SU1361142A1 - Bis(alkoxycarbonylmethyl)trithiocarbonates as extreme-pressure additives to lubricating oils - Google Patents

Abstract

The invention relates to substituted thiocarbonates, in particular bis- (iso-alkoxy- or butoxycarbonylmethyl) tritiocarbonate (TK), which, as extreme pressure additives, can be used in lubricating oils. The goal is to create more effective thiocarbonate additives. Synthesis of TC is carried out from sodium tritiocarbonate and monochloroacetic acid isopropyl or butyl ester at 50-55 ° C. Yield,%: batch, ° C at 0.3 mm Hg: for iso-C, H 72; 69; but for 70; 190-192. The tests of TCs show that they have a significantly better anti-seize effect compared to butyltriethyrylacetic acid butoxycarbonylmethyl ester butyltriethyrylacetic acid. 1 tab. «E CO and Mon.

Description

The invention relates to chemical compounds, more specifically to bis- (alkoxycarbonylmethyl) tritiocarbonates of the formula

ЯОССНпЗСЗСНСОСНОСОР}

Ii

o s o

where R - i - and ,, which can be used as extreme pressure additives for lubricating oils.

The purpose of the invention is to improve the countervailing properties of lubricating oils through the use of an additive belonging to tritiohydric acid derivatives and having a more effective action as compared to the most similar in structure and purpose of butyltrithiothiol acid with butoxycarbonylmethyl ester. Example 1 Bis- (Butoxy1: arbonylmethyl) tritiocarbonate.

To a solution of 46.2 g (0.3 mol) of sodium tritiocarbonate in 50 ml of dimethylformamide slowly fed 90.4 g (0.6 mol) of butyl ester monochlorine acetic acid and stirred at 50-60 C for 4 h. Mixture washed with water, distilled off the solvent, and 71 g (70% of theoretical) of bis- (butoxycarbonylmethyl) tritiocarbonate with the following characteristics was isolated by vacuum distillation with the following characteristics: b.p. 190-192 ° C / / 0.3 mm, 1.5405, 1.1654, MKONID 9L21,. 91.36,

Found,%: C 46.21; H 6.47; S 28.18;

 .

Calculated, X: C 46.13%; H 6.55; S 28.42.

Example 2. Bis- (Isopropyloxycarbonylmethyl) tritiocarbonate.

To a solution of 46.2 g (mol) of sodium tritiocarbonate in 50 ml of dimethylformamide slowly fed 82 g (0.6 mol) of isopropyl monochloroacetic acid ester and stirred at 50-55 ° C for 4 h. The mixture was washed with water, distilled 67 g (72% of the theoretical) of bis- (isopropyloxycarbonylmethyl) tritiocarbonate, which has the following characteristics: mp b.p. 168-169 ° C / 0.3 mm, 1.5456 1.2030, MKenaAA81.65, MR calc. 82.13.

Found,%: C 42.65; H 5.72; S 30.73.

 H Afl 4 Oe

Calculated,%: C 42.56; H 5.84; . S 30.98.

The described compounds are orange-colored liquids, well soluble in organic solvents benzene, hexane, ether, and also in mineral oils.

The structure of the compounds obtained is confirmed by the data of IR spectra. Thiocarbon fragment group

-S

 N

With S absorbs in the field.

1065-1058 cm A strong band with a frequency of 1736 cm characterizes the stretching vibrations of the carbonyl group. C-0 bond oscillations manifest -. Areas B 1165-1155 cm

,

The anti-seize efficiency of bis- (alkoxycarbonylmethyl) tritiocarbonates is established by testing them in a mixture with transmission oil TB-20. The test is carried out on an hour, four ball machine (CHP). Estimated indicators are: critical load of sticking of balls (P), load of welding of balls (R.) and index of teaser (And,).

The results of the comparative tests of 5% solutions of bis- (alkoxycarbonylmethyl) tritiocarbonates, taken from KI-LZ-23K, taken as the base of comparison and known additive of butoxycarbonylmethyl butt-trithioacetic acid ester are shown in the table.

From the test results, it follows that bis- (. Alkoxycarbonylmethyl) tritiocarbonates are significantly, TB-20 is superior in anti-seize properties, as well as the known additive L3-23k. At 5% concentration of bis- (isopropyloxycarbonyl) tritiocarbo-.

nat is 20 steps higher than additive L3-23k on the bully index, by 284H under the critical load of the jam and on by the load of welding.

Claims (1)

Invention Formula Bis- (Alkoxycarbonylmethyl) tritio-carbonates of the general formula: EtOCCHoSCSCHnCOR . II II 11 0 s 0 TB-20 (i-CjH OC) C S oil 0 TB-20 + (C CH2S) C S 0 TB-20 +  C C,  Ci S Additive L3-23k Editor H, Rogulich Compiled by T. Vlasov Tehred A. Kravchuk Proofreader M. Pjo Order 6195/28 Circulation 372 Subscription VNIIPU USSR State Committee for Inventions and Discoveries 113035, Moscow, Zh-35 ,. Raushska nab. D. 4/5 Production and Printing Enterprise, Uzhgorod, st. Project, 4 where R - iso-C H,, as extreme pressure additives to lubricating oils. ZG 79, 784 1558 1382 3900 70 1382 3900 69 1235 3479 59 1098 3479