Method for production of o-(2-ethyl-n-hexyl)-o-(3,4,5-trithiatricyclo[5.2.1.02,6]-dez-8-yl-methyl)-dithiophosphoric 1-(n,n-dimethylaminomethyl)-1,2,4-triazole salt as lubricant oil additive

FIELD: synthesis of lubricant oil additives.

SUBSTANCE: method for production of O-(2-ethyl-n-hexil)-O-3,4,5-trithiatricyclo[5.2.1.02,6]-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of general formula

is disclosed. 1-(N,N-dimethylaminomethyl)-1,2,4-triazole is brought into reaction with equimolar amount of O-(2-ethyl-n-hexyl)-O-3,4,5-trithiatricyclo[5.2.1.02,6]-dez-8-yl-methyl)-dithiophosphoric acid in toluene medium at 80-100°C for 2-4 h.

EFFECT: ash-free antiscoring lubricant oil additive operating under high pressure.

2 tbl, 1 ex

 

The present invention relates to the field of synthesis of lubricating oil additives, in particular to a method for producing 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of O-(2-ethyl-n-hexyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)-dithiophosphoric acid of General formula (1), perspective as ashless additives to oils.

The specified connection formula (1) can be used as additives with enhanced extreme-pressure, anti-wear properties, high thermal and oxidative stability.

The known method [U.S. Pat. U.S. No. 4519928, CL 10 M 1/32, 1985] receiving lubricant additives of the General formula (2) alkylation of benzotriazole. The additive is injected in the amount of 1 wt.% in the lubricating oil to provide anti-oxidation and anti-corrosion properties.

where R is hydrogen or hydrocarbon With1-C12radical, R1and R2- C1-C4-alkyl, R3- C1-C12-alkyl.

In a known manner there can be obtained 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of O-(2-ethyl-n-hexyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)-dithiophosphoric acid (1).

The known method [A.m.kuliev “Chemistry and technology of additives to oils and fuels. M: “Chemistry, 1985, str] get ash when is ADCI DF-11 (zinc salt of O-(n-butyl)-O-(2-ethyl-n-hexyl)-dithiophosphoric acid), General formula (3), interaction paternostro phosphorus with isobutyl and isooctyl alcohols at 100-120°to dialkyldithiophosphoric acid, which is neutralized with 20°With zinc oxide.

The known method does not allow to obtain 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of O-(2-ethyl-n-hexyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)-dithiophosphoric acid (1). Furthermore, the way ash additive DF-11 has good antiwear and antioxidant properties, but the lack of extreme-pressure properties.

The purpose of the invention - creation method of producing ashless lubricant additives, operating at high pressures, in particular, additives for oils with improved extreme pressure properties.

The essence of the method lies in the interaction equimolar quantities of 1-(N,N-dimethylaminomethyl)-1,2,4-triazole with O-(2-ethyl-n-hexyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)-dithiophosphoric acid at a temperature of 80-100°C, preferably 90°C for 2-4 hours, preferably 3 hours Produced 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of O-(2-ethyl-n-hexyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)-dithiophosphoric acid (1) with the release of 92-100%.

Target product (1) is formed only with the participation aminomethylpropanol 1,2,4-t is iatola and O-(2-ethyl-n-hexyl)-O-(3,4,5-tritiated-cyclo[5.2.1.0 2,6]Oct-8-ylmethyl)-dithiophosphoric acid. In the presence of other aminomethylating products (for example, aminomethylating phenol or benzotriazol), other derivatives dithiophosphoric acid (for example, diarylethylene acid) of the target product (1) is not formed. Changing the ratio of initial reagents in the direction of increase or decrease of one of the components reduces the yield of the target product (1). The reaction was performed using toluene as solvent. In other solvents (e.g., aliphatic) decreases the yield of the target product (1).

The proposed method has the following advantages:

1. The method allows to obtain high yields ashless additive to lubricating oils of General formula (1), the synthesis of which is not described in literature.

The method is illustrated by the following examples:

EXAMPLE 1. In thermostated glass reactor fitted with mechanical stirrer, reflux condenser and a gas-feeding tube at room temperature (20-21° (C) the temperature in the atmosphere of nitrogen, was placed 100 mmol 1-(N,N-dimethylaminomethyl)-1,2,4-triazole and 100 mmol of O-(2-ethyl-n-hexyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)-dithiophosphoric acid in 30 ml of toluene, with stirring, heated to 90°and incubated for 3 hours, produce 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of O-(2-ethyl-n-Huck who yl)-O-(3,4,5-trimetrical[5.2.1.0 2,6]Oct-8-ylmethyl)-dithiophosphoric acid (1) with a yield of 96%.

The spectral characteristics of 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of O-(2-ethyl-n-hexyl)-O-(3,4,5-tritiated-cyclo[5.2.1.02,6]Oct-8-ylmethyl)-dithiophosphoric acid (1):

IR range (νcm-1): 562 (P=S), 675 (P=S), 740, 950 (R-O), 1010(P-O-S), 1238 (C-O), 1380, 1455, 2555. An NMR spectrum1N (δ, ppm, CDCl3TMS): 0.94 (m, 6N, CH3), 1.24 (m, 8H, CH2), 1.78-2.04 (m, 1H at C5), 2.65, 2.86 (s, 6N CH3), 3.25-4.18 (m, 6N, CH2Oh, CHS), 5.66 (s, 2H, NCH2N), 8.40, 8.06 (m, 2H, CH=N). An NMR spectrum13With (δ, ppm): 16.05 (1), 23.18 (2), 28.87 (3), 30.18 (With4) 39.80 (5), 72.59 (6), 23.18 (7), 10.92 (8), 69.04 (9), 40.62 (10), 42.51 (C11), 63.72 (12), 68.85 (13), 41.06 (14), 33.32 (15), 30.70 (16), At 41.48 (17With18), 71.32 (19), 143.18 (20), 151.43 (21). Found, %: C, 45.37; H, 7.26; S, 26.45; N, 9.64. C21H39S5PN4O2. Calculated, %: C, at 44.21; H, 6.84; S, 28.07, P, 5.44; N, 9.82;Oh, 5.82.

Other examples of the method are given in table 1.

Table 1
№ p/pThe reaction temperature, °Reaction time, hoursOutput (1), %
1.90 396
2.1003100
3.80392
4.904100
5.90294

The reaction was carried out at equimolar the ratio of initial reagents in toluene solution.

Additive (1)obtained according to examples 1-5 was dissolved in industrial oil AND 100A in the amount of 3 wt.% and compared their properties with known additive DF-11 (table 2).

Table 2

The results of the tests of the additive (1) in comparison with the known additive DF-11
IndexIndustrial oil AND-100A, ν50=St with 3% wt. additives
Additive (1)DF-11
Extreme-pressure properties determined according to GOST 9490-75 to-ball friction machine (CSM).  
Breaking load, kgf/cm21273741
The welding load, kgf315220
Anti-oxidant properties (72 hours at 120°feed 5 liters of air per hour, copper sheet), m is TOD TGL 17745. 3.94.5
Centrifuged sediment.0.10.1
Anti-corrosion properties according to GOST 2917-76.nono

As follows from table 2, obtained in accordance with the invention, 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of O-(2-ethyl-n-hexyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)-dithiophosphoric acid has in comparison with the known additive DF-11 (zinc salt of O-(n-butyl)-O-(2-ethyl-n-hexyl)dithiophosphoric acid) the best anti-wear properties, good compatibility with the base oil. In addition, they retain such performance properties of the additive DF-11, as anti-oxidant and anti-corrosion, consequently, are suitable additives to obtain oils of class TM-5 in accordance with TGL 21160. Additive DF-11 allows you to get the gear oil before class performance TM-3.

The way to obtain 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of O-(2-ethyl-n-hexyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)-dithiophosphoric acid formula

as additives to lubricating oils is that 1-(N,N-dimethylaminomethyl)-1,2,4-triazole interacts with equimolar number of O-(2-these is-n-hexyl)-O-(3,4,5-trimetrical[5.2.1.0 2,6]Oct-8-ylmethyl-)dithiophosphoric acid in the environment of toluene at a temperature of 80-100°C for 2-4 hours



 

Same patents:

FIELD: synthesis of lubricant oil additives.

SUBSTANCE: method for production of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of general formula

is disclosed. 1-(N,N-dimethylaminomethyl)-1,2,4-triazole is brought into reaction with equimolar amount of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid in toluene medium at 80-100°C for 2-4 h.

EFFECT: ash-free antiscoring lubricant oil additive operating under high pressure.

2 tbl, 1 ex

The invention relates to organophosphorus compounds and can be used to produce fire-resistant fluids used in the technological high pozharoopastnost, for example, control systems and lubrication of steam turbines power plants

The invention relates to the field of chemistry of organophosphorus compounds and can be used to produce fire-resistant hydraulic and lubricating fluids used in power, metallurgical, coal, machine building and other industries, for example in control systems and lubrication of steam turbines, hydraulic coal mining machines, hydraulic machines, injection molding etc

The working fluid // 2009185
The invention relates to the creation of vzryvopozharobezopasnost working fluid, designed for use in hydraulic systems of aircraft

The invention relates to lubricants, in particular for lubricants for coating metal surfaces

FIELD: synthesis of lubricant oil additives.

SUBSTANCE: method for production of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of general formula

is disclosed. 1-(N,N-dimethylaminomethyl)-1,2,4-triazole is brought into reaction with equimolar amount of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid in toluene medium at 80-100°C for 2-4 h.

EFFECT: ash-free antiscoring lubricant oil additive operating under high pressure.

2 tbl, 1 ex

The invention relates to new P,N-bidentate ligands of formula (I):

where a is S or NR,

where R represents a C1-C4alkyl,

R1and R2represent hydrogen, C1-C4alkyl, or R1and R2can be locked in the benzene ring,

R3and R4submit C1-C4alkyl or phenyl,

R5and R6submit C1-C4alkyl

The invention relates to new heteroaryl-alldifferent formulas (I) and (II) for compounds of formula (I) A=S if V=C; A=N, if B=N, R1is hydrogen or C1-C4alkyl, R2-R5-phenyl, R6and R7is hydrogen, n=0 or 1, R8-R11is hydrogen; compounds of f-crystals (II) A=N, if I=S, R1=C1-C4alkyl, A=C, if B= N, R1is hydrogen; A=N if I=N, R1=0; And=O, if=S, R1=0, R2-R5- phenyl, R8-R11is hydrogen or C1-C4alkyl

FIELD: synthesis of lubricant oil additives.

SUBSTANCE: method for production of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of general formula

is disclosed. 1-(N,N-dimethylaminomethyl)-1,2,4-triazole is brought into reaction with equimolar amount of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid in toluene medium at 80-100°C for 2-4 h.

EFFECT: ash-free antiscoring lubricant oil additive operating under high pressure.

2 tbl, 1 ex

FIELD: organic chemistry, pharmaceutical compositions.

SUBSTANCE: 5-aryl-1H-1,2,4-triazole derivatives of general formula I

, pharmaceutically acceptable salts thereof or pharmaceutical composition containing the same are described. In formula R1 is C1-C6-alkyl, C1-C6-haloalkyl or phenyl; R2 is C3-C8-cycloalkyl; phenyl optionally substituted with one or more substituents selected from C1-C4-alkyl; halogen, hydroxyl, C1-C4-alkoxy, nitro, di-(C1-C4)-alkylamino, C1-C4-alkylsulphonyl, C1-C4- alkylsulphonylamino, and methylenedioxy; phenyl-(C1-C4)-alkyl, wherein phenyl is substituted with C1-C4-alkoxy; or pyridil. New compounds are effective and selective cyclooxygenase-2 (COX-2) inhibitors and useful in treatment of inflammations.

EFFECT: new compounds for inflammation treatment.

10 cl, 36 ex, 1 tbl

The invention relates to the chemistry of heterocyclic compounds, namely to substituted 1-(pyridinyl-3)-2-azolylmethyl General formula I

where R means a hydrogen atom, an unbranched or branched alkyl with a number of carbon atoms of from one to eight, cycloalkyl with the number of carbon atoms from three to eight, cycloalkenyl with the total number of atoms from four to ten, alkylsilanes with the total number of atoms from four to ten, X denotes a nitrogen atom or CH group, which possess fungicidal activity and can be used as agricultural, industrial, medical or veterinary fungicides

The invention relates to substituted 3,5-diphenyl-1,2,4-triazole and their use as pharmaceutical agents, which form chelate complexes with metal

The invention relates to aryl - and getelemen carboalkoxylation acids of formula 1

< / BR>
where R1selected from the group of arrow or getarrow, R2selected from the group of Akilov

The invention relates to medicine, specifically to pharmaceutical technology, namely the method of production of drugs having antifungal activity of fluconazole

The invention relates to medicine, specifically to pharmaceutical technology, namely the method of production of drugs having anti-fungal action - fluconazole

FIELD: organic chemistry, pharmaceutical compositions.

SUBSTANCE: 5-aryl-1H-1,2,4-triazole derivatives of general formula I

, pharmaceutically acceptable salts thereof or pharmaceutical composition containing the same are described. In formula R1 is C1-C6-alkyl, C1-C6-haloalkyl or phenyl; R2 is C3-C8-cycloalkyl; phenyl optionally substituted with one or more substituents selected from C1-C4-alkyl; halogen, hydroxyl, C1-C4-alkoxy, nitro, di-(C1-C4)-alkylamino, C1-C4-alkylsulphonyl, C1-C4- alkylsulphonylamino, and methylenedioxy; phenyl-(C1-C4)-alkyl, wherein phenyl is substituted with C1-C4-alkoxy; or pyridil. New compounds are effective and selective cyclooxygenase-2 (COX-2) inhibitors and useful in treatment of inflammations.

EFFECT: new compounds for inflammation treatment.

10 cl, 36 ex, 1 tbl

FIELD: synthesis of lubricant oil additives.

SUBSTANCE: method for production of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of general formula

is disclosed. 1-(N,N-dimethylaminomethyl)-1,2,4-triazole is brought into reaction with equimolar amount of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid in toluene medium at 80-100°C for 2-4 h.

EFFECT: ash-free antiscoring lubricant oil additive operating under high pressure.

2 tbl, 1 ex

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