SU679581A1 - Thioalkyl derivatives of 1,3,5-triazine as antiwear additives to lubricants - Google Patents

Thioalkyl derivatives of 1,3,5-triazine as antiwear additives to lubricants

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Publication number
SU679581A1
SU679581A1 SU762358260A SU2358260A SU679581A1 SU 679581 A1 SU679581 A1 SU 679581A1 SU 762358260 A SU762358260 A SU 762358260A SU 2358260 A SU2358260 A SU 2358260A SU 679581 A1 SU679581 A1 SU 679581A1
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SU
USSR - Soviet Union
Prior art keywords
triazine
lubricants
antiwear additives
thioalkyl derivatives
product
Prior art date
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SU762358260A
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Russian (ru)
Inventor
Татьяна Александровна Рогачевская
Татьяна Георгиевна Малышева
Александр Аркадьевич Гонор
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Предприятие П/Я А-7553
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Priority to SU762358260A priority Critical patent/SU679581A1/en
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Publication of SU679581A1 publication Critical patent/SU679581A1/en

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Description

К 29,1 г (0,1 М) тритиоцианурата кгши  в 60 мл водного спирта (1:1 no весу) при температуре добавл ют 76,4 г (0,3 М + 40% избытка) 1, 3, 3,3-тетрахлорпропа1 а. По окончании добавлени  температуру повышают до 90-95 С и выдерживают в течение 10 ч. В процессе синтеза каждые 45 ч провод т подщелачивание реакцион ной смеси 50%-ным водным раствором едкого кали (всего мл). По окончании реакции и охлаждении реакцион ной масйы отдел ют нижний тетрахлор пропановый слой и промывают его водой до отрицательной реакции на ионы хлора.Продукт высушивают безвод ным сульфатом натри  и фильтруют от осушител , избыток тетрахлорпропана отгон ют в вакууме (10 мм рт.ст.) в токе азота при температуре . Полученный сырой продукт очищают ме тодом колоночной хроматографии на с ликагеле. Дл  этого 10 г продукта загружали в колонну с силикагелем, смоченным гексаном; целевой пгюдукт элюируют смесью гексана с бензолом. После отгонки растворител  получают продукт в виде масл нистой светложелтой жидкости. Выход 63%; пй 1,5308 di 1,4246. 6,75; Найдено, %: S 15,6; N CI 52,0. N 6,80; Вычислено, %: S 15,6; CI 52,0. Молекул рный вес: найденный 613 ,0 вычисленный 613,5Пример 2. 2,4,6-трг -(Трихлорпентилтио )-1,3,5-триазин. К. 29,1 г (0,1 М) тиоцианурата ка ли  в 60 мл водного спирта (1:1 по весу) при температуре добавл ют 88,2 г тетрахлорпентана,(0,3 М + + 40% избытка). Далее процесс провод т аналогичн примеру 1 с тем отличием, что избыТаблица ток тетрахлорпентана отгон ют в виде азеотропа с этиленгликолем. Получают продукт в виде жидкости светложелтого цвета. Вьссод 58%; nZ 1,5730; 1,4228. Найдено, %; S 13,5; N 6,0; CI 45,9, Вычислено, %: S 13,7; N 6,02; CI 45,8, Молекул рный вес: найденный 696,7, вычисленный 697,5. Пример 3. 2,4,6-трг :-(Трихлорнонилтио )-1,3,5-триазин. К 29,1 г (0,1 л) тиоцианурата ка ЛИЯ в водно-спиртОвом растворе при температуре добавл ют 111,6 г тетрахлорнонана (0,3 М + 40% избытка ) . Услови  проведени  синтеза и первоначальной очистки аналогичны примеру 2. Отгонку непрореагировавшего тетрахлорнонана провод т в вакууме (5 мм рт.ст.) в токе азота при температуре 170°С в виде азеотропа с этиленгликолем . Очистку продукта провод т на колонне с силикагелем аналогично примеру 1. Целевой продукт представл ют собой в зкую жидкость. Выход 51%; п 1,6265; d 1,4203. Найдено, %: S 11,0; N 4,6; CI 37,0. Вычислено, %: S 11,6; N 4,8; CI 36,9. Молекул рный вес: найденный 865,0, вычисленный 865,5. Строение продуктов подтверждено данными ИК-спектроскопии. Пример 4. Соединени  примеров 1-3 испытывались в качестве противоизносных присадок к смазочному, маслу ДС-11. Дл  сравнени  приведены данные испытаний других присадок (табл. 1). Мол рна  концентраци  присадок 70 ммоль/л раствора.76.4 g (0.3 M + 40% excess) of 1, 3, 3.3 are added to 29.1 g (0.1 M) of kggsi tritiocyanurate in 60 ml of aqueous alcohol (1: 1 by weight). - tetrachloroprop 1 At the end of the addition, the temperature is raised to 90-95 ° C and maintained for 10 hours. During the synthesis process, the reaction mixture is alkalized every 45 hours with a 50% aqueous solution of potassium hydroxide (total ml). After the reaction is completed and the reaction mixture is cooled, the lower tetrachloror propane layer is separated and washed with water until the reaction with chlorine ions is negative. The product is dried with anhydrous sodium sulfate and filtered from the drying agent, the excess tetrachloropropane is distilled off in vacuum (10 mm Hg) in a stream of nitrogen at a temperature. The resulting crude product is purified by column chromatography on a gel medium. To this end, 10 g of the product was loaded into a column with silica gel wetted with hexane; target product was eluted with a mixture of hexane and benzene. After distilling off the solvent, the product is obtained in the form of an oily, light yellow liquid. Yield 63%; Py 1,5308 di 1,4246. 6.75; Found,%: S 15.6; N CI 52.0. N 6.80; Calculated,%: S 15.6; CI 52.0. Molecular weight: found 613, 0 calculated 613.5 Example 2 2,4,6-trg - (Trichloropentylthio) -1,3,5-triazine. K. 29.1 g (0.1 M) of thiocyanurate was added to 60 ml of aqueous alcohol (1: 1 by weight) at a temperature of 88.2 g of tetrachloropentane (0.3 M + + 40% excess). The process is then carried out as in Example 1 with the difference that excess Tetrachloropentane current is distilled off as an azeotrope with ethylene glycol. Get the product in the form of a light yellow liquid. Byss 58%; nZ 1.5730; 1.4228. Found,%; S 13.5; N 6.0; CI 45.9, Calculated,%: S 13.7; N 6.02; CI 45.8, Molecular weight: found 696.7, calculated 697.5. Example 3. 2,4,6-trg :-( Trichlorononylthio) -1,3,5-triazine. To a temperature of 29.1 g (0.1 l) of LIH thiocyanurate in a water-alcohol solution, 111.6 g of tetrachlorononan (0.3 M + 40% excess) are added at a temperature. The conditions for carrying out the synthesis and initial purification are similar to example 2. Distillation of unreacted tetrachlorononane is carried out in vacuum (5 mm Hg) in a stream of nitrogen at a temperature of 170 ° C as an azeotrope with ethylene glycol. Purification of the product was carried out on a column of silica gel as in Example 1. The target product was a viscous liquid. Yield 51%; p 1.6265; d 1.4203. Found,%: S 11.0; N 4,6; CI 37.0. Calculated,%: S 11.6; N 4.8; CI 36.9. Molecular weight: found 865.0, calculated 865.5. The structure of the products is confirmed by IR spectroscopy data. Example 4. The compounds of examples 1-3 were tested as antiwear additives for lubricating oil DS-11. For comparison, test data for other additives is given (Table 1). The molar concentration of the additives is 70 mmol / l solution.

Предлагаемое вещество по примеру 1 по приме| у 2 по примеру 3 Присадка по авт.ев. Присадка-по авт.св.The proposed substance of example 1 according to the example | at 2 according to example 3 Additive - on auth.

Известна  присадка ЛЗ-26Known additive LZ-26

101 99. 95101 99. 95

44,7 97 6844.7 97 68

Зависимость изменени  противоиэносных свойств образцов масла ДС-11 с присадкой по примеру 2 при конценПримечание , и прогрева кювет имеетThe dependence of the change in anti-enzymatic properties of the samples of DS-11 oil with an additive according to Example 2 at a concentration note and the heating of the cuvette has

Приведенные данные показывают, что вещества по изобретению обл 1дают значительной термостойкостью и высокой противоизноской эффективностью превосход щей противоизносную эффективность известных присадок.The data show that the substances according to the invention of region 1 exhibit significant heat resistance and high anti-wear efficacy superior to the anti-wear efficacy of known additives.

Claims (3)

1. Авторское свидетельство СССР1. USSR author's certificate 427045, кл. С 10 М 1/32, опубл. 427045, cl. C 10 M 1/32, publ. 1975. 351975. 35 2. Авторское свидетельство СССР2. USSR author's certificate 486037, кл. С 10 М 1/48, опубл. 486037, cl. With 10 M 1/48, publ. 1.976.1.976. 3. Авторское свидетельство СССР3. USSR author's certificate W 382630, кл. С 07 D 251/52, опубл. W 382630, class C 07 D 251/52, publ. 1973.1973.
SU762358260A 1976-05-10 1976-05-10 Thioalkyl derivatives of 1,3,5-triazine as antiwear additives to lubricants SU679581A1 (en)

Priority Applications (1)

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SU762358260A SU679581A1 (en) 1976-05-10 1976-05-10 Thioalkyl derivatives of 1,3,5-triazine as antiwear additives to lubricants

Applications Claiming Priority (1)

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SU762358260A SU679581A1 (en) 1976-05-10 1976-05-10 Thioalkyl derivatives of 1,3,5-triazine as antiwear additives to lubricants

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SU679581A1 true SU679581A1 (en) 1979-08-15

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