Method for producing aliphatic polyol having 3 or more hydroxy groups and 5 or more carbon atoms in total

Abstract

A method for producing a product comprising one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total carbon atom number of five or more, the use of a compound selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts as starting compounds for producing said product compounds, and the use of a heterogeneous hydrogenation catalyst in the method for producing a product comprising one or more of said product compounds are described.

Description

[Technical field]

[0001] The present application relates to a method for producing a product comprising one or more reaction products of (a) one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more, and / or (b) one or more reaction products of one or more of said compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more, the use of compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides and their salts as starting compounds for producing such products (a) and (b), and the product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more. The use of a heterogeneous hydrogenation catalyst in the method for producing a product comprising one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more is also described. [Background technology]

[0002] Radial polyols with a core structure comparable to that of 1,1,1-trimethylolpropane (TMP) or pentaerythritol (PETP) are important synthesis targets due to their wide range of applications on an industrial scale. Currently, polyols (e.g. TMP, di-TMP, PETP, propanediol, pentanediol, etc.) are mainly produced petrochemically. Due to the finite and unstable supply of fossil raw materials and environmental reasons, it is becoming increasingly important to replace fossil raw materials by non-fossil raw materials, i.e. raw materials obtained from renewable resources.

[0003] Radial tricarboxylic acids, such as citric acid, isocitric acid, tricarballylic acid and aconitic acid, their esters, their anhydrides, and their salts, can be used as precursors for radial polyols having three hydroxyl groups, as long as selective hydrogenation of the carboxyl groups to hydroxyl groups is achieved. Tricarboxylic acids such as citric acid and aconitic acid can be obtained from renewable resources, for example from plant materials by sugar fermentation.

[0004] Unfortunately, tricarboxylic acids are difficult substrates for typical reduction procedures due to the following main reasons: · pKA values ​​incompatible with many catalytic materials; The central C=O bond has low electrophilicity, - A strong tendency to decarboxylate with increasing temperature; - Poor solubility in most organic solvents; High reduction potential (which leads to neutralization with e.g. sodium hydride, but reduction only with stronger reducing agents such as lithium aluminum hydride).

[0005] Citric acid in particular is very susceptible to decarboxylation and dehydration as temperature increases.

[0006] German Patent Application Publication No. 42 33 431 A1 discloses the preparation of propane-1,2,3-tricarboxylic acid, tetrahydrofurfuryl acetic acid and its C1-C 20 -Alkyl or C7-C 12 The present invention discloses a method for the preparation of 1,2,3-trimethyl-1,2,3-tetrahydrofuran, 3-(2'-hydroxyethyl)tetrahydrofuran, 4-hydroxymethyltetrahydropyran, 2-methyl-γ-butyrolactone and / or 3-methyl-γ-butyrolactone, comprising the steps of: 20 -Alkyl or C7-C 12-aralkyl esters are reacted over a hydrogenation catalyst in a non-aqueous solvent at 50°C to 400°C and 1 bar to 400 bar. For hydrogenation to propane-1,2,3-trimethanol, low reaction temperatures, high reaction pressures and short residence times are preferred. Propane-1,2,3-trimethanol is preferentially formed at 100°C to 250°C, in particular at 125°C to 175°C and 100 bar to 400 bar, in particular at 150 bar to 300 bar. In Example 7, 400 ml of triethyl citrate was hydrogenated at 150°C and 200 bar in 1100 ml of tetrahydrofuran using 60 g of a catalyst containing 37% by weight CuO, 1% by weight BaO, 1% by weight Cr2O3, 0.4% by weight ZnO, 15% by weight MgO, 29% by weight SiO2 ("Catalyst D") until hydrogen uptake ceases. Tetrahydrofuran was removed from the reaction product and distilled under reduced pressure to give 87 g (39%) of propane-1,2,3-trimethanol and 41.6 g (19%) of 3-(2'-hydroxyethyl)tetrahydrofuran.

[0007] US 2018 / 0346619 A1 refers to a method in which aconitic acid is reduced by lithium aluminum hydride (LiAlH4) in diethyl ether to give 3-(hydroxymethyl)-2-pentene-1,5-diol, which in a further process is reduced in ethanol solution with hydrogen gas and palladium on carbon (Pd / C) catalyst to give propane-1,2,3-trimethanol.

[0008] U.S. Patent Application No. 5,731,479 (US 5,731,479) and U.S. Patent Application Publication No. 2018 / 0346688 (US2018 / 0346688 A1) are also related art. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] DE 4233431 A1 [Patent Document 2] US Patent Application Publication No. 2018 / 0346619 [Patent Document 3] U.S. Patent Application No. 5,731,479 [Patent Document 4] US Patent Application Publication No. 2018 / 0346688 Summary of the Invention [Problem to be solved by the invention]

[0010] A first objective of the present invention is to provide a method for producing a product comprising (a) one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total carbon atom number of 5 or more, and / or (b) one or more reaction products of one or more of said compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total carbon atom number of 5 or more, which method can use starting materials obtained from renewable resources.

[0011] It is a further object to provide a process for selective hydrogenation of the carboxyl, carboalkoxy, anhydride and / or carboxylate groups of aliphatic tricarboxylic acids, their esters, their anhydrides and their salts, which provides useful yields of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms of five or more, and which suppresses undesirable side reactions that can result in, inter alia, the loss of two or more carbon atoms due to decarboxylation, incomplete hydrogenation and ring closure. [Means for solving the problem]

[0012] The first and other objects of the present invention are: (a) one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total carbon atom number of five or more; and / or (b) one or more reaction products of one or more compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total carbon atom number of five or more. A method for the preparation of a product comprising at least the following steps: (i) providing or preparing a starting material comprising one or more starting compounds selected from the group consisting of aliphatic tricarboxylic acids, esters thereof, anhydrides thereof, and salts thereof; (ii) providing or preparing a solvent having a dielectric constant greater than the dielectric constant of n-butanol; and (iii) the one or more starting compounds provided or prepared in step (i), At temperatures ranging from 80℃ to 155℃, Hydrogen partial pressure in the range of 15MPa to 30MPa, in the solvent provided or prepared in step (ii), and Chemically converted in the presence of a heterogeneous hydrogenation catalyst comprising one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os, selectively hydrogenating carboxyl, carboalkoxy, anhydride and / or carboxylate groups present in said one or more starting compounds to the corresponding hydroxy groups to produce a product comprising one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total carbon atom number of five or more; This can be achieved by the method comprising:

[0013] Surprisingly, it has been found that when the parameters of the hydrogenation reaction in step (iii) are selected as defined above, and a heterogeneous hydrogenation catalyst as defined above and a solvent as defined above are used, selective hydrogenation of the carboxyl, carboalkoxy, anhydride or carboxylate groups of aliphatic tricarboxylic acids, their esters, their anhydrides and their salts can be achieved to obtain useful yields of product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxyl groups and a total number of carbon atoms of 5 or more. Thus, when the chemical conversion of the starting compound in step (iii) is carried out using the parameters defined above, the heterogeneous hydrogenation catalyst as defined above and the solvent as defined above, undesired side reactions are suppressed (see FIG. 1 which shows, for the starting compound citric acid, the formation of aliphatic polyols having 3 or more hydroxyl groups and a total number of carbon atoms of 5 or more, and the products of possible side reactions).

[0014] In case (a) as defined above, the product resulting from step (iii) is the end product of the process, comprising one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total carbon atom number of 5 or more, wherein the end product comprises or consists of one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total carbon atom number of 5 or more.

[0015] In the case of (b) as defined above, the product resulting from step (iii) comprising one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxyl groups and a total number of carbon atoms of 5 or more is an intermediate product, and said intermediate product is transformed into a final product comprising one or more reaction products of said one or more compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxyl groups and a total number of carbon atoms of 5 or more by carrying out one or more further steps subsequent to step (iii) as defined above, where the intermediate product comprises or consists of one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxyl groups and a total number of carbon atoms of 5 or more, and the final product comprises or consists of one or more reaction products of said one or more compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxyl groups and a total number of carbon atoms of 5 or more (see below for details).

[0016] In step (i) of the method defined above, Aliphatic tricarboxylic acids, Esters of aliphatic tricarboxylic acids, Anhydrides of aliphatic tricarboxylic acids, Salts of aliphatic tricarboxylic acids A starting material is prepared or provided that includes one or more starting compounds selected from the group consisting of: Among those starting compounds, aliphatic tricarboxylic acids are preferred.

[0017] When the starting compound is an aliphatic tricarboxylic acid, the carboxyl groups are selectively hydrogenated to hydroxyl groups. When the starting compound is a salt of an aliphatic tricarboxylic acid, the carboxylate groups are selectively hydrogenated to hydroxyl groups. When the starting compound is an ester of an aliphatic tricarboxylic acid, the carboalkoxy groups are selectively hydrogenated to hydroxyl groups. When the starting compound is an anhydride of an aliphatic tricarboxylic acid, the anhydride groups and possibly remaining carboxyl groups are selectively hydrogenated to hydroxyl groups.

[0018] For example, the starting material comprises or consists of one or more starting compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts.

[0019] The starting compound, or at least one of said starting compounds, aliphatic tricarboxylic acids having a total of 6 carbon atoms, Esters of aliphatic tricarboxylic acids having a total of 6 carbon atoms, anhydrides of aliphatic tricarboxylic acids having a total of 6 carbon atoms, and Salts of aliphatic tricarboxylic acids having a total of 6 carbon atoms may be selected from the group consisting of:

[0020] Among those starting compounds, aliphatic tricarboxylic acids having a total of 6 carbon atoms are preferred.

[0021] For example, the starting material comprises or consists of one or more starting compounds selected from the group consisting of aliphatic tricarboxylic acids having a total number of carbon atoms of 6, their esters, their anhydrides, and their salts. Preferably, all of the starting compounds are selected from the group consisting of aliphatic tricarboxylic acids having a total number of carbon atoms of 6, their esters, their anhydrides, and their salts.

[0022] In certain cases, the starting compound, or at least one of said starting compounds, Tricarballylic acid, Esters of tricarballylic acid, Tricarballylic anhydride, and Salts of tricarballylic acid is selected from the group consisting of:

[0023] Of those starting compounds, tricarballylic acid is preferred.

[0024] For example, the starting material comprises or consists of one or more starting compounds selected from the group consisting of tricarballylic acid, esters thereof, anhydrides thereof, and salts thereof. Preferably, all of said starting compounds are selected from the group consisting of tricarballylic acid, esters thereof, anhydrides thereof, and salts thereof.

[0025] In certain cases, the starting compound, or at least one of said starting compounds, α,β-unsaturated aliphatic tricarboxylic acids, Esters of α,β-unsaturated aliphatic tricarboxylic acids, Anhydrides of α,β-unsaturated aliphatic tricarboxylic acids, and Salts of α,β-unsaturated aliphatic tricarboxylic acids is selected from the group consisting of:

[0026] Among these starting compounds, α,β-unsaturated aliphatic tricarboxylic acids are preferred.

[0027] For example, the starting material comprises or consists of one or more starting compounds selected from the group consisting of α,β-unsaturated aliphatic tricarboxylic acids, their esters, their anhydrides and their salts. Preferably, all of said starting compounds are selected from the group consisting of α,β-unsaturated aliphatic tricarboxylic acids, their esters, their anhydrides and their salts.

[0028] Preferably, the α,β-unsaturated aliphatic tricarboxylic acid is aconitic acid. In this case, the starting compound, or at least one of the starting compounds, is Aconitic acid, Esters of aconitic acid, Aconitic anhydride, and Aconitic acid salts is selected from the group consisting of:

[0029] Among these starting compounds, aconitic acid is preferred.

[0030] For example, the starting material comprises or consists of one or more starting compounds selected from the group consisting of aconitic acid, esters thereof, anhydrides thereof, and salts thereof. Preferably, all of said starting compounds are selected from the group consisting of aconitic acid, esters thereof, anhydrides thereof, and salts thereof.

[0031] In certain cases, the starting compound, or at least one of said starting compounds, α-functionalized aliphatic tricarboxylic acids, Esters of α-functionalized aliphatic tricarboxylic acids, Anhydrides of α-functionalized aliphatic tricarboxylic acids, and Salts of α-functionalized aliphatic tricarboxylic acids is selected from the group consisting of:

[0032] Among those starting compounds, α-functionalized aliphatic tricarboxylic acids are preferred.

[0033] For example, the starting material comprises or consists of one or more starting compounds selected from the group consisting of α-functionalized aliphatic tricarboxylic acids, their esters, their anhydrides and their salts. Preferably, all of said starting compounds are selected from the group consisting of α-functionalized aliphatic tricarboxylic acids, their esters, their anhydrides and their salts.

[0034] Preferably, the α-functionalized aliphatic tricarboxylic acid is an α-hydroxyaliphatic carboxylic acid. In this case, the starting compound, or at least one of said starting compounds, is α-Hydroxy aliphatic tricarboxylic acids, Esters of α-hydroxyaliphatic tricarboxylic acids, Anhydrides of alpha-hydroxyaliphatic tricarboxylic acids, and Salts of α-hydroxy aliphatic tricarboxylic acids is selected from the group consisting of:

[0035] Among those starting compounds, alpha-hydroxyaliphatic tricarboxylic acids are preferred.

[0036] For example, the starting material comprises or consists of one or more starting compounds selected from the group consisting of α-hydroxyaliphatic tricarboxylic acids, their esters, their anhydrides and their salts. Preferably, all of said starting compounds are selected from the group consisting of α-hydroxyaliphatic tricarboxylic acids, their esters, their anhydrides and their salts.

[0037] Preferred α-hydroxyaliphatic tricarboxylic acids are citric acid and isocitric acid. In this case, the starting compound, or at least one of the starting compounds, is Citric acid and isocitric acid, Citric acid esters and isocitric acid esters, Citric acid anhydride and isocitric acid anhydride, Citric acid salts and isocitric acid salts is selected from the group consisting of:

[0038] Among those starting compounds, citric acid and isocitric acid are preferred.

[0039] For example, the starting material comprises or consists of one or more starting compounds selected from the group consisting of citric acid, isocitric acid, esters thereof, anhydrides thereof and salts thereof. Preferably, all of said starting compounds are selected from the group consisting of citric acid, isocitric acid, esters thereof, anhydrides thereof and salts thereof.

[0040] The most preferred starting compounds in the group consisting of α-hydroxyaliphatic tricarboxylic acids, their esters, their anhydrides and their salts are citric acid, triethyl citrate and isocitric acid.For example, the starting material comprises or consists of one, two or all of citric acid, triethyl citrate and isocitric acid.Preferably, all of the starting compounds are selected from the group consisting of citric acid, triethyl citrate and isocitric acid.

[0041] Specific preferred starting compounds as mentioned above are aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts having a structure according to formula (I): [ka] [In the formula, (i) R 1 =H, R 2 =H (tricarvallic acid), or (ii) R 1 =OH, R 2 =H (isocitric acid), or (iii) R 1 =H, R 2 =OH (citric acid), or (iv) R 1 , R 2 Both show double bonds (aconitic acid)].

[0042] Thus, the starting compound, or at least one of said starting compounds, Citric acid, Isocitric acid, Aconitic acid, Tricarballylic acid, esters of acids selected from the group consisting of citric acid, isocitric acid, aconitic acid and tricarballylic acid, anhydrides of an acid selected from the group consisting of citric acid, isocitric acid, aconitic acid and tricarballylic acid, and Salts of an acid selected from the group consisting of citric acid, isocitric acid, aconitic acid and tricarballylic acid may be selected from the group consisting of:

[0043] Among those starting compounds, citric acid, isocitric acid, aconitic acid and tricarballylic acid are preferred.

[0044] For example, the starting material comprises or consists of one or more starting compounds selected from the group consisting of citric acid, isocitric acid, aconitic acid, tricarballylic acid, esters thereof, anhydrides thereof, and salts thereof. Preferably, all of said starting compounds are selected from the group consisting of citric acid, isocitric acid, aconitic acid, tricarballylic acid, esters thereof, anhydrides thereof, and salts thereof.

[0045] A particularly preferred starting compound is citric acid. For example, the starting material comprises or consists of citric acid. Preferably, the starting material consists of citric acid.

[0046] The total concentration of starting compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts may be 5% by weight or more, preferably 20% by weight or more, based on the total amount of the reaction mixture at the start of step (iii). The total concentration of all starting compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts may be 60% by weight or less, preferably 55% by weight or less, based on the total amount of the reaction mixture at the start of step (iii).

[0047] wherein the total amount of reaction mixture at the start of step (iii) is the combined amount of starting compounds and the solvent having a dielectric constant greater than that of n-butanol.

[0048] Preferably, the total concentration of starting compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides and their salts is ≧5% and ≦60% by weight, relative to the total amount of the reaction mixture at the start of step (iii). More preferably, the total concentration of starting compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides and their salts is ≧20% and ≦55% by weight, relative to the total amount of the reaction mixture at the start of step (iii).

[0049] The starting material, which comprises one or more starting compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts, preferably selected from the group consisting of citric acid and aconitic acid, is preferably prepared or isolated from plant material. Thus, the above defined method has the advantage that it can use starting materials obtained from renewable resources.

[0050] For example, the starting material is prepared from plant material by sugar fermentation.

[0051] Another potential renewable source of starting material, particularly citric acid, and starting compounds obtained from the chemical conversion of citric acid, are citrus fruits.

[0052] The product resulting from step (iii) of the process defined above comprises one or more result compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms greater than or equal to 5. For example, the product resulting from step (iii) may comprise or consist of one or more result compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms in the range of 5-6.

[0053] An aliphatic polyol having three hydroxy groups and a total of six carbon atoms is called a C6-triol. An aliphatic polyol having four hydroxy groups and a total of six carbon atoms is called a C6-tetrol. An aliphatic polyol having three hydroxy groups and a total of five carbon atoms is called a C5-triol.

[0054] Preferably, the product compound is Aliphatic polyols with 3 or 4 hydroxy groups and a total of 6 carbon atoms Aliphatic polyols with 3 hydroxy groups and a total of 5 carbon atoms The compound is selected from the group consisting of:

[0055] For example, the product resulting from step (iii) comprises or consists of one or more product compounds selected from the group consisting of aliphatic polyols having 3 or 4 hydroxy groups and a total number of carbon atoms of 6, and aliphatic polyols having 3 hydroxy groups and a total number of carbon atoms of 5. Preferably, all product compounds are compounds selected from the group consisting of aliphatic polyols having 3 or 4 hydroxy groups and a total number of carbon atoms of 6, and aliphatic polyols having 3 hydroxy groups and a total number of carbon atoms of 5.

[0056] Preferred product compounds selected from the group consisting of aliphatic polyols having 3 or 4 hydroxy groups and a total number of carbon atoms of 6 are 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol. A preferred compound selected from the group consisting of aliphatic polyols having 3 hydroxy groups and a total number of carbon atoms of 5 is 1,3,5-pentanetriol.

[0057] In certain preferred cases, the product resulting in step (iii) comprises two or more product compounds selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol, 3-(hydroxymethyl)-2-pentene-1,5-diol and 1,3,5-pentanetriol.

[0058] From starting compounds selected from the group consisting of citric acid (shown by way of example below), its esters, its salts and its anhydrides, the process according to the invention makes it possible to obtain the product compounds 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol, 3-(hydroxymethyl)-2-pentene-1,5-diol and 1,3,5-pentanetriol: [ka]

[0059] From starting compounds selected from the group consisting of aconitic acids (exemplary below), their esters, their salts and their anhydrides, the process according to the invention makes it possible to obtain the product compounds propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol: [ka]

[0060] From a starting compound selected from the group consisting of tricarballylic acids, their esters, their salts and their anhydrides, the process according to the invention makes it possible to obtain the product compound propane-1,2,3-trimethanol.

[0061] From starting compounds selected from the group consisting of isocitric acid (exemplary below), its esters, its salts and its anhydrides, the following product compounds can be obtained by the process according to the invention: [ka]

[0062] In the product resulting from step (iii), the total amount of aliphatic polyols having 3 or more hydroxyl groups and a total carbon number in the range of 5 to 6 may be 30% by mass or more, preferably 50% by mass or more, or in the range of 40% by mass to 95% by mass, based on the total amount of the remaining starting compounds and the product compounds obtained by chemical conversion of one or more starting compounds (including the product compounds that are not aliphatic polyols having 3 or more hydroxyl groups and a total carbon number in the range of 5 to 6). It is understood that a certain amount of the product compounds that are not aliphatic polyols having 3 or more hydroxyl groups and a total carbon number in the range of 5 to 6 may result from unavoidable side reactions.

[0063] Preferably, in the product resulting from step (iii), the total amount of product compounds selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol, 3-(hydroxymethyl)-2-pentene-1,5-diol, and 1,3,5-pentanetriol is greater than 30% by weight, preferably greater than 50% by weight, or may range from 40% to 95% by weight, based on the total amount of the remaining starting compounds and the product compounds obtained by chemical conversion of one or more starting compounds (including product compounds that are not aliphatic polyols having three or more hydroxy groups and a total carbon number in the range of 5 to 6). It is understood that a certain amount of product compounds that are not aliphatic polyols having three or more hydroxy groups and a total carbon number in the range of 5 to 6 may result from unavoidable side reactions.

[0064] When an aliphatic tricarboxylic acid or its salt or its anhydride is used as the starting compound, it is preferably chemically transformed in step (iii) so that the number of carbon atoms present in the starting compound is mainly maintained and the resulting aliphatic polyol has the same number of carbon atoms as the starting compound, or the number of carbon atoms present in the starting compound is reduced by one and the resulting aliphatic polyol has one less carbon atom than the starting compound. Thus, not more than one carbon atom of the starting compound is mainly lost by decarboxylation. In certain cases, the starting compound is chemically transformed in step (iii) so that the number of carbon atoms present in the starting compound is mainly maintained and the resulting aliphatic polyol has the same number of carbon atoms as the starting compound. In this case, the carbon atoms of the starting compound are not mainly lost by decarboxylation. Here, mainly means that more than 50% by weight of the product (a) defined above meets the condition defined above. Preferably, more than 60% by weight, more preferably more than 70% by weight of the product (a) meets the condition defined above. Here, the total mass of product (a) is the sum of the masses of the aliphatic polyol having three or more hydroxy groups and a total carbon atom number of five or more, the remaining starting compounds, and the product compounds formed by side reactions that are not aliphatic polyols having three or more hydroxy groups and a total carbon atom number in the range of 5 to 6.

[0065] When an aliphatic tricarboxylic acid or its salt or its anhydride is used as the starting compound, it is preferably chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in the starting compound is mainly maintained and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as the starting compound, or one carbon-carbon single bond present in the starting compound is converted into a carbon-carbon double bond and the resulting aliphatic polyol has one less carbon-carbon single bond than the starting compound. Thus, not more than one carbon-carbon single bond of the starting compound is mainly transformed into a carbon-carbon double bond by dehydration. In a particular case, the starting compound is chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in the starting compound is mainly maintained and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as the starting compound. In this case, the carbon-carbon single bonds of the starting compound are not mainly transformed into carbon-carbon double bonds by dehydration. Here, mainly means that more than 50% by weight of the product (a) defined above meets the condition defined above. Preferably, more than 60% by weight, more preferably more than 70% by weight, of product (a) meets the above defined conditions, where the total weight of product (a) is the sum of the weights of the aliphatic polyol having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more, the remaining starting compounds and the product compounds formed by side reactions that are not aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms in the range of 5-6.

[0066] When an α,β-unsaturated aliphatic tricarboxylic acid or a salt thereof or an anhydride thereof is used as a starting compound, it is preferably chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in the starting compound is mainly maintained and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as the starting compound, or the carbon-carbon double bonds present in the starting compound are converted by hydrogenation into carbon-carbon single bonds and the resulting aliphatic polyol has one more carbon-carbon single bond than the starting compound. Here, mainly means that more than 50% by weight of the product (a) defined above meets the conditions defined above. Preferably, more than 60% by weight, more preferably more than 70% by weight of the product (a) meets the conditions defined above. Here, the total mass of the product (a) is the sum of the masses of the aliphatic polyol having 3 or more hydroxyl groups and a total carbon atom number of 5 or more, the remaining starting compound, and the product compound formed by side reactions that is not an aliphatic polyol having 3 or more hydroxyl groups and a total carbon atom number in the range of 5 to 6.

[0067] When an ester of an aliphatic tricarboxylic acid is used as a starting compound, it is preferably chemically transformed in step (iii) so that the number of carbon atoms present in the aliphatic tricarboxylic acid corresponding to the ester is mainly maintained, and the resulting aliphatic polyol has the same number of carbon atoms as the aliphatic tricarboxylic acid corresponding to the ester, or the number of carbon atoms present in the aliphatic tricarboxylic acid corresponding to the ester is reduced by one, and the resulting aliphatic polyol has one less carbon atom than the aliphatic tricarboxylic acid corresponding to the ester. Thus, not more than one carbon atom of the aliphatic tricarboxylic acid corresponding to the ester used as a starting compound is mainly lost by decarboxylation. In certain cases, the ester is chemically transformed in step (iii) so that the number of carbon atoms present in the aliphatic tricarboxylic acid corresponding to the ester is mainly maintained, and the resulting aliphatic polyol has the same number of carbon atoms as the aliphatic tricarboxylic acid corresponding to the ester. In this case, the carbon atoms of the aliphatic tricarboxylic acid corresponding to the ester used as a starting compound are not mainly lost by decarboxylation. Here, mainly means that more than 50% by mass of the product (a) defined above satisfies the conditions defined above. Preferably, more than 60% by mass, more preferably more than 70% by mass of the product (a) satisfies the conditions defined above. Here, the total mass of the product (a) is the sum of the masses of the aliphatic polyol having 3 or more hydroxyl groups and a total carbon atom number of 5 or more, the remaining starting compounds, and the product compounds formed by side reactions that are not aliphatic polyols having 3 or more hydroxyl groups and a total carbon atom number in the range of 5 to 6.

[0068] When an ester of an aliphatic tricarboxylic acid is used as a starting compound, it is preferably chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in the aliphatic tricarboxylic acid corresponding to the ester is mainly maintained, and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as the aliphatic tricarboxylic acid corresponding to the ester, or one carbon-carbon single bond present in the aliphatic tricarboxylic acid corresponding to the ester is converted into a carbon-carbon double bond, and the resulting aliphatic polyol has one less carbon-carbon single bond than the aliphatic tricarboxylic acid corresponding to the ester. Thus, one or less carbon-carbon single bonds of the aliphatic tricarboxylic acid corresponding to the ester are mainly transformed into carbon-carbon double bonds by dehydration. In certain cases, the ester is chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in the aliphatic tricarboxylic acid corresponding to the ester is mainly maintained, and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as the aliphatic tricarboxylic acid corresponding to the ester. In this case, the carbon-carbon single bond of the aliphatic tricarboxylic acid corresponding to the ester is not mainly converted to a carbon-carbon double bond by dehydration. Here, mainly means that more than 50% by mass of the product (a) defined above satisfies the conditions defined above. Preferably, more than 60% by mass, more preferably more than 70% by mass of the product (a) satisfies the conditions defined above. Here, the total mass of the product (a) is the sum of the masses of the aliphatic polyol having 3 or more hydroxyl groups and a total carbon atom number of 5 or more, the remaining starting compounds, and the product compounds formed by side reactions that are not aliphatic polyols having 3 or more hydroxyl groups and a total carbon atom number in the range of 5 to 6.

[0069] When an ester of an α,β-unsaturated aliphatic tricarboxylic acid is used as a starting compound, it is preferably chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in the α,β-unsaturated aliphatic tricarboxylic acid corresponding to the ester is mainly maintained, and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as the α,β-unsaturated aliphatic tricarboxylic acid corresponding to the ester, or the carbon-carbon double bonds present in the α,β-unsaturated aliphatic tricarboxylic acid corresponding to the ester are converted into carbon-carbon single bonds, and the resulting aliphatic polyol has one more carbon-carbon single bond than the α,β-unsaturated aliphatic tricarboxylic acid corresponding to the ester. Mainly means here that more than 50% by weight of the product (a) defined above meets the conditions defined above. Preferably, more than 60% by weight, more preferably more than 70% by weight of the product (a) meets the conditions defined above. Here, the total mass of product (a) is the sum of the masses of the aliphatic polyol having three or more hydroxy groups and a total carbon atom number of five or more, the remaining starting compounds, and the product compounds formed by side reactions that are not aliphatic polyols having three or more hydroxy groups and a total carbon atom number in the range of 5 to 6.

[0070] When citric acid or its salts or their anhydrides are used as starting compounds, it is preferably chemically transformed in step (iii) so that the number of carbon atoms present in citric acid is mainly maintained and the resulting aliphatic polyol has the same number of carbon atoms as citric acid, or the number of carbon atoms present in citric acid is reduced by one, so that the resulting aliphatic polyol has one less carbon atom than citric acid. Thus, not more than one carbon atom of citric acid is mainly lost by decarboxylation. In certain cases, citric acid is chemically transformed in step (iii) so that the number of carbon atoms present in citric acid is mainly maintained and the resulting aliphatic polyol has the same number of carbon atoms as citric acid. In this case, the carbon atoms of citric acid are not mainly lost by decarboxylation. Here, mainly means that more than 50% by weight of the product (a) defined above meets the conditions defined above. Preferably, more than 60% by weight, more preferably more than 70% by weight of the product (a) meets the conditions defined above. Here, the total mass of product (a) is the sum of the masses of the aliphatic polyol having three or more hydroxy groups and a total carbon atom number of five or more, the remaining starting compounds, and the product compounds formed by side reactions that are not aliphatic polyols having three or more hydroxy groups and a total carbon atom number in the range of 5 to 6.

[0071] When citric acid or its salts or their anhydrides are used as starting compounds, it is preferably chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in citric acid is mainly maintained and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as citric acid, or one carbon-carbon single bond present in citric acid is converted to a carbon-carbon double bond by dehydration so that the resulting aliphatic polyol has one less carbon-carbon single bond than citric acid. In a particular case, said starting compound is chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in citric acid is mainly maintained and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as citric acid. In this case, dehydration of citric acid does not mainly occur. Here, mainly means that more than 50% by weight of the product (a) defined above meets the conditions defined above. Preferably, more than 60% by weight, more preferably more than 70% by weight of the product (a) meets the conditions defined above. Here, the total mass of product (a) is the sum of the masses of the aliphatic polyol having three or more hydroxy groups and a total carbon atom number of five or more, the remaining starting compounds, and the product compounds formed by side reactions that are not aliphatic polyols having three or more hydroxy groups and a total carbon atom number in the range of 5 to 6.

[0072] When an ester of citric acid is used as the starting compound, it is preferably chemically transformed in step (iii) so that the number of carbon atoms present in citric acid is mainly maintained and the resulting aliphatic polyol has the same number of carbon atoms as citric acid, or the number of carbon atoms present in citric acid is reduced by one, so that the resulting aliphatic polyol has one less carbon atom than citric acid. Thus, not more than one carbon atom of citric acid is mainly lost by decarboxylation. In certain cases, the starting compound is chemically transformed in step (iii) so that the number of carbon atoms present in citric acid is mainly maintained and the resulting aliphatic polyol has the same number of carbon atoms as citric acid. In this case, the carbon atoms of citric acid are not mainly lost by decarboxylation. Here, mainly means that more than 50% by weight of the product (a) defined above meets the conditions defined above. Preferably, more than 60% by weight, more preferably more than 70% by weight of the product (a) meets the conditions defined above. Here, the total mass of product (a) is the sum of the masses of the aliphatic polyol having three or more hydroxy groups and a total carbon atom number of five or more, the remaining starting compounds, and the product compounds formed by side reactions that are not aliphatic polyols having three or more hydroxy groups and a total carbon atom number in the range of 5 to 6.

[0073] When an ester of citric acid is used as the starting compound, it is preferably chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in citric acid is mainly maintained and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as citric acid, or one carbon-carbon single bond present in citric acid is converted to a carbon-carbon double bond by dehydration and the resulting aliphatic polyol has one less carbon-carbon single bond than citric acid. In a particular case, the starting compound is chemically transformed in step (iii) so that the number of carbon-carbon single bonds present in citric acid is mainly maintained and the resulting aliphatic polyol has the same number of carbon-carbon single bonds as citric acid. In this case, dehydration of citric acid does not mainly occur. Here, mainly means that more than 50% by weight of the product (a) defined above meets the conditions defined above. Preferably, more than 60% by weight, more preferably more than 70% by weight of the product (a) meets the conditions defined above. Here, the total mass of product (a) is the sum of the masses of the aliphatic polyol having three or more hydroxy groups and a total carbon atom number of five or more, the remaining starting compounds, and the product compounds formed by side reactions that are not aliphatic polyols having three or more hydroxy groups and a total carbon atom number in the range of 5 to 6.

[0074] In step (ii) of the method defined above, a solvent is prepared or provided having a dielectric constant greater than that of n-butanol. Said solvent is therefore more polar than n-butanol. Preferred solvents are protic. Such solvents have sufficient solubility for the starting compounds defined above.

[0075] The solvent provided or prepared in step (ii) may comprise one or more components selected from the group consisting of water, methanol, ethanol, n-propanol, iso-propanol, ethylene glycol, propylene glycol and cyclic ethers in proportions that result in a dielectric constant greater than that of n-butanol. Exemplary cyclic ethers are tetrahydrofuran (THF), tetrahydropyran (THP), and dioxane.

[0076] Preferably, the solvent is Water, and an aqueous mixture comprising more than 50% by weight, preferably more than 70% by weight, more preferably more than 90% by weight of water relative to the total amount of solvent; is selected from the group consisting of:

[0077] In the aqueous mixture, one or more of methanol, ethanol, n-propanol, iso-propanol, ethylene glycol, propylene glycol, cyclic ethers may be mixed with water.

[0078] In step (iii) of the above defined process, said one or more starting compounds provided or prepared in step (i) are chemically converted into one or more product compounds as defined above at a temperature in the range of 80°C to 155°C, preferably at a temperature in the range of 120°C to 155°C.

[0079] Depending on the reaction temperature, the chemical conversion of starting compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts in the presence of a given heterogeneous hydrogenation catalyst at hydrogen partial pressures ranging from 15 MPa to 30 MPa may result in either lactones (not according to the invention, see FIG. 1), or aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more, or a mixture of both types of products. Thus, in step (iii), the reaction temperature is preferably selected to selectively prepare said aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more instead of lactones.

[0080] Step (iii) of the method defined above may be carried out for a period of at least 30 hours, preferably at least 60 hours. Step (iii) of the method defined above may be carried out for a period of at most 200 hours, preferably at most 120 hours, more preferably at most 96 hours. Preferably, step (iii) of the method defined above is carried out for a period of at least 30 hours and at most 200 hours. More preferably, step (iii) of the method defined above is carried out for a period of at least 60 hours and at most 120 hours, preferably at most 96 hours.

[0081] In step (iii) of the above defined process, said one or more starting compounds provided or prepared in step (i) are chemically converted into one or more product compounds as defined above in the presence of a heterogeneous hydrogenation catalyst comprising one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os.

[0082] A preferred heterogeneous hydrogenation catalyst comprises or consists of one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os in a total amount of at least 90% by weight, preferably at least 95% by weight, based on the total amount of the heterogeneous hydrogenation catalyst, whereby the amount of Ru is preferably at least 90% by weight, preferably at least 95% by weight, based on the total amount of the heterogeneous hydrogenation catalyst.

[0083] Other preferred heterogeneous hydrogenation catalysts comprise or consist of one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os in a total amount of 10% by weight or more relative to the total amount of the heterogeneous hydrogenation catalyst in combination with one or more metals selected from the group consisting of Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au, where the total amount of metals selected from the group consisting of Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au is 98% by weight or more relative to the total amount of the heterogeneous hydrogenation catalyst. Catalysts comprising or consisting of one or both of Re and Ru in combination with one or both of Pd and Pt are preferred, where the total amount of metals selected from the group consisting of Re, Rh, Pd and Pt is 98% by weight or more relative to the total amount of the heterogeneous hydrogenation catalyst.

[0084] In either case, it is understood that the catalyst may contain minor amounts of other metals and oxides contained in the amounts of heterogeneous hydrogenation catalyst described above.

[0085] Preferably, the amount of the heterogeneous hydrogenation catalyst relative to the total amount of the starting compounds is in the range of 0.01% by mass to 5% by mass, preferably 0.05% by mass to 2.5% by mass.

[0086] The heterogeneous hydrogenation catalyst may be supported by a support material (also called a support). The mass of the support material is not included in the above-mentioned amounts of the heterogeneous hydrogenation catalyst.

[0087] The support material of the heterogeneous hydrogenation catalyst is preferably selected to withstand the hydrothermal stress resulting from the thermal, water, acid and hydrocracking conditions simultaneously present during step (iii) of the process defined above.

[0088] Preferably, the support material is selected from the group consisting of metal oxides, zeolites, and carbon-based materials, preferably Al2O3, ZrO2, TiO2, SiC, carbon black, and PTFE. Combinations of different support materials are possible, for example PTFE-supported carbon black.

[0089] In the supported catalyst, the total amount of the heterogeneous hydrogenation catalyst is preferably in the range of 0.1 mass % to 10 mass %, preferably 0.5 mass % to 5 mass %, based on the total mass of the heterogeneous hydrogenation catalyst and the support material.

[0090] Preferred combinations of catalytic metal and support material are Ru with carbon black, PTFE-supported carbon black, Al2O3, or SiC, and Re / Pt with carbon black.

[0091] After step (iii), the supported heterogeneous hydrogenation catalyst may be recovered, preferably by means of filtration.

[0092] The method defined above may comprise one or more further steps carried out after step (iii) defined above.

[0093] In a further step carried out after step (iii) as defined above, the solvent used in step (iii) can be removed by evaporation. Evaporation of the solvent can be carried out by any suitable method. For example, evaporation of the solvent can be carried out by freeze-drying.

[0094] In a further step carried out after step (iii) defined above, one or more of said resultant compounds present in the product resulting from step (iii) selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more can be chemically transformed to give a product (b) comprising one or more reaction products of said one or more compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more, wherein the product resulting in step (iii) comprising one or more resultant compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more is an intermediate product, and said intermediate product is chemically transformed into a final product comprising one or more reaction products of said one or more compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more.

[0095] In a further step carried out after step (iii) defined above, one or more further chemicals may be added to said one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more, present in the product resulting from step (iii), to result in a reaction mixture comprising said one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more. Thus, one or more aliphatic polyols resulting from step (iii) defined above having three or more hydroxy groups and a total number of carbon atoms of five or more, One or more further chemical substances that are not aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms 5 or more A reaction mixture is formed containing:

[0096] Such reaction mixtures are configured and intended for use in preparing reaction products different from those mentioned above resulting from step (iii) defined above, comprising one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more (see below for details).

[0097] In the reaction mixture, one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and 5 or more total carbon atoms may function as reactants or as solvents.

[0098] The method as defined above may comprise one, two or all of the further steps as defined above, carried out after step (iii) as defined above.

[0099] As explained above, in case (a), the product of the process defined above comprises one or more resultant compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total carbon atom number of 5 or more.

[0100] The product (a) is Peptides, a protein, preferably selected from the group consisting of human serum albumin and bovine serum albumin, an enzyme, preferably selected from the group consisting of lysozyme, protease, amylase, lipase, mannanase, and cellulase, a microorganism, preferably selected from the group consisting of gram-positive bacteria, gram-negative bacteria, spore-forming bacteria, fungal spores, mycelium, and yeasts, - a virus selected from the group consisting of DNA, RNA and a virus, preferably a bacteriophage, The composition may be selected from the group consisting of a formulation comprising one or more materials selected from the group consisting of:

[0101] Formulations comprising one or more materials selected from the group consisting of peptides, proteins, enzymes, DNA, RNA, viruses, and microorganisms are used for a variety of different applications including biocatalysis, food sector, feed applications, home care, personal care, and agriculture.

[0102] In such formulations, the resulting compound selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more can replace conventional solvents such as 1,2-propanediol, glycerol or sorbitol, and / or can protect and stabilize materials selected from the group consisting of peptides, proteins, enzymes, DNA, RNA, viruses and microorganisms. More specifically, the resulting compound selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more can be used as a biostatic agent to avoid the growth of microorganisms.

[0103] The product (a) may be a paint formulation or an adhesive formulation, preferably a paint formulation or an adhesive formulation containing phenoxyethanol, in which the product compound selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total carbon atom number of 5 or more can enhance the germicidal action of phenoxyethanol.

[0104] Product (a) may be a reaction mixture in which one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms 5 or more replace traditional polyols such as 1,1,1-trimethylolpropane (TMP) or pentaerythritol (PETP).

[0105] For example, product (a) is a reaction mixture for converting one or more of said aliphatic polyols having 3 or more hydroxy groups and a total carbon atom number of 5 or more into polyalkoxylates by alkoxylation with ethylene oxide and / or propylene oxide, said reaction mixture being prepared after step (iii) of chemically converting said one or more starting compounds.

[0106] For example, product (a) is a reaction mixture for preparing a polymer, preferably selected from the group consisting of polyurethanes, polyesters, and polyacrylates, said reaction mixture being prepared after step (iii) of chemically converting said one or more starting compounds. In the reaction mixture for preparing polyacrylates, a product compound selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more can result in encapsulation after suspension polymerization.

[0107] For example, product (a) is a reaction mixture for preparing esters, acyclic ethers or cyclic ethers of one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more, said reaction mixture being prepared after step (iii) of chemically converting one or more starting compounds. Preferred esters are acetyl esters. Acyclic ethers are obtained by tert-butylation. Cyclic ethers are obtained by dehydration cyclization. After further functionalization, said esters, acyclic ethers and cyclic ethers can be potential building blocks for odor and fragrance chemistry.

[0108] The above-mentioned reaction mixture can be obtained in a further step carried out after step (iii) of chemically converting said one or more starting compounds by adding one or more further chemical substances to said one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more.

[0109] As explained above, in case (b), the product of the above defined process comprises one or more reaction products of one or more of said compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms of 5 or more.

[0110] The product (b) may be selected from the group consisting of products comprising one or more polyalkoxylates, at least one of which is prepared from one or more of said product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total carbon number of 5 or more in a further step carried out after step (iii) of chemically converting said one or more starting compounds. Such polyalkoxylates may be used as non-ionic foam suppressors and demulsifiers in a wide range of applications, for example in home and personal care applications. The polyalkoxylates obtained by the process according to the invention are expected to have enhanced biodegradability compared to conventional polyalkoxylates.

[0111] Product (b) may be selected from the group consisting of products comprising one or more polymers, preferably polymers selected from the group consisting of polyurethanes and polyesters, at least one of said polymers being prepared from said one or more result compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms 5 or more in a further step carried out after step (iii) of chemically converting said one or more starting compounds.

[0112] In a particularly preferred method according to the invention, (a) one, two, three or all of the product compounds selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol, 3-(hydroxymethyl)-2-pentene-1,5-diol, and 1,3,5-pentanetriol, and / or (b) one or more reaction products of one, two, three or all of said product compounds. The product comprising at least the following steps: (i) providing or preparing a starting material comprising one or more starting compounds selected from the group consisting of citric acid, esters thereof, anhydrides thereof, and salts thereof; (ii) providing or preparing a solvent having a dielectric constant greater than that of n-butanol, said solvent being water or a mixture of water and one selected from the group consisting of methanol and ethylene glycol; and (iii) the one or more starting compounds provided or prepared in step (i), At temperatures ranging from 120℃ to 155℃, Hydrogen partial pressure in the range of 15MPa to 30MPa, in the solvent provided or prepared in step (ii), and In the presence of a heterogeneous hydrogenation catalyst containing Ru, chemically converting, selectively hydrogenating carboxyl, carboalkoxy, anhydride and / or carboxylate groups present in one or more starting compounds to the corresponding hydroxy groups to yield products comprising one, two, three or all of the product compounds selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol, 3-(hydroxymethyl)-2-pentene-1,5-diol, and 1,3,5-pentanetriol; It is prepared by a method comprising:

[0113] In another particularly preferred method according to the invention, (a) one or both product compounds selected from the group consisting of propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol, and / or (b) one or more reaction products of one or both of said product compounds. The product comprising at least the following steps: (i) providing or preparing a starting material comprising one or more starting compounds selected from the group consisting of aconitic acid, esters thereof, anhydrides thereof, and salts thereof; (ii) providing or preparing a solvent having a dielectric constant greater than that of n-butanol, said solvent being water or a mixture of water and one selected from the group consisting of methanol and ethylene glycol; and (iii) the one or more starting compounds provided or prepared in step (i), At temperatures ranging from 120℃ to 155℃, Hydrogen partial pressure in the range of 15MPa to 30MPa, in the solvent provided or prepared in step (ii), and In the presence of a heterogeneous hydrogenation catalyst containing Ru, chemically converting, selectively hydrogenating carboxyl, carboalkoxy, anhydride and / or carboxylate groups present in one or more starting compounds to the corresponding hydroxy groups to yield a product comprising one or both product compounds selected from the group consisting of propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol; It is prepared by a method comprising:

[0114] In a further particularly preferred method according to the invention, (a) the product compound propane-1,2,3-trimethanol, and / or (b) one or more reaction products of said product compounds. The product comprising at least the following steps: (i) providing or preparing a starting material comprising one or more starting compounds selected from the group consisting of tricarballylic acids, esters thereof, anhydrides thereof, and salts thereof; (ii) providing or preparing a solvent having a dielectric constant greater than that of n-butanol, said solvent being water or a mixture of water and one selected from the group consisting of methanol and ethylene glycol; and (iii) the one or more starting compounds provided or prepared in step (i), At temperatures ranging from 120℃ to 155℃, Hydrogen partial pressure in the range of 15MPa to 30MPa, in the solvent provided or prepared in step (ii), and In the presence of a heterogeneous hydrogenation catalyst containing Ru, chemically converting, selectively hydrogenating, carboxyl, carboalkoxy, anhydride and / or carboxylate groups present in one or more starting compounds to the corresponding hydroxy groups to yield products comprising the result compound propane-1,2,3-trimethanol; It is prepared by a method comprising:

[0115] The present application, A formulation comprising one or more materials selected from the group consisting of: Peptides, a protein, preferably selected from the group consisting of human serum albumin and bovine serum albumin, an enzyme, preferably selected from the group consisting of lysozyme, protease, amylase, lipase, mannanase, and cellulase, a microorganism, preferably selected from the group consisting of gram-positive bacteria, gram-negative bacteria, spore-forming bacteria, fungal spores, mycelia, yeasts, a virus selected from the group consisting of DNA, RNA and a virus, preferably a bacteriophage, paint and adhesive formulations, preferably containing phenoxyethanol, a reaction mixture for converting said one or more aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms 5 or more into polyalkoxylates by alkoxylation with ethylene oxide and / or propylene oxide, said reaction mixture being prepared after step (iii); a reaction mixture for preparing a polymer, preferably a polymer selected from the group consisting of polyurethanes, polyesters and polyacrylates, said reaction mixture being prepared after step (iii), and a reaction mixture for preparing an ester, acyclic ether or cyclic ether of said one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and 5 or more total carbon atoms, said reaction mixture being prepared after step (iii). wherein the product comprises one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6.

[0116] Preferably, the product defined above is an aliphatic polyol having 3 or 4 hydroxy groups and a total of 6 carbon atoms, and Aliphatic polyols with 3 hydroxy groups and a total of 5 carbon atoms The polyol comprises an aliphatic polyol selected from the group consisting of:

[0117] The aliphatic polyol having 3 or 4 hydroxy groups and a total number of carbon atoms of 6 is preferably selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol. A preferred aliphatic polyol having 3 hydroxy groups and a total number of carbon atoms of 5 is 1,3,5-pentanetriol.

[0118] More preferably, the product as defined above comprises two or more product compounds selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol, 3-(hydroxymethyl)-2-pentene-1,5-diol and 1,3,5-pentanetriol.

[0119] The product as defined above can be obtained by a process as defined above, preferably by one of the preferred processes as defined above.

[0120] The present application, one or more product compounds selected from the group consisting of: an aliphatic polyol having 3 or 4 hydroxy groups and a total of 6 carbon atoms; Aliphatic polyols with 3 hydroxy groups and a total of 5 carbon atoms or A mixture of such products The present invention also relates to the use of one or more compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts as starting materials for the preparation of

[0121] With regard to the specific and preferred aliphatic tricarboxylic acids, their esters, their anhydrides and their salts used as starting compounds for producing the above defined product compounds, the same applies as disclosed in connection with the above defined process. Most preferred is the use of citric acid and aconitic acid as starting compounds for producing the above defined products.

[0122] Concerning the specific and preferred product compounds, the same applies as disclosed in connection with the process defined above. The aliphatic polyol having 3 or 4 hydroxy groups and a total number of carbon atoms of 6 is preferably selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol. The preferred aliphatic polyol having 3 hydroxy groups and a total number of carbon atoms of 5 is 1,3,5-pentanetriol.

[0123] A product compound selected from the group consisting of: an aliphatic polyol having 3 or 4 hydroxy groups and a total of 6 carbon atoms, and Aliphatic polyols with 3 hydroxy groups and a total of 5 carbon atoms or A mixture of such products Preferred is the use of one or more compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts as starting compounds for the production of

[0124] Most preferably, the preferred compounds as defined above selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts are used as starting compounds in the process as defined above.

[0125] The present application, one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os in a total amount of at least 90% by weight, preferably at least 95% by weight, relative to the total amount of the heterogeneous hydrogenation catalyst, preferably the amount of Ru being at least 90% by weight, preferably at least 95% by weight, relative to the total amount of the heterogeneous hydrogenation catalyst, or one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os in a total amount of at least 10% by weight, relative to the total amount of the heterogeneous hydrogenation catalyst, in combination with one or more metals selected from the group consisting of Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au, preferably Re and / or Ru in combination with Pd and / or Pt, wherein the total amount of metals selected from the group consisting of Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au is at least 98% by weight, relative to the total amount of the heterogeneous hydrogenation catalyst, The present invention also relates to the use of a heterogeneous hydrogenation catalyst in a process for producing a product comprising one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms of five or more, said process comprising chemically converting one or more compounds selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides, and their salts to produce a product comprising one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms of five or more.

[0126] With regard to the specific and preferred heterogeneous hydrogenation catalysts, the same applies as disclosed in connection with the process defined above.With regard to the specific and preferred aliphatic tricarboxylic acids, their esters, their anhydrides and their salts, which are converted in the process using the catalysts defined above, the same applies as disclosed in connection with the process defined above.The use of citric acid and aconitic acid to prepare the products defined above is most preferred.

[0127] Concerning the specific and preferred product compounds, the same applies as disclosed in connection with the process defined above. The aliphatic polyol having 3 or 4 hydroxy groups and a total number of carbon atoms of 6 is preferably selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol. The preferred aliphatic polyol having 3 hydroxy groups and a total number of carbon atoms of 5 is 1,3,5-pentanetriol.

[0128] With regard to the specific and preferred reaction parameters (temperature, hydrogen partial pressure, duration of chemical conversion, solvent), the same applies as disclosed in connection with the process defined above. Most preferably, a heterogeneous catalyst as defined above is used in the process defined above. [Brief description of the drawings]

[0129] [Figure 1] FIG. 1 illustrates the formation of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms 5 or more from citric acid, as well as possible products of side reactions of citric acid. EXAMPLES

[0130] The following examples according to the invention are intended to further explain and illustrate the present invention without limiting its scope.

[0131] FIG. 1 illustrates the formation of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms 5 or more from citric acid, as well as possible side reaction products of citric acid.

[0132] Hydrogenation of citric acid dissolved in water was carried out as follows: The heterogeneous hydrogenation catalyst (type of catalyst, type of support material and amount shown in Table 1) was added to a solution of the starting compound citric acid monohydrate in water as solvent (concentration of citric acid and amount of solution shown in Table 1) in an autoclave (optionally using a catalyst basket). The reaction vessel was closed and then flushed twice with nitrogen gas (0.5 MPa). Stirring (700 U / min) and initial hydrogen pressure (5 MPa) were then applied. The reaction mixture was heated to the temperature shown in Table 1 and the hydrogen pressure was increased to the value shown in Table 1. Under these conditions, the reaction mixture was stirred for the time shown in Table 1, then cooled to room temperature and flushed twice with nitrogen gas (0.5 MPa). The catalyst was then filtered off if no catalyst basket was used. The solvent (water) was removed by evaporation. The resulting oil was analyzed by gas chromatography and HPLC. The experimental parameters and results of the example with citric acid are summarized in Table 1.

[0133] Hydrogenation of aconitic acid dissolved in water was carried out as follows: The heterogeneous hydrogenation catalyst (type of catalyst, type of support material and amount shown in Table 2) was added to a solution of the starting compound aconitic acid in water as solvent (concentration of aconitic acid and amount of solution shown in Table 2) in an autoclave (optionally using a catalyst basket). The reaction vessel was closed and then flushed twice with nitrogen gas (0.5 MPa). Agitation (700 U / min) and initial hydrogen pressure (5 MPa) were then applied. The reaction mixture was heated to the temperature shown in Table 2 and the hydrogen pressure was increased to the value shown in Table 2. Under these conditions, the reaction mixture was stirred for the time shown in Table 2, then cooled to room temperature and flushed twice with nitrogen gas (0.5 MPa). The catalyst was then filtered off if no catalyst basket was used. The solvent (water) was removed by evaporation. The resulting oil was analyzed by gas chromatography and HPLC. The experimental parameters and results of the example with aconitic acid are summarized in Table 2.

[0134] Hydrogenation of tricarballylic acid dissolved in water was carried out as follows: The heterogeneous hydrogenation catalyst (type of catalyst, type of support material and amount shown in Table 3) was added to a solution of the starting compound tricarballylic acid in water as solvent (concentration of tricarballylic acid and amount of solution shown in Table 3) in an autoclave (optionally using a catalyst basket). The reaction vessel was closed and then flushed twice with nitrogen gas (0.5 MPa). Stirring (700 U / min) and initial hydrogen pressure (5 MPa) were then applied. The reaction mixture was heated to the temperature shown in Table 3 and the hydrogen pressure was increased to the value shown in Table 3. Under these conditions, the reaction mixture was stirred for the time shown in Table 3, then cooled to room temperature and flushed twice with nitrogen gas (0.5 MPa). The catalyst was then filtered off if no catalyst basket was used. The solvent (water) was removed by evaporation. The resulting oil was analyzed by gas chromatography and HPLC. The experimental parameters and results of the example with tricarballylic acid are summarized in Table 3.

[0135] In the table, C6-tetrol is 3-(hydroxymethyl)pentane-1,3,5-triol, C6-Triols include both propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol (excluding tricarballylic acid, see above). The C5-triol is 1,3,5-pentanetriol.

[0136] [Table 1]

[0137] [Table 2]

[0138] [Table 3]

Claims

1. (a) one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6; or (b) one or more reaction products of one or more compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6. A method for the preparation of a product comprising at least the following steps: (i) providing or preparing a starting material comprising a starting compound selected from the group consisting of an aliphatic tricarboxylic acid having a total of 6 carbon atoms, its esters, its anhydrides, and its salts; (ii) providing or preparing a solvent having a dielectric constant greater than the dielectric constant of n-butanol; and (iii) the starting compound provided or prepared in step (i), At temperatures ranging from 80°C to 155°C, - Hydrogen partial pressure in the range of 15MPa to 30MPa, in the solvent provided or prepared in step (ii), and Chemically converted in the presence of a heterogeneous hydrogenation catalyst comprising one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os, selectively hydrogenating the carboxyl, carboalkoxy, anhydride and / or carboxylate groups present in the starting compounds to the corresponding hydroxy groups to yield a product comprising one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6; The method comprising:

2. The starting compound is selected from the group consisting of α-functionalized aliphatic tricarboxylic acids, their esters, their anhydrides and their salts, preferably from the group consisting of α-hydroxyaliphatic tricarboxylic acids, their esters, their anhydrides and their salts, more preferably from the group consisting of citric acid, isocitric acid, their esters, their anhydrides and their salts, most preferably from the group consisting of citric acid, triethyl citrate and isocitric acid, or selected from the group consisting of α,β-unsaturated aliphatic tricarboxylic acids, their esters, their anhydrides and their salts, preferably from the group consisting of aconitic acid, their esters, their anhydrides and their salts, or selected from the group consisting of tricarballylic acids, their esters, their anhydrides, and their salts; The method of claim 1.

3. The product resulting in step (iii) is aliphatic polyols having 3 or 4 hydroxy groups and a total number of carbon atoms of 6, preferably 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol, and an aliphatic polyol having three hydroxy groups and a total of five carbon atoms, preferably 1,3,5-pentanetriol; 3. The method of claim 1 or 2, comprising one or more product compounds selected from the group consisting of:

4. the solvent having a dielectric constant greater than that of n-butanol provided or prepared in step (ii) comprises one or more components selected from the group consisting of water, methanol, ethanol, n-propanol, iso-propanol, ethylene glycol, propylene glycol and cyclic ethers; The solvent is preferably Water, and Aqueous mixtures containing more than 50% by weight of water, preferably more than 70% by weight, more preferably more than 90% by weight, based on the total amount of solvent. The method of claim 1 or 2, selected from the group consisting of:

5. The temperature in step (iii) is in the range of 120°C to 155°C, and / or selected to selectively prepare said aliphatic polyol instead of a lactone; The method according to claim 1 or 2.

6. The heterogeneous hydrogenation catalyst is one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os in a total amount of at least 90% by weight, preferably at least 95% by weight, based on the weight of the total amount of the heterogeneous hydrogenation catalyst, or one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os in a total amount of at least 10% by weight, relative to the total amount of the heterogeneous hydrogenation catalyst, in combination with one or more metals selected from the group consisting of Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au, wherein the total amount of metals selected from the group consisting of Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au is at least 98% by weight, relative to the total amount of the heterogeneous hydrogenation catalyst; The method according to claim 1 or 2.

7. The heterogeneous hydrogenation catalyst is supported by a support material, preferably the support material is selected from the group consisting of metal oxides, zeolites and carbon-based materials, preferably Al 2 O 3 , ZrO 2 , TiO 2 3. The method according to claim 1 or 2, wherein the material is selected from the group consisting of: SiC, carbon black and PTFE.

8. After step (iii), the following additional steps: - removing the solvent used in step (iii) by evaporation; chemically converting one or more of the resultant compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6, present in the product resulting from step (iii), to provide a product (b) comprising one or more reaction products of the one or more compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6; and adding one or more further chemicals to the one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6, present in the product resulting from step (iii), to result in a reaction mixture comprising the one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6; The method according to claim 1 or 2, further comprising carrying out one or more of the following steps:

9. 3. The method according to claim 1 or 2, wherein the starting material comprising a starting compound selected from the group consisting of aliphatic tricarboxylic acids, their esters, their anhydrides and their salts, preferably selected from the group consisting of citric acid and aconitic acid, is prepared or isolated from plant material, preferably prepared by sugar fermentation.

10. The product is (a) one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6, said product comprising: - a formulation comprising one or more materials selected from the group consisting of peptides, proteins, enzymes, microorganisms, DNA, RNA, and viruses; - paint and adhesive formulations; a reaction mixture for converting the aliphatic polyol into a polyalkoxylate, the reaction mixture being prepared after step (iii); a reaction mixture for preparing a polymer, preferably selected from the group consisting of polyurethanes, polyesters and polyacrylates, said reaction mixture being prepared after step (iii), and a reaction mixture for preparing an ester, acyclic ether, or cyclic ether of said one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6, said reaction mixture being prepared after step (iii). Selected from the group consisting of: Or, the product is (b) one or more reaction products of said one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6, said product comprising: a product comprising one or more polyalkoxylates, at least one of which is prepared in a further step carried out after step (iii) from one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range from 5 to 6, and a product comprising one or more polymers, preferably polymers selected from the group consisting of polyurethanes and polyesters, at least one of said polymers being prepared in a further step carried out after step (iii) from said one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms in the range from 5 to 6; Selected from the group consisting of: The method according to claim 1 or 2.

11. A formulation comprising one or more ingredients selected from the group consisting of enzymes. wherein the product comprises one or more product compounds selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol, and 3-(hydroxymethyl)-2-pentene-1,5-diol, and 1,3,5-pentanetriol; The product.

12. one or more product compounds selected from the group consisting of: aliphatic polyols having 3 or 4 hydroxy groups and a total number of carbon atoms of 6, preferably 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol and 3-(hydroxymethyl)-2-pentene-1,5-diol, and an aliphatic polyol having three hydroxy groups and a total of five carbon atoms, preferably 1,3,5-pentanetriol; or Mixtures of such products 3. Use of a compound selected from the group consisting of aliphatic tricarboxylic acids having a total number of carbon atoms of 6, their esters, their anhydrides and their salts, preferably citric acid, as starting compound in the process according to claim 1 or 2 for the preparation of Preferably, said use, wherein said product compound, or mixture of such product compounds, is produced in an amount of 100 kg or more, more preferably 500 kg or more, and even more preferably 1000 kg or more per batch.

13. one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os in a total amount of at least 90% by weight, preferably at least 95% by weight, relative to the total amount of the heterogeneous hydrogenation catalyst, or one or more metals selected from the group consisting of Mn, Re, Fe, Ru and Os in a total amount of at least 10% by weight, relative to the total amount of the heterogeneous hydrogenation catalyst, in combination with one or more metals selected from the group consisting of Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au, wherein the total amount of metals selected from the group consisting of Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au is at least 98% by weight, relative to the total amount of the heterogeneous hydrogenation catalyst; 3. Use of a heterogeneous hydrogenation catalyst in the process according to claim 1 or 2.

14. Use of one or more product compounds selected from the group consisting of aliphatic polyols having 3 or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6, - a formulation comprising one or more materials selected from the group consisting of peptides, proteins, enzymes, microorganisms, DNA, RNA, and viruses; - paint and adhesive formulations; a reaction mixture for converting one or more of said aliphatic polyols into polyalkoxylates; a reaction mixture for preparing a polymer, preferably selected from the group consisting of polyurethanes, polyesters and polyacrylates, and a reaction mixture for preparing an ester, acyclic ether, or cyclic ether of one or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of 5 to 6. The above use in a product selected from the group consisting of:

15. The use of one or more product compounds selected from the group consisting of 3-(hydroxymethyl)pentane-1,3,5-triol, propane-1,2,3-trimethanol, 3-(hydroxymethyl)-2-pentene-1,5-diol and 1,3,5-pentanetriol in a product selected from the group consisting of a formulation comprising one or more materials selected from the group consisting of enzymes.

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