PROCESS FOR THE PREPARATION OF ALKYLENE OXIDES

Description

[0001] The invention relates to a process for preparing an alkylene oxide by reacting an alkene with an arene oxide, pyridine N-oxide and / or pyrimidine N-oxide, preferably with an arene oxide and / or pyridine N-oxide in the presence of a catalyst in a first reactor, wherein the catalyst comprises a metal and / or a metal salt, wherein the metal is copper, silver and / or gold, wherein the metal salt comprises chromium, iron, cobalt and / or copper, cation(s), and wherein the reaction takes place in the absence of oxygen or an oxygen-containing gas mixture.

[0002] Numerous processes for the production of alkylene oxides, especially propylene oxide, have been described in the prior art. The chlorohydrin process is of particular industrial importance. In this process, propene is reacted with hypochlorous acid or chlorine and water to form an isomer mixture of 1-chloro-2-propanol and 2-chloro-1-propanol, which is then reacted with milk of lime to form propylene oxide and calcium chloride. However, the formation of CaCl2 salts results in high wastewater pollution, an additional recycling step, and integration into a chlor-alkali plant. This technology is considered disadvantageous with regard to the carbon footprint and greenhouse gas emissions (Reduction of GHG Emissions in Propylene Oxide Production, Approved VCS Methodology VM0023 Version 1.0, September 9, 2013, Sectoral Scope 5, South Pole Carbon Asset Management Ltd.).

[0003] In addition, the production of propylene oxide using co-product-based processes (e.g., oxirane processes) is relevant. In this process, ethylbenzene or isobutane are converted in a first step in the presence of oxygen to the respective hydroperoxides, which can then be reacted with propene to form propylene oxide and 1-phenylethanol or tert-butanol as further co-products. These co-products can then be further converted to styrene and isobutene or isobutane. However, in addition to propylene oxide, a co-product is also formed, which must be separated and further processed in additional plants. Co-product-based processes always require a sales market for the co-product, making the economics of such processes complex and susceptible to adverse effects.Thus, in addition to the technically demanding processes, there are also obvious market risks, so that a techno-economic analysis of these processes paints a less than favorable overall picture. This is especially true since the demand and sales situation for both products, PO and the co-product, generally varies regionally. This requires long-distance logistics, which entails direct costs and other disadvantages, such as CO2 / GHG emissions. The industrial MTBE process requires integration into a refinery operation to generate maximum economic benefits.

[0004] The so-called HPPO process, in which propylene is reacted with hydrogen peroxide to form propylene oxide and water, is also of industrial relevance. Its advantage over the aforementioned industrial production processes is that no byproducts or salt loads result in the product. However, hydrogen peroxide must be produced in an upstream, technically complex catalytic process. This process is considered technically demanding and is generally only operated at integrated sites with other H2O2 consumers.

[0005] The direct oxidation of propene to propylene oxide is still considered technically immature, and according to the current state of the art, there is no direct oxidation process that is economically viable industrially. In particular, the reaction process and, in particular, temperature control in gas-phase and molten salt processes remain an unsolved challenge. However, a high propene conversion combined with high PO selectivity is crucial for an efficient industrial process. During direct oxidation, a number of by-products and subsequent products, such as methanol, acetaldehyde, carbon dioxide, ethylene, and formaldehyde, occur in substantial quantities (cf. D. Kahlich et al., Dow Deutschland in Ullmann's Encyclopedia of Industrial Chemistry, chapter "Propylene Oxide", Wiley VCH, 2012). For example, US2018208569A1 and US2020346193A1 can be considered as current state-of-the-art documents for the aerobic oxidation of alkenes such as propene. Only 54.5% and60% epoxy selectivity is achieved at 8.6% and 5% conversion, respectively.

[0006] Arene oxides are key compounds in the oxidative metabolism of aromatic compounds. They can be prepared in high yields using enzymatic synthesis methods. Scientific publications that describe these processes in detail for synthetic purposes include "Enzymatic and chemoenzymatic synthesis of arene transdihydrodiols" in Journal of Molecular Catalysis B: Enzymatic, Volumes 19-20, 2, 2002, pp. 31-42, and "Chemical Equivalent of Arene Monooxygenases: Dearomative Synthesis of Arene Oxides and Oxepines" by Zohaib Siddiqi, William C. Wertjes, and David Sarlah, J. Am. Chem. Soc. 2020, 142, 22, 10125-10131. But also other synthesis methods such as direct epoxidation, preparation from trans-1,2-glycols, preparation from cis-1,2-glycols, preparation from bromohydrins, preparation from vicinal dihalogen compounds of epoxidized proaromatics, ring closure of secoDerivatives, electrochemical oxidation, conversion of annulenes, conversion of arene photooxides and / or peroxides, conversion of ozonide compounds, preparation from oxygen heterocycles and by intramolecular oxygen transfer reactions (intramolecular oxygen trapping) are suitable preparation processes (cf. e.g. GS Shirwaiker et al., Advances in Heterocyclic Chemistry, Vol. 37, 1984, 67-165).

[0007] Arene oxides are obtained by the oxidation of aromatic and polycyclic aromatic compounds. Hypochlorites are typically used as oxidants in combination with phase-transfer catalysts (see, for example, JP61109784). The reactions are carried out either in bulk or in solvent; chlorinated and nitrated hydrocarbons have proven particularly effective. pH control can be advantageous during the synthesis.

[0008] Arene oxides of various halogenated benzenes are also commercially available.

[0009] The selective oxidation of ternary nitrogen compounds is very well described. For example, processes using hydrogen peroxide and the use of methyltrioxorhenium(VII) (J. Org. Chem., 1995, 60, 1326), magnesium porphyrins (Synthesis, 1997, 1387), flavins (1980, 102, 6498), TS-1 and other zeolites (Catal. Lett., 2001, 72, 233), molecular sieves (Chem. Commun., 2000, 1577), polyoxometalates (J. Mol. Catalysis A: Chem. 252, 219-225, 2006; Green Chem., 2011, 13, 1486-1489) or tungsten-substituted Mg-Al layered hydroxides (Chem. Commun., 2001, 1736) as catalysts. In addition, other synthesis processes using various inorganic and organic oxidizing agents such as organic peracids, dioxiranes, peroxomonosulfuric acid ( Caroacid), peroxomonophosphoric acid, etc. (see, among others, Michael B. Smith, March's Advanced Organic Chemistry, 7th Edition, Wiley, 2012).

[0010] N-oxides of aromatic, N-heterocyclic compounds can be obtained by oxidation using oxygen and ruthenium(III) chloride as catalysts (SL Jain et al. Chem. Commun. 2002, 1040-1041). At 20 °C and 1 atm O2, N-oxides of pyridine, 2-, 3-, and 4-picolines, substituted pyridines, quinoline, and isoquinoline can be obtained in yields of up to 95%. The use of certain non-protic solvents and / or additional P ligands can positively influence the kinetics of the process.

[0011] CN108623519 describes the oxidation of pyridine with oxygen in isopropanol in the presence of a titanium-containing zeolite catalyst. This is a technically simple process, and high conversions and high yields are reported.

[0012] The use of N-oxides as oxidizing agents is known (cf., for example, Org. Synth. Coll. Vol., 1988, 6, 342; Chem. Rev., 1980, 80, 187; Org. Proc. Res. Dev., 1997, 1, 425; Synthesis, 1994, 639; Chem. Ber., 1961, 94, 1360; Bull. Chem. Soc. Jpn., 1986, 59, 3287; Tetrahedron Lett., 1990, 31, 4825; J. Chem. Soc., Chem. Commun., 1987, 1625). N-oxides are characterized as efficient carriers of atomic oxygen, whereby the original nitrogen compound is recovered. This can then be easily recycled or in situ be directly oxidized back to the corresponding N-oxide. When N-oxide oxidants are used, overoxidation and the formation of by-products and / or secondary products generally do not occur, especially when selective catalyst systems are used.

[0013] The selective catalytic conversion of unsaturated compounds to epoxides using N-oxides is well described in the literature (RSC Adv., 2016, 6, 88189-88215). Until now, the epoxidation of non-aromatic, linear α-olefins with N-oxides has only been achieved using complex ruthenium-based porphyrin catalysts and very long reaction times: For example, in the epoxidation of 1-octene using a ruthenium-porphyrin catalyst (molecular formula C 85 H 76 ON 4 Ru) and 2,6-dichloropyridine N-oxide in benzene as solvent at 125 °C in a Schlenk tube, a conversion of only 6% and an epoxide yield of 5% was achieved after 48 hours (J. Chem. Soc., Perkin Trans. 1, 1997).In another example, the epoxidation of 1-octene using an MCM-41-supported ruthenium porphyrin catalyst and 2,6-dichloropyridine N-oxide in dichloromethane as solvent at 40 °C resulted in a conversion of 80% and an epoxide yield of 74% after 24 hours (J. Org. Chem., 1998, 63, 7364-7369). In another example, the epoxidation of 1-octene using a PEGylated ruthenium porphyrin catalyst and 2,6-dichloropyridine N-oxide in dichloromethane as solvent at 50 °C resulted in a conversion of 82% and an epoxide yield of 81% after 24 hours (Chem.-Eur. J., 2006, 12, 3020-3031). A theoretical paper (RSC Adv., 2016, 6, 88189-88215) proposes the use of Ru(meso-tetrakis(2,6-dichlorophenyl)porphyrin) as a catalyst in combination with dimethylpyridine N-oxide for the epoxidation of propene to propylene oxide without specifying reaction conditions.

[0014] Overall, the low reaction temperatures combined with the long reaction times indicate that these Ru-based catalysts offer little added value for industrial use in the epoxidation of linear, terminal alkenes. Useful selectivities can only be achieved when very low reaction temperatures are chosen. Furthermore, the solvents used are not preferable for large-scale industrial use. The catalysts used in the state of the art contain Ru in the oxidation states (+II) and (+IV).

[0015] It was therefore an object of the present invention to provide a catalyst system for the direct production of alkylene oxides (epoxides), preferably propylene oxide, which, in the oxidative conversion of alkenes in the absence of oxygen or an oxygen-containing gas mixture, has, compared to systems known from the prior art, improved epoxide conversion and improved product selectivity by reducing the formation of undesirable by-products such as allylic compounds and their derivatives, and avoiding the formation of non-recyclable by-products. This improved catalyst activity and selectivity should be reflected in an activation energy EA of up to 24.0 kcal / mol, preferably from 10.0 kcal / mol to 21.0 kcal / mol, for the oxygen transfer to the alkene, preferably the propene, with side or subsequent reactions having higher activation energies than the preferred alkoxylation reaction.Higher activation energies of more than 24.0 kcal / mol would require higher reaction temperatures, which would favor the previously discussed, as well as other undesirable side reactions. Furthermore, the activation energies of side or subsequent reactions should be greater than or equal to 10.0 kcal / mol to allow selectivity control over reaction temperatures above 20 °C.

[0016] Surprisingly, it has been found that the object of the invention is achieved by a process for preparing an alkylene oxide by reacting an alkene with an arene oxide, pyridine N-oxide and / or pyrimidine N-oxide, preferably with an arene oxide and / or pyridine N-oxide in the presence of a catalyst (A) in a first reactor, wherein the catalyst (A) comprises a metal (A-1) and / or a metal salt (A-2), wherein the metal (A-1) is copper, silver and / or gold, wherein the metal salt (A-2) comprises chromium (Cr), iron (Fe), cobalt (Co) and / or copper (Cu) cation(s), and wherein the reaction takes place in the absence of oxygen or an oxygen-containing gas mixture.

[0017] The following embodiments can be combined as desired, unless the technical context and general technical knowledge indicate otherwise.

[0018] The alkylene oxide (epoxide) according to the invention can be an alkylene oxide having 2-45 carbon atoms. In one embodiment of the process according to the invention, the alkylene oxide is selected from at least one compound of the group consisting of ethylene oxide, propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, 2-methyl-1,2-propylene oxide (isobutene oxide), 1,2-pentylene oxide, 2,3-pentylene oxide, 2-methyl-1,2-butylene oxide, 3-methyl-1,2-butylene oxide, alkylene oxides of C6-C22 α-olefins, such as 1,2-hexylene oxide, 2,3-hexylene oxide, 3,4-hexylene oxide, 2-methyl-1,2-pentylene oxide, 4-methyl-1,2-pentylene oxide, 2-ethyl-1,2-butylene oxide, 1,2-heptylene oxide, 1,2-octylene oxide, 1,2-nonylene oxide, 1,2-decylene oxide, 1,2-undecylene oxide, 1,2-dodecylene oxide, 4-methyl-1,2-pentylene oxide, cyclopentylene oxide, cyclohexylene oxide, cycloheptylene oxide, cyclooctylene oxide, styrene oxide, methylstyrene oxide, pinene oxide, allyl glycedyl ether, vinylcyclohexylene oxide, cyclooctadiene monoepoxide, cyclododecatriene monoepoxide, butadiene monoepoxide, isoprene monoepoxide, limonene oxide,1,4-Divinylbenzene monoepoxide, 1,3-divinylbenzene monoepoxide, glycidyl acrylate, and glycidyl methacrylate; mono- or polyepoxidized fats as mono-, di-, and triglycerides; epoxidized fatty acids; C1-C24 esters of epoxidized fatty acids; epichlorohydrin; glycidol; and glycidol derivatives such as glycidyl ethers of C1-C22 alkanols and glycidyl esters of C1-C22 alkanecarboxylic acids. Examples of glycidol derivatives include phenyl glycidyl ether, cresyl glycidyl ether, methyl glycidyl ether, ethyl glycidyl ether, and 2-ethylhexyl glycidyl ether.

[0019] In a preferred embodiment of the process, the alkylene oxide is ethylene oxide, propylene oxide, 1,2-butylene oxide, 1,2-pentylene oxide, 1,2-hexylene oxide, 1,2-heptylene oxide, and / or 1,2-octylene oxide. In a particularly preferred embodiment of the process, the alkylene oxide is ethylene oxide and / or propylene oxide. In a very particularly preferred embodiment of the process, the alkylene oxide is propylene oxide.

[0020] In one embodiment of the process according to the invention, the alkene is one or more compound(s) and is selected from the group consisting of ethene, propene, butene, 1-octene, butadiene, 1,4-butanediol diallyl ether, allyl chloride, allyl alcohol, styrene, cyclopentene, cyclohexene, phenyl allyl ether, diallyl ether, n-butyl allyl ether, tert-butyl allyl ether, bisphenol A diallyl ether, resorcinol diallyl ether, triphenylolmethane triallyl ether, cyclohexane-1,2-dicarboxylic acid bis-(allyl ester), isocyanuric acid tris-(prop-2,3-ene) ester and mixtures of these alkenes, preferably ethene, propene and allyl chloride and particularly preferably propene.

[0021] In one embodiment of the process according to the invention, the arene oxide is one or more compounds according to formula (I), (II), (III) and / or (IV): with X 1 to X 8 independently of one another selected from the group F, Cl, Br, CN, -CO-CF 3 , -CO-C(CH3) 3 , -CO-CH 2 C(CH 3 ) 3 , -CO-C 6 H 5 , -CO-OC(CH 3 ) 3 , -CO-OCH 2 C(CH 3 ) 3 or H, preferably F, Cl, particularly preferably Cl.

[0022] In a preferred embodiment of the process according to the invention, the arene oxide is one or more compounds and is selected from the group consisting of hexafluorobenzene oxide, hexachlorobenzene oxide, 1-bromo-2,3,4-trifluorobenzene oxide, pentafluorobenzene oxide, 1,3,5-trichloro-2,4,6-trifluorobenzene oxide, 1,3,5-trifluorobenzene oxide, 1,2-dibromo-3,5-difluorobenzene oxide, 1,2,4,5-tetrafluorobenzene oxide, brompentafluorobenzene oxide, 1,3,5-trichlorobenzene oxide, 1-bromo-3,5-dichlorobenzene oxide, orthodichlorobenzene oxide, 1,2,4,5-tetrachlorobenzene oxide, 1,2,3-trichlorobenzene oxide and 1,5-dichloro-2-fluorobenzene oxide, preferably hexafluorobenzene oxide, and hexachlorobenzene oxide.

[0023] In one embodiment of the process according to the invention, the arene oxide is obtainable by reacting a first aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (C).

[0024] In one embodiment of the process according to the invention, the arene oxide is prepared by reacting a first aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (C).

[0025] The oxygen-containing gas mixture includes not only oxygen but also diluent, carrier or inert gases such as hydrocarbons, noble gases, CO, CO2 and / or N2.

[0026] In one embodiment of the process according to the invention, further additives such as water, CO, N-containing compounds such as, for example, hydrazine, ammonia (NH3), methylamine (MeNH2), NOx, PH3, SO2 and / or SO3 are added to the oxygen or an oxygen-containing gas mixture in amounts of 10 ppm to 500 ppm, preferably 30 ppm to 300 ppm and particularly preferably 50 ppm to 200 ppm. In addition, CO2 can be added in a proportion of 0.01 vol% to 50 vol%, preferably 0.1 vol% to 20 vol% and particularly preferably 1 vol% to 10 vol%. In addition, organic halides such as ethylene dichloride, ethyl chloride, vinyl chloride, methyl chloride and / or methylene chloride can be added in amounts of 10 ppm to 500 ppm, preferably 50 ppm to 400 ppm, and particularly preferably 100 ppm to 300 ppm.

[0027] In one embodiment of the process according to the invention, the first aromatic compound has a boiling temperature of 50 °C to 350 °C at 1 bara.

[0028] In one embodiment of the process according to the invention, the first aromatic compound is one or more compound(s) and is selected from the group consisting of hexafluorobenzene, hexachlorobenzene, 1-bromo-2,3,4-trifluorobenzene, pentafluorobenzene, 1,3,5-trichloro-2,4,6-trifluorobenzene, 1,3,5-trifluorobenzene, 1,2-dibromo-3,5-difluorobenzene, 1,2,4,5-tetrafluorobenzene, brompentafluorobenzene, 1,3,5-trichlorobenzene, 1-bromo-3,5-dichlorobenzene, orthodichlorobenzene, 1,2,4,5-tetrachlorobenzene, 1,2,3-trichlorobenzene and 1,5-dichro-2-fluorobenzene, preferably hexafluorobenzene and hexachlorobenzene.

[0029] In one embodiment of the process according to the invention, the catalyst (C) is one or more compound(s) and is selected from the group consisting of silver, silver supported on magnesium silicate and enzyme cytochrome P450.

[0030] In one embodiment of the process according to the invention, the molar ratio of oxygen to the first aromatic compound is from 1:500 to 1:1, preferably from 1:100 to 1:1.

[0031] In one embodiment of the process according to the invention, the catalyst (C) is used in a calculated amount of from 10 ppm to 15%, preferably from 100 ppm to 5% and particularly preferably from 100 ppm to 2%, based on the amount of the first aromatic compound.

[0032] In one embodiment of the process according to the invention, the arene oxide is prepared at a temperature of 20 °C to 250 °C, preferably from 50 °C to 220 °C and particularly preferably from 100 °C to 200 °C.

[0033] In one embodiment of the process according to the invention, the arene oxide is prepared at a pressure of 1 bara to 200 bara, preferably from 1 bara to 100 bara and particularly preferably from 1 bara to 60 bara.

[0034] In one embodiment of the process according to the invention, the arene oxide is prepared in a period of 6 min to 48 h, preferably from 6 min to 24 h and particularly preferably from 6 min to 3 h.

[0035] In one embodiment of the process according to the invention, the pyridine N-oxide is one or more compounds according to formula (V): with X 1 to X 5 independently of one another selected from the group F, Cl, Br, CN, -CO-CF 3 , -CO-C(CH3) 3 , -CO-CH 2 C(CH 3 ) 3 , -CO-C 6 H 5 , -CO-OC(CH 3 ) 3 , -CO-OCH 2 C(CH 3 ) 3 or H, preferably F, Cl, particularly preferably Cl.

[0036] In one embodiment of the process according to the invention, the pyridine N-oxide is one or more compound(s) and is selected from the group consisting of pentafluoropyridine N-oxide, 2-bromo-3,5-dichloropyridine N-oxide, 3-chloropyridine N-oxide, 3,6-dichloropyridine N-oxide, 3,5-dichloropyridine N-oxide, 3-chloro-2,5,6-trifluoropyridine N-oxide, 3-chloro-2,4,5,6-tetrafluoropyridine-1-N-oxide, 3-chloro-2,4,5,6-tetrafluoropyridine-3-N-oxide, preferably pentafluoropyridine N-oxide.

[0037] In one embodiment of the process according to the invention, the pyridine N-oxide is obtainable by reacting a second aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (D).

[0038] In one embodiment of the process according to the invention, the pyridine N-oxide is prepared by reacting a second aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (D).

[0039] In one embodiment of the process according to the invention, the second aromatic compound has a boiling temperature of 50 °C to 350 °C at 1 bara.

[0040] In one embodiment of the process according to the invention, the second aromatic compound is one or more compound(s) and is selected from the group consisting of pentafluoropyridine N-oxide, 2-bromo-3,5-dichloropyridine, 3-chloropyridine, 3,6-dichloropyridine, 3,5-dichloropyridine, 3-chloro-2,5,6-trifluoropyridine, 3-chloro-2,4,5,6-tetrafluoropyridine, 3-chloro-2,4,5,6-tetrafluoropyridine, preferably pentafluoropyridine.

[0041] In one embodiment of the process according to the invention, the catalyst (D) is one or more compound(s) and is selected from the group consisting of ruthenium trichloride, titanium-containing zeolites and silver.

[0042] In one embodiment of the process according to the invention, the catalyst (D) is applied to a catalyst support, and the catalyst support is one or more compounds and is selected from the group consisting of magnesium silicate, carbon, silica gel, alumina, titanium dioxide and cation exchange resin.

[0043] In one embodiment of the process according to the invention, the molar ratio of oxygen to the second aromatic compound is from 1:500 to 1:1, preferably from 1:100 to 1:1.

[0044] In one embodiment of the process according to the invention, the catalyst (D) is used in a calculated amount of 10 ppm to 15%, preferably 100 ppm to 5%, and particularly preferably 100 ppm to 2%, based on the amount of the second aromatic compound. In one embodiment of the process according to the invention, the pyridine N-oxide is prepared at a temperature of 0°C to 250°C, preferably 10°C to 220°C, and particularly preferably 20°C to 150°C.

[0045] In one embodiment of the process according to the invention, the pyridine N-oxide is prepared at a pressure of 1 bara to 200 bara, preferably from 1 bara to 100 bara and particularly preferably from 1 bara to 60 bara.

[0046] In one embodiment of the process according to the invention, the pyridine N-oxide is prepared in a period of 6 min to 48 h, preferably from 6 min to 24 h and particularly preferably from 6 min to 3 h.

[0047] In one embodiment of the process according to the invention, the pyrimidine N-oxide is one or more compounds according to formula (VI) and / or (VII): with X 1 to X 4 independently of one another selected from the group F, Cl, Br, CN, -CO-CF 3 , -CO-C(CH3) 3 , -CO-CH 2 C(CH 3 ) 3 , -CO-C 6 H 5 , -CO-OC(CH 3 ) 3 , -CO-OCH 2 C(CH 3 ) 3 or H, preferably F, Cl, particularly preferably Cl.

[0048] In one embodiment of the process according to the invention, the pyrimidine N-oxide is one or more compounds and is selected from the group consisting of 2-chloropyrimidine N-oxide, 2,4-dichloro-6-methylpyrimidine 1-N-oxide, 2,4-dichloro-6-methylpyrimidine 3-N-oxide, 2,5-dichloropyrimidine 1-N-oxide, 2,5-dichloropyrimidine 2-N-oxide.

[0049] In one embodiment of the process according to the invention, the pyrimidine N-oxide is obtainable by reacting a third aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (E).

[0050] In one embodiment of the process according to the invention, the pyrimidine N-oxide is prepared by reacting a third aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (E).

[0051] In one embodiment of the process according to the invention, the third aromatic compound has a boiling temperature of 50 °C to 350 °C at 1 bara.

[0052] In one embodiment of the process according to the invention, the third aromatic compound is one or more compound(s) and is selected from the group consisting of 2-chloropyrimidine, 2,4-dichloro-6-methylpyrimidine, 2,4-dichloro-6-methylpyrimidine, 2,5-dichloropyrimidine, preferably 2,4-dichloro-6-methylpyrimidine.

[0053] In one embodiment of the process according to the invention, the catalyst (E) is one or more compound(s) and is selected from the group consisting of ruthenium trichloride, titanium-containing zeolites and silver.

[0054] In one embodiment of the process according to the invention, the molar ratio of oxygen to the third aromatic compound is from 1:500 to 1:1, preferably from 1:100 to 1:1.

[0055] In one embodiment of the process according to the invention, the catalyst (E) is used in a calculated amount of from 10 ppm to 15%, preferably from 100 ppm to 5% and particularly preferably from 100 ppm to 2%, based on the amount of the third aromatic compound.

[0056] In one embodiment of the process according to the invention, the pyrimidine N-oxide is prepared at a temperature of from 0 °C to 250 °C, preferably from 10 °C to 220 °C and particularly preferably from 20 °C to 150 °C.

[0057] In one embodiment of the process according to the invention, the pyrimidine N-oxide is prepared at a pressure of 1 bara to 200 bara, preferably from 1 bara to 100 bara and particularly preferably from 1 bara to 60 bara.

[0058] In one embodiment of the process according to the invention, the preparation of the pyrimidine N-oxide takes place in a period of 6 min to 48 h, preferably from 6 min to 24 h and particularly preferably from 6 min to 3 h.

[0059] In one embodiment of the process according to the invention, the alkylene oxide is prepared in the presence of a catalyst (A), wherein the catalyst (A) comprises a metal (A-1) and / or a metal salt (A-2).

[0060] In one embodiment of the process according to the invention, the metal (A-1) is copper (Cu), silver (Ag) and / or gold (Au), preferably silver (Ag).

[0061] In one embodiment of the process according to the invention, the metal cation of the metal salt (A-2) has an oxidation state of (+I), (+II); (+III) or (+IV), preferably of (+II); (+III) or (+IV).

[0062] In one embodiment of the process according to the invention, the metal salt (A-2) is a nitrate, halide, tetrafluoroborate, sulfate, paratoluenesulfonate, methanesulfonate and / or triflate, preferably a chloride.

[0063] In one embodiment of the process according to the invention, the metal salt (A-2) is one or more compound(s) and is selected from the group consisting of Cr 2 (SO 4 ) 3 , KCr(SO 4 ) 2 , Cr(NO 3 ) 3 , CrF 3 , CrCl 3 , FeCl 3 , FeBr 3 , iron triflate, FePO 4 , Fe 2 (SO 4) 3 , Fe(NO 3 ) 3 , FeF 3 , iron paratoluenesulfonate, CoCl 2 , CoBr 2 , Co(NO 3 ) 2 , CoBr 2 , CoSO 4 , CoF 2 , Co(BF 4 ) 2 , Co 3 (PO 4 ) 2 , CuCl 2 , CuSO 4 , (CF 3 SO 3 ) 2 Cu, CuF 2 , Cu(NO 3 ) 2 , copper(II) pyrophosphate CuCl, CuI and CuBr, preferably CrCl 3 , FeCl 3 , CoCl 2 and CuCl 2 . The metal salts can also be present as hydrates.

[0064] In one embodiment of the process according to the invention, catalyst (A) is used in a calculated amount of from 10 ppm to 15%, preferably from 100 ppm to 5% and particularly preferably from 100 ppm to 2%, based on the mass of all components used.

[0065] In one embodiment of the process according to the invention, the catalyst (A) is applied to a catalyst support (B) to form a supported catalyst (A').

[0066] In one embodiment of the process according to the invention, the catalyst support (B) is a metal oxide, an alkaline earth metal carbonate, a silicate, a silicon carbide, a silicon oxycarbide, a silicon nitride, a silicon oxynitride and / or a silicon dioxide.

[0067] In a preferred embodiment of the process according to the invention, the catalyst support (B) is one or more compound(s) and is selected from the group consisting of alumina, alumina, silica, titania, zirconium dioxide, calcium carbonate, phyllosilicate, such as talc, kaolinite and pyrophyllite, and titania.

[0068] In one embodiment of the process according to the invention, the catalyst (A) is applied to the catalyst support (B) in a calculated mass fraction of 1.0 wt.% to 30.0 wt.%.

[0069] In one embodiment of the process according to the invention, the catalyst (A) is applied to the catalyst support (B) using the wet infiltration method or the incipient wetness method.

[0070] In one embodiment of the process according to the invention, the molar ratio of the alkene to the arene oxide is from 1:0.01 to 10:1, preferably from 1:0.1 to 1:1.

[0071] In one embodiment of the process according to the invention, the alkylene oxide is prepared in the presence of a solvent.

[0072] In one embodiment of the process according to the invention, the solvent is one or more compound(s) and is selected from the group consisting of CO2, water, perfluoromethyldecalin, perfluorodecalin, perfluoroperhydrophenanthrene, perfluoro(butyltetrahydrofuran), tetrahydrofuran, 2-methyl-THF, acetic acid, acetonitrile, dimethyl sulfoxide, sulfolane, acetone, ethyl methyl ketone, dimethylformamide, dichloromethane, chloroform, carbon tetrachloride, N-methyl-2-pyrrolidinone, methyl t-butyl ether (MTBE), dimethyl sulfide (DMSO), hexamethylphosphoramide, dichlorobenzene, 1,2-dichloroethylene, 1,1,1,3,3,3-hexafluoroisopropanol, perfluoro-tert-butyl alcohol, 1,1,2,3,3-pentafluoropropane, 1-Bromo-2-chloro-1,1,2-trifluoroethane, 1,2-dichloro-1,1,2,3,3,3-hexafluoropropane, ethylene glycol, glycerin, and phenol.

[0073] In one embodiment of the process according to the invention, the preparation takes place at a temperature of 20 °C to 200 °C, preferably from 50 °C to 160 °C and particularly preferably from 100 °C to 150 °C.

[0074] In one embodiment of the process according to the invention, the production takes place at a pressure of 1 bara to 200 bara, preferably from 1 bara to 35 bara and particularly preferably from 1 bara to 28 bara.

[0075] In one embodiment of the process according to the invention, the preparation takes place in a period of 6 min to 48 h, preferably from 6 min to 24 h and particularly preferably from 6 min to 3 h.

[0076] In one embodiment of the process according to the invention, the molar ratio of the alkene to oxygen is from 1:100 to 100:1, preferably from 1:30 to 30:1.

[0077] In one embodiment of the process according to the invention, the preparation takes place in the absence of a solvent.

[0078] According to the invention, a production process in the absence of a solvent means that solvent residues may be present, for example as a result of the production of the starting materials, of up to 10 vol.%, preferably of up to 5 vol.% and particularly preferably of up to 2 vol.%, based on the amount of propene used.

[0079] In one embodiment of the process according to the invention, the preparation is carried out using the supported catalyst (A') according to the invention.

[0080] In one embodiment of the process according to the invention, the preparation takes place at a temperature of 20 °C to 500 °C, preferably from 50 °C to 400 °C and particularly preferably from 50 °C to 250 °C.

[0081] In one embodiment of the process according to the invention, the production takes place at a pressure of 1 bara to 200 bara, preferably from 2 bara to 100 bara and particularly preferably from 2 bara to 50 bara.

[0082] In one embodiment of the process according to the invention, the preparation is carried out at a space velocity of 100 h-1 to 10,000 h-1, preferably of 200 h-1 to 5,000 h-1 and particularly preferably of 500 h-1 to 2,000 h-1.

[0083] In one embodiment of the process according to the invention, the molar ratio of the alkene to the oxygen is from 1.0:0.1 to 2.0:1.0, preferably from 1.0:0.5 to 2.0:1.0 and particularly preferably from 1.0:0.8 to 2.0:1.0.

[0084] In one embodiment of the process according to the invention, a first aromatic compound is formed by reacting the alkene with the arene oxide, a second aromatic compound is formed by reacting the alkene with the pyridine N-oxide and / or a third aromatic compound is formed by reacting the alkene with the pyrimidine N-oxide.

[0085] In one embodiment of the process according to the invention, the alkene is metered continuously or stepwise, preferably continuously, into the first reactor.

[0086] In one embodiment of the process according to the invention, the arene oxide, pyridine N-oxide and / or the pyrimidine N-oxide is metered continuously or stepwise, preferably continuously, into the first reactor.

[0087] In one embodiment of the process according to the invention, the alkene and the arene oxide, pyridine N-oxide and / or the pyrimidine N-oxide are metered continuously or stepwise, preferably continuously, into the first reactor.

[0088] In one embodiment of the process according to the invention, the alkylene oxide is removed continuously or stepwise, preferably continuously, from the first reactor.

[0089] In one embodiment of the process according to the invention, the first aromatic compound, the second aromatic compound and / or the third aromatic compound are removed continuously or stepwise, preferably continuously, from the first reactor.

[0090] In one embodiment of the process according to the invention, the alkylene oxide and the halogenated, preferably the alkylene oxide and the first aromatic compound, the second aromatic compound and / or the third aromatic compound are removed continuously or stepwise, preferably continuously, from the first reactor.

[0091] In one embodiment of the process according to the invention, the catalyst (A) is metered continuously or stepwise, preferably continuously, into the reactor.

[0092] In one embodiment of the process according to the invention, the first reactor is a stirred tank, flow tube, bubble column, loop reactor, trickle bed reactor, spray tower reactor or falling film reactor.

[0093] In one embodiment of the process according to the invention, the arene oxide, the pyridine oxide and / or the pyrimidine N-oxide is prepared in a second reactor, wherein the second reactor is different from the first reactor.

[0094] In one embodiment of the process according to the invention, the arene oxide, the pyridine N-oxide and / or the pyrimidine N-oxide are prepared in the second reactor at a temperature of 20 °C to 250 °C, preferably from 50 °C to 220 °C and particularly preferably from 100 °C to 200 °C.

[0095] In one embodiment of the process according to the invention, the arene oxide, the pyridine N-oxide and / or the pyrimidine N-oxide are prepared in the second reactor at a pressure of 1 bara to 200 bara, preferably from 1 bara to 100 bara and particularly preferably from 1 bara to 60 bara.

[0096] In one embodiment of the process according to the invention, the arene oxide, the pyridine N-oxide and / or the pyrimidine N-oxide are prepared in the second reactor in a period of 6 min to 48 h, preferably from 6 min to 24 h and particularly preferably from 6 min to 3 h.

[0097] In one embodiment of the process according to the invention, the first aromatic compound, the second aromatic compound and / or the third aromatic compound are metered continuously or stepwise, preferably continuously, into the second reactor.

[0098] In one embodiment of the process according to the invention, oxygen or the oxygen-containing gas mixture is metered continuously or stepwise, preferably continuously, into the second reactor.

[0099] In one embodiment of the process according to the invention, the first aromatic compound, the second aromatic compound and / or the third aromatic compound and oxygen or the oxygen-containing gas mixture are metered continuously or stepwise, preferably continuously, into the second reactor.

[0100] In one embodiment of the process according to the invention, the arene oxide, the pyridine N-oxide and / or the pyrimidine N-oxide is removed continuously or stepwise, preferably continuously, from the second reactor.

[0101] In one embodiment of the process according to the invention, the catalyst (C) is metered continuously or stepwise, preferably continuously, into the second reactor.

[0102] In one embodiment of the process according to the invention, the second reactor is a stirred tank, flow tube, bubble column, loop reactor, trickle bed reactor, spray tower reactor or falling film reactor.

[0103] In one embodiment of the process according to the invention, the arene oxide, pyridine N-oxide and / or pyrimidine N-oxide produced in the second reactor is metered continuously or stepwise, preferably continuously, into the first reactor.

[0104] The invention further relates to the use of the catalyst (A) for preparing the alkylene oxide according to the invention by reacting the alkene according to the invention with the arene oxide according to the invention, the pyridine N-oxide according to the invention and / or the pyrimidine N-oxide according to the invention, preferably with the arene oxide according to the invention and / or the pyridine N-oxide according to the invention.

[0105] In a first embodiment, the invention relates to a process for preparing an alkylene oxide by reacting an alkene with an arene oxide, pyridine N-oxide and / or pyrimidine N-oxide, preferably with an arene oxide and / or pyridine N-oxide in the presence of a catalyst (A) in a first reactor, wherein the catalyst (A) comprises a metal (A-1) and / or a metal salt (A-2), wherein the metal (A-1) is copper, silver and / or gold, wherein the metal salt (A-2) comprises chromium (Cr), iron (Fe), cobalt (Co), and / or copper (Cu) cation(s), and wherein the reaction takes place in the absence of oxygen or an oxygen-containing gas mixture.

[0106] In a second embodiment, the invention relates to a process according to the first embodiment, wherein the alkylene oxide is one or more compound(s) and is selected from the group consisting of ethylene oxide, propylene oxide, 1,2-butylene oxide, 1,2-pentylene oxide, 1,2-hexylene oxide, 1,2-heptylene oxide and 1,2-octylene oxide, preferably ethylene oxide and propylene oxide, particularly preferably propylene oxide.

[0107] In a third embodiment, the invention relates to a process according to the first or second embodiment, wherein the arene oxide is one or more compounds according to formula (I), (II), (III) and / or (IV): with X 1 to X 8 independently selected from the group of F, Cl, Br, CN, -CO-RCF 3 , -CO-C(CH 3 ) 3 , -CO-CH 2 C(CH 3 ) 3 , -CO-C 6 H 5 , -CO-OC(CH 3 ) 3 , -CO-OCH 2 C(CH 3 ) 3 or H, preferably F, Cl, particularly preferably Cl.

[0108] In a fourth embodiment, the invention relates to a process according to one of the first or fourth embodiments, wherein the arene oxide is one or more compound(s) and is selected from the group consisting of hexafluorobenzene oxide, hexachlorobenzene oxide, 1-bromo-2,3,4-trifluorobenzene oxide, pentafluorobenzene oxide, 1,3,5-trichloro-2,4,6-trifluorobenzene oxide, 1,3,5-trifluorobenzene oxide, 1,2-dibromo-3,5-difluorobenzene oxide, 1,2,4,5-tetrafluorobenzene oxide, brompentafluorobenzene oxide, 1,3,5-trichlorobenzene oxide, 1-bromo-3,5-dichlorobenzene oxide, orthodichlorobenzene oxide, 1,2,4,5-tetrachlorobenzene oxide, 1,2,3-trichlorobenzene oxide and 1,5-dichloro-2-fluorobenzene oxide, preferably Hexafluorobenzene oxide, and hexachlorobenzene oxide.

[0109] In a fifth embodiment, the invention relates to a process according to any one of the first to fourth embodiments, wherein the arene oxide is obtainable by reacting a first aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (C).

[0110] In a sixth embodiment, the invention relates to a process according to any one of the first to fifth embodiments, wherein the arene oxide is prepared by reacting a first aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (C).

[0111] In a seventh embodiment, the invention relates to a process according to the fifth or sixth embodiment, wherein the first aromatic compound has a boiling temperature of 50 °C to 350 °C at 1 bara.

[0112] In an eighth embodiment, the invention relates to a process according to any one of the fifth to seventh embodiments, wherein the first aromatic compound is one or more compound(s) and is selected from the group consisting of hexafluorobenzene, hexachlorobenzene, 1-bromo-2,3,4-trifluorobenzene, pentafluorobenzene, 1,3,5-trichloro-2,4,6-trifluorobenzene, 1,3,5-trifluorobenzene, 1,2-dibromo-3,5-difluorobenzene, 1,2,4,5-tetrafluorobenzene, brompentafluorobenzene, 1,3,5-trichlorobenzene, 1-bromo-3,5-dichlorobenzene, orthodichlorobenzene, 1,2,4,5-tetrachlorobenzene, 1,2,3-trichlorobenzene and 1,5-dichro-2-fluorobenzene, preferably hexafluorobenzene and hexachlorobenzene.

[0113] In a ninth embodiment, the invention relates to a process according to any one of the fifth to eighth embodiments, wherein the catalyst (C) is one or more compounds and is selected from the group consisting of silver, silver supported on magnesium silicate and enzyme cytochrome P450.

[0114] In a tenth embodiment, the invention relates to a process according to one of the fifth to ninth embodiments, wherein the molar ratio of oxygen to the first aromatic compound is from 1:500 to 1:1, preferably from 1:100 to 1:1.

[0115] In an eleventh embodiment, the invention relates to a process according to any one of the fifth to tenth embodiments, wherein the catalyst (C) is used in a calculated amount of from 10 ppm to 15%, preferably from 100 ppm to 5% and particularly preferably from 100 ppm to 2%, based on the amount of the first aromatic compound.

[0116] In a twelfth embodiment, the invention relates to a process according to one of the fifth to eleventh embodiments, wherein the preparation of the arene oxide takes place at a temperature of 20 °C to 250 °C, preferably from 50 °C to 220 °C and particularly preferably from 100 °C to 200 °C.

[0117] In a thirteenth embodiment, the invention relates to a process according to any one of the fifth to twelfth embodiments, wherein the arene oxide is prepared at a pressure of 1 bara to 200 bara, preferably from 1 bara to 100 bara, and particularly preferably from 1 bara to 60 bara. In a fourteenth embodiment, the invention relates to a process according to any one of the fifth to thirteenth embodiments, wherein the arene oxide is prepared in a period of 6 min to 48 h, preferably from 6 min to 24 h, and particularly preferably from 6 min to 3 h.

[0118] In a fifteenth embodiment, the invention relates to a process according to any one of the first to fourteenth embodiments, wherein the pyridine N-oxide is one or more compounds according to formula (V): with E is selected from the group of NX 1 to X 5 independently of one another selected from the group of F, Cl, Br, CN, -CO-CF 3 , -CO-C(CH 3 ) 3 , -CO-CH 2 C(CH 3 ) 3 , -CO-C 6 H 5 , -CO-OC(CH 3 ) 3 , -CO-OCH 2 C(CH 3 ) 3 or H, preferably F, Cl, particularly preferably Cl.

[0119] In a sixteenth embodiment, the invention relates to a process according to any one of the first to fifteenth embodiments, wherein the pyridine N-oxide is one or more compound(s) and is selected from the group consisting of pentafluoropyridine N-oxide, 2-bromo-3,5-dichloropyridine N-oxide, 3-chloropyridine N-oxide, 3,6-dichloropyridine N-oxide, 3,5-dichloropyridine N-oxide, 3-chloro-2,5,6-trifluoropyridine N-oxide, 3-chloro-2,4,5,6-tetrafluoropyridine-1-N-oxide, 3-chloro-2,4,5,6-tetrafluoropyridine-3-N-oxide, preferably pentafluoropyridine N-oxide.

[0120] In a seventeenth embodiment, the invention relates to a process according to the fifteenth or sixteenth embodiment, wherein the pyridine N-oxide is obtainable by reacting a second aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (D).

[0121] In an eighteenth embodiment, the invention relates to a process according to the fifteenth or sixteenth embodiment, wherein the pyridine N-oxide is prepared by reacting a second aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (D).

[0122] In a nineteenth embodiment, the invention relates to a process according to the seventeenth or eighteenth embodiment, wherein the second aromatic compound has a boiling temperature of 50 °C to 350 °C at 1 bara.

[0123] In a twentieth embodiment, the invention relates to a process according to any one of the seventeenth to nineteenth embodiments, wherein the second aromatic compound is one or more compound(s) selected from the group consisting of pentafluoropyridine N-oxide, 2-bromo-3,5-dichloropyridine, 3-chloropyridine, 3,6-dichloropyridine, 3,5-dichloropyridine, 3-chloro-2,5,6-trifluoropyridine, 3-chloro-2,4,5,6-tetrafluoropyridine, 3-chloro-2,4,5,6-tetrafluoropyridine, preferably pentafluoropyridine.

[0124] In a twenty-first embodiment, the invention relates to a process according to any one of the seventeenth to twentieth embodiments, wherein the catalyst (D) is one or more compounds selected from the group consisting of ruthenium trichloride, silver and titanium-containing zeolites.

[0125] In a twenty-second embodiment, the invention relates to a process according to the twenty-first embodiment, wherein the catalyst (D) is applied to a catalyst support, and the catalyst support is one or more and is selected from the group consisting of magnesium silicate, silica gel, alumina, titanium dioxide and cation exchange resin.

[0126] In a twenty-third embodiment, the invention relates to a process according to any one of the seventeenth to twenty-second embodiments, wherein the molar ratio of oxygen to the second aromatic compound is from 1:500 to 1:1, preferably from 1:100 to 1:1.

[0127] In a twenty-fourth embodiment, the invention relates to a process according to any one of the seventeenth to twenty-third, wherein the catalyst (D) is used in a calculated amount of from 10 ppm to 15%, preferably from 100 ppm to 5% and particularly preferably from 100 ppm to 2%, based on the amount of the second aromatic compound.

[0128] In a twenty-fifth embodiment, the invention relates to a process according to any one of the seventeenth to twenty-third, wherein the preparation of the pyridine N-oxide is carried out at a temperature of from 0 °C to 250 °C, preferably from 10 °C to 220 °C and particularly preferably from 20 °C to 150 °C.

[0129] In a twenty-sixth embodiment, the invention relates to a process according to any one of the seventeenth to twenty-fifth, wherein the preparation of the pyridine N-oxide is carried out at a pressure of 1 bara to 200 bara, preferably from 1 bara to 100 bara and particularly preferably from 1 bara to 60 bara.

[0130] In a twenty-seventh embodiment, the invention relates to a process according to any one of the seventeenth to twenty-sixth, wherein the preparation of the pyridine N-oxide takes place within a period of 6 min to 48 h, preferably from 6 min to 24 h, and particularly preferably from 6 min to 3 h. In a twenty-eighth embodiment, the invention relates to a process according to any one of the first to twenty-seventh, wherein the pyrimidine N-oxide is one or more compounds of the formula (VI): with X 1 to X 4 independently selected from the group of F, Cl, Br, CN, -CO-CF 3 , -CO-C(CH 3 ) 3 , -CO-CH 2 C(CH 3 ) 3 , -CO-C 6 H 5 , -CO-OC(CH 3 ) 3 , -CO-OCH 2 C(CH 3 ) 3 or H, preferably F, Cl, particularly preferably Cl.

[0131] In a twenty-ninth embodiment, the invention relates to a process according to any one of the first to twenty-eighth embodiments, wherein the pyrimidine N-oxide is one or more compounds selected from the group consisting of 2-chloropyrimidine N-oxide, 2,4-dichloro-6-methylpyrimidine 1-N-oxide, 2,4-dichloro-6-methylpyrimidine 3-N-oxide, 2,5-dichloropyrimidine 1-N-oxide, 2,5-dichloropyrimidine 2-N-oxide.

[0132] In a thirtieth embodiment, the invention relates to a process according to any one of the first to twenty-ninth embodiments, wherein the pyrimidine N-oxide is obtainable by reacting a third aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (E).

[0133] In a thirty-first embodiment, the invention relates to a process according to any one of the first to thirtieth embodiments, wherein the pyrimidine N-oxide is prepared by reacting a third aromatic compound with oxygen or an oxygen-containing gas mixture in the presence of a catalyst (E).

[0134] In a thirty-second embodiment, the invention relates to a process according to the thirtieth or thirty-first embodiment, wherein the third aromatic compound has a boiling temperature of 50 °C to 350 °C at 1 bara.

[0135] In a thirty-third embodiment, the invention relates to a process according to any one of the thirtieth to thirty-second embodiments, wherein the third aromatic compound is one or more compound(s) selected from the group consisting of 2-chloropyrimidine, 2,4-dichloro-6-methylpyrimidine, 2,4-dichloro-6-methylpyrimidine, 2,5-dichloropyrimidine, preferably 2,4-dichloro-6-methylpyrimidine.

[0136] In a thirty-fourth embodiment, the invention relates to a catalyst according to any one of the thirtieth to thirty-third embodiments, wherein the catalyst (E) is one or more compounds selected from the group consisting of ruthenium trichloride, titanium-containing zeolites and silver.

[0137] In a thirty-fifth embodiment, the invention relates to a process according to any one of the thirtieth to thirty-fourth embodiments, wherein the molar ratio of oxygen to the third aromatic compound is from 1:500 to 1:1, preferably from 1:100 to 1:1.

[0138] In a thirty-sixth embodiment, the invention relates to a process according to any one of the thirtieth to thirty-fifth embodiments, wherein the catalyst (E) is used in a calculated amount of from 10 ppm to 15%, preferably from 100 ppm to 5% and particularly preferably from 100 ppm to 2%, based on the amount of the third aromatic compound.

[0139] In a thirty-seventh embodiment, the invention relates to a process according to any one of the thirtieth to thirty-sixth embodiments, wherein the preparation of the pyrimidine N-oxide is carried out at a temperature of from 0 °C to 250 °C, preferably from 10 °C to 220 °C and particularly preferably from 20 °C to 150 °C.

[0140] In a thirty-eighth embodiment, the invention relates to a process according to any one of the thirtieth to thirty-seventh embodiments, wherein the preparation of the pyrimidine N-oxide is carried out at a pressure of 1 bara to 200 bara, preferably from 1 bara to 100 bara and particularly preferably from 1 bara to 60 bara.

[0141] In a thirty-ninth embodiment, the invention relates to a process according to any one of the thirtieth to thirty-eighth embodiments, wherein the preparation of the pyrimidine N-oxide takes place in a period of 6 min to 48 h, preferably from 6 min to 24 h and particularly preferably from 6 min to 3 h.

[0142] In a fortieth embodiment, the invention relates to a method according to any one of the first to thirty-ninth embodiments, wherein the metal (A-1) is copper (Cu), silver (Ag) and / or gold (Au), preferably silver (Ag).

[0143] In a forty-first embodiment, the invention relates to a process according to any one of the first to fortieth embodiments, wherein the metal cation of the metal salt (A-2) has an oxidation state of (+I); (+II); (+III) or (+IV), preferably of (+II); (+III) or (+IV). In a forty-second embodiment, the invention relates to a process according to any one of the first to forty-first embodiments, wherein the metal salt (A-2) is a nitrate, halide, tetrafluoroborate, sulfate, paratoluenesulfonate, methanesulfonate and / or triflate, preferably a chloride.

[0144] In a forty-third embodiment, the invention relates to a process according to any one of the first to forty-second embodiments, wherein the metal salt (A-2) is one or more compounds and is selected from the group consisting of Cr 2 (SO 4 ) 3 , KCr(SO 4 ) 2 , Cr(NO 3 ) 3 , CrF 3 , CrCl 3 , FeCl 3 , FeBr 3 , iron triflate, FePO 4 , Fe 2 (SO 4) 3 , Fe(NO 3 ) 3 , FeF 3 , iron paratoluenesulfonate, CoCl 2 , CoBr 2 , Co(NO 3 ) 2 , CoBr 2 , CoSO 4 , CoF 2 , Co(BF 4 ) 2 , Co 3 (PO 4 ) 2 , CuCl 2 , CuSO 4 , (CF 3 SO 3 ) 2 Cu, CuF 2 , Cu(NO 3 ) 2 , copper(II) pyrophosphate, and CuCl, CuI, CuBr preferably CrCl 3 , FeCl 3 , CoCl 2 and CuCl 2 .

[0145] In a forty-fourth embodiment, the invention relates to a process according to any one of the first to forty-third embodiments, wherein catalyst (A) is used in a calculated amount of from 10 ppm to 15%, preferably from 100 ppm to 5% and particularly preferably from 100 ppm to 2%, based on the mass of all components used.

[0146] In a forty-fifth embodiment, the invention relates to a process according to any one of the first to forty-fourth embodiments, wherein the catalyst (A) is applied to a catalyst support (B) to form a supported catalyst (A').

[0147] In a forty-sixth embodiment, the invention relates to a process according to the forty-fifth embodiment, wherein the catalyst support (B) is a metal oxide, an alkaline earth metal carbonate, a silicate, a silicon carbide, a silicon oxycarbide, a silicon nitride, a silicon oxynitride and / or a silicon dioxide.

[0148] In a forty-seventh embodiment, the invention relates to a process according to the forty-fifth or forty-sixth embodiment, wherein the catalyst support (B) is one or more compound(s) and is selected from the group consisting of alumina, alumina, silica, titania, zirconia, calcium carbonate, phyllosilicate such as talc, kaolinite and pyrophyllite, and titania.

[0149] In a forty-eighth embodiment, the invention relates to a process according to any one of the forty-fifth to forty-seventh embodiments, wherein the catalyst (A) is applied to the catalyst support (B) in a calculated mass fraction of 1.0 wt.% to 30.0 wt.%.

[0150] In a forty-ninth embodiment, the invention relates to a process according to any one of the forty-fifth to forty-eighth embodiments, wherein the catalyst (A) is applied to the catalyst support (B) by means of the wet infiltration method or the incipient wetness method to form the supported catalyst (A').

[0151] In a fiftieth embodiment, the invention relates to a process according to any one of the first to forty-ninth embodiments, wherein the molar ratio of the alkene to the arene oxide is from 1:0.01 to 10:1, preferably from 1:0.1 to 1:1.

[0152] In a fifty-first embodiment, the invention relates to a process according to any one of the first to fiftieth embodiments, wherein the preparation of the alkylene oxide takes place in the presence of a solvent.

[0153] In a fifty-second embodiment, the invention relates to a process according to the fifty-first embodiment, wherein the solvent is one or more compound(s) selected from the group consisting of CO2, water, perfluoromethyldecalin, perfluorodecalin, perfluoroperhydrophenanthrene, perfluoro(butyltetrahydrofuran), tetrahydrofuran, 2-methyl-THF, acetic acid, acetonitrile, dimethyl sulfoxide, sulfolane, acetone, ethyl methyl ketone, dimethylformamide, dichloromethane, chloroform, carbon tetrachloride, N-methyl-2-pyrrolidinone, methyl t-butyl ether (MTBE), dimethyl sulfide (DMSO), hexamethylphosphoramide, dichlorobenzene, 1,2-dichloroethylene, 1,1,1,3,3,3-hexafluoroisopropanol, perfluoro-tert-butyl alcohol, 1,1,2,3,3-pentafluoropropane, 1-bromo-2-chloro-1,1,2-trifluoroethane, 1,2-dichloro-1,1,2,3,3,3-hexafluoropropane, ethylene glycol, glycerin, and phenol.

[0154] In a fifty-third embodiment, the invention relates to a process according to the fifty-first or fifty-second embodiment, wherein the preparation takes place at a temperature of 20 °C to 200 °C, preferably from 50 °C to 160 °C and particularly preferably from 100 °C to 150 °C.

[0155] In a fifty-fourth embodiment, the invention relates to a process according to one of the fifty-first to fifty-third embodiments, wherein the production is carried out at a pressure of 1 bara to 200 bara, preferably from 1 bara to 35 bara and particularly preferably from 1 bara to 28 bara.

[0156] In a fifty-fifth embodiment, the invention relates to a process according to one of the fifty-first to fifty-fourth embodiments, wherein the preparation takes place in a period of 6 min to 48 h, preferably from 6 min to 24 h and particularly preferably from 6 min to 3 h.

[0157] In a fifty-sixth embodiment, the invention relates to a process according to any one of the fifty-first to fifty-fifth embodiments, wherein the molar ratio of the alkene to oxygen is from 1:100 to 100:1, preferably from 1:30 to 30:1.

[0158] In a fifty-seventh embodiment, the invention relates to a process according to any one of the first to fifty-sixth embodiments, wherein the preparation is carried out in the absence of a solvent.

[0159] In a fifty-eighth embodiment, the invention relates to a process according to the fifty-seventh embodiment, wherein the preparation is carried out using supported catalyst (A') according to any one of the forty-fifth to forty-ninth embodiments.

[0160] In a fifty-ninth embodiment, the invention relates to a process according to the fifty-seventh or fifty-eighth embodiment, wherein the preparation is carried out at a temperature of 20 °C to 500 °C, preferably from 50 °C to 400 °C and particularly preferably from 50 °C to 250 °C.

[0161] In a sixtieth embodiment, the invention relates to a process according to one of the fifty-seventh to fifty-ninth embodiments, wherein the production takes place at a pressure of 1 bara to 200 bara, preferably from 2 bara to 100 bara and particularly preferably from 2 bara to 50 bara.

[0162] In a sixty-first embodiment, the invention relates to a process according to one of the fifty-seventh to sixtieth embodiments, wherein the preparation is carried out at a space velocity of 100 h -1< to 10,000 h -1<, preferably of 200 h -1< to 5,000 h -1< and particularly preferably of 500 h -1< to 2,000 h -1<.

[0163] In a sixty-second embodiment, the invention relates to a process according to any one of the fifty-seventh to sixty-first embodiments, wherein the molar ratio of the alkene to the oxygen is from 1.0:0.1 to 2.0:1.0, preferably from 1.0:0.5 to 2.0:1.0 and particularly preferably from 1.0:0.8 to 2.0:1.0.

[0164] In a sixty-third embodiment, the invention relates to a process according to any one of the first to sixty-second embodiments, wherein a first aromatic compound is formed by reacting the alkene with the arene oxide, a second aromatic compound is formed by reacting the alkene with the pyridine N-oxide and / or a third aromatic compound is formed by reacting the alkene with the pyrimidine N-oxide.

[0165] In a sixty-fourth embodiment, the invention relates to a process according to any one of the first to sixty-third embodiments, wherein the alkene is metered continuously or stepwise, preferably continuously, into the first reactor.

[0166] In a sixty-fifth embodiment, the invention relates to a process according to any one of the first to sixty-fourth embodiments, wherein the arene oxide, pyridine N-oxide and / or the pyrimidine N-oxide is metered continuously or stepwise, preferably continuously, into the first reactor.

[0167] In a sixty-sixth embodiment, the invention relates to a process according to any one of the first to sixty-fifth embodiments, wherein the alkene and the arene oxide, pyridine N-oxide and / or the pyrimidine N-oxide are metered continuously or stepwise, preferably continuously, into the first reactor.

[0168] In a sixty-seventh embodiment, the invention relates to a process according to any one of the first to sixty-sixth embodiments, wherein the alkylene oxide is withdrawn continuously or stepwise, preferably continuously, from the first reactor.

[0169] In a sixty-eighth embodiment, the invention relates to a process according to any one of the sixty-third to sixty-seventh embodiments, wherein the first aromatic compound, the second aromatic compound, and / or the third aromatic compound are withdrawn continuously or stepwise, preferably continuously, from the first reactor. In a sixty-ninth embodiment, the invention relates to a process according to any one of the sixty-third to sixty-eighth embodiments, wherein the alkylene oxide and the halogenated compound, preferably the alkylene oxide and the first aromatic compound, the second aromatic compound, and / or the third aromatic compound are withdrawn continuously or stepwise, preferably continuously, from the first reactor.

[0170] In a seventy-fifth embodiment, the invention relates to a process according to any one of the first to sixty-ninth embodiments, wherein the catalyst (A) is metered continuously or stepwise, preferably continuously, into the reactor.

[0171] In a seventy-first embodiment, the invention relates to a process according to any one of the first to seventy-first embodiments, wherein the first reactor is a stirred tank, flow tube, bubble column, loop reactor, trickle bed reactor, spray tower reactor, or falling film reactor. In a seventy-second embodiment, the invention relates to a process according to any one of the first to seventy-first embodiments, wherein the arene oxide, the pyridine oxide, and / or the pyrimidine N-oxide is prepared in a second reactor, wherein the second reactor is different from the first reactor.

[0172] In a seventy-third embodiment, the invention relates to a process according to the seventy-second embodiment, wherein the preparation of the arene oxide, the pyridine N-oxide and / or the pyrimidine N-oxide in the second reactor takes place at a temperature of 20 °C to 250 °C, preferably from 50 °C to 220 °C and particularly preferably from 100 °C to 200 °C.

[0173] In a seventy-fourth embodiment, the invention relates to a process according to the seventy-second or seventy-third embodiment, wherein the preparation of the arene oxide, the pyridine N-oxide and / or the pyrimidine N-oxide in the second reactor is carried out at a pressure of 1 bara to 200 bara, preferably from 1 bara to 100 bara and particularly preferably from 1 bara to 60 bara.

[0174] In a seventy-fifth embodiment, the invention relates to a process according to one of the seventy-second to seventy-fourth embodiments, wherein the preparation of the arene oxide, the pyridine N-oxide and / or the pyrimidine N-oxide in the second reactor takes place in a period of 6 min to 48 h, preferably from 6 min to 24 h and particularly preferably from 6 min to 3 h.

[0175] In a seventy-sixth embodiment, the invention relates to a process according to one of the seventy-second to seventy-fifth embodiments, wherein the first aromatic compound, the second aromatic compound and / or the third aromatic compound is metered continuously or stepwise, preferably continuously, into the second reactor.

[0176] In a seventy-seventh embodiment, the invention relates to a process according to one of the seventy-second to seventy-sixth embodiments, wherein oxygen or the oxygen-containing gas mixture is metered continuously or stepwise, preferably continuously, into the second reactor.

[0177] In a seventy-eighth embodiment, the invention relates to a process according to one of the seventy-second to seventy-seventh embodiments, wherein the first aromatic compound, the second aromatic compound and / or the third aromatic compound and oxygen or the oxygen-containing gas mixture are metered continuously or stepwise, preferably continuously, into the second reactor.

[0178] In a seventy-ninth embodiment, the invention relates to a process according to any one of the seventy-second to seventy-eighth embodiments, wherein the arene oxide, the pyridine N-oxide and / or the pyrimidine N-oxide is withdrawn continuously or stepwise, preferably continuously, from the second reactor.

[0179] In an eightieth embodiment, the invention relates to a process according to one of the seventy-second to seventy-ninth embodiments, wherein the catalyst (C) is metered continuously or stepwise, preferably continuously, into the second reactor.

[0180] In an eighty-first embodiment, the invention relates to a process according to any one of the seventy-second to eightieth embodiments, wherein the second reactor is a stirred tank, flow tube, bubble column, loop reactor, trickle bed reactor, spray tower reactor or falling film reactor.

[0181] In an eighty-second embodiment, the invention relates to a process according to one of the seventy-second to eighty-first embodiments, wherein the arene oxide, pyridine N-oxide and / or pyrimidine N-oxide produced in the second reactor is metered continuously or stepwise, preferably continuously, into the first reactor.

[0182] In an eighty-third embodiment, the invention relates to a process according to any one of the first to eighty-second embodiments, wherein the alkene is one or more compound(s) and is selected from the group consisting of ethene, propene, butene, 1-octene, butadiene, 1,4-butanediol diallyl ether, allyl chloride, allyl alcohol, styrene, cyclopentene, cyclohexene, phenyl allyl ether, diallyl ether, n-butyl allyl ether, tert-butyl allyl ether, bisphenol A diallyl ether, resorcinol diallyl ether, triphenylolmethane triallyl ether, cyclohexane-1,2-dicarboxylic acid bis-(allyl ester), isocyanuric acid tris-(prop-2,3-ene) ester and mixtures of these alkenes, preferably ethene, propene and allyl chloride and particularly preferably propene. Examples Chemicals used

[0183] Copper, powder, 99.999% Sigma Aldrich Copper monochloride, ≥ 99.995%, Sigma Aldrich Silver, powder, 2-3.5 µm, ≥ 99.9%, Sigma Aldrich Iron(III) chloride, ≥ 99.99%, Sigma Aldrich Chromium(III) chloride, 99.99%, Sigma Aldrich Ruthenium(III) chloride hydrate, 99.98%, Sigma Aldrich

[0184] All chemicals were used as received. Gas chromatography analysis

[0185] Gas chromatographic (GC) analysis of liquid and gas samples was performed according to "Determine Impurities in High-Purity Propylene Oxide with Agilent J&W PoraBOND U" by Dianli Ma, Ningbo ZRCC Lyondell Chemical Co., Ltd., Zhejiang, China, and Yun Zou, Hua Wu, Agilent Technologies, Inc. Propene conversions, propylene oxide yields, and selectivities were determined based on GC. Simulation method

[0186] All quantum mechanical calculations were performed using the TURBOMOLE software package, version 7.4.1, from Cosmologic GmbH & Co. KG. The density functional theory method used was the TPSS density functional, implemented as unrestricted DFT for spin contamination of open-shell systems, with a def2-SVP basis set, as implemented by default in the Turbomole software package. The obtained energies were refined using the described DFT method and a def2-TZVP quality basis set. Fig. 1: Input geometry for the quantum chemical calculations of the transition states of the catalyzed oxygen transfer.

[0187]

[0188] Transition states were calculated using gradient-based Monte Carlo, as described in application WO 2020 / 079094 A2. For this purpose, a structure corresponding to transition state T1 was drawn (Figure 1). The bonds shown in bold were set to an atomic distance of 1.90 Å (190 pm), and the resulting structure was translated into Cartesian coordinates. The atom indices in the Cartesian coordinate set of the bonds shown in bold in Figure 1 were set as function space in the gradient-based Monte Carlo program, and the Monte Carlo procedure was repeated until the corresponding transition states T1 were obtained. The resulting Cartesian coordinates of the structures T1 were then manipulated to obtain the corresponding reactant-catalyst complexes and the corresponding catalyst-product complexes.For this purpose, the bold bond (Figure 1) between oxygen and the aromatic carbon atom of the haloaromatic compound was i) lengthened and ii) shortened by 0.20 Å (20 pm). The resulting structures i) and ii) were converted into Cartesian coordinates, subjected to geometry optimization using the described DFT method, and the resulting geometries were used to calculate the activation energies.

[0189] Arene oxides of hexafluorobenzene and hexachlorobenzene, as well as pentafluoropyridine N-oxide, were identified as suitable oxidation mediators for the selective oxidation of propene to propylene oxide using quantum chemical simulations (working examples). Hexafluorobenzene and hexachlorobenzene can be readily converted into the respective arene oxides, are inert to unwanted decomposition reactions, and selectively transfer the atomic oxygen to the propene with exclusive PO formation (see Fig. 2). The same applies to pentafluoropyridine N-oxide. Arene oxides of various halogenated benzenes are also commercially available.

[0190] To experimentally demonstrate the usability of such arene oxides and structurally related pyridine N-oxides for the formation of alkylene oxide, quantum chemical simulations were carried out in which the transfer of bound oxygen to the propene was investigated. In the case of arene oxides, the bound oxygen atom is transferred to the double bond of the propene, resulting in rearomatization of the aromatic hydrocarbon. In the case of pentafluoropyridine N-oxide, the electronically uncharged pyridine bond system is formed. The regeneration of the aromatic systems serves as the driving force for the transfer of oxygen to the propene. In both compound classes, comprehensive and selective recovery of the starting components occurs through oxygen transfer. Recovery and reoxidation with formation of the oxidation mediator structure is therefore always possible.The starting compounds of the oxidation mediators are recycled. Fig.2: Reaction sequence of the catalytic formation of the arene oxide in the presence of catalyst (D) followed by the oxidation of propene with an arene oxide using catalyst (A).

[0191] Tab.1: Overview of simulated activation energies of oxygen transfer to propene with different oxidation mediators. Oxidation promoter oxide Ea, simulated [kcal / mol] Hexafluorobenzene oxide 27.3 Hexachlorobenzene oxide 21.6 Pentafluoropyridine N-oxide 32.5

[0192] The values ​​shown in Table 1 suggest that, in the case of hexachlorobenzene oxide, alkoxylation of propene (epoxidation of propene, propoxylation) can be achieved simply by using appropriate reaction temperatures without the need for additional aids such as specific catalysts. For hexafluorobenzene oxide and pentafluoropyridine N-oxide, however, the calculated activation energies indicate the additional use of a suitable catalyst to enable the epoxidation of propene.

[0193] Metallic silver, metallic copper, copper(I) chloride, iron(III) chloride and chromium(III) chloride were identified as suitable catalysts (A) by means of quantum chemical simulations (working examples). Table 2: Overview of simulation-calculated activation energies of the oxygen transfer from hexafluorobenzene oxide to propene with different catalysts (A). Catalyst (A) Ea,simulated [kcal / mol] Uncatalyzed, hexafluorobenzene oxide 27.3 Ag(0) 17.4 Cu(0) 18.2 NiCl 2 En 2 (cf.) 28.0 Fe(III)Cl 3 14.3 Cr(III)Cl 3 17.3

[0194] The calculated values ​​in Table 2 show that the activation energy of the uncatalyzed reaction of 27.3 kcal / mol can be significantly reduced by the catalysts (A). Furthermore, the simulated results demonstrate that the activation energies depend significantly on the specific catalyst (A). In the case of hexachlorobenzene oxide, the calculated activation energy of 21.6 kcal / mol is already advantageous without the use of a catalyst (A). Table 3: Overview of simulation-calculated activation energies of the oxygen transfer from pentafluoropyridine N-oxide to propene. Catalyst (A) Ea, simulated (propoxylation) [kcal / mol] Ea, simulated, side reaction [kcal / mol] Uncatalyzed (cf.) 32.5 Ag(0) 15.2 22.7 Au(0) 11.2 20.2 Cu(0) 10.3 19.9 Cu(II)Cl 2 14.0 33.7 Cr(III)Cl 3 15.9 19.6 Co(0) (cf.) 26.3 30.1 Co(II)Cl 2 20.5 30.3 Ru(III)Cl 3 (cf.) - 1)< 25.3 Ru(II)Cl 2 (cf.) - 1)< - [Pt(II)Cl 3 ] -< (cf.) 41.6 - 1) Instead of propylene oxide or corresponding intermediates, further leads to CC cleavage of propylene (bond distance on the product side is 3.112 Å to 4.124 Å in the simulations, while the calculated CC bond distance for propylene oxide is 1.475 Å).

[0195] Table 3 shows the simulated activation energies for the epoxidation of propene with hexafluopyridine N-oxide with and without catalysts. The calculated values ​​show that the activation energy of the uncatalyzed reaction of 32.5 kcal / mol can be significantly reduced by the catalysts A used (see column "Ea, simulated (propoxylation)"). 1) Alkoxylation of propene with hexachlorobenzene oxide:

[0196] Hexachlorobenzene oxide was obtained according to the state of the art by catalytic oxidation of hexachlorobenzene. A 1 M solution of hexachlorobenzene oxide in perfluorodecalin was produced. 200 mL of perfluorodecalin were then placed under inert conditions in a pressure-resistant 1 L reactor equipped with a stirrer, overpressure relief valve, pressure sensor, riser tube for liquid withdrawal, and gas and vent lines. The reaction vessel was then pressurized with 0.400 mol of propene (approx. 11 bar). The internal reactor temperature was adjusted to 135°C, and 0.400 mol of hexachlorobenzene oxide in the form of the previously prepared perfluorodecalin solution was added over 30 min. The reaction progress and endpoint were determined based on the pressure profile and by taking liquid and gas samples and analyzing them by GC.After completion of the reaction, the reactor was cooled to 40 °C, then depressurized and the reaction product propylene oxide was distilled via the degassing line into a cooled receiver.

[0197] The theoretical yield of propylene oxide is 23.2 g. 2) Alkoxylation of propene with hexachlorobenzene oxide:

[0198] 200 mL of perfluorodecalin, 0.400 mol of hexachlorobenzene, and 0.040 mol of silver (powder, 2-3.5 µm) were placed in a pressure-resistant 1 L reactor equipped with a stirrer, overpressure protection, pressure sensor, riser tube for liquid withdrawal, and gas and vent lines under inert conditions and stirred vigorously. The reaction vessel was then pressurized with 0.400 mol of oxygen. The internal reactor temperature was adjusted to 200°C, and the pressure gradient was monitored until constant. The reaction vessel was then cooled to 135°C, inertized with nitrogen, and 0.400 mol of propene was added. The reaction progress and endpoint were determined based on the pressure gradient and by taking liquid and gas samples and analyzing them by GC. After the reaction was complete, the reactor was cooled to 40 °C, then depressurized, and the reaction product, propylene oxide, was distilled via the degassing line into a cooled receiver. The theoretical yield of propylene oxide was 23.2 g. 3) Alkoxylation of propene with hexafluorobenzene oxide:

[0199] Hexafluorobenzene oxide was obtained by partial oxidation of hexafluorobenzene with oxygen in a pressure reactor. The hexafluorobenzene conversion was selected such that the hexafluorobenzene oxide concentration was 1 mol / L (1 M). 200 mL of hexafluorobenzene and, for each experiment, 0.020 mol of the respective catalysts identified as examples in Table 2 were placed under inert conditions in a pressure-resistant 1L reactor equipped with a stirrer, overpressure protection, pressure sensor, riser tube for liquid removal, and gassing and degassing lines. The reaction vessel was then pressurized with 0.400 mol of propene (approx. 11 bar). The internal reactor temperature was adjusted to 60°C, and 0.400 mol of hexafluorobenzene oxide in the form of the previously prepared solution was added over 30 min. The reaction progress and end point were determined based on the pressure curve and by taking liquid and gas samples and analyzing them by GC.After completion of the reaction, the reactor was cooled to 40 °C, then depressurized and the reaction product propylene oxide was distilled via the degassing line into a cooled receiver.

[0200] The theoretical yield of propylene oxide is 23.2 g in all five experiments. 4) Alkoxylation of propene with hexafluorobenzene oxide:

[0201] The continuous epoxidation of propene with hexafluorobenzene oxide was carried out analogously to Experimental Procedure 3. However, the hexafluorobenzene oxide and propene were continuously metered into the reactor (molar ratio 1.05:1), and the reaction mixture was removed volumetrically in the same manner and subjected to distillation. The mass and volume flows were adjusted to achieve a residence time of 90 minutes. After 6 hours, the reaction reached steady state. Conversions and selectivities analogous to Experiment 3 were observed in all experiments using the different inventive catalysts from Table 2. 4) Alkoxylation of propene with hexafluorobenzene oxide:

[0202] The continuous epoxidation of gaseous propene with gaseous hexafluorobenzene oxide was carried out analogously to Experimental Procedure 4. However, the hexafluorobenzene oxide and propene were vaporized and continuously fed into an inerted, pressure-resistant, and pressure-protected flow reactor containing silver (powder, 2-3.5 µm) as a solid catalyst. The molar ratio was 5:1 hexafluorobenzene oxide to propene, and a reaction temperature of 120 °C was maintained. Partial conversions of propene and propylene oxide selectivities analogous to Experiments 3 and 4 were observed. No precise residence times were determined. 5) Epoxidation of propene with pentafluoropyrimidine N-oxide:

[0203] Pentafluoropydine N-oxide was prepared analogously to the state of the art for N-oxides (Chem. Commun. 2002, pp. 1040-1041) and prepared as a 1 M dichloroethane solution. 200 mL of dichloroethane and 0.020 mol of the respective catalysts (identified as examples in Table 3) for each experiment were placed under inert conditions in a pressure-resistant 1 L reactor equipped with a stirrer, overpressure protection, pressure sensor, riser tube for liquid removal, and gassing and degassing lines. The reaction vessel was then pressurized with 0.400 mol of propene (approx. 11 bar). The internal reactor temperature was adjusted to 60°C, and 0.400 mol of pentafluoropydine N-oxide in the form of the previously prepared solution was added over 30 min. The reaction progress and end point were determined based on the pressure curve and by taking liquid and gas samples and analyzing them by GC.After the reaction was complete, the reactor was cooled to 40 °C, then depressurized, and the reaction product, propylene oxide, was distilled via the degassing line into a cooled receiver. The theoretical yield of propylene oxide in all five experiments was 23.2 g.

Claims

1. Process for producing an alkylene oxide by reacting an alkene with an arene oxide, pyridine N-oxide and / or pyrimidine N-oxide, preferably with an arene oxide and / or pyridine N-oxide, in the presence of a catalyst (A) in a first reactor, wherein the catalyst (A) comprises a metal (A-1) and / or a metal salt (A-2), wherein the metal (A-1) is copper, silver and / or gold, wherein the metal salt (A-2) comprises chromium (Cr), iron (Fe), cobalt (Co) and / or copper (Cu) cation(s), and wherein the reaction is effected in the absence of oxygen or an oxygen-containing gas mixture.

2. Process according to Claim 1, wherein the alkylene oxide is one or more compound(s) and is selected from the group consisting of ethylene oxide, propylene oxide, 1,2-butylene oxide, 1,2-pentylene oxide, 1,2-hexylene oxide, 1,2-heptylene oxide and 1,2-octylene oxide, preferably ethylene oxide and propylene oxide, more preferably propylene oxide.

3. Process according to Claim 1 or 2, wherein the alkene is one or more compound(s) and is selected from the group consisting of ethene, propene, butene, 1-octene, butadiene, butane-1,4-diol diallyl ether, allyl chloride, allyl alcohol, styrene, cyclopentene, cyclohexene, phenyl allyl ether, diallyl ether, n-butyl allyl ether, tert-butyl allyl ether, bisphenol A diallyl ether, resorcinol diallyl ether, triphenylolmethane triallyl ether, cyclohexane-1,2-dicarboxylic acid bis(allyl ester), isocyanuric acid tris(prop-2,3-ene) ester and mixtures of these alkenes, preferably ethene, propene and allyl chloride, and more preferably propene.

4. Process according to any of Claims 1 to 3, wherein the arene oxide is one or more compound(s) and is selected from the group consisting of hexafluorobenzene oxide, hexachlorobenzene oxide, 1-bromo-2,3,4-trifluorobenzene oxide, pentafluorobenzene oxide, 1,3,5-trichloro-2,4,6-trifluorobenzene oxide, 1,3,5-trifluorobenzene oxide, 1,2-dibromo-3,5-difluorobenzene oxide, 1,2,4,5-tetrafluorobenzene oxide, bromopentafluorobenzene oxide, 1,3,5-trichlorobenzene oxide, 1-bromo-3,5-dichlorobenzene oxide, orthodichlorobenzene oxide, 1,2,4,5-tetrachlorobenzene oxide, 1,2,3-trichlorobenzene oxide and 1,5-dichloro-2-fluorobenzene oxide, preferably hexafluorobenzene oxide and hexachlorobenzene oxide.

5. Process according to any of Claims 1 to 4, wherein the pyridine N-oxide is one or more compound(s) and is selected from the group consisting of pentafluoropyridine N-oxide, 2-bromo-3,5-dichloropyridine N-oxide, 3-chloropyridine N-oxide, 3,6-dichloropyridine N-oxide, 3,5-dichloropyridine N-oxide, 3-chloro-2,5,6-trifluoropyridine N-oxide, 3-chloro-2,4,5,6-tetrafluoropyridine 1-N-oxide, 3-chloro-2,4,5,6-tetrafluoropyridine 3-N-oxide, preferably pentafluoropyridine N-oxide.

6. Process according to any of Claims 1 to 5, wherein the pyrimidine N-oxide is one or more compounds and is selected from the group consisting of 2-chloropyrimidine N-oxide, 2,4-dichloro-6-methylpyrimidine 1-N-oxide, 2,4-dichloro-6-methylpyrimidine 3-N-oxide, 2,5-dichloropyrimidine 1-N-oxide, 2,5-dichloropyrimidine 2-N-oxide.

7. Process according to any of Claims 1 to 6, wherein the metal (A-1) is copper (Cu), silver (Ag) and / or gold (Au), preferably silver (Ag).

8. Process according to any of Claims 1 to 7, wherein the metal cation of the metal salt (A-2) has an oxidation state of (+I), (+II); (+III) or (+IV), preferably of (+II); (+III) or (+IV).

9. Process according to any of Claims 1 to 8, wherein the metal salt (A-2) is one or more compound(s) and is selected from the group consisting of Cr2(SO4)3, KCr(SO4)2, Cr(NO3)3, CrF3, CrCl3, FeCl3, FeBr3, iron triflate, FePO4, Fe2(SO4)3, Fe(NO3)3, FeF3, iron paratoluenesulfonate, CoCl2, CoBr2, Co(NO3)2, CoBr2, CoSO4, CoF2, Co(BF4)2, Co3(PO4)2, CuCl2, CuSO4, (CF3SO3)2Cu CuF2, Cu(NO3)2, copper(II) pyrophosphate, CuCl, CuI and CuBr, preferably CrCl3, FeCl3, CoCl2 and CuCl2.

10. Process according to any of Claims 1 to 9, wherein the production of the alkylene oxide is effected in the presence of a solvent.

11. Process according to any of Claims 1 to 9, wherein the production is effected in the absence of a solvent.

12. Process according to any of Claims 1 to 11, wherein the alkene and the arene oxide, pyridine N-oxide and / or the pyrimidine N-oxide are / is metered into the first reactor continuously or stepwise, preferably continuously.

13. Process according to any of Claims 1 to 12, wherein the alkylene oxide is withdrawn from the first reactor continuously or stepwise, preferably continuously.

14. Process according to any of Claims 1 to 13, wherein the arene oxide, the pyridine oxide and / or the pyrimidine N-oxide are / is produced in a second reactor, wherein the second reactor is not the same as the first reactor.

15. Process according to Claim 14, wherein the arene oxide, pyridine N-oxide and / or pyrimidine N-oxide produced in the second reactor are / is metered into the first reactor continuously or stepwise, preferably continuously.