Method and apparatus for drying and / or purifying nitrate esters

Abstract

The invention relates to a method for drying and / or cleaning, preferably drying and cleaning aliphatic or cycloaliphatic nitrate esters (nitrate esters), in particular for removing water and volatile and / or volatilizable impurities, in particular generated during the production and / or washing of nitrate esters, the invention also relates to a corresponding use and to a corresponding device and system for carrying out the method.

Description

Technical Field

[0001] This invention relates to the field of production, and particularly drying and / or purification, of aliphatic and alicyclic nitrates (nitrates), with the aim of providing dried and / or anhydrous and pure nitrates.

[0002] In particular, the present invention relates to a method for drying and / or purifying aliphatic or alicyclic nitrates (nitrates), especially for removing water and volatile impurities particularly generated during the production and / or washing of nitrates.

[0003] Furthermore, the present invention also relates to an apparatus for drying and / or purifying aliphatic or alicyclic nitrates (nitrates), and a production apparatus for producing aliphatic or alicyclic nitrates (nitrates).

[0004] Finally, the present invention relates to the use of inert gases for drying and / or purifying, preferably drying and purifying, crude aliphatic or cyclic aliphatic nitrates (nitrates) obtained from production processes. Background Technology

[0005] Aliphatic and / or alicyclic organic nitrate esters (nitrate esters) are the reaction products of the corresponding aliphatic and / or alicyclic alcohols with nitric acid. Nitrate esters are typically produced in continuously operating units by reacting the alcohol directly with nitric acid, or by reacting it in the presence of sulfuric acid as a catalyst and water binder (e.g., using the syringe process according to the Schmid-Meissner or Biazzi method, or the Nielsen and Brunnberg NAB process, or a modified method according to EP1792891A1). The nitration of alcohols (i.e., their conversion to nitrate esters) usually occurs in the liquid phase, in the form of pure substances or mixtures, or may also be carried out in solutions of inert, water-immiscible solvents.

[0006] Organic nitrates are particularly common in the field of explosives chemistry (e.g., nitroglycerin, ethylene glycol dinitrate, etc.), as well as in the pharmaceutical industry (e.g., sterol nitrates, etc.) and the fuel industry, especially as additives. For example, one known and widely used additive in the fuel industry is ethylhexyl nitrate (EHN), which is used as an additive in diesel fuel to increase the cetane number. Other widely used nitrates include pentaerythritol tetranitrate (PETN), glyceryl trinitrate (NGL), and ethylene glycol dinitrate (EGDN).

[0007] The cetane number is a numerical value that describes the flammability of diesel fuel: the higher the cetane number, the more flammable the fuel. In this case, it is first determined that the higher the proportion of straight-chain hydrocarbon molecules in the fuel, the better its auto-ignition properties, which is an ideal characteristic, especially in diesel engines.

[0008] Using fuels with lower cetane numbers often makes compression-ignition engines (diesel engines) more difficult to start and noisier when cold. Conversely, fuels with higher cetane numbers tend to result in easier cold starts, lower engine noise, and less white smoke (“cold smoke”) produced by incomplete combustion.

[0009] Therefore, there is a general preference for diesel fuels with high cetane numbers, a preference that has become increasingly pronounced due to increasingly stringent emission regulations, as vehicle diesel fuel specifications typically specify a minimum cetane number. Accordingly, many diesel fuel compositions contain additives in the form of ignition improvers, also known as cetane enhancers or cetane (number) improvers, to ensure compliance with these specifications and generally improve fuel combustion performance.

[0010] The most commonly used ignition improver for diesel fuels is probably 2-ethylhexyl nitrate (EHN). It is particularly effective at shortening the ignition delay of fuels for which this additive has been added.

[0011] The crude nitrate esters obtained from the aforementioned production process must undergo washing (especially multi-stage washing) and additional purification steps before being used, for example, as ignition modifiers and / or for further processing in this regard. This is necessary to remove dissolved or suspended impurities (such as sulfuric acid, nitric acid, nitrite, etc.) and byproducts of the oxidation and degradation of the raw material alcohols. In this way, the stability of the nitrate esters, which are the main components of highly sensitive explosives, can be improved.

[0012] Generally, washing crude nitrate esters to remove acids dissolved and suspended therein from the nitration mixture, as well as other impurities that are acidic or can be extracted with detergents, involves three steps: acid washing, alkaline washing, and neutral washing (see, for example, T. Urbanski, Vol. 2, pp. 97 and thereafter, particularly Figures 43, 44, 59, and 60, Pergamon Press, 1985 reprint). However, washing crude nitrate esters directly with, for example, a sodium carbonate solution, omitting the "acid washing" stage, is also practiced to some extent and is part of the prior art. Water is typically used as the washing medium. Washing is usually carried out in a liquid-liquid manner, using nitrate esters that are typically liquid at the washing temperature, or using a solution of nitrate esters in a suitable solvent.

[0013] When washing crude nitrate esters using the liquid-liquid extraction method, only impurities with high solubility in the washing medium (such as sulfuric acid and nitric acid), or those disproportionate to water and thus forming nitric acid in an aqueous medium, or those that form salts with the added alkali during alkaline washing, such as strong acids, especially sulfuric acid and nitric acid, as well as moderately strong and weak acids, such as nitrophenol, nitrocresol, nitrobenzoic acid, nitrous acid, acetic acid, oxalic acid, formic acid, carbonic acid, and hydrogen cyanide, can be washed away. However, even for these impurities, their removal during the washing process is not always complete or quantitative, especially when the crude nitrate ester has a high content of these impurities.

[0014] It was also found that other impurities, especially those with unfavorable partition coefficients relative to the washing medium, or those that are weakly acidic or lack acidity, or those that convert to such substances that are insoluble in the organic phase at a slow conversion rate, often cannot be completely removed in one or more steps during washing and / or during the washing process, and / or can only be removed with great technical effort.

[0015] High water content (regardless of uniformity) in nitrate esters obtained through washing is generally undesirable, as it negatively impacts the performance of the nitrate ester product. This is particularly evident in the specification data for nitrate esters; the standard specification for water content in ethylhexyl nitrate is typically set at a maximum of 0.05%, as otherwise the product will exhibit a persistent turbidity. Furthermore, even small amounts of residual water or moisture are difficult to remove from nitrate esters.

[0016] In this regard, methods specifically involving the drying of nitrate esters have been disclosed in the prior art.

[0017] For example, Chinese patent application CN1903829A describes a method for producing and drying isooctyl nitrate. The drying method in this case includes the following steps: first, separating crude isooctyl nitrate from water by sedimentation and phase separation; subsequently, drying the resulting isooctyl nitrate, still containing a small amount of water, through a series of layers and / or trays of anhydrous sodium sulfate. The disadvantages of this method are that the sodium sulfate needs to be periodically regenerated in a complex manner by heat treatment, and / or completely replaced if necessary. Furthermore, sodium sulfate can only remove water from isooctyl nitrate and cannot reduce other volatile and / or volatile impurities. In addition, the drying performance of sodium sulfate is not high enough to achieve very low water content in the final product. Moreover, the method must be carried out in two stages in separate equipment for separate process stages, which requires considerable effort. The method is also relatively costly and time-consuming.

[0018] Chinese patent application CN1031525A describes a method for producing isooctyl nitrate, in which the product is dried in a vacuum. This method removes volatile and / or easily volatile impurities; however, vacuum drying is very complex in terms of equipment and energy, and often does not allow for the drying of large quantities of product. Furthermore, it is particularly difficult to easily remove small amounts of water. In addition, vacuum drying often results in considerable product loss.

[0019] Finally, Chinese patent CN101696168B describes a method for producing isooctyl nitrate, wherein the resulting product is dried in such a manner that it passes through a silica gel column and / or molecular sieve. The silica gel and / or molecular sieve absorb impurities and / or water from the isooctyl nitrate. However, a disadvantage of this method is that the column material must be regenerated and / or replaced periodically, which is complex, excessively time-consuming, costly, and labor-intensive, especially for large-scale production. Furthermore, the regeneration of the column material typically requires high temperatures, which can lead to fire and / or explosion risks, especially in the presence of residual nitrate. Therefore, this method is also unsuitable for industrial-scale production.

[0020] Therefore, especially for large-scale production, existing methods for drying nitrate esters are complex, time-consuming, costly, and labor-intensive, often failing to achieve the desired results. Furthermore, these existing methods cannot remove volatile impurities.

[0021] Therefore, in general, there is still a need to develop production methods for organic nitrates (preferably aliphatic and alicyclic nitrates), especially purification and drying methods, in the existing technology. These methods are designed to be efficient in terms of achievable drying performance, while requiring minimal equipment expenditure and minimal effort in process execution and / or control. Summary of the Invention

[0022] Therefore, in light of the above-mentioned prior art, the object of the present invention is to provide a method and corresponding equipment and / or (production) apparatus for drying and / or purifying aliphatic or alicyclic organic nitrates, wherein the aforementioned disadvantages of known methods and / or known equipment and (production) apparatus in the prior art are avoided or at least mitigated.

[0023] Specifically, the object of the present invention is to provide a method and corresponding equipment and / or (production) apparatus for drying and / or purifying aliphatic or alicyclic organic nitrates, wherein the method and / or corresponding equipment and (production) apparatus are designed to be more efficient in achieving drying and / or purification compared with known prior art, and can be performed and / or operated with less effort in terms of process execution and equipment.

[0024] In a completely unexpected manner, the applicant has now discovered that, based on the inventive concept upon which this invention is based, particularly by means of the method and / or corresponding equipment and / or (production) apparatus for drying and / or purifying (preferably drying and purifying) aliphatic or alicyclic nitrates (nitrates) according to the invention, a highly efficient and resource-saving nitrate processing concept can be provided, which can also provide purified and / or pure nitrates with significantly better dryness and / or purity than those of the prior art, and in particular, can remove water present in the washed crude nitrates (i.e., the washed crude nitrates are dried), while simultaneously or in the same manner removing volatile and / or volatile impurities, particularly generated during the nitrate production process.

[0025] To address the aforementioned problems, according to a first aspect of the invention, the present invention therefore provides a method for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrates (nitrate esters) according to claim 1, particularly for removing water and volatile impurities generated especially during the production and / or washing of nitrate esters. In each case, advantageous modifications and embodiments of this aspect of the invention are the subject of the corresponding independent claims and / or dependent claims (sub-claims).

[0026] According to a second aspect of the invention, another subject matter is an apparatus for drying and / or purifying, preferably for drying and purifying aliphatic or alicyclic nitrates (nitrates), particularly for removing water and volatile impurities generated especially during the production and / or washing of nitrates, preferably by contact with an inert gas, particularly by flow (permeation), and especially for carrying out the method of the invention according to the respective independent claims. In each case, advantageous modifications and embodiments of this aspect of the invention are the subject matter of the respective independent claims and / or dependent claims (sub-claims).

[0027] Furthermore, according to a third aspect of the invention, the subject matter of the invention is an apparatus for producing aliphatic or alicyclic nitrates (nitrates) according to the respective independent claims. In each case, advantageous modifications and embodiments of this aspect of the invention are the subject matter of the respective dependent claims (sub-claims).

[0028] Finally, according to a fourth aspect of the invention, the subject matter of the invention is its use according to the respective independent claims. In each case, advantageous modifications and embodiments of this aspect of the invention are the subject matter of the respective dependent claims (sub-claims).

[0029] It goes without saying that the improvements, implementation methods, advantages, etc. listed below are only for the purpose of avoiding repetition and are applicable to only one aspect of the present invention. Of course, they are also applicable to other aspects of the present invention and do not need to be explained separately.

[0030] Furthermore, it is self-evident that the numerical values, figures, and ranges described below should not be interpreted in a restrictive manner; it is also self-evident to those skilled in the art that deviations from the ranges or descriptions may be made depending on the specific circumstances or application without departing from the scope of the invention.

[0031] Furthermore, it applies that, in principle, all numerical values ​​and / or parameter descriptions mentioned below can be determined or measured by normalization and / or standardization or explicitly stated measurement methods, or by measurement methods familiar to those skilled in the art.

[0032] Furthermore, regarding all relative and / or percentage (especially weight-related percentages) quantities mentioned below, it should be noted that those skilled in the art should select and / or combine these expressions in such a manner, according to the reference system used (e.g., dosage form), to ensure that the total amount is always 100% and / or 100 wt%—potentially including other ingredients and / or formulations and / or additives and / or components, especially those defined below. However, this is self-evident to those skilled in the art.

[0033] Furthermore, it is applicable to the description of this invention that features of the invention, when referenced in conjunction with specific improvements, embodiments, advantages, examples, etc., should also be considered as disclosed in combination thereof. Therefore, in this case, higher-level combinations of single or multiple features referenced in corresponding improvements, embodiments, application examples, etc., should also be considered as disclosed.

[0034] In particular, it is applicable to characterize the features of the present invention that all possible combinations of these features should be considered as disclosed, and that implementations of comparable and / or corresponding preferred features are preferred in combination of them (e.g., the number and / or range of the same preferred related parameters, etc.).

[0035] In this context, it is particularly applicable that, for statements cited below relating to the same preferences and / or the same degree of preference for different parameters, etc., as with the method of the present invention, corresponding combinations involving different parameters with corresponding preferences and / or optima are also disclosed. Similarly, all other combinations (i.e., combinations based on different preferences and / or different degrees of preference) are also disclosed.

[0036] Nevertheless, the present invention will be described in detail below: According to a first aspect of the invention, the subject matter of the invention is a method for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrates (nitrates), particularly for removing water and volatile impurities specifically generated during the production and / or washing of nitrates. This method includes the following steps: (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. (b) Subsequently, the washed crude nitrate ester obtained in step (a) is dried and / or purified, preferably dried and purified, by contacting it with an inert gas, particularly by permeation, in particular to remove water present in the washed crude nitrate ester (i.e. dried washed crude nitrate ester), while and / or in the same manner to remove volatile impurities generated particularly during the production and / or washing of the nitrate ester.

[0037] Within the scope of this invention, a particularly efficient, especially resource-saving and highly effective method is provided for drying and / or purifying, particularly drying and purifying, aliphatic or alicyclic organic nitrates (nitrates).

[0038] The high efficiency of the method of the present invention is particularly evident in its ability to provide exceptionally high quality purified or dried nitrate esters, especially those nitrate esters characterized by very high purity and extremely low proportions of moisture and / or water remaining in the nitrate esters after the execution of the method according to the invention. This characteristic of the nitrate esters having exceptionally high purity and being as free of moisture and / or water as possible is directly attributed to the steps of the method according to the invention, particularly step (b), which involves drying and / or purifying the nitrate esters by contacting them with an inert gas, especially by a flow path.

[0039] Within the scope of this invention, purification means the complete removal (i.e., at least substantially complete removal or reduction to the minimum required amount, preferably complete removal) of specific volatile impurities or foreign substances from crude nitrates obtained during the production process and which have undergone a washing step. As a result of purification, purified nitrates are obtained, i.e., nitrates free of and / or with foreign substances or impurities removed, which in this respect can be considered pure nitrates. Therefore, the result or objective of purification within the scope of this invention is particularly to reduce the proportion of volatile impurities in nitrates, preferably to a proportion of volatile impurities, particularly in the low ppm range.

[0040] Therefore, it is advantageous within the scope of this invention to achieve particularly low levels or proportions of specific volatile impurities in purified nitrate esters, which is impossible to achieve using methods known in the prior art, or can only be achieved with extremely high and correspondingly impractical effort.

[0041] The high purity of nitrate esters achievable by the method of this invention is directly attributed to the specific process within the scope of this invention. Specifically, within the scope of this invention, pure nitrate esters can be obtained in such a manner that they can be considered substantially free of, in particular, volatile impurities, especially since pure nitrate esters can be produced, particularly where the proportion of volatile impurities is in the range of at most 100 ppm, preferably at most 30 ppm, and most preferably at most 10 ppm. This is generally impossible in known methods in the prior art.

[0042] Therefore, in particular, compared with existing nitrate ester purification methods, the method based on the present invention can obtain nitrate esters that are substantially free of and / or free of specific volatile impurities within the scope of the present invention.

[0043] Furthermore, the drying in conjunction with the method of the present invention should be understood to mean: removing residual trace amounts of moisture and / or water, especially from the washing medium in the washed nitrate ester, as much as possible or at least substantially completely from the nitrate ester obtained by the method of the present invention.

[0044] Advantageously, within the scope of this invention, the proportion of moisture and / or water in purified and / or dried nitrate esters can be reduced to a level and / or proportion that is unattainable or achievable only through considerable and therefore impractical effort by conventional methods and / or methods known in the prior art.

[0045] Therefore, within the scope of this invention, and particularly due to the method and steps of this invention, at least substantially completely dry and / or fully dried nitrate esters can be obtained, i.e., nitrate esters free from and / or without moisture and / or water, for example, from the washing medium, which contrasts with known nitrate ester drying methods in the prior art. In particular, within the scope of this invention, substantially dry and / or fully dried purified and / or dried nitrate esters, and substantially completely free from and / or without moisture or water, refer to purified and / or dried nitrate esters with a water content, particularly in the range of 0.025 wt% or less.

[0046] Furthermore, within the scope of this invention, volatility and / or volatile impurities should be understood to mean substances and / or substances or compounds that are volatile and / or exhibit volatile behavior, particularly under specific process conditions. Volatility is a property of a substance, specifically describing the tendency to evaporate and / or evaporate (i.e., the tendency of a substance to change from a liquid to a gaseous state without reaching its boiling point temperature). In particular, the physical (distribution) equilibrium between the gas and liquid phases, as well as the partial pressure and / or vapor pressure of the relevant substance and / or substance or compound, may also play a role and / or be taken into consideration in this regard.

[0047] Evaporation occurs when the gas phase above and / or around a liquid is not yet saturated with vapor. The volatility of a substance can be defined, in particular, by its vapor pressure, and / or, within the scope of this invention, by comparison with the vapor pressure of a reference substance.

[0048] Within the scope of this invention, the term "volatile compound" also includes compounds that become and / or become volatile under process conditions, i.e., compounds that are volatile and / or become volatile under specific process conditions, regardless of their volatility under pure and / or isolated standard conditions. This can be explained in particular by providing, within the scope of this invention, the washing and / or removal of volatile impurities from nitrate esters (particularly by contacting them with an inert gas). These process conditions involve a gas phase (inert gas) saturated with a liquid, which is maintained continuously and / or constantly at a relatively low level, resulting in an increased tendency for substances to volatilize under the process conditions of this invention.

[0049] An essential advantage of the present invention, and especially the method described herein, is that purified and / or dried nitrate esters can be obtained, characterized in that these nitrate esters have significantly improved quality in terms of purity and / or dryness and / or absence of moisture and / or water compared to the dryness or purity achievable to date.

[0050] In particular, the method of the present invention can provide purified and / or pure nitrate esters having a particularly low proportion of volatile impurities in the range of very low ppm, particularly at most 100 ppm, preferably at most 30 ppm, and especially preferably at most 10 ppm. This, however, has so far been achieved with extremely high, uneconomical effort and / or ultimately particularly inefficient methods in the prior art.

[0051] The method of the present invention can also advantageously provide dried and / or dry nitrates with extremely low water and / or moisture content, and thus, within the scope of the present invention, at least substantially moisture-free and / or anhydrous nitrates can be provided.

[0052] In particular, the method of the present invention can dry nitrates to such an extent that, based on the dried and / or purified nitrates, the moisture and / or water content is in the range of up to 0.06 wt%, preferably up to 0.01 wt%.

[0053] Within the scope of this invention, it is particularly advantageous to achieve a cloud point below 0°C for dried and / or dry nitrate esters, which corresponds to a residual moisture and / or moisture and / or water content in the nitrate ester being less than 0.02 wt%. Nitrates with such specifications are characterized by significantly improved performance, for example, when used as ignition modifiers in fuel mixtures. This particularly improves the ignition performance of the corresponding fuel mixtures at low temperatures (e.g., in the range of 0°C or lower).

[0054] The high efficiency of the method of the present invention is particularly advantageous in that, within the scope of the invention, especially within the scope of the method of the invention, and specifically due to the particular procedure of the method of the invention, the drying and / or purification of crude nitrate ester previously washed with a washing medium within the scope of the washing step can be performed in a non-complicated manner on equipment by contacting the washed crude nitrate ester with an inert gas, particularly by allowing the inert gas to flow through (permeate) the washed crude nitrate ester. The contact and / or particularly the flow (permeation) of the crude nitrate ester with the inert gas makes it possible to purify and / or dry the crude nitrate ester using very few additives and / or process components. This advantageously produces a highly economical method that remains rigorous in terms of complexity and reduces the process components and / or media used in the method according to the invention. This economical, rigorous procedure and / or process layout also has a direct advantageous impact on the process technology and / or equipment, as it enables the use of equipment and production apparatus that are simplified in terms of structural complexity compared to prior art equipment and / or apparatus for drying and / or purifying nitrate esters, thereby advantageously achieving improved process safety and process continuity while improving product quality.

[0055] Since the method of the present invention requires only a very small amount of process components and / or media (the washing medium in step (a) and the inert gas as the drying and / or purifying medium in step (b)), it can also be operated in a resource-saving manner.

[0056] According to another particular advantage of the invention, the steps of the invention also allow for the recovery and / or recycling of the inert gas used in the drying and / or purification step (b). Therefore, it is advantageous within the scope of the invention to reuse the inert gas in the method of the invention, particularly in step (b), after the inert gas has passed through and / or contacted the nitrates to be purified. For this purpose, intermediate drying of the inert gas has proven advantageous, as this can be incorporated into the concept of the invention in a simple manner in terms of equipment and in a rigorous manner in terms of process technology.

[0057] Therefore, it is advantageous within the scope of this invention that the inert gas, which has absorbed moisture and / or water from the previously washed crude nitrate to be purified and / or dried, can be dried in a downstream drying step and regenerated in a manner that allows and / or may recycle and / or reuse the inert gas, thereby enabling operation in a particularly resource-efficient manner within the scope of this invention. It is also advantageous within the scope of the method and / or the scope of this invention that the moisture and / or water separated from the inert gas can be returned to the process, particularly to the washing medium in the washing step, resulting in economical and environmentally friendly high efficiency in the washing medium for cleaning the crude nitrate obtained from the production process.

[0058] Therefore, especially within the scope of the method of the present invention, the present invention not only provides the possibility of obtaining particularly high quality nitrates (characterized in particular by extremely high purity and dryness), but also provides the possibility of working in a relatively resource-saving and environmentally friendly manner.

[0059] Since the method of the present invention can be implemented with relatively low investment in equipment and / or with economical and rigorous equipment and / or production facilities in terms of process technology, the present invention is characterized by high efficiency, which is particularly evident in the ease of operation of the method of the present invention. At the same time, the method of the present invention is also highly efficient in terms of the high purity and dryness of the products obtained by the method.

[0060] Specifically, the present invention provides a method for purifying and drying organic nitrates (preferably aliphatic and alicyclic nitrates) that is efficiently designed in terms of achievable drying performance while minimizing effort in equipment and process management and / or control.

[0061] Furthermore, within the scope of this invention, a method and corresponding equipment and / or (production) apparatus for drying and / or purifying aliphatic or alicyclic organic nitrates can be provided, wherein the aforementioned disadvantages of known methods and / or known equipment and (production) apparatus of the prior art can be avoided or at least mitigated.

[0062] Specifically, within the scope of this invention, a method and corresponding equipment and / or (production) apparatus for drying and / or purifying aliphatic or alicyclic organic nitrates can be provided, wherein the method and / or corresponding equipment and (production) apparatus are designed to be more efficient in achieving drying and / or purification, and are easier to perform and / or operate in terms of process management and equipment, compared with known prior art.

[0063] As described above, in order to solve the aforementioned problems, a method is hereby provided for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrate esters (nitrate esters), particularly for removing water and volatile impurities generated especially during the production and / or washing process of nitrate esters. This method includes the following steps: (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. (b) Subsequently, the washed crude nitrate obtained in step (a) is dried and / or purified, particularly by contact with an inert gas, particularly by flow (permeation), in such a way that water present in the washed crude nitrate is removed (i.e. the washed crude nitrate is dried), while and / or volatile impurities generated particularly during the production and / or washing of the nitrate are removed in the same manner.

[0064] Regarding the preferred use and / or reaction of nitrate esters within the scope of this invention, it has been proven useful in this regard that nitrate esters are liquid under standard conditions (particularly at a pressure of 1.013 bar and 0% relative atmospheric humidity, i.e., standard conditions STPD according to DIN 1343), and / or exist in liquid form.

[0065] In this respect, according to the invention, good results are obtained if the nitrate ester is a mono- or poly-alliphatic or alicyclic alcohol nitrate. In this respect, the invention particularly provides that the nitrate ester is selected from (i) nitrate esters of aliphatic or alicyclic alkanols, especially nitrate esters of straight-chain or branched aliphatic or alicyclic alkanols, preferably nitrate esters of hexanol, heptanol, octanol, ethylhexyl alcohol, and cyclohexanol; (ii) nitrate esters of aliphatic alkyl glycols, especially nitrate esters of ethylene glycol and propylene glycol and their oligomers and polymers (such as ethylene glycol or propylene glycol, ethylene or propylene triethylene glycol, and polyethylene glycol or polypropylene glycol); (iii) nitrate esters of aliphatic alkyltriols, especially nitrate esters of trimethylolethane, trimethylolpropane, glycerol, and glycerol; and (iv) nitrate esters of tetra- or poly-alliphatic alkanols.

[0066] Therefore, within the scope of this invention, large quantities of different nitrate esters can be advantageously purified and / or dried in a highly efficient and effective manner, thereby making the method of this invention highly flexible for application to many different nitrate esters.

[0067] In addition to being applicable to various nitrate esters, it is also advantageous within the scope of this invention to effectively and in a very high proportion remove from these nitrate esters a wide variety of, particularly volatile, impurities, which are typically generated during the production of nitrate esters. The fact that the method of this invention can effectively remove a variety of, particularly volatile, impurities (described in more detail below) from nitrate esters further highlights the advantageous flexibility and applicability of the method.

[0068] Similarly, the method of the present invention is advantageously characterized by the fact that nitrate esters of particularly high purity and / or quality can be obtained, which is especially due to the fact that, due to specific steps according to the invention, particularly volatile impurities (specifically defined in more detail below) that are typically introduced into the nitrate esters during the production and / or washing process can be removed substantially completely or as completely as possible from the nitrate esters.

[0069] If the volatile and / or volatile impurities are selected from the group consisting of: (i) unreacted and / or partially reacted starting materials and / or starting reagents; (ii) nitration and non-nitration reaction byproducts; (iii) degradation and oxidation products from nitration products and byproducts; (iv) inorganic acids, particularly sulfuric acid, nitric acid and nitrous acid, preferably nitric acid; (v) organic acids, particularly formic acid, acetic acid, oxalic acid, carbonic acid and hydrocyanic acid; (vi) nitrogen-containing bases, particularly ammonia (NH3); (vii) nitrogen oxides, particularly nitric oxide (NO), nitrogen dioxide (NO2) and nitrous oxide (N2O), as well as nitrous oxide and other nitrogen oxides (NO3). x (viii) carbon oxides, particularly carbon monoxide (CO) and carbon dioxide (CO2); (ix) solvent and / or washing medium residues, then the method according to the invention produces good results.

[0070] In this regard, preferably, the volatile and / or volatile impurities to be removed have higher volatility than the nitrate esters to be purified, particularly higher vapor pressure and / or lower boiling point, especially based on the vapor pressure of the nitrate esters under standard conditions (pressure of 1.013 bar; atmospheric humidity of 0% [standard conditions STPD according to DIN 1343]) and / or particularly based on the boiling point of the nitrate esters under standard conditions (pressure of 1.013 bar; atmospheric humidity of 0% [standard conditions STPD according to DIN 1343]).

[0071] It is particularly advantageous that the vapor pressure of the volatile and / or volatile impurities (especially water) to be removed is at least 5 mbar higher than that of the nitrate to be purified, preferably at least 7.5 mbar higher, and more preferably at least 10 mbar higher.

[0072] Similarly, it has been shown to be advantageous that the boiling point of the volatile impurities and / or volatile materials to be removed is at least 1°C lower than that of the nitrate ester to be purified, preferably at least 2.5°C lower, and more preferably at least 5°C lower.

[0073] Regarding the steps of the method of the present invention, it has proven advantageous that step (a) and / or washing are performed using liquid-liquid extraction. When step (a) is performed using liquid-liquid extraction, the large amount of water-soluble (especially volatile) impurities generated during the production of nitrate esters can be removed from these substances in a manner that is both efficient and simple in terms of equipment.

[0074] In this sense, the method step (a) performed by liquid-liquid extraction advantageously helps to remove the vast majority of non-volatile and / or non-volatile impurities, such as salts or residues of inorganic acids and / or nitrifying acids, from the crude nitrate ester obtained from the production process. Therefore, method step (a) makes a favorable contribution to the high overall purity achievable from the nitrate ester obtained by the method of the present invention.

[0075] Furthermore, it has proven advantageous for method step (a) to include acidic, alkaline (or alkali-containing) and / or neutral washing, particularly at least one alkaline (or alkali-containing) and / or neutral washing, preferably acidic, alkaline (or alkali-containing) and neutral washing. Thus, within the scope of method step (a), water-soluble and / or inorganic byproducts and / or segregates remaining from the crude nitrate obtained during the production process can be washed away substantially completely.

[0076] Furthermore, it is advantageous that method step (a) and / or washing are carried out in one or more washing stages, preferably in one, two, or three washing stages, more preferably in two or three washing stages; in particular, each washing stage includes one or more washing and / or extraction cycles (steps). Within the scope of the method according to the invention, this procedure also helps to particularly thoroughly purify nitrate esters.

[0077] Within the scope of this invention, it is also preferred that method step (a) and / or washing are performed using an aqueous washing medium; in particular, the aqueous washing medium is set to be neutral, acidic, or alkaline (containing alkali). In addition to good washing performance, using an aqueous washing medium ensures efficient separation of the washing medium from the washed nitrate esters, which remain, particularly in the form of an organic phase, while the washing medium forms an aqueous phase. This allows for simple and precise separation from the washed crude nitrate esters during the washing step and / or the washing process using the washing medium.

[0078] It has proven to be very effective and therefore advantageous that method step (a) and / or washing is performed in at least two stages, particularly three washing stages. Furthermore, the washing stages include at least one alkaline (alkali-containing) washing stage and a final neutral washing stage, preferably including a first acidic washing stage, a subsequent second alkaline (alkali-containing) washing stage, and a final third neutral washing stage.

[0079] Furthermore, within the scope of the method according to the invention, it has proven advantageous, particularly in each washing stage, to carry out method steps (a) and / or washing in a cross-flow or counter-flow or a combination of cross-flow and counter-flow. This is preferably carried out with the washing medium recycled.

[0080] Furthermore, according to the present invention, in method step (a), the separation of the washing medium is preferably carried out by a separation device (separator), particularly by a static separation device or a centrifugal separator.

[0081] Regarding method step (b), namely the drying and / or purification of the washed crude nitrate, preferably drying and purification, it has proven advantageous within the scope of the invention that method step (b) is carried out in a drying and / or purification apparatus, preferably in a drying and purification apparatus.

[0082] Preferably, the washed crude nitrate obtained in step (a) is transferred to a drying and / or purification apparatus, preferably a drying and purification apparatus, in step (b).

[0083] According to the invention, it has proven advantageous for drying and / or purification apparatuses to include column and / or gas / liquid reactors or stripping devices, said columns being particularly single-stage or multi-stage columns, preferably packed bed columns, sieve plate columns, bubble cap disk columns, or falling film columns, or combinations thereof. The aforementioned preferred drying and / or purification apparatuses advantageously allow nitrate esters to come into contact with inert gases and / or particularly to flow through (permeate) (this is provided within the scope of method step (b)), which is particularly effective and can be simply implemented technically and / or requires little effort. Therefore, integrating the aforementioned preferred apparatuses into the method of the invention, and particularly in conjunction with correspondingly suitable equipment and / or production facilities, advantageously allows for simplified procedures and / or procedures that improve process efficiency.

[0084] It has proven advantageous within the scope of this invention that, in method step (b), drying and / or purification (preferably drying and purification) is carried out as a continuous or discontinuous (especially continuous) process.

[0085] Furthermore, it has proven advantageous to perform drying and / or purification (preferably drying and purification) in method step (b) by gas-liquid extraction and / or by desorption, particularly by gas-liquid extraction.

[0086] A unique and advantageous aspect of the method of the present invention is that the drying and / or purification (preferably drying and purification) of the washed crude nitrate ester can be carried out by gas-liquid extraction and / or by desorption, because, in particular by this method and / or as a result, extremely high purity and / or dryness of the purified and / or dried nitrate ester, which is advantageously obtainable within the scope of the present invention, can be achieved.

[0087] Within the scope of this invention, desorption is understood to mean a process in which atoms and / or molecules of a substance (particularly in this case, as impurities present in the washed crude nitrate ester) enter the gas phase from the liquid (in which they exist in dissolved form). In this sense, gas-liquid extraction within the scope of this invention refers to an extraction method in which impurities and / or foreign substances dissolve from the liquid and enter the gas phase by contacting the liquid phase with a gas, particularly by flow, especially where impurities and / or foreign substances are removed from the liquid by continuous movement of the gas phase, particularly in the case of liquid flow.

[0088] In this regard, it is particularly advantageous that, for nitrate esters that may form explosive mixtures with air and / or explosive vapors, there has been no purification method to date that involves contacting and / or particularly circulating the nitrate ester with a gas, especially since no procedure has been provided to date to ensure that no explosive gas-nitrate mixture and / or nitrate vapors are generated during such contact and / or particularly circulation of the nitrate ester with the gas. In this respect, a particular advantage of the applicant is that the applicant has recognized that, particularly when using inert gases, it is possible to achieve gas-liquid extraction and / or purification and / or drying of nitrate esters by desorption, especially in conjunction with further preferred process parameters of the method of the invention, which have been mentioned herein and / or will be further described in detail below.

[0089] In this respect, according to the present aspect of the invention, the invention particularly also includes a method, especially as described above, for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrate esters (nitrates), particularly for removing water and volatile and / or volatile impurities specifically generated during the production and / or washing of nitrate esters. This method includes the following steps: (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. In this process, step (a) and / or washing are performed by liquid-liquid extraction; (b) Subsequently, the washed crude nitrate ester obtained in step (a) is dried and / or purified, preferably by contact with an inert gas, particularly by permeation, in such a way that water present in the washed crude nitrate ester is removed (i.e., the washed crude nitrate ester is dried), while and / or in the same manner, volatile and / or volatile impurities generated, particularly during the production and / or washing of the nitrate ester, are removed. Among them, drying and / or purification, preferably drying and purification are carried out as gas-liquid extraction and / or by desorption, especially as gas-liquid extraction; In particular, the volatile and / or volatile impurities are selected from the group consisting of: (i) unreacted and / or partially reacted starting materials and / or starting reagents; (ii) unnitrated reaction byproducts of nitration; (iii) degradation and oxidation products from nitration products and byproducts; (iv) inorganic acids, particularly sulfuric acid, nitric acid and nitrous acid, preferably nitric acid; (v) organic acids, particularly formic acid, acetic acid, oxalic acid, carbonic acid and hydrocyanic acid; (vi) nitrogen-containing bases, particularly ammonia (NH3); (vii) nitrogen oxides, particularly nitric oxide (NO), nitrogen dioxide (NO2) and nitrous oxide (N2O), as well as nitrous oxide and other nitrogen oxides (NO3). x (viii) Carbon oxides, particularly carbon monoxide (CO) and carbon dioxide (CO2); (ix) Solvent and / or washing media residues; and / or In particular, the volatile and / or volatile impurities to be removed have higher volatility, especially higher vapor pressure and / or lower boiling point compared to the nitrate ester to be purified, especially based on the vapor pressure of the nitrate ester under standard conditions (pressure of 1.013 bar; atmospheric humidity of 0% [standard conditions STPD according to DIN 1343]), and / or especially based on the boiling point of the nitrate ester under standard conditions (pressure of 1.013 bar; atmospheric humidity of 0% [standard conditions STPD according to DIN 1343]).

[0090] Regarding the procedure and / or design of step (b), it has proven advantageous within the scope of the invention to use the washed crude nitrate ester obtained in step (a) in step (b), and / or to use the washed crude nitrate ester obtained in step (a) in concentrated and / or undiluted form in step (b). Advantageously, within the scope of the invention, and particularly within the scope of the method according to the invention, no additional solvent is therefore required for the washed crude nitrate ester in step (b). Thus, a purified and / or dried, preferably purified and dried, product, i.e., pure nitrate ester and / or purified nitrate ester, can be obtained directly from step (b).

[0091] However, according to another, less preferred embodiment, method step (b) can also be carried out in the presence of an (additional) solvent (especially an inert solvent, such as dichloromethane). In this embodiment, the (additional) solvent can also be removed during method step (b). This embodiment can be considered if the preparation of the nitrate ester has already been carried out in such a solvent. This embodiment can also be considered if the solid nitrate ester needs to be dried and / or volatile impurities removed under standard conditions and / or under standard conditions (STPD) according to DIN 1343.

[0092] In this sense, within the scope of the invention, it is preferred that, in method step (b), no (additional) solvent and / or dispersant be added to the washed crude nitrate ester obtained in method step (a) for drying and / or purification, preferably drying and purification.

[0093] Regarding the inert gas, it has proven advantageous within the scope of this invention to select and / or design the inert gas in step (b) in such a way that it does not react with the nitrate ester under the conditions of step (b). Thus, within the scope of the method of this invention, it is advantageous to ensure to the greatest extent possible that no explosive mixture of nitrate ester and inert gas is generated, thereby ensuring process safety with particular reliability.

[0094] According to the present invention, in step (b) of the method, the inert gas is preferably selected from nitrogen, oxygen, rare gases (especially argon), hydrogen, carbon oxides and mixtures thereof, especially air; more preferably selected from nitrogen, oxygen, rare gases (especially argon) and mixtures thereof, especially air; particularly preferably selected from nitrogen, oxygen and mixtures thereof, especially air.

[0095] Furthermore, it has proven advantageous that in method step (b), the contact, particularly the flow, of the washed crude nitrate obtained in method step (a) with the inert gas is carried out in a cross-flow and / or counter-flow manner, preferably in a counter-flow manner.

[0096] In this context, it is particularly preferred that the inert gas is guided to flow upwards and the nitrate ester to flow downwards. This is particularly preferably carried out in a drying and / or purification apparatus, more preferably a column, especially a single-stage or multi-stage column, preferably a packed bed column, sieve plate column, bubble cap disk column, or falling film column or a combination thereof, and / or occurs in a gas / liquid reactor or stripping device. This special procedure allows for particularly effective mixing and very strong contact and / or mass exchange between the inert gas and the nitrate ester to be purified, which advantageously contributes to achieving high purity and dryness of the purified nitrate ester according to the present invention.

[0097] Furthermore, in step (b) of the method, the contact between the nitrate ester and the inert gas, particularly the flow, is advantageously carried out in the form of a dispersed, particularly finely dispersed, distribution of the inert gas within the nitrate ester. This advantageously generates a particularly large contact area between the inert gas and the nitrate ester to be purified. This further promotes a particularly efficient mass exchange between the inert gas and the liquid phase of the nitrate ester, thereby achieving a high degree of desorption, particularly of the volatile impurities to be removed, i.e., the high purity of the nitrate ester itself.

[0098] In this sense, it has also proven advantageous within the scope of this invention that, in method step (b), an inert gas is introduced into the nitrate ester using and / or in a dispersed, particularly finely dispersed, distribution. This is preferably achieved via a nozzle, jet mixer, jet pump, syringe, spray gun, sieve plate, and / or microporous membrane, and more preferably via a nozzle, jet mixer, and / or microporous membrane.

[0099] Furthermore, according to the present invention, it is preferred to use an inert gas in dry form in method step (b).

[0100] Within the scope of this invention, dry and / or dried gas (i.e., inert gas in dry form) is understood to specifically refer to a gas whose dew point is lower than the temperature at which step (b) of the method of the invention is performed, particularly wherein the dew point of the dry and / or dried gas is preferably at least 5°C lower than the temperature at which step (b) of the method of the invention is performed, more preferably at least 10°C, and most preferably at least 15°C.

[0101] In this context, it has proven particularly advantageous that the inert gas supplied and / or initially supplied at the beginning of method step (b) has a dew point of -20°C or lower, especially -30°C or lower, preferably -35°C or lower, more preferably -40°C or lower, and / or a dew point of -80°C or higher, especially -65°C or higher, preferably -55°C or higher, more preferably -50°C or higher.

[0102] Particularly preferably, the dew point range of the inert gas supplied and / or initially supplied at the start of method step (b) is -20°C to -80°C, particularly -30°C to -65°C, preferably -35°C to -55°C, and more preferably -40°C to -50°C.

[0103] Within the scope of the method of the present invention, inert gases with dew points within the aforementioned range exhibit ideal absorption performance for volatile impurities and / or moisture and / or water to be removed from nitrate esters.

[0104] Also preferably, the relative humidity range of the inert gas is 0 to 95%, particularly 0 to 90%, more preferably 0 to 85%, and even more preferably 0 to 80%. Within the scope of the method of the present invention, a relative humidity within the above range advantageously ensures that the inert gas has sufficient absorption capacity for moisture and / or water, as well as volatile and / or volatile impurities, from the nitrate ester to be purified.

[0105] Furthermore, regarding the specific process parameters of method step (b), it has proven advantageous within the scope of this invention that, in method step (b), when drying and / or purifying (preferably drying and purifying) and / or contacting with an inert gas (especially through flow), the volumetric flow rate of the inert gas is at least 100 L / h / kg nitrate ester (L / h / kg nitrate ester of volatile impurities to be dried and / or removed) or more, particularly 200 L / h / kg nitrate ester or more, preferably 300 L / h / kg nitrate ester or more, more preferably 350 L / h / kg nitrate ester or more, and / or the volumetric flow rate of the inert gas is 600 L / h / kg nitrate ester or less, particularly 500 L / h / kg nitrate ester or less, preferably 450 L / h / kg nitrate ester or less, more preferably 425 L / h / kg nitrate ester or less.

[0106] In step (b) of the method, drying and / or purification (preferably drying and purification) and / or contact with an inert gas are preferably carried out at an inert gas volume flow rate of 100 L / h / kg nitrate to 600 L / h / kg nitrate, particularly 200 L / h / kg nitrate to 500 L / h / kg nitrate, preferably 300 L / h / kg nitrate to 450 L / h / kg nitrate, more preferably 350 L / h / kg nitrate to 425 L / h / kg nitrate.

[0107] Furthermore, it has proven advantageous within the scope of this invention that, in method step (b), when the residence time of the nitrate ester in the presence of an inert gas is 30 seconds or longer, particularly 1 minute or longer, preferably 3 minutes or longer, more preferably 7 minutes or longer, and / or when the residence time of the nitrate ester in the presence of an inert gas is 20 minutes or less, particularly 17 minutes or less, preferably 14 minutes or less, more preferably 12 minutes or less, drying and / or purification (preferably drying and purification) and / or contact with an inert gas (particularly through flow) are performed.

[0108] Advantageously, in step (b) of the method, the nitrate ester is dried and / or purified (preferably dried and purified) and / or contacted with an inert gas (especially through a flow) under conditions where the residence time in the presence of an inert gas is 30 seconds to 20 minutes, particularly 1 minute to 17 minutes, preferably 3 minutes to 14 minutes, more preferably 7 minutes to 12 minutes.

[0109] Within the scope of this invention, the nitrate to be purified therefore advantageously requires only a relatively short residence time in the presence of an inert gas in order to achieve purification and / or drying results corresponding to target parameters that are preferred for the method according to the invention in terms of the purity and / or dryness of the purified and / or pure nitrate obtained.

[0110] In this sense, within the scope of the present invention, it is advantageous to achieve, relatively quickly and / or in a relatively short time, highly efficient and substantially complete and / or complete purification and / or drying of nitrates, which has been impossible in the prior art until now.

[0111] Furthermore, it has proven advantageous within the scope of this invention that, in method step (b), drying and / or purification (preferably drying and purification) and / or contact with an inert gas (particularly flow-through) are carried out at a temperature where the vapor pressure of the nitrate ester is less than 100 mbar, particularly less than 80 mbar, preferably less than 60 mbar, more preferably less than 50 mbar. This preferred method condition further ensures that, within the scope of this invention, particularly within method step (b) of the method of this invention, no explosive nitrate-inert gas mixture and / or explosive nitrate vapor are formed during the contact (particularly flow-through) of the nitrate ester with the inert gas. Therefore, high process safety is advantageously ensured, and this high process safety can be reliably and / or effectively maintained within the preferred process parameters of the method according to the invention, without the need for further and / or specific measures.

[0112] Within the scope of the invention, it has also proven advantageous that, in method step (b), the temperature during drying and / or purification (preferably drying and purification) and / or contact with an inert gas (particularly flow) is above 0°C, particularly above 5°C, preferably above 7.5°C, more preferably above 10°C, and / or below 60°C, particularly below 50°C, preferably below 40°C, more preferably below 35°C.

[0113] Preferably, in method step (b), the temperature range for drying and / or purifying (preferably drying and purifying) and / or contact with an inert gas (especially flow) is from 0°C to 60°C, particularly from 5°C to 50°C, preferably from 7.5°C to 35°C, and more preferably from 10°C to 30°C.

[0114] Similarly, it has proven advantageous that in method step (b), drying and / or purification (preferably drying and purification) and / or contact with an inert gas (especially flow) are carried out at atmospheric pressure (normal pressure; 1.01325 bar) or vacuum (depressurization) or ultra-atmospheric pressure, preferably at atmospheric pressure.

[0115] Here, preferably in method step (b), drying and / or purification (preferably drying and purification) and / or contact with an inert gas (especially flow) are carried out at an absolute pressure of 0.1 bar to 3 bar, especially 0.3 bar to 1.2 bar, preferably 0.5 bar to 1.1 bar, more preferably about 1 bar.

[0116] Regarding the process parameters of temperature and pressure, the method of the present invention is advantageously characterized by its ability to operate consistently within a moderate temperature range, particularly in the purification apparatus performing step (b), without increasing pressure load. This should be considered advantageous, especially in terms of the efforts made in the equipment and / or construction of the method and apparatus. Similarly, operating within the preferred moderate temperature and pressure range makes a valuable contribution to providing a relatively energy-efficient and environmentally friendly process in this respect.

[0117] According to the invention, it is also preferably provided that the amount of inert gas used in step (b) is selected and / or set according to the drying and / or purification conditions, particularly temperature and / or pressure and / or the duration of drying and / or purification and / or the type of inert gas, and / or according to the content and / or type of impurities in the nitrate ester to be purified, and / or according to the desired residual content of volatile impurities in the resulting purified nitrate ester.

[0118] In this regard, it has proven particularly advantageous that the amount of inert gas used in step (b) is calculated as the volume (in standard cubic meters) of inert gas under standard conditions (pressure: 1.013 bar; atmospheric humidity: 0%, i.e., dry inert gas; temperature: 0°C [standard conditions STPD according to DIN 1343]), from 0.5 to 500 standard cubic meters, particularly from 2 to 200 standard cubic meters, preferably from 5 to 100 standard cubic meters, and more preferably from 8 to 70 standard cubic meters.

[0119] Similarly, it has proven advantageous within the scope of this invention that the amount of inert gas used in step (b) is calculated as the amount and / or weight of inert gas under standard conditions (pressure: 1.013 bar; atmospheric humidity: 0%, i.e., dry inert gas; temperature: 0°C [standard conditions STPD according to DIN 1343]) for 1 ton of nitrate ester to be purified, from 1 to 250 kg, particularly from 2 to 140 kg, preferably from 5 to 50 kg, and more preferably from 10 to 40 kg.

[0120] Advantageously, within the scope of the invention, it is particularly achieved that, after drying and / or purification (preferably drying and purification), the water content of the nitrate ester is at most 0.06 wt%, particularly at most 0.03 wt%, preferably at most 0.02 wt%, more preferably at most 0.01 wt%, based on the nitrate ester.

[0121] In particular, within the scope of the invention, it is preferred that, after drying and / or purification (preferably drying and purification), the water content of the nitrate ester, based on the nitrate ester, is in the range of 0.00001 to 0.06 wt%, particularly 0.0001 to 0.03 wt%, preferably 0.0005 to 0.02 wt%, more preferably 0.0005 to 0.01 wt%.

[0122] Similarly, within the scope of the invention, it can be advantageously achieved that, after drying and / or purification (preferably drying and purification), the nitrate ester contains, in particular, volatile impurities, at a level of up to 100 ppm, particularly up to 30 ppm, preferably up to 25 ppm, more preferably up to 20 ppm, and even more preferably up to 10 ppm.

[0123] Particularly preferably, after drying and / or purification (preferably drying and purification), the nitrate ester contains, in particular, volatile impurities in the amount of 0.001 to 100 ppm, especially 0.001 to 30 ppm, preferably 0.001 to 25 ppm, more preferably 0.002 to 20 ppm, and even more preferably 0.005 to 10 ppm.

[0124] Therefore, the present invention provides purified and / or dried nitrate esters, which in particular have a very low proportion of volatile impurities and / or liquids and / or moisture, especially compared with nitrate esters obtained by purification and / or drying methods in the prior art. In this sense, they can be regarded as and / or defined as substantially free of, in particular, volatile impurities and substantially free of water and / or moisture.

[0125] Specifically, the method of the present invention can advantageously provide a nitrate ester with a cloud point below 0°C, i.e., a moisture content of less than 0.02% (by weight of moisture and / or water). Achieving such a low level of moisture using conventional methods of the prior art requires significantly more effort and is hardly economical or feasible in this respect. Similarly, the method of the present invention can advantageously provide a nitrate ester, particularly with a proportion of volatile impurities preferably not exceeding 10 ppm.

[0126] Overall, the method of the present invention advantageously provides the possibility of efficiently drying and / or purifying nitrate esters, while achieving a more rigorous and less complex process, and therefore less prone to error. Furthermore, the method of the present invention can be implemented in a resource-saving manner, particularly regarding the possibility of recovering the process media used (especially inert gases).

[0127] Regarding the inert gas, and particularly regarding the method stage after the inert gas has passed through and / or contacted with the crude nitrate ester and thus absorbed moisture and / or water, within the scope of the invention, it is preferably provided in this respect that, after method step (b) and / or after contact with the nitrate ester, particularly after flow, the relative humidity and / or relative residual moisture of the inert gas is 50% or more, particularly 65% ​​or more, preferably 75% or more, more preferably 80% or more, and especially preferably 90% or more, based on a gas temperature of 20°C to 30°C.

[0128] Within the scope of the method of the present invention, the inert gas used in step (b) can achieve a relatively high moisture and / or water load, which is particularly advantageous in step (b), especially during the relatively short residence time of the nitrate ester in the presence of the inert gas, to achieve extremely high dryness of the nitrate ester and high desorption of impurities (especially volatile impurities) contained in the crude nitrate ester to be purified and / or dried. This aspect further highlights the particular efficiency of the method of the present invention.

[0129] Furthermore, regarding the procedure of the method of the present invention, particularly within the scope of method step (b), it has proven advantageous within the scope of the invention that the dried and / or purified (preferably dried and purified) nitrate ester obtained after method step (b) is obtained and / or collected separately, and / or obtained and / or collected separately from the inert gas.

[0130] In this context, it is particularly provided that no additional separation steps are required to separate the dried and / or purified (preferably dried and purified) nitrate obtained after method step (b) from the inert gas.

[0131] Furthermore, at this stage of the method of the present invention, particularly after method step (b) has been performed or completed, it is preferable to recover and / or recycle the inert gas after method step (b). Specifically, the recovery and / or recycling of the inert gas after method step (b) is performed after and / or simultaneously with the drying and purification of the inert gas.

[0132] Within the scope of the process execution according to the method of the invention, a significant reduction in the consumption of process media can be advantageously achieved, which also improves the cost-effectiveness of the method and facilitates the utilization and / or treatment of process chemicals and / or process components.

[0133] In this respect, within the scope of the present invention, the process medium (i.e., the inert gas) in method step (b) can be recycled, which constitutes a significant advantage of the method of the present invention over the prior art.

[0134] In this regard, it has proven advantageous within the scope of the invention to dry and purify the inert gas after method step (b), particularly by means of a condenser and / or a gas scrubber or a combination thereof.

[0135] Similarly, it has proven advantageous within the scope of this invention that the inert gas obtained and / or separated after method step (b), particularly inert gases containing water and / or moisture and especially volatile impurities, is transferred to a recovery device for gas treatment.

[0136] Preferably, there is a temperature gradient between the drying and / or purification apparatus performing step (b) and the recovery apparatus for treating inert gases loaded with water and / or moisture, and particularly volatile impurities.

[0137] The temperature gradient is specially designed so that the temperature set in the recovery unit is lower than the temperature in the drying and / or purification unit, or provides a lower temperature during the execution of method step (b). Therefore, a temperature gradient that decreases from the drying and / or purification unit to the recovery unit in the process direction is preferred.

[0138] Specifically, the temperature gradient difference between the drying and / or purification device and the recovery device is 5°C or more, particularly 10°C or more, preferably 13°C or more, and more preferably 15°C or more. In this sense, the temperature during gas treatment is therefore advantageously 5°C or more, particularly 10°C or more, preferably 13°C or more, and more preferably 15°C or more, lower than the temperature provided in step (b) of the method.

[0139] Furthermore, it has proven advantageous that the temperature difference is 30°C or lower, particularly 25°C or lower, preferably 22°C or lower, more preferably 20°C or lower, and / or the temperature during the gas treatment process is 30°C or lower than the temperature in the range of method step (b), particularly 25°C or lower, preferably 22°C or lower, more preferably 20°C or lower.

[0140] Most preferably, the temperature gradient difference between the drying and / or purification device and the recovery device is in the range of 5°C to 30°C, particularly 10°C to 25°C, preferably 13°C to 22°C, more preferably 15°C to 20°C; and / or the temperature during the gas treatment process is therefore advantageously 5°C to 30°C lower than the temperature in the range of method step (b), particularly 10°C to 25°C, preferably 13°C to 22°C, more preferably 15°C to 20°C.

[0141] In this context, the inert gas needs to be treated to separate water and / or moisture and, in particular, volatile impurities. This treatment is preferably carried out by condensation and / or washing, more preferably by condensation and washing. Furthermore, it is preferable that the temperature during this treatment is lower than the temperature in step (b) of the method.

[0142] In order to carry out this process, particularly by condensation, and in this respect preferably to set a preferred temperature gradient, refrigerants, coolants (particularly cold water and / or cooling water) and / or cooling gases (particularly cold air and / or cooling air), especially for cooling recovery devices used for inert gas treatment, can be used.

[0143] Accordingly, within the scope of the invention, a recovery apparatus for treating and recovering gases preferably includes a condenser and / or a gas scrubber or a combination thereof. In particular, the use of a condenser allows for the rapid drying of inert gases, thus reintroducing them into the method of the invention in a time-efficient and technologically simple manner. Specifically, treating gases loaded with water and / or moisture, and especially volatile impurities, in a recovery apparatus comprising a condenser (particularly composed of a condenser) allows for the efficient separation of moisture and / or water from the gas, thereby achieving a high degree of purification and, particularly, dryness of the inert gas with relatively little effort in terms of process technology and time. In this respect, volatile and / or readily volatile impurities are also advantageously, particularly substantially completely, retained in the separated moisture and / or aqueous phase. Thus, it is also advantageous to achieve, for example, the collection and neutralization of harmful impurities, particularly volatile impurities, dissolved from nitrate esters by inert gases, and in any case, their non-filtration release into the environment.

[0144] Accordingly, it has proven advantageous in this context to recover the treated inert gas into method step (b). The inert gas treated as described above has sufficient dryness and purity to be reintroduced into the process (i.e., recovered) and subjected to multiple process cycles, and reused for the purification and drying of crude nitrate esters, thereby saving process media and operating more efficiently and resource-wise.

[0145] Similarly, within the scope of this invention, it is preferred to treat the condensate generated from the inert gas and / or the resulting washing medium, particularly by recycling it after preparation and / or purification. The condensate generated after treating the inert gas is preferably recovered and / or introduced into the washing process of step (a) of the method.

[0146] Therefore, within the scope of the present invention, it is preferable to recover and recycle the inert gas from method step (b), and in this regard, to dry and / or purify it before recovery. In this way, the method of the present invention can be implemented in a resource-saving and cost-effective manner compared with the prior art, and thus can also be implemented efficiently in terms of the process media consumed from an economic point of view.

[0147] In addition to the exceptionally high quality of purified nitrates and / or pure nitrates obtainable through the method of this invention, this aspect is also a significant advantage of this invention in the context of the prior art, which typically focuses on designing, especially on large-scale production and purification methods, in an eco-friendly, cost-effective, and valuable manner. This becomes possible through the method of this invention.

[0148] Since the condensate and / or moisture collected from the purified inert gas can also be recovered to step (a) of the method, not only is washing medium saved within the scope of the invention, but also undue loss of product (i.e., purified nitrate esters and / or pure nitrate esters) can be significantly minimized. Specifically, according to the preferred procedure of the invention, fractions of the nitrate esters to be purified that may have been carried away by the inert gas during the drying and purification process are allowed to be recovered during the process. These fractions may (e.g.) enter the condensate phase in the condenser, whereby they can be collected or washed out in a gas scrubber. Thus, within the scope of the washing step (a), entrained nitrate esters removed from the gas can be returned to the method of the invention, thereby significantly reducing overall product loss within the scope of the invention.

[0149] In this way, the present invention also significantly improves the absolute yield of purified nitrates compared to known nitrate purification methods in the prior art. In this regard, it should be particularly considered that prior art methods cannot achieve the nitrate purity and / or dryness allowed by the present invention, and are generally accompanied by greater product loss. Therefore, in both respects, the method of the present invention advantageously provides a significant improvement over the prior art, which directly (especially substantially quantitatively) affects the product yield achievable within the scope of the present invention.

[0150] Furthermore, the subject matter of the invention according to this aspect is a method for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrates (nitrates), particularly for removing water and volatile and / or volatile impurities specifically generated during the production and / or washing of nitrates, especially the method described above. This method includes the following steps: (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. In particular, step (a) and / or washing are performed as liquid-liquid extraction; (b) Subsequently, the washed crude nitrate ester obtained in step (a) is dried and / or purified, preferably dried and purified, particularly by contacting it with an inert gas, especially by permeation (flow through), thereby removing water present in the washed crude nitrate ester (i.e., the washed crude nitrate ester is dried), and simultaneously and / or in the same manner removing volatile and / or volatile impurities generated particularly during the production and / or washing of the nitrate ester. In particular, drying and / or purification (preferably drying and purification) are carried out as gas-liquid extraction and / or by desorption, especially as gas-liquid extraction; Wherein, after method step (b), the inert gas is recovered and / or recycled, particularly after and / or during drying and purification; specifically, after method step (b), the inert gas undergoes drying and purification treatment, particularly by means of a condenser and / or a gas scrubber or a combination thereof; and / or The inert gas obtained and / or separated after method step (b), particularly the inert gas loaded with water and / or moisture and particularly volatile impurities, is conveyed to an apparatus for treating and recovering the gas; particularly wherein the inert gas is treated to separate water and / or moisture and particularly volatile impurities, preferably by condensation and / or washing, more preferably by condensation and washing, and / or particularly wherein the apparatus for treating and recovering the gas includes a condenser and / or a gas scrubber or a combination thereof; In particular, the treated inert gas is recovered to method step (b); and / or in particular, the condensate and / or the washing medium obtained after treating the inert gas are recycled, especially after preparation and / or purification, preferably recycled to the washing in method step (a).

[0151] Last but not least, it has proven particularly advantageous for the method of the present invention that the production of crude nitrate is carried out by adiabatic or isothermal nitration, and / or the production process of crude nitrate includes, or is precisely adiabatic or isothermal nitration. This production method has particularly advantageous compatibility with the drying and / or purification methods of the present invention.

[0152] For further details regarding the foregoing aspects of the invention, please refer to the description of other aspects of the invention, which are equally applicable to the present aspects of the invention.

[0153] Furthermore, according to a second aspect of the invention, the subject matter of the invention is an apparatus for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrates (nitrate esters), particularly for removing water and volatile impurities specifically generated during the production and / or washing of nitrate esters, preferably by contact with an inert gas, particularly by flow (permeation), and especially for carrying out the method according to any one of the preceding claims. The device has the following equipment, which are arranged sequentially in the process flow: - At least one washing device for washing crude nitrate ester obtained from the production process and / or derived from the production equipment with a washing medium, wherein a separation device is provided downstream and / or connected to the device for separating the washing medium from the washed crude nitrate ester; located downstream and / or connected downstream of the washing device in the process direction. - At least one purification and / or drying device, particularly a column, for drying and / or purifying, especially drying and purifying, crude nitrate esters obtained from washing equipment after washing. The purification and / or drying equipment includes a first inlet device and a second inlet device. The first inlet device is specifically located in the upper region of the purification and / or drying equipment, particularly at the top of the column, for introducing and / or feeding the washed crude nitrate ester into the purification and / or drying equipment. The second inlet device is specifically located in the lower region of the purification and / or drying equipment, particularly at the bottom of the column, for introducing and / or feeding the dried inert gas into the purification and / or drying equipment. The purification and / or drying equipment includes means for contacting the washed crude nitrate with a dry inert gas, particularly for allowing a flow, wherein the means for contacting, particularly for allowing a flow, is designed such that, while obtaining a dry (dried) nitrate free of, in particular, volatile impurities, water present in the washed crude nitrate is removed (i.e., the washed crude nitrate is dried), and volatile impurities generated, particularly during the production and / or washing of the nitrate are removed simultaneously and / or in the same manner; downstream of and / or connected to the purification and / or drying equipment in the process direction. - At least one recovery device for recovering and / or recycling inert gases, The recovery equipment includes separation equipment for separating water and / or moisture, as well as particularly volatile impurities, especially condensers and / or gas scrubbers or combinations thereof. In particular, the separation equipment is designed such that water and / or moisture, as well as particularly volatile impurities, are separated from the wet inert gas, particularly by condensation and / or scrubbing, preferably condensation and scrubbing, while obtaining a dry (dried) inert gas free of particularly volatile impurities. In particular, the recovery device further includes a third inlet device specifically located between the upper region (particularly the top of the column) of the purification and / or drying device and the recovery device, for introducing and / or supplying and / or conveying wet inert gas from the purification and / or drying device, particularly loaded with water and / or particularly volatile impurities, into the recovery device.

[0154] In addition to the advantages of combining the methods of this invention, which are also transferable to the apparatus of this invention, the unique feature of the apparatus of this invention for drying and / or purifying nitrate esters is particularly its ability to efficiently dry and / or purify nitrate esters within a process that is both economical and strictly follows process engineering, using a correspondingly simplified set of equipment and / or apparatus. This contributes to the low sensitivity of the apparatus of this invention to errors and / or malfunctions, as well as ease of operation and maintenance, while also contributing to high process stability and safety, accompanied by relatively high production and convertibility.

[0155] According to the invention, the device can also be implemented with easily controllable effort in terms of structure and / or process technology, especially because in the device of the invention, those highly compatible devices that can be efficiently connected with commonly available equipment are combined together.

[0156] In this sense, it has proven advantageous within the scope of this invention to design the first inlet device as a connection between the washing equipment and the purification and / or drying equipment. It is also advantageous to design the first inlet device as a delivery line, particularly for connecting the washing equipment to the purification and / or drying equipment.

[0157] Similarly, within the scope of this invention, it is preferred to design the second inlet device as a connection between a storage device for dry inert gas and a purification and / or drying device.

[0158] The second inlet device is also preferably designed as a delivery pipeline, particularly for connecting the storage device for dry inert gas with the delivery pipeline for purification and / or drying equipment.

[0159] In this sense, according to the invention, it is also preferred that the third inlet device be designed as a connection between the purification and / or drying equipment and the recycling equipment. The third inlet device is also preferably designed as a conveying line, particularly for connecting the purification and / or drying equipment and the recycling equipment.

[0160] Furthermore, regarding the washing equipment, it has proven advantageous within the scope of this invention that the washing equipment is designed as a liquid-liquid extraction device.

[0161] Also preferably, the washing equipment includes an acidic washing stage, an alkaline (alkali-containing) washing stage and / or a neutral washing stage, particularly at least one alkaline (alkali-containing) washing stage and / or a neutral washing stage, preferably one acidic, alkaline (alkali-containing) and neutral washing stage.

[0162] Furthermore, or as an alternative, it has proven advantageous for the washing equipment to include one or more washing stages, preferably one, two, or three washing stages, more preferably two or three washing stages. In particular, each washing stage is designed in such a way that it may include one or more washing and / or extraction cycles.

[0163] Furthermore, a preferred objective is that the washing equipment is designed in such a way that washing is performed using a water-based washing medium. In particular, it is preferable that the water-based washing medium is neutral, acidic, or alkaline (containing alkali).

[0164] Furthermore, good results can be obtained within the scope of this invention if the washing equipment is designed in such a way that washing (especially in each washing stage) is carried out in a cross-flow or counter-flow or a combination of cross-flow and counter-flow.

[0165] This is preferably achieved by recycling the washing medium.

[0166] Also preferably, the washing equipment is operable and / or capable of operating, particularly in each washing stage, in a cross-flow or counter-flow or a combination of cross-flow and counter-flow. This is also preferably achieved by utilizing the circulation of the washing medium.

[0167] Furthermore, it has proven advantageous for the apparatus according to the invention to design the separation device connected downstream of the washing equipment as a separation device (separator), particularly a static separation device or a centrifugal separator.

[0168] Furthermore, regarding purification and / or drying equipment, it has proven advantageous within the scope of this invention that purification and / or drying equipment (particularly columns) includes single-stage or multi-stage columns, particularly packed bed columns, sieve plate columns, bubble cap disc columns or falling film columns or combinations thereof, and / or includes gas / liquid reactors or stripping equipment.

[0169] In particular, good results can be obtained according to the invention if the purification and / or drying equipment (especially columns) is a single-stage or multi-stage column, especially a packed bed column, sieve plate column, bubble cap plate column or falling film column or a combination thereof, and / or a gas / liquid reactor or stripping equipment.

[0170] Furthermore, within the scope of the invention, it is preferred that the purification and / or drying equipment (in particular columns) be designed in such a way that drying and / or purification (preferably drying and purification) is carried out as a continuous or discontinuous (in particular continuous) process.

[0171] In addition, purification and / or drying equipment, particularly columns, preferably including outlet and / or discharge equipment, which are particularly located in the lower region, preferably at the bottom of the column, for drying (already dried) nitrates, especially those free of volatile impurities.

[0172] In this regard, it has proven advantageous that outlet and / or discharge equipment is designed as a connection between purification and / or drying equipment and collection and / or storage equipment for dried (pre-dried) nitrates that are particularly free of volatile impurities. The outlet and / or discharge equipment is also preferably designed as a conveying line, particularly for connecting purification and / or drying equipment to collection and / or storage equipment for dried (pre-dried) nitrates that are particularly free of volatile impurities.

[0173] Preferably, the purification and / or drying equipment, particularly the column, is designed as a single-stage or multi-stage packed bed column, sieve plate column, bubble cap plate column, or falling film column, or a combination thereof, with the bottom of the column serving as a lower region. The purification and / or drying equipment preferably includes an outlet and / or discharge device, preferably located at the bottom of the column, for drying nitrate esters, especially those free of volatile impurities.

[0174] In this regard, it has proven particularly advantageous that the outlet and / or discharge equipment is designed as a connection between the purification and / or drying equipment and the collection and / or storage equipment for dried (pre-dried) nitrates that are particularly free of volatile impurities. It is also preferred that the outlet and / or discharge equipment be designed as a conveying line, particularly for connecting the purification and / or drying equipment to the collection and / or storage equipment for dried (pre-dried) nitrates that are particularly free of volatile impurities.

[0175] Furthermore, it has proven advantageous according to the invention that the purification and / or drying equipment is designed as a gas-liquid extraction equipment and / or a desorption equipment, particularly as a gas-liquid extraction equipment.

[0176] According to the invention, it is also preferred that the purification and / or drying equipment, particularly the equipment for contacting the washed crude nitrate with a dry inert gas, especially the equipment for circulating the washed crude nitrate with the dry inert gas, be designed such that the contact, and particularly the circulation, of the washed crude nitrate obtained from the washing equipment with the dry inert gas is carried out in a cross-flow and / or counter-flow manner, preferably in a counter-flow manner.

[0177] In this context, it has proven particularly advantageous to purify and / or dry equipment, especially equipment for contacting washed crude nitrate with dry inert gas, particularly equipment for circulating washed crude nitrate with dry inert gas, in such a way that the dry inert gas is guided to flow upwards while the washed crude nitrate is guided to flow downwards.

[0178] Furthermore, it has proven advantageous for the apparatus according to the invention that the recovery device comprises at least two discharge devices for discharging dry (dried) inert gases, particularly those without volatile impurities, and / or for discharging water and / or moisture obtained from processing the inert gases, and / or for discharging washing liquid, particularly having volatile impurities from the wet inert gases.

[0179] In this regard, it is particularly preferred that the emission equipment is designed as a direct and / or indirect connection between the recovery equipment and the purification and / or drying equipment, especially through a second inlet device. It is also preferred that the emission equipment is designed as a pipeline for conveying dry (pre-dried) inert gases that are particularly free of volatile impurities, preferably designed as a pipeline for conveying dry (pre-dried) inert gases that are particularly free of volatile impurities, and designed in such a way as a direct and / or indirect connection between the recovery equipment and the purification and / or drying equipment, especially through a second inlet device, thereby achieving the recovery and / or circulation of the inert gases.

[0180] Similarly, according to the invention, it is preferred that the discharge device is designed as a connection between the recovery device and the washing device, and / or particularly wherein the discharge device is designed as a delivery pipeline for conveying water and / or moisture obtained from the treatment of inert gas and / or washing liquid containing, in particular, volatile impurities from the wet inert gas.

[0181] The emission equipment is particularly preferably designed as a delivery pipeline for conveying water and / or moisture and / or washing liquid containing volatile impurities from the wet inert gas obtained from gas treatment, and for connecting the recovery equipment and the washing equipment, in such a way that the water and / or moisture and / or washing liquid containing volatile impurities from the wet inert gas obtained from the gas treatment are recovered and / or recycled.

[0182] Furthermore, a temperature gradient is preferably present between the drying and / or purification equipment and the recovery equipment for treating inert gases containing water and / or moisture, and particularly volatile impurities. This temperature gradient is specifically designed such that the temperature in the recovery equipment is set lower than the temperature in the drying and / or purification equipment. Therefore, a temperature gradient that decreases in the process direction from the drying and / or purification equipment to the recovery equipment is preferably present.

[0183] Furthermore, within the scope of this invention, it is preferred that the recovery device is designed as a condenser and / or a gas scrubber or a combination thereof.

[0184] In particular, it has proven advantageous for the recovery equipment T to be designed as a condenser, which contains refrigerant, coolant (especially chilled water and / or cooling water) and / or cooling gas (especially chilled air and / or cooling air), especially for cooling recovery equipment that performs inert gas treatment.

[0185] Finally, according to the present invention, it is generally preferred that the above-described apparatus be designed to perform the above-described method. Particularly preferably, the apparatus according to the present invention is characterized in this respect by one or more of the above-described features of the method according to the present invention.

[0186] For further details regarding this aspect of the invention, particularly its advantages and specific technical effects, please refer to the description of the method of the invention, which also applies accordingly to this aspect of the invention.

[0187] Furthermore, according to a third aspect of the invention, the subject matter of the invention is a production apparatus for producing aliphatic or alicyclic nitrates (nitrates), the production apparatus comprising: (i) In particular, nitration equipment having one or more reaction vessels (nitration reactors) for carrying out nitration, especially for the production of aliphatic or alicyclic nitrates (nitrates) from mono- or poly-aliphatic or alicyclic alcohols, preferably by adiabatic or isothermal nitration; (ii) Optionally, a separation device, particularly a separator, is arranged downstream of the production line and / or connected downstream of the nitration equipment, especially for separating residual nitrated acid from the crude product (crude nitrate ester) of nitration; (iii) At least one washing device, arranged downstream of the production line and / or connected downstream of the nitration device and optionally a separation device, for washing crude nitrate ester obtained from the production process and / or from the production equipment with a washing medium, and the separation device, arranged downstream and / or connected downstream, for separating the washing medium from the washed crude nitrate ester. (iv) At least one purification and / or drying device, particularly a column, arranged downstream of the production line and / or connected downstream of the washing equipment, for drying and / or purifying, in particular drying and purifying, the crude nitrate obtained from the washing equipment after washing. The purification and / or drying equipment includes a first inlet device and a second inlet device. The first inlet device is specifically located in the upper region of the purification and / or drying equipment, particularly at the top of the column, for introducing and / or feeding the washed crude nitrate ester into the purification and / or drying equipment. The second inlet device is specifically located in the lower region of the purification and / or drying equipment, particularly at the bottom of the column, for introducing and / or feeding the dried inert gas into the purification and / or drying equipment. The purification and / or drying equipment includes means for contacting the washed crude nitrate with a dry inert gas, particularly for allowing flow, wherein the means for contacting, particularly for allowing flow, is designed such that water present in the washed crude nitrate is removed (i.e., the washed crude nitrate is dried), and volatile impurities generated, particularly during the production and / or washing of the nitrate, are removed in the same manner, thereby obtaining dried (pre-dried) nitrate free of, in particular, volatile impurities; arranged downstream and / or connected downstream of the purification and / or drying equipment in the process direction. (v) At least one recovery device, arranged downstream of the production line and / or connected downstream of the purification and / or drying arrangement (especially a column), for recovering and / or circulating inert gases. The recovery equipment includes separation equipment for separating water and / or moisture, and particularly volatile impurities, particularly condensers and / or gas scrubbers or combinations thereof, wherein the separation equipment is designed such that water and / or moisture, and particularly volatile impurities, are separated from the wet inert gas, particularly by condensation and / or scrubbing, preferably condensation and scrubbing, while obtaining a dry (dried) inert gas free of particularly volatile impurities; In particular, the recovery device further includes a third inlet device specifically located between the upper region (particularly the top of the column) of the purification and / or drying device and the recovery device, for introducing and / or supplying and / or conveying wet inert gas (particularly loaded with water and / or particularly volatile impurities) from the purification and / or drying device to the recovery device.

[0188] The main features of the production apparatus according to the invention lie in the advantages and / or technical features described in conjunction with the method and apparatus according to the invention. In particular, the technical features of the apparatus according to the invention are embodied in the production apparatus according to the invention, and the production apparatus according to the invention is advantageously suited for performing and / or implementing the method according to the invention, as described at the outset, especially where the particularly high efficiency of the method according to the invention and its resource-saving implementation are determined, and / or manifested, in particular by, the arrangement and / or nature of the equipment included in the production apparatus according to the invention.

[0189] In this regard, the subject matter of the invention according to this aspect is also particularly the production apparatus as described above, which includes: (i) Nitration equipment, particularly equipped with one or more reaction vessels (nitration reactors) for carrying out nitration, especially for the production of aliphatic or alicyclic nitrates (nitrates) from mono- or poly-aliphatic or alicyclic alcohols, preferably by adiabatic or isothermal nitration; (ii) Optionally, a separation device, particularly a separator, arranged downstream of the production line and / or connected downstream of the nitration unit, is provided, especially for separating residual nitrated acid from the crude product (crude nitrate ester) of the nitration. (iii) An apparatus arranged downstream of the production line and / or connected downstream of the nitration equipment and optionally the separation equipment, according to the invention or as described above.

[0190] Preferably, the production apparatus is designed within the scope of the present invention to perform the method according to the present invention described above.

[0191] Specifically, within the scope of this invention, it is preferred that the production apparatus according to the invention is characterized by one or more features of the method according to the invention and / or the apparatus according to the invention.

[0192] For more details concerning this aspect of the invention, particularly regarding its advantages and specific technical effects, please refer to the description of the foregoing aspects of the invention, which also applies accordingly to this aspect of the invention.

[0193] Finally, according to a fourth aspect of the invention, the subject of the invention is the use of an inert gas for drying and / or purifying, preferably drying and purifying, crude aliphatic or alicyclic nitrates (nitrate esters) obtained from the production process, particularly for removing water and volatile impurities specifically generated during the production and / or washing of nitrate esters.

[0194] Furthermore, the subject of the invention according to this aspect is the use of an inert gas for drying and / or purifying, preferably drying and purifying, crude aliphatic or alicyclic nitrates (nitrates) obtained from a production process, particularly for removing water and volatile and / or volatile impurities generated especially during the production and / or washing of nitrates, by contacting the crude aliphatic or alicyclic nitrate with an inert gas, particularly by permeation, in such a manner that water present in the washed crude nitrate (i.e., the washed crude nitrate is dried), and simultaneously and / or in the same manner removing volatile and / or volatile impurities generated during the production and / or washing of nitrates.

[0195] Within the scope of this invention, and for its intended use, it has proven particularly advantageous that: (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. (b) Subsequently, the washed crude nitrate ester obtained by this method is dried and / or purified, preferably dried and purified, in particular by contact with an inert gas, in particular by flow (permeation), in such a way as to remove water present in the washed crude nitrate ester (i.e. the washed crude nitrate ester is dried), and simultaneously and / or in the same way to remove volatile and / or volatile impurities generated particularly during the production and / or washing of the nitrate ester.

[0196] Furthermore, the subject matter of the present invention according to the present aspect is the use of inert gases in the methods described above according to the invention, and / or the apparatus described above according to the invention, and / or the production apparatus described above according to the invention, for drying and / or purification, preferably drying and purification.

[0197] For the purposes described in this invention, it is preferably provided that the purposes are characterized by one or more features of the method and / or apparatus and / or production apparatus described in this invention.

[0198] For further details concerning this aspect of the invention, particularly its advantages and specific technical effects, see the statements relating to other aspects of the invention, which also apply mutatis mutandis to this aspect. Attached Figure Description

[0199] The present invention will now be explained in more detail with reference to the accompanying drawings and preferred embodiments. In conjunction with the explanation of these preferred embodiments or implementations (however, they in no way constitute a limitation thereof), other advantages, features, aspects, and characteristics of the invention will also be pointed out.

[0200] The individual accompanying drawings (including the following description of the drawings) and the following embodiments are for illustrative purposes only and are not intended to limit the invention thereto.

[0201] According to the following Figure 1 The detailed description of the preferred embodiment according to the present invention is shown in the single-figure illustration. Figure 1 Schematic diagrams are shown of embodiments and / or arrangements of production apparatuses according to the invention, which also include equipment according to the invention, and schematic diagrams of the sequence of methods according to the invention, each according to a specific embodiment. Detailed Implementation

[0202] Figure 1 A preferred embodiment of the apparatus according to the invention is shown (particularly as a component of the production equipment according to the invention), which is used for drying and / or purifying aliphatic or alicyclic nitrates, particularly for removing water and volatile and / or volatile impurities generated, especially during the production and / or washing of nitrates; Figure 1 A preferred embodiment of a production apparatus according to the invention, comprising the apparatus, is also shown, the production apparatus being used to produce aliphatic or alicyclic nitrates.

[0203] Specifically, Figure 1 A preferred example of an embodiment of the method according to the invention is also shown, which is used for drying and / or purifying aliphatic or alicyclic nitrates, particularly for removing water and volatile and / or volatile impurities that are specifically generated during the production and / or washing of nitrates.

[0204] In this regard, according to Figure 1 The production facilities include: (i) Nitrification equipment P NE In particular, it has one or more reaction vessels (nitration reactors) for carrying out nitration reactions, especially for the production of aliphatic or alicyclic nitrates (nitrates) from mono- or poly-aliphatic or alicyclic alcohols, preferably by adiabatic or isothermal nitration. (ii) in Figure 1 Not shown in the diagram, arranged downstream of the production line and / or connected to the nitration unit P. NE Downstream separation equipment, especially separators, is particularly used to separate residual nitrated acid from crude nitration products (crude nitrate esters); (iii) Located downstream of the production line and / or connected to the nitration unit P NE and Figure 1 The washing equipment W downstream of the separation equipment (not shown) is used to wash with a washing medium the products obtained from the production process and / or from the production equipment P. NE Crude nitrate NE crude A downstream arrangement and / or connection to a separation device is used to separate the washing medium from the washed crude nitrate NE. wet Separation; (iv) A purification and / or drying device K, particularly a column, arranged downstream of the production line and / or connected downstream of the washing equipment W, for drying and / or purifying, in particular drying and purifying, the washed crude nitrate NE obtained from the washing equipment W. wet , (v) A recovery unit T located downstream of the production line and / or connected to the downstream of the purification and / or drying equipment K (especially the column) for recovering and / or circulating inert gas TG. dry TG wet .

[0205] The purification and / or drying equipment K includes a first inlet device 2, which is specifically located in the upper region KK of the purification and / or drying equipment, particularly at the top of the column, for introducing the washed crude nitrate NE. wetThe gas is introduced and / or fed into the purification and / or drying equipment K. Similarly, the purification and / or drying equipment K also includes a second inlet device 3, which is specifically located in the lower region KS of the purification and / or drying equipment K, particularly at the bottom of the column, for introducing the dried inert gas TG. dry Introduced and / or fed into purification and / or drying equipment K.

[0206] In addition, the purification and / or drying equipment K also includes a method for treating the washed crude nitrate NE wet With dry inert gas TG dry The equipment (means) for contact (especially for flow), particularly the equipment for contact (especially for flow), is designed in such a way that the washed crude nitrate NE wet The water present in the nitrate is removed (i.e., the crude nitrate ester after washing is dried), while and / or volatile and / or volatile impurities generated, particularly during nitrate ester production and / or washing, are removed in the same manner, thereby obtaining dried (pre-dried) nitrate ester NE that is particularly free of volatile impurities. dry It is located downstream of the process direction and / or connected downstream of the purification and / or drying equipment K.

[0207] Furthermore, recovery equipment T is provided, comprising separation devices for separating water and / or moisture, as well as particularly volatile impurities, especially condensers and / or gas scrubbers or combinations thereof. These separation devices are specifically designed in such a way that, particularly by condensation and / or scrubbing (preferably condensation and scrubbing), the wet inert gas TG is separated. wet Water and / or moisture, as well as particularly volatile impurities, are separated from the gas, while a dry (pre-dried) inert gas TG free of particularly volatile impurities is obtained. dry .

[0208] In this regard, preferably, the recovery device T further includes a third inlet device 5, which is specifically located between the upper region KK (particularly the column top) of the purification and / or drying device K and the recovery device T, for introducing wet inert gas TG from the purification and / or drying device K, particularly containing water and / or particularly volatile impurities. wet Introduced and / or supplied and / or conveyed to the recycling equipment T.

[0209] according to Figure 1 The preferred production apparatus shown and / or the preferred apparatus contained therein for drying and / or purifying aliphatic or alicyclic nitrates are designed to perform a method comprising the following method steps, and / or particularly corresponding to the method of the present invention and comprising the following method steps: (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. (b) Subsequently, the washed crude nitrate ester obtained in step (a) is dried and / or purified, preferably dried and purified, by contacting it with an inert gas, particularly by passing it through a gas, in such a way as to remove water present in the washed crude nitrate ester (i.e. the washed crude nitrate ester is dried), while and / or in the same way to remove volatile and / or volatile impurities generated particularly during the production and / or washing of the nitrate ester.

[0210] The production of crude nitrate is preferably carried out by adiabatic or isothermal nitration, and / or the production process of crude nitrate preferably includes adiabatic or isothermal nitration or adiabatic or isothermal nitration. Particularly preferably, nitration is carried out according to the description in EP1792891A1, and / or in a suitable apparatus according to the description in EP1792891A1, the contents of which are hereby expressly referenced and are incorporated herein by reference in their entirety.

[0211] Crude nitrate NE obtained during the production process crude Subsequently passed Figure 1 The separation device (not shown) is fed into the washing device W for washing the crude nitrate NE. crude In this regard, the initial inlet device 1 is used to process the obtained crude nitrate NE. crude Introduced and / or fed into washing equipment W.

[0212] The nitrate ester used according to the invention is preferably a liquid under standard conditions, particularly at a pressure of 1.013 bar and 0% relative humidity (according to standard conditions STPD of DIN 1343), and / or exists in liquid form. For further details, please refer to the above description.

[0213] Nitrate esters are particularly preferred to be nitrate esters of mono- or poly-alliphatic or alicyclic alcohols, and / or said nitrate esters are selected from (i) nitrate esters of aliphatic or alicyclic alkanols, especially nitrate esters of straight-chain or branched aliphatic or alicyclic alkanols, preferably nitrate esters of hexanol, heptanol, octanol, ethylhexyl alcohol and cyclohexanol; (ii) nitrate esters of aliphatic alkyl glycols, especially nitrate esters of ethylene glycol and propylene glycol and their oligomers and polymers (such as ethylene glycol or propylene glycol, ethylene or propylene triethylene glycol and polyethylene glycol or polypropylene glycol); (iii) nitrate esters of aliphatic alkyltriols, especially nitrate esters of trimethylolethane, trimethylolpropane, glycerol and glycerol; and (iv) nitrate esters of tetra- or poly-alliphatic alkanols.

[0214] Volatile and / or volatile impurities are preferably selected from the group consisting of: (i) unreacted and / or partially reacted starting materials and / or starting reagents; (ii) nitration and non-nitration reaction byproducts; (iii) degradation and oxidation products of nitration products and byproducts; (iv) inorganic acids, particularly sulfuric acid, nitric acid and nitrous acid, preferably nitric acid; (v) organic acids, particularly formic acid, acetic acid, oxalic acid, carbonic acid and hydrocyanic acid; (vi) nitrogen-containing bases, particularly ammonia (NH3); (vii) nitrogen oxides, particularly nitric oxide (NO), nitrogen dioxide (NO2) and nitrous oxide (N2O), as well as nitrous oxide and other nitrogen oxides (NO3). x (viii) Carbon oxides, particularly carbon monoxide (CO) and carbon dioxide (CO2); (ix) Solvent and / or washing medium residues.

[0215] Similarly, the volatile impurities and / or volatile precipitates to be removed preferably have higher volatility than the nitrate ester to be purified, particularly higher vapor pressure and / or lower boiling point, especially based on the vapor pressure of the nitrate ester under standard conditions (pressure of 1.013 bar; atmospheric humidity of 0% [standard conditions STPD according to DIN 1343]) and / or particularly based on the boiling point of the nitrate ester under standard conditions (pressure of 1.013 bar; atmospheric humidity of 0% [standard conditions STPD according to DIN 1343]); specifically, the volatile and / or volatile precipitates to be removed preferably have a vapor pressure at least 5 mbar higher than the nitrate ester to be purified, preferably at least 7.5 mbar, more preferably at least 10 mbar, and / or the volatile and / or volatile precipitates to be removed preferably have a boiling point at least 1°C lower than the nitrate ester to be purified, preferably at least 2.5°C, more preferably at least 5°C lower.

[0216] exist Figure 1 Within the preferred embodiment of the apparatus and / or production apparatus shown, regarding the method according to the invention, method step (a) and / or washing are performed by liquid-liquid extraction.

[0217] Method step (a) preferably includes acidic, alkaline (alkali-containing) and / or neutral washing, particularly at least one alkaline (alkali-containing) and / or neutral washing, preferably acidic, alkaline (alkali-containing) and neutral washing.

[0218] Also preferably, method step (a) and / or washing are performed in one or more washing stages, more preferably in one, two, or three washing stages, and even more preferably in two or three washing stages; in particular, each washing stage includes one or more washing and / or extraction cycles. Also preferably, method step (a) and / or washing are performed using an aqueous washing medium; in particular, the aqueous washing medium is set to neutral, acidic, or alkaline (containing alkali). Furthermore, method step (a) and / or washing are preferably performed in at least two, particularly three, washing stages, particularly washing stages including at least one alkaline (containing alkali) washing stage and a final neutral washing stage, preferably washing stages including a first acidic washing stage, a subsequent second alkaline (containing alkali) washing stage, and a final third neutral washing stage.

[0219] In this sense, based on Figure 1 Within the scope of preferred embodiments of the production apparatus and / or device of the present invention, the washing equipment W is designed as a liquid-liquid extraction device.

[0220] Preferably, the washing apparatus W includes an acidic washing stage, an alkaline (alkali-containing) washing stage, and / or a neutral washing stage, particularly at least one alkaline (alkali-containing) washing stage and / or a neutral washing stage, preferably acidic, alkaline (alkali-containing), and neutral washing stages. Furthermore, it is preferred that the washing apparatus W includes one or more washing stages, preferably one, two, or three washing stages, more preferably two or three washing stages; specifically, each washing stage is designed such that it includes one or more washing and / or extraction cycles. Furthermore, it is preferred that the washing apparatus W is designed such that washing is performed using a water-based washing medium; in particular, the water-based washing medium is set to neutral, acidic, or alkaline (alkali-containing).

[0221] Furthermore, it has proven advantageous for the method of the present invention that, in method step (a), method step (a) and / or washing are carried out, particularly in each washing stage, in a cross-flow or counter-flow or a combination of cross-flow and counter-flow, and preferably the washing medium is recovered.

[0222] In this respect, the washing equipment W is advantageously designed in such a way that, particularly in each washing stage, washing is carried out in a cross-flow or counter-flow or a combination of cross-flow and counter-flow, preferably with the washing medium being recovered. In this case, the washing equipment W is particularly operable in each washing stage, preferably operating in a cross-flow or counter-flow or a combination of cross-flow and counter-flow, and / or can be operated accordingly, preferably with the washing medium being recovered.

[0223] At the end of method step (a), for those based on Figure 1The production apparatus and / or equipment provided are such that, in method step (a), the separation of the washing medium is carried out by separation equipment (separator), particularly by static separation equipment or centrifugal separator. In this sense, the connection to Figure 1 The downstream separation equipment of the washing equipment is designed as a separation device (separator), especially a static separation device or a centrifugal separator.

[0224] The subsequent method step (b) is carried out in a drying and / or purification apparatus K. The purification and / or drying apparatus K includes and / or particularly includes columns.

[0225] The latter preferably includes single-stage or multi-stage columns, particularly packed bed columns, sieve plate columns, bubble cap disk columns, or falling film columns, or combinations thereof. Alternatively, the purification and / or drying equipment K includes and / or a gas / liquid reactor or stripping equipment.

[0226] The washed crude nitrate obtained in step (a) is transferred in step (b) according to... Figure 1 In the production apparatus and / or the drying and / or purification equipment K of the apparatus. For the purpose of transferring nitrate esters, a first inlet device 2 is provided, designed as a connection between the washing apparatus W and the purification and / or drying equipment K, and / or the first inlet device 2 is designed as a conveying line, particularly designed as a conveying line for connecting the washing apparatus W and the purification and / or drying equipment K.

[0227] Similarly, it has proven advantageous for an additional inlet device (in particular, the second inlet device 3) to be designed for drying inert gas TG. dry The storage device is connected to the purification and / or drying equipment K, and / or the second inlet device 3 is designed as a delivery line, particularly designed for connecting the dry inert gas TG. dry The storage device and the delivery pipeline of the purification and / or drying equipment K.

[0228] For the third inlet device 5, similarly preferred, the third inlet device 5 is designed as a connection between the purification and / or drying device K and the recovery device T, and / or wherein the third inlet device 5 is designed as a delivery line, particularly as a delivery line for connecting the purification and / or drying device K and the recovery device T.

[0229] Furthermore, it has proven advantageous that, in method step (b), drying and / or purification, preferably drying and purification, be carried out as a continuous or discontinuous, particularly continuous, process. Figure 1Within this range, the method is designed as a continuous process. Therefore, the purification and / or drying equipment K, particularly a column, is designed such that drying and / or purification, preferably drying and purification, is carried out as a continuous or discontinuous, particularly continuous process. For this purpose, the purification and / or drying equipment K is preferably designed as a gas-liquid extraction device and / or a desorption device, particularly a gas-liquid extraction device. Furthermore, the apparatus and / or production apparatus according to the invention can use the preferred inlet devices 2, 3, and 5 as described above.

[0230] The washed crude nitrate ester obtained in step (a) is contacted with an inert gas, particularly during the flow, according to... Figure 1 The production process is carried out in a cross-flow and / or counter-flow manner, preferably counter-flow, within the production apparatus and / or device. Furthermore, for the method of the present invention, in step (b), drying and / or purification, preferably drying and purification, is carried out as gas-liquid extraction and / or by desorption, particularly as gas-liquid extraction. In this respect, it has proven advantageous that the inert gas is directed to flow upwards and the nitrate ester is directed to flow downwards.

[0231] Furthermore, good results can be obtained if, in step (b), the contact between the nitrate ester and the inert gas, particularly the flow of the gas, occurs and / or is carried out with the inert gas dispersed, particularly finely dispersed, in the nitrate ester. It is particularly advantageous that, in step (b), the inert gas is introduced into the nitrate ester using and / or in a dispersed, particularly finely dispersed, distribution. For this purpose, the apparatus and / or production equipment advantageously includes nozzles, jet mixers, jet pumps, syringes, spray guns, sieve plates, and / or microporous membranes, preferably nozzles, jet mixers, and / or microporous membranes.

[0232] Furthermore, in step (b) of the method, the inert gas is used in a dry form.

[0233] According to the described embodiments of the method, the apparatus and / or production apparatus according to the invention can provide a purification and / or drying device K, particularly for processing washed crude nitrate NE. wet With dry inert gas TG dry The equipment in contact, especially the equipment used for flow, is designed in such a way that the washed crude nitrate NE obtained from the washing equipment W... wet With dry inert air TG dry Contact, especially flow, is carried out in a cross-flow and / or counter-flow manner, preferably counter-flow.

[0234] Specifically, purification and / or drying equipment K is available, particularly for treating washed crude nitrate NE. wet With dry inert gas TG dryContact, especially flow-through equipment, is designed in this way to allow the dry inert gas TG to be effectively handled. dry Guided to flow upwards, the washed crude nitrate NE wet It is guided to flow downwards.

[0235] also, Figure 1 The production apparatus and / or equipment are designed in such a way that the dried and / or purified, preferably dried and purified, nitrate obtained after method step (b) can be obtained and / or collected separately and / or separately from the inert gas.

[0236] Advantageously, no additional separation steps are performed and / or required to separate the dried and / or purified, preferably dried and purified, nitrate obtained after method step (b) from the inert gas.

[0237] Therefore, in the sense of continuous process execution, the apparatus according to the invention can provide a purification and / or drying device K, particularly a column, including an outlet and / or discharge device 4, which is particularly arranged in the lower region KS, preferably the bottom of the column, for drying (dried) nitrate ester NE, particularly free of volatile impurities. dry .

[0238] Advantageously, the outlet and / or discharge device 4 is designed in this respect as a purification and / or drying device K with a dry (dried) nitrate ester NE specifically free of volatile impurities. dry The collection and / or storage equipment, and / or outlet and / or discharge equipment 4 are designed as delivery pipelines, particularly as connections to purification and / or drying equipment K and for drying (dried) nitrate esters NE that are particularly free of volatile impurities. dry Delivery lines for collection and / or storage equipment.

[0239] According to Figure 1 In the apparatus and / or production unit, in method step (b), the washed crude nitrate obtained in method step (a) is used as is and / or in concentrated and / or undiluted form. Therefore, in this sense, it is preferably provided that in method step (b), no (additional) solvent and / or dispersant is added to the washed crude nitrate obtained in step (a) for drying and / or purification, preferably drying and purification.

[0240] In addition, according to Figure 1 The apparatus and / or production apparatus are designed in such a way that, in method step (b), the inert gas is selected and / or designed in such a way that, under the conditions of method step (b), the inert gas does not react with respect to the nitrate ester.

[0241] In this regard, it has proven advantageous that, in step (b) of the method, the inert gas is selected from nitrogen, oxygen, rare gases (especially argon), hydrogen, carbon oxides and mixtures thereof (especially air), preferably from nitrogen, oxygen, rare gases (especially argon) and mixtures thereof (especially air), and particularly preferably from nitrogen, oxygen and mixtures thereof (especially air).

[0242] According to Figure 1 Within the scope of the preferred embodiment of the method according to the invention, it is also provided to recover and / or recycle the inert gas after method step (b). This step is performed after and / or simultaneously with the drying and purification of the inert gas. Therefore, the inert gas after method step (b) is subjected to drying and purification treatment, particularly by means of a condenser and / or a gas scrubber or a combination thereof. In this regard, as described above, the inlet device 5 is preferably used as a conveying device to feed the wet inert gas from the purification and / or drying device K into the recovery device T.

[0243] In this sense, according to Figure 1 Within the scope of embodiments of the method of the present invention, it is also provided that the inert gas obtained and / or separated after method step (b), particularly the inert gas loaded with water and / or moisture and particularly volatile impurities, is transferred to the recovery device T for gas treatment.

[0244] Particularly advantageously, the recovery equipment T includes and / or a condenser and / or a gas scrubber or a combination thereof, especially a condenser.

[0245] In particular, it has proven advantageous for the recovery device T to be designed as a condenser, which includes a refrigerant, a coolant (especially chilled water and / or cooling water) and / or a cooling gas (especially chilled air and / or cooling air), especially for cooling the recovery device T in which inert gas treatment is carried out.

[0246] A temperature gradient exists between the drying and / or purification equipment K and the recovery equipment T. The temperature gradient is specifically designed so that the temperature set in the recovery equipment T is lower than the temperature provided in the drying and / or purification equipment K.

[0247] Therefore, it is preferable to have a temperature gradient that decreases along the process direction from the drying and / or purification equipment K to the recovery equipment T.

[0248] In addition, for Figure 1 The apparatus or production unit provided in the document is a recovery device T comprising two emission devices 6 and 7, for the particularly dry (dried) inert gas TG, which is free of volatile impurities. dry And / or water and / or moisture from inert gas treatment, and / or having particularly wet inert gas TG wet The washing liquid contains volatile impurities.

[0249] according to Figure 1 The emission device 6 is designed as an indirect connection between the recovery device T and the purification and / or drying device K, particularly through the second inlet device 3. However, a direct design of the emission device 6 is equally feasible.

[0250] Specifically, in this case, emission device 6 is designed for use with dry (pre-dried) inert gas TG that is particularly free of volatile impurities. dry The pipeline is preferably designed for use with dry (pre-dried) inert gas TG, which is particularly free of volatile impurities. dry The delivery pipeline, and Figure 1 In this context, the design of the recovery device T and the purification and / or drying device K, particularly through the indirect connection established via the second inlet device 3, specifically in such a manner that the inert gas TG is generated... dry TG wet Recycling and / or recycling.

[0251] exist Figure 1 Within this range, the emission device 7 is also designed as a connection between the recovery device T and the washing device W. Specifically, the emission device 7 is designed as a delivery pipeline for water and / or moisture from inert gas treatment, and / or for moisture from wet inert gas TG. wet The washing liquid contains volatile impurities. The discharge device 7 is specifically designed as a delivery line for water and / or moisture from the inert gas treatment and / or containing TG from the wet inert gas. wet The washing liquid contains volatile impurities, and the delivery line is used to connect the recovery device T and the washing device W, particularly in such a way that water and / or moisture from the gas treatment and / or substances particularly from the wet inert gas TG are generated. wet Recovery and / or recycling of washing liquid containing volatile impurities.

[0252] Regarding inert gases, in this case, the primary provision is that the inert gas is treated to separate water and / or moisture, as well as particularly volatile impurities, preferably by condensation and / or washing, and more preferably condensation and washing. Therefore, it has proven advantageous that the recovery device T for treating and recovering the gas includes a condenser and / or a gas scrubber, or a combination thereof.

[0253] Subsequently, the treated inert gas is then recovered into step (b) of the method, specifically by means of delivery via emission device 6.

[0254] For the condensate and / or washing medium obtained from the treatment of inert gases, it is also provided that they are recycled, particularly after preparation and / or purification. Specifically, the resulting condensate and / or washing medium are recovered into the washing process of step (a) of method and / or transported via discharge device 7.

[0255] When reading the specification, those skilled in the art can readily identify and implement further improvements, modifications, variations, and advantages of the invention without departing from its scope.

[0256] The invention is further illustrated by the following examples, but is not limited thereto.

[0257] List of reference numerals in the attached diagram: P NE Nitrification equipment NE crude Crude nitrate W washing equipment NE wet Crude nitrate after washing K. Purification and / or drying equipment Upper area of ​​KK purification and / or drying equipment Lower area of ​​KS purification and / or drying equipment T recycling equipment NE dry Dry and / or dried nitrates free of, in particular, volatile impurities. TG dry Dry and / or dried inert gases free from, in particular, volatile impurities. TG wet Moist inert gases containing, in particular, volatile impurities 1. Inlet equipment for processing the obtained crude nitrate NE crude Introduced and / or supplied to washing equipment W 2. Inlet equipment, used to process the washed crude nitrate ester NE wet Introduced and / or supplied to purification and / or drying equipment K 3. Inlet device for introducing dry inert gas TG dry Introduced and / or supplied to purification and / or drying equipment K 4. Emission equipment for dried (dried) nitrate esters (NE) free from particularly volatile impurities. dry 5. Inlet device for introducing wet inert gas TG, particularly loaded with water and / or particularly volatile impurities. wet Introduced and / or supplied and / or conveyed from purification and / or drying equipment K to recycling equipment T 6. Emission equipment for dry (dried) inert gas TG that does not contain, in particular, volatile impurities. dry 7. Emission equipment for water and / or moisture from inert gas treatment and / or particularly for wet inert gas TG. wet Washing liquid containing volatile impurities Example 1. Purification and drying of 2-ethylhexyl nitrate by the method of the present invention. 1000 mL of 2-ethylhexyl nitrate (EHN) was produced using the conventional production method of nitrates according to Example 1 of EP1792891A1.

[0258] Subsequently, the crude nitrate ester obtained in this manner is dried and purified according to the invention to remove water and / or moisture generated during the production and washing of the nitrate ester, as well as volatile and / or volatile impurities, wherein the apparatus according to the invention is used, and the method following the invention is illustrated with reference to a single figure, as described in detail above.

[0259] Therefore, after the final nitrated acid is separated, the crude nitrate ester produced is washed at approximately 30°C in a washing apparatus designed with multiple stages (three stages: acidic washing, followed by alkaline and / or alkaline washing, and finally neutral washing with an aqueous washing medium). The crude nitrate ester still contains a large amount of water and / or moisture generated during the nitrate ester production and washing process, as well as volatile and / or volatile impurities. The crude nitrate ester is separated from the washing medium at each stage.

[0260] The washed crude nitrate ester had a water content of 0.056% (by weight), and exhibited significant turbidity upon cooling due to this water content. Furthermore, the washed crude nitrate ester contained various volatile and / or volatile impurities (CO2 31 ppm; NO and NO2 15 ppm; HNO3 10 ppm; NH3 120 ppm; volatile organic compounds (such as formic acid) 13 ppm). Therefore, prior to implementing the method of the present invention, the total content of volatile and / or volatile impurities was 189 ppm.

[0261] The washed crude nitrate is transferred to the purification and drying apparatus according to the invention (a column with a column bottom and a column top as illustrated in the single figure; dry inert gas is supplied through the column bottom and crude nitrate is supplied through the column top via respective inlet lines), through which dry inert gas in the form of dry air (dew point about -40°C) at a rate of 400 L / h flows through a microporous ceramic membrane (countercurrent; finely dispersed airflow).

[0262] The temperature in the purification and drying equipment is approximately 20°C, and the pressure in the equipment corresponds to atmospheric pressure. Based on 1 ton of nitrate ester to be purified, and calculated under standard conditions (pressure: 1.013 bar; atmospheric humidity: 0%, i.e., dry inert gas; temperature: 0°C [according to standard conditions STPD of DIN 1343]), the volume of inert gas used is approximately 50 standard cubic meters.

[0263] The water content of the crude nitrate washed with an initial concentration of 0.056% (by weight) before the introduction of inert gas was checked after 1 minute, 2 minutes, 5 minutes, and 10 minutes.

[0264] After the nitrate ester to be purified and / or dried is passed through for 1 minute, the water content is 0.045%, 0.030% after 2 minutes, 0.018% after 5 minutes, and 0.003% after 10 minutes. Due to the production process, EHN is initially turbid, but after only one minute of treatment, EHN will further clarify into a completely clear liquid, which will also remain completely clear in further processes of the method.

[0265] In contrast, conventionally produced 2-ethylhexyl nitrate purified using existing technology typically contains about 0.05% water.

[0266] Therefore, within the scope of the method of the present invention and / or by means of the drying and purification equipment of the present invention, significantly less water-rich and / or anhydrous and purer nitrates can be provided compared with prior art and / or conventional production and purification methods and equipment.

[0267] The content of volatile and / or volatile impurities in the EHN obtained from the method of the present invention was further analyzed. In this regard, it has been confirmed that, within the detection range, the obtained dried and purified EHN is virtually free of unwanted impurities and / or accompanying substances. Specifically, the content of the following impurities can be minimized: CO2 from 31 ppm to 1 ppm; NO and NO2 from 15 ppm to less than 1 ppm; HNO3 from 10 ppm to 2 ppm; NH3 from 120 ppm to less than 1 ppm; and volatile organic compounds (e.g., formic acid) from 13 ppm to 2 ppm.

[0268] Therefore, in addition to significantly reducing water content, the method of the present invention can also achieve a broad reduction in volatile and / or volatile impurities that can be introduced into crude nitrate ester during the production process.

[0269] Furthermore, the process is controlled in such a way that the vapor pressure of the nitrate ester remains consistently low, thus preventing the formation of an explosive mixture of nitrate ester vapor and gas at any time. Therefore, in addition to being highly efficient, this provides a very reliable method.

[0270] In this method, an inert gas in the form of air, which absorbs water and / or moisture as well as volatile and / or permeable impurities from the product, is introduced from the purification and drying equipment via appropriate inlets and / or delivery lines into a recovery unit equipped with a gas scrubber and a condenser. The gas scrubber removes the volatile and / or permeable impurities, and the condenser removes water by condensation. The dried air obtained in this manner is then reused to dry the scrubbed crude nitrate ester and / or recycled (recovered).

[0271] The obtained condensate, along with trace amounts of EHN carried and separated unwanted byproducts, is recycled to a washing unit connected upstream of the purification and drying equipment, where it is absorbed and / or neutralized in the process of this invention.

[0272] The steps according to the invention are particularly advantageous and economical in terms of method: the air and / or inert gas used for drying and purification are circulated in a (closed) loop according to the invention. Thus, no environmental or exhaust gas pollution occurs. The condensate obtained in the condenser where the conveying water is collected can be recovered without problem into the production process (product washing), especially even if it contains a small amount of product (EHN); thereby reducing and / or avoiding undue EHN loss.

[0273] The procedure was repeated using other inert gases (nitrogen and argon). Comparable results were obtained.

[0274] 2. The method of the present invention is used to purify and dry amyl nitrate (pentyl nitrate). According to the method of the present invention for EHN described above, crude amyl nitrate (pentyl nitrate) was also purified and dried in a corresponding manner. Comparable results were obtained.

[0275] 3. Comparative Example: Treatment of 2-ethylhexyl nitrate according to existing technology 1000 mL of 2-ethylhexyl nitrate (EHN) was produced using a conventional production method of nitrates according to Example 1 of EP1792891A1.

[0276] After separating the final nitrate acid according to Example 1, the crude nitrate ester was washed at approximately 30°C and separated from the washing medium. The obtained washed crude nitrate ester was passed at a rate of 20 mL / min through a cooling device consisting of a 2 m long, 3 mm inner diameter stainless steel pipeline arranged in a constant temperature bath controlled at -5°C. Visibly dispersed water droplets were observed in the storage container collecting the washed and cooled EHN ester. These droplets were separated by a coalescer made of stainless steel fabric.

[0277] The initial water content of the washed crude nitrate ester was 0.056%. After cooling and drying using a coalescer, the water content of the nitrate ester obtained from this process remained at 0.028%. Therefore, the cloud point of EHN nitrate ester dried in this manner upon cooling can only be reduced to approximately 11°C.

[0278] Compared to the method of the present invention, a less dry product is thus obtained, which also has a relatively high cloud point. That is, in cold regions, water crystallization may occur during the transport of the corresponding ester, which may have a negative impact on product quality.

[0279] Furthermore, due to the required strong cooling, the method according to the comparative example is significantly more energy-intensive and less efficient.

[0280] Compared to the method according to the invention, the separate and downstream but necessary water separation via the coalescer also constitutes an additional complex working step (in contrast, the invention is significantly more efficient and effective).

[0281] Compared with the method according to the present invention, the content of volatile and / or volatile impurities cannot be significantly reduced (after performing the method of Example 3, the total content of volatile and / or volatile impurities is >160ppm).

Claims

1. A method for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrates (nitrates), particularly for removing water and volatile impurities generated especially during the production and / or washing of nitrates. This method includes the following steps: (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. (b) Subsequently, the washed crude nitrate ester obtained in step (a) is dried and / or purified, preferably dried and purified, by contact with an inert gas, particularly by flow (permeation), in such a way that water present in the washed crude nitrate ester is removed, and / or volatile impurities generated particularly during the production and / or washing of the nitrate ester are removed in the same manner.

2. The method according to claim 1, The nitrate esters thereon are liquid under standard conditions, particularly at a pressure of 1.013 bar and 0% relative humidity (according to the standard conditions of DIN 1343, STPD), and / or exist in liquid form; and / or The nitrate esters mentioned above are nitrate esters of mono- or poly-aliphatic or alicyclic alcohols; and / or The nitrate esters mentioned therein are selected from: (i) nitrate esters of aliphatic or alicyclic alkanols, particularly nitrate esters of straight-chain or branched aliphatic or alicyclic alkanols, preferably nitrate esters of hexanol, heptanol, octanol, ethylhexyl alcohol and cyclohexanol; (ii) nitrate esters of aliphatic alkyl glycols, particularly nitrate esters of ethylene glycol and propylene glycol and their oligomers and polymers, such as nitrate esters of ethylene glycol or propylene glycol, ethylene or propylene triethylene glycol and polyethylene glycol or polypropylene glycol; (iii) nitrate esters of aliphatic alkyltriols, particularly nitrate esters of trimethylolethane, trimethylolpropane, glycerol and glycerol; and (iv) nitrate esters of quaternary or polyaliphatic alkanols.

3. The method according to claim 1 or 2, The volatile impurities mentioned herein are selected from: (i) unreacted and / or partially reacted starting materials and / or starting reagents; (ii) nitration and unnitration reaction byproducts; (iii) degradation and oxidation products of nitration products and byproducts; (iv) inorganic acids, particularly sulfuric acid, nitric acid and nitrous acid, preferably nitric acid; (v) organic acids, particularly formic acid, acetic acid, oxalic acid, carbonic acid and hydrocyanic acid; (vi) nitrogen-containing bases, particularly ammonia (NH3); (vii) nitrogen oxides, particularly nitric oxide (NO), nitrogen dioxide (NO2) and nitrous oxide (N2O), as well as nitrite and other nitrogen oxides (NO3). x (viii) Carbon oxides, particularly carbon monoxide (CO) and carbon dioxide (CO2); (ix) Solvent and / or washing media residues; and / or in, The volatile impurity to be removed has higher volatility than the nitrate ester to be purified, particularly higher vapor pressure and / or lower boiling point, especially based on the vapor pressure of the nitrate ester under standard conditions (pressure 1.013 bar; atmospheric humidity 0% [standard conditions according to DIN 1343, STPD]) and / or particularly based on the boiling point of the nitrate ester under standard conditions (pressure 1.013 bar; atmospheric humidity 0% [standard conditions according to DIN 1343, STPD]); particularly wherein the vapor pressure of the volatile impurity to be removed is at least 5 mbar higher than that of the nitrate ester to be purified, preferably at least 7.5 mbar higher, more preferably at least 10 mbar higher, and / or particularly wherein the boiling point of the volatile impurity to be removed is at least 1°C lower than that of the nitrate ester to be purified, preferably at least 2.5°C lower, more preferably at least 5°C lower.

4. The method according to any one of the preceding claims, Wherein method step (a) and / or washing are performed as liquid-liquid extraction; and / or Method step (a) includes acidic, alkaline (alkali-containing) and / or neutral washing, particularly at least one alkaline (alkali-containing) and / or neutral washing, preferably acidic, alkaline (alkali-containing) and neutral washing; and / or The method step (a) and / or washing are performed in one or more washing stages, preferably in one, two, or three washing stages, more preferably in two or three washing stages; in particular, each washing stage includes one or more washing and / or extraction cycles (steps); and / or The method step (a) and / or washing are performed using a water-based washing medium; in particular, the water-based washing medium is set to be neutral, acidic, or alkaline (containing alkali).

5. The method according to any one of the preceding claims, The method step (a) and / or washing are performed in at least two, particularly three washing stages, wherein the washing stages include at least one alkaline (alkali-containing) washing stage and a final neutral washing stage, preferably wherein the washing stages include a first acidic washing stage, a subsequent second alkaline (alkali-containing) washing stage and a final third neutral washing stage.

6. The method according to any one of the preceding claims, The method steps (a) and / or washing, particularly in each washing stage, are carried out in a cross-flow or counter-flow or a combination of cross-flow and counter-flow, preferably with the recovery of the washing medium.

7. The method according to any one of the preceding claims, In step (a) of the method, the separation of the washing medium is carried out by a separation device (separator), particularly by a static separation device or a centrifugal separator.

8. The method according to any one of the preceding claims, Method step (b) is carried out in a drying and / or purification apparatus, preferably a drying and purification apparatus; In particular, the washed crude nitrate obtained in step (a) is transferred in step (b) to a drying and / or purification apparatus, preferably a drying and purification apparatus; and / or In particular, the drying and / or purification equipment, preferably including columns and / or gas / liquid reactors or stripping equipment, and preferably columns, especially single-stage or multi-stage columns, preferably packed bed columns, sieve plate columns, bubble cap disc columns or falling film columns or combinations thereof.

9. The method according to any one of the preceding claims, In method step (b), drying and / or purification, preferably drying and purification, are carried out as a continuous or discontinuous, particularly continuous process.

10. The method according to any one of the preceding claims, In method step (b), drying and / or purification, preferably drying and purification, are carried out as gas-liquid extraction and / or by desorption, particularly as gas-liquid extraction.

11. A method for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrates (nitrates), particularly for removing water and volatile and / or permeable impurities generated during the production and / or washing of nitrates, especially the method according to any one of the preceding claims. This method includes the following steps: (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. The method steps (a) and / or washing are performed as liquid-liquid extraction; (b) Subsequently, the washed crude nitrate ester obtained in step (a) is dried and / or purified, preferably dried and purified, by contact with an inert gas, particularly by flow (permeation), in such a manner as to remove water present in the washed crude nitrate ester, and simultaneously and / or in the same manner to remove volatile and / or permeable impurities generated particularly during the production and / or washing of the nitrate ester. Drying and / or purification, preferably drying and purification, are carried out as gas-liquid extraction and / or by desorption, especially as gas-liquid extraction; In particular, the volatile and / or volatile impurities are selected from the group consisting of: (i) unreacted and / or partially reacted starting materials and / or starting reagents; (ii) nitration and non-nitration reaction byproducts; (iii) degradation and oxidation products of nitration products and byproducts; (iv) inorganic acids, especially sulfuric acid, nitric acid and nitrous acid, preferably nitric acid; (v) organic acids, especially formic acid, acetic acid, oxalic acid, carbonic acid and hydrocyanic acid; (vi) nitrogen-containing bases, especially ammonia (NH3); (vii) nitrogen oxides, especially nitric oxide (NO), nitrogen dioxide (NO2) and nitrous oxide (N2O), as well as nitrite and other nitrogen oxides (NO3). x (viii) Carbon oxides, particularly carbon monoxide (CO) and carbon dioxide (CO2); (ix) Solvent and / or washing media residues; and / or In particular, the volatile and / or volatile impurities to be removed have higher volatility than the nitrate esters to be purified, especially higher vapor pressure and / or lower boiling point, particularly based on the vapor pressure of the nitrate esters under standard conditions (pressure 1.013 bar; atmospheric humidity 0% [standard conditions according to DIN 1343, STPD]) and / or particularly based on the boiling point of the nitrate esters under standard conditions (pressure 1.013 bar; atmospheric humidity 0% [standard conditions according to DIN 1343, STPD]).

12. The method according to any one of the preceding claims, In method step (b), the washed crude nitrate ester obtained in method step (a) is used directly; and / or in method step (b), the washed crude nitrate ester obtained in step (a) is used in concentrated or undiluted form; and / or In step (b), no additional solvent and / or dispersant for drying and / or purification, preferably drying and purification, is added to the washed crude nitrate obtained in step (a).

13. The method according to any one of the preceding claims, In step (b), an inert gas is selected and / or formed in such a manner that it does not react with respect to the nitrate ester under the conditions of step (b); and / or In step (b) of the method, the inert gas is selected from nitrogen, oxygen, rare gases, especially argon, hydrogen, carbon oxides and especially air, preferably from nitrogen, oxygen, rare gases, especially argon and especially air, and particularly preferably from nitrogen, oxygen and especially air.

14. The method according to any one of the preceding claims, In step (b) of the method, the contact between the washed crude nitrate ester obtained in step (a) and the inert gas, particularly the flow, is carried out in a cross-flow and / or counter-flow manner, preferably counter-flow. In particular, the inert gas is guided to flow upward and the nitrate ester is guided to flow downward; especially in drying and / or purification equipment, preferably drying and purification equipment, more preferably columns, especially single-stage or multi-stage columns, preferably packed bed columns, sieve plate columns, bubble cap disk columns or falling film columns or combinations thereof, and / or in gas / liquid reactors or stripping devices.

15. The method according to any one of the preceding claims, In method step (b), the contact between the nitrate ester and the inert gas, particularly the flow of the gas, occurs and / or proceeds in a manner that the inert gas is dispersed, particularly finely dispersed, within the nitrate ester; and / or In step (b) of the method, the inert gas is preferably introduced into the nitrate ester by means of a nozzle, jet mixer, jet pump, syringe, spray gun, sieve plate and / or microporous membrane, more preferably by means of a nozzle, jet mixer and / or microporous membrane, using and / or employing a dispersed distribution, especially a finely dispersed distribution.

16. The method according to any one of the preceding claims, In step (b) of the method, the inert gas is used in a dry form; In particular, the dew point of the inert gas in its dry form is lower than the temperature at which step (b) of the method of the present invention is performed; in particular, the dew point is preferably at least 5°C lower than the temperature at which step (b) of the method of the present invention is performed, more preferably at least 10°C, and most preferably at least 15°C lower; and / or In particular, In particular, the dew point of the inert gas supplied and / or initially supplied at the beginning of method step (b) is -20°C or lower, especially -30°C or lower, preferably -35°C or lower, more preferably -40°C or lower, and / or the dew point is -80°C or higher, especially -65°C or higher, preferably -55°C or higher, more preferably -50°C or higher; and / or In particular, the dew point of the inert gas supplied and / or initially supplied at the start of method step (b) is in the range of -20°C to -80°C, especially -30°C to -65°C, preferably -35°C to -55°C, more preferably -40°C to -50°C; and / or In particular, the relative humidity of the inert gas supplied and / or initially supplied at the beginning of method step (b) is in the range of 0 to 95%, particularly 0 to 90%, preferably 0 to 85%, more preferably 0 to 80%.

17. The method according to any one of the preceding claims, In method step (b), when drying and / or purification, preferably drying and purification and / or contact with an inert gas, particularly during flow, the volumetric flow rate of the inert gas is 100 L / h / kg nitrate (L / h / kg of nitrate to be dried and / or free of volatile impurities) or higher, particularly 200 L / h / kg nitrate or higher, preferably 300 L / h / kg nitrate or higher, more preferably 350 L / h / kg nitrate or higher, and / or the volumetric flow rate of the inert gas is 600 L / h / kg nitrated ester or lower, particularly 500 L / h / kg nitrate or lower, preferably 450 L / h / kg nitrate or lower, more preferably 425 L / h / kg nitrate or lower; and / or In step (b) of the method, when drying and / or purifying, preferably drying and purifying and / or contacting with an inert gas, particularly during flow, the volumetric flow rate of the inert gas is in the range of 100 L / h / kg nitrate to 600 L / h / kg nitrate, particularly 200 L / h / kg nitrate to 500 L / h / kg nitrate, preferably 300 L / h / kg nitrate to 450 L / h / kg nitrate, more preferably 350 L / h / kg nitrate to 425 L / h / kg nitrate.

18. The method according to any one of the preceding claims, In method step (b), when drying and / or purification, preferably drying and purification and / or contact with an inert gas, particularly during flow, the residence time of the nitrate ester in the presence of the inert gas is 30 seconds or longer, particularly 1 minute or longer, preferably 3 minutes or longer, more preferably 7 minutes or longer, and / or the residence time of the nitrate ester in the presence of the inert gas is 20 minutes or less, particularly 17 minutes or less, preferably 14 minutes or less, more preferably 12 minutes or less; and / or In step (b) of the method, when drying and / or purifying, preferably drying and purifying and / or contact with an inert gas, particularly during flow, the residence time of the nitrate ester in the presence of the inert gas is 30 seconds to 20 minutes, particularly 1 minute to 17 minutes, preferably 3 minutes to 14 minutes, and more preferably 7 minutes to 12 minutes.

19. The method according to any one of the preceding claims, In method step (b), the vapor pressure of the nitrate ester is less than 100 mbar, particularly less than 80 mbar, preferably less than 60 mbar, and more preferably less than 50 mbar, at the temperature during drying and / or purification, preferably drying and purification and / or contact with an inert gas, especially during flow. In method step (b), drying and / or purification are performed, preferably drying and purification and / or contact with an inert gas, particularly at a temperature above 0°C, particularly above 5°C, preferably above 7.5°C, more preferably above 10°C, and / or below 60°C, particularly below 50°C, preferably below 40°C, more preferably below 35°C; and / or In step (b) of the method, drying and / or purification are carried out, preferably drying and purification and / or contact with an inert gas, especially at a temperature of 0°C to 60°C, particularly 5°C to 50°C, preferably 7.5°C to 35°C, more preferably 10°C to 30°C.

20. The method according to any one of the preceding claims, In method step (b), drying and / or purification are carried out under atmospheric pressure (normal pressure; 1.01325 bar) or vacuum (reduced pressure) or ultra-atmospheric pressure, preferably under atmospheric pressure; preferably drying and purification and / or contact with an inert gas, especially through flow; and / or In step (b) of the method, drying and / or purification, preferably drying and purification and / or contact with an inert gas, particularly flow, is carried out at an absolute pressure of 0.1 bar to 3 bar, particularly 0.3 bar to 1.2 bar, preferably 0.5 bar to 1.1 bar, more preferably about 1 bar.

21. The method according to any one of the preceding claims, in, The amount of inert gas used in step (b) is selected and / or set based on the following: drying and / or purification conditions, particularly temperature and / or pressure and / or duration of drying and / or purification and / or type of inert gas; and / or content and / or type of impurities in the nitrate ester to be purified; and / or desired residual content of volatile impurities in the resulting purified nitrate ester; and / or The amount of inert gas used in step (b) is calculated based on 1 ton of nitrate ester to be purified, and is under standard conditions (pressure: 1.013 bar; atmospheric humidity: 0%, i.e., dry inert gas). Temperature: 0°C [according to standard conditions of DIN 1343, STPD]) calculated as the volume of inert gas in standard cubic meters, from 0.5 to 500 standard cubic meters, particularly 2 to 200 standard cubic meters, preferably 5 to 100 standard cubic meters, more preferably 8 to 70 standard cubic meters; and / or The amount of inert gas used in step (b) is calculated based on 1 ton of nitrate ester to be purified, and is under standard conditions (pressure: 1.013 bar; atmospheric humidity: 0%, i.e., dry inert gas). Temperature: 0°C [according to standard conditions of DIN 1343, STPD]) is calculated as the amount and / or weight of inert gas, from 1 to 250 kg, particularly from 2 to 140 kg, preferably from 5 to 50 kg, more preferably from 10 to 40 kg.

22. The method according to any one of the preceding claims, The water content of the dried and / or purified nitrate, preferably the dried and purified nitrate, is at most 0.06 wt%, particularly at most 0.03 wt%, preferably at most 0.02 wt%, and more preferably at most 0.01 wt%, based on nitrate ester; and / or The water content of the dried and / or purified nitrate, preferably the dried and purified nitrate, is in the range of 0.00001 to 0.06 wt%, particularly 0.0001 to 0.03 wt%, preferably 0.0005 to 0.02 wt%, and more preferably 0.0005 to 0.01 wt%, based on nitrate.

23. The method according to any one of the preceding claims, Wherein, after drying and / or purification, preferably after drying and purification, the content of volatile impurities in the nitrate ester is at most 100 ppm, particularly at most 30 ppm, preferably at most 25 ppm, more preferably at most 20 ppm, and even more preferably at most 10 ppm; and / or After drying and / or purification, preferably after drying and purification, the content of volatile impurities in the nitrate ester is in the range of 0.001 to 100 ppm, particularly 0.001 to 30 ppm, preferably 0.001 to 25 ppm, more preferably 0.002 to 20 ppm, and even more preferably 0.005 to 10 ppm.

24. The method according to any one of the preceding claims, in, After step (b) and / or after contacting the nitrate ester, particularly after flow, the relative humidity and / or relative residual moisture of the inert gas is 50% or higher, particularly 65% ​​or higher, preferably 75% or higher, more preferably 80% or higher, and especially preferably 90% or higher, based on a gas temperature of 20°C to 30°C.

25. The method according to any one of the preceding claims, The dried and / or purified, preferably dried and purified, nitrate obtained after method step (b) is obtained and / or collected separately and / or separately from the inert gas; In particular, No additional separation steps are required to separate the dried and / or purified, preferably dried and / or purified, nitrate ester obtained after step (b) from the inert gas.

26. The method according to any one of the preceding claims, The inert gas is recovered and / or recycled after method step (b), particularly after drying and purification and / or simultaneously. In particular, after method step (b), the inert gas is dried and purified, especially using a condenser and / or a gas scrubber or a combination thereof.

27. The method according to any one of the preceding claims, The inert gases obtained and / or separated after method step (b), particularly inert gases loaded with water and / or moisture and volatile impurities, are transferred to a recovery device for gas treatment. In particular, the inert gas is treated to separate water and / or moisture as well as volatile impurities, preferably by condensation and / or washing, more preferably by condensation and washing, and / or In particular, the recovery equipment used for treating and recovering gases includes condensers and / or gas scrubbers or combinations thereof.

28. The method according to claim 27, The treated inert gas is recovered into step (b) of the method; and / or in, The condensate obtained from the treatment of inert gas and / or the obtained washing medium is recycled, particularly after preparation and / or purification, preferably recovered and / or directed to the washing in step (a) of the method.

29. A method for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrates (nitrates), particularly for removing water and volatile and / or permeable impurities generated especially during the production and / or washing of nitrates, especially the method according to any one of the preceding claims. This method includes the following steps: (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. In particular, step (a) and / or washing are performed as liquid-liquid extraction; (b) Subsequently, the washed crude nitrate ester obtained in step (a) is dried and / or purified, preferably dried and purified, by contact with an inert gas, particularly by flow (permeation), in such a manner as to remove water present in the washed crude nitrate ester, and simultaneously and / or in the same manner to remove volatile and / or permeable impurities generated particularly during the production and / or washing of the nitrate ester. In particular, drying and / or purification, preferably drying and purification, are carried out as gas-liquid extraction and / or by desorption, especially as gas-liquid extraction; Wherein, after method step (b), the inert gas is recovered and / or recycled, particularly after and / or simultaneously with drying and purification; specifically, wherein, after method step (b), the inert gas is subjected to drying and purification treatment, particularly by means of a condenser and / or a gas scrubber or a combination thereof; and / or The inert gas obtained and / or separated after method step (b), particularly inert gases loaded with water and / or moisture and particularly volatile impurities, is transferred to equipment for gas treatment and recovery; particularly wherein, Inert gases are treated to separate water and / or moisture, as well as particularly volatile impurities, preferably by condensation and / or washing, and / or particularly wherein the equipment for treating and recovering the gases includes condensers and / or gas scrubbers or combinations thereof. In particular, the treated inert gas is recovered to method step (b); and / or particularly, the condensate obtained from the treatment of the inert gas and / or the obtained washing medium is recycled, especially after preparation and / or purification, preferably recycled to the washing in method step (a).

30. The method according to any one of the preceding claims, The production of the crude nitrate is carried out by adiabatic or isothermal nitration, and / or the method of producing the crude nitrate includes adiabatic or isothermal nitration.

31. An apparatus for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic nitrate esters (nitrates), particularly for removing water and volatile impurities generated during the production and / or washing of nitrate esters, preferably by contact with an inert gas (TG), particularly by flow (permeation), and especially an apparatus for carrying out the method according to any one of the preceding claims. The apparatus has the following devices (W, K, T) that follow each other in the process direction: - At least one washing device (W) for washing with a washing medium obtained from the production process and / or derived from the production equipment (P) NE Crude nitrate (NE) crude ), having a downstream separation device for separating the washing medium from washed crude nitrate (NE) wet Separation; located downstream of the washing equipment (W) in the process direction and / or connected to the downstream of the washing equipment (W). - At least one purification and / or drying device (K), particularly a column, for drying and / or purifying, especially drying and purifying, washed crude nitrates (NE) obtained from washing equipment (W). wet ), in, The purification and / or drying equipment (K) includes a first inlet device (2) and a second inlet device (3). The first inlet device is specifically located in the upper region (KK) of the purification and / or drying equipment (K), particularly at the top of the column, for introducing the washed crude nitrate ester (NE) into the dryer. wet The second inlet device (3) is specifically located in the lower region (KS) of the purification and / or drying equipment (K), particularly at the bottom of the column, for introducing and / or supplying the dry inert gas (TG) into the purification and / or drying equipment (K). dry ) is introduced and / or supplied to the purification and / or drying equipment (K), The purification and / or drying equipment (K) includes a process for washing the crude nitrate (NE) wet ) and dry inert gas (TG) dry The equipment (means) for contacting, and particularly for flowing, the equipment for contacting, and particularly for flowing, is designed in such a way that it removes the washed crude nitrate (NE) wet The water present in the nitrate is removed, and volatile impurities generated, particularly during the production and / or washing of nitrate esters, are removed in the same manner, while obtaining dry (dried) nitrate esters (NE) free of volatile impurities. dry ); located downstream of the purification and / or drying equipment (K) in the process direction and / or connected to its downstream. - At least one for recovering and / or recycling inert gas (TG) dry TG wet Recycling equipment (T), The recovery device (T) mentioned above includes separation equipment for separating water and / or moisture and volatile impurities, particularly condensers and / or gas scrubbers or combinations thereof, especially said separation equipment is designed such that, particularly by condensation and / or scrubbing, preferably condensation and scrubbing, the moisture inert gas (TG) is removed from the gas. wet Water and / or moisture and volatile impurities are separated from the gas, while a dry (dry) inert gas (TG) free of volatile impurities is obtained. dry ); In particular, The recovery device (T) also includes a third inlet device (5), which is specifically arranged in the upper region (KK) of the purification and / or drying device (K), particularly between the column top and the recovery device (T), for introducing a wet inert gas (TG) specifically loaded with water and / or volatile impurities. wet ) Guide and / or supply and / or convey from the purification and / or drying equipment (K) to the recycling equipment (T).

32. The apparatus according to any one of the preceding claims, in, The first inlet device (2) is designed as a connection between the washing device (W) and the purification and / or drying device (K), and / or the first inlet device (2) is designed as a delivery line, particularly as a delivery line for connecting the washing device (W) and the purification and / or drying device (K).

33. The apparatus according to any one of the preceding claims, The second inlet device (3) is designed for drying inert gas (TG). dry The storage device (3) is connected to the purification and / or drying equipment (K), and / or the second inlet device (3) is designed as a delivery line, particularly designed for connection to the drying of inert gas (TG). dry Storage equipment and delivery lines to purification and / or drying equipment (K).

34. The apparatus according to any one of the preceding claims, The third inlet device (5) is designed to connect the purification and / or drying device (K) to the recycling device (T), and / or the third inlet device (5) is also preferably designed as a delivery line, particularly for connecting the purification and / or drying device (K) to the recycling device (T).

35. The apparatus according to any one of the preceding claims, The washing device (W) described therein is designed as a liquid-liquid extraction device; and / or The washing apparatus (W) described herein includes an acidic washing stage, an alkaline (alkali-containing) washing stage, and / or a neutral washing stage, particularly at least one alkaline (alkali-containing) washing stage and / or a neutral washing stage, preferably acidic, alkaline (alkali-containing), and neutral washing stages; and / or The washing device (W) described therein includes one or more washing stages, preferably one, two or three washing stages, more preferably two or three washing stages; in particular, each washing stage is designed in such a way that it includes one or more washing and / or extraction cycles; and / or The washing device (W) is designed in such a way that washing is performed using a water-based washing medium; In particular, the water-based washing medium is set to neutral, acidic, or alkaline (containing alkali).

36. The apparatus according to any one of the preceding claims, The washing apparatus (W) described therein is designed such that washing, particularly in each washing stage, is carried out in a cross-flow or counter-flow or a combination of cross-flow and counter-flow, preferably recovering the washing medium; and / or The washing device (W) described therein is operable and / or operates, particularly at each washing stage, to cross-flow or counter-flow or a combination of cross-flow and counter-flow, preferably to recover the washing medium.

37. The apparatus according to any one of the preceding claims, The separation equipment connected downstream of the washing equipment (W) is designed as a separation device (separator), particularly a static separation device, or a centrifugal separator.

38. The apparatus according to any one of the preceding claims, The purification and / or drying equipment (K) mentioned therein, particularly columns, including single-stage or multi-stage columns, particularly packed bed columns, sieve plate columns, bubble cap disk columns or falling film columns or combinations thereof, and / or includes gas / liquid reactors or stripping equipment.

39. The apparatus according to any one of the preceding claims, The purification and / or drying equipment (K), particularly the column, is a single-stage or multi-stage column, particularly a packed bed column, sieve plate column, bubble cap plate column or falling film column or a combination thereof, and / or a gas / liquid reactor or stripping equipment.

40. The apparatus according to any one of the preceding claims, The purification and / or drying equipment (K), particularly the column, is designed in such a way that drying and / or purification, preferably drying and purification, is carried out as a continuous or discontinuous, particularly continuous process.

41. The apparatus according to any one of the preceding claims, The purification and / or drying equipment (K), particularly the column, preferably includes an outlet and / or discharge device (4), which is particularly arranged in the lower region (KS), preferably at the bottom of the column, for drying (drying) nitrates (NE) free of volatile impurities. dry ); In particular, the outlet and / or discharge equipment (4) is designed as a purification and / or drying equipment (K) for the drying (drying) of nitrates (NE) free of volatile impurities. dry The connection of the collection and / or storage equipment, and / or the outlet and / or discharge equipment (4) thereof, is designed as a delivery pipeline, particularly designed for connecting the purification and / or drying equipment (K) to the dried (dried) nitrate ester (NE) free from particularly volatile impurities. dry Delivery pipelines for collection and / or storage equipment.

42. The apparatus according to any one of the preceding claims, The purification and / or drying equipment (K), particularly the column, is preferably designed as a single-stage or multi-stage packed bed column, sieve plate column, bubble cap disk column, or falling film column, or a combination thereof, with the column bottom (KS) serving as the lower region. Specifically, the purification and / or drying equipment (K) includes, preferably, a drying nitrate ester (NE) free of volatile impurities, preferably arranged at the column bottom (KS). dry (4) Export and / or emission equipment; In particular, the outlet and / or discharge device (4) is designed to be compatible with the purification and / or drying device (K) for drying (drying) nitrates (NE) free of volatile impurities. dry The connection of the collection and / or storage equipment, and / or the outlet and / or discharge equipment (4) thereof, is designed as a delivery pipeline, particularly designed for connecting the purification and / or drying equipment (K) to the dried (dried) nitrate ester (NE) free of volatile impurities. dry Delivery pipelines for collection and / or storage equipment.

43. The apparatus according to any one of the preceding claims, The purification and / or drying equipment (K) is designed as a gas-liquid extraction device and / or desorption device, particularly a gas-liquid extraction device.

44. The apparatus according to any one of the preceding claims, The purification and / or drying equipment (K) described therein is particularly used for washing crude nitrate esters (NE). wet ) and dry inert gas (TG) dry The equipment, especially the flow-through equipment, is designed in such a way that the crude nitrate (NE) obtained from the washing equipment (W) is washed. wet ) and dry inert gas (TG) dry Contact, especially flow, occurs in a cross-flow and / or counter-flow manner, preferably counter-flow; In particular, the purification and / or drying equipment (K) is used to process the crude nitrate (NE) after washing. wet ) and dry inert gas (TG) dry The equipment, especially the flow-through equipment, is designed in such a way that it guides the dry inert gas (TG). dry ) flows upward, guiding the washed crude nitrate ester (NE) wet It flows downwards.

45. The apparatus according to any one of the preceding claims, in, The recovery equipment (T) includes at least two emission devices (6, 7) for emitting dry (dry) inert gas (TG) free of volatile impurities. dry ) and / or water and / or moisture generated from the processing of inert gases and / or having moisture from wet inert gases (TG) wet The washing liquid contains volatile impurities, and specifically includes two discharge devices (6, 7) for discharging dry (dry) inert gas (TG) free of volatile impurities. dry ) and water and / or moisture generated by the processed gas and / or having moisture from wet inert gas (TG) wet The washing liquid contains volatile impurities; In particular, the emission device (6) is designed for direct and / or indirect connection between the recovery device (T) and the purification and / or drying device (K), particularly via a second inlet device (3), and / or specifically wherein the emission device (6) is designed for dry (dried) inert gas (TG) free of volatile impurities. dry The pipeline for conveying dry (dried) inert gas (TG) free of volatile impurities is preferred. dry The pipeline is designed for direct and / or indirect connection between the recovery equipment (T) and the purification and / or drying equipment (K), particularly via a second inlet device (3), especially in such a way that the inert gas (TG) can be transported. dry TG wet The recycling and / or recycling of ); and / or In particular, the discharge device (7) is designed for connection of the recovery device (T) and the washing device (W), and / or specifically, the discharge device (7) is designed for water and / or moisture generated from the treatment of inert gas and / or having moisture from wet inert gas (TG). wet Piping for the delivery of washing liquid containing volatile impurities, particularly designed for use with water and / or moisture generated from the treatment of inert gases and / or containing moisture from wet inert gases (TG). wet The washing liquid containing volatile impurities and the conveying lines used to connect the recovery equipment (T) and the washing equipment (W) are specifically designed in such a way that water and / or moisture generated by the treated gas and / or having moisture from the wet inert gas (TG) are carried out. wet Recovery and / or recycling of the washing liquid containing volatile impurities.

46. ​​The apparatus according to any one of the preceding claims, The device is designed to perform the method according to any one of the preceding method claims.

47. The apparatus according to any one of the preceding claims, Its features The method comprises one or more features of the claims (claims 1 to 30).

48. An apparatus for producing aliphatic or alicyclic nitrates (nitrates), the apparatus comprising: (i) Nitrification equipment (P) NE In particular, it has one or more reaction vessels (nitration reactors) for nitration, especially for the production of aliphatic or alicyclic nitrates (nitrates) from mono- or poly-aliphatic or alicyclic alcohols, preferably by adiabatic or isothermal nitration. (ii) Optionally, located downstream of the production line and / or connected to the nitration unit (P NE Downstream separation equipment, particularly separators, are used to separate residual nitrated acid from the crude nitration product (crude nitrate ester); (iii) At least one washing device (W) arranged downstream of the production line and / or connected to the nitration unit (P). NE ) and optionally present downstream separation equipment, used for washing with washing media obtained from the production process and / or derived from the production equipment (P NE Crude nitrate (NE) crude A separation unit is arranged and / or connected downstream for separating the washing medium from the washed crude nitrate (NE). wet Separation; (iv) At least one purification and / or drying device (K), particularly a column, arranged downstream of the production line and / or connected downstream of the washing equipment (W), for drying and / or purifying, particularly drying and purifying, the washed crude nitrates (NE) obtained from the washing equipment (W). wet ), The purification and / or drying equipment (K) includes a first inlet device (2) and a second inlet device (3), wherein the first inlet device is specifically located in the upper region (KK) of the purification and / or drying equipment, particularly at the top of the column, for introducing the washed crude nitrate ester (NE) into the dryer. wet The second inlet device (3) is specifically located in the lower region (KS) of the purification and / or drying equipment, particularly at the bottom of the column, for introducing and / or supplying the dry inert gas (TG) into the purification and / or drying equipment (K), wherein the second inlet device (3) is specifically located in the lower region (KS) of the purification and / or drying equipment, particularly at the bottom of the column, for introducing and / or supplying the dry inert gas (TG) into the purification and / or drying equipment (K). dry ) is introduced and / or supplied to the purification and / or drying equipment (K), The purification and / or drying equipment (K) includes a process for washing crude nitrate (NE) wet ) and dry inert gas (TG) dry The equipment for contact, especially flow (permeation), particularly the equipment used for contact, especially flow, is designed in such a way that the washed crude nitrate (NE) is removed. wet The water present in the nitrate is removed, and / or volatile impurities generated, particularly during the production and / or washing of nitrate esters, are removed in the same manner, while obtaining dry (dried) nitrate esters (NE) free of volatile impurities. dry ); arranged downstream in the process direction and / or connected downstream of the purification and / or drying equipment (K), (v) At least one recovery device (T), arranged downstream of the production line and / or connected to the purification and / or drying equipment (K), particularly downstream of the column, for recovering and / or circulating inert gas (TG). dry TG wet ), The recovery device (T) mentioned above includes separation equipment for separating water and / or moisture and volatile impurities, particularly condensers and / or gas scrubbers or combinations thereof, especially said separation equipment is designed such that, particularly by condensation and / or scrubbing, preferably condensation and scrubbing, the moisture inert gas (TG) is removed from the gas. wet Water and / or moisture and volatile impurities are separated from the gas, while a dry (dry) inert gas (TG) free of volatile impurities is obtained. dry ); Specifically, the recovery device (T) further includes a third inlet device (5), which is specifically arranged in the upper region (KK) of the purification and / or drying device (K), particularly between the column top and the recovery device (T), for introducing a wet inert gas (TG) specifically loaded with water and / or volatile impurities. wet ) is introduced and / or supplied and / or conveyed from the purification and / or drying equipment (K) to the recycling equipment (T).

49. An apparatus for producing aliphatic or alicyclic nitrates (nitrates), particularly the apparatus according to claim 48, the apparatus comprising: (i) Nitrification equipment (P) NE In particular, it has one or more reaction vessels (nitration reactors) for nitration, especially for the production of aliphatic or alicyclic nitrates (nitrates) from mono- or poly-aliphatic or alicyclic alcohols, preferably by adiabatic or isothermal nitration. (ii) Optionally, located downstream of the production line and / or connected to the nitration unit (P NE Downstream separation equipment, particularly separators, is used to separate residual nitrated acid from the crude nitration product (crude nitrate ester); (iii) The apparatus according to any one of the preceding claims (claims 31 to 47), which is arranged downstream of the production line and / or connected to the nitration unit (P NE (and the downstream of the optional separation equipment).

50. The production apparatus according to claim 48 or 49, in, The production apparatus is designed to implement the method according to any one of the preceding method claims (claims 1 to 30).

51. The production apparatus according to any one of the preceding claims, Its features are, One or more features of the method claims (claims 1 to 30) and / or the apparatus claims (claims 31 to 47).

52. Use of inert gases for drying and / or purifying, preferably drying and purifying aliphatic or alicyclic crude nitrates (nitrate esters) obtained from the production process, especially for removing water and volatile impurities generated particularly during the production and / or washing of nitrate esters.

53. Use of inert gases for drying and / or purifying, preferably drying and purifying, aliphatic or alicyclic crude nitrates (nitrate esters) obtained from the production process, particularly for removing water and volatile impurities generated during the production and / or washing of nitrate esters, by contacting the aliphatic or alicyclic crude nitrate ester with an inert gas, particularly by permeation, in such a manner that water present in the washed crude nitrate ester is removed, and / or volatile impurities generated during the production and / or washing of nitrate esters are removed in the same manner.

54. The use according to claim 52 or 53 in (a) First, the crude nitrate ester obtained from the production process is washed with a washing medium, and then the washing medium is separated. (b) Subsequently, the washed crude nitrate ester obtained in this manner is dried and / or purified, preferably dried and purified, by contacting the washed crude nitrate ester with an inert gas, particularly by permeation, in such a way as to remove water present in the washed crude nitrate ester, and at the same time and / or in the same way to remove volatile and / or volatile impurities generated particularly during the production and / or washing of the nitrate ester.

55. Use of an inert gas in the method according to any one of the preceding method claims and / or in the apparatus according to any one of the preceding apparatus claims and / or in the production apparatus according to the preceding production apparatus claims for drying and / or purification, preferably drying and purification.

56. The use according to any of the preceding claims, Its features One or more features of the method claims (claims 1 to 30) and / or the apparatus claims (claims 31 to 47) and / or the production apparatus claims (claims 48 to 51).

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