The present invention is related to a method for the synthesis of a heterocyclic hydrogen phosphine oxide, having the general formula (I), wherein: - R is a aliphatic or aromatic divalent group optionally comprising one or more heteroatoms and optionally comprising one or more substituents and - X and Y are independently selected from -O-, -C(O)O- and -NR'- wherein R' is a monovalent group optionally comprising one or more heteroatoms comprising the steps of: a) forming a reaction mixture by mixing a compound having the general formula HX-R-YH and tetraphosphorus hexaoxide; b) recovering the resulting compound comprising the heterocyclic hydrogen phosphine oxide.
C07F 9/6584 - Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
The present invention is related to a new method for the synthesis of alkane-1-hydroxy-,1-diphosphonic acid or its salts which includes the steps of -reacting tetraphosphorus hexaoxide and a carboxylic acid under controlled reaction conditions; -hydrolyzing the formed alkane-1-hydroxy-1,1-diphosphonic acid condensates to form alkane-1-hydroxy-1,1-diphosphonic acid; -precipitating the alkane-1-hydroxy-1,1-diphosphonic acid through the use of a suitable solvent; -filtering the alkane-1-hydroxy-1,1-diphosphonic acid and recovering the mother liquor and the suitable solvent.1 The process according to the method of the present invention is highly controllable and is further characterized by a high selectivity.
The present invention is related toa method for the synthesis of ethane-1-hydroxy-1,1-diphosphonic acid or its salt which includes the steps of reacting tetraphosphorus hexaoxideand acetic acid under controlled reaction conditions; hydrolyzing the formed ethane-1-hydroxy-1,1-diphosphonic acid condensates to form ethane-1-hydroxy-1,1-diphosphonic acid; further processing the ethane-1-hydroxy-1,1-diphosphonic acid solution. The process according to the method of the present invention is highly controllable and further is characterized by a high selectivity.
The present invention is related to a method for the synthesis of N- phosphonoalkyliminodiacetic acid or derivatives thereof comprising the steps of: a) forming a reaction mixture comprising an acid catalyst, a compound having the general formula R1 -CH2-NX-CH2-R2 and a compound having one or more P-O-P anhydride moieties, to form a compound having the general formula R1 - CH2-N-CH2(P03H2)-CH2-R2, its dehydrated forms or their derivatives, wherein - the compound of the formula R1 -CH2-NX-CH2-R2 is characterized in that: - X is -CH2-OH or -CH2-COOH; - R1 and R2 are independently selected from the group consisting of nitrile, C1 -C4 alkyl carboxylate, or are both carbonyl groups linked by means of a hydrogen substituted nitrogen atom or a C1 -C4- akyl substituted nitrogen atom; - the P-O-P anhydride comprising compound is characterized in that said anhydride moieties comprise one P atom at the oxidation state (+I II ) and one P atom at the oxidation state (+I II ) or (+V); and b) hydrolysing the reaction mixture to form N- phosphonomethyliminodiacetic acid or one of its derivatives.
The present invention is related to a method for the synthesis of an aminoalkylenephosphonic acid or its phosphonate esters comprising the following steps: a) forming, in the presence of an aldehyde or ketone and an acid catalyst, a reaction mixture by mixing a compound comprising at least one HNR1R2 moiety or a salt thereof, with a compound having one or more P-O-P anhydride moieties, said moieties comprising one P atom at the oxidation state (+III) and one P atom at the oxidation state (+III) or (+V), wherein the ratio of moles of aldehyde or ketone to N-H moieties is 1 or more and wherein the ratio of N-H moieties to P-O-P anhydride moieties is 0.3 or more and, b) recovering the resulting aminoalkylenephosphonic acid comprising compound or its phosphonate esters.
A01N 57/20 - Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
6.
METHOD FOR THE SYNTHESIS OF N-(PHOSPHONOMETHYL)GLYCINE
The present invention is related to a new method for the synthesis of N- (phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters and its phosphonate ester salts, comprising the steps of: a) forming a reaction mixture comprising an acid catalyst, Ν,Ν'- bis(carboxymethyl)-2,5-diketopiperazine and a compound comprising one or more P-O-P anhydride moieties, wherein said moieties comprise one P atom at the oxidation state (+111) and the other P atom at the oxidation state (+111) or (+V), to form N,N'-bis(phosphonomethyl)-2,5- diketopiperazine, its dehydrated forms or their phosphonate esters; b) hydrolyzing the reaction mixture to form N-(phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters and its phosphonate ester salts.
A01N 57/20 - Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
7.
METHOD FOR THE SYNTHESIS OF ALPHA-AMINOALKYLENEPHOSPHONIC ACID
The present invention is related to a new method for the synthesis of alpha-aminoalkylenephosphonic acid or its phosphonate esters comprising the steps of forming a reaction mixture by mixing a P-O-P anhydride moiety comprising compound, having one P-atom at the oxidation state (+111) and the other P-atom at the oxidation state (+111) or (+V), an aminoalkanecarboxylic acid and an acid catalyst, wherein said reaction mixture comprises an equivalent ratio of alpha-aminoalkylene carboxylic acid to P-O-P anhydride moieties of at least 0.2, and recovering the resulting alpha-aminoalkylene phosphonic acid compound or an ester thereof from the reaction mixture.
C07F 9/6524 - Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
A01N 57/20 - Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
C08F 8/40 - Introducing phosphorus atoms or phosphorus-containing groups
8.
METHOD FOR THE SYNTHESIS OF N-(PHOSPHONOMETHYL)GLYCINE
The present invention is related to a method for the synthesis of N- (phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters, or its phosphonate ester salts, which includes the steps of: • a) forming, in the presence an acid catalyst, a reaction mixture comprising 2,5- diketopiperazine, formaldehyde and a compound comprising one or more P-0-P anhydride moieties, said moieties having one P atom at the oxidation state (+ III) and the other P atom at the oxidation state (+III) or (+V), to form Ν,Ν'- bisphosphonomethyl-2,5-diketopiperazine, its mono- to tetra phosphonate esters, the dehydrated forms of Ν,Ν'- bisphosphonomethyl-2,5-diketopiperazine and the phosphonate esters of its dehydrated forms; • b) hydrolysing said N,N'-bisphosphonomethyl-2,5-diketopiperazine, its dehydrated forms or their phosphonate esters to obtain N- (phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters and its phosphonate ester salts.
A01N 57/20 - Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
The present invention is directed to a new method for esterification of P-O components. More specifically, the present invention relates to a new method for esterification of P-O components containing at least one P-O-H functional group, whereby the P-O-H functional group(s) is converted into P-O-R functional group(s). The method according tothe invention may find particular use in the manufacture of diesters of phosphorous acid.
A method for the manufacture of compounds containing an a-oxy phosphorus group is disclosed. A compound containing an a-oxy carboxylic acid group is reacted in a specific equivalent ratio with a nucleophilic P component, wherein the phosphorus atom has the oxidation state +1 or +3, whereby the compound containing an a-oxy carboxylic acid group or the nucleophilic P component or both are first reacted with an activator, followed by conducting the reaction and adding a water at the end of the reaction. The compounds containing an a-oxy phosphorus group formed are then recovered.
C07F 9/655 - Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
11.
METHOD FOR THE MANUFACTURE OF COMPOUNDS CONTAINING AN ALPHA-OXY PHOSPHORUS GROUP BY USING P-X COMPONENTS
A method for the manufacture of compounds containing an α- oxy phosphorus group is disclosed. A P-X component having at least one P-X bond, whereby the phosphorus of the P-X bond has the +3 oxidation state with X being C1 or Br, is reacted in a specific equivalent ratio with a compound containing an α-oxy carboxylic acid group, followed by conducting the reaction and optionally adding a quenching agent at the end of the reaction. The compounds containing an α-oxy phosphorus group formed are then recovered.
C07F 9/655 - Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
C07F 9/6571 - Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
C07F 9/6584 - Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
12.
METHOD FOR THE MANUFACTURE OF COMPOUNDS CONTAINING AN α-OXY PHOSPHORUS GROUP
A method for the manufacture of compounds containing an α-oxy phosphorus group is disclosed. A P-O component having at least one P-O-P moiety, whereby at least one phosphorus has the +3 oxidation state, is added in specific proportions to a compound containing an α-oxy carboxylic acid group, followed by conducting the reaction and adding water subsequently. The compounds containing an α-oxy phosphorus group formed can then be recovered.
An improved method for the manufacture of phosphonoalkyl iminodiacetic acid M2PO3-X-N- (CH2COOM) 2 wherein X is a C1-6 linear or branched alkyl group; and M is selected from hydrogen, alkali, earth-alkali, ammonium and protonated amine is disclosed. The iminodiacetic acid starting material is reacted with a substantially stoichiometric amount of phosphorous acid, in the presence of a large excess of phosphoric acid to thereby yield a reaction medium insoluble reaction product (PAIDA) which can be separated from the reaction medium. In a particularly preferred approach, the phosphorous acid is prepared in situ starting from liquid P4O6.
The technology of this invention concerns a method for the manufacture of hydroxy diphosphonic acids containing an amino moiety. The method specifically involves reacting a liquid P4O6 with an aminocarboxylic acid in the presence of a sulfonic acid. The aminocarboxylic acid is selected from 3 structurally different compounds. The amino hydroxy diphosphonic acids can be synthesized with high selectivity and purity and the unreacted starting raw materials can easily and conveniently be recirculated.
A method for the manufacture of aminoalkylene phosphonic acids broadly is disclosed. In the essence, an amine corresponding to a specific formula is reacted in aqueous medium with phosphorous acid and formaldehyde to thereby yield a medium insoluble reaction product. The insoluble product formed i.e. the aminoalkylene phosphonic acid can be separated, optionally washed, and recovered. This process yields high purity and selectivity reaction products. The excess phosphonic acid can be recycled into the processing sequence.
A method for the manufacture of aminopolyalkylene phosphonic acid of a specific general formula is described. In particular, a mixture of specifically defined ranges of reactants to wit: phosphorous acid; an amine; formaldehyde and an aminopolyalkylene phosphonic acid, having the same general formula as the compound to be manufactured, are reacted to thus yield a product of outstanding selectivity and purity with substantially reduced levels of non-desirable by-products.
A process for the manufacture of dialkyl phosphites is disclosed. In detail, dialkyl phosphites are prepared starting from P4O6, or partially hydrated species thereof cumulatively P-O, by reacting specific molar ratios of alcohol and P-O, containing from 1 to 6 P-O-P bonds in the molecule, in the presence of trialkylphospite (TAP) to thus yield high purity and high yield of dialkyl phosphites. The P-O reactant is preferably represented by liquid P4O6.
A method for the manufacture of dialkyl phosphites is disclosed wherein a P-O component containing from 1 to 6 P-O-P bonds in the molecule is reacted with an alcohol and a carboxylic acid ester having from 1 to 6 carbon atoms in the alkyl group and from 5 to 20 carbon atoms in the esterifying alkyl group of the ester. The dialkyl phosphites are formed under simultaneous removal by distillation of the carboxylic acid formed.
An improved method for the manufacture of phosphonoalkyl iminodiacetic acid (PAIDA) is disclosed. The iminodiacetic acid starting material is reacted with a considerable amount, in excess of stoichiometric requirements, of phosphorous acid to thereby yield a reaction medium insoluble reaction product which can be separated from the reaction medium. In a particularly preferred approach, the phosphorous acid is prepared in situ starting from liquid P4O6.
A method for the manufacture of dialkyl phosphites by reacting a P-O component containing from 1 to 6 P-O-P bonds in the molecule, with an alcohol and a ketal corresponding to a selected formula, said ketal will not lead to the formation of an enol structure. The level of the ketal is expressed in relation to the level of co-reactants. A preferred ketal is void of any carbon-hydrogen bonds on the α-carbon atom in the ketal structure.
A process for the production of a reaction product consisting essentially of P4O6 is carried out by reacting oxygen with phosphorus in an exothermic reaction in a reaction unit. Heat created by the exothermic reaction is removed by feeding P4O6 and/or by-products of the process into the reaction unit. The generated reaction product is then quenched to a lower temperature where no essential decomposition of the reaction product occurs, and at least part of P4O6 is separated from the reaction product obtained after quenching. The resulting yield of P4O6 based on the phosphorus used is improved and the heat of the exothermic reaction can be controlled in an economic way.
A method for the manufacture of concentrated phosphorous acid starting from pure P4O6 is disclosed. The P4O6 is hydro lysed, preferably under stirring in water in the presence of a homogeneous Broensted acid catalyst while maintaining in the hydrolysis/reaction medium a pH below 5 whereby the free water level, at the completion of the hydrolysis, is in the range from 0 to 40 %.
A method for the manufacture of amino alkylene phosphonic acids is disclosed. Pure P4O6 is hydrolyzed in the presence of a homogeneous Broensted acid catalyst whereby the pH of the reaction medium is maintained below 5 and the free water content of said reaction medium is, after the P4O6 hydrolysis has been completed, from 0 to 40 %. The required amine component can be added before, during, or in one preferred execution, after the P4O6 hydrolysis has been completed. Formaldehyde is then added and the reaction mixture containing the P4O6 hydrolysate, the amine and the formaldehyde is reacted in presence of a Broensted acid catalyst selected from homogeneous and heterogeneous species. The amino alkylene phosphonic acid reaction product can then be recovered in a manner known per sé.
The invention relates to a process for the production of P4O6 of high purity by reacting oxygen, or a mixture of oxygen and an inert gas, with gaseous or liquid phosphorus to generate said reaction product in a reaction unit. The reaction product is kept in the reaction unit at an average temperature in the range of 1600 and 2000 K by removing the heat created by the exothermicreaction of phosphorus and oxygen. A residence time of at least 1 second of the reaction product passing the reaction unit is maintained. The reaction product is then conventionally cooled in a quenching unit connected with the reaction unit. The final reaction product contains P4 O6 with a very low content of elemental phosphorus.
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