A process for preparing at least one hydrocarbon from at least one alcohol

Abstract

The present invention relates to a process for preparing at least one hydrocarbon R-CH2-CH2- (CHR-CH2)x-H, wherein at least one alcohol R-CH2-CH2-OH, wherein R is selected from the group consisting of H, C1-C10 alkyl, C5-C10 aryl, and a mixture of two or more thereof, a base, at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor and a reducing agent is provided. The obtained at least one hydrocarbon R-CH2- CH2-(CHR-CH2)x-H may be employed as an additive to or as a substitute for naphtha.

Description

[0001] A process for preparing at least one hydrocarbon from at least one alcohol

[0002] The present invention relates to a process for preparing hydrocarbons from alcohols.

[0003] A commonly used industrial production of alcohols is mainly based on an oxo process. Said process comprises the reaction of an alkene with oxo gas, which is a mixture of hydrogen and carbon monoxide in a 1 :1 molar ratio. The reaction is followed by hydrogenation of the aldehyde into the desired alcohol.

[0004] An alternative process for the synthesis of alcohols is based on the homogeneous Guerbet reaction is well known as a possible approach to condensation of alcohols. This process is known for many decades (M. Guerbet, C. R. Hebd. Seances Acad. Sci. 1899, 128, p. 511-513). It is generally accepted that the mechanism leading to Guerbet alcohols comprises the following three steps: (i) dehydrogenation of a primary alcohol to the respective aldehyde; (ii) aldol condensation of two aldehyde molecules to an a,p-unsaturated aldehyde with elimination of water; and (iii) hydrogenation of the unsaturated aldehyde to the dimer alcohol. An alkaline catalyst, e.g. sodium or potassium hydroxide or sodium or potassium alkoxides, is required for the Guerbet reaction. Often homogeneous or hetereogeneous metal catalysts are added to accelerate the dehydrogenation and hydrogenation steps. However, the Guerbet reaction generally suffers from harsh conditions, poor selectivity, separation issues and low yield.

[0005] In the chemical industry, butanol is an important intermediate product and solvent for a broad variety of products, including paints and various plastics. Up to now, butanol is produced from a petro-based feedstock, leading to a significant product carbon footprint for butanol and the resulting products, such as hydrocarbons. Therefore, it is important for the chemical industry to find and open an economical and sustainable process route to hydrocarbons with a lower product carbon footprint.

[0006] Ethanol may be a sustainable feedstock to produce chemicals. Using ethanol in the Guerbet reaction may be a profitable and sustainable approach to produce hydrocarbons from butanol. Because the product of the Guerbet reaction, n-butanol, can itself also undergo dehydrogenation, higher alcohols often result as side products in the process. Additionally, the formation of higher alcohols containing multiplicity of the ethanol substructure as side product is also observed. In particular hexanol, octanol, decanol, dodecanol are formed. Furthermore, minor amounts of side products like ethers, aldehydes and esters containing more than six carbon atoms are also formed. Due to complexity of the side product mixture, a separation of particular C-6 and higher alcohols is difficult and energy consuming.

[0007] US 2021 / 154110 A1 relates to a cosmetic excipient comprising a mixture of alkanes, the mixture of alkanes comprising at least one C8-C10 alkane, and at least one C>11 alkane, wherein the at least one C8-C10 alkane is present in a mass percentage less than or equal to approximately 50% (<50%), relative to the total mass of the mixture of alkanes, wherein it is entirely obtained from raw materials of plant, bacterial, or animal origin and that the mixture of alkanes is free of alkanes with an odd carbon number N.Antil et al., “Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols”, Inorganic Chemistry, vol. 60, no. 12, 2021-06-04, pages 9029 to 9039, relates to a study of an aluminum metal-organic framework (DUT-5) node support cobalt(ll) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2.

[0008] X.J. Dai et aL, “En Route to a Practical Primary Alcohol Deoxygenation”, Journal of the American Society, vol. 138, no. 16, 2016-04-18, pages 5433 to 5440, relates to a catalytic late-transi- tion-metal-catalyzed redox design, on the basis of dehydrogenation / Wolff-Kishner reduction. Disclosed is an aliphatic primary alcohol deoxygenation by employing a ruthenium complex.

[0009] WO 2014 / 159484 A1 discloses a hydrodeoxygenation process for producing a linear alkane from a feedstock comprising a saturated or unsaturated C10-18 oxygenate that comprises an ester group, carboxylic acid group, carbonyl group and / or alcohol group.

[0010] US 2015 / 246863 A1 discloses a method and system for preparing a mixture of Guerbet alcohols where one or more primary alcohols of the formula RCH2CH2OH are provided, with R representing hydrogen or a straight or branched chain alkyl group of 1 to 14 carbon atoms. A base and a catalyst are provided, which are mixed with the primary alcohol(s). The resulting mixture is heated to a process temperature above the boiling point of water under reaction conditions and the water resulting from the thus obtained condensation and dehydration of the primary alcohols is then removed constantly. When the Guerbet reaction has reached a certain stage, at least part of the reaction mixture is removed, followed by a separation of the desired Guerbet alcohols from the removed part of the reaction mixture.

[0011] Y.Xie et aL, “Highly efficient Process for Production of Biofuel from ethanol Catalyzed by Ruthenium Pincer Complexes”, Journal of the American Society, vol. 138, no. 29, 2016-07-18, pages 9077 to 9080, relates to a ruthenium pincer-catalyzed Guerbet-type process for the production of biofuel from ethanol.

[0012] WO 2013 / 156399 A1 relates to a method for producing branched alcohols using at least one alcohol of formula R1-CH2-CH2-OH, the groups R1being different or the same and being selected from C2-C3 alkyl, linear or branched, in a homogeneous phase in the presence of at least one base, characterized in that at least one complex compound containing Ru(ll) is used, in which the Ru(ll) has at least one ligand L1, which is at least bidentate, at least one coordination site of L1being a nitrogen atom.

[0013] Therefore, it was an object of the present invention to provide a process for preparing hydrocarbons to avoid a loss of the energy accumulated in the obtained Guerbet products by their conversion into the hydrocarbons, the so-called bio-naphta. Bio-naphtha is a mixture of alkanes containing between six to and sixteen carbon atoms. The present invention relates to a profitable and sustainable approach to produce hydrocarbons from Guerbet alcohols in a way such that the employed Guerbet catalyst is recycled in the chemical process.

[0014] The present invention in particular relates to a process for preparing at least one hydrocarbon R-CH2-CH2-(CHR-CH2)X-H, the process comprising

[0015] (i) providing at least one alcohol R-CH2-CH2-OH, wherein R is selected from the group consisting of H, C1-C10 alkyl, C5-C10 aryl, and a mixture of two or more thereof, a base, at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor and a reducing agent;

[0016] (ii) preparing a liquid mixture ME comprising the at least one alcohol R-CH2-CH2-OH, the base, and the at least one of the catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor provided according to (i);

[0017] (iii) subjecting the liquid mixture ME prepared according to (ii) to alcohol conversion conditions in a reaction space SG, obtaining in said reaction space SG a liquid reaction mixture MG comprising at least one alcohol R-CH2-CH2-(CHR-CH2)x-OH, x is an integer in the range of from 1 to 10, the liquid reaction mixture MG further comprising the catalyst;

[0018] (iv) separating the at least one alcohol R-CH2-CH2-(CHR-CH2)X-OH from the liquid reaction mixture MG, obtaining the at least one alcohol R-CH2-CH2-(CHR-CH2)X-OH and a mixture Me comprising the at least one of a catalyst, precursor thereof, reduced form of the catalyst or reduced form of the precursor;

[0019] (v) preparing a liquid mixture Mi comprising the at least one alcohol R-CH2-CH2-(CHR-CH2)X- OH separated from MG according to (iv) and further comprising the reducing agent provided according to (i);

[0020] (vi) subjecting the liquid mixture Mi prepared according to (v) to alcohol reduction conditions in a reaction space SR, obtaining in said reaction space SR a liquid reaction mixture MR comprising the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)X-H; wherein the base is selected from the group consisting of ammonium hydroxide, alkali hydroxides, alkaline earth hydroxides, ammonium carbonate, ammonium hydrogen carbonate, alkali carbonates, alkali hydrogen carbonates, alkaline earth carbonates, alkaline hydrogen carbonates, alkali alkoxides, alkaline earth alkoxides, alkali metal amides, alkaline earth metal amides, secondary amino acids, and a mixture of two or more thereof; the at least one of a catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor comprises a metal selected from the group consisting of Al, Ca, Fe, Co, Ni, Cu, Ir, Mn, Os, Pd, Pt, Rh, Ru, and a mixture of two or more thereof; and the reducing agent is selected from the group consisting of a redox catalyst and a hydride compound, wherein the redox catalyst comprises a transition metal, and the hydride compound is selected from the group consisting of a silane, an alkali hydride, an alkaline earth hydride, an aluminum hydride, an alkali aluminum hydride, an alkali borohydride, a hydrogen halide, and a mixture of two or more thereof. Preferably, according to (i), a solvent is additionally provided, wherein the liquid mixture ME prepared according to (ii) additionally comprises said solvent, and wherein the mixture Me obtained according to (iv) additionally comprises said solvent.

[0021] Preferably, the solvent has a boiling point of 110 °C or more, more preferably a boiling point of 140 °C or more, more preferably a boiling point of 160 °C or more, more preferably a boiling point of 180 °C or more, more preferably a boiling point of 190 °C or more.

[0022] Preferably, the solvent has a solubility in water at 25 °C of from 0 to 1 weight-%, more preferably from 0 to 0.5 weight-%, preferably a solubility in water at 25 °C of from 0 to 0.1 weight-%, more preferably a solubility in water at 25 °C of from 0 to 0.05 weight-%, more preferably a solubility in water at 25 °C of from 0 to 0.01 weight-%, based on 100 weight-% water.

[0023] Preferably, the distribution coefficient of the catalyst in a system of the solvent and water is from 0 to 0.01 , more preferably from 0 to 0.005, more preferably from 0 to 0.005, based on 1 kg catalyst.

[0024] Preferably, the solvent is a mixture of at least two aromatic hydrocarbons with a boiling point of 180 °C or more.

[0025] Preferably, the solvent is selected from the group consisting of biphenyl, diphenyl ether, 1-tert- butyl-3,5-dimethyl-benzene, ethylbenzene, cyclododecane, cyclononane, cyclooctane, cycloheptane, decaline, n-butylbutyrate, n-hexylhexyrate, n-octyloctyrate, texanole, di-n-butylether, di-iso-butylether, di-sec-butylether, and a mixture of two or more thereof, more preferably from the group consisting of biphenyl, diphenyl ether, and a mixture thereof, wherein more preferably, the solvent is a mixture of biphenyl and diphenyl ether.

[0026] In a preferred embodiment, the solvent does not include any one of benzene, toluene, xylene or mesitylene.

[0027] Preferably, the solvent does not form an azeotrope with water. An azeotrope or a constant heating point mixture is a mixture of two or more components in fluidic states whose proportions cannot be altered or changed by simple distillation. This happens because when an azeotrope is boiled, the vapour has the same proportions of constituents as the unboiled mixture. Each azeotrope has a characteristic boiling point. It is not possible to separate the components by fractional distillation.

[0028] Preferably, the solvent is a mixture of biphenyl and diphenyl ether, more preferably at a molar ratio of biphenyl relative to diphenyl ether in the range of from 1 :2 to 1 :6, more preferably in the range of from 1 :2.5 to 1 :4. Preferably, at least a part of the solvent comprised in the mixture Me obtained according to (iv) is recycled to (ii).

[0029] Preferably, at least a part of the at least one of a catalyst, precursor thereof, reduced form of the catalyst or reduced form of the precursor comprised in the mixture Me obtained according to (iv) is recycled to (ii) or (iii).

[0030] Preferably, the liquid reaction mixture MG obtained according to (iii) further comprises at least one unreacted alcohol R-CH2-CH2-OH.

[0031] It is preferred that the process of present invention comprises separating at least a part of said unreacted alcohol R-CH2-CH2-OH from the liquid reaction mixture MG.

[0032] Preferably, separating at least a part of the unreacted alcohol R-CH2-CH2-OH from MG is carried out by distillation, extraction, flashing, or by employing a membrane.

[0033] Preferably, at least a part of the at least one unreacted alcohol R-CH2-CH2-OH separated from MG is recycled to (ii) or (iii).

[0034] Preferably, the process of the present invention further comprises

[0035] (vii) separating the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H from the liquid reaction mixture MR.

[0036] Preferably, separating the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H according to (vii) is carried out by distillation, extraction, flushing, extractive distillation with monoethylene glycol, and employing a membrane, preferably by distillation or extraction.

[0037] In case where the separating the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)X-H according to (vii) is carried out by employing a membrane, pervaporation or gas phase permeation is preferred.

[0038] Preferably, integer x is in the range of from 2 to 10, preferably in the range of from 2 to 8, more preferably in the range of from 2 to 6.

[0039] Preferably, the at least one alcohol provided according to (i) comprises ethanol and the at least one alcohol R-CH2-CH2-(CHR-CH2)X-OH separated according to (iv) and comprised in Mi comprises H-CH2-CH2-(CHR-CH2)X-OH.

[0040] Preferably, for H-CH2-CH2-(CHR-CH2)X-OH, integer x is in the range of from 2 to 10, preferably in the range of from 2 to 8, more preferably in the range of from 2 to 6. Preferably, the liquid mixture MR obtained according to (vi) comprises at least one hydrocarbon H-CH2-CH2-(CHR-CH2)X-H, wherein integer x is an integer in the range of from 2 to 10, preferably in the range of from 2 to 8, more preferably in the range of from 2 to 6.

[0041] Preferably, from 90 to 100 weight-%, preferably wherein from 95 to 100 weight-%, more preferably from 98 to 100 weight-%, more preferably 99 to 100 weight-% of the liquid mixture ME prepared according to (ii) consist of the at least one alcohol R-CH2-CH2-OH, the base, the at least one of a catalyst, the precursor thereof, or the reduced form of the catalyst or the precursor and optionally the solvent as defined in accordance with the present invention.

[0042] Preferably, preparing a liquid mixture ME in step (ii) comprises at least one alcohol R-CH2-CH2- OH, a base, and the at least one of a catalyst, or precursor thereof provided according to (i) and optionally the solvent as defined according to the present invention.

[0043] The process in accordance with the present invention is preferably a continuous process. Alternatively, the process is preferably a semi-batch process or a batch process.

[0044] The alcohol conversion conditions according to (iii) preferably comprise the presence of at least one inert gas in the reaction space SG, wherein the at least one inert gas is preferably selected from the group consisting of nitrogen, argon, and a mixture thereof.

[0045] The alcohol conversion conditions according to (iii) preferably comprise a pressure in the reaction space SG in the range of from 1 x 105to 3.5 x 106Pa, more preferably in the range of from 1 x 105to 3.1 x 106Pa, more preferably in the range of from 1 x 105to 2 x 106Pa, more preferably in the range from 1 x 105to 1 .5 x 106Pa.

[0046] Preferably, the alcohol conversion conditions according to (iii) comprise a temperature of the reaction mixture MG in the reaction space SG in the range of from 100 to 200 °C, more preferably in the range of from 120 to 180 °C, more preferably in the range of from 130 to 160 °C.

[0047] Preferably, the alcohol conversion conditions according to (iii) comprise an amount of the base in the reaction mixture MG in the reaction space SG in the range of from 0.1 to 10 weight -%, more preferably in the range of from 0.5 to 8 weight-%, more preferably in the range of from 1 to 5 weight-%, based on the total weight of the mixture MG.

[0048] Preferably, the alcohol conversion conditions according to (iii) comprise an amount of the catalyst in the reaction mixture MG in the reaction space SG in the range of from 0.001 to 2 weight-%, more preferably in the range of from 0.001 to 1 weight-%, more preferably in the range of from 0.001 to 0.5 weight-%, based on the total weight of the mixture MG.

[0049] Preferably, the reducing agent provided according to (i) and comprised in the liquid mixture Mi according to (v) comprises a redox catalyst, wherein the redox catalyst comprises a transition metal selected from the group consisting of Pd, Rh, Ni, Ru, Pt, Re, Co, Ir, and a mixture of two or more thereof.

[0050] The redox catalyst in accordance with the present invention preferably further comprises a support material, wherein more preferably the support material is selected from the group consisting of a heteropolyacid, a sulfonic acid resin, carbon, a metal oxide, a metalloid oxide, and a mixture of two or more thereof.

[0051] The heteropolyacid comprises a metal and a metalloid oxide, wherein the metal is selected from the group consisting of W, Mo, and V and the oxide is selected from the group consisting of Si, P, and As, preferably the heteropolyacid is selected from the group consisting of H3PM012O40, H3PW12O40, HsPMoeVeC o, H5PM010V2O40, and a mixture of two or more thereof.

[0052] The metal oxide and / or a metalloid oxide comprised in the support comprises an oxide selected from the group consisting of oxides of Si, Al, Ti, Zr, Hf, La, Ce, Pr, Nd, and a mixture of two or more thereof and / or mixed oxides of two or more thereof, more preferably from the group consisting of oxides of Si, Al, Ti, Zr, and a mixture of two or more thereof and / or mixed oxides of two or more thereof, wherein more preferably the support material is selected from the group consisting of activated carbon, silica, alumina, silica-alumina, aluminosilicates, titanosilicates, and mixtures of two or more thereof, wherein more preferably the support material comprises activated carbon and / or aluminosilicate, preferably sodium aluminosilicate, wherein more preferably the support material consists of activated carbon and / or aluminosilicate, preferably of sodium aluminosilicate.

[0053] The alcohol reduction conditions according to (vi) preferably comprise the presence of at least one inert gas and H2 in the reaction space SR, wherein the at least one inert gas is preferably selected from the group consisting of nitrogen, argon, and a mixture thereof.

[0054] The alcohol reduction conditions according to (vi) preferably comprise a temperature of the reaction mixture MR in the reaction space SR in the range of from 100 to 250 °C.

[0055] The alcohol reduction conditions according to (vi) preferably comprise a pressure in a reaction space SR in the range of from 1 x 105to 1 x 107Pa.

[0056] Alternatively, the reducing agent provided according to (i) and comprised in the liquid mixture Mi according to (v) comprises a hydride compound, wherein the hydride compound is selected from the group consisting of / 7-butylsilane, diethylsilane, diisobutylaluminum hydride, lithium tri- ethoxyaluminohydride, NaH, LiH, CaH2, LiAIFU, NaBH4, Hl / acetic acid, mixed hydrides of AICI3 and LiAIFU, HSiEts comprising B(C6Fs)3, and a mixture of two or more thereof, more preferably selected from the group consisting of / 7-butylsilane, diethylsilane, Hl / acetic acid, mixed hydrides of AICI3 and LiAIH4, HSiEts comprising B(C6Fs)3, and a mixture of two or more thereof. The alcohol reduction conditions according to (vi) preferably comprise the presence of at least one inert gas in the reaction space SR, wherein the at least one inert gas is preferably selected from the group consisting of nitrogen, argon, and a mixture thereof.

[0057] Preferably, the at least one of the catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor provided according to (i) and comprised in the mixture ME comprises a metal selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, Ru, and a mixture of two or more thereof.

[0058] Preferably, the at least one of the catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor provided according to (i) and comprised in the mixture ME is a homogenous catalyst.

[0059] Preferably, the at least one of the catalyst provided according to (i) and comprised in the mixture ME comprises a compound of formula (A) wherein

[0060] M is selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, and Ru;

[0061] L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, S(=O)Ra, heteroaryl containing at least one heteroatom selected from nitrogen and sulfur, AsRaRb, SbRaRb, and a N-het- erocyclic carbene represented by the structures:

[0062] L3is selected from the group consisting of CO, PRaRbRc, AsRaRbRc, SbRaRbRc, SRaRb, RdCN, RdNC, N2, PF3, pyridine, and thiophene;

[0063] R1, R2, R3and R4either are hydrogen, or form together with the pyridyl unit of the catalyst of formula (A) an acridinyl unit, or R1and R2or R3and R4form together with the pyridyl unit of the catalyst of formula (A) a quinolinyl unit; n is 0 or 1 ;

[0064] Y is selected from the group consisting of H, F, Cl, Br, I, OC(=O)CF3, OSO2CF3, CN, CO, OH, OR, NRd2, NH3, NRd3, and Rd2NSO2Rd;

[0065] Ra, Rb, Rc, Rd, R5, R6and R7are, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cio-alkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Ci-Cio-cycloalkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -heterocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -aryl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; and unsubstituted or substituted Cs-C -het- eroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2 and Ci-Cio-alkyl; and

[0066] X is selected from the group consisting of one, two, three, four, five, six, and seven substituents positioned at any carbon atom on the acridinyl unit, or one, two, three, four and five substituents positioned at any carbon atom on the quinolinyl unit, or one substituent positioned at the carbon atom on the pyridyl unit, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl, preferably X is selected from the group consisting of H, Cl, Br, OH, CN, and C1-C5 alkyl; and wherein the precursor of the catalyst comprising a compound of formula (A) comprises a mixture comprising a compound comprising a metal M and at least one component selected from the group consisting of CO, PRaRbRc, SRaRb, RaCN, RaNC, N2, PF3, organic carbonyl compounds, C1-C10- alkyl, Ci-Ci2-cycloalkyl, C2-Ci2-alkenyl, Cs-Cis-cycloalkenyl, Cs-C2o-aryl, CN, CO, OH, OC(=O)CF3, OSO2CF3, hydrides, pyridines, halogenides, hydroxides, and thiophenes; and a compound of formula (H)

[0067] M is selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, and Ru;

[0068] L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, S(=O)Ra, heteroaryl containing at least one heteroatom selected from nitrogen and sulfur, AsRaRb, SbRaRb, and a N-het- erocyclic carbene represented by the structures:

[0069] R1, R2, R3and R4either are hydrogen, or form together with the pyridyl unit of the catalyst of formula (A) an acridinyl unit, or R1and R2or R3and R4form together with the pyridyl unit of the catalyst of formula (A) a quinolinyl unit; n is 0 or 1 ;

[0070] Ra, Rb, Rc, Rd, R5, R6and R7are, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cio-alkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Ci-Cio-cycloalkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -heterocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -aryl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; and unsubstituted or substituted Cs-C -het- eroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2 and Ci-Cio-alkyl;

[0071] X is selected from the group consisting of one, two, three, four, five, six, and seven substituents positioned at any carbon atom on the acridinyl unit, or one, two, three, four and five substituents positioned at any carbon atom on the quinolinyl unit, or one substituent positioned at the carbon atom on the pyridyl unit, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl, preferably X is selected from the group consisting of H, Cl, Br, OH, CN, and C1-C5 alkyl.

[0072] Preferably, preparing a liquid mixture ME in step (ii) comprises at least one alcohol R-CH2-CH2- OH, a base, and the at least one of a catalyst, or precursor thereof provided according to (i).

[0073] Preferably, in formula (A) n is 0 if R1, R2, R3and R4are hydrogen.

[0074] The at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor preferably comprises a compound of formula (B) wherein

[0075] M is selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, and Ru;

[0076] L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, and S(=O)Ra;

[0077] L3is selected from the group consisting of CO, PRaRbRc, SRaRb, RaCN, RaNC, N2, PF3, pyridine, and thiophene;

[0078] R1, R2, R3and R4either are hydrogen, or form together with the pyridyl unit of the catalyst of formula (A) an acridinyl unit; n is 0 or 1 , and if R1, R2, R3and R4are hydrogen, n is 0;

[0079] Ra, Rb, Rcand Rdare, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-C -alkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Ci-C -cycloalkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; Cs-Cw-heterocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S; Cs-C -aryl; and Cs-Cw-heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S;

[0080] Y is selected from the group consisting of H, F, Cl, Br, I, OC(=O)CF3, OSO2CF3, CN, CO, and OH.

[0081] Alternatively, the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor preferably comprises a compound of formula (C) wherein

[0082] M is selected from the group consisting of Ir, Ru, and Mn;

[0083] L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, and S(=O)Ra;

[0084] L3is selected from the group consisting of CO, PRaRbRc, SRaRb, RaCN, RaNC, N2, PF3, pyridine, and thiophene;

[0085] Ra, Rb, Rcand Rdare, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cw-alkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-C -alkyl; unsubstituted or substituted Ci-C -cycloalkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; Cs-Cw-heterocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S; Cs-Cw-aryl; and Cs-Cw-heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S;

[0086] Y is selected from the group consisting of H, F, Cl, Br, I, OC(=O)CF3, OSO2CF3, CN, CO, and OH.

[0087] In another embodiment, the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor preferably comprises a compound of formula (D) wherein

[0088] M is selected from the group consisting of Ir, Ru, and Mn;

[0089] L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, and S(=O)Ra; L3is selected from the group consisting of CO, PRaRbRc, SRaRb, RaCN, RaNC, N2, PF3, pyridine, and thiophene;

[0090] Ra, Rb, Rcand Rdare, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cw-alkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cw-alkyl; unsubstituted or substituted Ci-C -cycloalkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; Cs-Cw-heterocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S; Cs-C -aryl; and Cs-Cw-heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S;

[0091] Y is selected from the group consisting of H, F, Cl, Br, I, OC(=O)CF3, OSO2CF3, CN, CO, and OH.

[0092] Preferably, M is selected from the group consisting of Ir and Ru, more preferably M is Ru.

[0093] Preferably, M is Ru, and the alcohol conversion conditions according to (iii) comprise a temperature of the reaction mixture MG in the range of from 100 to 170 °C, preferably in the range of from 120 to 170 °C, more preferably in the range of from 120 to 160 °C, more preferably in the range of from 130 to 150 °C.

[0094] Preferably, L3is CO.

[0095] Preferably, L1and L2are each (PRaRb), and wherein Raand Rbare Ci-Cio-alkyl, more preferably Raand Rbare each isopropyl or tert-butyl. Alternatively, L1and L2are preferably each (PRaRb), and Raand Rbare Ci-Cio-cycloalkyl, more preferably Raand Rbare each cyclohexyl. Alternatively, L1and L2are each (PRaRb), and Raand Rbare Cs-C -aryl.

[0096] Preferably, Y is selected from the group consisting of F, Cl, Br, and I, more preferably Y is selected from the group consisting of Cl or Br, more preferably wherein Y is Cl.

[0097] Preferably, Y is CO.

[0098] The at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor preferably comprises a compound of formula (E) wherein Cy is cyclohexyl.

[0099] Also preferred is that the reduced form of the catalyst comprises a compound of formula (E’) wherein Cy is cyclohexyl.

[0100] In a further preferred embodiment, the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound of formula (F) wherein iPr is isopropyl.

[0101] Also preferred is that the reduced form of the catalyst comprises a compound of formula (F’) wherein iPr is isopropyl.

[0102] In a further preferred embodiment, the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound of formula (G) wherein tBu is tert-butyl.

[0103] It is also preferred that the reduced form of the catalyst comprises a compound of formula (G’) wherein tBu is tert-butyl. Preferably, the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound comprising a metal M selected from the group consisting of lrCI3x H2O, [lr(COD)CI]2, [lr(COE)2CI]2, [lr(C2H4)2CI]2, [lr(COD)OH]2, [lr(COD)MeO]2, [lrCp*CI2], [IrCp Cl2], lr4(CO)i2, [lr(PPh3)2(CO)CI], [lr(acetylacetonate)3], and [lr(acetylacetonate)(COD)], wherein Cp is cyclopentadienyl, Cp* is pentamethylcyclopentadienyl, COD is 1 ,5-cyclooctadienyl, COE is cyclooctenyl, and methylallyl is 2-methylallyL

[0104] Preferably, the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound comprising a metal M selected from the group consisting of [Ru(p-cymene)Cl2]2, [Ru(benzene)Cl2]y, [Ru(CO)2Cl2]y, where y is in each case in the range from 1 to 1000, [Ru(CO)3Ch]2, [Ru(COD)(allyl)], RuCh x H2O, [Ru(acety- lacetonate)3], [Ru(DMSO)4Cl2], [Ru(cyclopentadienyl)(CO)2CI], [Ru(cyclopentadienyl)(CO)2H], [Ru(cyclopentadienyl)(CO)2]2, [Ru(Cp)(CO)2CI], [Ru(Cp*)(CO)2H], [Ru(Cp*)(CO)2]2, [Ru(in- denyl)(CO)2CI], [Ru(indenyl)(CO)2H], [Ru(indenyl)(CO)2]2, ruthenocene, [Ru(COD)Ch]2, [Ru(Cp*)(COD)CI], [RU3(CO)I2], [Ru(PPh3)4(H)2], [Ru(PPh3)3(CI)2], [Ru(PPh3)3(CO)(CI)2], [Ru(PPh3)3(CO)(CI)(H)], [Ru(PPh3)3(CO)(H)2], and [Ru(cyclooctadienyl)(methylallyl)2], wherein Cp is cyclopentadienyl, Cp* is pentamethylcyclopentadienyl, COD is 1 ,5-cyclooctadienyl, and methylallyl is 2-methylallyL

[0105] Preferably, the reduced form of the precursor comprises a compound of formula (P-l) or (P-ll): wherein R1, R2, R3and R4either are hydrogen, or form together with the N-containing ring a tetrahydroquinoline unit, a decahydroquinoline unit, a tetrahydroacridine unit, or a tetradecahydroacridine unit; and wherein L1and L2are, independently of each other, as defined above; wherein R1, R2, R3and R4are hydrogen; and wherein L1and L2are, independently of each other, as defined above.

[0106] More preferred is that the reduced form of the precursor comprises a compound of formula (P-l): wherein R1, R2, R3and R4either are hydrogen, or form together with the N-containing ring a tetrahydroacridine unit, or a tetradecahydroacridine unit.

[0107] In another more preferred embodiment, the reduced form of the precursor comprises a compound of formula (P-ll): wherein R1, R2, R3and R4are hydrogen; and wherein L1and L2are, independently of each other, as defined above.

[0108] Preferably, R is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, more preferably from the group consisting of H, methyl, ethyl, propyl and isopropyl, more preferably from the group consisting of H, ethyl and propyl, wherein more preferably, R is H.

[0109] Preferably, the base provided according to (i) and comprised in the mixture ME according to (ii) is selected from the group consisting of alkali hydroxides, alkali alkoxides, alkali metal amides and a mixture of two or more thereof. Preferably, the alkali hydroxide is selected from the group consisting of NaOH, KOH, and a mixture thereof, preferably wherein the alkali hydroxide is KOH. Also preferred is the alkali alkoxide being selected from the group consisting of sodium alkoxides, potassium alkoxides, and a mixture thereof, more preferably from the group consisting of sodium ethoxide, potassium ethoxide, and a mixture thereof.

[0110] Preferably, the at least one alcohol R-CH2-CH2-OH is a bio-based alcohol, preferably obtainable or obtained from sugar-containing crops, preferably from one or more of sugar cane and corn.

[0111] Preferably, the process in accordance with the present invention further comprises

[0112] (viii) employing the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H, preferably separated according to (vii) as defined according to the present invention, as an additive to or as a substitute for naphtha. The present invention further relates to a chemical composition comprising at least one hydrocarbon R-CH2-CH2-(CHR-CH2)X-H, said chemical composition being obtainable or obtained by the process according to the present invention.

[0113] The present invention further relates to a use of the chemical composition according to the present invention as an additive to or as a substitute for naphtha.

[0114] The present invention is further illustrated by the following set of embodiments and combinations of embodiments resulting from the dependencies and back-references as indicated. In particular, it is noted that in each instance where a range of embodiments is mentioned, for example in the context of a term such as "The process of any one of embodiments 1 to 4", every embodiment in this range is meant to be explicitly disclosed for the skilled person, i.e. the wording of this term is to be understood by the skilled person as being synonymous to "The process of any one of embodiments 1 , 2, 3 and 4". Further, it is explicitly noted that the following set of embodiments represents a suitably structured part of the general description directed to preferred aspects of the present invention, and, thus, suitably supports, but does not represent the claims of the present invention.

[0115] 1 . A process for preparing at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H, the process comprising

[0116] (i) providing at least one alcohol R-CH2-CH2-OH, wherein R is selected from the group consisting of H, C1-C10 alkyl, C5-C10 aryl, and a mixture of two or more thereof, a base, at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor and a reducing agent;

[0117] (ii) preparing a liquid mixture ME comprising the at least one alcohol R-CH2-CH2-OH, the base, and the at least one of the catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor provided according to (i);

[0118] (iii) subjecting the liquid mixture ME prepared according to (ii) to alcohol conversion conditions in a reaction space SG, obtaining in said reaction space SG a liquid reaction mixture MG comprising at least one alcohol R-CH2-CH2-(CHR-CH2)X-OH, x is an integer in the range of from 1 to 10, the liquid reaction mixture MG further comprising the catalyst;

[0119] (iv) separating the at least one alcohol R-CH2-CH2-(CHR-CH2)X-OH from the liquid reaction mixture MG, obtaining the at least one alcohol R-CH2-CH2-(CHR-CH2)X-OH and a mixture Me comprising the at least one of a catalyst, precursor thereof, reduced form of the catalyst or reduced form of the precursor;

[0120] (v) preparing a liquid mixture Mi comprising the at least one alcohol R-CH2-CH2-(CHR- CH2)X-OH separated from MG according to (iv) and further comprising the reducing agent provided according to (i);

[0121] (vi) subjecting the liquid mixture Mi prepared according to (v) to alcohol reduction conditions in a reaction space SR, obtaining in said reaction space SR a liquid reaction mixture MR comprising the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)X-H; wherein the base is selected from the group consisting of ammonium hydroxide, alkali hydroxides, alkaline earth hydroxides, ammonium carbonate, ammonium hydrogen carbonate, alkali carbonates, alkali hydrogen carbonates, alkaline earth carbonates, alkaline hydrogen carbonates, alkali alkoxides, alkaline earth alkoxides, alkali metal amides, alkaline earth metal amides, secondary amino acids, and a mixture of two or more thereof; the at least one of a catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor comprises a metal selected from the group consisting of Al, Ca, Fe, Co, Ni, Cu, Ir, Mn, Os, Pd, Pt, Rh, Ru, and a mixture of two or more thereof; and the reducing agent is selected from the group consisting of a redox catalyst and a hydride compound, wherein the redox catalyst comprises a transition metal, and the hydride compound is selected from the group consisting of a silane, an alkali hydride, an alkaline earth hydride, an aluminum hydride, an alkali aluminum hydride, an alkali bo- rohydride, a hydrogen halide, and a mixture of two or more thereof. The process of embodiment 1 , wherein according to (i), a solvent is additionally provided, wherein the liquid mixture ME prepared according to (ii) additionally comprises said solvent, and wherein the mixture Me obtained according to (iv) additionally comprises said solvent. The process of embodiment 2, wherein the solvent has a boiling point of 110 °C or more, preferably a boiling point of 140 °C or more, more preferably a boiling point of 160 °C or more, more preferably a boiling point of 180 °C or more, more preferably a boiling point of 190 °C or more. The process of embodiment 2 or 3, wherein the solvent has a solubility in water at 25 °C of from 0 to 1 weight-%, preferably from 0 to 0.5 weight-%, preferably a solubility in water at 25 °C of from 0 to 0.1 weight-%, more preferably a solubility in water at 25 °C of from 0 to 0.05 weight-%, more preferably a solubility in water at 25 °C of from 0 to 0.01 weight-%, based on 100 weight-% water. The process of any one of embodiments 2 to 4, wherein the distribution coefficient of the catalyst in a system of the solvent and water is from 0 to 0.01 , preferably from 0 to 0.005, more preferably from 0 to 0.005, based on 1 kg catalyst. The process of any one of embodiments 2 to 5, wherein the solvent is a mixture of at least two aromatic hydrocarbons with a boiling point of 180 °C or more. The process of any one of embodiments 2 to 6, wherein the solvent is selected from the group consisting of biphenyl, diphenyl ether, 1-tert-butyl-3,5-dimethyl-benzene, ethylbenzene, cyclododecane, cyclononane, cyclooctane, cycloheptane, decaline, n-butylbutyrate, n-hexylhexyrate, n-octyloctyrate, texanole, di-n-butylether, di-iso-butylether, di-sec-butyl- ether, and a mixture of two or more thereof, preferably from the group consisting of biphenyl, diphenyl ether, and a mixture thereof, wherein more preferably, the solvent is a mixture of biphenyl and diphenyl ether.

[0122] 8. The process of any one of embodiments 2 to 7, wherein the solvent is a mixture of biphenyl and diphenyl ether, preferably at a molar ratio of biphenyl relative to diphenyl ether in the range of from 1 :2 to 1 :6, more preferably in the range of from 1 :2.5 to 1 :4.

[0123] 9. The process of any one of embodiments 2 to 8, wherein the solvent does not form an azeotrope with water.

[0124] 10. The process of any one of embodiments 2 to 9, wherein the solvent does not include any one of benzene, toluene, xylene or mesitylene.

[0125] 11 . The process of any one of embodiments 2 to 10, wherein at least a part of the solvent comprised in the mixture Me obtained according to (iv) is recycled to (ii).

[0126] 12. The process of any one of embodiments 1 to 11 , wherein at least a part of the at least one of a catalyst, precursor thereof, reduced form of the catalyst or reduced form of the precursor comprised in the mixture Me obtained according to (iv) is recycled to (ii) or (iii).

[0127] 13. The process of any one of embodiments 1 to 12, wherein the liquid reaction mixture MG obtained according to (iii) further comprises at least one unreacted alcohol R-CH2-CH2- OH.

[0128] 14. The process of embodiment 13, comprising separating at least a part of said unreacted alcohol R-CH2-CH2-OH from the liquid reaction mixture MG.

[0129] 15. The process of embodiment 12 or 13, wherein separating at least a part of the unreacted alcohol R-CH2-CH2-OH from MG is carried out by distillation, extraction, flashing, or by employing a membrane.

[0130] 16. The process of any one of embodiments 13 to 14, wherein at least a part of the at least one unreacted alcohol R-CH2-CH2-OH separated from MG is recycled to (ii) or (iii).

[0131] 17. The process of any one of embodiments 1 to 16, further comprising

[0132] (vii) separating the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H from the liquid reaction mixture MR. 18. The process of embodiment 17, wherein separating the at least one hydrocarbon R-CH2- CH2-(CHR-CH2)X-H according to (vii) is carried out by distillation, extraction, flushing, extractive distillation with monoethylene glycol, and employing a membrane, preferably by distillation or extraction.

[0133] 19. The process of any one of embodiments 1 to 18, wherein integer x is in the range of from 2 to 10, preferably in the range of from 2 to 8, more preferably in the range of from 2 to 6.

[0134] 20. The process of any one of embodiments 1 to 14, wherein the at least one alcohol provided according to (i) comprises ethanol and the at least one alcohol R-CH2-CH2-(CHR-CH2)x- OH separated according to (iv) and comprised in Mi comprises H-CH2-CH2-(CHR-CH2)X- OH.

[0135] 21. The process of embodiment 20, wherein for H-CH2-CH2-(CHR-CH2)X-OH, integer x is in the range of from 2 to 10, preferably in the range of from 2 to 8, more preferably in the range of from 2 to 6.

[0136] 22. The process of any one of embodiments 19 to 21 , wherein the liquid mixture MR obtained according to (vi) comprises at least one hydrocarbon H-CH2-CH2-(CHR-CH2)X-H, wherein x is an integer in the range of from 2 to 10, preferably in the range of from 2 to 8, more preferably in the range of from 2 to 6.

[0137] 23. The process of any one of embodiments 1 to 22, wherein from 90 to 100 weight-%, preferably wherein from 95 to 100 weight-%, more preferably from 98 to 100 weight-%, more preferably 99 to 100 weight-% of the liquid mixture ME prepared according to (ii) consist of the at least one alcohol R-CH2-CH2-OH, the base, the at least one of a catalyst, the precursor thereof, or the reduced form of the catalyst or the precursor and optionally the solvent as defined in any one of embodiments 2 to 8.

[0138] 24. The process of any one of embodiments 1 to 22, wherein preparing a liquid mixture ME in step (ii) comprises at least one alcohol R-CH2-CH2-OH, a base, and the at least one of a catalyst, or precursor thereof provided according to (i) and optionally the solvent as defined in any one of embodiments 2 to 8.

[0139] 25. The process of any one of embodiments 1 to 24, wherein the process is a continuous process.

[0140] 26. The process of any one of embodiments 1 to 24, wherein the process is a semi-batch process or a batch process.

[0141] 27. The process of any one of embodiments 1 to 26, wherein the alcohol conversion conditions according to (iii) comprise the presence of at least one inert gas in the reaction space SG, wherein the at least one inert gas is preferably selected from the group consisting of nitrogen, argon, and a mixture thereof.

[0142] 28. The process of any one of embodiments 1 to 27, wherein the alcohol conversion conditions according to (iii) comprise a pressure in the reaction space SG in the range of from 1 x 105to 3.5 x 106Pa, preferably in the range of from 1 x 105to 3.1 x 106Pa, more preferably in the range of from 1 x 105to 2 x 106Pa, more preferably in the range from 1 x 105to 1.5 x 106Pa.

[0143] 29. The process of any one of embodiments 1 to 38, wherein the alcohol conversion conditions according to (iii) comprise a temperature of the reaction mixture MG in the reaction space SG in the range of from 100 to 200 °C, preferably in the range of from 120 to 180 ° C, more preferably in the range of from 130 to 160 °C.

[0144] 30. The process of any one of embodiments 1 to 29, wherein the alcohol conversion conditions according to (iii) comprise an amount of the base in the reaction mixture MG in the reaction space SG in the range of from 0.1 to 10 weight -%, preferably in the range of from 0.5 to 8 weight-%, more preferably in the range of from 1 to 5 weight-%, based on the total weight of the mixture MG.

[0145] 31 . The process of any one of embodiments 1 to 29, wherein the alcohol conversion conditions according to (iii) comprise an amount of the catalyst in the reaction mixture MG in the reaction space SG in the range of from 0.001 to 2 weight-%, preferably in the range of from 0.001 to 1 weight-%, more preferably in the range of from 0.001 to 0.5 weight-%, based on the total weight of the mixture MG.

[0146] 32. The process of any one of embodiments 1 to 31 , wherein the reducing agent provided according to (i) and comprised in the liquid mixture Mi according to (v) comprises a redox catalyst, wherein the redox catalyst comprises a transition metal selected from the group consisting of Pd, Rh, Ni, Ru, Pt, Re, Co, Ir, and a mixture of two or more thereof.

[0147] 33. The process of embodiment 32, wherein the redox catalyst further comprises a support material, wherein preferably the support material is selected from the group consisting of a heteropolyacid, a sulfonic acid resin, carbon, a metal oxide, a metalloid oxide, and a mixture of two or more thereof.

[0148] 34. The process of embodiment 32 or 33, wherein the alcohol reduction conditions according to (vi) comprise the presence of at least one inert gas and H2 in the reaction space SR, wherein the at least one inert gas is preferably selected from the group consisting of nitrogen, argon, and a mixture thereof. 35. The process of any one of embodiments 32 to 43, wherein the alcohol reduction conditions according to (vi) comprise a temperature of the reaction mixture MR in the reaction space SR in the range of from 100 to 250 °C.

[0149] 36. The process of any one of embodiments 32 to 34, wherein the alcohol reduction conditions according to (vi) comprise a pressure in a reaction space SR in the range of from 1 x 105to 1 x 107Pa.

[0150] 37. The process of any one of embodiments 1 to 31 , wherein the reducing agent provided according to (i) and comprised in the liquid mixture Mi according to (v) comprises a hydride compound, wherein the hydride compound is selected from the group consisting of / 7-bu- tylsilane, diethylsilane, diisobutylaluminum hydride, lithium triethoxyaluminohydride, NaH, LiH, CaH2, LiAIFU, NaBH4, Hl / acetic acid, mixed hydrides of AlCh and LiAIFU, HSiEts comprising B(C6Fs)3, and a mixture of two or more thereof, more preferably selected from the group consisting of / 7-butylsilane, diethylsilane, Hl / acetic acid, mixed hydrides of AICI3 and UAIH4, HSiEts comprising B(C6Fs)3, and a mixture of two or more thereof.

[0151] 38. The process of embodiment 37, wherein the alcohol reduction conditions according to (vi) comprise the presence of at least one inert gas in the reaction space SR, wherein the at least one inert gas is preferably selected from the group consisting of nitrogen, argon, and a mixture thereof.

[0152] 39. The process of any one of embodiments 1 to 38, wherein the at least one of the catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor provided according to (i) and comprised in the mixture ME comprises a metal selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, Ru, and a mixture of two or more thereof.

[0153] 40. The process of any one of embodiments 1 to 39, wherein the at least one of the catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor provided according to (i) and comprised in the mixture ME is a homogenous catalyst.

[0154] 41 . The process of any one of embodiments 1 to 40, preferably of embodiment 37 or 38, wherein the at least one of the catalyst provided according to (i) and comprised in the mixture ME comprises a compound of formula (A) wherein M is selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, and Ru;

[0155] L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, S(=O)Ra, heteroaryl containing at least one heteroatom selected from nitrogen and sulfur, AsRaRb, SbRaRb, and a N-heterocyclic carbene represented by the structures:

[0156] L3is selected from the group consisting of CO, PRaRbRc, AsRaRbRc, SbRaRbRc, SRaRb, RdCN, RdNC, RdCN, N2, PF3, pyridine, and thiophene;

[0157] R1, R2, R3and R4either are hydrogen, or form together with the pyridyl unit of the catalyst of formula (A) an acridinyl unit, or R1and R2or R3and R4form together with the pyridyl unit of the catalyst of formula (A) a quinolinyl unit; n is 0 or 1 ;

[0158] Y is selected from the group consisting of H, F, Cl, Br, I, OC(=O)CF3, OSO2CF3, CN, CO, OH, OR, NRd2, NH3, NRd3, and Rd2NSO2Rd;

[0159] Ra, Rb, Rc, Rd, R5, R6and R7are, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cio-alkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Ci-Cio-cycloalkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -het- erocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -aryl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; and unsubstituted or substituted Cs-C -heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2 and Ci-Cio-alkyl; and

[0160] X is selected from the group consisting of one, two, three, four, five, six, and seven substituents positioned at any carbon atom on the acridinyl unit, or one, two, three, four and five substituents positioned at any carbon atom on the quinolinyl unit, or one substituent positioned at the carbon atom on the pyridyl unit, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl, preferably X is selected from the group consisting of H, Cl, Br, OH, CN, and C1-C5 alkyl; and wherein the precursor of the catalyst comprising a compound of formula (A) comprises a mixture comprising a compound comprising a metal M and at least one component selected from the group consisting of CO, PRaRbRc, SRaRb, RaCN, RaNC, N2, PF3, organic carbonyl compounds, Ci-Cio-alkyl, Ci-Ci2-cycloalkyl, C2-Ci2-alkenyl, Cs-Cis-cycloalkenyl, C5-C20- aryl, CN, CO, OH, OC(=O)CF3, OSO2CF3, hydrides, pyridines, halogenides, hydroxides, and thiophenes; and a compound of formula (H)

[0161] M is selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, and Ru;

[0162] L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, S(=O)Ra, heteroaryl containing at least one heteroatom selected from nitrogen and sulfur, AsRaRb, SbRaRb, and a N-heterocyclic carbene represented by the structures:

[0163] R1, R2, R3and R4either are hydrogen, or form together with the pyridyl unit of the catalyst of formula (A) an acridinyl unit, or R1and R2or R3and R4form together with the pyridyl unit of the catalyst of formula (A) a quinolinyl unit; n is 0 or 1 ;

[0164] Ra, Rb, Rc, Rd, R5, R6and R7are, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cio-alkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Ci-Cio-cycloalkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -het- erocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -aryl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; and unsubstituted or substituted Cs-C -heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2 and Ci-Cio-alkyl;

[0165] X is selected from the group consisting of one, two, three, four, five, six, and seven substituents positioned at any carbon atom on the acridinyl unit, or one, two, three, four and five substituents positioned at any carbon atom on the quinolinyl unit, or one substituent positioned at the carbon atom on the pyridyl unit, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl, preferably X is selected from the group consisting of H, Cl, Br, OH, CN, and C1-C5 alkyl.

[0166] 42. The process of any one of embodiments 1 to 41 , wherein preparing a liquid mixture ME in step (ii) comprises at least one alcohol R-CH2-CH2-OH, a base, and the at least one of a catalyst, or precursor thereof provided according to (i). The process of any one of embodiments 1 to 42, wherein in formula (A) n is 0 if R1, R2, R3and R4are hydrogen. The process of any one of embodiments 1 to 42, wherein the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound of formula (B) wherein

[0167] M is selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, and Ru;

[0168] L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, and S(=O)Ra;

[0169] L3is selected from the group consisting of CO, PRaRbRc, SRaRb, RaCN, RaNC, N2, PF3, pyridine, and thiophene;

[0170] R1, R2, R3and R4either are hydrogen, or form together with the pyridyl unit of the catalyst of formula (A) an acridinyl unit; n is 0 or 1 , and if R1, R2, R3and R4are hydrogen, n is 0;

[0171] Ra, Rb, Rcand Rdare, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cio-alkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Ci-Cio-cycloalkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; Cs-C -heterocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S; Cs-C -aryl; and Cs-C -heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S;

[0172] Y is selected from the group consisting of H, F, Cl, Br, I, OC(=O)CF3, OSO2CF3, CN, CO, and OH. The process of any one of embodiments 1 to 42, wherein the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound of formula (C) wherein

[0173] M is selected from the group consisting of Ir, Ru, and Mn; L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, and S(=O)Ra;

[0174] L3is selected from the group consisting of CO, PRaRbRc, SRaRb, RaCN, RaNC, N2, PF3, pyridine, and thiophene;

[0175] Ra, Rb, Rcand Rdare, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cw-alkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cw-alkyl; unsubstituted or substituted Ci-C -cycloalkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cw-alkyl; Cs-Cw-heterocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S; Cs-C -aryl; and Cs-Cw-heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S;

[0176] Y is selected from the group consisting of H, F, Cl, Br, I, OC(=O)CF3, OSO2CF3, CN, CO, and OH. The process of any one of embodiments 1 to 42, wherein the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound of formula (D) wherein

[0177] M is selected from the group consisting of Ir, Ru, and Mn;

[0178] L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, and S(=O)Ra;

[0179] L3is selected from the group consisting of CO, PRaRbRc, SRaRb, RaCN, RaNC, N2, PF3, pyridine, and thiophene;

[0180] Ra, Rb, Rcand Rdare, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cw-alkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cw-alkyl; unsubstituted or substituted Ci-Cio-cycloalkyl wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cw-alkyl; Cs-Cw-heterocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S; Cs-Cw-aryl; and Cs-Cw-heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S;

[0181] Y is selected from the group consisting of H, F, Cl, Br, I, OC(=O)CF3, OSO2CF3, CN, CO, and OH. The process of any one of embodiments 1 to 46, wherein M is selected from the group consisting of Ir and Ru, preferably wherein M is Ru. The process of any one of embodiments 1 to 46, wherein M is Ru, and wherein the alcohol conversion conditions according to (iii) comprise a temperature of the reaction mixture MG in the range of from 100 to 170 °C, preferably in the range of from 120 to 170 °C, more preferably in the range of from 120 to 160 °C, more preferably in the range of from 130 to 150 °C.

[0182] 49. The process of any one of embodiments 1 to 48, wherein L3is CO.

[0183] 50. The process of any one of embodiments 1 to 49, wherein L1and L2are each (PRaRb), and wherein Raand Rbare Ci-G -alkyl, preferably wherein Raand Rbare each isopropyl or tert-butyl.

[0184] 51 . The process of any one of embodiments 1 to 49, wherein L1and L2are each (PRaRb), and wherein Raand Rbare Ci-Cio-cycloalkyl, preferably wherein Raand Rbare each cyclohexyl.

[0185] 52. The process of any one of embodiments 1 to 49, wherein L1and L2are each (PRaRb), and wherein Raand Rbare Cs-C -aryl.

[0186] 53. The process of any one of embodiments 1 to 52, wherein Y is selected from the group consisting of F, Cl, Br, and I, preferably wherein Y is selected from the group consisting of Cl or Br, more preferably wherein Y is Cl.

[0187] 54. The process of any one of embodiments 1 to 52, wherein Y is CO.

[0188] 55. The process of any one of embodiments 1 to 43, wherein the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound of formula (E) wherein Cy is cyclohexyl.

[0189] 56. The process of any one of embodiments 1 to 43, wherein the reduced form of the catalyst comprises a compound of formula (E’) wherein Cy is cyclohexyl.

[0190] 57. The process of any one of embodiments 1 to 43, wherein the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound of formula (F) wherein iPr is isopropyl.

[0191] 58. The process of any one of embodiments 1 to 43, wherein the reduced form of the catalyst comprises a compound of formula (F’) wherein iPr is isopropyl.

[0192] 59. The process of any one of embodiments 1 to 43, wherein the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound of formula wherein tBu is tert-butyl.

[0193] 60. The process of any one of embodiments 1 to 43, wherein the reduced form of the catalyst comprises a compound of formula (G’) wherein tBu is tert-butyl.

[0194] 61 . The process of any one of embodiments 1 to 43, wherein the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound comprising a metal M selected from the group consisting of I rCh x H2O, [lr(COD)CI]2, [lr(COE)2CI]2, [lr(C2H4)2CI]2, [lr(COD)OH]2, [lr(COD)MeO]2, [lrCp*CI2], [IrCp Cl2], lr4(CO)i2, [lr(PPh3)2(CO)CI], [lr(acetylacetonate)3], and [lr(acety- lacetonate)(COD)], wherein Cp is cyclopentadienyl, Cp* is pentamethylcyclopentadienyl, COD is 1 ,5-cyclooctadienyl, COE is cyclooctenyl, and methylallyl is 2-methylallyL

[0195] 62. The process of any one of embodiments 1 to 43, wherein the at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor comprises a compound comprising a metal M selected from the group consisting of [Ru(p-cy- mene)CI2]2, [Ru(benzene)CI2]y, [Ru(CO)2CI2]y, where y is in each case in the range from 1 to 1000, [RU(CO)3CI2]2, [Ru(COD)(allyl)], RuCh x H2O, [Ru(acetylacetonate)3], [Ru(DMSO)4CI2], [Ru(cyclopentadienyl)(CO)2CI], [Ru(cyclopentadienyl)(CO)2H], [Ru(cyclo- pentadienyl)(CO)2]2, [Ru(Cp)(CO)2CI], [Ru(Cp*)(CO)2H], [Ru(Cp*)(CO)2]2, [Ru(in- denyl)(CO)2CI], [Ru(indenyl)(CO)2H], [Ru(indenyl)(CO)2]2, ruthenocene, [Ru(COD)CI2]2, [Ru(Cp*)(COD)CI], [RU3(CO)I2], [Ru(PPh3)4(H)2], [Ru(PPh3)3(CI)2], [Ru(PPh3)3(CO)(CI)2], [Ru(PPh3)3(CO)(CI)(H)], [Ru(PPh3)3(CO)(H)2], and [Ru(cyclooctadienyl)(methylallyl)2], wherein Cp is cyclopentadienyl, Cp* is pentamethylcyclopentadienyl, COD is 1 ,5-cyclooc- tadienyl, and methylallyl is 2-methylallyL

[0196] 63. The process of any one of embodiments 1 to 62, wherein the reduced form of the precursor comprises a compound of formula (P-l) or (P-ll): wherein R1, R2, R3and R4either are hydrogen, or form together with the N-containing ring a tetrahydroquinoline unit, a decahydroquinoline unit, a tetrahydroacridine unit, or a tetradecahydroacridine unit; and wherein L1and L2are, independently of each other, as defined above; wherein R1, R2, R3and R4are hydrogen; and wherein L1and L2are, independently of each other, as defined above.

[0197] 64. The process of any one of embodiments 1 to 63, wherein the reduced form of the precursor comprises a compound of formula (P-l): wherein R1, R2, R3and R4either are hydrogen, or form together with the N-containing ring a tetrahydroacridine unit, or a tetradecahydroacridine unit.

[0198] 65. The process of any one of embodiments 1 to 63, wherein the reduced form of the precursor comprises a compound of formula (P-l I): wherein R1, R2, R3and R4are hydrogen; and wherein L1and L2are, independently of each other, as defined above.

[0199] 66. The process of any one of embodiments 1 to 65, wherein R is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, preferably from the group consisting of H, methyl, ethyl, propyl and isopropyl, more preferably from the group consisting of H, ethyl and propyl, wherein more preferably, R is H.

[0200] 67. The process of any one of embodiments 1 to 66, wherein the base provided according to (i) and comprised in the mixture ME according to (ii) is selected from the group consisting of alkali hydroxides, alkali alkoxides, alkali metal amides and a mixture of two or more thereof. 68. The process of embodiment 67, wherein the alkali hydroxide is selected from the group consisting of NaOH, KOH, and a mixture thereof, preferably wherein the alkali hydroxide is KOH.

[0201] 69. The process of embodiment 67, wherein the alkali alkoxide is selected from the group consisting of sodium alkoxides, potassium alkoxides, and a mixture thereof, preferably from the group consisting of sodium ethoxide, potassium ethoxide, and a mixture thereof.

[0202] 70. The process of any one of embodiments 1 to 69, wherein the at least one alcohol R-CH2- CH2-OH is a bio-based alcohol, preferably obtainable or obtained from sugar-containing crops, preferably from one or more of sugar cane and corn.

[0203] 71 . The process of any one of embodiments 1 or 70, further comprising

[0204] (viii) employing the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H, preferably separated according to (vii) as defined in embodiment 15 or 16, as an additive to or as a substitute for naphtha.

[0205] 72. A chemical composition comprising at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H, said chemical composition being obtainable or obtained by the process according to any one of embodiments 1 to 70.

[0206] 73. Use of the chemical composition according to embodiment 72 as an additive to or as a substitute for naphtha.

[0207] 74. The use of embodiment 73, insofar as embodiment 72 is dependent on embodiment 70, as an additive to naphtha or bionaphtha or as a substitute for bionaphtha.

[0208] The determination of the distribution coefficient of the solvent in water comprises the following steps:

[0209] 1 . combining the two components, e.g. feed and solvent, in a predefined solvent ratio;

[0210] 2. turbulent mixing of the combined components over a longer period of time (> 10 min) at a defined extraction temperature;

[0211] 3. allowing for phase separation;

[0212] 4. taking samples of each phase at the extraction temperature;

[0213] 5. centrifuging the samples and withdrawing clear samples at the extraction temperature;

[0214] 6. analyzing the samples;

[0215] 7. comparing the results of extract- and raffinate - calculation of the the partition equilibrium / par- tition coefficient at the selected temperature.

[0216] Cited literature:

[0217] M. Guerbet, C. R. Hebd. Seances Acad. Sci. 1899, 128, p. 511-513

[0218] - US 2021 / 154110 A1 N.Antil et aL, “Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols”, Inorganic Chemistry, vol. 60, no. 12, 2021-06-04, pages 9029 to 9039

[0219] - X.J. Dai et aL, “En Route to a Practical Primary Alcohol Deoxygenation”, Journal of the American Society, vol. 138, no. 16, 2016-04-18, pages 5433 to 5440

[0220] - WO 2014 / 159484 A1

[0221] - US 2015 / 246863 A1

[0222] - Y.Xie et aL, “Highly efficient Process for Production of Biofuel from ethanol Catalyzed by Ruthenium Pincer Complexes”, Journal of the American Society, vol. 138, no. 29, 2016- 07-18, pages 9077 to 9080

[0223] - WO 2013 / 156399 A1

Claims

Claims1 . A process for preparing at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H, the process comprising(i) providing at least one alcohol R-CH2-CH2-OH, wherein R is selected from the group consisting of H, C1-C10 alkyl, C5-C10 aryl, and a mixture of two or more thereof, a base, at least one of a catalyst, a precursor thereof, a reduced form of the catalyst, or a reduced form of the precursor and a reducing agent;(ii) preparing a liquid mixture ME comprising the at least one alcohol R-CH2-CH2-OH, the base, and the at least one of the catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor provided according to (i);(iii) subjecting the liquid mixture ME prepared according to (ii) to alcohol conversion conditions in a reaction space SG, obtaining in said reaction space SG a liquid reaction mixture MG comprising at least one alcohol R-CH2-CH2-(CHR-CH2)x-OH, x is an integer in the range of from 1 to 10, the liquid reaction mixture MG further comprising the catalyst;(iv) separating the at least one alcohol R-CH2-CH2-(CHR-CH2)X-OH from the liquid reaction mixture MG, obtaining the at least one alcohol R-CH2-CH2-(CHR-CH2)X-OH and a mixture Me comprising the at least one of a catalyst, precursor thereof, reduced form of the catalyst or reduced form of the precursor;(v) preparing a liquid mixture Mi comprising the at least one alcohol R-CH2-CH2-(CHR- CH2)X-OH separated from MG according to (iv) and further comprising the reducing agent provided according to (i);(vi) subjecting the liquid mixture Mi prepared according to (v) to alcohol reduction conditions in a reaction space SR, obtaining in said reaction space SR a liquid reaction mixture MR comprising the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)X-H; wherein the base is selected from the group consisting of ammonium hydroxide, alkali hydroxides, alkaline earth hydroxides, ammonium carbonate, ammonium hydrogen carbonate, alkali carbonates, alkali hydrogen carbonates, alkaline earth carbonates, alkaline hydrogen carbonates, alkali alkoxides, alkaline earth alkoxides, alkali metal amides, alkaline earth metal amides, secondary amino acids, and a mixture of two or more thereof; the at least one of a catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor comprises a metal selected from the group consisting of Al, Ca, Fe, Co, Ni, Cu, Ir, Mn, Os, Pd, Pt, Rh, Ru, and a mixture of two or more thereof; and the reducing agent is selected from the group consisting of a redox catalyst and a hydride compound, wherein the redox catalyst comprises a transition metal, and the hydride compound is selected from the group consisting of a silane, an alkali hydride, an alkaline earth hydride, an aluminum hydride, an alkali aluminum hydride, an alkali bo- rohydride, a hydrogen halide, and a mixture of two or more thereof.

2. The process of claim 1 , wherein according to (i), a solvent is additionally provided, wherein the liquid mixture ME prepared according to (ii) additionally comprises said solvent, and wherein the mixture Me obtained according to (iv) additionally comprises said solvent.

3. The process of claim 2, wherein the solvent is selected from the group consisting of biphenyl, diphenyl ether, 1-tert-butyl-3,5-dimethyl-benzene, ethylbenzene, cyclododecane, cyclononane, cyclooctane, cycloheptane, decaline, n-butylbutyrate, n-hexylhexyrate, n- octyloctyrate, texanole, di-n-butylether, di-iso-butylether, di-sec-butylether, and a mixture of two or more thereof, preferably from the group consisting of biphenyl, diphenyl ether, and a mixture thereof, wherein more preferably, the solvent is a mixture of biphenyl and diphenyl ether.

4. The process of any one of claims 1 to 3, wherein at least a part of the at least one of a catalyst, precursor thereof, reduced form of the catalyst or reduced form of the precursor comprised in the mixture Me obtained according to (iv) is recycled to (ii) or (iii).

5. The process of any one of claims 1 to 4, further comprising(vii) separating the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H from the liquid reaction mixture MR.

6. The process of claim 5, wherein separating the at least one hydrocarbon R-CH2-CH2- (CHR-CH2)X-H according to (vii) is carried out by distillation, extraction, flushing, extractive distillation with monoethylene glycol, and employing a membrane, preferably by distillation or extraction.

7. The process of any one of claims 1 to 6, wherein the liquid mixture MR obtained according to (vi) comprises at least one hydrocarbon H-CH2-CH2-(CHR-CH2)X-H, wherein x is an integer in the range of from 2 to 10, preferably in the range of from 2 to 8, more preferably in the range of from 2 to 6.

8. The process of any one of claims 1 to 7, wherein the reducing agent provided according to (i) and comprised in the liquid mixture Mi according to (v) comprises a redox catalyst, wherein the redox catalyst comprises a transition metal selected from the group consisting of Pd, Rh, Ni, Ru, Pt, Re, Co, Ir, and a mixture of two or more thereof.

9. The process of claim 8, wherein the redox catalyst further comprises a support material, wherein preferably the support material is selected from the group consisting of a heteropolyacid, a sulfonic acid resin, carbon, a metal oxide, a metalloid oxide, and a mixture of two or more thereof.

10. The process of claim 8 or 9, wherein the alcohol reduction conditions according to (vi) comprise the presence of at least one inert gas and H2 in the reaction space SR, wherein the at least one inert gas is preferably selected from the group consisting of nitrogen, argon, and a mixture thereof.11 . The process of any one of claims 8 to 10, wherein the alcohol reduction conditions according to (vi) comprise a temperature of the reaction mixture MR in the reaction space SR in the range of from 100 to 250 °C.

12. The process of any one of claims 8 to 11 , wherein the alcohol reduction conditions according to (vi) comprise a pressure in a reaction space SR in the range of from 1 x 105to 1 x 107Pa.

13. The process of any one of claims 1 to 12, wherein the at least one of the catalyst, the precursor thereof, the reduced form of the catalyst, or the reduced form of the precursor provided according to (i) and comprised in the mixture ME comprises a metal selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, Ru, and a mixture of two or more thereof.

14. The process of any one of claims 1 to 13, preferably of claim 13, wherein the at least one of the catalyst provided according to (i) and comprised in the mixture ME comprises a compound of formula (A)M is selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, and Ru;L1and L2, are, independently of each other, PRaRb, NRaRb, SRa, SH, S(=O)Ra, heteroaryl containing at least one heteroatom selected from nitrogen and sulfur, AsRaRb, SbRaRb, and a N-heterocyclic carbene represented by the structures:L3is selected from the group consisting of CO, PRaRbRc, AsRaRbRc, SbRaRbRc, SRaRb, RdCN, RdCN, N2, PF3, pyridine, and thiophene;R1, R2, R3and R4either are hydrogen, or form together with the pyridyl unit of the catalyst of formula (A) an acridinyl unit, or R1and R2or R3and R4form together with the pyridyl unit of the catalyst of formula (A) a quinolinyl unit;n is 0 or 1 ;Y is selected from the group consisting of H, F, Cl, Br, I, OC(=O)CF3, OSO2CF3, CN, CO, OH, OR, NRd2, NH3, NRd3, and Rd2NSO2Rd;Ra, Rb, Rc, Rd, R5, R6and R7are, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cio-alkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Ci-Cio-cycloalkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -het- erocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -aryl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; and unsubstituted or substituted Cs-C -heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2 and Ci-Cio-alkyl; andX is selected from the group consisting of one, two, three, four, five, six, and seven substituents positioned at any carbon atom on the acridinyl unit, or one, two, three, four and five substituents positioned at any carbon atom on the quinolinyl unit, or one substituent positioned at the carbon atom on the pyridyl unit, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl, preferably X is selected from the group consisting of H, Cl, Br, OH, CN, and C1-C5 alkyl; and wherein the precursor of the catalyst comprising a compound of formula (A) comprises a mixture comprising a compound comprising a metal M and at least one component selected from the group consisting of CO, PRaRbRc, SRaRb, RaCN, RaNC, N2, PF3, organic carbonyl compounds, Ci-Cio-alkyl, Ci-Ci2-cycloalkyl, C2-Ci2-alkenyl, Cs-Cis-cycloalkenyl, C5-C20- aryl, CN, CO, OH, OC(=O)CF3, OSO2CF3, hydrides, pyridines, halogenides, hydroxides, and thiophenes; and a compound of formula (H)M is selected from the group consisting of Ir, Mn, Os, Pd, Pt, Rh, and Ru;L1and L2are, independently of each other, PRaRb, NRaRb, SRa, SH, S(=O)Ra, heteroaryl containing at least one heteroatom selected from nitrogen and sulfur, AsRaRb, SbRaRb, and a N-heterocyclic carbene represented by the structures:R1, R2, R3and R4either are hydrogen, or form together with the pyridyl unit of the catalyst of formula (A) an acridinyl unit, or R1and R2or R3and R4form together with the pyridyl unit of the catalyst of formula (A) a quinolinyl unit; n is 0 or 1 ;Ra, Rb, Rc, Rd, R5, R6and R7are, independently of each other, selected from the group consisting of H, unsubstituted or substituted Ci-Cio-alkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Ci-Cio-cycloalkyl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -het- erocyclyl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; unsubstituted or substituted Cs-C -aryl, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl; and unsubstituted or substituted Cs-C -heteroaryl comprising at least one heteroatom selected from the group consisting of N, O, and S, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2 and Ci-Cio-alkyl;X is selected from the group consisting of one, two, three, four, five, six, and seven substituents positioned at any carbon atom on the acridinyl unit, or one, two, three, four and five substituents positioned at any carbon atom on the quinolinyl unit, or one substituent positioned at the carbon atom on the pyridyl unit, wherein the substituents are selected from the group consisting of F, Cl, Br, OH, CN, NH2, and Ci-Cio-alkyl, preferably X is selected from the group consisting of H, Cl, Br, OH, CN, and C1-C5 alkyl.

15. The process of any one of claims 1 or 14, further comprising(viii) employing the at least one hydrocarbon R-CH2-CH2-(CHR-CH2)x-H, preferably separated according to (vii) as defined in claim 5 or 6, as an additive to or as a substitute for naphtha.

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