Furifosmin, organometallic complexes based on them, methods for their production and catalysts

 

(57) Abstract:

The invention relates to new furifosmin formula I

< / BR>
where n denotes an integer of 1 or 2; R1denotes a hydrophilic group selected from the following groups: -SO2M, -SO3M, -CO2M, -PO3M, where M represents inorganic or organic cationic residue selected from a proton, cations, alkaline or alkaline earth metals, ammonium cations -- N(R)4where R denotes hydrogen or C1-C14alkyl, and the other cations are based on metals, salts with acids: fullsleeve, fullcarbon, fullsleeve or furylphosphonous soluble in water; m denotes an integer of 1; R2denotes a hydrophilic group,- SO2M, -SO3M, -CO2M, RHO3M, where M denotes hydrogen or an alkaline metal salt with the acid fullsleeve, fullcarbon, fullsleeve or fullfactorial soluble in water, R denotes an integer from 0 to 2. The compounds of formula I form ORGANOMETALLIC complexes with transition metals of the 8th group of the Periodic system of elements, which can be used as catalysts for chemical reactions: HYDROFORM is in and reduction of compounds, isomerization and hydrocyanide olefins. 5 S. and 2 C.p. f-crystals, 5 PL.

The invention relates to new water-soluble furifosmin.

The invention relates to ORGANOMETALLIC complexes containing these furifosmin, and to the use of these complexes.

The unsubstituted triphenylphosphine described in article V. Farina and C. Krishnan, published in the Journal of American Chemical Society, 1991, 113, R. 9585-9595. According to this article the system containing triphenylphosphine have remarkable catalytic activity.

To date not been described water-soluble furifosmin, such as those that are the subject of the present invention.

New water-soluble furifosmin correspond to the General formula I

< / BR>
in which n denotes an integer from 1 to 3;

- at least one radical R2denotes a hydrophilic group, such as:

-SO2M, -SO3M, -CO2M, RHO3M, where M represents inorganic or organic cationic residue selected from a proton, cations based on alkali or alkaline earth metals, ammonium cations -- N(R)4where R are identical or different, denote a hydrogen atom or the radical ALK is, fullcarbon, fullsleeve or furyl-phosphonic soluble in water;

-N(R)3X, where R, identical or different, denote a hydrogen atom or an alkyl radical with 1-12 carbon atoms, and X denotes an organic or inorganic anion;

-HE;

- R1denotes a hydrophilic group, such as defined for R2or a group of alkyl or alkoxy with 1-12 carbon atoms, halogen atom, nitrile group or halogenation group with 1-12 carbon atoms;

- m is 1 or 2;

p is an integer from 0 to 3;

when m is 2, the radical R2can be alkyl or alkoxygroup having 1-12 carbon atoms, a halogen atom, nitrile group or halogenoalkanes group with 1-12 carbon atoms.

The term "water-soluble" or "water-soluble" in this text assume the connection, the solubility of which is equal to at least 0.01 g in 1 l of water.

Water-soluble furifosmin of the present invention are often compounds of General formula I, in which:

n denotes an integer from 1 to 3;

- R2denotes a hydrophilic group such as-SO2M, -SO3M, -CO2M, RHO3M, where M hereafter is or alkaline earth metals, ammonium cations -- N(R)4in the formula where R, identical or different, denote a hydrogen atom or an alkyl radical with 1-4 carbon atoms, and other cations are based on metals, salts with acids: fullsleeve, fullcarbon, fullsleeve or furylphosphonous, soluble in water;

- m is 1 or 2;

- R1denotes a hydrophilic group, such as defined for R2or Deputy-N(R)3X in the formula which R, identical or different, denote a hydrogen atom or an alkyl radical with 1-4 carbon atoms and X denotes an organic or inorganic anion, Deputy-HE, Deputy alkyl or alkoxy having 1-4 carbon atoms, halogen atom, nitrile or triptorelin group;

p denotes an integer from 0 to 2.

The object of the present invention is also getting a new water-soluble furifosmin. The latter is obtained, usually from their precursor such as diphenyl-furifosmin or phenyl-diphenylphosphine or triphenyl-phosphine, are not substituted by hydrophilic groups. Getting furifosmin consists in the introduction in foreline cycles hydrophilic groups R2and possibly the introduction of a phenyl cycles is inorganically compounds, organic part which corresponds to the compound of General formula I, not containing substituents R2and which is connected to the lithium atom through its or their foreline cycles, the electrophilic center of the precursor of the radical R2such as sulfur dioxide, carbon dioxide, alkylphosphate, sulfonates pyridine or sulfonates trialkylamine.

Very organolithium compound is produced by the action of lithium base (for example, utility) furifosmin predecessor.

In relation to obtaining furifosmin precursor can, for example, to refer to the work of A. J. Zapata and A. C. Randon in Org. Prep. Proced. Int. 27, 5 (1995), page 567 and later.

Water-soluble furifosmin give the opportunity to get ORGANOMETALLIC complexes containing at least one water-soluble furifosmin formula I and at least one metal.

Metals that can be used to form complexes with water-soluble furifosmin represent in the General case, the transition metals of groups 1b, 2b, 3b, 4b, 5b, 6b, 7b and 8 of the periodic system of elements of this type, which was published in the "Handbook of Chemistry and Physics, 51st Edition (1970-1971) by The Chemical Rubber Company.

Satarov chemical reactions. As not limiting the scope of invention examples can be mentioned Nickel, cobalt, iron, ruthenium, rhodium, palladium, osmium, iridium, platinum, copper, silver, gold, zinc, cadmium, mercury.

Getting ORGANOMETALLIC complexes containing water-soluble furifosmin, can be carried out by bringing into contact a solution of the compound of the selected metal with an aqueous solution of water-soluble furifosmin formula I.

The compound of the metal may be dissolved in water or in an organic solvent, which in turn can be mixed or not mixed with water.

The oxidation state of the metal used in the connection can be either the same kind of metal will be composed of ORGANOMETALLIC complex or higher.

As an example, you can specify that in the ORGANOMETALLIC complexes of the invention, rhodium is the oxidation state 1, the oxidation state of the ruthenium - 2, the oxidation number of platinum - 1 oxidation of palladium - 2, the oxidation state of osmium - 0, the degree of oxidation of iridium - 0 and the oxidation state of Nickel is 0.

If the preparation of the ORGANOMETALLIC complex is used a metal with a higher degree of akissforjersey formula I, can be used as catalysts for chemical reactions.

In two-phase aqueous catalysis of the water-soluble furifosmin experience a positive synergistic effect caused by natural hydrophilicity fueling cycle and hydrophilic radicals R2. Due to this, the solubility of furifosmin in water is very high.

As chemical reactions catalyzed by ORGANOMETALLIC complexes containing water-soluble furifosmin formula I, can, for example, to call hydroformylation and hydrocarbonylation olefins in the presence of rhodium complexes, hydrogenation of olefins, aldehydes, acids, enamides and reduction of compounds in the presence of complexes of ruthenium, rhodium, platinum or palladium, telomerization dienes, isomerization of olefins, dimerization of ethylene and Acrylonitrile, hidrotsianova olefins in the presence of complexes of Nickel, the synthesis of furan in the presence of complexes of ruthenium, the disproportionation of olefins in the presence of complexes of ruthenium, the polymerization of acrylates in the presence of complexes of Nickel or of combination reaction type carbon-carbon such as, for example, as a reaction the Heck or Suzuki in the presence of complexes n is erinacei NITRILES, received by hidrotsianova dienes, and, in particular, in the reaction of isomerization of 2-methyl-3-butene-nitrile 3-penten-nitrile. This reaction is of great industrial importance in the production process adiponitrile. The latter is an important synthetic intermediate, in particular in the production of monomers for polyamides such as caprolactam or hexamethylenediamine were.

The invention is illustrated by the following examples.

EXAMPLES 1-4: Synthesis of water-soluble furifosmin formula I EXAMPLE 1: 2-(diphenylphosphino)furyl-5-carboxylate sodium

In purged with nitrogen, 500-ml chetyrehosnuju flask equipped with addition funnel with a balanced pressure ball refrigerator, mechanical stirrer and thermometer, download 30,3 ml (47 mmol) of n-utility (to a concentration of 1.55 M), then quickly insert of 6.4 ml (42 mmol) of tetramethylaniline (TMD) in 50 ml of purged with nitrogen anhydrous diethyl ether. Added dropwise 10,65 g (of 42.3 mmol) diphenylphosphine, previously dissolved in 50 ml of anhydrous ethyl ether, purged with nitrogen, allowing the passage of the exothermic reaction to the 35oC. the Mixture takes on an orange color.

After stirring for 15 m is Alenia of phosphine.

After this refrigerator to replace a tube that allows you to move the solution dropwise into the Dewar vessel with solid carbon dioxide, immersed in approximately 200 ml of purged with nitrogen anhydrous diethyl ether. Anion immediately forms a white precipitate. The mixture is left overnight in the open air. The suspension of the white solid in the air take 100 ml of a saturated solution of Panso3and the resulting mixture is extracted. The ether phase is twice extracted with 30 ml obezvozhennoy water. The aqueous phase are combined acidified in the cold with small portions 12 N. Hcl until neutral pH. The resulting aqueous phase is shaken out three times with 50 ml dichloromethane. The organic phases are combined and add to them for 1.49 g of soda, dissolved in a few ml of water. After evaporation of the solvents to obtain a viscous yellow-brown oil, which after some rubbing and leaching of anhydrous diethyl ether followed by drying in vacuum at 90oWith turns into a fine white powder. Get 11,44 g (36 mmol) of the target product. Yield 85%.

The product has the following characteristics:

NMR31P (D2O):=25,1

NMR1H (D2O):=of 6.20 (d, 1H,3JNN=3,2, C3N); =for 6.81 (m, 1H ); = 7,06 (m, 10H, Ah)

-3JCF=19,7, ); =136,8 (d1JCFcf= 4,4, Cipso); =156,4 (C ); =156,9 (d1JCF=13,7, ); =168,1 (C ).

The solubility of this furifosmin water is 250 g/l at 23oC.

EXAMPLE 2: 2-(diphenylphosphino)furyl-5-phosphonate disodium

In purged with nitrogen, 500-ml chetyrehosnuju flask equipped with addition funnel with a balanced pressure ball refrigerator, mechanical stirrer and thermometer, loads of 33.8 ml (52 mmol) of n-utility (to a concentration of 1.55 M), then quickly insert of 6.4 ml (42 mmol) of TMD in 50 ml of purged with nitrogen anhydrous diethyl ether. Then added dropwise 12,32 g (48,9 mmol) diphenylphosphine, pre-dissolved in 40 ml of purged with nitrogen anhydrous diethyl ether. In the exothermic reaction the temperature of the mixture rises spontaneously to 35oWith the mixture takes on an orange color.

After stirring for 15 min in a stream of nitrogen appreciate using NMR31R the formation of the anion, which is completed within 15 min after addition of phosphine.

The reaction mixture is cooled to -70oWith and replace the tube refrigerator. The solution is transferred dropwise in the second chetyrehpolnye of readinglist, dissolved in 20 ml of anhydrous diethyl ether. The mixture is allowed to cool to room temperature, followed by hydrolysis in situ with 100 ml of an aqueous solution of ammonium chloride and extracted three times with 50 ml diethyl ether. The combined organic phases, dried over magnesium sulfate, filtered and evaporated, obtaining 20 g of a brown-yellow oil. The latter is heated at 100oWith under a pressure of 10-2mm RT.article (1.3 PA) in the ball of the furnace in order to remove phosphates. Receive and 17.2 g of a viscous yellow-brown oil, which is then chromatographic 10 ml of silica gel, using as additionally separated by a mixture of ethyl acetate/hexane (50/50). After evaporation of the solvents to obtain 14.2 g colored oil, which is placed in a solution of 60 ml of dichloromethane and stirred overnight with a magnetic stirrer in the presence of 10 ml (74 mmol) of bromotrimethylsilane. The reaction is exothermic, the observed discoloration of the medium. After evaporation of the solvents the product take 60 ml of acetone and 2 ml of distilled water. After 2 h 30 min, the solvents evaporated and the product take a minimal amount of methanol, where the cooling and mixing of the injected 3.04 from g 40% aqueous soda solution, result>With the vacuum. The yield of the desired product is 54%.

The product has the following characteristics:

NMR31P (D2O):=28,2; d=0,8 (P=0)

NMR1H (D2O):=6,72 (m, 2H, ); =7/41 (m, 10H, Ah)

NMR 13WITH (D2O):=117,9 (DD,4JCF=4,67,3JCF=20,0, ); =124,6 (DD, JCF= 3,5, JCF=21,0,4N); =131, 6mm (d3JCF=7,5, ); =132,2 (C ); = br135.8 (d2JCF= 19,2, ); =137,8 (C ); =155,4 (DD, JCF=7,4, JCF=10,4, ); =165,1 (d1JCF=199,0, ).

The solubility of this furifosmin is 680 g/l at 20oC.

EXAMPLE 3: 2,2'-phenylphosphine-bis(furyl-5-phosphonate) disodium

In purged with nitrogen, 500-ml chetyrehosnuju flask equipped with addition funnel with a balanced pressure ball refrigerator, mechanical stirrer and thermometer, download 42 ml (65 mmol) of n-utility (to a concentration of 1.55 M) g then quickly introduced to 9.15 ml (60 mmol) of TMD in 50 ml of purged with nitrogen anhydrous diethyl ether. Then added dropwise to 4.41 ml (60,0 mmol) of furan, pre-diluted with 40 ml of purged with nitrogen anhydrous diethyl ether. In the exothermic reaction the temperature of the mixture rises spontaneously within 30 min plan of 4.2 ml (30 mmol) of dichlorophenylphosphine, dilute 20 ml of ether. Controlling with the help of NMR31P the formation of the product, raise the temperature to room to enter to 9.15 ml (60 mmol) of TMD in 50 ml of diethyl ether, and then quickly poured 42 ml (65 mmol) of n-utility (to a concentration of 1.55 M). After stirring for 15 min in a stream of nitrogen was determined by NMR31P the formation of the anion. The formation of the anion ends in 15 minutes after the addition of phosphine.

The reaction mixture is cooled to -70oWith and replace the tube refrigerator. The solution is transferred dropwise in the second chetyrehpolnye reactor, equipped with the same equipment as the first cooled to -60oWith and containing 8,95 ml (60 mmol) of diethylphosphate dissolved in 20 ml of anhydrous diethyl ether. The mixture is allowed to cool to room temperature, followed by hydrolysis in situ with 100 ml of an aqueous solution of ammonium chloride and extracted three times with 50 ml diethyl ether. The combined organic phases, dried over magnesium sulfate, filtered and evaporated, obtaining 20 g of a brown-yellow oil. The latter is heated at 100oWith under a pressure of 10-2mm RT. Art. (1.3 PA) in the ball of the furnace in order to remove phosphates. The product then the HRO shall fastin and monophosphorylated connection. After evaporation of the solvents to obtain 3.5 g of product (yield 23%). The entire sequence of operations is repeated once more to obtain the product in a quantity sufficient for the continuation of the synthesis.

8,55 g (of 16.6 mmol) dephosphorylating connection left overnight in the form of a solution in 50 ml of dichloromethane, mixed with a magnetic stirrer in the presence 9,43 ml (70 mmol) of bromotrimethylsilane. Is exothermic reaction, in which the environment becomes colourless. After evaporation of the solvents the product take 50 ml of acetone and 2 ml of distilled water. After 2 h 30 min, the solvents evaporated and the product take a minimal amount of methanol, where the cooling and mixing of the injected 2.8 g of 40% aqueous soda solution, resulting in the coloration of the medium changes from yellow to brown. The solvents are evaporated and the resulting orange solid is triturated, washed with acetone, filtered and dried at 100oWith the vacuum. Obtain 6.7 g of whitish target product with a yield of 82% (calculated on dephosphorylating connection).

The product has the following characteristics:

NMR31P (D2O):=49,5; d=0,0 (P=0)

NMR1H (D2O):=6,67 (m, 2H, ); =to 6.80 (m, 2H, C3N); =7,41 THE= 18,3, ); =to 131.4 (d,3JCF=7,0, ); =131,9 (C, Cpair); =134,7 (d2JCF= 19,0,ortho); =136,9 (C, Cipso); =153,5 (d1JCF=7,3, JCF=10,4, ); =164,5 (d1JSRO=199,5, ).

The solubility of this furifosmin is 1140 g/l at 23oC.

EXAMPLE 4: 2-(diphenylphosphino)-furyl-5-sulfinic sodium

In purged with nitrogen, 500-ml chetyrehosnuju flask equipped with addition funnel with a balanced pressure, double ball refrigerator (with water and silicone oil), a stirrer and a thermometer, loads of 26.3 ml (40 mmol) of n-utility (to a concentration of 1.52 M), and then poured dropwise 10,65 g (of 42.3 mmol) diphenylphosphine, previously dissolved in 50 ml of purged with nitrogen anhydrous diethyl ether, during which the temperature rises due to the exothermic reaction to the 30oWith the mixture takes on a yellow color.

After stirring for 45 min in a stream of nitrogen appreciate using NMR31P the formation of the anion. The reaction mixture is cooled to -60oWith and replace the current nitrogen current of sulphur dioxide. Appears white precipitate, then the mixture turns yellow and then brown. Proceeds exothermic reaction. Then re what type of in situ 100 ml of degassed water, stir the mixture for 1 hour and extracted three times with water. The aqueous phase unite, cooled in an ice bath and acidified with 10 ml of 3 N. Hcl in the presence of 100 ml of dichloromethane, resulting in a yellow color disappears. After that three times quickly extracted with dichloromethane, combine the organic phases and add to cold under stirring with a magnetic stirrer 1.2 g of soda. The solvents are evaporated in vacuum, preventing the rise of temperature above 40oC. Get 6,86 g (20.3 mmol) of the desired product (white solid) in 51% yield.

The product has the following characteristics:

NMR31P (D2O):=26,7

NMR1H (D2O):=6,40 (m, 1H ); =6,53 (m ); =7,06 (m, 10H, Ah)

NMR13WITH (D2O):=111,6 (,), =124/8 (m ); =RB 131.1 (d,3JCF= 7,0, Cmeta); =131,7 (C, Cpair); =135,5 (d 2JCF=19,4,ortho); =136,8 (d1JCF=2,9, Cipso); =156,5 (l, JCF=16,5, ); =USD 170.1 (C, C2N).

The solubility of this furifosmin in water is 205 g/l at 21oC.

EXAMPLES 5-13: Obtain metal complexes with water-soluble furifosmin formula I and the use of these complexes as hydrogenation catalysts

The process is carried out in a 50 ml autoclave the LEM for the supply of gas and a valve for entry of the liquid.

First get different complexes with rhodium (examples 5-8), which are then used as catalysts for the hydrogenation of Z-acetamidocinnamic acid (examples 9-13).

Obtaining complexes with rhodium is stirring for 10 h in an argon atmosphere dissolved in 2 ml of water, 0.05 mmol one obtained in examples 1-4 water-soluble furifosmin with a solution of 0.025 mmol [Rh(COD)2] PF6-(COD denotes cyclooctadiene). After you change the color of the medium from orange to yellow, conduct comparative analysis using NMR31P.

Table 1 summarizes characteristics of the obtained complexes with rhodium.

In an autoclave using a syringe injected obtained above complex and then the solution 0,410 g (2 mmol) of Z--acetamidocinnamic acid in 30 ml of methanol and water (volume relationship of 1:1 or 1:2).

The mixture retains its homogeneity.

Set pressure 3 to 4 bar (0.3-0.4 MPa) of hydrogen and stirred the mixture for the time-dependent nature of furifosmin and gas absorption (see table 2). At the end of the experiment after degassing the reaction mixture is evaporated to dryness and analyzed by NMR1H in dimethyl sulfoxide - d6.

In table Plex to gidriruemyi substrate in %, the hydrogen pressure, the duration of the process) and the results (the degree of conversion of the substrate).

EXAMPLES 14-16: Obtain metal complexes with water-soluble furifosmin formula I and the use of these complexes for hydroformylation styrene

Obtaining complexes

Pre-receive ORGANOMETALLIC complex, adding dropwise furifosmin formula I, dissolved in 1 ml of water, the metal precursor [Rh(CO)2Cl]2or [Rh(CO)2ASAS], where the abbreviation "ASAS" represents acetylacetonate dissolved in either 1 ml of acetone (option "a" in table 3), which leads to the formation of a homogeneous environment, or in 1 ml of toluene (option "b" in table 3), which leads to the formation of heterogeneous (two-phase) environment.

When working with a heterogeneous environment, see the transition of the yellow color from the organic phase to the aqueous phase and thereby obtain a clear solution.

When working with homogeneous medium, the metal part periostat in the form of green needles with a metallic tinge, while the environment yellowish colored, and in some cases black.

Use as a precursor dimer [Rh(CO)2Cl]2trebuet NMR31R. at room temperature. All these complexes have a range with a broadened peak (characteristic of complex formation with rapid ligand exchange), characterized by a chemical shift of -10 to +20 m D. depending on the phosphine.

Hydroformylation styrene

Purge with nitrogen 250-ml autoclave equipped with a magnetic bar, safety valve, pressure gauge and two valves for the supply of gas. Using a pipette sequentially injected into a stream of nitrogen toluene and pre obezvozhennoy distilled water and then the catalyst (ORGANOMETALLIC complex).

There were two variants of experience:

- option (a) with 8 ml of water, 8 ml of toluene and 2 g of styrene, on the one hand, and with 1 ml acetone, 1 ml of distilled water, 0.08 mmol of rhodium and 0.08 mmol of furifosmin, on the other hand;

- option (b) with 2.5 ml water, 2.5 ml of toluene and 1 g of styrene, on the one hand, and with 1 ml of toluene, 1 ml of distilled water, 0.04 mmol of rhodium and 0.08 mmol of furifosmin, on the other hand.

Install a pressure of 10 bar (1 MPa) of carbon monoxide and 10 bar (1 MPa) of hydrogen. Heat the mixture at temperatures ToWith intensive stirring with a magnetic stirrer for 18 hours.

After the release of the ecografia. The results are shown in table 3: output of the aldehyde and the ratio of branched to linear aldehyde to the aldehyde (Ar/al).

EXAMPLES 17-26: Obtain metal complexes with different ligands in reactions of carbon-carbon combinations in the aquatic environment (reaction Hake)

In equipped with a magnetized bar of the tube Slinka in nitrogen atmosphere enter:

2 mmol (0,42 g) odensala,

3 mmol (0,30 g) acrylate,

3 mol (0.31 g) and triethylamine

3 ml of acetonitrile.

To the mixture of 0.05 mmol (11.2 g) PD(O2CLO3and then phosphine ligand (0.15 mmol) dissolved in 0.5 ml of water.

The mixture is heated to the desired temperature with vigorous stirring for homogenization of the environment.

Upon completion of the reaction solution is filtered and transferred into a separating funnel.

After several washes with water and diethyl ether, the resulting compounds are extracted with ether.

After evaporation of the solvents get a brown oil.

The degree of transformation of odensala determined by PMR analysis of the obtained brown oil.

The nature of the used ligands, temperature and reaction time are listed in table 4. matter of different ligands:

- Ligand As: 2,2'-phenylphosphino-bis (furyl-5-sulfinic lithium),

The ligand 2-(diphenylphosphino)-furyl-5-disodium phosphonate,

Ligand: 2-(diphenylphosphino)-furyl-5-carboxylate sodium,

Ligand D: 2,2'-phenylphosphino-bis (furyl-5-carboxylate lithium),

- Ligand E: mettepenningen trisulfonic sodium (known ligand).

From table 4 it follows that the ligands of the present invention can achieve the conversion of odensala at lower temperatures down to room temperature.

EXAMPLES 27-29: Obtain metal complexes with different ligands in the reaction of isomerization of 2-methyl-3-butene-nitrile (SBN) 3-penten-nitrile (PN)

In equipped with a magnetized bar of the tube Slinka in the atmosphere of argon injected 1.5 g of an aqueous solution of water-soluble ligand L, the concentration of which is expressed in mmol/kg

Add 5 g of 2-methyl-3-butene-nitrile and then 40-45 mg of bis(1,5-cyclooctadiene)Nickel(0) to achieve in the mixture the molar ratio ligand/Nickel, equal to 4.5. The temperature of the stirred mixture is brought to 90oC and maintained for 3 hours After cooling, the reaction mass is dissolved in acetone and analyzed by gas chromatography to determine the present organization is retene, presented in table 5.

The ligands of the invention provide a higher degree of transformation of 2-methyl-3-butene-nitrile with good selectivity for 3-penten-nitrile.

Examples 25C, 26C and 29s in tables 4 and 5 are comparative examples with known ligands.

1. Furifosmin formula I

< / BR>
where n denotes an integer of 1 or 2;

R1denotes a hydrophilic group selected from the following groups: -SO2M, -SO3M, -CO2M, RHO3M, where M represents inorganic or organic cationic residue selected from a proton, cations based on alkali or alkaline earth metals, ammonium cations -- N(R)4in the formula where R, identical or different, denote a hydrogen atom or an alkyl radical with 1 to 14 carbon atoms, and other cations are based on metals, salts with acids: fullsleeve, fullcarbon, fullsleeve or furylphosphonous soluble in water;

m denotes an integer of 1;

R2denotes a hydrophilic group selected from the following groups: -SO2M, -SO3M, -CO2M, RHO3M, where M denotes hydrogen or an alkaline metal salt with the acid: fenilsulfonil is from 0 to 2.

2. The method of producing furifosmin under item 1, involving the condensation of organolithium compounds, organic part which corresponds to the compound of General formula I, containing no substituent R2with the connection, which is a precursor of the radical R2selected from the group consisting of sulfur dioxide, carbon dioxide or alkylphosphates, with subsequent treatment of the resulting product with an alkaline agent.

3. ORGANOMETALLIC complexes, which contain water-soluble furifosmin under item 1 and the transition metal of the 8th group of the Periodic system of elements.

4. Complex on p. 3, characterized in that it contains a metal selected from the group consisting of Nickel, cobalt, iron, ruthenium, rhodium, palladium, osmium, iridium, platinum.

5. The method of obtaining ORGANOMETALLIC complexes under item 3 or 4, characterized in that a solution of the compound of the metal is injected into contact with an aqueous solution of water-soluble furifosmin formula I.

6. The method according to p. 5, characterized in that the compound of the metal dissolved in water or in an organic solvent which can be mixed or not mixed with water.

7. The catalyst chemical reach aldehydes, acids, enamides and reduction of compounds, isomerization of olefins, hydrocyanide olefins, characterized in that it contains the ORGANOMETALLIC complex under item 3 or 4.

 

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