Process for producing alkali o-cresolate or alkali p-xylenolate

Abstract

The present invention relates to a process for producing alkaline o-cresolate or alkaline p-xylenolate of o-cresol or p-xylenol, respectively. This process, which uses an extruder to react the compound of formula (II) with sodium hydroxide or potassium hydroxide, has been shown to be highly advantageous and to enable significantly faster reaction times and continuous processes. TIFF2026518499000027.tif38147 In the formula, R is either H or CH3, Y is SO3H, SO3-X+, or Cl, and X is either Na or K, preferably Na.

Description

Detailed Description of the Invention

[0001] [Technical Field] The present invention relates to the field of production of o-cresol and p-xylenol.

[0002] [Background of the Invention] The compounds o-cresol (= 2-methylphenol) and p-xylenol (= 2,5-dimethylphenol) are very valuable components used for various purposes. Xylenol is used as a starting material for insecticides, antioxidants or pharmaceuticals.

[0003] Cresol is a precursor or synthetic intermediate for other compounds and materials, including plastics, insecticides, pharmaceuticals and dyes.

[0004] The compound o-cresol is used as an industrial solvent and in disinfectants and fungicides, or for the production of herbicides, pest control agents, dyes, drugs, antioxidants, fragrances and other chemicals for synthetic resins, as a food antioxidant, fiber scouring agent, surfactant, metal cleaning agent and floating ore agent, and as a component of cleaning compounds, degreasing agents, paints and paint strippers, adhesives, fiber treatments, wood preservatives and cutting oils, and is therefore of great interest.

[0005] The compound p-xylenol is used, for example, in the synthesis of xylenol phthalein, xylenol blue or bromoxylenol blue, which are pH indicators, and as the main raw material for gemfibrozil, which can be used as a drug for treating abnormal blood lipid levels.

[0006] The compound p-xylenol has been of significant interest for the large-scale industrial synthesis of 2,3,6-trimethylphenol or 2,3,5-trimethylphenol, or 2,3,5-trimethylhydroquinone, or α-tocopherol.

[0007] Currently, 2,5-dimethylphenol is prepared by alkaline fusion of sulfonated p-xylene using a batch process.

[0008] Alkali fusion is the most concerning process in terms of corrosion and safety issues, especially when the process is a batch process.

[0009] For example, Chinese Patent No. 102627531 discloses such a batch process.

[0010] Chinese Patent No. 114805034 discloses a process in which, in the first step, sodium 2,5-dimethylbenzenesulfonate and a strong base are mixed in a rake dryer, and after 5 hours of grinding, sieving, and drying, a very fine powder (1-5 micrometers) is obtained. Then, in the second step, this powder is transferred to a spiral pipe reactor and reacted at a high temperature for a long period of 1-5 hours, and in the third step, p-xylenol is obtained by quenching with acid. Due to the use of a rake dryer and spiral pipe, the disclosed process is very slow, and in particular, it is necessary to prepare the fine powder in the first step.

[0011] The use of extruders to mix and compound thermoplastic materials is well known in the field of thermoplastics.

[0012] [Overview of the prefecture] The problem to be solved is to find a rapid and efficient process for preparing alkali o-cresolates or alkali p-xylenolates that does not require a long drying and grinding process to form a very fine powder.

[0013] Surprisingly, it was found that the process of claim 1 provides a solution to this problem.

[0014] Using an extruder to melt and react the compound of formula (II) with the base XOH is highly advantageous because it eliminates the need to grind the sodium 2,5-dimethylbenzenesulfonate and base XOH before the reaction in step b), and is significantly faster than known processes (minutes instead of hours). High yields and conversion rates were observed despite the shorter reaction time. The shorter exposure to high temperatures in reaction step b) reduces the amount of undesirable decomposition products.

[0015] The process of the present invention is extremely advantageous in terms of reducing energy costs, time, and safety risks during production. These advantages are even more pronounced when the process can be carried out as a complete continuous process.

[0016] Further aspects of the present invention are the subject of further independent claims. Particularly preferred embodiments are the subject of dependent claims.

[0017] [Detailed description of the invention] In the first aspect, the present invention relates to formula (I) [ka] The compound of formula (II) [ka] A process for producing from the compound, a) A step of providing a compound of formula (II), b) A step of melting and reacting the compound of formula (II) with XOH in an extruder 1 at a temperature above the melting point of XOH, particularly 320°C to 450°C, more particularly 330°C to 450°C, even more particularly 360°C to 450°C, preferably 360°C to 420°C, and more preferably 380°C to 400°C, to obtain the compound of formula (I). In a process including, R is either H or CH3, and Y is SO3H or SO3 - X +、or Cl, and X is either Na or K, preferably Na, in a process characterized by

[0018] For the sake of clarity, some terms used in this specification are defined as follows.

[0019] In this specification, when the same symbol or group exists in some formulas, the definition of the said group or symbol made in relation to one specific formula is also applicable to other formulas containing the same said symbol.

[0020] The melting point of a specific substance in this specification is used as the temperature at which the said substance melts at ambient temperature (23 °C) and ambient pressure (1013 millibars).

[0021] In this specification, the term "essentially free of water" is used to mean that the substance in question contains only a trace amount of water, particularly 10% by weight or less of water.

[0022] [Step a)] In step a), a compound of formula (II) is provided.

[0023] The compound of formula (II) is selected from the group consisting of compounds of formula (I-A), (I-B) and (I-C) [Chemical formula] .

[0024] The compound of formula (II-A) can be prepared by sulfonating the compound of formula (III), particularly by reacting sulfuric acid with the compound of formula (III). Particularly preferred is concentrated sulfuric acid. [Chemical formula]

[0025] The above reaction typically yields a mixture of isomers containing the compound of formula (II-A). Those skilled in the art know that the amount of the compound of formula (II-A) in the mixture is strongly dependent on the reaction conditions in the sulfonation.

[0026] In one embodiment, an isomer mixture containing the compound of formula (II-A) is used in the process of the present invention. In another embodiment, isomer (II-A) is isolated from the mixture and used in the process of the present invention.

[0027] The compound of formula (II-B) can be prepared by neutralizing the compound of formula (II-A), particularly as will be shown in more detail later herein.

[0028] The compound of formula (II-C) can be prepared by the reaction of the compound of formula (III) with chlorine.

[0029] The aforementioned reaction is known to those skilled in the art and typically yields a mixture of isomers containing the compound of formula (II-C). In one embodiment, the mixture of isomers containing the compound of formula (II-C) is used in the process of the present invention. In another embodiment, the isomer (II-C) is isolated from the mixture and used in the process of the present invention.

[0030] The compound of formula (II) is preferably either the compound of formula (II-A) or the compound of formula (II-B).

[0031] The compound of formula (II) is [ka] It is selected from the group consisting of the following.

[0032] It is preferable that R = CH3.

[0033] Therefore, the preferred compound of formula (II) is the compound of formula (II-0), and accordingly, the preferred compound of formula (I) is the compound of formula (I-0). [ka]

[0034] Furthermore, Y=SO3 - X + , especially SO3 - Na + It is preferable that this be the case.

[0035] The compound of formula (II) is more preferably a compound of formula (II-B), particularly (II-B2), and preferably (II-BB). [ka]

[0036] Therefore, preferred compounds of formula (I) are compounds of formula (IA), preferably compounds of formula (I-BB). [ka]

[0037] In the case of potassium salts, the most preferred compound of formula (II) is the compound of formula (II-CC), and the most preferred compound of formula (I) is the compound of formula (I-CC). [ka]

[0038] [Reaction step b)] In step b), in order to obtain the compound of formula (I), the compound of formula (II) is melted and reacted with XOH in the extruder 1 at a temperature exceeding the melting point of XOH, particularly 320°C to 450°C, more particularly 330°C to 450°C, even more particularly 360°C to 450°C, preferably 360°C to 420°C, and more preferably 380°C to 400°C.

[0039] The melting point of NaOH is approximately 320°C, while the melting point of KOH is 360°C.

[0040] Therefore, as part of the temperature range shown above, it is clear that temperatures in the range of 320°C to 360°C are suitable only when NaOH is used in the reaction.

[0041] Step b) of melting and reacting the compound of formula (II) with XOH is preferably carried out in the presence of a molar excess of XOH such that the molar ratio of XOH to and / or the compound of formula (II) is >2, particularly 2 to 4, preferably 2 to 3, more preferably 3 to 2.5.

[0042] The molar ratio is preferably in the range of 2.01 to 3.99, more preferably 2.01 to 2.99, and more preferably 2.01 to 2.49.

[0043] A mixture of NaOH and KOH can also be used. However, it is most preferable to use NaOH alone.

[0044] In process b), temperatures exceeding 450°C are mainly possible.

[0045] Higher temperatures result in faster reaction times, and therefore, primarily, shorter residence times in the extruder. However, this leads to the formation of larger amounts of decomposition products of the compound of formula (I) or (II). Therefore, it is recommended to carry out the reaction in step b) at a temperature that is not excessively high. The formation of such decomposition products is particularly pronounced when using compounds of formula (II) or (I) with extended residence times.

[0046] The residence time of the compound of formula (II) or (I) is controlled by the extrusion rate, i.e., the rotational speed of the extrusion screw. If the residence time is too short, the reaction will not be completed, and a considerable amount of unreacted compound of formula (II) will be observed in the product coming out of the extruder. In particular, if the residence time is too long at high temperatures, especially above 450°C, there is a risk that the compound of formula (I) or (II) will undergo thermal decomposition, forming undesirable byproducts.

[0047] The reaction in step b) takes place inside the extruder.

[0048] Extruder 1 comprises at least, - Casing 6, - Cavity 5 inside casing 6, - Extruder screw 7 inside cavity 5, - Inlet 2 for compound of formula (II), - Exit 3 for compound of formula (I), - A mixture of XOH and the compound of formula (II) inside cavity 5 Includes.

[0049] In other words, an extruder containing XOH and the compound of formula (II) represents a device for producing the compound of formula (I).

[0050] The compound of formula (II) may be NaOH, which can be introduced into the extruder 1 through the inlet 2 of the extruder.

[0051] The base XOH, preferably NaOH, can be introduced into the extruder 1 as a mixture with the compound of formula (II) through inlet 2 of the extruder or preferably through separate inlets 4 for KOH and / or NaOH.

[0052] It is preferable to transfer XOH to the extruder in the form of solid XOH or molten XOH. Preferably, XOH is introduced into the extruder as molten material.

[0053] Preferably, the extruder 1 further includes a heating element 9 capable of adjusting the temperature of the reaction mixture of XOH and the compound of formula (II) within the extruder 1. This is particularly advantageous when the reaction mixture exhibits a temperature gradient from a lower temperature near the inlet point of the extruder inlet 2 to a higher temperature at the outlet 2 of the extruder. The temperature difference of this temperature gradient is preferably at least 20K, and more preferably at least 40K.

[0054] Therefore, it is preferable that the temperature of the material in the inlet 2 region of the extruder 1 is lower than that in the outlet 3 region of the extruder 1.

[0055] During the reaction, some gas is generated. Therefore, it is more preferable that the extruder includes at least one degassing outlet 10. This degassing outlet allows the gas to escape from the extruder. The location of such a degassing outlet 10 is selected along the axis of the extruder so that the gas formed during the reaction does not create high pressure inside the extruder, which may be important from a safety standpoint. Typically, the degassing outlet 10 includes means for controlling pressure release, such as a pressure control valve 11.

[0056] Extruder 1 is either a single-screw extruder or a multi-screw extruder.

[0057] Compared to single-screw extruders, multi-screw extruders are more efficient at producing a homogeneous mixture of reaction partners. While the mixing efficiency of single-screw extruders can be improved by using mixing elements, it is not as efficient as that of multi-screw extruders. A wide variety of multi-screw extruders are available, with various structures, having parallel or conical screws capable of rotating in the same direction (co-rotation) or in opposite directions (reverse rotation), and potentially having different degrees of meshing. In contrast to spiral pipe reactors, which have no moving internal parts and therefore mixing occurs solely by the fluid flow itself, extruders have actively rotating screws that are extremely efficient at mixing. Thus, extruders can handle even very coarse raw materials to obtain a homogeneous mixture, which is not possible with spiral pipe reactors. Extruders are known to be very efficient.

[0058] The extruder 1 is preferably a twin-screw or triple-screw extruder.

[0059] [Neutralization process] When the compound of formula (II) is a compound of formula (II-B), particularly formula (II-B2), and preferably formula (II-BB), the compound is preferably prepared by neutralizing a compound of formula (II-A) or (II-A2), respectively. [ka]

[0060] Neutralization is preferably carried out by reaction with NaOH and / or KOH, preferably with NaOH.

[0061] The neutralization of the compound of formula (II-B) may be carried out inside or outside the extruder.

[0062] In one of these embodiments, the neutralization reaction takes place inside the extruder.

[0063] Therefore, the compound of formula (II) is the compound of formula (II-B), preferably in step a0. a0) A step of neutralizing the compound of formula (II-A), particularly formula (II-A2), with XOH in an extruder at a temperature of 100°C to 200°C, particularly 100°C to 180°C, more particularly 100°C to 150°C, preferably 110°C to 130°C, to form the compound of formula (II-B). [ka] It is a compound of formula (II-B) prepared by [method / method].

[0064] In one embodiment, the neutralization step a0) is carried out in the same extruder as step b). However, in this case, the neutralization is preferably carried out further downstream of the extruder, i.e., near the compartment near the inlet of the extruder, at a lower temperature than the reaction step b) which occurs closer to the outlet of the extruder.

[0065] However, in a preferred method, the neutralization step a0) is preferably performed in a separate extruder.

[0066] In other words, it is preferable that the neutralization step (a0) is carried out in the first extruder 1a, the melting reaction step (b) is carried out in the second extruder 1b, and the compound of formula (II) is transferred from the outlet 3a of the first extruder 1a to the inlet 2b of the second extruder 1b.

[0067] It is highly preferable that the transfer of material from the first extruder 1a to the second extruder 1b be carried out by a connecting means 12 that is closed off from the environment.

[0068] This makes it possible to make the process of producing compound (I) from compound (II) a continuous process.

[0069] Step a0), in which the compound of formula (II) is neutralized with sodium hydroxide and / or potassium hydroxide, is preferably carried out in the presence of a molar excess of XOH such that the molar ratio of XOH to the compound of formula (II) is >1, particularly 1 to 2, preferably 1 to 1.5, and more preferably 1 to 1.25.

[0070] The molar ratio is preferably in the range of 1.01 to 1.99, more preferably 1.01 to 1.49, and more preferably 1.01 to 1.24.

[0071] The compound of formula (II-A), and especially formula (II-A2), is supplied to the extruder at a temperature of preferably 100°C to 200°C, particularly 100°C to 180°C, more particularly 100°C to 150°C, and preferably 110°C to 130°C. At this temperature, the compound of formula (II-A), and especially formula (II-A2), forms a viscous liquid.

[0072] The base XOH is supplied to the extruder as commercially available pearls or pellets, preferably several millimeters in size.

[0073] By using an extruder, coarse particles of the compound (II-A) or (II-A2) or XOH, up to several millimeters in size, can be used without any problems. Therefore, prolonged grinding or pulverization is not required.

[0074] A mixture of NaOH and KOH may also be used in the neutralization step a0).

[0075] However, it is most preferable to use NaOH alone.

[0076] The neutralization reaction between each compound of formula (II-A) or (II-A2) and the base XOH produces a stoichiometric amount of water.

[0077] The presence of a large amount of water in the reaction of step b) is undesirable, therefore the neutralization step a0) is carried out at a high temperature, i.e., above 100°C. In step a0), temperatures mainly exceeding 200°C are possible. However, excessively high temperatures can lead to a significant buildup of gas pressure, which may cause safety problems, so it is recommended that neutralization a0) be carried out at a temperature that is not excessively high.

[0078] Since reaction step b) is carried out at a high temperature, it is highly recommended to avoid or reduce as much as possible the amount of water in the starting products, particularly the compound of formula (II) and XOH, that forms vapor (i.e., water vapor) at the reaction temperature. Because NaOH and KOH are highly hygroscopic, it is preferable to store these compounds in a sealed container for water and vapor before use and to carry out the entire process of the present invention under a closed and / or inert atmosphere. It is also preferable that the starting materials do not contain water or at least are essentially water-free.

[0079] The residence time of the compound of formula (II) or (I) is controlled by the extrusion speed, i.e., the rotation speed of the extrusion screw. If the residence time is too short, the reaction will not be completed, and a considerable amount of unreacted compound of formula (II) will be observed in the product coming out of the extruder. In particular, if the residence time is too long at high temperatures, especially above 450°C, there is a risk that the compound of formula (I) or (II) will undergo thermal decomposition, forming undesirable byproducts.

[0080] Neutralization is a very fast reaction, and is significantly faster even at lower temperatures than the reaction in step b). Therefore, it was observed that the residence time in the extruder 1a during the neutralization step a0) can be significantly shorter than the residence time in the extruder 1b during the reaction step b).

[0081] The residence time in the first extruder 1a was typically found to be less than 1 minute, particularly 30 to 2 minutes, preferably 30 to 60 seconds.

[0082] The residence time in the second extruder 1b was typically found to be several minutes, particularly 3 to 30 minutes, preferably 10 to 20 minutes.

[0083] To improve the timing of steps a0) and b) in the continuous process framework, the residence time in the first extruder can be extended so that the residence times in both extruders 1a and 1b are the same, i.e., typically by several minutes, particularly 3 to 30 minutes, preferably 10 to 20 minutes. Extending the residence time in the first extruder 1a in this way is not so detrimental because the decomposition reaction does not proceed significantly at the relatively low temperature in the first extruder 1a.

[0084] To optimize productivity and reduce production costs, it is preferable that the entire process of the present invention be a continuous process. This goal can be easily achieved by the features described above.

[0085] In a preferred embodiment, the material exiting the extruder 1, particularly the second extruder 1b, is transferred to a heated vessel, particularly a heated tubular reactor, or pipe reactor, or spiral pipe reactor. It is advantageous to heat the heated vessel to the same temperature range as the second extruder. Allowing the product to remain in the heated vessel for an extended period of time can yield higher yields and / or allow the extruder to operate at a faster extrusion rate, thereby resulting in higher overall production volume for the process apparatus.

[0086] The reaction product, i.e., the compound of formula (I), is preferably transferred after step b) to a container 13 containing water, particularly an aqueous sulfite solution, preferably an aqueous Na2SO3 solution, along with any excess molten XOH. Since the compound of formula (I) has limited solubility in water, it can be easily isolated, for example, by a filter or frit. If necessary, the compound of formula (I) thus isolated can be further purified.

[0087] This transfer is preferably achieved by a connecting means 22, such as a tube, between the outlet 3 of the extruder, particularly the outlet 3b of the second extruder, and the container 13 containing water.

[0088] To enable a smooth reaction and preferably a constant mass flow rate continuously, it is preferable to use a pump to supply the starting product and / or to rapidly process the product formed after exiting the extruder. Preferred pumps are gear or screw pumps.

[0089] It will be apparent to those skilled in the art that all components of the extruder that come into contact with the starting product, reaction mixture, or reaction product, the pipes that end up in the extruder, the tubes leading to or from the extruder, or the pumps involved in mass flow are selected to be made from materials that are chemically resistant to the respective chemicals they come into contact with at the temperatures at which they are used during operation.

[0090] Compounds of formula (IV), particularly (IV-B), can be prepared using compounds of formula (I), especially formula (I-BB) or (I-CC), preferably (I-BB). [ka]

[0091] Therefore, further aspects of the present invention relate to formula (IV), and in particular formula (IV-B) [ka] In the process of producing the compound, i) Through a process described in great detail above, equation (I), in particular equation (I-0) [ka] The process of preparing the compound, followed by, c) A step of acidifying the compound of formula (I), particularly formula (I-0), with an acid to obtain the compound of formula (IV), particularly formula (IV-B). The process is characterized by including, where R is either H or CH3, preferably CH3.

[0092] The acid used in step c) for acidification is typically an inorganic acid, particularly hydrochloric acid or sulfuric acid, preferably diluted HCl or H2SO4.

[0093] It is advantageous to acidify the compound of formula (I) in water to obtain a pH of 5 or less.

[0094] It is particularly preferable to use gaseous SO2 or CO2 to form an aqueous SO2 solution or a CO2 solution, or to form sulfurous acid or carbonic acid.

[0095] As shown above, the use of an extruder is a key element of the advantages of the described process and is highly advantageous for the process of producing either the compound of formula (I) or the compound of formula (IV), respectively.

[0096] Therefore, in further embodiments, the present invention relates to formula (I) or (IV) [ka] (In the formula, R is either H or CH3, preferably CH3, and X is either Na or K, preferably Na) This relates to the use of an extruder 1 in the production of a compound.

[0097] Preferred embodiments of the compounds of formulas (I) and IV have already been described in detail above.

[0098] The present invention and certain preferred embodiments thereof will be described in more detail below. It is emphasized that only the elements necessary for understanding will be shown. The same elements are indicated by the same reference numerals in different figures. Furthermore, it is emphasized that the figures are schematic and not related in particular to actual size and proportions. [Brief explanation of the drawing]

[0099] [Figure 1] A schematic diagram of a typical extruder 1 suitable for the process of the present invention is shown. The compound of formula (II) is introduced through the inlet 2 of the extruder 1, and a melting and reaction step b) is carried out at a temperature above the melting point of XOH, particularly 320°C to 450°C, more particularly 330°C to 450°C, even more particularly 360°C to 450°C, preferably 360°C to 420°C, more preferably 380°C to 400°C, in order to obtain the compound of formula (I), and the compound of formula (I) exits the extruder 1 through the outlet 3 of the extruder. The base XOH can be supplied to the extruder by separate inlets (inlet 4 for KOH and / or NaOH), or it can be supplied directly to the extruder together with the compound of formula (II) through inlet 2. In the latter case, a premixture of XOH and the compound of formula (II) is formed before entering the extruder. It is preferable that XOH, particularly NaOH, be introduced to the extruder 1 as a molten product. [Figure 2]Further details of Figure 1 are schematically shown in a cross-sectional view of an embodiment having separate inlets for XOH. The extruder 1 includes a cavity 5 surrounded by a casing 6. Inside the cavity 5 is the extruder screw 7. Formula (II) or XOH is introduced into the extruder cavity 5 through inlet 2 and inlet 4 for KOH and / or NaOH. XOH, preferably NaOH in particular, is preferably introduced into the extruder 1 as a molten material. The screw 7 is rotated around its longitudinal axis by a motor 8 (indicated by arrow A). The rotational action of the screw 7 completely mixes the compound of formula (II) and XOH and transports them along the axis from the inlet to the outlet of the extruder (indicated by arrow B). A heating element 9 located inside or on the surface of the casing 6 ensures that the compound of formula (II) and XOH reach a temperature above the melting point of XOH, particularly 320°C to 450°C, more particularly 330°C to 450°C, even more particularly 360°C to 450°C, preferably 360°C to 420°C, and more preferably 380°C to 400°C, thereby enabling the reaction to occur, forming the compound of formula (I) in the extruder, which exits the extruder through the extruder outlet 3. Preferably, the reaction mixture is heated in such a way that a temperature gradient is obtained between the compound of formula (II) and XOH, such that the reaction mixture in the compartments near inlets 2 and 4 is at a lower temperature than the reaction mixture in the compartment near outlet 3. Preferably, the extruder is provided with at least one degassing outlet 10 to allow gas to escape from the cavity in order to reduce the pressure accumulated by the gas formed during the reaction. The degassing outlet preferably has a pressure control valve 11. [Figure 3]In step a0), a first extruder 1a neutralizes the compound of formula (II), particularly formula (II-A), and a second extruder 1b carries out reaction step b) to obtain the compound of formula (I). The compound of formula (II), particularly formula (II-A), is introduced into the first extruder 1a through inlet 2a, and the base XOH, particularly NaOH, is introduced into the first extruder 1a through inlet 4, preferably in the form of pearls or pellets of several millimeters, as commercially available. In the first extruder 1a, a neutralization reaction is carried out at a temperature of 100°C to 200°C, particularly 100°C to 180°C, more particularly 100°C to 150°C, preferably 110°C to 130°C to form the compound of formula (II-B), and the compound of formula (II-B) exits the first extruder 1a through outlet 3a. The compound of formula (II-B) is transferred from the outlet 3a of the first extruder to the inlet of the second extruder 1b by a connecting means 12, such as a tube, which is closed to the environment. Preferably, the base XOH, particularly NaOH, as a molten product is transferred to the second extruder 1b by the inlet 4, and reaction step b) takes place at a temperature above the melting point of XOH, particularly 320°C to 450°C, more particularly 330°C to 450°C, even more particularly 360°C to 450°C, preferably 360°C to 420°C, more preferably 380°C to 400°C, in order to obtain the compound of formula (I), and the compound of formula (I) exits the second extruder through the outlet 3b of the second extruder. Furthermore, Figure 3 shows that the compound of formula (I) is transferred from the outlet 3b of the second extruder to a container 13 containing water by a connecting means 12, such as a tube, which is closed to the environment. The compound of formula (I) can be isolated from the container 13 containing water. In Figure 3, the extruders preferably include a degassing outlet 10, which includes a pressure control valve, to allow gas, particularly water vapor, to escape from the first extruder 1a and the second extruder 1b. [Figure 4]Further details of a preferred embodiment, including a first extruder 1a and a second extruder 1b, are schematically shown in a cross-sectional view. Extruder 1a includes a cavity 5 surrounded by a casing 6. Inside the cavity 5 is the screw 7 of the first extruder. Compound (II-A), particularly (II-A2), or XOH is preferably introduced into the cavity 5 of the first extruder by a pump 15 through inlet 2a and inlet 4 for KOH and / or NaOH. XOH, preferably particularly NaOH, is preferably introduced into the first extruder 1 in the form of pearls or pellets several millimeters in size, as commercially available. The screw 7 is rotated around its longitudinal axis by a motor 8 (indicated by arrow A). The rotational action of the screw 7 completely mixes the compound of formula (II-A) and XOH and transports them along the axis from the inlet to the outlet of the extruder (indicated by arrow B). To perform the neutralization step a0), that is, to form the compound of formula (II-b), a heating element 9 located inside or on the surface of the casing 6 ensures that the compound of formula (II-A) and XOH are at a temperature of 100°C to 200°C, particularly 100°C to 180°C, more particularly 100°C to 150°C, preferably 110°C to 130°C. The mixture of the compound of formula (II-A) and XOH is preferably heated in such a way that a temperature gradient is obtained such that the mixture in the compartments near inlets 2a, 4 is at a lower temperature than the mixture in the compartment near outlet 3a. The compound of formula (II-B) exits the first extruder through outlet 3a and is transferred to the inlet 2b of the second extruder 1b by a connecting means 12, such as a tube, which is closed to the environment. In this figure, this transfer is assisted by a pump 15. The second extruder 1b includes a cavity 5 surrounded by the casing 6. Inside cavity 5 is the screw 7 of the second extruder. The compound of formula (II-B) or XOH is preferably introduced into cavity 5 of the second extruder by pump 15 through inlet 2b and inlet 4 for KOH and / or NaOH. XOH, preferably NaOH in particular, is preferably introduced into the second extruder 1 as a molten material. The screw 7 is rotated around its longitudinal axis by motor 8 (indicated by arrow A).The rotational action of the screw 7 completely mixes the compound of formula (II-B) and XOH, and the mixture is transported along the axis from the inlet to the outlet of the extruder (indicated by arrow B). To obtain the compound of formula (I) by carrying out reaction step b), a heating element 9 located inside or on the surface of the casing 6 ensures that the compound of formula (II-B) and XOH reach a temperature above the melting point of XOH, particularly 320°C to 450°C, more particularly 330°C to 450°C, even more particularly 360°C to 450°C, preferably 360°C to 420°C, and more preferably 380°C to 400°C. The mixture of the compound of formula (II-B) and XOH is preferably heated in such a way that a temperature gradient is obtained such that the mixture in the compartments near inlets 3a and 4 is at a lower temperature than the mixture in the compartment near outlet 3a. The compound of formula (I) exits the second extruder 1b through the outlet 3b of the second extruder and is transferred to a container 13 containing water by a connecting means 12, such as a tube, which is closed to the environment. In this embodiment, all connecting means 12 and pump 15 are preferably heated to prevent the substance inside the connecting means from cooling and solidifying. In this figure, this transfer is shown to be assisted by the pump 15. Adding the compound of formula (I) to the water in the container 13 is preferably done by stirring using a stirring means 14, such as a paddle-type stirring rod. By adding the molten mixture of the compound of formula (I) and residual XOH to the water in the container 13, the compound of formula (I) is cooled to a temperature of less than 100°C, particularly less than 60°C, preferably less than 40°C. This action causes the compound of formula (I) to form solid particles (not shown in Figure 4), while other reaction products remain in solution. Thus, the solid particles of the compound of formula (I) can be easily separated, for example, by filtration (not shown in Figure 4). In Figure 4, the extruders preferably include a degassing outlet 10, which includes a pressure control valve 11, so that gas, particularly water vapor, can be released from the first extruder 1a and the second extruder 1b.

[0100] [List of reference symbols] 1 extruder 6 casings 1a First extruder 7 Extruder screw 1b Second extruder 8 Motor for rotating screw 7 2 Extruder inlet 9 Heating element 2a Inlet of the first extruder 1a 10 Degassing outlet 2b Inlet of second extruder 1b 11 Pressure control valve 3 Extruder outlet 12 Connection means 3a Outlet of the first extruder 1a 13 Container containing water 3b Second outlet of first extruder 1b 14 Agitation means 4 KOH and / or NaOH inlet 15 Pump 5 Cavity

[0101] [Examples] The present invention will be further explained by the following experiment.

[0102] In the following experiments, a laboratory extruder will be used (corresponding to Figure 2, except that it will be supplied as a premix; see below).

[0103] The extruder uses three screws arranged in a parallel line (length (L) = 2504 mm, outer diameter (D) = 52 mm, L / D = 48, screw speed (N) = as shown in Table 1). A premixture of solid sodium hydroxide and solid sodium 2,5-dimethylbenzenesulfonate (40 / 60 (weight / weight)) was introduced by a screw pump from a closed funnel at the inlet of the triscrew extruder at the feed rate (Q) shown in Table 1. The extruder barrel was heated by 12 individual heating elements (210 mm) arranged along the extruder. Each element was individually heated to obtain a specific temperature (°C) to create the following temperature gradient from the inlet (left) to the outlet (right).

[0104] [Table 1]

[0105] Neutralization (step a0) is performed in the first region, and melting and reaction (step b) are performed in the subsequent region. The last third of the extruder is provided with a degassing outlet with a pressure control valve.

[0106] Different dwell times (t r Different feed rates were tested to produce the reaction product. The conversion rate (C) to sodium 2,5-dimethylphenolate (sodium p-xylenolate) was determined by analyzing the reaction product exiting the extruder at the extruder outlet by GC-MS and HPLC.

[0107] [Table 2]

Claims

1. Equation (I) 【Chemistry 1】 The compound of formula (II) 【Chemistry 2】 A process for producing from the compound, a) A step of providing the compound of formula (II), b) A step of melting and reacting the compound of formula (II) with XOH in an extruder (1) at a temperature above the melting point of XOH, particularly 320°C to 450°C, more particularly 330°C to 450°C, even more particularly 360°C to 450°C, preferably 360°C to 420°C, and more preferably 380°C to 400°C, to obtain the compound of formula (I). In a process including, R is H or CH ３ It is either SO ３ H, or SO ３ － X ＋ A process characterized in that , or Cl, and X is either Na or K, preferably Na.

2. R = CH ３ The process according to claim 1, characterized in that it is the process described above.

3. Y = SO ３ － X ＋ 、 especially SO ３ － Na ＋ The process according to claim 1 or 2, characterized in that it is

4. The compound of formula (II) is the compound of formula (II-B), in step a0. a0) A step of neutralizing the compound of formula (II-A) with XOH in an extruder at a temperature of 100°C to 200°C, particularly 100°C to 180°C, more particularly 100°C to 150°C, preferably 110°C to 130°C, to form the compound of formula (II-B). 【Transformation 3】 The process according to claim 3, characterized in that the compound is of formula (II-B) and prepared by the method described above.

5. The process according to claim 4, characterized in that the neutralization step a0) is carried out in a first extruder (1a), the melting reaction step b) is carried out in a second extruder (1b), and the compound of formula (II) is transferred from the outlet (3a) of the first extruder (1a) to the inlet (2b) of the second extruder (1b).

6. The process according to claim 4 or 5, characterized in that step a0) of neutralizing the compound of formula (II) with sodium hydroxide and / or potassium hydroxide is carried out in the presence of a molar excess of XOH such that the molar ratio of XOH to the compound of formula (II) is > 1, particularly 1 to 2, preferably 1 to 1.5, and more preferably 1 to 1.

25.

7. The process according to any one of claims 4 to 6, characterized in that the transfer of material between the first extruder (1a) and the second extruder (1b) is carried out by a connecting means (12) that is closed off from the environment.

8. The compound of formula (II-A) is of formula (III) 【Chemistry 4】 (In the formula, R is H or CH) ３ Either of the following, preferably CH ３ (is) The compound and sulfuric acid (H ２ SO ４ The process according to any one of claims 4 to 7, characterized by being obtained by reaction with ).

9. The process according to any one of claims 1 to 8, characterized in that step b) of melting and reacting the compound of formula (II) with XOH is carried out in the presence of a molar excess of XOH such that the molar ratio of XOH to and / or thereafter to the compound of formula (II) is > 2, particularly 2 to 4, preferably 2 to 3, more preferably 2 to 2.

5.

10. The process according to any one of claims 1 to 9, characterized in that the temperature of the material in the region of the inlet (2) of the extruder (1) is lower than that in the region of the outlet (3) of the extruder (1).

11. The process according to any one of claims 1 to 10, characterized in that the extruder (1) includes at least one degassing outlet (10).

12. The process according to any one of claims 1 to 11, characterized in that XOH is transferred to the extruder in the form of solid XOH or molten XOH.

13. The process according to any one of claims 1 to 12, characterized in that it is a continuous process.

14. The process according to any one of claims 1 to 13, characterized in that the extruder (1) is a twin-screw or triple-screw extruder.

15. The compound of formula (I), after step b), is added to a container (13) containing water, particularly an aqueous sulfite solution, preferably Na, along with excess molten XOH. ２ SO ３ The process according to any one of claims 1 to 14, characterized in that the substance is transferred to an aqueous solution.

16. Formula (IV) 【Transformation 5】 In the process of producing the compound, i) The process according to any one of claims 1 to 15, the formula (I) 【Transformation 6】 The process of preparing the compound, followed by, c) A step of acidifying the compound of formula (I) with an acid to obtain the compound of formula (IV). It includes, and R is H or CH ３ Either of the following, preferably CH ３ A process characterized by being...

17. Formula (I) or (IV) 【Transformation 7】 (In the formula, R is H or CH) ３ Either of the following, preferably CH ３ (wherein X is either Na or K, preferably Na) Use of an extruder (1) in the production of the compound.

18. An extruder (1) for producing a compound of formula (I), wherein at least, - Casing (6), - The cavity (5) inside the casing (6), - Extruder screw (7) inside the cavity (5), - Entrance (2) for the compound of formula (II), - Outlet (3) for the compound of formula (I), - A mixture of XOH and the compound of formula (II) inside the cavity (5). 【Transformation 8】 In an extruder (1) including, R is H or CH ３ It is either SO ３ H, or SO ３ － X ＋ An extruder (1) characterized in that , or Cl, and X is either Na or K, preferably Na.

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