SAF-12) Dodecyl furoate (30 g, 0.107 mol) was added to dry chloroform (1 L) and mixed at room temperature until complete dissolution was achieved. The reaction flask was then connected to a bubbler filled with water, through which the generated HCl was vented. Chlorosulfonic acid (CSA) was then added (13.1 g, 0.112 mol, 1.05 equiv.). The reaction was left until no more bubbling was observed in the bubbler, and then 1 Analysis by H NMR spectroscopy confirmed the reaction was complete, with complete conversion of the ester and the majority of the CSA reacting (CSA shift: 10.9 ppm). The chloroform was removed under vacuum to give a green solution, which was diluted with water and neutralized to pH 7 with sodium hydroxide solution. The water was then removed under vacuum to give the crude product as a black solid. The product required purification by dissolving in dichloromethane, filtering, and then washing three times with diethyl ether (200 ml) to remove residual sodium sulfate salts (formed by neutralization of excess chlorosulfonic acid) and impurities responsible for the dark color. After washing, the surfactant was obtained as a white powder (64% yield).

[0130] Dodecyl furoate: 1 H NMR (DMSO-d6): δ 7.9 (m, -CC H -O-, ), 7.2, 6.7 (mx 2, 2 x 1H, 2 x CC H -C), 4.23 (t, 2H, OC H 2-CH 2, J HH =6.6 Hz), 1.66, 1.4-1.8 (m, C H 2 alkyl chains), 0.86 (m, CH2-C H 3). 13C{ 1 H} NMR (DMSO-d6): δ159.9 (C=O), 148.2 (CH- C -C=O), 144.5 (O- C H-CH), 119, 112.5 (-CC H -C H -C), 65.7 (O- C H2-CH2), 31.8,29.5,29.2,29.7,28.8,25.9,22.6 (8 XC, C- C H2-C), 14.1 (-CH2- C H3) ppm. MS (ES, negative mode): m / z (abundance) = 359.0865 (C 17 H 27 O6S - 100%). FT-IR: 1100-1300 cm-1, S=O stretching), 1705 cm -1 (OC=O expansion / contraction). [Example]

[0131] Synthesis of hexadecyl furoate Hexadecanol (100 g, 0.412 mol, 1 equiv.) was mixed with furoic acid (55.4 g, 0.495, 1.2 equiv.) in a round-bottom flask, followed by the addition of sulfuric acid (1 mol% relative to hexadecanol, 0.824 ml). The reaction was heated to 140 °C and left until the alcohol was completely consumed (4-5 h). The reaction mixture was diluted with DCM (200 ml) and filtered to remove by-products and unreacted furoic acid. The organic phase was washed with water (400 ml) to remove residual acidity until a neutral pH was reached. Because the emulsion could not be broken down by centrifugation, the addition of sodium chloride or ethanol during washing was necessary to separate the phases. The product was crystallized from DCM at -20 °C to yield a white powder (89% yield).

[0132] Hexadecyl furoate: 1 H NMR (benzene-d6): δ 7.0, 6.9 (mx 2, 2 x 1H, 2 x CC H -C), 5.8 (m, -CC H-O-, ), 4.1 (t, 2H, OC H2 -CH2 , J HH =6.7 Hz), 1.44, 1.37-1.05 (m, CH2 alkyl chain), 0.85 (m, CH2-CH3). 13 C{ 1 H} NMR (benzene-d6): δ 158.5 (C=O), 145.7 (CH- C -C=O), 145.5 (O- C H-CH), 117, 111 (-CC H -C H -C), 64.4 (O- C H2-CH2), 32,29.9-29.3,28.8,26,23 (6 XC, C- C H2-C), 14.1 (-CH2- C H3) ppm. MS (ES, negative mode): m / z = 337.2735. FT-IR: 1705 cm -1 (OC=O expansion / contraction). [Example]

[0133] Synthesis of sulfonated hexadecyl furoate (SAF-16) Hexadecyl furoate (30 g, 0.0892 mol) was added to dry chloroform (1 L) and mixed at room temperature until complete dissolution was achieved. The reaction flask was then connected to a bubbler filled with water, through which the generated HCl was vented. Chlorosulfonic acid (CSA) was then added (10.9 g, 0.09366 mol, 1.05 equiv.). The reaction was left until no more bubbling was observed in the bubbler, and then 1Analysis by H NMR spectroscopy confirmed the reaction was complete, with complete conversion of the ester and the majority of the CSA reacting (CSA shift: 10.9 ppm). The chloroform was removed under vacuum to give a green solution, which was diluted with water and neutralized to pH 7 with sodium hydroxide solution. The water was then removed under vacuum to give the crude product as a black solid. The product was washed with a small amount of water to remove sulfate by taking advantage of the low solubility of this surfactant in the aqueous phase. THF proved efficient in removing impurities, leaving the surfactant as a white powder.

[0134] Sulfonated hexadecyl furoate: 1 H NMR (D2O): δ 6.9, 6.7 (mx 2, 2 x 1H, 2 x CC H -C), 4.1 (t, 2H, OC H2 -CH2 , J HH =6.4 Hz), 1.54, 1.26-0.95 (m, CH2 alkyl chain), 0.8 (m, CH2-C H 3). 13 C{ 1 H} NMR (D2O): δ159.5 (C=O), 156.5(O- C H-CH,) 144.6 (CH- C -C=O), 118.9-112.9 (-CC H -C H -C), 66.1 (O- C H2-CH2), 32.2, 31-29.3,28.5, 26,22.8 (10 XC, C- C H2-C), 13.8 (-CH2- C H3) ppm. MS (ES, negative mode): m / z (abundance) = 415.1465 (C 21 H 35 O6S - 100%). FT-IR: 1100-1300 cm-1, (S=O stretching), 1705 cm -1 (OC=O expansion / contraction). [Example]

[0135] Solubility Test Solubility tests for various surfactants were performed according to ISO standard 6839 (Determination of Solubility in Water). In a typical test, duplicate 20 ml solutions containing surfactant concentrations ranging from 12.5 to 22.5% w / w were prepared and heated to complete dissolution using a temperature-controlled hot plate. 10 ml of the solution was poured into a 20 ml vial and allowed to cool until precipitation was observed. Another 10 ml of the solution was poured into a 20 ml vial and held at a higher temperature. Samples that precipitated were slowly heated, and transparent samples were slowly cooled. The temperature at which a change in appearance occurred was considered the temperature of solubility at a particular surfactant concentration. The results of the solubility tests are reported in Table 1.

[0136] [Table 1]

[0137] Commercially available SDBS proved to have the lowest solubility due to the extensive hydrophobicity imparted by the benzene ring, while SDS achieved a higher solubility of 10–15% at room temperature. Although SDS has a higher solubility than SDBS, it still requires the addition of a hydrotrope to increase its solubility during use. Significant improvements were achieved by modifying the furan head group with an ester bond, particularly in SAF-8, where high solubility was achieved at very low temperatures. SAF-8 could be solubilized at concentrations up to 140% at room temperature. SAF-12 was soluble at 20% at 24°C but precipitated at temperatures below 20°C. The effect of the alkyl chain became apparent in SAF-16, which was found to have very low solubility. 0.05% SAF-16 was soluble in the aqueous phase at room temperature. SAF-8 can be used as a detergent without the addition of a hydrotrope, while SAF-16 can be used with a hydrotrope. SAF-12 can be used as a detergent alone, i.e., without the addition of a hydrotrope, in hot water applications, or with the addition of a hydrotrope in cold water applications. Mixtures with SAF-8 can improve the solubility of higher alkyl chain SAFs. For example, a mixture of 20% SAF-8 and 20% SAF-12 showed solubility at temperatures up to 7°C. [Example]

[0138] Hard water resistance These measurements were performed according to the standard protocol reported in ISO Standard 1063. Calcium chloride concentrations of 6, 9, and 12 mEq Ca / L (3.0, 4.5, and 6.0 mM) were used as the cation source. Surfactant mother solutions were prepared in water at 20°C at a concentration of 50 mg / ml. Defined aliquots of the mother solution were transferred to 50 ml Falcon tubes and diluted to 50 ml with calcium solution. Five different aliquots of surfactant mother solution were tested: 5.0, 2.5, 1.2, 0.6, and 0.3 ml. For all tests, the samples were visually inspected and assigned a score according to Table 2. The scores of 15 tests for each surfactant were summed, and the final results were expressed as average stability according to Table 3.

[0139] [Table 2]

[0140] A milky solution is one that is not transparent but allows objects to be seen in. A turbid solution is one that is not transparent and does not allow objects to be seen through.

[0141] [Table 3]

[0142] The results of the stability tests are reported in Table 4. SDBS and SDS proved to have very poor tolerance to hard water, showing extensive precipitation in many tests. On the other hand, SAF-8 and SAF-12 showed very good solubility, with solutions remaining clear at all different calcium concentrations.

[0143] [Table 4] [Example]

[0144] Critical micelle concentration in air-water-surfactant systems The surface tension of water-surfactant solutions was evaluated at concentrations ranging from 10 ppm to 12,500 ppm. The concentration evaluated for each surfactant varied depending on the surfactant's solubility and the surface tension reduction observed during the analysis. Experiments were performed at 25°C. Deionized water (prepared using a Milli-Q system (Merck)) was used for each experiment.

[0145] Surface tension was calculated using the pendant drop method with a Kruss DSA25. A drop of solution was generated on the tip of a blunt metal needle (1.25 mm) until the drop reached its maximum size. After equilibration for 10–15 seconds, images of the drop were captured using a digital camera. The drop was analyzed using the Kruss Easy Drop Standard - Drop Shape Analysis (DSA1) v1.92 software. The software uses the Young-Laplace equation to calculate surface tension as a function of drop deformation, taking into account the effects of gravity and hydrostatic pressure.

[0146] The critical micelle concentration (CMC) was obtained after plotting surface tension versus surfactant concentration. The CMC is calculated as the surfactant concentration at which the initial line intersects the plateau of the graph. The CMC results are summarized in Table 5. The results show that the alkyl chain has a significant effect, lowering the CMC by approximately five times for every four carbon atoms added. A CMC of less than 2000 ppm is desirable for many commercial applications. The CMC can be improved by using a mixture of surfactants and SAF-8, resulting in an optimal balance between CMC and solubility as previously reported.

[0147] [Table 5] [Example]

[0148] Surface tension measurements in octanol-water-surfactant systems The drop volume method was used to calculate the surface tension in the system according to ISO standard 9101 with some modifications. In each experiment, a syringe connected to a Kruss DSA25 drop shape analyzer was used to slowly form a droplet of an aqueous surfactant solution on the tip of a needle (d = 1.82 mm) immersed in octanol. The droplet formation was allowed to grow as close as possible to the maximum volume at which it would detach from the needle. At this point, the droplet was allowed to stabilize for 2 minutes and then detached from the needle by adding a small amount of additional solution. A camera connected to the Kruss DSA25 was used to take a photograph of the droplet detaching from the needle. The diameter of the droplet was measured, and the surface tension was calculated using the following equation:

[0149]

number

[0150] (where γ is the surface tension (mN / m) and V is the droplet volume (cm 3 ), and Δρ is the density difference between water and octanol (g / cm 3 ), and g is the acceleration due to gravity (cm / s 2 ), d is the outer diameter of the needle (cm), and f is a correction factor calculated using the following formula:

[0151]

number

[0152] Table 6 summarizes the surface tensions of the two-fold concentration of CMC in deionized water (prepared using a Milli-Q system (Merck)). It is noteworthy that water in octanol exhibits a surface tension of 7.45 ± 1.10 mN / cm, indicating that lower surface tension favors the formation of stable emulsions and therefore corresponds to better cleaning performance. Figure 2 reports the droplet formation of water / surfactant solutions in octanol for SAF-8, SAF-12, and SDBS at surfactant concentrations twice that of CMC. SAF-8 exhibits a lower surface tension (2.65 ± 0.32 mN / cm), primarily due to the use of a higher surfactant concentration. SAF-12 exhibits a lower surface tension (3.42 ± 0.58 mN / cm) compared to SDBS (4.48 ± 0.75 mN / cm), indicating that these surfactants have enhanced cleaning performance.

[0153] [Table 6]

[0154] Additionally, surface tension was evaluated using hard water (500 ppm CaCl), and the results are summarized in Table 7. SAF-8 was evaluated using a concentration twice its CMC, and SAF-12 was evaluated at concentrations 2, 4, and 8 times its CMC. Surprisingly, SAF-8 and SAF-12 still strongly reduce surface tension in hard water, while SDS and SDBS show significant aggregation.

[0155] [Table 7] [Example]

[0156] Screening of catalysts for the synthesis of alkyl furoates To identify an acid catalyst for use in converting furoic acid to alkyl furoates according to formula (II), different catalysts were tested using the following procedure.

[0157] A 3 ml vial was charged with stoichiometric amounts of furoic acid and dodecanol (500 mg furoic acid, 830 mg dodecanol) at room temperature. The catalyst was then added to the vial (1 mol% in the case of sulfuric acid, or 300 mg in the case of polymer-based catalysts such as Nafion or Amberlyst). The vial was placed in a preheated heating block at 150 °C for 1.5 hours. The yield of dodecyl furoate and the degree of conversion of dodecanol were analyzed by GC-MS-FID using naphthalene as an internal standard.

[0158] The results of these experiments are shown in Figure 3. The results show that dodecyl furoate was obtained from each catalyst. When sulfuric acid or Nafion was used, nearly complete conversion of the starting material was observed, resulting in high yields of dodecyl furoate. [Example]

[0159] Optimization of the amount of catalyst used in the synthesis of alkyl furoates. To optimize the process for producing alkyl furoates according to formula (II), the conversion of furoic acid and dodecanol to dodecyl furoate was monitored in the presence of different amounts of sulfuric acid catalyst.

[0160] In each experiment, 500 mg of furoic acid was mixed with a stoichiometric amount of dodecanol (830 mg) and a fixed amount of sulfuric acid (0.41, 1, 1.5, or 2 mol%). The reaction mixture was placed in a preheated heating block at 150 °C for 1.5 h. The yield of dodecyl furoate was analyzed by GC-MS-FID using naphthalene as an internal standard.

[0161] The results of these experiments are shown in Figure 4. The results show that when 1 mol% to 2 mol% sulfuric acid was used, the reaction proceeded to completion within 1.5 hours. [Example]

[0162] Optimized method for preparing dodecyl furoate 1 kg (8.93 mol) of furoic acid was mixed with a stoichiometric amount of dodecanol (1.66 kg) and heated until the reaction mixture reached a temperature of 150 °C. 1 mol% of sulfuric acid was added. Water evolved during the reaction was collected using a Dean-Stark apparatus connected to a vacuum line with a pressure controller at 800 mbar. The reaction was carried out for 1.5 hours. The alkyl furoate was obtained as a yellowish liquid (99% yield). The dodecyl furoate product was confirmed by NMR and GC-MS. The residual furoic acid content was estimated to be less than 2% by HPLC. [Example]

[0163] Optimization of reaction temperatures for use in the sulfonation of alkyl furoates. To optimize the process for making surfactants according to formula (I), the sulfonation of octyl furoate with chlorosulfonic acid was monitored while varying the reaction temperature.

[0164] In each experiment, octyl furoate (500 mg, 2.24 mmol) was mixed with a stoichiometric amount of chlorosulfonic acid (260 mg, 2.24 mmol) at room temperature and immediately placed on a preheated heating block (60, 70, or 80 °C) with vigorous stirring. Samples (approximately 10 mg) were taken at regular intervals and diluted with water. The yield of SAF-8 was determined by HPLC using an Aminex HPX-87H column.

[0165] The results of these experiments are shown in Figure 5. At temperatures above 70°C, the sulfonic acid was found to decompose when exposed to longer reaction times. At 80°C, an increased yield of SAF-8 was observed, but the mixture became a dark solid, unsuitable for use in applications with specific color specifications. Sulfonation at lower temperatures (e.g., below 70°C) provides optimal sulfonation yields while avoiding excessive darkening of the solution. [Example]

[0166] Foaming power test Foaming power was evaluated according to the protocol specified in ISO 6964, with minor modifications. For each test, 700 mL of surfactant solution containing 0.2% surfactant was prepared using a hard solution of deionized water or distilled water containing 200 ppm CaCl2. The solution was prepared by stirring the ingredients at 50°C for 60 minutes. After 60 minutes, 50 mL of the solution was poured into a 1000 mL glass graduated cylinder, which was then placed in a water bath heated to 50°C. 600 mL of the surfactant solution was poured into a chromatography column equipped with a stainless steel needle at the outlet. The column was placed above the graduated cylinder so that the tip of the needle was 450 cm above the surfactant solution in the graduated cylinder. 450 mL of surfactant solution was poured from the column into the graduated cylinder. Foam height was measured 30 seconds, 3 minutes, 5 minutes, and 15 minutes after pouring. The foam height observed after 5 minutes is reported in Table 8 below.

[0167] SDS was found to have very good foaming properties in distilled water, but this was significantly reduced in hard water, leading to precipitation. The use of SAF surfactants, particularly SAF-12, improved foam stability, achieving greater foam heights than SDS in both distilled and hard water. This indicates that SAF surfactants are suitable for use in personal care products and may exhibit superior properties to SDS, even in the absence of chelating agents or foam enhancers.

[0168] [Table 8] [Example]

[0169] Toxicity testing Inhibition of B-galactosidase from Escherichia coli The Toxi-Chromo test kit supplied by EBPI was used to analyze the toxicity of various surfactants by quantifying the inhibition of E. coli in the expression of b-galactosidase in the presence of the surfactant. A mother liquor containing 1000 ppm surfactant was prepared using standard protocols. The bacterial inoculum was mixed with the reaction mixture, nutrients provided in the kit, and toxicant. 15 additional samples containing different amounts of surfactant were prepared in a well plate by subsequent dilution. After adding the chromogen provided in the kit to each well, the well plate was incubated at 37°C for 30 minutes. Optical density (OD) was read at 600 nm using a plate reader. % inhibition was measured by the change in OD (accompanied by blue color development). EC 50 was determined by plotting and fitting % inhibition versus detergent concentration.

[0170] [Table 9]

[0171] Inhibition of the growth of protist microorganisms The toxicity of various surfactants was analyzed by quantifying the inhibition of protist microorganism growth in the presence of surfactants using the Protox kit supplied by microbiotests. A dilution series of the toxicant was prepared by serial 1:1 dilutions with distilled water using standard protocols. 2 mL of each solution was placed in a UV cuvette. The protist inoculum was diluted to reach an OD of 0.04 at 440 nm, and 40 μL of the inoculum was added to each dilution vial along with 40 μL of nutrient solution. The initial OD of each vial was measured, and the vials were incubated at 30°C for 24 hours. Inhibition was measured by comparing the change in the initial OD with the final OD. EC 50 was determined as the concentration of surfactant to obtain 50% inhibition by plotting and fitting % inhibition and surfactant concentration.

[0172] [Table 10]

[0173] Toxicity testing results indicate that the length of the alkyl chain has a much greater effect on toxicity than the nature of the head group. For example, SAF-8 was found to have much lower toxicity compared to other 12-carbon chain surfactants. SAF-12 was shown to have lower toxicity than SDS, likely due to its longer overall chain length and tail group (including the ester group). Both SAF-8 and SAF-12 showed lower toxicity compared to SDBS by both methodologies, suggesting that surfactants based on furan ring head groups are less toxic than those with benzene ring head groups. [Example]

[0174] Zein solubilization test The applicability of surfactants in personal care products was tested by analyzing their ability to solubilize zein protein. In each test, 2 g of zein protein was mixed with 40 ml of a 0.5 wt % surfactant solution, and the mixture was incubated at 40° C. for 12 hours. The mixture was centrifuged, and the remaining solid zein was washed five times with 50 mL of water. The solid zein was dried in an oven at 70° C. for five days and weighed. Zein solubilization was evaluated as the percentage of zein dissolved in the surfactant solution. The test results are shown in Table 11 below.

[0175] [Table 11]

[0176] The results of this study show that SAF-8 and SAF-12 dissolve less zein than SDBS, and SAF-8 performs similarly to SDS, suggesting that the new surfactants are suitable for use in personal care products and are less irritating to the skin than commonly used surfactants such as SDBS.

[0177] The embodiments are described by way of example, and these embodiments should be considered as illustrative and not restrictive. The present disclosure is not limited to the particular embodiments described in this application. It is understood that modifications may be made without departing from the spirit and scope thereof, as would be apparent to one skilled in the art.

[0178] Subject matter encompassed by the following numbered embodiments also forms part of the present invention, optionally in combination with subject matter described above and / or defined in the following claims.

[0179] Numbered Embodiment 1 Compounds of formula (I):

[0180] [ka]

[0181] (Wherein, R1 is

[0182] [ka]

[0183] and X is a cation, R2 is acyclic C8-C 18 (It is an aliphatic group).

[0184] Numbered Embodiment 2 The compound according to numbered embodiment 1, wherein X is an alkali metal cation, such as a sodium cation or a potassium cation.

[0185] Numbered Embodiment 3 The compound of numbered embodiment 1, wherein X is a sodium cation.

[0186] Numbered Embodiment 4 R2 is linear C8~C 18 The compound of any of numbered embodiments 1 to 3, wherein the group is an aliphatic group.

[0187] Numbered Embodiment 5 R2 is linear C8~C 18 The compound of numbered embodiment 4, wherein the group is an alkyl group.

[0188] Numbered Embodiment 6 R2 is linear C8, C 12 or C 16 The compound of numbered embodiment 5, wherein the group is an alkyl group.

[0189] Numbered Embodiment 7 R2 is unsaturated linear C8-C 18 The compound of numbered embodiment 4, wherein the group is an aliphatic group.

[0190] Numbered Embodiment 8 Structure of Formula (Ia):

[0191] [ka]

[0192] The compound of any of numbered embodiments 1 to 7, having the formula:

[0193] Numbered Embodiment 9 Structure of formula (Ib):

[0194] [ka]

[0195] The compound of any one of numbered embodiments 1 to 7, having the formula:

[0196] Numbered Embodiment 10

[0197] [ka]

[0198] The compound of any of numbered embodiments 1 to 8, having the structure:

[0199] Numbered Embodiment 11 Use of a compound according to any of numbered embodiments 1 to 10 as a surfactant.

[0200] Numbered Embodiment 12 A cleaning composition comprising a compound according to any of numbered embodiments 1 to 10.

[0201] Numbered Embodiment 13 13. The cleaning composition of numbered embodiment 12, comprising a mixture of two or more compounds according to any one of claims 1 to 10.

[0202] Numbered Embodiment 14 The compound according to any one of claims 1 to 10, wherein R2 is an acyclic C8 aliphatic, and 12 or C 16 14. The cleaning composition of numbered embodiment 13, comprising a compound of any one of claims 1 to 10, which is aliphatic.

[0203] Numbered Embodiment 15 Compounds of formula (Ia):

[0204] [ka]

[0205] 1. A method for producing Compounds of formula (II):

[0206] [ka]

[0207] with a sulfonating agent; and b) adding a base to form a compound of formula (Ia) wherein X and R2 are as defined in any of numbered embodiments 1-8.

[0208] Numbered Embodiment 16 16. The method of numbered embodiment 15, wherein the sulfonating agent is selected from pyridine / sulfur trioxide complex, oleum, sulfur trioxide, or chlorosulfonic acid.

[0209] Numbered Embodiment 17 The method of numbered embodiment 15, wherein the base is an alkali metal hydroxide, such as sodium hydroxide or potassium hydroxide.

[0210] Numbered Embodiment 18 Compounds of formula (Ib):

[0211] [ka]

[0212] 1. A method for producing Compounds of formula (II):

[0213] [ka]

[0214] with a carboxylating agent, and b) adding an acid to form a compound of formula (Ib) wherein X and R2 are as defined in any of numbered embodiments 1 to 7 and 9.

[0215] Numbered Embodiment 19 The method of numbered embodiment 18, wherein the carboxylating agent is carbon dioxide.

[0216] Numbered Embodiment 20 20. The method of numbered embodiment 19, wherein step a) comprises providing a mixture of (i) a compound of Formula (II), (ii) carbon dioxide, and (iii) an alkali metal carbonate or alkaline earth metal carbonate, or a combination thereof.

[0217] Numbered Embodiment 21 20. The method of numbered embodiment 19, wherein step a) comprises providing a mixture of (i) a compound of formula (II), (ii) carbon dioxide, and (iii) potassium carbonate or cesium carbonate, or a combination thereof.

[0218] Numbered Embodiment 22 22. The method according to any of numbered embodiments 18 to 21, wherein step a) is carried out at a temperature in the range of 200 to 300° C. and a pressure of 8 to 40 bar.

[0219] Numbered Embodiment 23 Furoic acid can be reacted with a compound of formula (III):

[0220] [ka]

[0221] wherein R2 is as defined in any of numbered embodiments 1 and 4 to 7, in the presence of an acid to prepare a compound of formula (II).

[0222] Numbered Embodiment 24 Furfural can be converted into a compound of formula (III):

[0223] [ka]

[0224] wherein R2 is as defined in any of numbered embodiments 1 and 4 to 7, in the presence of an oxygen source and a catalyst to prepare a compound of formula (II).

[0225] Numbered Embodiment 25 25. The method of numbered embodiment 24, wherein the oxygen source is selected from di-tert-butyl peroxide or hydrogen peroxide.

[0226] Numbered Embodiment 26 The method of numbered embodiment 24 or numbered embodiment 25, wherein the catalyst comprises a noble metal or a transition metal.

[0227] Numbered Embodiment 27 27. The method of numbered embodiment 26, wherein the noble or transition metal is selected from the group consisting of gold, palladium, platinum, ruthenium, manganese, cobalt, or vanadium.

Claims

1. Compounds of formula (Ia): 【Chemistry 1】 (wherein X is a cation and R ２ is acyclic C ８ ~C １８ (an aliphatic group).

2. 2. The compound of claim 1, wherein X is an alkali metal cation, an alkaline earth metal cation, or an ammonium cation.

3. The compound of claim 2, wherein X is a sodium cation, a potassium cation, a lithium cation, a calcium cation, a magnesium cation, or an ammonium cation.

4. 2. The compound of claim 1, wherein X is a sodium or potassium cation.

5. 2. The compound of claim 1, wherein X is a sodium cation.

6. R ２ Branched C ８ ~C １８ The compound according to any one of claims 1 to 5, which is an alkyl group.

7. R ２ is a linear C ８ ~C １８ The compound according to any one of claims 1 to 5, which is an aliphatic group.

8. R ２ is a linear C ８ ~C １８ The compound of claim 7, which is an alkyl group.

9. R ２ is a linear C ８ , C １２ or C １６ The compound of claim 8 which is an alkyl group.

10. R ２ is unsaturated linear C ８ ~C １８ The compound of claim 7, which is an aliphatic group. 【Request Item 11】 【Chemistry 2】 The compound according to any one of claims 1 to 5 and 7 to 9, having the structure:

12. A surfactant which is a compound according to any one of claims 1 to 11.

13. 12. A composition comprising a compound of any one of claims 1 to 11, wherein the composition is a cleaning composition, a personal care composition, an oil recovery composition, a pharmaceutical composition, a drug delivery composition, an agricultural composition, a coating composition, or a paint composition.

14. A composition comprising a mixture of two or more compounds according to any one of claims 1 to 11.

15. 15. The composition of claim 14, which is a cleaning composition, a personal care composition, an oil recovery composition, a pharmaceutical composition, a drug delivery composition, an agricultural composition, a coating composition, or a paint composition.

16. R ２ is acyclic C ８ The compound according to any one of claims 1 to 11, wherein R is an aliphatic group. ２ is acyclic C １２ or C １６ 16. The composition of claim 15, comprising a compound of any one of claims 1 to 11, which is an aliphatic group.

17. Compounds of formula (Ia): 【Transformation 3】 1. A method for producing a) a compound of formula (II): 【Chemistry 4】 with a sulfonating agent; and b) adding a base to form the compound of formula (Ia) and X and R ２ is as defined in any one of claims 1 to 10.

18. 18. The method of claim 17, wherein the sulfonating agent is selected from pyridine / sulfur trioxide complex, oleum, sulfur trioxide, or chlorosulfonic acid.

19. 18. The method of claim 17, wherein the base is an alkali metal hydroxide.

20. 20. The method of claim 19, wherein the alkali metal hydroxide is sodium hydroxide or potassium hydroxide.

21. A composition comprising a compound according to any one of claims 1 to 11 and sodium dodecyl sulfate.

Images