Method for production of o-(n-butyl)-o-(3,4,5-trithiatricyclo(5.2.1.02,6)dez-8-yl-methyl))-dithiophosphoric acid 1-(n,n-dimethylaminomethyl)-benzotriazol salt as lubricant oiliness addend

FIELD: synthesis of lubricant oiliness addends.

SUBSTANCE: claimed method includes reaction of equimolar amounts of 1-(N,N-dimethylaminomethyl)-benzotriazol and O-(n-butyl)-O-(3,4,5-trithiatricyclodez-8-yl-methyl))-dithiophosphoric acid at 80-100°C in toluene medium for 2-4 h to produce target product of general formula:

.

EFFECT: ash-free addend for lubricant oils processing under high pressure, in particular lubricant oiliness addend of improved antiscoring properties.

2 tbl, 1 ex

 

The alleged invention relates to the field of synthesis of lubricating oil additives, in particular to a method for producing 1-(N,N-dimethylaminomethyl)-benzotryazolyl salt of O-(n-butyl)-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, C1-C12radical, R1and R2- C1-C4-alkyl, R3- C1-C12-alkyl.

In a known manner there can be obtained 1-(N,N-dimethylaminomethyl)-benzotryazolyl salt of O-(n-butyl)-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 perches and 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)-benzotryazolyl salt of O-(n-butyl)-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)-benzotriazole with O-(n-butyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)dithiophosphoric acid at a temperature of 80-100°C, preferably 90°With, for 2-4 hours, preferably 3 hours. Formed 1-(N,N-dimethylaminomethyl)benzotryazolyl salt of O-(n-butyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)dithiophosphoric acid (1) with the release of 91-100%.

Target product (1) is formed only with the participation aminomethylpropanol benzotriazole and O-(n-Buti is)-O-(3,4,5-trimetrical[5.2.1.0 2,6]Oct-8-ylmethyl)dithiophosphoric acid. In the presence of other aminomethylating products (for example, aminomethylating phenol or 1,2,4-triazole), 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:

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 nitrogen atmosphere is placed 100 mmol 1-(N,N-dimethylaminomethyl)-benzotriazole and 100 mmol of O-(n-butyl)-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)benzotryazolyl salt of O-(n-butyl)-O-(3,4,5-Tricia riciclo[5.2.1.0 2,6]Oct-8-ylmethyl)dithiophosphoric acid (1) with a yield of 98%.

The spectral characteristics of 1-(N,N-dimethylaminomethyl)-benzotryazolyl salt of O-(n-butyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)dithiophosphoric acid (1)

IR range (νcm-1): 560 (P-S), 670 (P=S), 738, 952 (P-O), 1005(-O-C), 1210 (C-O), 1380, 1455, 2858, 2920, 2938. An NMR spectrum1N (δ, ppm, CDCl3TMS): 0.98 (t, 3H, CH3), 1.29 (m, 4H, C2With3), 2.68, 2.80 (s, 6N, when C13C14), 3.28-4.20 (m, 6N, CH2Oh, CH-S), 5.63 (s, 2H, NCH2N), 7.28-7.96 (m, 4H, CH=CH). An NMR spectrum13With (δ, ppm): 14.08 (1), 19.10 (2), 34.53 (3), 68.66 (4), 69.23 (5), 40.65 (C6), 42.57 (7), 63.35 (8), 64.84 (9), 41.02 (10), 33.28 (C11), 30.74 (C12), 41.57 (13With14), 71.22 (15), 133.18 (16), 109.96 (17), 129.10 (18), 125.08 (19), 120.62 (20), 145.53 (C21). Found, %: C 46.12; N, 5.98; S 27.63; N 9.46.

C21H33S5PN4O2. Calculated, %: 44.68; H 5.85; S 28.37; P 5.50; N, 9.93; 5.67.

Other examples of the method are given in table 1.

Table 1
№ p/pThe reaction temperature, °Reaction time, hoursOutput (1),%
1.903/td> 98
2.1003100
3.80391
4.904100
5.90297

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 its properties with known additive DF-11 (smfbl).

As follows from table 2, obtained in accordance with the invention, 1-(N,N-dimethylaminomethyl)-benzotryazolyl salt of O-(n-butyl)-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)-benzotryazolyl salt of O-(n-butyl)-O-(3,4,5-trimetrical[5.2.1.02,6]Oct-8-ylmethyl)dithiophosphoric acid formula

as additives for lubricating oils, consisting in the fact that 1-(N,N-dimethylaminomethyl)-benzotriazol interacts in equimolar number of O-(n-butyl)-O-(3,4,5-trimetrical[5.2.1.02,6]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-(2-ethyl-n-hexil)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-benzotriazole salt of general formula 2 is disclosed. 1-(N,N-dimethylaminomethyl)-benzotriazole is brought into reaction with equimolar amount of O-(2-ethyl-n-hexyl)-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: 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

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-(2-ethyl-n-hexil)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-benzotriazole salt of general formula 2 is disclosed. 1-(N,N-dimethylaminomethyl)-benzotriazole is brought into reaction with equimolar amount of O-(2-ethyl-n-hexyl)-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: 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

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-(2-ethyl-n-hexil)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-benzotriazole salt of general formula 2 is disclosed. 1-(N,N-dimethylaminomethyl)-benzotriazole is brought into reaction with equimolar amount of O-(2-ethyl-n-hexyl)-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, in particular new lubricating oil additive.

SUBSTANCE: 1-(N,N-dimethylaminomethyl)-benzotriazole is brought into reaction with equimolar amount of O-(n-butyl)-O-(2-ethyl-n-hexyl)-dithiophosphoric acid at 80-100°C for 2-4 h. Yield of finished product is 92-100 %.

EFFECT: corrosion-resistant additive with antioxidative, high antiscoring properties, compatible with base oil.

1 cl, 1 ex, 2 tbl

FIELD: organic chemistry, in particular new lubricating oil additive.

SUBSTANCE: 1-(N,N-dimethylaminomethyl)-benzotriazole is brought into reaction with equimolar amount of O-(n-butyl)-O-(2-ethyl-n-hexyl)-dithiophosphoric acid at 80-100°C for 2-4 h. Yield of finished product is 92-100 %.

EFFECT: corrosion-resistant additive with antioxidative, high antiscoring properties, compatible with base oil.

1 cl, 1 ex, 2 tbl

FIELD: synthesis of lubricant oil additives.

SUBSTANCE: method for production of O-(2-ethyl-n-hexil)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-benzotriazole salt of general formula 2 is disclosed. 1-(N,N-dimethylaminomethyl)-benzotriazole is brought into reaction with equimolar amount of O-(2-ethyl-n-hexyl)-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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