SU1146303A1 - S-zinnamylisopropylxanthate as antiseize additive to lubricating oils - Google Patents

Abstract

S-Cinnamyl isopropyl xanthate of the formula sn snsng8sosnns S snz as an anti-seize lubricant additive.

Description

four

Od CO i The invention relates to a new production of xantoUenic acids, namely, to S-cinnamyl isopropylxane togenate of the formula -CH-CHCH2 COCHH3; I-CH 3 O as an anti-seize lubricant additive. Known propyl ester of n-buti xanthogenic acid of the formula CjHYSCOCi Hg $ used as an additive to lubricating oils. (jj. One of the about 3 adducts with howl of this compound is not high enough. The aim of the invention is to improve the anti-seizure properties in a series of xanthoric acid derivatives. The goal is achieved by offering S-cinnamyl isopropyl xanthate of formula (D) Qualification of lubricant oil extreme anti-seize agent. This compound is obtained by reacting cinnamyl chloride (chloromethylated styrene) with potassium propyl xanthogenate at 60 ° C. The reaction is carried out in the presence of a polar solvent for 5 hours. The target product is 90%. The structure of the obtained Compound is confirmed by the data of elemental analysis, IMP- and G-spectroscopy. Example: To a mixture of 35 g, (0.2 mol) of isopropyl xanthate, 30.5 g are gradually added to 50 ml of isopropyl alcohol (0.2 m Zinnam Lchloride and stirred at 60 ° C for 5 h. The mixture is washed with water, filtered and subjected to vacuum distillation. Obtain 45.4 g (90 substances, So kip. 120 - 125 ° C / /0.4 mm Hg, p 1.6070, df 1.1232. Found %: C 61.94, H 6.26, S 24.8 C HteOSg Calculated: C 61.88, H 6.33, S 25.4 S-Cinnamyl isopropyl xanthate is a light yellow liquid 3 chorodio soluble in organic solvents. In the IR spectra of compound (D), there is an intense absorption band in the 1640 cm region, corresponding to the double bond, an intense absorption band with a frequency of 1610 cm, related to the aromatic ring, and intense absorption bands in the 1225, 1080 and 1050 cm region, corresponding to P-0-CS group, weak band at 590 cm, characterizing CS bond. In the IR spectra of both the initial cinnamyl chloride and the S-cinnamyl isopropyl xanthate derived from it, an absorption band is observed in the 690 cm region, which characterizes the monosubstituted aromatic ring. IM spectra are recorded on a Varian YES-60 instrument with an operating frequency of 60 MHz and an internal standard of tetramethylsilane, the solvent CCt. S ppm: 1.4 6 H, (CH.), 3.8 (2H, -CH, -), 5.55 1H, -CH (CH,) J, 6.95 (5H, CgH5) 5.5-6.5 (2H,). The effectiveness of S-cinnamyl pro-. plexanthogenate is established by testing it in vaseline oil and TB-20 transmission oil. In tab. 1 shows the test results of a yazelin oil (MBM) with 3% S-oxidized isopropyl xanthate. Tests in vaseline oil and in TB-20 oil are also carried out in comparison with propyl ester of N -butylxanthic acid on a four-ball friction machine on UIX-15 balls with a diameter of 12.7 mm at a sliding speed of 1400 rpm. Estimated indicators are critical load of sticking of balls (Pj.-, H), welding load (, H) and generalized wear rate (SPI). The results of comparative tests are given in table. 2. From the data obtained it can be seen that the proposed 3-tin isopropylxane togenate of the formula (D) as in macro vaseline oil (kinematic viscosity Q 16 cSt) ,. and in the high-vis transmission oil TB-20 foo cSt) with respect to the scoring properties, it significantly exceeds the propyl ester of H-bu ilxanthoic acid.

Table 1

Copper corrosion on ASTM D-130, points 120 ° С, 3 h

1А ° С, 3h

Corrosi Art. 10 (protective properties) according to GOST 9.054-75,

MVM + 3% S-cinnamyl isopropyl xanthate

MVM + 3% propi

ester H-butylxanthic acid

4c

3 in 1 in

3 in

table 2

63

2820

52

2510

Naimva ova ee

TB-20 oil

TV-20 + 5% S-cinnamyl isopropyl xanthate

TB-20 - "5% propyl ether, H-butylxanthogenic acid,

Continuation of table 2

Tests on the state of emergency

34

1590

72

3980

59

2820