Method for the synthesis of acridine based phosphine ligands

Abstract

The present invention relates to a process for preparing an acridine based phosphine ligand of formula (I) ccomprising adding a mixture (M1) comprising 4,5-Bis-bromomethylacridine as component (II) and at least one solvent (S1) to a mixture (M2) comprising a phosphine building block as component (III) to obtain a mixture (M3) comprising a salt (I)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4 and subjecting mixture (M3) to conditions suitable to deprotonate the salt (I)*2HBr. Furthermore, the present invention relates to the use of the acridine based phosphine ligand of the general formula (I) obtained or obtainable according to the process according to the present invention for the preparation of a metal complex catalyst.

Description

Method for the Synthesis of Acridine Based Phosphine ligandsThe present invention relates to a process for preparing an acridine based phosphine ligand of formula (I) ccompris- ing adding a mixture (M1) comprising 4,5-Bis-bromomethylacridine as component (II) and at least one solvent (S1) to a mixture (M2) comprising a phosphine building block as component (III) to obtain a mixture (M3) comprising a salt (l)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4 and subjecting mixture (M3) to conditions suitable to deprotonate the salt (l)*2HBr. Furthermore, the present invention relates to the use of the acridine based phosphine ligand of the general formula (I) obtained or obtainable according to the process according to the present invention for the preparation of a metal complex catalyst.Acridine based phosphine ligands of the general formula (I)can be used as ligands for the synthesis of metal complexes to act as highly active catalyst in attractive transformations as the selective amination of primary alcohols with ammonia to primary amines as described in Angew. Chem. Int. ed. 2008, 47, 8661-8664 and J. Am. Chem. Soc. 2014, 136, 5923-5929 or the Guerbet reaction of ethanol to 1 -butanol as described in J. Am. Chem. Soc. 2016, 138, 9077-9080. Therefore, an efficient access to the ligands of the general formula (I) in a high purity is desired.Angew. Chem. Int. Ed. 2008, 47, 8661-8664 and WO2010 / 018570 disclose the synthesis of the ligand (la)with iso-Propyl-substituents on the phosphine groups by mixing 4,5-Bis-bromomethylacridine with a no further specified purity with 2.6 equivalents of di-isopropylphosphine (Illa)in methanol followed by releasing the free ligand from the intermediate formed hydrobromide salt by adding a large excess (four equivalents) of triethylamine as the base, followed by extracting the product from the sticky residue four times with a large excess of diethyl ether to obtain the final product in 88% yield in a not further specified purity after recrystallization from pentane / acetone. A drawback of this method is the use of a 0.6 eq. excess of the expensive phosphine building (Illa), the use of large amounts of highly flammable diethylether to extract the product and a not further specified purity of the product. Another drawback is, that the methodology was only disclosed the suitability to provide ligand (la) with iso-propyl substituent at the phosphine atoms in good yields but no further variants of ligand (I). For an efficient synthesis, it would be desirable to use less of the expensive phosphine building block (III), provide other variants of ligand (I) and obtain the product in a high and specified purity.W02020 / 141520 discloses the synthesis of (la) in the same scale (5.5 mmol 4,5-Bis-bromomethylacridine as starting material) in a similar fashion than WO2010 / 018570 by mixing 4,5-Bis-bromomethylacridine with a no further specified purity with 2.6 equivalents of di-isopropylphosphine (Illa) in methanol followed by releasing the free ligand from the intermediate formed hydrobromide salt by adding a large excess (four equivalents) of triethylamine as the base, followed by extracting the product from the sticky residue now only two times with diethyl ether to obtain the final product in now only 50% yield in a not further specified purity after recrystallization from pentane / acetone. A drawback of this method is still the use of a 0.6 Eq. excess of the expensive phosphine building (Illa), the significant lower yield when reducing the amount of used highly flammable diethyl ether in the extraction and a not further specified purity of the product. Another drawback is, that the methodology was only disclosed the suitability to provide ligand (la) with isopropyl substituent at the phosphine atoms in good yields but no further variants of ligand (I). This shows that even with small variations on the previous given example, the yield of the product can drop significantly.WO2012 / 119929 discloses the synthesis of (lb)with cyclohexyl substituents on the phosphor atoms on a 14.2 mmol scale 4,5-bis-bromomethylacridine as starting material in a similar fashion than WO2010 / 018570 by mixing 4,5-bis-bromomethylacridine with a no further specified purity with 2.6 equivalents of di-cyclohexylphosphine (lllb)in methanol followed by releasing the free ligand from the intermediate formed hydrobromide salt by adding a large excess (four equivalents) of triethylamine as the base, followed by extracting the product from the sticky residue three times with the less flammable methyl-tert-butyl-ether obtain the final product in now only 33% yield in a not further specified purity. A drawback of this method is still the use of a 0.6 Eq. excess of the expensive phosphine building (I I lb), the significant lower yield when changing the phosphine building block and the ether used in the extraction and a not further specified purity of the product. Another drawback is, that it shows that the methodology providing la in a high yield cannot easily be adapted to obtain the derivate (lb) in a high yield and purity.The object of the present invention, therefore, was to provide a method for the synthesis of ligands according to formula (I) in a good yield and a high, specified purity that preferably does not feature the drawbacks of the currently known methods.This object has been achieved by a process for preparing an acridine based phosphine ligands of the general formula (I),comprising(I) providing a mixture (M1) comprising 4,5-bis-bromomethylacridine (II) and at least one solvent (S1 )(ii) providing a mixture (M2) comprising a phosphine building block (III)(Hi);(iii) adding mixture (M1) to mixture (M2) to obtain a mixture (M3) comprising a salt (l)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4(l)*2HBr(iv) subjecting mixture (M3) to conditions suitable to deprotonate the salt (l)*2HBr; whereinR1and R2are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1and R2can also be connected forming rings as cyclic aliphatic or aromatic rings.The process according to the present invention comprises steps (I), (ii), (iii), and (iv) but may also comprise further steps, such as for example separation steps or purification steps.According to step (I), a mixture (M1) comprising 4,5-Bis-bromomethylacridine (II) and at least one solvent (S1 ) is provided. Suitable solvents are in principle known to the person skilled in the art. Suitable solvents are solvents which dissolve the acridine but are not reacting with one of the building blocks under the chosen reaction conditions. Mixture (M1) may also comprise two or more solvents.According to step (ii), mixture (M2) comprising a phosphine building block (III) is provided. Mixture (M2) may also comprise further components, for example one or more solvents.Mixture (M1) is added to mixture (M2) to obtain a mixture (M3) comprising a salt (l)*2HBr, according to step (iii). According to the present invention, the mixtures (M1) and (M2) are used in an amount that the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4. It has been found that this ration results in high purity of the products obtained.The molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4According to step (iv), the resulting mixture (M3) obtained in step (iii) is subjected to conditions suitable to deprotonate the salt (l)*2HBr. Suitable conditions are in principle known to the person skilled in the art and may include treatment with a base. Preferably, the conditions comprise the treatment with an alcoholate or a hydroxide. Suitable are in particular lithium, sodium or potassium alcoholates and hydroxides.According to a further embodiment, the present invention is also directed to a process as disclosed above, wherein in step (iv), component MOR3is used wherein M is selected from Li, Na or K, and R3 is selected from H and a residue containing hydrocarbon, wherein the residue containing hydrocarbon is selected from the group consisting of C1 -010-alkyl, 03-010-cycloalkyl, 03-010-heterocyclyl comprising at least one heteroatom selected from N, 0 and S, C5-C14-aryl, C5-C10-heteroaryl comprising at least one heteroatom selected from N, 0 and S, wherein said 01-010- alkyl 03-010-cycloalkyl, 03-010-heterocyclyl, 05-014-aryl, resp. C5-C10-heteroaryl optionally has one or more further substituents selected from the group consisting of: F, Cl, Br and 01 -010-alkyl.According to a preferred embodiment, the present invention is directed to a method for the synthesis of acridine based phosphine ligands of the general formula (I) comprises the steps of using 4, 5-bis-bromomethyl acridine starting material of the general formula (II), adding a solution of (II) to a solution of at least 2 but not more than 2.4 equivalents of the phosphine building block of the general formula (III) according to the amount of 4,5-bis-bromomethylacridine and deprotonating the obtained salt using an alkoxide or hydroxide basein which the variables are defined as follows:M is selected from Li, Na or KR1and R2are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1and R2can also be connected forming rings as cyclic aliphatic or aromatic rings,R3is selected from H and a residue containing hydrocarbon wherein the residue containing hydrocarbon is selected from the group consisting ofCi-Cio-alkyl,Cs-Cio-cycloalkyl,C3-Cio-heterocyclyl comprising at least one heteroatom selected from N, 0 and S,Cs-Cu-aryl,Cs-C -heteroaryl comprising at least one heteroatom selected from N, 0 and S, wherein said Ci-Cio-alkyl C3-C10- cycloalkyl, Cs-C -heterocyclyl, Cs-Cu-aryl, resp. Cs-C -heteroary I optionally has one or more further substituents selected from the group consisting of: F, Cl, Br and Ci-Cio-alkyl.In a preferred embodiment of the invention, R1and R2are identical and Ci-Cio-alkyl or Cs-C -cycloalkyl, more preferable 2-propyl or cyclohexyl. According to a further embodiment, the present invention therefore is also directed to a process as disclosed above, wherein R1and R2are identical and C1 -C10-alkyl or C3-C10-cycloalkyl, more preferable 2-propyl or cyclohexyl.The ligand according formula (I) is preferably selected from compounds according to formula (la) and (lb):According to a further embodiment, the present invention is also directed to a process as disclosed above, wherein the ligand according formula (I) is selected from compounds according to formula (la) and (lb):In a preferred embodiment of the invention, R3is selected from H, methyl, ethyl, 2-propyl or tert-butyl, more preferable methyl or H. According to a further embodiment, the present invention therefore is also directed to a process as disclosed above, wherein R3 is selected from H, methyl, ethyl, 2-propyl or tert-butyl, more preferable methyl or H.In a preferred embodiment of the invention M is selected from Na or K.Methods for the preparation of the starting materials, in particular of 4,5-bis-bromomethylacridine (II) are in principle known to the person skilled in the art. According to a further embodiment, the present invention is also directed to a process as disclosed above, wherein 4,5-Bis-bromomethylacridine (II) is obtained by the bromomethylation of acridin with bromomethylether in sulfuric acid.The starting material of the synthesis 4,5-Bis-bromomethylacridine (II) can for example be obtained by methods described in literature as by the bromomethylation of acridin with bromomethylether in sulfuric acid as described in Synlett, 2003, 15, 2349-2350.The 4,5-Bis-bromomethylacridine (II) obtained by following the procedure as described in Synlett, 2003, 15, 2349-2350 can be used in one embodiment as obtained in the synthesis of ligand (I). In another embodiment, the 4,5-bis-bromo- methylacridine (II) is further purified prior use in the synthesis of ligand (I) for example by an Soxhlet extraction of the material using suitable solvent as for example chloroform or by recrystallization.The structure of the residues R1and R2in the phosphine building block may vary. Preferably, in the phosphine building block (III), R1and R2are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1and R2can also be connected forming rings as cyclic aliphatic or aromatic rings.In a preferred embodiment of the invention, R1and R2are identical and Ci-Cio-alkyl or Cs-C -cycloalkyl, more preferable 2-propyl or cyclohexyl.Preferably, in step (iv), a base in used, in particular MOR3used, with M is selected from Li, Na or K and R3is selected from H and a residue containing hydrocarbon. In a preferred embodiment, MOR3is selected from NaOH, KOH, NaOMe and KOMe.In one embodiment of the invention, the 4,5-bis-bromomethylacridine (II) is dissolved in a suitable solvent and added under inert conditions (absence of oxygen or air) to the phosphine building block (III). Suitable solvents for this step are solvents, which dissolve the acridine but are not reacting with one of the building blocks under the chosen reaction conditions. Suitable solvents are for example halogenated solvents as chloroform, dichloromethane or chlorobenzene, preferably chloroform. According to a further embodiment, the present invention is also directed to a process as disclosed above, wherein solvent (S1) is selected from halogenated solvents, in particular solvents selected from the group consisting of chloroform, dichloromethane or chlorobenzene.The concentration of the 4,5-Bis-bromomethylacridine (II) in this solution preferably is between 1 and 30 weight%, more preferably between 1 and 20 weight%, more preferably between 2 and 10 weight%. According to a further embodiment, the present invention is also directed to a process as disclosed above, wherein the concentration of component (II) in mixture (M1) is in the range o from 1 to 30 weight%.The phosphine building block (III) can be used without solvent but preferably dissolved in organic solvent as the same solvent in which the 4,5-bis-bromomethylacridine (II) is dissolved or other under the reaction conditions inert solvents as aliphatic- or aromatic solvents, halogenated organic solvents, ether solvents or alcohols. In a preferred embodiment, the solvent used for the phosphine building block (III) is selected from hexane, heptane, chloroform, chlorobenzene, methanol or mixture thereof.According to a further embodiment, the present invention is also directed to a process as disclosed above, wherein mixture (M2) comprises a solvent (S2), preferably selected from halogenated solvents.Preferably the concentration of the phosphine in this solution is between 5 and 100 weight%, more preferably between 9 and 50 weight %. According to the invention, the ratio of the phosphine building block (III) to the 4,5-bis-bromo- methylacridine (II) is between 2.4 : 1 to 2.0 : 1. The 4,5-Bis-bromomethylacridine (II) solution is preferably added at a temperature between 0 and 70°C, preferably between 15 and 50°C to the solution of the phosphine building block (III). After complete addition, the reaction mixture preferably is heated under ambient pressure to reflux temperature of the selected solvent and afterwards cooled down to room temperature. Typical reaction times at reflux are between 5 minutes to 48 hours, preferably between 60 minutes and 21 hours.After the reaction, the bis-hydrobromide salt of the product (l)*2HBr is obtained. It can for example be isolated by filtering of, decantation, centrifugation or removal of all volatiles.According to a further embodiment, the present invention is also directed to a process as disclosed above, wherein step (iv) comprises(iv.1 ) separation of the salt (l)*2HBr from mixture (M3);(iv.2) subjecting the salt (l)*2HBr to conditions suitable to deprotonate the salt.According to a further embodiment, the present invention is also directed to a process as disclosed above, wherein the separation according to step (iv.1 ) is carried out by filtering of, decantation, centrifugation or removal of all volatiles.In a preferred embodiment, the salt (l)*2HBr is isolated by filtration and dried for example in vacuum or at ambient pressure at temperature between 20 and 150°C.In the consecutive step, the salt preferably is dissolved or suspended in an alcoholic solvent. In a preferred embodiment, the alcoholic solvent is selected from methanol or ethanol, more preferably the alcoholic solvent is methanol. The ratio of (l)*2HBr to the organic solvent may be in the range of 1 : 100 to 1 : 1 by weight, preferably between 1 : 20 to 1 : 4 by weight .The base MOR3preferably is also dissolved in an appropriate alcoholic solvent as described above and typically added to the (l)*2HBr at a temperature between 0 and 70°C, preferably between 15 and 50°C. The concentration of the base MOR3in the alcoholic solvent preferably is in the range of 1 to 50 weight %, preferably between 2 and 20 weight % and 2 to 10 equivalents base according to the salt (l)*2HBr were used. After the addition of the base solution, the mixture preferably is heated at ambient pressure to reflux for 10 minutes to 5 hours.After the reaction with base, the final product can then be isolated in different manners. For example, all volatiles can be removed in vacuo and the phosphine ligand according formula (I) extracted from the salts formed with an appropriate organic solvent as aliphatic or aromatic hydrocarbons, halogenate hydrocarbons, ethers, ketones or alcohols. Suitable solvents can be for example pentanes, hexanes, benzene, toluene, methyltertbutylether, dichloromethane or mixtures thereof. To remove remaining salts, the organic extract with the ligand can be washed with water and the organic phase dried afterwards with a common drying agent as for example Na2SO4 or MgSC . After removal of all volatiles from the organic layer, the final ligand according formula (I) is obtained. If necessary and depending on the purity required, further common purification steps can be added as recrystallisation, washing or soxhlet extraction.According to a further aspect, the present invention is also directed to the use of the acridine based phosphine ligand of the general formula (I) obtained or obtainable according to the process according to the present invention for the preparation of a metal complex catalyst.According to a further aspect, the present invention relates to a process, preferably to the process as described above, which comprises the step of converting a chemical material obtainable by or obtained by the process as described herein to obtain a product product Q.Preferably, the product Q is selected from: building block or monomer; orpolymer, preferably polymer A, polymer composition, preferably polymer composition A, or polymer product, preferably polymer product A; or cleaning polymer, cleaning surfactant, descaling compound, cleaning biocide or composition or formulation thereof; or agrochemical composition, agrochemical formulation auxiliary or agrochemically active ingredient; or active pharmaceutical ingredient or intermediate thereof, pharmaceutical excipient, animal feed additive, human food additive, dietary supplements, aroma chemical or aroma composition; or aqueous polymer dispersion, preferably polyurethane or polyurethane - poly(meth)acrylate hybrid polymer dispersion, emulsion, binder for paper and fiber coatings, UV-curable acrylic polymer for hot melts and coatings polyisocyanates, hyperbranched polyester polyol, polymeric dispersant for inorganic binder compositions, unsaturated polyester polyol or 100% curable composition; or cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter, further cosmetic ingredient or composition or formulation thereof; or polymer B, polymer composition B, coating composition, other functional composition, foil, molded body, coating or coated substrate.Regarding this process from which the product Q, is obtained, it is preferred: that the content of the chemical material in the product Q is 1 weight-% or more, preferably 2 weight-% or more, more preferably 5 weight-% or more, more preferably 15 weight-% or more, more preferably 30 weight-% or more, more preferably 40 weight-% or more, more preferably 60 weight-% or more, more preferably 80 weight-% or more, more preferably 90 weight-% or more, more preferably 95 weight-% or more; and / or that the content of the chemical material in the product Q is 100 weight-% or less, preferably 95 weight-% or less, more preferably 90 weight-% or less, more preferably 50 weight-% or less, more preferably 25 weight-% or less, more preferably 10 weight-% or less; and preferably wherein the content is determined based on identity preservation and / or segregation and / or mass balance and / or book and claim chain of custody models, preferably based on mass balance, preferably the International Sustainability and Carbon Certification (ISCC) standard.The publication Prior Art Disclosure; Issue 684; paragraphs

[1000] to

[8005] ; ISSN: 2198-4786; published: February 12, 2024 will be regarded as Reference RF1, which is incorporated herein by reference in its entirety. Preferably, the product Q is a product as described in Reference RF1; paragraphs

[1000] to

[8005] , Preferably, the process described herein is further a process for the production of a product.The converting step to obtain the product Q preferably comprises one or more step(s) as described below and can be performed by conventional methods well known to a person skilled in the art. The converting step preferably comprises one or more step(s) selected from: recycling, preferably depolymerizing, gasifying, pyrolyzing, and / or steam cracking; and / or purifying, preferably crystallizing, (solvent) extracting, distilling, evaporating, hydrotreating, absorbing, adsorbing and / or subjecting to ion exchanger; and / orassembling, preferably foaming, synthesizing, chemical conversion, chemically transforming, polymerizing and / or compounding; and / or forming, preferably foaming, extruding and / or molding; and / or finishing, preferably coating and / or smoothing.In addition, the one or more step(s) are described in detail in Reference RF1; paragraphs

[1000] to

[8005] ,The term "building block”, as used in the context of the product Q herein, comprises compounds, which are in a gaseous or liquid state under standard conditions of 0 °C and 0.1 MPa. Building blocks are typically used in chemical industry to form secondary products, which provide a higher structural complexity and / or higher molecular weight than the building block on which the secondary product is based. The building block is preferably selected from the group consisting of hydrogen, carbon monoxide, carbon dioxid, ethylene oxide, ethylene glycols, syngas comprising a mixture of hydrogen and carbon monoxide, alkanes, alkenes, alkynes and aromatic compounds. The alkanes, alkenes, alkynes and aromatic compounds comprise in particular 1 to 12 carbon atoms, respectively.The term "monomer”, as used in the context of the product Q herein, comprises molecules, which can react with each other to form polymer chains by polymerization. The monomer is preferably selected from the group consisting of (meth)acrylic acid, salts of (meth)acrylic acid; in particular sodium, potassium and zinc salts; (meth)acrolein and (meth)acrylates. (Meth)acrylates comprising 1 to 22 carbon atoms are preferred, in particular comprising 1 to 8 carbon atoms. The terms (meth)acrylic acid, (meth)acrolein or (meth)acrylate relate to acrylic acid, acrolein or acrylate and also to methacrylic acid, methacrolein or methacrylate, where applicable. Further, the monomer can be selected from hexamethylenediamine (HMD) and adipic acid.The building block can further be an intermediate compound. The term "intermediate compound”, as used in the context of the product Q herein, comprises organic reagents, which are applied for formation of compounds with higher molecular complexity. The intermediate compound can be selected for example from the group consisting of phosgene, polyisocyanates and propylene oxide. The polyisocyanates are in particular aromatic di- and polyisocyanates, preferably toluene diisocyanate (TDI) and / or diphenylmethane diisocyanate (MDI).The building block and the monomer and typical converting step(s) to obtain the building block or monomer are described in more detail in paragraphs

[1000] to

[1012] of Reference RF1.The term "polymer A”, as used in the context of the product Q herein, comprises thermoplastic, e.g., polyamide or thermoplastic polyurethane, thermoset, e.g., polyurethane, elastomer, e.g., polybutadiene, or a copolymer or a mixture thereof and is defined in more detail in paragraphs

[2001] to

[2007] of Reference RF1 . The term "polymer composition A”, as used in the context of the product Q herein, comprises all compositions comprising a polymer as described above and one or more additive(s), e.g. reinforcement, colorant, modifier and / or flame retardant, and is defined in more detail in paragraph

[2008] of Reference RF1 . The term "polymer product A”, as used in the context of the product Q herein, comprises any product comprising the polymer A and / or polymer composition A as describedabove and is defined in more detail in paragraphs

[2009] and

[2010] of Reference RF1. The step(s) to obtain the polymer, preferably polymer A, polymer composition, preferably polymer composition A or polymer product, preferably polymer product A is / are described in more detail in paragraph

[2011] of Reference RF1 .The term "industrial use polymer”, as used in the context of the product Q herein, comprises rheology, polycarboxylate, alkoxylated polyalkylenamine, alkoxylated polyalkylenimine, polyether-based, dye inhibition and soil release cleaning polymers defined in more detail in paragraphs

[3035] to

[3044] of Reference RF1. The term "industrial use surfactant”, as used in the context of the product Q herein, comprises non-ionic, anionic and amphoteric industrial use surfactants defined in more detail in paragraphs

[3008] to

[3034] of Reference RF1. The term "industrial use descaling compound”, as used in the context of the product Q herein, comprises non-phosphate based builders (NPB) and phosphonates (CoP) described in more detail in paragraphs

[3001] to

[3005] of Reference RF1. The term "industrial use biocide”, as used in the context of the product Q herein, refers to a chemical compound that kills microorganisms or inhibits their growth or reproduction defined in more detail in paragraphs

[3006] to

[3007] of Reference RF1. The term "industrial use solvent”, as used in the context of the product Q herein, comprises alkyl amides, alkyl lactamides, alkyl esters, lactate esters, alkyl diester, cyclic alkyl diester, cyclic carbonates, aromatic aldehydes and aromatic esters defined in more detail in paragraphs

[3045] to

[3055] of Reference RF1. The term "industrial use dispersant”, as used in the context of the product Q herein, comprises anionic and non-ionic industrial use dispersants defined in more detail in paragraphs

[3056] to

[3058] of Reference RF1 . The term "composition and / or formulation thereof' with reference to the industrial use polymers, industrial use surfactants, descaling compounds and / or industrial use biocides refers to industrial use compositions and / or institutional use products and / or fabric and home care products and / or personal care products defined in more detail in paragraph

[3059] of Reference RF1. The converting step(s) to obtain the industrial use polymer, industrial use surfactant, descaling compound and / or industrial use biocide are defined in more detail in paragraph

[3060] of Reference RF1. The converting steps to obtain the industrial use composition or formulation of the industrial use polymer, industrial use surfactant, descaling compound and / or industrial use biocide are defined in more detail in paragraph

[3061] of Reference RF1.The term "agrochemical composition”, as used in the context of the product Q herein, typically relates to a composition comprising an agrochemically active ingredient and at least one agrochemical formulation auxiliary. Examples of agrochemical compositions, active ingredients and auxiliaries are described in more detail in Reference RF1 , paragraph

[4001] , The agrochemical composition may take the form of any customary formulation. The agrochemical compositions are prepared in a known manner, e.g. described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The converting step(s) to obtain the agrochemically active ingredients and auxiliaries may be conducted in analogy to the production step(s) of their analogues that are based on petrochemicals or other precursors that are not gained by recycling processes. In addition, conversion to compounds mentioned in sections "Polymer” and "Cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter, further cosmetic ingredient or compositions or formulations thereof” may be performed as described in these sections as well as the respective paragraphs in Reference RF1.The term active pharmaceutical ingredients and / or intermediates thereof, as used in the context of the product Q herein, comprises substances that provide pharmacological activity or other direct effect in the diagnosis, cure, mitigation, treatment, or prevention of disease, or to affect the structure or any function of the body. Intermediates thereof are isolated products that are generated during a multi-step route of synthesis of an active pharmaceutical ingredient. The term pharmaceutical excipients, as used in the context of the product Q herein, comprises compounds or compound mixtures used in compositions for various pharmaceutical applications, which are not substantially pharmaceutically active on itself. Active pharmaceutical ingredients and / or intermediates thereof and pharmaceutical excipients are defined in more detail in paragraph

[5001] of Reference RF1. The converting step(s) to obtain the active pharmaceutical ingredients and / or intermediates thereof and pharmaceutical excipients may comprise one or more synthesis steps and can be performed by conventional synthesis and techniques well known to a person skilled in the art.The terms animal feed additives, human food additives, dietary supplements, as used in the context of the product Q herein, comprises Vitamins, Pro-Vitamins and active metabolites thereof including intermediates and precursors, especially Vitamin A, B, E, D, K and esters thereof, like acetate, propionate, palmitate esters or alcohols thereof like retinol or salts thereof and any combinations thereof; Tetraterpenes, especially isoprenoids like carotenoids and xanthophylls including their intermediates and precursors as well as mixtures and derivates thereof, especially beta carotene, Canthaxanthin, Citranaxanthin, Astaxanthin, Zeaxanthin, Lutein, Lycopene, Apo-carotenoids, and any combinations thereof; organic acids, especially formic acid, propionic acid and salts thereof, such as sodium, calcium or ammonium salts, and any combinations thereof, such as but not limited to mixtures of formic acid and sodium formiate, propionic acid and ammonium propionate, formic acid and propionic acid, formic acid and sodium formiate and propionic acid, propionic acid and sodium propionate and formic acid and sodium formiate; glycerides of carboxylic acids and short and medium chain fatty acids, conjugated linoleic acids, such as omega-6 fatty acid (C18:2) methyl ester and 1 ,2-propandiol and beverage stabilizers, such as polyvinylpyrrolidone-polymer or polyvinylimidazole / polyvinylpyr- rolidone-copolymer. Animal feed additives, human food additives and dietary supplements are defined in more detail in paragraph

[5002] of Reference RF1. The converting step(s) to obtain the animal feed additives, human food additives, dietary supplements may comprise one or more synthesis steps and can be performed by conventional synthesis and techniques well known to a person skilled in the art.The terms aroma chemical and aroma composition as used in the context of the product Q herein, comprise a volatile organic substance with a molecular weight between 70-250 g / mol comprising a functional group with a carbon skeleton of C5-C16 carbon atoms comprising linear, branched, cyclic, for example with a ring size of C5-C18, bicyclic or tricyclic aliphatic chains and but not necessarily one or more unsaturated structural elements like double bonds, triple bonds, aromatics or heteroaromatics and preferably the one or more additional functional groups are selected from alcohol, ether, ester, ketone, aldehyde, acetal, carboxylic acid, nitrile, thiol, amine. In one aspect, the aroma chemical is a terpene-based aroma chemical, for example selected from monoterpenes and monoterpenoids, sesquiterpenes and sesquiterpenoids, diterpenes, triterpenes or tetraterpenes. Aroma chemicals can be combined with further aromachemicals to give an aroma composition. Aroma chemicals and aroma compositions are defined in more detail in paragraph

[5003] of Reference RF1 . The converting step(s) to obtain the aroma chemical and aroma composition may comprise one or more synthesis steps and can be performed by conventional synthesis and techniques well known to a person skilled in the art.The term "aqueous polymer dispersion”, as used in the context of the product Q herein, comprises aqueous compositions) comprising dispersed polymer(s) and is defined in more detail in the section

[6001] entitled "aqueous polymer dispersion” of Reference RF1. The dispersed polymer(s) may be selected from acrylic emulsion polymer(s), styrene acrylic emulsion polymer(s), styrene butadiene dispersion(s), aqueous dispersion(s) comprising composite particles, acrylate alkyd hybrid dispersion(s), polyurethane(s) (including UV-curable polyurethanes) and polyurethane - poly(meth)acrylate hybrid polymer(s). The term "emulsion polymer”, as used in the context of the product Q herein, comprises polymer(s) made by free-radical emulsion polymerization. Aqueous polyurethane dispersion(s) are defined in more detail in the section

[6002] entitled "Polyurethane dispersions” of Reference RF1. UV-curable polyure- thane(s) is / are defined in more detail in the section

[6017] of Reference RF1. Polyurethane - poly(meth)acrylate hybrid polymer(s) is / are defined in more detail in the section

[6016] of Reference RF1.The term "polymeric dispersant”, as used in the context of the product Q herein, comprises preferably polymer(s) comprising polyether side chain, in particular polycarboxylate ether polymer(s) and polycondensation product(s) defined in more detail in paragraph

[6020] entitled "Polymeric dispersant” of Reference RF1.The converting (polymerization) step(s) to obtain the aqueous polymer dispersion(s) comprising emulsion polymer(s) is / are defined in more detail in the section

[6003] entitled "Emulsion polymerization” of Reference RF1.The converting (polymerization) step(s) to obtain the aqueous polyurethane dispersion(s) is / are defined in more detail in the section

[6014] entitled "Process for the preparation of aqueous polyurethane dispersions” and section [6017)] entitled "Aqueous UV-curable polyurethane dispersions, their preparation and use and compositions containing them” of Reference RF1 .Composition(s) and uses of aqueous polymer dispersion(s) and of polymeric dispersant(s) are defined in more detail in the following sections of Reference RF1 : section

[6004] entitled "Uses of aqueous polymer dispersions”, section

[6005] entitled "Binders for architectural and construction coatings” section

[6006] entitled "Binders for paper coating” section

[6007] entitled "Binders for fiber bonding” section

[6008] entitled "Adhesive polymers and adhesive compositions” section

[6015] entitled "Aqueous polyurethane dispersions suitable for use in coating compositions” section

[6016] entitled "Aqueous polyurethane - poly(meth)acrylate hybride polymer dispersions suitable for use in coating compositions” section

[6017] entitled "Aqueous UV-curable polyurethane dispersions, their preparation and use and compositions containing them”section

[6018] entitled "Inorganic binder compositions comprising polymeric dispersants and their use”

[6019] 100% curable coating compositionsUV-crosslinkable poly(meth)acrylate(s) and its / their uses are defined in more detail in section

[6009] entitled "UV- crosslinkable poly(meth)acrylates for use in UV-curable solvent-free hotmelt adhesives and their use for making pressure-sensitive self-adhesive articles” of Reference RF1.Polyisocyanate(s), composition(s) comprising them and their uses are defined in more detail in section

[6010] entitled "Polyisocyanates” of Reference RF1.Hyperbranched polyester polyol (s) and its / their uses are defined in more detail in section

[6011] entitled "Organic solvent based hyperbranched polyester polyols suitable for use in coating compositions” of Reference RF1. The converting step(s) to obtain the hyperbranched polyester polyols is / are defined in more detail in the section

[6012] entitled "Preparation of organic solvent based hyperbranched polyester polyols” of Reference RF1 . Coating compositions) comprising hyperbranched polyester polyol(s), polyisocyanate(s) and additive(s) and substrate(s) coated therewith are defined in more detail in section

[6013] entitled "Organic solvent based two component coating compositions comprising hyperbranched polyester polyols and polyisocyanates” of Reference RF1.Unsaturated polyester polyol(s), solvent-based coating composition(s) comprising said unsaturated polyester pol- yol(s) and substrate(s) for coating with said coating composition(s) are defined in more detail in section

[6018] entitled "Organic solvent based coating composition comprising unsaturated polyester polyols” of Reference RF1. 100% curable coating composition(s) is / are defined in more detail in section

[6019] of Reference RF1.Polymeric dispersant(s) for inorganic binder compositions is / are defined in more detail in section

[6020] of Reference RF1. The inorganic binder composition(s) comprising the polymeric dispersants and their use are defined in more detail in section

[6021] of Reference RF1 . The converting step(s) to obtain the polymeric dispersant(s) are defined in more detail in section

[6020] of Reference RF1 . The term "inorganic binder composition” comprising the polymeric dispersant(s), as used in the context of the product Q herein, comprises preferably in particular hydraulically setting compositions and compositions comprising calcium sulfate and is defined in more detail in section

[6021] of Reference RF1 entitled "Inorganic binder compositions comprising the polymeric dispersant and their use”. Specific building material formulation(s) comprising polymeric dispersant(s) or building product(s) produced by a building material formulation comprising a polymeric dispersant are disclosed in more detail in section

[6021] of Reference RF1.The term "cosmetic surfactant”, as used in the context of the product Q herein, comprises non-ionic, anionic, cationic and amphoteric surfactants and is defined in more detail in paragraph

[7002] of Reference RF1. The term "emollient”, as used in the context of the product Q herein, refers to a chemical compound used for protecting, moisturizing, and / or lubricating the skin and is defined in more detail in paragraph

[7003] of Reference RF1. The term "wax”, as used in the context of the product Q herein, comprises pearlizers and opacifiers and is defined in more detail in para-graph

[7004] of Reference RF1 . The term "cosmetic polymer”, as used in the context of the product Q herein, comprises any polymer that can be used as an ingredient in a cosmetic formulation and is defined in more detail in paragraph

[7005] of Reference RF1 . The term "UV filter”, as used in the context of the product Q herein, refers to a chemical compound that blocks or absorbs ultraviolet light and is defined in more detail in paragraph

[7006] of Reference RF1 . The term "further cosmetic ingredient”, as used in the context of the product Q herein, comprises any ingredient suitable for making a cosmetic formulation. Several sources disclose cosmetically acceptable ingredients. E. g. the database Cosing on the internet pages of the European Commission discloses cosmetic ingredients and the International Cosmetic Ingredient Dictionary and Handbook, edited by the Personal Care Products Council (PCPC), discloses cosmetic ingredients. The term "composition and / or formulation thereof' with reference to the cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter and / or further cosmetic ingredient refers to personal care and / or cosmetic compositions or formulations defined in more detail in paragraph

[7007] of Reference RF1 . The converting step(s) to obtain the cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter or further cosmetic ingredient is / are defined in more detail in paragraph

[7008] of Reference RF1.The terms "polymer B”, "polymer composition B”, "coating composition”, "other functional composition”, "foil”, "molded body”, "coating” and "coated substrate” are well known to the person skilled in the art and are defined in more detail from paragraph

[8000] to

[8005] of Reference RF1.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.1 . Process for preparing an acridine based phosphine ligands of the general formula (I),comprising(i) providing a mixture (M1) comprising 4,5-Bis-bromomethylacridine (II) and at least one solvent (S1)) comprising a phosphine building block (III)(Hi);(ill) adding mixture (M1) to mixture (M2) to obtain a mixture (M3) comprising a salt (l)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4(l)*2HBr subjecting mixture (M3) to conditions suitable to deprotonate the salt (l)*2HBr; whereinR1and R2are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1and R2can also be connected forming rings as cyclic aliphatic or aromatic rings. The process according to embodiment 1 , wherein in step (iv), component MOR3is used wherein M is selected from Li, Na or K, andR3 is selected from H and a residue containing hydrocarbon wherein the residue containing hydrocarbon is selected from the group consisting ofC1-C10-alkyl,C3-C10-cycloalkyl,C3-C10-heterocyclyl comprising at least one heteroatom selected from N, 0 and S, C5-C14-aryl,C5-C10-heteroaryl comprising at least one heteroatom selected from N, 0 and S, wherein said C1 -C10-alkyl C3-C10-cycloalkyl, C3-C10-heterocyclyl, C5-C14-aryl, resp. C5-C10-heteroaryl optionally has one or more further substituents selected from the group consisting of: F, Cl, Br and C1-C10-alkyl.3. The process according to any one of embodiments 1 to 2, wherein R3 is selected from H, methyl, ethyl, 2-propy I or tert-butyl, more preferable methyl or H.4. The process according to any one of embodiments 1 to 3, wherein M is selected from Na or K.5. The process according to any one of embodiments 1 to 4, wherein R1and R2are identical and C1-C10-alkyl or C3-C10-cycloalkyl, more preferable 2-propyl or cyclohexyl.6. The process according to any one of embodiments 1 to 5, wherein the ligand according formula (I) is selected from compounds according to formula (la) and (lb):7. The process according to any one of embodiments 1 to 6, wherein step (iv) comprises(iv.1 ) separation of the salt (l)*2HBr from mixture (M3);(iv.2) subjecting the salt (l)*2H Br to conditions suitable to deprotonate the salt.8. The process according to any one of embodiments 1 to 7, wherein the separation according to step (iv.1 ) is carried out by filtering of, decantation, centrifugation or removal of all volatiles.9. The process according to any one of embodiments 1 to 8, wherein 4,5-Bis-bromomethylacridine (II) is obtained by the bromomethylation of acridin with bromomethylether in sulfuric acid.10. The process according to any one of embodiments 1 to 9, wherein the concentration of component (II) in mixture (M1) is in the range o from 1 to 30 weight%.11. The process according to any one of embodiments 1 to 10, wherein solvent (S1) is selected from halogenated solvents, in particular solvents selected from the group consisting of chloroform, dichloromethane or chlorobenzene.12. The process according to any one of embodiments 1 to 11, wherein mixture (M2) comprises a solvent (S2), preferably selected from halogenated solvents.13. Acridine based phosphine ligand of the general formula (I),obtained or obtainable according to the process according to any one of embodiments 1 to 12.14. Acridine based phosphine ligand of the general formula (I),obtained or obtainable according to a process comprising(I) providing a mixture (M1) comprising 4,5-Bis-bromomethylacridine (II) and at least one solvent (S1)(II) providing a mixture (M2) comprising a phosphine building block (III)(iii) adding mixture (M1) to mixture (M2) to obtain a mixture (M3) comprising a salt (l)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4(iv) subjecting mixture (M3) to conditions suitable to deprotonate the salt (l)*2HBr; whereinR1and R2are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1and R2can also be connected forming rings as cyclic aliphatic or aromatic rings. Use of the acridine based phosphine ligand of the general formula (I) obtained or obtainable according to the process according to any one of embodiments 1 to 12 for the preparation of a metal complex catalyst. Use of the acridine based phosphine ligand of the general formula (I) o according to any one of embodiments 13 or 14 for the preparation of a metal complex catalyst. Use of the acridine based phosphine ligand of the general formula (I) obtained or obtainable according to a process a for preparing an acridine based phosphine ligands of the general formula (I),comprising providing a mixture (M1) comprising 4,5-bis-bromomethylacridine (II) and at least one solvent (S1)providing a mixture (M2) comprising a phosphine building block (III)adding mixture (M1) to mixture (M2) to obtain a mixture (M3) comprising a salt (l)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4(iv) subjecting mixture (M3) to conditions suitable to deprotonate the salt (l)*2HBr; whereinR1and R2are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1and R2can also be connected forming rings as cyclic aliphatic or aromatic rings.18. The use according to embodiment 17, wherein in step (iv), component MOR3is used wherein M is selected from Li, Na or K, andR3 is selected from H and a residue containing hydrocarbon wherein the residue containing hydrocarbon is selected from the group consisting of C1-C10-alkyl, C3-C10-cycloalkyl,C3-C10-heterocyclyl comprising at least one heteroatom selected from N, 0 and S,C5-C14-aryl,C5-C10-heteroaryl comprising at least one heteroatom selected from N, 0 and S, wherein said C1 -C10-alkyl C3-C10-cycloalkyl, C3-C10-heterocyclyl, C5-C14-aryl, resp. C5-C10-heteroaryl optionally has one or more further substituents selected from the group consisting of: F, Cl, Br and C1-C10-alkyl.19. The use according to any one of embodiments 17 or 18, wherein R3 is selected from H, methyl, ethyl, 2-propyl or tert-butyl, more preferable methyl or H.20. The use according to any one of embodiments 17 to 19, wherein M is selected from Na or K.21. The use according to any one of embodiments 17 to 20, wherein R1and R2are identical and C1-C10-alkyl or C3-C10-cycloalkyl, more preferable 2-propyl or cyclohexyl.22. The use according to any one of embodiments 17 to 21 , wherein the ligand according formula (I) is selected from compounds according to formula (la) and (lb):23. The use according to any one of embodiments 17 to 22, wherein step (iv) comprises(iv.1 ) separation of the salt (l)*2HBr from mixture (M3);(iv.2) subjecting the salt (l)*2HBr to conditions suitable to deprotonate the salt.24. The use according to any one of embodiments 17 to 23, wherein the separation according to step (iv.1 ) is carried out by filtering of, decantation, centrifugation or removal of all volatiles.25. The use according to any one of embodiments 17 to 24, wherein 4,5-bis-bromomethylacridine (II) is obtained by the bromomethylation of acridin with bromomethylether in sulfuric acid.26. The use according to any one of embodiments 17 to 25, wherein the concentration of component (II) in mixture (M1) is in the range o from 1 to 30 weight%.27. The use according to any one of embodiments 17 to 26, wherein solvent (S1) is selected from halogenated solvents, in particular solvents selected from the group consisting of chloroform, dichloromethane or chlorobenzene.28. The use according to any one of embodiments 17 to 27, wherein mixture (M2) comprises a solvent (S2), preferably selected from halogenated solvents.29. Process for preparing an acridine based phosphine ligands of the general formula (I),comprising(I) providing a mixture (M1) comprising 4,5-Bis-bromomethylacridine (II) and at least one solvent (S1 )(II) providing a mixture (M2) comprising a phosphine building block (III)(Hi);(ill) adding mixture (M1) to mixture (M2) to obtain a mixture (M3) comprising a salt (l)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4(l)*2HBr(iv) subjecting mixture (M3) to conditions suitable to deprotonate the salt (l)*2HBr; whereinR1and R2are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1and R2can also be connected forming rings as cyclic aliphatic or aromatic rings, wherein in step (iv), component MOR3is used wherein R3 is selected from H, methyl, ethyl, 2-propy I or tert-butyl, more preferable methyl or H and M is selected from Na or K. Process for preparing an acridine based phosphine ligands of the general formula (I),comprising(i) providing a mixture (M1) comprising 4,5-Bis-bromomethylacridine (II) and at least one solvent (S1)providing a mixture (M2) comprising a phosphine building block (III)adding mixture (M1) to mixture (M2) to obtain a mixture (M3) comprising a salt (l)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4(l)*2HBr(IV) subjecting mixture (M3) to conditions suitable to deprotonate the salt (l)*2HBr; whereinR1and R2are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1and R2can also be connected forming rings as cyclic aliphatic or aromatic rings, wherein in step (iv), component MOR3is used wherein R3 is selected from H, methyl, ethyl, 2-propy I or tert-butyl, more preferable methyl or H and M is selected from Na or K and wherein the ligand according formula (I) is selected from compounds according to formula (la) and (lb):Process for preparing an acridine based phosphine ligands of the general formula (I),comprising(i) providing a mixture (M1) comprising 4,5-bis-bromomethylacridine (II) and at least one solvent (S1)(II) providing a mixture (M2) comprising a phosphine building block (III)(Ill);(iii) adding mixture (M1) to mixture (M2) to obtain a mixture (M3) comprising a salt (l)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4(iv) subjecting mixture (M3) to conditions suitable to deprotonate the salt (l)*2HBr; whereinR1 and R2 are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1 and R2 can also be connected forming rings as cyclic aliphatic or aromatic rings, wherein in step (iv), component M0R3 is used, wherein R3 is selected from H, methyl, ethyl, 2-propyl or tertbutyl, more preferable methyl or H and M is selected from Na or K and wherein step (iv) comprises(iv.1 ) separation of the salt (l)*2HBr from mixture (M3);(iv.2) subjecting the salt (l)*2HBr to conditions suitable to deprotonate the salt.A process, preferably according to any one of embodiments 1 to 12 or 29 to 31, comprising the step of converting a chemical material obtainable by or obtained by the process according to any one of embodiments 1 to 12 or 29 to 31 to obtain a product product Q.The process of embodiment 32, wherein the product Q is selected from: building block or monomer; or polymer, preferably polymer A, polymer composition, preferably polymer composition A, or polymer product, preferably polymer product A; or cleaning polymer, cleaning surfactant, descaling compound, cleaning biocide or composition or formulation thereof; oragrochemical composition, agrochemical formulation auxiliary or agrochemically active ingredient; or active pharmaceutical ingredient or intermediate thereof, pharmaceutical excipient, animal feed additive, human food additive, dietary supplements, aroma chemical or aroma composition; or aqueous polymer dispersion, preferably polyurethane or polyurethane - poly(meth)acrylate hybrid polymer dispersion, emulsion, binder for paper and fiber coatings, UV-curable acrylic polymer for hot melts and coatings polyisocyanates, hyperbranched polyester polyol, polymeric dispersant for inorganic binder compositions, unsaturated polyester polyol or 100% curable composition; or cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter, further cosmetic ingredient or composition or formulation thereof; or polymer B, polymer composition B, coating composition, other functional composition, foil, molded body, coating or coated substrate.34. The process of embodiment 33, wherein the content of the chemical material in the product Q is 1 weight-% or more, preferably 2 weight-% or more, more preferably 5 weight-% or more, more preferably 15 weight-% or more, more preferably 30 weight- % or more, more preferably 40 weight-% or more, more preferably 60 weight-% or more, more preferably 80 weight-% or more, more preferably 90 weight-% or more, more preferably 95 weight-% or more; and / or wherein the content of the chemical material in the product Q is 100 weight-% or less, preferably 95 weight-% or less, more preferably 90 weight-% or less, more preferably 50 weight-% or less, more preferably 25 weight- % or less, more preferably 10 weight-% or less; and preferably wherein the content is determined based on identity preservation and / or segregation and / or mass balance and / or book and claim chain of custody models, preferably based on mass balance, preferably the International Sustainability and Carbon Certification (ISCC) standard.The invention is illustrated by the following examples.ExamplesFigures in percent are each based on % by weight, unless explicitly stated otherwise.1. GeneralAll chemicals and solvents were purchased from Sigma-Aldrich or ABCR and used without further purification.All reactions and manipulations were performed under an inert N2- or Ar-atmosphere in the absence of air or O2 using standard Schlenk techniques and / or an N2-filled glovebox. All solvents were degassed prior used.1H and31P NMR spectra were recorded on Broker Avance 500 MHz spectrometer and were referenced to the residual proton (1H) resonance peaks of the solvent. Chemical shifts (5) are reported in ppm.4,5-Bis-bromomethylacridine (II) was obtained by the bromomethylation of acridin with bromomethylether in sulfuric acid as described in Synlett, 2003, 15, 2349-2350. Synthesis of ligand la:10.4 g (28.48 mmol; 1 equivalent) 4,5-Bis-bromomethylacridine (II) was dissolved in 300 mL CHCI3 and put in a 500 mL dropping funnel. 7.74 g (65.52 mmol, 2.3 equivalents) di-ispropyl-phosphine (Illa) dissolved in 70 g n-hexane were put in a 500 mL four neck flask equipped with a reflux condenser and the dropping funnel containing the 4,5-Bis-bromomethylacridine (II) which was the added within 5 minutes under stirring at a temperature of 18-20°C. The mixture was stirred for another hour at 20°C and then heated to reflux (61 °C) for 20 hours, whereby a yellow suspension was formed. After cooling to room temperature, the solid (la)*2HBr was filtered- off and dried in vacuum to obtain 15.47 g (25.7 mmol) of (la)*2HBr. After drying, the (la)*2HBr was dissolved in 100 mL Methanol, put in a 500 ml three neck flask equipped with a dropping funnel and a reflux condenser. Then a solution of 2.97 g NaOMe (55 mmol, 2.14 equivalents according to (la)*2HBr) in 100 mL Methanol was added dropwise at 20°C. After the addition, the mixture was heated to reflux for one hour. After cooling to room temperature, all volatiles were removed in vacuum. The residue was extracted with 75 mL dichloromethane and the organic phase washed with 20 mL water. The organic phase was dried over Na2SO4 and then the solvent removed in vacuo. The residue was again dissolved in 50 mL MeOH at 60°C and then slowly cooled to room temperature. The product is crystallized out as a yellow solid, was filtered-off and dried in vacuum to obtain 7.27 g (58.1 % Yield) of the ligand la.The signals in the1H-NMR- as well as the31P-NMR-spectra recorded in CeDe were matching with the signals as reported for ligand la in Angew. Chem. Int. Ed. 2008, 47, 8661-8664. According to the integration in the31P- NMR spectra, the purity of the so obtained ligand la is >99%. Synthesis of ligand lb:10.83 g (29.68 mmol; 1 equivalent) 4,5-Bis-bromomethylacridine (II) was dissolved in 300 mL CHCI3 and put in a 500 mL dropping funnel. 11.77 g (59.37 mmol, 2.0 equivalents) di-cyclohexyl-phosphine (III) dissolved in 50 mL CHCI3 were put in a 500 mL four neck flask equipped with a reflux condenser and the dropping funnel containing the 4,5-Bis-bromomethylacridine (II) which was the added within 5 minutes under stirring at a temperature of 25-40°C. The mixture was then heated to reflux for 15 minutes and then 20 hours at 20°C, whereby a yellow suspension was formed. All volatiles were removed in vacuum to obtain a yellow residue consisting of (lb)*2HBr. Then a solution of 2.50 g (62.50 mmol) NaOH dissolved in 100 mL MeOH was added at room temperature to (lb)*2HBr and heated to reflux for 5 minutes. After cooling to 20°C, all volatiles were removed invacuum and the residue suspended in a mixture of 200 mL n-pentane and 10 mL water. The pentane layer was separated and combined with the organic extract from the second Soxhlet extraction below. The remaining solid was filtered-off and dried in vacuum and then extracted with n-pentane in a Soxhlet extraction to obtain a yellow crystalline solid from the pentane extract, which was filtered-off and dried in vacuum to yield a first batch of 5.20 g of ligand lb. The mother liquor was used in the second Soxhlet extraction below.The remaining solid in the Soxhlet extractor was then extracted wit 100 mL dichloromethane, the extraction solution washed with 20 mL water, dried over Na2SO4 and then all volatiles removed in vacuo. This residue was again extracted in a Soxhlet extraction, whereby as extraction medium the combined pentane layers from above were used. After extraction overnight, a second batch of 4.55 g of lb where obtained as a yellow crystalline solid from the pentane extract after filtering-off and drying in vacuum.A combined amount of 9.75 g (0.0162 mmol, 54% Yield) of ligand lb was obtained by this procedure.The signals in the1H-NMR- as well as the31P-NMR-spectra recorded in CeDe were matching with the signals as reported for ligand lb in WO2012119929 According to the integration in the31P-NMR spectra, the purity of the so obtained ligand la is >93%.Literature cited:Angew. Chem. I nt. ed. 2008, 47, 8661-8664J. Am. Chem. Soc. 2014, 136, 5923-5929J. Am. Chem. Soc. 2016, 138, 9077-9080WC2010 / 018570WC2020 / 141520WC2010 / 018570Synlett, 2003, 15, 2349-2350

Claims

Claims1 . Process for preparing an acridine based phosphine ligands of the general formula (I),comprising(I) providing a mixture (M1) comprising 4,5-bBis-bromomethylacridine (II) and at least one solvent (S1)providing a mixture (M2) comprising a phosphine building block (III)adding mixture (M1) to mixture (M2) to obtain a mixture (M3) comprising a salt (l)*2HBr, wherein the molar ratio of component (II) and component (III) is in the range of from 1 : 2 to 1 : 2.4(l)*2HBr(iv) subjecting mixture (M3) to conditions suitable to deprotonate the salt (l)*2HBr; wherein in step (iv), component MOR3is used wherein M is selected from Li, Na or K, andR3 is selected from H and a residue containing hydrocarbon wherein the residue containing hydrocarbon is selected from the group consisting of C1-C10-alkyl, C3-C10-cycloalkyl,C3-C10-heterocyclyl comprising at least one heteroatom selected from N, 0 and S, C5-C14-aryl,C5-C10-heteroaryl comprising at least one heteroatom selected from N, 0 and S, wherein said C1 -C10-alkyl 03-010-cycloalkyl, 03-010-heterocyclyl, C5-C14-aryl, resp. C5-C10-heteroaryl optionally has one or more further substituents selected from the group consisting of: F, Cl, Br and 01 -010-alkyl; and whereinR1and R2are independently of one another selected from the group consisting of a residue containing hydrocarbon and R1and R2can also be connected forming rings as cyclic aliphatic or aromatic rings.

2. The process according to claim 1 , wherein R3 is selected from H, methyl, ethyl, 2-propyl or tert-butyl, more preferable methyl or H.

3. The process according to any one of claims 1 or 2, wherein M is selected from Na or K.

4. The process according to any one of claims 1 to 3, wherein R1and R2are identical and C1 -C10-alkyl or C3- C10-cycloalkyl, more preferable 2-propyl or cyclohexyl.

5. The process according to any one of claims 1 to 4, wherein the ligand according formula (I) is selected from compounds according to formula (la) and (lb):

6. The process according to any one of claims 1 to 5, wherein step (iv) comprises(iv.1 ) separation of the salt (l)*2HBr from mixture (M3);(iv.2) subjecting the salt (l)*2HBr to conditions suitable to deprotonate the salt.

7. The process according to any one of claims 1 to 6, wherein the separation according to step (iv.1 ) is carried out by filtering of, decantation, centrifugation or removal of all volatiles.

8. The process according to any one of claims 1 to 7, wherein 4,5-Bis-bromomethylacridine (II) is obtained by the bromomethylation of acridin with bromomethylether in sulfuric acid.

9. The process according to any one of claims 1 to 8, wherein the concentration of component (II) in mixture (M1) is in the range o from 1 to 30 weight%.

10. The process according to any one of claims 1 to 9, wherein solvent (S1 ) is selected from halogenated solvents, in particular solvents selected from the group consisting of chloroform, dichloromethane or chlorobenzene.11 . The process according to any one of claims 1 to 10, wherein mixture (M2) comprises a solvent (S2), preferably selected from halogenated solvents.

12. Use of the acridine based phosphine ligand of the general formula (I) obtained or obtainable according to the process according to any one of claims 1 to 11 for the preparation of a metal complex catalyst.

13. A process, preferably according to any one of claims 1 to 11, comprising the step of converting a chemical material obtainable by or obtained by the process according to any one of claims 1 to 11 to obtain a product Q.