Process for preparation of pyrrolidone-substituted polyols

Abstract

The invention relates to a method for producing pyrrolidone-substituted polyols in which substituted or unsubstituted oxacyclopentane-2-ones conforming to the general formula (I) are reacted with an amino alcohol of the general formula NH2-C (R7) ((CH2) m-OH)-(CH2) n-OH (II) or NH2-(CH2) o-CH (OH)-(CH2) p-OH (III) to produce pyrrolidone-substituted polyols.

Description

Technical Field

[0001] This invention relates to a method for preparing pyrrolidone-substituted polyols, particularly the preparation of pyrrolidone-substituted diols. Background Technology

[0002] With the rapid growth of the world's population, the increasing depletion of non-renewable fossil resources, and the escalating environmental pollution, reducing the chemical industry's dependence on fossil resources has become crucial. One approach is to leverage bio-based platform chemicals to drive the chemical industry's transition towards sustainable development.

[0003] 2-Aminopropane-1,3-diol (serine alcohol) and its substituted forms are widely used in the chemical industry. For example, there are reports on the preparation of polymerizable diols using serine alcohol as a raw material. CN 109467547 A describes a method for preparing 5-dimethylamino-1,3-dioxane-2-one by reacting serine alcohol with triphosgene. This 5-dimethylamino-1,3-dioxane-2-one can be further copolymerized with cyclic carbonate monomers and lactone monomers to prepare functional aliphatic polycarbonate and poly(ester-carbonate) copolymers. EP 2809760 B1 describes a method for eliminating odors using 2-aminopropane-1,3-diol or its substituted forms. EP 3063204 A1 describes a polymer formed by reacting an organic diepoxide or polyepoxide with a primary amine, amino alcohol, amino acid, hydroxy acid, glycol, or alcohol having a condensed or non-condensed aromatic imide group. WO 2020 / 154471 A1 describes a lactam-functionalized polymer prepared by reacting a dihydroxylactam with a functional unit having a hydroxyl reactive functional group.

[0004] Therefore, there is a need to develop alternative methods for preparing substituted amino diols (especially substituted 2-aminopropane-1,3-diol). Summary of the Invention

[0005] The purpose of this invention is to provide a method for preparing substituted amino polyols to overcome at least one of the defects in the prior art.

[0006] The objective of this invention is to achieve this by a method for preparing pyrrolidone-substituted polyols, wherein a substituted or unsubstituted oxacyclopentan-2-one conforming to the following general formula (I) is mixed with a polyol of the general formula NH2-C(R) 7 (CH2) m -OH) (CH2) n -OH(II) or NH2-(CH2) o -CH(OH)-(CH2) pThe -OH(III) amino alcohol reacts to form pyrrolidone-substituted polyols conforming to the following general formula (IV) or (V):

[0007]

[0008] in:

[0009] R 1 R 2 Each group is independently selected from groups including H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH; or

[0010] R 1 With R 2 Forms a double-bonded oxygen atom (carbonyl oxygen);

[0011] R 3 R 6 Each group is independently selected from groups including H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH; and

[0012] R 4 R 5 Each group is independently selected from groups including H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH, or

[0013] R 4 With R 5 Formation of double bonds;

[0014] R 7 Selected from H, -(CH2) q -OH and C1-C5-alkyl groups; and

[0015] m, n, o, p, and q are each independently selected from integers of 0, 1, 2, 3, 4, 5, 6, and 7.

[0016] Surprisingly, the method of this invention can prepare pyrrolidone-substituted polyols through a single-step reaction. Using this method, the crude yield of pyrrolidone-substituted polyols can exceed 95%. This method can utilize biomass reactants to prepare pyrrolidone-substituted polyols, demonstrating sustainability in both the sustainable reaction system and the economical use of raw materials.

[0017] Unless otherwise stated, the term "C1-C5-alkyl" encompasses straight-chain or branched alkyl groups having 1 to 5 carbon atoms. C1-C5-alkyl groups are preferably selected from groups including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, and / or neopentyl.

[0018] Unless otherwise stated, the term "C2-C5-alkenyl" encompasses straight-chain or branched alkenyl groups having 2 to 5 carbon atoms. C2-C5-alkenyl groups are preferably selected from groups including vinyl, propenyl, and butenyl groups.

[0019] Unless otherwise stated, in this invention, there is a distinction between compounds numbered using Arabic numerals and compounds numbered using Roman numerals; that is, they refer to different compounds in each case.

[0020] The one that can be used conforms to the general formula NH2-C(R) 7 (CH2) m -OH)-(CH2) n -OH (II) or NH2-(CH2) o -CH(OH)-(CH2) p -OH (III) amino alcohols, where R 7 Selected from H, -(CH2) q -OH and C1-C5-alkyl groups, and m, n and q as well as o and p can each be 0, 1, 2, 3, 4, 5, 6 or 7 independently.

[0021] The general formula is NH2-C(R) 7 (CH2) m -OH)-(CH2) n -OH (II) amino alcohols, where R 7 Selected from H, -(CH2) q -OH and C1-C5-alkyl groups, m, n and q are each independently 0, 1, 2, 3, 4, 5, 6 or 7, having at least two hydroxyl groups, but may also be triols.

[0022] In a preferred embodiment, the amino alcohol is a diol conforming to the following general formula: NH2-C(R 7 (CH2) m -OH)-(CH2) n -OH(II), where R 7 It is hydrogen or methyl, and m=n, selected from 0, 1, 2, 3, or m=0 and n=1 or 2, or m=1 and n=2, 3, 4, 5, 6 or 7. Preferably, the amino alcohol is of general formula (1):

[0023]

[0024] Where m and n are selected from 0, 1, 2, 3, or m=0 and n=1 or 2, or m=1 and n=2, 3, 4, 5, 6 or 7, and are selected from the group of compounds (4) to (15) shown below:

[0025]

[0026]

[0027]

[0028] In a particularly preferred embodiment, the amino alcohol is a diol conforming to the following general formula: NH2-C(R 7 (CH2) m -OH)-(CH2) n -OH(II), where R 7 It can be hydrogen or methyl, and m and n are preferably 1. These 2-aminopropane-1,3-diols are commonly referred to as serine alcohols, also known as methylserine alcohols.

[0029] In a further embodiment, the general formula NH2-C(R) 7 (CH2) m -OH)-(CH2) n The amino alcohol with -OH (II) is a triol with the following general formula (2), wherein R 7 -(CH2) q -OH:

[0030]

[0031] The preferred triol conforms to general formula (2): NH2-C(-(CH2) q -OH)((CH2) m -OH)-(CH2) n -OH, where m=n=q, is selected from 1, 2, 3. Preferred amino alcohols having the general formula (2) are selected from the group consisting of compounds (16) to (18).

[0032]

[0033]

[0034] Also usable amino alcohols include those conforming to the general formula NH2-(CH2). o -CH(OH)-(CH2) p Compounds of -OH(III), wherein o and p are preferably 1, 2, 3 or 4 independently.

[0035] Preferred formula (III) amino alcohol

[0036]

[0037] Selected from the group consisting of compounds (19) to (24) below:

[0038]

[0039]

[0040] The amino alcohol, particularly serine or methylserine, reacts with substituted or unsubstituted oxacyclopentan-2-ones conforming to general formula (I):

[0041]

[0042] in:

[0043] R 1 R 2 Each group is independently selected from groups including hydrogen, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH, or

[0044] R 1 With R 2 Forms a double-bonded oxygen atom (carbonyl oxygen);

[0045] R 3 R 6 Each group is independently selected from groups including hydrogen, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH; and

[0046] R 4 R 5 Each group is independently selected from groups including hydrogen, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH, or

[0047] R 4 With R 5 Double bonds are formed.

[0048] Preferably, R 1 and R 2 Each is independently selected from hydrogen and C1-C3-alkyl, especially methyl, or R 1 and R 2 It forms a double-bonded oxygen atom (carbonyl oxygen).

[0049] Preferably, R 3 and R 6 Each group is independently selected from hydrogen, C1-C5-alkyl, especially methyl, or C2-C5-alkenyl. In the C2-C5-alkenyl group, it is preferred that the unsaturated bond is not directly located on the ring. In R 3 or R 6 In the C2-C5-olefin embodiment, R 4 and R 5 Hydrogen is preferred.

[0050] Preferably, R4 and R 5 Each is independently selected from hydrogen, C1-C5-alkyl, especially methyl, or C2-C5-alkenyl, or R 4 With R 5 Double bonds are formed. In R 4 and R 5 In the implementation of the double bond formation, R 3 and R 6 Hydrogen is preferred.

[0051] In a preferred embodiment, the substituted or unsubstituted oxepane-2-one conforms to the following general formula (VI):

[0052]

[0053] in:

[0054] R 1 R 2 Each group is independently selected from groups including H and C1-C3-alkyl, or R 1 With R 2 The oxygen atom that forms a double bond (carbonyl oxygen); and

[0055] R 3 R 6 Each group is independently selected from groups including hydrogen, C1-C3-alkyl and / or C2-C3-olefin.

[0056] Preferred substituted or unsubstituted oxacyclopentan-2-ones are selected from the group consisting of compounds (25) to (38):

[0057]

[0058] A particularly preferred oxacyclopentane-2-one is γ-butyrolactone, the structure of which is shown in formula (25).

[0059] In an embodiment of this method, the oxacyclopentan-2-one shown in formula (VI) reacts with serine alcohol to produce the pyrrolidone-substituted diol shown in formula (VII):

[0060]

[0061] in:

[0062] R 1 R 2 Each is independently selected from groups containing H and C1-C3-alkyl groups, or R 1 and R 2 It consists of a double-bonded oxygen atom (carbonyl oxygen); and

[0063] R 3 R 6Each group is independently selected from groups including hydrogen, C1-C3-alkyl and / or C2-C3-olefin.

[0064] A high yield can be obtained when the reaction is carried out using serine alcohol and an oxacyclopentan-2-one of general formula (VI). Preferably, R 1 R 2 R 3 R 6 Each is independently selected from hydrogen and C1-C3-alkyl, or R 1 and R 2 It is a carbonyl oxygen, and R 3 and R 6 It is hydrogen.

[0065] In a preferred embodiment, γ-butyrolactone is reacted with serine to generate a pyrrolidone-substituted diol of general formula (40).

[0066]

[0067] Oxepin-2-one can be used in stoichiometric ratio with the amino alcohol, or preferably in excess. The amount of oxepin-2-one relative to the amino alcohol can range from >1 equivalent to ≤2 equivalents. In embodiments, the reaction is carried out with an excess of oxepin-2-one and the amino alcohol, with an excess ranging from ≥1.2 equivalents to ≤1.5 equivalents. Using this trace excess of oxepin-2-one relative to the amino alcohol yields a higher reaction yield.

[0068] In some embodiments, the reaction is carried out in aqueous solution or under solvent-free conditions. For example, γ-butyrolactone is a liquid at room temperature (corresponding to 20 ± 2°C) and can react with serine, which is a solid at room temperature, without the need for additional solvent. The reaction is preferably carried out in an aqueous solution with a small amount of water added. This helps to increase the reaction yield. Preferably, the amount of solvent used should be as low as possible, for example, sufficient to dissolve one or more solid reactants. Specifically, the amount of water used per gram of solid reactant (especially serine) can be in the range of ≥1.5 mL / g to ≤2 mL / g, particularly in the range of ≥1.5 mL / g to ≤1.8 mL / g.

[0069] In a preferred embodiment, the reaction is carried out in a temperature range of ≥150°C to ≤220°C, preferably in a temperature range of ≥180°C to ≤200°C. Good yields are particularly obtained within this temperature range. Yields decrease at lower temperatures, while higher temperatures may lead to product decomposition. The reaction time can range from ≥2 hours to ≤20 hours, preferably from ≥12 hours to ≤16 hours.

[0070] This method can, in principle, be carried out continuously or intermittently, for example, in a stirred tank reactor, a synthesis reactor (such as a stirred reactor), or an autoclave. The reaction is preferably carried out under a nitrogen atmosphere. For this purpose, the autoclave can be purged with nitrogen before the reaction.

[0071] In a preferred embodiment, 10 mmol (1 equivalent) of serine was dissolved in 1.5 mL of deionized water and reacted with 12-15 mmol (1.2-1.5 equivalent) of γ-butyrolactone at 180-200°C for 16-20 hours.

[0072] The reaction mixture obtained by this method can be purified using conventional methods, such as thermal separation methods like distillation or rectification. In a preferred embodiment, the pyrrolidone-substituted polyol is purified by extraction with ethyl acetate in a temperature range of ≥85°C to ≤95°C. For example, the temperature can be set about 10 degrees above the boiling point of ethyl acetate (about 87°C). This thermal extraction with ethyl acetate yields the product as pure white crystals. Prior to such purification, it is preferable to remove water added as a solvent or generated in the reaction.

[0073] In summary, this paper presents a method for the high-yield preparation of polyols based on pyrrolidone-substituted diols using readily available and resource-efficient reactants in a single reaction.

[0074] This invention further provides pyrrolidone-substituted polyols, particularly polyols conforming to the following general formula (IV) prepared by the methods described herein:

[0075]

[0076] in:

[0077] R 1 R 2 Each group is independently selected from groups including H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH, or

[0078] R 1 and R 2 Forms a double-bonded oxygen atom (carbonyl oxygen);

[0079] R 3 R 6 Each group is independently selected from groups including H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH; and

[0080] R 4 R 5The groups are independently selected from H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH, or R. 4 and R 5 Formation of double bonds;

[0081] R 7 Selected from H, -(CH2) q -OH and C1-C5-alkyl groups; and

[0082] m, n, and q are each an independent integer selected from 0, 1, 2, 3, 4, 5, 6, and 7.

[0083] Preferably, R 1 and R 2 Each is independently selected from hydrogen and C1-C3-alkyl, especially methyl, or R 1 and R 2 A double-bonded oxygen atom (carbonyl oxygen) is formed. Preferably, R 3 and R 6 Each group is independently selected from hydrogen, C1-C5-alkyl (especially methyl), or C2-C5-alkenyl. In the case of C2-C5-alkenyl groups, it is preferable that the unsaturated bond is not directly located on the ring. In R 3 or R 6 In embodiments where the group is a C2-C5-olefinic group, R 4 and R 5 Preferably, it is hydrogen. Preferably, R 4 and R 5 Each is independently selected from hydrogen, C1-C5-alkyl (especially methyl) or C2-C5-alkenyl, or R 4 and R 5 Double bonds are formed. In R 4 and R 5 In the implementation of the double bond formation, R 3 and R 6 Hydrogen is preferred.

[0084] Preferred pyrrolidone-substituted diols conform to the following formula (VII):

[0085]

[0086] in:

[0087] R 1 R 2 Each group is independently selected from groups including hydrogen and C1-C3-alkyl groups, or R 1 With R 2 Forms a double-bonded oxygen atom (carbonyl oxygen); and

[0088] R 3 R 6Each group is independently selected from groups including hydrogen, C1-C3-alkyl and / or C2-C3-olefin.

[0089] Preferably, R 1 R 2 R 3 R 6 Each is independently selected from hydrogen and C1-C3-alkyl, or R 1 With R 2 It is a carbonyl oxygen, and R 3 With R 6 Hydrogen is used. Particularly preferred pyrrolidone-substituted diols are those with the following formulas (40), (41), and (42):

[0090]

[0091] Unless otherwise stated, the technical and scientific terms used have the meanings that are commonly understood by one of ordinary skill in the art.

[0092] Examples and illustrations used to illustrate the present invention are shown below.

[0093] Chemicals:

[0094] The reactants used were purchased from Sigma-Aldrich, Fluorochem, Aldrich, or ABCR. The solvents were purchased from Chemsolute GmbH.

[0095] 1 H nuclear magnetic resonance (NMR):

[0096] The reaction products were analyzed using a Bruker DPX-400 Fourier transform nuclear magnetic resonance spectrometer at 400 MHz and room temperature. 1 ¹H NMR determination. Some products were identified by two-dimensional spectra (COSY, HMBC, HSQC). δ values ​​and chemical shifts were based on the residual proton signal in the deuterated solvent: ¹H: DMSO-d₆ (δH = 2.50 ppm); DMSO-d₆ (δC = 39.52 ppm). Mesitylene was used as a standard for quantitative analysis. Attached Figure Description

[0097] In the diagram:

[0098] Figure 1 The figure shows the reaction yield of succinic anhydride and serine alcohol at different temperatures and reaction times. Detailed Implementation

[0099] Example 1: Determination of the yield of γ-butyrolactone in the reaction with serine at different temperatures and reaction times

[0100]

[0101] 1.14 mL of γ-butyrolactone (GBL) (15 mmol, 1.5 equivalent), 0.9111 g of serineol (10 mmol, 1 equivalent), and 1.5 mL of water were added to a 50 mL autoclave (made in the laboratory). The autoclave was purged three times with nitrogen (2 minutes each time) under stirring. The autoclave was then sealed and reacted at 180 °C, 200 °C, or 220 °C for 4, 8, 12, 16, or 20 hours, respectively. 1 The yield of crude product was determined by ¹H NMR.

[0102] Figure 1 The crude yields of γ-butyrolactone and serine were shown in screening experiments under different reaction conditions. Figure 1 As shown, the optimal yield occurred within a reaction period of 12 to 20 hours across all studied temperature ranges. In this screening experiment, the optimal reaction conditions were 200°C for 12 hours.

[0103] The crude product was purified with ethyl acetate (87°C) to obtain pure white crystals.

[0104] Example 2: Determination of the yield of γ-butyrolactone in reaction with serine under different reactant ratios and solvent conditions.

[0105] γ-Butyrolactone and serine were reacted in a nitrogen-inert 50 mL high-pressure reactor at 200 °C for 16 hours. Four parallel reactions were conducted, using equimolar ratios of γ-butyrolactone to serine and γ-butyrolactone (20 mmol / L, 2 equivalents) to serine (10 mmol / L, 1 equivalent), respectively. Reactions were carried out without solvent and with the addition of 2 mL of water. 1 The yield of crude product was determined by ¹H NMR.

[0106] These experiments revealed that using an excess (1.5 equivalents) of γ-butyrolactone resulted in higher product yields. Furthermore, the experimental group using water as a solvent also exhibited higher yields. Further studies on the reactant ratio and solvent showed that a serine to γ-butyrolactone ratio of 1:1.2 was sufficient to achieve the corresponding yield increase. Moreover, using 1.5 mL of solvent per 10 mmol of serine resulted in the corresponding yield increase.

[0107] Example 3: Study on the reaction between serinel and succinic anhydride

[0108]

[0109] Under nitrogen inert protection, in a 50 mL high-pressure reactor, using water as a solvent, 12 mmol (1.2 equivalents) of succinic anhydride and 10 mmol (1 equivalent) of serine were reacted at 200°C for 1 to 20 hours. 1 The yield of the crude product was determined by ¹H NMR. A summary of the crude product yields is shown in Table 1 below:

[0110] Table 1: Crude yield of the reaction of 1.2 equivalents of succinic anhydride with 1 equivalent of serine alcohol

[0111]

[0112] When the reaction time exceeds 12 hours, it is speculated that the formation of byproducts led to a decrease in product yield.

[0113] Example 4: Study on the reaction of serinel with 4-pentanolide

[0114]

[0115] After nitrogen inertization, 12 mmol (1.2 equivalents) of 4-pentanolide and 10 mmol (1 equivalent) of serine were reacted in a 50 mL high-pressure reactor with water as the solvent at 200°C for 1 to 20 hours, and the reaction was carried out by... 1 The yield of the crude product was determined by ¹H NMR. A summary of the crude product yields is shown in Table 2 below:

[0116] Table 2: Crude yield of the reaction of 4-pentanolide with serine

[0117]

[0118] It is speculated that the presence of the methyl group led to the reduced yield.

[0119] Example 5: Study on the reaction of serinel with other lactones

[0120] After nitrogen inertization, 12 mmol (1.2 equivalents) of α-valerol, 5-methyl-2-furanone or furanol were reacted with 10 mmol (1 equivalent) of serine alcohol in a 50 mL high-pressure reactor at 200°C for 16 hours using water as the solvent.

[0121] In these experiments, the reaction with α-valerol was successful, while the reactions with 5-methyl-2-furanone and furanol did not yield satisfactory results.

[0122] Example 6: Study on the reaction of γ-butyrolactone with other aminodiols or aminotriols

[0123] After nitrogen inertization, 12 mmol (1.2 equivalents) of γ-butyrolactone was reacted with 10 mmol (1 equivalent) of 3-aminopropane-1,2-diol or the triol 2-amino-2-(hydroxymethyl)-propane-1,3-diol in a 50 mL high-pressure reactor at 200°C for 16 hours using water as the solvent. In these experiments, the reactions of the diol and the triol successfully yielded the target product.

[0124] The combined results show that pyrrolidone-substituted diols and triols can be prepared in good yields by reacting substituted or unsubstituted oxepane-2-ones with amino diols or amino triols in a one-step reaction.

[0125] The invention upon which this patent application is based originated from a project funded by the German Federal Ministry of Education and Research (BMBF), grant number 031B1141A.

Claims

1. Process for the preparation of pyrrolidone-substituted polyols, characterized in that: Substituted or unsubstituted oxolane-2-ones of the following general formula (I) are reacted with amino alcohols of the general formula NH2-C(R 7 ((CH2) m -OH)-(CH2) n -OH(II) or NH2-(CH2) o -CH(OH)-(CH2) p -OH(III) to form pyrrolidone substituted polyols of the following general formula (IV) or (V): wherein: R 1 , R 2 each independently is selected from the group comprising H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH, or R 1 with R 2 forming a double bond oxygen atom; R 3 , R 6 each independently is selected from the group comprising H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH; and R 4 , R 5 each independently is selected from the group comprising H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH, or R 4 with R 5 forming a double bond; R 7 selected from the group consisting of H, -(CH2) q -OH and C1-C5-alkyl; and m, n, o, p, q are each independently an integer selected from 0, 1, 2, 3, 4, 5, 6, 7.

2. The method of claim 1, wherein: said amino alcohol is of the formula NH2-C(R 7 ((CH2) m -OH)-(CH2) n -OH (1), wherein R 7 is selected from H or methyl, and m = n and are selected from 0, 1, 2, 3, or m = 0 and n = 1 or 2, or m = 1 and n = 2, 3, 4, 5, 6 or 7; or said amino alcohol is of the formula NH2-C(-(CH2) q -OH ((CH2) m -OH)-(CH2) n -OH (2), wherein m = n = q and are selected from 1, 2, 3.

3. The method according to claim 1 or 2, characterized in that: The oxolane-2-one of formula (VI) is reacted with serinol to form a pyrrolidinone substituted dihydric alcohol of formula (VII): wherein: R 1 , R 2 are each independently selected from the group consisting of hydrogen and C1-C3-alkyl, or R 1 and R 2 form a double-bonded oxygen atom; R 3 , R 6 each independently is selected from the group consisting of hydrogen, Ci-C3-alkyl and / or C2-C3-alkenyl.

4. The method according to any of the preceding claims, characterized in that, The oxolane-2-one is used in excess in the reaction relative to the amino alcohol, the excess ranging from > 1.2 equivalents to < 1.5 equivalents.

5. The method according to any of the preceding claims, characterized in that, The reaction is carried out in aqueous solution or under solvent-free conditions.

6. The method according to any of the preceding claims, characterized in that The reaction is carried out in a temperature range of > 150 °C to < 220 °C, preferably in a temperature range of > 180 °C to < 200 °C.

7. The method according to any of the preceding claims, characterized in that, The reaction time is in the range of > 2 hours to < 20 hours, preferably in the range of > 12 hours to < 16 hours.

8. The method according to any of the preceding claims, characterized in that The pyrrolidinone substituted polyhydric alcohol is purified by extraction with ethyl acetate in a temperature range of > 85 °C to < 95 °C.

9. A pyrrolidinone substituted polyhydric alcohol according to the following general formula (IV), in particular prepared by the process according to claims 1 to 8: wherein: R 1 , R 2 each independently is selected from the group comprising H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH, or R 1 With R 2 forming a double bond with the oxygen atom; R 3 , R 6 each independently is selected from the group consisting of H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH; and R 4 , R 5 each independently is selected from the group comprising H, C1-C5-alkyl, C2-C5-alkenyl, Cl, Br, I, F and / or OH, or R 4 with R 5 forming a double bond; R 7 selected from the group consisting of H, -(CH2) q -OH and C1-C5-alkyl; and m, n, q are each independently an integer selected from 0, 1, 2, 3, 4, 5, 6, 7.

Images