Sustainable preparation of organic amino compounds for the production of organic isocyanates

Abstract

The invention relates to a process according to claim 1, in which nitric acid, as direct process product from a process for nitric acid preparation comprising the following steps: a) providing hydrogen gas (5d) and oxygen gas (5b) by performing a water electrolysis (5) in an electrolysis apparatus using electrical energy (10) produced from renewable energy and water (5c); b) providing ammonia (21b) as process product of a reaction of at least nitrogen (21a) and hydrogen gas (5d) from said water electrolysis (5) in an ammonia synthesis (21); c) preparing nitric acid (22) by reacting previously provided ammonia (21b) in a nitric acid preparation (22) at least with oxygen-containing gas (5e), is used for preparation 22 of organic amino compounds 17 for the synthesis of organic isocyanate compounds. Also described are the incorporation of this process into a process for preparing organic isocyanate compounds with these organic amino compounds, and an apparatus for performing the corresponding process.

Description

[0001] “Sustainable production of organic amino compounds for the production of organic isocyanates”

[0002] The invention relates to a process for the sustainable production of organic amino compounds for the synthesis of organic isocyanate compounds, wherein organic amino compounds are produced using green hydrogen and green ammonia, as well as a process for the production of organic isocyanate compounds with these organic amino compounds and an apparatus for carrying out the corresponding process.

[0003] Isocyanates are typically produced by reacting amines with phosgene, producing hydrogen chloride as a byproduct. The carbon monoxide required for phosgene synthesis is obtained from a reforming process using natural gas, while the chlorine for phosgene synthesis is generated by recycling hydrogen chloride from isocyanate production or by chlor-alkali electrolysis.

[0004] Amines are produced by hydrogenating nitro compounds, which in turn are produced from nitric acid derived from the corresponding precursors. The nitric acid is produced from ammonia, for which hydrogen is typically provided from a reformer process.

[0005] The isocyanates are converted from phosgene and amines and these are reacted with polyols and / or polyesters to form polyurethane material.

[0006] Polyurethanes, also abbreviated to PU, are plastics that result from the polyaddition reaction of polyols containing at least two hydroxyl groups with polyisocyanates. Unless otherwise stated, polyisocyanates are referred to as isocyanates. Amines used to produce the isocyanates are also polyamines and are referred to as amines. The use of diols and diisocyanates results in linear polyurethanes. Crosslinked polyurethanes can be produced by reacting triisocyanate-diisocyanate mixtures with triol-diol mixtures. The properties of PU can be varied widely. Depending on the degree of crosslinking and / or the isocyanate or OH component used, thermosets, thermoplastics, or elastomers are obtained. However, polyurethanes are also used as molding compounds for compression molding, as casting resins (isocyanate resins), as (textile) elastic fibers, polyurethane coatings, and as polyurethane adhesives.Polyurethane is also very easy to produce foams.

[0007] Soft PU foams are used for many purposes, especially as upholstery material for furniture and car seats, as mattress foam, as carpet backing material, for textile lamination, as cleaning sponges, or as filter material.

[0008] PU rigid foams are primarily used for thermal insulation, e.g., in buildings, refrigeration units, heat and cold storage systems, and some piping systems (plastic-coated composite pipes, flexible composite pipes).

[0009] Other relatively new areas of application for PU foams are in vehicle construction, such as steering wheels, armrests, soft coating of handles, interior trim, dashboards, sound insulation, rattle protection, seals, and transparent coating of wood decors.

[0010] The object of the present invention was to find a more sustainable process for the synthesis of organic amino compounds for isocyanate production and ultimately also for polyurethane production, which can be used in existing production processes without great additional effort.

[0011] In applying the UN definition of sustainability (“sustainable development”) according to the Brundtland Report of the World Commission on Environment and Development, the person skilled in the art understands the “sustainability” of a process to mean that the implementation of the process in the present makes as little or no contribution as possible to ensuring that future generations of humanity will no longer be able to meet their own needs, in particular needs with regard to the use of resources such as fossil fuels and in particular needs with regard to the conservation of habitats, such as the protection of the Earth's atmosphere. The object of the invention is therefore to make the production of organic amines, as well as the organic isocyanate and polyurethane produced therefrom, more sustainable than the production methods known from the prior art.The contribution of isocyanate and polyurethane production to a declining satisfaction of the needs of future generations should be reduced or even avoided.

[0012] The present invention provides a process for producing organic amino compounds for the synthesis of organic isocyanate compounds, comprising at least the steps of i) providing at least one organic nitro compound as a process product of a process for synthesizing at least one organic nitro compound, which comprises at least the following steps: i-1) providing nitric acid as a direct process product of a process for producing nitric acid, which comprises at least the following steps: a) providing hydrogen gas and oxygen gas by carrying out a water electrolysis in an electrolysis device using electrical energy produced from renewable energy and water; b) providing ammonia as a direct process product of a reaction of at least nitrogen and hydrogen gas from said water electrolysis in an ammonia synthesis;c) Production of nitric acid by reacting previously produced ammonia in a nitric acid production facility at least with oxygen-containing gas; i-2) Synthesis of at least one organic nitro compound, preferably at least one aromatic organic nitro compound, at least by nitration of at least one organic compound, preferably at least one aromatic organic compound, with at least said provided nitric acid; ii) Provision of hydrogen gas, preferably by carrying out water electrolysis in an electrolysis device using electrical energy produced from renewable energy;iii) introducing the at least one provided organic nitro compound and the provided hydrogen gas into a hydrogenation and subsequent hydrogenation by reducing nitro groups of said at least one organic nitro compound by reacting them with said hydrogen gas to obtain at least one organic amino compound, preferably at least one aromatic organic amino compound;

[0013] For the provision of the at least one organic nitro compound according to step i), it is sufficient if the at least one organic nitro compound is necessarily a direct process product of at least steps i-1) and i-2) of the aforementioned process. This means that for the implementation of the step of providing the at least one organic nitro compound, it is sufficient to simply remove said organic nitro compound as a direct process product of at least steps i-1) and i-2) from a storage container or a feed line as a raw material within the scope of a delivery.In this case, the producer of the organic amine according to the process according to the invention does not carry out the above-mentioned steps for preparing the at least one organic nitro compound himself, but ensures that an organic nitro compound provided for preparing the organic amine has been prepared by applying a process comprising at least steps i-1) and i-2) and is thus its direct process product.

[0014] In the case of delivery, the process is preferably carried out in such a way that in step i) the organic nitro compound is provided as a process product of said synthesis of step i-2) in a mobile, closed transport container, optionally transferred therefrom for intermediate storage into storage containers, wherein said synthesis and the hydrogenation according to step iii) are not in fluid communication with each other.

[0015] A fluid connection is a part of a device that connects other parts of the device to one another and through which a substance, which can exist in any state of matter, can be transported as a material flow from one part of the device to the next, for example, a supply line in the form of a pipe. The term "fluidly connected" means that the named parts of the device are connected to one another via a fluid connection.

[0016] Said movable, enclosed transport container can, for example, be the tank of a tank wagon, a tanker, or a tank truck. "Enclosed" means that the said transport container is closed at its device for filling or unloading the transported goods during transport.

[0017] For the purposes of the invention, a storage container is defined as a container that is tied to a fixed location, such as a tank farm. Storage containers are considered to be part of immovable fixed assets or are part of them.

[0018] Within the scope of a preferred embodiment of the process according to the invention, the organic nitro compound is provided as a direct process product of said synthesis of step i-2) in the form of a material stream directly via a fluid connection from said synthesis via any necessary intermediate storage in at least one storage container, wherein said synthesis, any necessary at least one storage container, and the hydrogenation according to step iii) are in fluid communication with one another. A process of this preferred embodiment comprises, as a particularly preferred embodiment, at least the steps i) producing at least one organic nitro compound by at least the following steps: i-1) providing nitric acid as a direct process product of a process for nitric acid production,which comprises at least the following steps: a) Providing hydrogen gas and oxygen gas by carrying out a water electrolysis in an electrolysis device using electrical energy and water produced from renewable energy; b) Providing ammonia as a direct process product of a reaction of at least nitrogen and hydrogen gas from said water electrolysis in an ammonia synthesis; c) Producing nitric acid by reacting previously provided ammonia in a nitric acid production facility at least with oxygen-containing gas; i-2) Synthesis of at least one organic nitro compound, preferably at least one aromatic organic nitro compound, at least by nitration of at least one organic compound, preferably at least one aromatic organic compound, with at least the said provided nitric acid; ii) Providing hydrogen gas,preferably by carrying out water electrolysis in an electrolysis device using electrical energy generated from renewable energy; iii) introducing the organic nitro compound and the provided hydrogen gas into a hydrogenation and subsequent hydrogenation by reducing nitro groups of said at least one organic nitro compound by reacting them with said hydrogen gas to obtain at least one organic amino compound, preferably at least one aromatic organic amino compound, with the proviso that the organic nitro compound is introduced in the form of a material stream via a fluid connection from said synthesis of step i-2), optionally via intermediate storage in at least one storage container, wherein said synthesis and the hydrogenation according to step iii) and optionally the at least one storage container are in fluid communication with one another.

[0019] The synthesis of the at least one organic nitro compound is carried out according to step i-2) starting from said organic compound and said nitric acid in a manner well known to the person skilled in the art. For example, the synthesis in step i-2) can produce organic mononitro compounds, in particular organic, aromatic mononitro compounds, as described in EP 0668263 A1, which is expressly incorporated herein by reference in its entirety. Preferred organic nitro compounds include mononitrobenzene. Furthermore, organic dinitro compounds, such as dinitrotoluene (DNT), can be provided by the synthesis of step i-2). The preparation of dinitrotoluene is well known to the person skilled in the art, for example from the publications Ullmann's Enzyklopädie der technischen Chemie, 4th Edition, Volume 17, page 391 ff, 1979, Verlag Chemie Weinheim / New York; H. Hermann, J. Gebauer, P.Konieczny, "Industrial Nitration of Toluene to Dinitrotoluene" in ACS- Symposium, Series 623, 234-249, 1996, ed. LF Albright, RVC or from EP 1 880 989 A1, which are expressly incorporated herein by reference.

[0020] To prepare the organic nitro compound, according to step i-2), an organic compound, preferably at least one aromatic organic compound, is nitrated using at least the nitric acid provided. The organic compound used is particularly preferably selected from benzene or toluene.

[0021] In a further embodiment, it has been found to be more sustainable if at least one organic compound used in step i-2) is an aromatic organic compound which is provided as a direct process product of a process comprising at least the following steps:

[0022] Pyrolysis of organic material at a temperature of 600 to 1000°C to obtain gaseous pyrolysate and pyrolysis residue;

[0023] Contacting the gaseous pyrolysate with a heterogeneous catalyst to obtain a conversion product containing at least one aromatic organic compound having a molecular weight of less than 300 g / mol;

[0024] Processing the conversion product to obtain the said aromatic organic compound, in particular selected from benzene, toluene or xylene.

[0025] A corresponding pyrolysis process for providing the conversion product is described, for example, in WO 2020 / 204707 A1, which is expressly incorporated by reference in this application. Heterogeneous catalysts suitable for the process for producing the conversion product are also described therein.

[0026] As an organic material, plastic, such as polyurethane material and / or polycarbonate material, can be used in pyrolysis. This plastic is preferably plastic waste, such as polyurethane material waste. The "plastic waste", in particular "polyurethane material waste", can have arisen from the use of plastic, in particular polyurethane, on the market. In the case of polyurethane material waste, the polyurethane was again preferably produced from diisocyanates, which were produced from organic amines provided by the process according to the invention. The recycling of such polyurethane material waste in the process according to the invention is referred to as a "closed-loop" process.However, it is of course also possible in this embodiment of the process according to the invention to utilize such polyurethane material waste that originates from polyurethanes that were not produced from diisocyanates from the process according to the invention.

[0027] A corresponding pyrolysis process for the provision of aromatic organic compounds is further improved, in which the pyrolysis residue obtained during pyrolysis is converted into carbon monoxide, hydrogen and residue in a gasification with partial oxidation and the carbon monoxide formed, after optional workup of a phosgene synthesis, and the hydrogen are introduced into the provision of hydrogen according to step ii) of the process.

[0028] The synthesis of the at least one organic nitro compound is carried out according to step i-2) starting from at least one organic compound and nitric acid. According to step i-1) of the process according to the invention and its further embodiments, nitric acid is provided for this synthesis of step i-2). For the provision of the at least one organic nitro compound, it is sufficient if the nitric acid provided is necessarily a direct process product of at least steps i-1) a) to c) of the process of this preferred embodiment or of the general process of the invention.

[0029] This means that, for carrying out the step of providing nitric acid, it is sufficient to simply withdraw said nitric acid as a direct process product of a process comprising at least steps i-1) a) to i-1) c) as a raw material from a storage container or a feed line as part of a delivery. In this case, the producer of the organic amine or the organic nitro compound according to the invention does not carry out the aforementioned steps for producing nitric acid themselves, but merely ensures that the nitric acid provided for producing the organic amine or for producing the organic nitro compound has been produced by applying at least steps i-1) a) to c) and is thus their direct process product.In the case of delivery, the process is preferably carried out in such a way that in step i-1) the nitric acid is provided as a direct process product of said nitric acid production in a mobile, closed transport container, optionally transferred therefrom for intermediate storage into storage containers, wherein said nitric acid production and the synthesis according to step ii) are not in fluid communication with each other.

[0030] It is also possible according to the invention if, to provide the nitric acid, at least one of the aforementioned reaction steps for producing nitric acid is carried out as an integral step of a process according to the invention for producing organic amine, and the nitric acid obtained thereby, optionally after intermediate storage in a storage container, is fed to the synthesis of the organic nitro compound. It is in turn preferred if, in step i-1), the nitric acid is provided as a process product of said nitric acid production in the form of a material stream directly via a fluid connection from said nitric acid production via any necessary intermediate storage in at least one storage container, wherein said nitric acid production, the optionally necessary at least one storage container, and the synthesis according to step i-2) are connected to one another via a fluid connection.

[0031] A process of this preferred embodiment comprises, as a particularly preferred embodiment, at least the steps i) producing at least one organic nitro compound by at least the following steps: i-1) producing nitric acid as a direct process product of a process for nitric acid production, which comprises at least the following steps: a) providing hydrogen gas and oxygen gas by carrying out a water electrolysis in an electrolysis device using electrical energy produced from renewable energy and water; b) providing ammonia as a direct process product of a reaction of at least nitrogen and hydrogen gas from said water electrolysis in an ammonia synthesis; c) producing nitric acid by reacting previously provided ammonia in a nitric acid production process at least with oxygen-containing gas; i-2) synthesizing at least one organic nitro compound,preferably at least one aromatic organic nitro compound, at least by nitration of at least one organic compound, preferably at least one aromatic organic compound, with at least said provided nitric acid; ii) providing hydrogen gas, preferably by carrying out a water electrolysis in an electrolysis device using electrical energy produced from renewable energy; iii) introducing the organic nitro compound and the provided hydrogen gas into a hydrogenation and subsequent hydrogenation by reducing nitro groups of said at least one organic nitro compound via their reaction with said hydrogen gas to obtain at least one organic amino compound, preferably at least one aromatic organic amino compound, with the proviso,that, on the one hand, in step i-1), the nitric acid is provided as a direct process product of said nitric acid production in the form of a material stream directly via a fluid connection from said nitric acid production via a possibly necessary intermediate storage in at least one storage container, wherein said nitric acid production, the possibly necessary at least one storage container and the synthesis according to step ii) are connected to one another via a fluid connection, and, on the other hand, the organic nitro compound is introduced in the form of a material stream via a fluid connection from said synthesis of step i-2), optionally via an intermediate storage in at least one storage container, wherein said synthesis and the hydrogenation according to step iii) and optionally the at least one storage container are in fluid communication with one another.

[0032] The nitric acid is produced according to step i-1) c) starting from said ammonia and said oxygen-containing gas (for example air or oxygen gas) in a manner well known to those skilled in the art, for example as described in the document EP 0 808 797 A2, to which reference is expressly made here in its entirety. Preferably, oxygen gas is used as the oxygen-containing gas for producing the nitric acid in step i-1) c). According to step i-1) b) of the process according to the invention and its further embodiments, ammonia is provided for step i-1) c). For providing the at least one organic nitro compound according to step i-1), it is sufficient if the ammonia provided for providing nitric acid is necessarily a direct process product of at least step i-1) b).This means that, for carrying out the step of providing the ammonia, it is sufficient to simply withdraw said ammonia as a direct process product of at least step i-1) b) as part of a supply as a raw material from a storage container or from a feed line. In this case, the producer of the organic amine or the organic nitro compound according to the process of the invention does not carry out the aforementioned steps for producing the ammonia itself, but merely ensures that the ammonia provided for producing the organic amine or for producing the organic nitro compound was produced by applying a process comprising at least step i-1) b) and is thus its direct process product.

[0033] According to the invention, it is possible if, to provide the ammonia, at least one of the aforementioned reaction steps for producing the ammonia is carried out as an integral step of a process according to the invention for producing organic amine, and the ammonia obtained thereby, optionally after intermediate storage in a storage container, is fed to the provision or production of nitric acid. It is in turn preferred if, in step i-1) b), the ammonia is provided as a direct process product of said ammonia production in the form of a material stream directly via a fluid connection from said ammonia production via any necessary intermediate storage in at least one storage container, wherein said ammonia production, the optionally necessary at least one storage container, and the synthesis according to step ii) are connected to one another via a fluid connection.

[0034] In those embodiments of the invention in which the nitric acid is provided directly as a material stream from the nitric acid production via a fluid connection between the synthesis of step i-2) and the hydrogenation according to step iii) and optionally the at least one storage container, it has additionally proven to be preferred if, in step i-1), the ammonia is provided as a direct process product of said ammonia production in a mobile, closed transport container, optionally transferred therefrom for intermediate storage into storage containers, wherein said ammonia production and the nitric acid production are not in fluid communication with one another. In this case, it is again particularly preferred if, for the production of organic amines for the synthesis of organic isocyanate compounds,at least the following steps are carried out: i) producing at least one organic nitro compound by a process for synthesizing at least one organic nitro compound, which comprises at least the following steps: i-1) producing nitric acid by carrying out a process for producing nitric acid, which comprises at least the following steps: a) and b) providing ammonia as a direct process product of a reaction of at least nitrogen and hydrogen gas, which was produced alongside oxygen gas by carrying out a water electrolysis in an electrolysis device using electrical energy produced from renewable energy and water; c) producing nitric acid in a nitric acid production process by reacting previously provided ammonia at least with oxygen-containing gas; i-2) synthesizing at least one organic nitro compound, preferably at least one aromatic organic nitro compound,at least by nitration of at least one organic compound, preferably at least one aromatic organic compound, with at least said nitric acid; ii) providing hydrogen gas, preferably by carrying out water electrolysis in an electrolysis device using electrical energy generated from renewable energy; iii) introducing the at least one organic nitro compound and the provided hydrogen gas into a hydrogenation and subsequent hydrogenation by reducing nitro groups of said at least one organic nitro compound via their reaction with said hydrogen gas to obtain at least one organic amino compound, preferably at least one aromatic organic amino compound.

[0035] The ammonia is produced according to step i-1) b) starting from nitrogen and hydrogen provided in step i-1) a) in a manner well known to the person skilled in the art, as described, for example, according to the Haber-Bosch process using known reactor technologies and designs for this process, to which reference is expressly made in full here.

[0036] For the provision or production of nitric acid, it has proven preferable for the nitrogen used to produce ammonia in step i-1) b) to be provided by air separation. Air separation processes and correspondingly suitable nitrogen production plants are state-of-the-art and are commercially available.

[0037] The oxygen used in the oxidation reaction of nitric acid production can also be provided by air separation. Therefore, within the scope of a further embodiment, a preferred process is characterized in that the nitric acid provided in step i-1) is a process product of nitric acid production, in which at least one oxygen-containing gas (5e) selected from oxygen from water electrolysis, air, or oxygen from air separation is used for the oxidation reaction of step c).If air separation is used to provide oxygen for the oxidation, it is particularly preferred if the nitric acid provided in step i-1) is a direct process product of nitric acid production, in which oxygen for the oxygen-containing gas for the oxidation reaction of step c) is provided by air separation, which also supplies nitrogen for step i-1) b). The provision of hydrogen gas in step i-1) a) of the process as part of the production of ammonia for nitric acid production necessarily takes place by water electrolysis, which is operated partially or completely with electrical power provided using renewable energy as the energy source.

[0038] The provision of hydrogen gas in step ii) of the process for the hydrogenation in step iii) of the process can be effected, for example, by water electrolysis or by electrolysis for the production of chlorine, or by a combination thereof, wherein said selected electrolysis is in each case operated partially or completely with electrical current provided using renewable energy as the energy source. In one embodiment of the process, it has proven advantageous if the hydrogen provided in step ii) is produced at least by electrolysis of water using electrical energy, wherein the electrical energy provided as renewable energy is optionally wind power, solar energy, hydropower, or mixtures thereof.

[0039] The term “renewable energy” is understood by those skilled in the art to mean energy from a non-exhaustive energy source, such as wind energy, water energy, bioenergy (e.g. conversion of biogas or biomass into electricity) or solar energy. Therefore, particularly suitable renewable energies are wind power, solar energy, water power or mixtures thereof. If regenerative energy is used as an energy source within the scope of the present invention, in particular for the provision of electrical power, then it can be advantageous to ensure that the method according to the invention is carried out during a period of renewable energy shortage by storing renewable energy at a time when it is available to bridge periods of shortage, e.g. in the form of electrical power in a battery.

[0040] Water electrolysis to produce hydrogen gas is the electrochemical conversion of water. Using electricity, water is split into hydrogen and oxygen. Well-known processes include proton exchange electrolysis (PEM electrolysis), which is described, for example, in EP 3489394 A. Another process is alkaline water electrolysis. The two processes differ, in particular, in the process parameters such as temperature, pressure, and pH. However, both processes lead to the target products of water and oxygen gas. Water electrolysis can be carried out using state-of-the-art systems. Technical systems for both alkaline water electrolysis and PEM electrolysis are well-known and commercially available. The principles of water electrolysis are described, for example, in Chapter 6.3.4 of Volkmar M. Schmidt's "Electrochemical Process Engineering" (2003 Wiley-VCH-Verlag; ISBN 3-527-29958-0).

[0041] In step iii) of the process according to the invention, the at least one organic nitro compound from step i) and the hydrogen gas provided in step ii) of the process are introduced into a hydrogenation reaction. Subsequently, the hydrogenation is carried out by reducing nitro groups of said at least one organic nitro compound by reacting them with said hydrogen gas.

[0042] The hydrogenation of organic nitro compounds with hydrogen gas is well known to those skilled in the art. The skilled person is familiar with hydrogenation reactions that can be used and utilized for step iii), for example, from the publications Gerald Booth (2007), Ullmanns Enzyklopädie der Industriechemie, Weinheim, Wiley VCH, doi: 10.1002 / 14356007. a17_411, which are expressly incorporated herein by reference.

[0043] A further preferred embodiment of the process according to the invention is characterized in that the organic amino compound obtained in step iii) is selected from tolylenediamine (TDA), methylenedi(phenylamine) (MDA), in turn preferably selected from diphenylmethane-2,2'-diamine, diphenylmethane-2,4'-diamine, diphenylmethane-4,4'-diamine or mixtures thereof) or mixtures thereof.

[0044] The organic amino compounds prepared by the process according to the invention are preferably suitable for the synthesis of organic isocyanate. In a further preferred embodiment of the process according to the invention, at least the following steps are additionally carried out for the synthesis of organic isocyanate: iv) synthesis of phosgene from at least carbon monoxide and chlorine gas; v) isocyanate production from organic isocyanate by reacting at least the phosgene with the at least one organic amino compound, with release of hydrogen chloride.

[0045] A further subject of the invention is therefore a process for the synthesis of organic isocyanate, comprising at least the steps

[0046] Providing at least one organic amino compound as a direct process product of the previously described process for preparing organic amines for the synthesis of organic isocyanate compounds;

[0047] Synthesis of phosgene from at least carbon monoxide and chlorine gas;

[0048] Isocyanate production from organic isocyanate by reacting at least the phosgene with at least one organic amino compound, with release of hydrogen chloride.

[0049] Within the scope of providing at least one organic amino compound, a process product of the previously described process for preparing organic amines for the synthesis of organic isocyanate compounds is provided. All preferred embodiments of this process for preparing organic amines for the synthesis of organic isocyanate compounds are also considered preferred in this process step.

[0050] Phosgene can, for example, be synthesized industrially by reacting chlorine gas and carbon monoxide at elevated temperatures over a special activated carbon catalyst using energy, e.g. to cool the reaction zone and increase the temperature. On an industrial scale, tubular reactors equipped with activated carbon are typically used for this purpose. Appropriate devices and processes for synthesizing phosgene are well known to those skilled in the art. To provide the gaseous chlorine for phosgene synthesis, the skilled person will know of the production of chlorine gas from electrochemical oxidation after hydrochloric acid electrolysis with a gas diffusion electrode (also known as the HCl ODC electrolysis process (ODC stands for Oxygen Depleting Electrode, and the so-called ODC (oxygen depleting cathode) is used, for example). Suitable electrolysis cells can be found in:US, 6022, 634 A, WO 03 / 31690 A1), the production of chlorine gas from hydrochloric acid diaphragm electrolysis (cf. EP 1 103636 A1), the production of chlorine gas from thermocatalytic gas phase oxidation (cf. WO 2012 / 025483 A2), and the production of chlorine from chlor-alkali electrolysis (cf. WO 2009 / 007366 A2) are well known. The content of the aforementioned documents cited in connection with the production of chlorine gas is expressly and fully incorporated by reference. The following embodiments of the process according to the invention are therefore preferred, in which the chlorine gas is provided at least by at least one chlorine synthesis selected from.

[0051] A) an oxidative conversion of the separated and purified hydrogen chloride from the isocyanate production in a thermocatalytic gas phase oxidation with oxygen to chlorine and water,

[0052] B) a reaction of the purified hydrogen chloride from the isocyanate production with water to form hydrochloric acid, if necessary the purification and electrochemical oxidation of the hydrochloric acid to chlorine and if necessary hydrogen.

[0053] In a preferred variant of this embodiment of the process, the chlorine required for the synthesis of phosgene is produced electrolytically, in particular by electrochemical oxidation after hydrochloric acid electrolysis with a gas diffusion electrode, by electrochemical oxidation after hydrochloric acid diaphragm electrolysis, or by electrochemical oxidation after chlor-alkali electrolysis. It is particularly preferred if said electrochemical oxidation in the electrolysis is carried out using electricity generated from renewable energy, in particular from renewable energy in the form of wind power, solar energy, or hydropower.

[0054] In a further preferred embodiment of the process, the carbon monoxide required for the synthesis of phosgene is produced from CO2, at least by at least one process selected from

[0055] A) the electrochemical reduction of CO2 using electrical energy produced from renewable energy,

[0056] B) a reformer process in which methane (preferably biomethane) and water vapor are converted to carbon monoxide with the addition of at least CO2 and with the addition of heat energy at a temperature of at least 500°C, C) conversion of hydrogen and CO2 to carbon monoxide in a reverse water-gas shift RWGS reaction zone.

[0057] The person skilled in the art knows, for example, from the document WO 2021 / 069470 A, electrodes and a method for carrying out an electrochemical reduction of CO2.

[0058] The electrochemical reduction of CO2 is preferably carried out according to a process described in WO 2021 / 069470 A. This publication is expressly incorporated herein by reference in its entirety. In this preferred electrolytic process for producing carbon monoxide, carbon monoxide, optionally hydrogen, and chlorine are obtained by electrochemical conversion of carbon dioxide and alkali metal chloride solution.This preferred electrolysis process is characterized in that the carbon dioxide is electrochemically reduced at a gas diffusion electrode as cathode in an aqueous alkali chloride-containing solution as catholyte and at the same time chlorine is anodically generated from an aqueous alkali chloride-containing solution as anolyte, wherein the alkali salt of carbonic acid formed in the catholyte, selected from alkali carbonate, alkali hydrogen carbonate or mixtures thereof, is then reacted with hydrogen chloride to form carbon dioxide and alkali chloride and the carbon dioxide released in this process is returned to the cathode compartment to the gas diffusion electrode and the alkali chloride produced is returned optionally to the anode compartment and / or to the cathode compartment.

[0059] A suitable reformer process, in which methane (preferably biomethane) and steam are converted into carbon monoxide with the addition of at least CO2 and with the addition of thermal energy at a temperature of at least 500°C, is described in the PCT patent application with the application number PCT / EP2022 / 052267, to which reference is expressly made in its entirety. This process relates to the production of carbon monoxide from methane, steam, and CO2 for the preparation of phosgene for the synthesis of organic isocyanate, comprising at least the steps

[0060] Synthesis of carbon monoxide in a reformer process in which methane and water vapor are converted into carbon monoxide-containing product gas with the addition of at least CO2 and with the addition of heat energy at a temperature of at least 500°C,

[0061] Purification of the carbon monoxide-containing product gas obtained from the aforementioned synthesis, at least by separation of CO2 and optionally additionally by at least one separation selected from the separation of water, the separation of hydrogen or a combination thereof, to obtain carbon monoxide; provision of CO2 for said addition to the aforementioned reformer process at least from said separation of CO2 of the aforementioned purification step, with the proviso that

[0062] 1) the heat energy supplied to the reformer process for the synthesis of carbon monoxide is provided by at least one method selected from (i) the combustion of fuel containing hydrogen produced by means of renewable energy, (ii) the combustion of fuel containing methane from a biological source, (iii) conversion of electrical energy produced from renewable energy into heat; or

[0063] 2) for the provision of the CO2 added to the synthesis of the aforementioned reforming process, additional CO2 is used from another CO2 source; or

[0064] 3) a combination of the above options 1) and 2) is chosen.

[0065] The preferred methane source for the reformer process is methane from biological sources. Experts define "methane from biological sources" (also referred to as biomethane), as distinct from fossil methane, as methane that is technically obtained from biomass through methane fermentation. Methane fermentation is known to be the anaerobic decomposition of organic matter by microorganisms. Methane from biological sources is produced, for example, in biogas plants, where both organic waste and renewable raw materials are fermented accordingly.

[0066] In a particularly preferred embodiment of the process according to the invention in its embodiment involving phosgene production for isocyanate synthesis, the carbon monoxide for the phosgene synthesis, in particular for the phosgene synthesis according to step iv), is produced from CO2 by at least one conversion of hydrogen and CO2 in a reverse water-gas shift (RWGS) reaction zone to carbon monoxide. Such an embodiment is described, for example, in document WO 2021 / 089737 A, which is expressly incorporated herein by reference in its entirety.

[0067] A "reaction zone" is the part of a reaction space in which a chemical reaction, e.g., a reverse water gas shift reaction, takes place. A "reaction space" is a volume in which the reactants involved in a chemical reaction are brought together and in which the chemical reaction takes place. For a chemical reaction, this could, for example, be the volume of a vessel containing a reactant, e.g., carbon dioxide in the case of a reverse water gas shift reaction, and its reactant, hydrogen in the case of a reverse water gas shift reaction, together and reacted in the reaction zone.

[0068] In this particularly preferred process, at least the following steps are most preferably carried out for the production of carbon monoxide

[0069] Purification of a CO2 gas stream from secondary components, in particular nitrogen oxides, sulphur compounds, dust, water, oxygen and HCl, optionally by means of adsorption, gas scrubbing or catalytic treatment to obtain purified carbon dioxide,

[0070] Feeding of provided hydrogen gas together with the purified CO2 gas stream into a RWGS reaction zone and conversion of the reactants according to the principle of the RWGS reaction to a product gas mixture of water vapor, CO and optionally by-products, in particular lower hydrocarbons, particularly preferably methane,

[0071] Separation of unreacted carbon dioxide from the gas mixture obtained from the separation of the RWGS reaction, in particular by means of amine scrubbing, and recycling of the unreacted carbon dioxide to the RWGS reaction,

[0072] Separation of the hydrogen not converted in the RWGS reaction from the gas mixture of carbon monoxide and hydrogen obtained after the separation, in particular using a cold box, and optionally recycling the hydrogen into the RWGS reaction or feeding the hydrogen into the hydrogenation of the organic nitro compounds,

[0073] Feeding the remaining carbon monoxide from the separation into the phosgene synthesis.

[0074] The organic amino compounds prepared by the process according to the invention are, as described above, preferably suitable for the synthesis of organic isocyanate. In a further preferred embodiment of the process according to the invention, at least the following steps are additionally carried out for the synthesis of organic isocyanate: iv) synthesis of phosgene from at least carbon monoxide and chlorine gas (8b); v) isocyanate production from organic isocyanate by reacting at least the phosgene with the at least one organic amino compound, with the release of hydrogen chloride, wherein at least the following steps are carried out for the production of carbon monoxide:

[0075] Purification of a CO2 gas stream from secondary components, in particular nitrogen oxides, sulphur compounds, dust, water, oxygen and HCl, optionally by means of adsorption, gas scrubbing or catalytic treatment to obtain purified carbon dioxide,

[0076] Feeding of hydrogen gas provided from step ii) together with the purified CO2 gas stream into a RWGS reaction zone and conversion of the reactants according to the principle of the RWGS reaction to a product gas mixture of water vapor, CO and optionally by-products, in particular lower hydrocarbons, particularly preferably methane,

[0077] Separation of unreacted carbon dioxide from the gas mixture obtained from the separation of the RWGS reaction, in particular by means of amine scrubbing, and recycling of the unreacted carbon dioxide to the RWGS reaction,

[0078] Separation of the hydrogen not converted in the RWGS reaction from the gas mixture of carbon monoxide and hydrogen obtained after the separation, in particular using a cold box, and optionally recycling the hydrogen into the RWGS reaction or feeding the hydrogen into the hydrogenation of the organic nitro compounds,

[0079] Feeding the remaining carbon monoxide from the separation into the phosgene synthesis.

[0080] The CO2 source for providing carbon monoxide for the aforementioned steps A) and / or B) and / or C) can be, for example, the CO2 emitted when providing heat energy for steps B) or C), the CO2 emitted during air separation for the provision of nitrogen for the provision of ammonia or CO2 from an external CO2 source.

[0081] As an external CO2 source that contributes CO2 that is not emitted by the process according to the invention or its embodiments. An external CO2 source would be, for example, the CO2 that is produced in the exhaust gas during cement production or during the combustion of fuels (e.g. waste incineration), or CO2 that is obtained from the air. This CO2 from an external CO2 source is obtained in a preferred embodiment of the process according to the invention by absorbing a CO2 portion from (i) process gases or exhaust gases selected from at least one process selected from cement production, ^ production, combustion and / or (ii) from air by introducing it into alkali metal hydroxide solution, for example potassium hydroxide solution. This forms potassium bicarbonate, which can then be thermally decomposed back into CO2 and potassium hydroxide solution. The CO2 released in this process is then fed to the inventive process for the synthesis of carbon monoxide.

[0082] The RWGS reaction is preferably carried out in the presence of at least one catalyst. This is particularly preferably selected from at least one compound from the group:

[0083] (I) Mixed metal oxides of the formula A(i- W-X )A waA" x B(iy Z )B' y B" z O3-deita where:

[0084] A, A' and A" are independently selected from the group: Mg, Ca, Sr, Ba, Li, Na, K, Rb, Cs, Sn, Sc, Y, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Ti, Lu, Ni, Co, Pb, Bi and / or Cd; and

[0085] B, B' and B" are independently selected from the group: Cr, Mn, Fe, Bi, Cd, Co, Cu, Ni, Sn, Al, Ga, Sc, Ti, V, Nb, Ta, Mo, Pb, Hf, Zr, Tb, W, Gd, Yb, Mg, Li, Na, K, Ce and / or Zn; and

[0086] 0 'S w 'S 0.5; 0'S x < 0.5; 0 0.5; 0 0.5 and - 1 'S delta 'SI ;

[0087] (II) Mixed metal oxides of the formula A(i. w-X)A'wa" x B(iy Z )B'yB" z O3-deita where:

[0088] A, A' and A" are independently selected from the group: Mg, Ca, Sr, Ba, Li, Na, K, Rb, Cs, Sn, Sc, Y, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Ti, Lu, Ni, Co, Pb and / or Cd; and

[0089] B is selected from the group: Cr, Mn, Fe, Bi, Cd, Co, Cu, Ni, Sn, Al, Ga, Sc, Ti, V, Nb, Ta, Mo, Pb, Hf, Zr, Tb, W, Gd, Yb, Mg, Cd, Zn, Re, Ru, Rh, Pd, Os, Ir and / or Pt; and

[0090] B' is selected from the group: Re, Ru, Rh, Pd, Os, Ir and / or Pt; and B" is selected from the group: Cr, Mn, Fe, Bi, Cd, Co, Cu, Ni, Sn, Al, Ga, Sc, Ti, V, Nb, Ta, Mo, Pb, Hf, Zr, Tb, W, Gd, Yb, Mg, Cd and / or Zn; and

[0091] 0 'S w 'S 0.5; 0 0.5; 0 0.5; 0 0.5 and - 1 'S delta 'S 1 ;

[0092] (III) mixtures of at least two different metals M1 and M2 on a support which comprises an oxide of Al, Ce and / or Zr doped with a metal M3; where: M1 and M2 are independently selected from the group: Re, Ru, Rh, Ir, Os, Pd and / or Pt; and M3 is selected from the group: Sc, Y, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb and / or Lu;

[0093] (IV) Mixed metal oxides of the formula LO x (M( y / Z )AI(2-y / z)O3)z; where:

[0094] L is selected from the group: Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sc, Y, Sn, Pb, Pd, Mn, In, Ti, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb and / or Lu; and

[0095] M is selected from the group: Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Zn, Cu, Ag and / or Au; and

[0096] (V) Mixed metal oxides of the formula LO(AhO3)z; where:

[0097] L is selected from the group: Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sc, Y, Sn, Pb, Mn, In, Ti, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb and / or Lu; and

[0098] (VI) oxide catalyst comprising Ni and Ru.

[0099] (VII) metal M1 and / or at least two different metals M1 and M2 on and / or in a support, wherein the support is a carbide, oxycarbide, carbonitride, nitride, boride, silicide, germanide and / or selenide of the metals A and / or B; where:

[0100] M1 and M2 are independently selected from the group: Cr, Mn, Fe, Co, Ni, Re, Ru, Rh, Ir, Os, Pd, Pt, Zn, Cu, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, and / or Lu; and

[0101] A and B are independently selected from the group: Be, Mg, Ca, Sc, I i, V, Cr, Mn, Fe, Co, Ni, Y, Zr, Nb, Mo, Hf, Ta, W, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, and / or Lu; and / or

[0102] Reaction products of (I), (II), (III), (IV), (V), (VI) and / or (VII) in the presence of carbon dioxide, hydrogen, carbon monoxide and / or water at a temperature of

[0103] 700 °C.

[0104] Particularly preferred is a process according to the invention in the embodiment with phosgene production for the isocyanate synthesis and a pyrolysis of organic material for the production of the organic compounds used in step i-2), in which, to provide carbon monoxide, the residue from the gasification is converted into carbon dioxide in a combustion and the optionally purified carbon dioxide is introduced into the process for providing carbon monoxide.

[0105] Particularly preferred is therefore an embodiment of the process according to the invention in which additionally at least one organic compound used in step i-2) is an aromatic organic compound which is provided as a direct process product of a process comprising at least the following steps:

[0106] Pyrolysis of organic material at a temperature of 600 to 1000°C to obtain gaseous pyrolysate and pyrolysis residue;

[0107] Contacting the gaseous pyrolysate with a heterogeneous catalyst to obtain a conversion product containing at least one aromatic organic compound having a molecular weight of less than 300 g / mol;

[0108] Processing the conversion product to obtain said aromatic organic compound, in particular selected from benzene, toluene or xylene; additionally carrying out the following steps:

[0109] Gasification of the pyrolysis residue from the pyrolysis of organic material to at least carbon monoxide, which is fed into the synthesis of phosgene;

[0110] Conversion of the residue from the gasification into carbon dioxide by combustion and introduction of the optionally purified carbon dioxide into a process for providing carbon monoxide for the phosgene synthesis, selected from

[0111] A) the electrochemical reduction of CO2 using electrical energy produced from renewable energy,

[0112] B) a reforming process in which methane and steam are converted into carbon monoxide with the addition of at least CO2 and with the addition of heat energy at a temperature of at least 500°C,

[0113] C) Conversion of hydrogen and CO2 to carbon monoxide in a reverse water-gas shift RWGS reaction zone.

[0114] Another object of the invention is an apparatus configured for producing organic amino compounds for producing organic isocyanate compounds.This device configuration provides that the device part for providing nitric acid is filled with nitric acid which is a direct process product of a process for producing nitric acid, which comprises at least the following steps: a) Providing hydrogen gas and oxygen gas by carrying out a water electrolysis in an electrolysis device using electrical energy produced from renewable energy and water; b) Producing ammonia by reacting at least nitrogen and hydrogen gas from said water electrolysis in an ammonia synthesis; c) Producing nitric acid by reacting previously produced ammonia in a nitric acid production process at least with oxygen-containing gas, preferably at least one oxygen-containing gas selected from oxygen from said water electrolysis, air or oxygen from an air separation process.

[0115] In detail, the invention thus provides a device which is configured for producing organic amino compounds, wherein the device contains at least one device for providing hydrogen gas, at least one device for producing organic nitro compounds, at least one device for hydrogenating organic nitro compounds and at least one supply of nitric acid, wherein

[0116] - the at least one device for providing nitric acid contains at least one outlet for nitric acid and at least one inlet for nitric acid and at least one volume for nitric acid;

[0117] - the at least one device for producing organic nitro compounds contains at least one reactor, at least one inlet for organic compounds, at least one inlet for nitric acid and at least one outlet for organic nitro compounds;

[0118] - the at least one device for hydrogenating organic nitro compounds contains at least one reactor, at least one inlet for organic nitro compounds, at least one inlet for hydrogen gas and at least one outlet for organic amino compounds; characterized in that for the configuration i) the volume for nitric acid is filled with a nitric acid which is a direct process product of a process for nitric acid production which comprises at least the following steps: a) providing hydrogen gas and oxygen gas by carrying out a water electrolysis in an electrolysis device using electrical energy produced from renewable energy and water; b) producing ammonia by reacting at least nitrogen and hydrogen gas from said water electrolysis in an ammonia synthesis;c) production of nitric acid by reacting previously produced ammonia in a nitric acid production facility with at least oxygen-containing gas, preferably at least one oxygen-containing gas selected from oxygen from said water electrolysis, air or oxygen from air separation; ii) the nitric acid outlet of the device for providing nitric acid is in fluid communication with the nitric acid inlet of the device for producing organic nitro compounds; iii) the organic nitro compound outlet of the device for producing organic nitro compounds is in fluid communication with the organic nitro compound inlet of the device for hydrogenating organic nitro compounds; iv) the hydrogen gas inlet of the device for hydrogenating organic nitro compounds is in fluid communication with the hydrogen gas outlet of the device for providing hydrogen gas.

[0119] The volume for nitric acid of the device for providing nitric acid can, for example, be the volume of a storage container or the volume of a pipeline. If said volume is a storage container, it is preferred within the scope of a further embodiment if the device additionally provides at least one unloading device for transport containers, which is in fluid communication with the inlet for nitric acid of the device for providing nitric acid.

[0120] However, in a particularly preferred embodiment of the device according to the invention, the device is characterized in that the volume for nitric acid is a pipeline and the inlet for nitric acid of the device for providing nitric acid is in fluid communication with the outlet of a device for producing nitric acid.

[0121] Furthermore, it has been found to be preferable for the purposes of the process according to the invention if the provision of hydrogen gas for the hydrogenation of organic nitro compounds takes place using at least one electrolysis device selected from at least one electrolysis device for producing hydrogen gas from the group consisting of an electrolysis device for water, an electrolysis device for alkali chloride, and an electrolysis device for hydrochloric acid. For example, the electrolysis device for water integrated to provide hydrogen gas for one embodiment of the nitric acid provision can also be used accordingly to provide hydrogen gas for the hydrogenation device and can be integrated accordingly into the overall device.

[0122] The device according to the invention for providing organic amino compounds is preferably a component of a device for providing organic isocyanate compounds and is characterized in this embodiment in that the outlet for organic amino compounds of the device for hydrogenating organic nitro compounds is in fluid communication with an inlet for organic amino compounds of a device for phosgenation, said device for phosgenation containing at least one inlet for phosgene, at least one inlet for organic amino compounds and at least one outlet for organic isocyanate compounds.

[0123] A further object of the invention is the use of nitric acid, which is a direct process product of a process for nitric acid production, which comprises at least the following steps: a) providing hydrogen gas and oxygen gas by carrying out a water electrolysis in an electrolysis device using electrical energy produced from renewable energy and water; b) providing ammonia by reacting at least nitrogen and hydrogen gas from said water electrolysis (5) in an ammonia synthesis; c) producing nitric acid by reacting previously produced ammonia in a nitric acid production process at least with oxygen-containing gas, preferably at least one oxygen-containing gas selected from oxygen from said water electrolysis, air or oxygen from an air separation process; for producing organic amino compounds for the synthesis of organic isocyanate compounds.The invention is explained in more detail below with reference to Figures 1 to 6.

[0124] Fig.7 shows a process according to the prior art. In the figures, the following reference symbols have the meaning on the right:

[0125] 1 Phosgene synthesis

[0126] 1a Phosgen

[0127] 2 Isocyanate production

[0128] 3 Provision of hydrogen gas (especially from water electrolysis 5 as

[0129] Hydrogen 5a or from water electrolysis 3b)

[0130] 3a Hydrogen gas taken from the supply of hydrogen gas

[0131] 3b Water electrolysis

[0132] 3c O2 taken from water electrolysis 3b the provision of hydrogen gas 3

[0133] 4 CO2 gas, purified

[0134] 5 Water electrolysis

[0135] 5a Provision of hydrogen gas from water electrolysis 5

[0136] 5b Oxygen gas from water electrolysis 5

[0137] 5c Water for water electrolysis 5

[0138] 5d Hydrogen gas from water electrolysis

[0139] 5e Oxygen-containing gas for HNO3 synthesis (preferably from water electrolysis and / or air separation and / or air)

[0140] 5f Oxygen gas (O2) from air separation

[0141] 6 Reformer process with RWGS (Reverse-Water Gas-Shift) for CO production from hydrogen 3a and carbon dioxide (not shown, possibly also from 27)

[0142] 6a Reformer process with water gas shift for H2 production from methane and water

[0143] 6b Reformer process in a steam methane reformer reactor for CO production from methane and water

[0144] 7 Carbon monoxide CO

[0145] 8 Chlorine synthesis

[0146] 8a H2 from chlorine production

[0147] 8b CI2 from chlorine production

[0148] 9 Renewable energy for water electrolysis 3b

[0149] 10 Renewable energy for water electrolysis 5

[0150] 11 Renewable energy for chlorine electrolysis 8

[0151] 12 Renewable energy for air separation 23

[0152] 13 Residue from pyrolysis 25

[0153] 14 CO from gasification 26

[0154] 15 Residue from gasification 26 16 Organic material End of Life, preferably polyurethane-containing material End of Life

[0155] 17 Organic amine, e.g. diaminotoluene

[0156] 18 Organic isocyanate, e.g. toluene diisocyanate (TDI)

[0157] 19 Production of organic nitro compound

[0158] 19a Organic nitro compound, e.g. dinitrotoluene

[0159] 19b Organic compound to be nitrated from pyrolysis 25

[0160] 19c Organic compound to be nitrated, e.g. toluene

[0161] 20 Hydrogenation of nitro compound

[0162] 21 Ammonia synthesis

[0163] 21a Nitrogen for ammonia synthesis

[0164] 21b Provision of ammonia

[0165] 22 Nitric acid production

[0166] 22a Provision of nitric acid

[0167] 23 N2 provision by air separation

[0168] 24 Air for HNO3 production

[0169] 25 Pyrolysis of organic material, especially polyurethane material

[0170] 26 Gasification of organic material, e.g. residues from pyrolysis 25

[0171] 26a H2 from gasification 26

[0172] 27 Combustion

[0173] 27a CO2 gas, purified from combustion 27

[0174] 28 Process gas treatment

[0175] Arrows in the figures symbolize the flow of materials, energy, or heat between process steps or device components in which the corresponding process steps take place. Process features drawn with dashed lines symbolize additional features of further, preferred embodiments.

[0176] Arrows with dotted lines symbolize the provision of a substance. Provision can be achieved by supplying it from one process step to the next in a sealed transport container or by a material flow via a fluid connection. Arrows with solid lines connecting two process steps symbolize a material flow of the designated substance, which is transported via a fluid connection in the direction of the arrow between the process steps connected by the arrow.

[0177] In Fig. 1, a production of organic amino compounds by hydrogenation of organic nitro compound 20 is illustrated by way of example, in which first organic nitro compounds 19a and hydrogen 3a from a supply of hydrogen 3 are converted to organic amino compounds 17, wherein the produced organic nitro compounds 19a are produced in a production of organic nitro compounds 19, in which organic compounds 19c and nitric acid are reacted and the nitric acid 22a provided for this purpose is a direct process product of a production of nitric acid 22, in which the hydrogen produced from a water electrolysis 5 using water 5c and regenerative energy 10,and ammonia 21b provided from nitrogen 21a (preferably originating from an air separation 23) is reacted with oxygen-containing gas 5e (such as air 24 or oxygen 5b from the water electrolysis 5 or oxygen 5f from the air separation 23) to form nitric acid. The ammonia 21b provided and the nitric acid 22a provided are preferably produced by the corresponding processes at the same location as the organic amino compounds and are each provided via a fluid connection as a material stream for the respective further reactions. In this case, the excess hydrogen 5a from the water electrolysis 5 can be used to provide hydrogen 3 for the introduction of hydrogen 3a into the hydrogenation of nitro compounds 20 and can be introduced via a fluid connection.

[0178] According to Fig. 1, the variant of having the nitric acid produced decentrally according to the aforementioned processes is also possible in order to have it delivered in a transport container according to the provision of nitric acid 22a for the production of organic nitro compound 19. This variant is illustrated in Fig. 2, in which the ammonia for providing ammonia 21b is provided and introduced via a fluid connection for the production of nitric acid 22.

[0179] However, according to Fig.1 and as illustrated in Fig.3, it is also possible to have the ammonia produced, for example, decentrally according to the aforementioned process in order to have it supplied to provide ammonia 21b in a transport container, with the aim of converting this ammonia into nitric acid in the provision of nitric acid 22, which is then provided and introduced into the production of organic nitro compounds 19 via a fluid connection.

[0180] The process illustrated in Fig. 1 for the production of organic amino compounds can be incorporated into a conversion of these organic amino compounds to organic isocyanate compounds. Here, the organic amino compound 17 obtained from the hydrogenation of organic nitro compound 20 is introduced into a phosgenation 2 and reacted with phosgene 1a to form organic isocyanate compound 18. The phosgene 1a used for this purpose is produced in a phosgene production 1 from chlorine 8b and carbon monoxide 7, wherein the carbon monoxide 7 is produced from hydrogen 3a and carbon dioxide (supply not shown) by a reformer process with RWGS 6. The hydrogen 3a originates from the provision of hydrogen gas 3, preferably from a water electrolysis 3b of water using electricity from renewable energy 9 in the case of Figs. 2 and 3 with decentralized provision of ammonia or nitric acid.When ammonia and nitric acid are provided via a fluid connection, water electrolysis 5 is preferably used to provide hydrogen gas 3a.

[0181] The chlorine 8b is provided according to Fig. 1 to 3 by a chlor-alkali electrolysis 8 using electricity from renewable energy 11, wherein the hydrogen 8a possibly formed in this process is removed to provide hydrogen 3 and used for the hydrogenation of organic nitro compound 20.

[0182] In Figs. 1 to 3, carbon monoxide 14 is preferably additionally produced from a gasification of organic material 26, particularly preferably from residue 13 from the pyrolysis of organic material 25. For the gasification 26, the oxygen 3c from the water electrolysis (3b) is preferably used. The residues 15 from the gasification 26 are in turn preferably converted into carbon dioxide in a combustion process, using oxygen from the 3c from the water electrolysis (3b). The resulting carbon dioxide is purified and fed as purified carbon dioxide 27a to the reformer process with RWGS 6. The hydrogen 26a from the gasification 26 is used to provide hydrogen 3.

[0183] According to Fig.1 to 3, the organic compounds 19c for the nitration of organic compounds 19 can originate at least partially from a pyrolysis 25 of organic waste material 16, preferably plastic waste, in particular polyurethane material waste.

[0184] Fig.4 illustrates the overall process of Example 1 according to the invention (see there).

[0185] Fig. 5 and 6 represent variants of Example 1 of Fig. 4, in which, analogous to Fig. 2 and Fig. 3 respectively, the ammonia and the nitric acid are provided decentrally according to the above-mentioned process.

[0186] Fig. 7 illustrates Example 2 according to the prior art. Further embodiments of the invention include the following aspects I to XXVI:

[0187] I. A process for producing an organic amino compound for the synthesis of organic isocyanate compounds, comprising at least the steps i) providing at least one organic nitro compound (19a) as a process product of a process for synthesizing (19) at least one organic nitro compound (19a), which comprises at least the following steps: i-1) providing nitric acid (22a) as a process product of a process for producing nitric acid, which comprises at least the following steps: a) providing hydrogen gas (5d) and oxygen gas (5b) by carrying out a water electrolysis (5) in an electrolysis device using electrical energy (10) produced from renewable energy and water (5c); b) providing ammonia (21b) as a process product of a reaction of at least nitrogen (21a) and hydrogen gas (5d) from said water electrolysis (5) in an ammonia synthesis (21);c) production of nitric acid (22b) by reacting previously provided ammonia (21b) in a nitric acid production facility (22) at least with oxygen-containing gas (5e); i-2) synthesis (19) of at least one organic nitro compound (19a), preferably at least one aromatic organic nitro compound (19a), at least by nitration of at least one organic compound (19b, 19c), preferably at least one aromatic organic compound (19b, 19c), with at least the said provided nitric acid (22a); ii) provision (3) of hydrogen gas (3a), preferably by carrying out water electrolysis in an electrolysis device (3b) using electrical energy produced from renewable energy (9);iii) introducing the at least one provided organic nitro compound (19a) and the provided hydrogen gas into a hydrogenation (20) and subsequent hydrogenation (20) by reducing nitro groups of said at least one organic nitro compound (19a) by reacting them with said hydrogen gas (3a) to obtain at least one organic amino compound (17), preferably at least one aromatic organic amino compound (17);

[0188] II. Process according to aspect I, characterized in that the organic nitro compound (19a) is provided as a process product of said synthesis (19) of step i-2) in the form of a material stream directly via a fluid connection from said synthesis (19) via an optionally necessary intermediate storage in at least one storage container, wherein said synthesis (19), the optionally necessary at least one storage container and the hydrogenation (20) according to step iii) are in fluid communication with one another.

[0189] III. Process according to aspect I, characterized in that the organic nitro compound (19a) of step i-2) is provided as a process product of said synthesis (19) in a mobile, closed transport container, optionally transferred therefrom for intermediate storage into storage containers, wherein said synthesis (19) and the hydrogenation (20) according to step iii) are not in fluid communication with each other.

[0190] IV. Process according to one of aspects I to III, characterized in that in step i-1) the nitric acid (22b) is provided as a process product of said nitric acid production (22) in the form of a material stream directly via a fluid connection from said nitric acid production (22) via a possibly necessary intermediate storage in at least one storage container, wherein said nitric acid production (22), the possibly necessary at least one storage container and the synthesis (19) according to step i-2) are connected to one another via a fluid connection.

[0191] V. Process according to aspect IV, characterized in that in step i-1), the ammonia (21b) is provided as a process product of said ammonia production (21) in a mobile, closed transport container, optionally transferred therefrom for intermediate storage into storage containers, wherein said ammonia production (21) and the nitric acid production (22) are not in fluid communication with one another. VI. Process according to aspects I to III, characterized in that in step i-1), the nitric acid (22b) is provided as a process product of said nitric acid production (22) in a mobile, closed transport container, optionally transferred therefrom for intermediate storage into storage containers, wherein said nitric acid production (22) and the synthesis (19) according to step ii) are not in fluid communication with one another.

[0192] VII. Process according to one of aspects I to VI, characterized in that the nitric acid (22a) provided in step i-1) is a process product of a nitric acid production (22) in which the nitrogen (21a) used to produce ammonia (21b) in step b) is provided by an air separation (23).

[0193] VIII. Process according to one of aspects I to VII, characterized in that the nitric acid (22a) provided in step i-1) is a process product of a nitric acid production (22) in which at least one oxygen-containing gas (5e) selected from oxygen (5b) from a water electrolysis (5, 3b), air (24) or oxygen (5f) from an air separation (23) is used for the oxidation reaction of step c).

[0194] IX. Process according to one of aspects VII or VIII, characterized in that the nitric acid (22a) provided in step i-1) is a process product of a nitric acid production (22) in which, for the oxidation reaction of step c), oxygen for the oxygen-containing gas (5f) is provided by an air separation (23), in particular an air separation (23) which also supplies nitrogen (21a) for step b) according to aspect 5.

[0195] X. Process according to one of aspects I to IX, characterized in that the hydrogen provided in step ii) is produced at least by electrolysis of water (3b) using electrical energy (9), wherein the provision of electrical energy (9) is used as regenerative energy optionally wind power, solar energy, hydropower or mixtures thereof.

[0196] XI. Process according to one of the preceding aspects, characterized in that the organic compound (19b, 19c) used in step i-2) is selected from benzene or toluene. XII. Process according to one of the preceding aspects, characterized in that at least one organic compound (19c) used in step i-2) is an aromatic organic compound (19b) provided as a direct process product of a process comprising at least the following steps:

[0197] Pyrolysis (25) of organic material at a temperature of 600 to 1000°C to obtain gaseous pyrolysate and pyrolysis residue (13);

[0198] Contacting the gaseous pyrolysate with a heterogeneous catalyst to obtain a conversion product containing at least one aromatic organic compound having a molecular weight of less than 300 g / mol;

[0199] Working up the conversion product to obtain said aromatic organic compound (19b), in particular selected from benzene, toluene or xylene.

[0200] XIII. Process according to aspect XII, characterized in that the pyrolysis residue (13) obtained during the pyrolysis (25) is converted in a gasification (26) under partial oxidation to carbon monoxide (14), hydrogen (26a) and residue (15) and the carbon monoxide (14) formed, after optional workup, is introduced into the phosgene synthesis (1) and the hydrogen (26a) is introduced into the provision of hydrogen (3).

[0201] XIV. Process according to any one of the preceding aspects, characterized in that the organic amino compound (17) obtained in step iii) is selected from tolylenediamine (TDA), methylenedi(phenylamine) (MDA) (in turn preferably selected from diphenylmethane-2,2'-diamine, diphenylmethane-2,4'-diamine, diphenylmethane-4,4'-diamine or mixtures thereof) or mixtures thereof.

[0202] XV. Process according to one of the preceding aspects, characterized in that for the synthesis of organic isocyanate, at least the following steps are additionally carried out: iv) synthesis (1) of phosgene (1a) from at least carbon monoxide (7) and chlorine gas (8b); v) isocyanate production (2) of organic isocyanate (18) by reacting at least the phosgene (1a) with the at least one organic amino compound (17), with the release of hydrogen chloride. XVI. Process for the synthesis of organic isocyanate (18), comprising at least the steps

[0203] Providing at least one organic amino compound (17) as a process product of a process according to one of aspects I to XIV;

[0204] Synthesis (1) of phosgene (1a) from at least carbon monoxide (7) and chlorine gas (8b);

[0205] Isocyanate production (2) of organic isocyanate (18) by reacting at least the phosgene (1a) with the at least one organic amino compound (17), with release of hydrogen chloride.

[0206] XVII. Method according to one of the aspects XV or XVI, characterized in that the carbon monoxide (7) is produced from CO2, at least by at least one method (6) selected from

[0207] A) the electrochemical reduction of CO2 using electrical energy produced from renewable energy,

[0208] B) a reforming process in which bio-methane and steam are converted into carbon monoxide with the addition of at least CO2 and with the addition of heat energy at a temperature of at least 500°C,

[0209] C) Conversion of hydrogen and CO2 to carbon monoxide in a reverse water-gas shift RWGS reaction zone.

[0210] XVIII. Process according to aspect XVII, characterized in that the residual material (15) from the gasification (26) according to aspect 12 is converted into carbon dioxide in a combustion (27) and the optionally purified carbon dioxide is introduced into the process (6) for providing carbon monoxide.

[0211] XIX. Method according to one of the aspects XIII to XVIII, characterized in that chlorine gas (8b) is provided at least by at least one chlorine synthesis (8) selected from

[0212] A) an oxidative conversion of the separated and purified hydrogen chloride from the isocyanate production (2) in a thermocatalytic gas phase oxidation with oxygen to chlorine and water,

[0213] B) a reaction of the hydrogen chloride from the isocyanate production (2) with water to form hydrochloric acid and electrochemical oxidation of the hydrochloric acid to chlorine (8b) and optionally hydrogen (8a). XX. Use of nitric acid, which is a direct process product of a process for nitric acid production, comprising at least the following steps: a) providing hydrogen gas (5d) and oxygen gas (5b) by carrying out a water electrolysis (5) in an electrolysis device using electrical energy (10) produced from renewable energy and water (5c); b) providing ammonia (21b) by reacting at least nitrogen (21a) and hydrogen gas (5d) from said water electrolysis (5) in an ammonia synthesis (21);c) producing nitric acid (22b) by reacting previously produced ammonia (21b) in a nitric acid production facility (22) with at least one oxygen-containing gas (5e), ​​preferably at least one oxygen-containing gas selected from oxygen (5b) from said water electrolysis (5), air (24), or oxygen (5f) from an air separation facility (23); for producing organic amino compounds for the synthesis of organic isocyanate compounds.;

[0214] XXI. A device configured for producing organic amino compounds, the device comprising at least one device for providing hydrogen gas, at least one device for producing organic nitro compounds, at least one device for hydrogenating organic nitro compounds, and at least one source of nitric acid, the at least one device for providing nitric acid comprising at least one outlet for nitric acid, at least one inlet for nitric acid, and at least one volume for nitric acid; the at least one device for producing organic nitro compounds comprising at least one reactor, at least one inlet for organic compounds, at least one inlet for nitric acid, and at least one outlet for organic nitro compounds;the at least one device for hydrogenating organic nitro compounds contains at least one reactor, at least one inlet for organic nitro compounds, at least one inlet for hydrogen gas, and at least one outlet for organic amino compounds; characterized in that i) the storage container for providing nitric acid is filled with nitric acid which is a direct process product of a process for producing nitric acid, which comprises at least the following steps: a) providing hydrogen gas (5d) and oxygen gas (5b) by carrying out a water electrolysis (5) in an electrolysis device using electrical energy (10) produced from renewable energy and water (5c); b) producing ammonia (21b) by reacting at least nitrogen (21a) and hydrogen gas (5d) from said water electrolysis (5) in an ammonia synthesis (21);c) producing nitric acid (22b) by reacting previously produced ammonia (21b) in a nitric acid production facility (22) at least with oxygen-containing gas (5e), ​​preferably at least one oxygen-containing gas selected from oxygen (5b) from said water electrolysis (5), air (24) or oxygen (5f) from an air separation facility (23); ii) the nitric acid outlet of the device for providing nitric acid is in fluid communication with the nitric acid inlet of the device for producing organic nitro compounds; iii) the organic nitro compound outlet of the device for producing organic nitro compounds is in fluid communication with the organic nitro compound inlet of the device for hydrogenating organic nitro compounds;iv) the hydrogen gas inlet of the device for hydrogenating organic nitro compounds is in fluid communication with the hydrogen gas outlet of the device for providing hydrogen gas;

[0215] XXII. Device according to aspect XXI, characterized in that the device for providing hydrogen gas (3) obtains the hydrogen gas from at least one electrolysis for producing hydrogen gas, selected from an electrolysis of water, an electrolysis of alkali chloride, an electrolysis of hydrochloric acid or from several of the aforementioned electrolyses.

[0216] XXIII. Device according to aspect XXI or XXII, characterized in that the volume for nitric acid of the device for providing nitric acid is the volume of a storage container or the volume of a pipeline.

[0217] XXIV. Apparatus according to aspect XXIII, characterized in that the volume for nitric acid is a storage container and the nitric acid inlet of the device for providing nitric acid is in fluid communication with a transport container unloading device.

[0218] XXV. Apparatus according to aspect XXIII, characterized in that the volume for nitric acid is a pipeline and the nitric acid inlet of the device for providing nitric acid is in fluid communication with the outlet of a device for producing nitric acid.

[0219] XXVI. Apparatus according to any one of aspects XXI to XXV, characterized in that the outlet for organic amino compounds of the apparatus for hydrogenating organic nitro compounds is in fluid communication with an inlet for organic amino compounds of a phosgenation apparatus, said phosgenation apparatus containing at least one inlet for phosgene, at least one inlet for organic amino compounds, and at least one outlet for organic isocyanate compounds.

[0220] Examples

[0221] The following process parameters result from the data of the individual process steps as a material flow of the overall process:

[0222] Example 1 - State of the art (Fig.7)

[0223] Toluene diisocyanate (TDI) is produced according to the state of the art as follows. Figure 7 illustrates the process.

[0224] Carbon monoxide (CO) 7 and hydrogen (H2) are produced via a steam methane reforming process 6b (SMR). For this purpose, 6.89 t / h of methane from natural gas are fed to an SMR reactor 6b, along with 19.0 t / h of water. In an internal circuit, 3.73 t / h of CO2 are recycled from the process gas treatment 28, which is located downstream of the SMR reactor (6). The gases emerging from the SMR reactor 6b are fed to a process gas treatment 28 for drying, CO2 separation, and CO-H2 separation. Technologically established processes are used for this purpose. From the process gas treatment 28, 11.36 t / h of carbon monoxide (CO) 7 as well as 2.31 t / h of hydrogen, 11.3 t / h of water, 3.73 t / h of CO2 and a residual gas of 0.92 t / h containing H2, CO and unreacted methane are separated. Of the hydrogen fed to the provision of hydrogen 3, 2.15 t / h of hydrogen 3a are fed to the hydrogenation 20 of the dinitrotoluenes 19a. The 0.16 t / h of hydrogen 3a from the SMR reactor 6b orits process gas treatment 28 are fed to the ammonia synthesis 21. 11.36 t / h of CO 7 are fed to the phosgene synthesis 1. Here, the CO 7 is reacted with chlorine 8b to form 35.56 t / h of phosgene 1a (COCl 2). In the hydrogenation 20, 32.68 t / h of dinitrotoluene 19a are reacted with 2.15 t / h of hydrogen 3a, with elimination of 12.93 t / h of water, to form 21.91 t / h of diaminotoluene 17. The diaminotoluene 17 is reacted with 35.56 t / h of phosgene 1a, with elimination of 26.22 t / h of hydrogen chloride, to form 31.24 t / h of toluene diisocyanate 18. From 16.52 t / h of toluene 19c, 22.62 t / h of HNO3 are reacted with nitric acid 22a, calculated as 100% HNO3, to give 32.68 t / h of dinitrotoluene 19a.

[0225] For more effective hydrogen production, an SMR reactor (6a) is used solely for H2 production, in which the produced CO is converted with water to H2 and CO2 by means of a water-gas shift reaction. 2.04 t / h of methane from natural gas and 7.78 t / h of water are fed to this process. 0.92 t / h of hydrogen, 5.28 t / h of CO2, and a residual gas of 0.26 t / h consisting of CO, H2, and by-products such as methane are obtained. The hydrogen, together with excess hydrogen 3a from the SMR 6 and the CO production of 0.16 t / h, is converted in an ammonia synthesis 21 with 5.03 t / h of N221a from an air separation 23 to produce 6.10 t / h of ammonia 21b using the Haber-Bosch process. Subsequently, the ammonia 21b is converted into nitric acid by combustion, ie by reaction with 22.98 t / h of oxygen 5f for the oxygen-containing gas 5e, which is fed to the production 19 of di-nitrotoluene by producing nitric acid 22a.

[0226] In this process, 5.28 t / h of CO2 are directly released from the hydrogen production used for NH3 production. The carbon from the isocyanate group in the organic isocyanate 18 comes from a fossil raw material source, natural gas, and is therefore not sustainable. The carbon from the isocyanate group accounts for 22% of the carbon in TDI.

[0227] Example 2 Inventive method - Entire process is located at one location (Fig. 4)

[0228] The process steps of Example 4 are all carried out at one location. The dotted arrows for 5a, 21b, and 22a in Fig. 4 indicate a fluid connection used to supply the respective substances according to this example and could also be symbolized with a solid line.

[0229] Inventive production of low-emission toluene diisocyanate (TDI), CO production in which CO2 and H2 are used as raw materials in a reformer process 6 (rWGS reverse water gas shift reaction). Optionally, the rWGS can be heated with renewable electrical energy or with bio-natural gas. The required hydrogen and the co-product oxygen are generated by water electrolysis 5. The hydrogen generated is provided 3. The hydrogen 5a from the water electrolysis 5 is partly converted as hydrogen 5d with nitrogen 21a from the air separation 23 according to the well-known Haber-Bosch process in the ammonia synthesis 21 to ammonia 21b. The ammonia 21b is converted with air 24 or O2, optionally oxygen 5f from the air separation 23 or also the oxygen 5b from the water electrolysis 5 in the production of nitric acid 22 to nitric acid.The remaining hydrogen 5a from the water electrolysis 5 is provided for the RWGS reformer 6 and the hydrogenation 20 of the nitroaromatics 19a 3. Renewable energy (10, 12) is used to operate the water electrolysis 5 as well as the air separation 23.

[0230] In a rWGS reaction chamber 6, which is operated at a temperature of 802°C, 17.84 t / h of CO2 and 0.81 t / h of H2 are introduced. From the rWGS reaction 6, the resulting product gas mixture, consisting of CO7, H2O, unreacted CO2 and unreacted H2, as well as by-products, mainly small amounts of methane, is removed and fed to a process gas treatment system (not shown) 28. Here, CO2 and water are separated, and CO is separated from H2, as well as residual gases.

[0231] A total of 4.04 t / h of hydrogen 5a and 32.32 t / h of O25b are extracted from water electrolysis 5, while 37 t / h of water 5c are fed to water electrolysis 5. If water electrolysis 5 is located at the site of the rWGS 6, isocyanate production 2, hydrogenation 20 and nitro compound production 19, NH3 synthesis 22, and HNO3 production 21, water from hydrogenation 22, the production of nitro compounds 21, and water electrolysis 5 can each be separated and fed to water electrolysis 5. This protects the water resource, a further step that improves the sustainability of the process according to the invention.

[0232] The gas stream withdrawn from rWGS 6 is separated in the process gas treatment. Here, 11.36 t / h of CO from the H2-CO separation is fed to a phosgene synthesis 1. For this purpose, the CO 7 is reacted with chlorine 8b to produce 35.56 t / h of phosgene 1a (COCl 2). In the hydrogenation 20, 32.68 t / h of dinitrotoluene 19a and 2.15 t / h of hydrogen 3a from the water electrolysis (5) are reacted to produce 21.91 t / h of diaminotoluene, with the elimination of 12.93 t / h of water. The diaminotoluene is reacted with 35.56 t / h of phosgene, with the elimination of 26.22 t / h of hydrogen chloride, to produce 31.24 t / h of toluene diisocyanate. From 16.52 t / h of toluene, 22.62 t / h of HNO3 are reacted with nitric acid, calculated as 100% HNO3, to produce 32.68 t / h of dinitrotoluene.

[0233] Water electrolysis (5) is used to produce H2. In the water electrolysis, 37 t / h of water are converted into 4.04 t / h of hydrogen and 32.32 t / h of oxygen. The hydrogen is fed to the rWGS (6) at a rate of 0.81 t / h, to the ammonia synthesis (21) at a rate of 1.08 t / h, and to the hydrogenation of nitro compounds (20) at a rate of 2.15 t / h.

[0234] The nitrogen 21a for the production of ammonia 21b in the NH3 synthesis 21 is obtained from the air separation 23, which is powered by renewable energy 12. From the air separation 23, 5.03 t / h of nitrogen 21a are fed to the ammonia synthesis 21, where it is reacted with 1.08 t / h of H25d from the water electrolysis 5 to produce 6.1 t / h of ammonia 21b. The ammonia is supplied via a fluid connection 21b from the ammonia synthesis 21 for the production of nitric acid 22.

[0235] In the production of nitric acid 22, the by-product oxygen 5b from water electrolysis 5 can be used to convert 6.1 t / h of ammonia 21b into 22.6 t / h of nitric acid, calculated as 100% acid. The nitric acid is fed to the production of the nitro compounds 19 via a fluid connection 22a. In this process, no direct CO2 emissions from hydrogen production are released. The carbon from the isocyanate group originates from CO2 and is thus introduced sustainably. This avoids the direct emissions of 6.29 t / h of CO2, and 22% of the carbon in the TDI is produced sustainably.

Claims

P a t e n t a n s p r ü c h e 1. A process for the preparation of organic amino compounds for the synthesis of organic isocyanate compounds, comprising at least the steps i) providing at least one organic nitro compound (19a) as a direct process product of a process for the synthesis (19) of at least one organic nitro compound (19a), which comprises at least the following steps: i-1) providing nitric acid (22a) as a direct process product of a process for nitric acid production, which comprises at least the following steps: a) providing hydrogen gas (5d) and oxygen gas (5b) by carrying out a water electrolysis (5) in an electrolysis device using electrical energy (10) produced from renewable energy and water (5c); b) providing ammonia (21b) as a direct process product of a reaction of at least nitrogen (21a) and hydrogen gas (5d) from said water electrolysis (5) in an ammonia synthesis (21); c) production of nitric acid by reacting previously provided ammonia (21b) in a nitric acid production (22) at least with oxygen-containing gas (5e); i-2) synthesis (19) of at least one organic nitro compound (19a), preferably at least one aromatic organic nitro compound (19a), at least by nitration of at least one organic compound (19b, 19c), preferably at least one aromatic organic compound (19b, 19c), with at least said provided nitric acid (22a); ii) provision (3) of hydrogen gas (3a), preferably by carrying out a water electrolysis in an electrolysis device (3b) using electrical energy produced from regenerative energy (9); iii) introduction of the at least one provided organic nitro compound (19a) and the provided hydrogen gas into a hydrogenation (20) and subsequent hydrogenation (20) by reducing nitro groups of said at least one organic nitro compound (19a) by reacting it with said hydrogen gas (3a) to obtain at least one organic amino compound (17), preferably at least one aromatic organic amino compound (17). The process according to claim 1, characterized in that the organic nitro compound (19a) is provided as a process product of said synthesis (19) of step i-2) in the form of a material stream directly via a fluid connection from said synthesis (19) via an optionally necessary intermediate storage in at least one storage container, wherein said synthesis (19), the optionally necessary at least one storage container, and the hydrogenation (20) according to step iii) are in fluid communication with one another.Process according to claim 1, characterized in that the organic nitro compound (19a) of step i-2) is provided as a process product of said synthesis (19) in a mobile, closed transport container, optionally transferred therefrom for intermediate storage into storage containers, wherein said synthesis (19) and the hydrogenation (20) according to step iii) are not in fluid communication with one another.Method according to one of claims 1 to 3, characterized in that in step i-1) the nitric acid is provided as a process product of said nitric acid production (22) in the form of a material stream (22a) directly via a fluid connection from said nitric acid production (22) via an optionally necessary intermediate storage in at least one storage container, wherein said nitric acid production (22), the optionally necessary at least one storage container and the synthesis (19) according to step i-2) are connected to one another via a fluid connection.Method according to claim 4, characterized in that in step i-1) the ammonia (21b) is provided as a process product of said production of ammonia (21) in a movable, closed transport container, optionally transferred therefrom for intermediate storage into storage containers, wherein said production of ammonia (21) and the nitric acid production (22) are not in fluid communication with one another. Process according to claims 1 to 3, characterized in that in step i-1), the nitric acid is provided as a process product of said nitric acid production (22) for provision (22a) in a movable, closed transport container, optionally transferred therefrom into storage containers for intermediate storage, wherein said nitric acid production (22) and the synthesis (19) according to step ii) are not in fluid communication with one another. Process according to one of claims 1 to 6, characterized in that the hydrogen provided in step ii) is produced at least by electrolysis of water (3b) using electrical energy (9), wherein the provision of electrical energy (9) is used as renewable energy, optionally wind power, solar energy, hydropower, or mixtures thereof.Process according to one of the preceding claims, characterized in that the organic amino compound (17) obtained in step iii) is selected from tolylenediamine (TDA), methylenedi(phenylamine) (MDA) (in turn preferably selected from diphenylmethane-2,2'-diamine, diphenylmethane-2,4'-diamine, diphenylmethane-4,4'-diamine or mixtures thereof) or mixtures thereof. Process according to one of the preceding claims, characterized in that for the synthesis of organic isocyanate, at least the following steps are additionally carried out: iv) synthesis (1) of phosgene (1a) from at least carbon monoxide and chlorine gas (8b); v) isocyanate production (2) of organic isocyanate (18) by reacting at least the phosgene (1a) with the at least one organic amino compound (17), with release of hydrogen chloride. Process for the synthesis of organic isocyanate (18), comprising at least the steps. Providing at least one organic amino compound (17) as a direct process product of a process according to any one of claims 1 to 8; Synthesis (1) of phosgene (1a) from at least carbon monoxide and chlorine gas (8b); Isocyanate production (2) from organic isocyanate (18) by reacting at least the phosgene (1a) with the at least one organic amino compound (17), with the release of hydrogen chloride. Process according to one of claims 9 or 10, characterized in that the carbon monoxide is produced from CO2, at least by at least one process (6) selected from A) the electrochemical reduction of CO2 using electrical energy produced from renewable energy, B) a reforming process in which methane and steam are converted into carbon monoxide with the addition of at least CO2 and with the addition of heat energy at a temperature of at least 500°C, C) Conversion of hydrogen and CO2 in a reverse water-gas shift (RWGS) reaction zone to carbon monoxide. Use of nitric acid, which is a direct process product of a process for producing nitric acid, comprising at least the following steps: a) Providing hydrogen gas (5d) and oxygen gas (5b) by carrying out a water electrolysis (5) in an electrolysis device using electrical energy (10) produced from renewable energy and water (5c); b) Providing ammonia (21b) by converting at least nitrogen (21a) and hydrogen gas (5d) from said water electrolysis (5) in an ammonia synthesis (21);c) producing nitric acid (22b) by reacting previously produced ammonia (21b) in a nitric acid production facility (22) at least with oxygen-containing gas (5e), ​​preferably at least one oxygen-containing gas selected from oxygen (5b) from said water electrolysis (5), air (24), or oxygen (5f) from an air separation facility (23); for producing organic amino compounds for the synthesis of organic isocyanate compounds. A device configured for producing organic amino compounds, the device comprising at least one device for providing hydrogen gas, at least one device for producing organic nitro compounds, at least one device for hydrogenating organic nitro compounds, and at least one source of nitric acid, wherein; the at least one device for providing nitric acid contains at least one outlet for nitric acid and at least one inlet for nitric acid and at least one volume for nitric acid; the at least one device for producing organic nitro compounds contains at least one reactor, at least one inlet for organic compounds, at least one inlet for nitric acid and at least one outlet for organic nitro compounds; the at least one device for hydrogenating organic nitro compounds contains at least one reactor, at least one inlet for organic nitro compounds, at least one inlet for hydrogen gas and at least one outlet for organic amino compounds;characterized in that i) the storage container for providing nitric acid is filled with nitric acid which is a direct process product of a process for producing nitric acid, which comprises at least the following steps: a) providing hydrogen gas (5d) and oxygen gas (5b) by carrying out a water electrolysis (5) in an electrolysis device using electrical energy (10) produced from renewable energy and water (5c); b) producing ammonia (21b) by reacting at least nitrogen (21a) and hydrogen gas (5d) from said water electrolysis (5) in an ammonia synthesis (21);c) producing nitric acid by reacting previously produced ammonia (21b) in a nitric acid production facility (22) at least with oxygen-containing gas (5e), ​​preferably at least one oxygen-containing gas selected from oxygen (5b) from said water electrolysis (5), air (24) or oxygen (5f) from an air separation facility (23); ii) the nitric acid outlet of the device for providing nitric acid is in fluid communication with the nitric acid inlet of the device for producing organic nitro compounds; iii) the organic nitro compound outlet of the device for producing organic nitro compounds is in fluid communication with the organic nitro compound inlet of the device for hydrogenating organic nitro compounds; iv) the hydrogen gas inlet of the device for hydrogenating organic nitro compounds is in fluid communication with the hydrogen gas outlet of the device for providing hydrogen gas. Device according to claim 13, characterized in that the device for providing hydrogen gas (3) obtains the hydrogen gas from at least one electrolysis for producing hydrogen gas, selected from an electrolysis of water, an electrolysis of alkali chloride, an electrolysis of hydrochloric acid, or several of the aforementioned electrolyses. Device according to claim 13 or 14, characterized in that the volume for nitric acid of the device for providing nitric acid is a volume of a storage container or the volume of a pipeline.The device according to claim 13 or 14, characterized in that the volume for nitric acid is a volume of a storage container, and the nitric acid inlet of the device for providing nitric acid is in fluid communication with a transport container unloading device. The device according to claim 13 or 14, characterized in that the volume for nitric acid is a pipeline, and the nitric acid inlet of the device for providing nitric acid is in fluid communication with the outlet of a device for producing nitric acid.Apparatus according to one of claims 13 to 17, characterized in that the outlet for organic amino compounds of the apparatus for hydrogenating organic nitro compounds is in fluid communication with an inlet for organic amino compounds of a phosgenation apparatus, said phosgenation apparatus containing at least one inlet for phosgene, at least one inlet for organic amino compounds and at least one outlet for organic isocyanate compounds.

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