CN1814717A - Extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative and preparing method - Google Patents

Extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative and preparing method Download PDF

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CN1814717A
CN1814717A CN 200610023444 CN200610023444A CN1814717A CN 1814717 A CN1814717 A CN 1814717A CN 200610023444 CN200610023444 CN 200610023444 CN 200610023444 A CN200610023444 A CN 200610023444A CN 1814717 A CN1814717 A CN 1814717A
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deravative
triazinyl
extreme pressure
containing hydroxyl
thiocarbamic acid
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CN100494329C (en
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李晶
曾祥琼
韩生
任天辉
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Shanghai Jiaotong University
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Abstract

This invention provides an EP anti-friction agent containing elkyl triazine flavianic acid ramification and its preparation method, which applies 2, 4, 6-3 mercapto-1, 3, 5-cyanuro and N, N-dialkyl flavianic epoxy alkyl ester as the raw material to get the anti-friction containing elkyl triazine flavianic acid ramification by replace reaction, which can be used as the additive of lubricant and increases the P<SUB>B</SUB> by 70%.

Description

Extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative and preparation method thereof
Technical field: the present invention relates to a kind of organic compound and preparation method thereof, waste threonine derivative of particularly a kind of hydroxyl triazine and preparation method thereof, it is used for lubricating oil as extreme-pressure anti-friction additive.
Background technology: the energy and environment are the two large problems that the whole world faces jointly.Along with environmental problem comes into one's own day by day, people more and more pay attention to the research and development of eco-friendly lubricating oil additive.Dialkyl dithiophosphate (ZDDP) has good anti-oxidant, anticorrosive and wear-resistant effect, but, ZDDP contains can cause galvanic corrosion and the zinc element of generation metal ash and the phosphoric that easily makes the poisoning of catalyst in the automobile exhaust gas processing apparatus, can bring the problem of aspects such as toxicity, water treatment, filtration obstruction and pollution.Existing studies show that, triazine derivative has demonstrated excellent performance as the ashless without phosphorus multifunctional additive for lubricating oil of environmental friendliness, and its initially synthetic parent cyanuric chloride is the competent basic Organic Chemicals in a kind of source.CN01139252.5 discloses a kind of dithioamino acid triazine derivative as lubricating oil additive, has good anti-extreme pressure energy, but does not relate to its abrasion resistance.CN03129696.3 and CN03129697.1 disclose a kind of single sulphur phosphorus triazine derivative and a kind of temephos pyrrolotriazine derivatives as extreme-pressure anti-friction additive, have good wear-resistant and anti-extreme pressure energy, but it still contain phosphoric.In order to adapt to environmental protection requirement, research and develop the focus that ashless without phosphorus multifunctional additive for lubricating oil has become current tribology research.
Summary of the invention: the object of the present invention is to provide the waste threonine derivative of a kind of ashless without phosphorus hydroxyl triazine, it has good wear-resistant and anti-extreme pressure energy as lubricating oil additive.
Another object of the present invention provides a kind of preparation method of above-mentioned extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative, and it is simple to have technology, reaction conditions gentleness, the cheap characteristics that are easy to get of the raw material of use.
The chemical structural formula of the waste threonine derivative extreme-pressure anti-friction additive of hydroxyl triazine of the present invention is as follows:
Or
R wherein 1, R 2Independently be selected from C respectively 1～C 20The straight or branched alkyl, or R 1R 2For-(CH 2) n-(n=3～8); R 3, R 4Independently be selected from hydrogen, C respectively 1～C 3The straight or branched alkyl.Wherein have 2,4,6-three (N, waste propylhomoserin (2 '-hydroxyl) propyl ester of N-diethyl alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (1 '-methylol) ethyl ester of N-diethyl alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (3 '-methyl-2 '-hydroxyl) the propyl ester alkylthio of N-diethyl)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (1 '-methylol-2 '-methyl) the ethyl ester alkylthio of N-diethyl)-1,3, the 5-s-triazine, 2,4,6-three (N, the waste propylhomoserin (1 ' of N-diethyl, 3 '-dimethyl-2 '-hydroxyl) propyl ester alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (2 '-(1 '-hydroxyl) ethyl) the ethyl ester alkylthio of N-diethyl)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (2 '-hydroxyl) propyl ester of N-di-n-butyl alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (1 '-methylol) ethyl ester of N-di-n-butyl alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (3 '-methyl-2 '-hydroxyl) the propyl ester alkylthio of N-di-n-butyl)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (1 '-methylol-2 '-methyl) the ethyl ester alkylthio of N-di-n-butyl)-1,3, the 5-s-triazine, 2,4,6-three (N, the waste propylhomoserin (1 ' of N-di-n-butyl, 3 '-dimethyl-2 '-hydroxyl) propyl ester alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (2 '-(1 '-hydroxyl) ethyl) the ethyl ester alkylthio of N-di-n-butyl)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (2 '-hydroxyl) propyl ester of N-diisooctyl alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (1 '-methylol) ethyl ester of N-diisooctyl alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (3 '-methyl-2 '-hydroxyl) the propyl ester alkylthio of N-diisooctyl)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (1 '-methylol-2 '-methyl) the ethyl ester alkylthio of N-diisooctyl)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (1 ', 3 '-dimethyl-2 '-hydroxyl) the propyl ester alkylthio of N-diisooctyl)-1,3, the 5-s-triazine, 2,4,6-three (N, waste propylhomoserin (2 '-(1 '-hydroxyl) ethyl) the ethyl ester alkylthio of N-diisooctyl)-1,3, the 5-s-triazine, 2,4,6-three (N, the waste propylhomoserin of N-two (dodecyl) (2 '-hydroxyl) propyl ester alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, the waste propylhomoserin of N-two (dodecyl) (1 '-methylol) ethyl ester alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, the waste propylhomoserin of N-two (dodecyl) (3 '-methyl-2 '-hydroxyl) propyl ester alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, the waste propylhomoserin of N-two (dodecyl) (1 '-methylol-2 '-methyl) ethyl ester alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, the waste propylhomoserin of N-two (dodecyl) (1 ', 3 '-dimethyl-2 '-hydroxyl) propyl ester alkylthio)-1,3, the 5-s-triazine, 2,4,6-three (N, the waste propylhomoserin of N-two (dodecyl) (2 '-(1 '-hydroxyl) ethyl) ethyl ester alkylthio)-1,3, the 5-s-triazine.
The preparation method of extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative is as follows:
With 1 mole 2,4,6-tri-thiol-1,3, the 5-s-triazine joins in 300～1600 milliliters the organic solvent, stir and slowly add 3 mol alkali and 2.7～3.3 moles of N down successively, the waste propylhomoserin epoxy alkyl of N-dialkyl group ester, ℃ following reaction is 0.5～12 hour in room temperature～150, is cooled to room temperature then, filter, the a small amount of organic solvent washing of filter residue, filtrate water are washed 3 times, use anhydrous magnesium sulfate drying again, filter, filtrate obtains extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative after steaming and removing organic solvent under normal pressure.
The N that the present invention uses, the chemical structural formula of the waste propylhomoserin epoxy alkyl of N-dialkyl group ester is as follows:
Figure A20061002344400061
R wherein 1, R 2Independently be selected from C respectively 1～C 20The straight or branched alkyl, or R 1R 2For-(CH 2) n-(n=3～8); R 3, R 4Independently be selected from hydrogen, C respectively 1～C 3The straight or branched alkyl.
The organic solvent that the present invention uses is acetone, benzene, toluene, chloroform, ethyl acetate, N, dinethylformamide, tetrahydrofuran (THF), dioxane, dimethyl sulfoxide (DMSO) or C 1-C 4Fatty Alcohol(C12-C14 and C12-C18).
The alkali that the present invention uses is triethylamine, pyridine, 2,4,6-collidine, N, accelerine, N, N-Diethyl Aniline, yellow soda ash, sodium bicarbonate, sodium hydroxide or potassium hydroxide.
The synthetic method of extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative of the present invention can be represented with following chemical equation:
Figure A20061002344400071
The waste threonine derivative extreme-pressure anti-friction additive of hydroxyl triazine of the present invention can use separately and add in the lubricating oil, can obtain the lubricating system of good wear-resistant and anti-extreme pressure energy, and it can improve P in mineral oil BValue about 70% reduces wear scar diameter 25%～40%, can improve P in rapeseed oil BValue about 20%; Also can with the compound use of other lubricating oil additive, can reach synergy synergy.
The addition of the waste threonine derivative extreme-pressure anti-friction additive of hydroxyl triazine of the present invention in lubricating oil is the 0.1wt%～15wt% of lubricating oil.
Description of drawings:
The infrared spectra spectrogram of Fig. 1: embodiment 1.
The thermogravimetric analysis figure (TGA) of Fig. 2: embodiment 1.
The infrared spectra spectrogram of Fig. 3: embodiment 2.
Embodiment: for a better understanding of the present invention, describe by the following examples.
Embodiment 1
With 2,4,6-tri-thiol-1,3,5-s-triazine 3.5g (about 0.02 mole) joins in the 100ml toluene, stirs slowly to add 2.4g (about 0.06 mole) sodium hydroxide and 15.7g (about 0.06 mole) N down successively the waste propylhomoserin epoxy of N-di-n-butyl propyl ester, 70 ℃ of following isothermal reactions 4 hours, cooling is filtered, and filter residue washs with small amount of toluene, filtrate washing 3 times (3 * 20ml), anhydrous magnesium sulfate drying filters, and filtrate obtains the light yellow thickness oily 2 of 17.2g after steaming and desolventizing under normal pressure, 4,6-three (N, waste propylhomoserin (2 '-hydroxyl) propyl ester of N-di-n-butyl alkylthio)-1,3,5-s-triazine and 2,4,6-three (N, waste propylhomoserin (1 '-methylol) ethyl ester of N-di-n-butyl alkylthio)-1,3, the 5-s-triazine.Fig. 1 is the Infrared spectroscopy of product, and analytical results is as follows: IR (cm -1): 3445.6 (O-H), 2957.7,2930.6,2871.7 (CH 2-,-CH 3), 1649.2,1465.5,1408.6 (triazine ring skeletons), 1252.7 (C-N), 1205.7,1125.0 (C=S).
Embodiment 2
With 2,4,6-tri-thiol-1,3,5-s-triazine 3.5g (about 0.02 mole) joins in the 100ml tetrahydrofuran (THF), stirs slowly to add 6.1g (about 0.06 mole) triethylamine and 22.4g (about 0.06 mole) N down successively the waste propylhomoserin epoxy of N-diisooctyl propyl ester, 70 ℃ of following isothermal reactions 4 hours, cooling is filtered, and filter residue washs with a small amount of tetrahydrofuran (THF), filtrate washing 3 times (3 * 20ml), anhydrous magnesium sulfate drying filters, and obtains the yellow thickness oily of 23.5g product 2 after filtrate is steamed under normal pressure and desolventized, 4,6-three (N, waste propylhomoserin (2 '-hydroxyl) propyl ester of N-diisooctyl alkylthio)-1,3,5-s-triazine and 2,4,6-three (N, waste propylhomoserin (1 '-methylol) ethyl ester of N-diisooctyl alkylthio)-1,3, the 5-s-triazine.Fig. 3 is the Infrared spectroscopy of product, and analytical results is as follows: IR (cm -1): 3421.0 (O-H), 2958.6,2930.6,2872.4 (CH 2-,-CH 3), 1651.2,1462.8,1410.0 (triazine ring skeletons), 1261.0 (C-N), 1193.7,1117.4 (C=S).
Embodiment 3
Present embodiment is the ultimate analysis of sample.Table 1 has been listed the results of elemental analyses of embodiment 1～2, results of elemental analyses as can be known from table 1, the measured value of the C of all target compounds, H, N, S element and the theoretical value of calculating by molecular formula meet the requirement of lubricating oil additive basically, and absolute error is in allowed band.Can determine that the gained compound is a target compound.
Table 1 results of elemental analyses
Embodiment 1 2
Element C H N S C H N S
Theoretical value (%) 48.71 7.55 8.74 30.01 58.29 9.32 6.47 22.23
Measured value (%) 49.27 7.75 8.39 29.38 58.50 9.79 9.51 21.62
Absolute error (%) 0.56 0.20 0.35 0.63 0.21 0.47 0.27 0.61
Embodiment 4
Present embodiment is extreme pressure and antiwear behavior test and the heat stability testing to sample
According to the GB3142-82 standard, be added on last non seizure load (P in commercially available refining rapeseed oil (RSO) and the hydrogenation mineral oil (5CST) to base oil with by the waste threonine derivative of the hydroxyl triazine of example 1,2 preparation BValue) carried out measuring (addition is 1.0wt%).The four-ball tester that experiment is used is the EP lubricant tester of English home-made Seta-Shell type, and used steel ball is a secondary GCr15 standard steel ball (AISI-52100), and its diameter is 12.7mm, and hardness is 59～61HRC.At room temperature carry out, rotating speed is 1450rpm.The results are shown in table 2.
Last non seizure load (the P of table 2 base oil and various additives BValue)
Additive Concentration (wt%) P BValue (N) Additive Concentration (wt%) P BValue (N)
RSO 100 686 5CST 100 510
Embodiment 1 1.0 804 Embodiment 2 1.0 882
Embodiment 2 1.0 862
The result shows that such hydroxyl pyrrolotriazine derivatives adds to and has certain extreme pressure property in the lubricating oil.
With the vertical omnipotent friction wear testing machine of MMW-1 that trier factory in Jinan produces the waste threonine derivative of hydroxyl triazine of commodity ZDDP and embodiment 1,2 preparations has been measured the 392N load down, experimental period is 30 minutes, additive level is 5.0wt%, and rotating speed is the wear scar diameter (WSD) of 1450rpm.Used steel ball is a secondary GCr15 standard steel ball (AISI-52100), and its diameter is 12.7mm, and hardness is 59～61HRC; Testing used base oil is hydrogenation mineral oil (5CST).Experiment is at room temperature carried out.The results are shown in table 3.
Table 3 four ball commentary valency results (wear scar diameter, WSD)
Additive Concentration (%) Wear scar diameter (mm)
Base oil 100 0.684
ZDDP 5.0 0.406
Embodiment 1 5.0 0.513
Embodiment 2 5.0 0.416
The result shows that the synthetic compound can effectively reduce the WSD value among the embodiment, and effect is near ZDDP.
Fig. 2 represents the thermogravimetric analysis figure (TGA) of the waste threonine derivative extreme-pressure anti-friction additive of hydroxyl triazine among the embodiment 1, and as can be seen from the figure decomposition temperature has higher thermostability more than 270 ℃, is suitable as lubricating oil additive.

Claims (6)

1, a kind of extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative is characterized in that its chemical structural formula is as follows:
Figure A2006100234440002C2
Or
R wherein 1, R 2Independently be selected from C respectively 1～C 20The straight or branched alkyl, or R 1R 2For-(CH 2) n-(n=3～8); R 3, R 4Independently be selected from hydrogen, C respectively 1～C 3The straight or branched alkyl.
2, extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative as claimed in claim 1, it is characterized in that as lubricated oil additives use separately or and the compound use of other lubricating oil additive, its addition is the 0.1wt%～15wt% of lubricating oil.
3, a kind of preparation method of extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative according to claim 1 is characterized in that its preparation method is as follows:
With 1 mole 2,4,6-tri-thiol-1,3, the 5-s-triazine joins in 300～1600 milliliters the organic solvent, stir and slowly add 3 mol alkali and 2.7～3.3 moles of N down successively, the waste propylhomoserin epoxy alkyl of N-dialkyl group ester, ℃ following reaction is 0.5～12 hour in room temperature～150, is cooled to room temperature then, filter, the a small amount of organic solvent washing of filter residue, filtrate water are washed 3 times, use anhydrous magnesium sulfate drying again, filter, filtrate obtains extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative after steaming and removing organic solvent under normal pressure.
4, the preparation method of extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative according to claim 3 is characterized in that N, and the chemical structural formula of the waste propylhomoserin epoxy alkyl of N-dialkyl group ester is as follows:
Figure A2006100234440003C1
R wherein 1, R 2Independently be selected from C respectively 1～C 20The straight or branched alkyl, or R 1R 2For-(CH 2) n-(n=3～8); R 3, R 4Independently be selected from hydrogen, C respectively 1～C 3The straight or branched alkyl.
6, the preparation method of extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative according to claim 3, it is characterized in that organic solvent is acetone, benzene, toluene, chloroform, ethyl acetate, N, dinethylformamide, tetrahydrofuran (THF), dioxane, dimethyl sulfoxide (DMSO) or C 1-C 4Fatty Alcohol(C12-C14 and C12-C18).
7, the preparation method of extreme pressure wear-resistant containing hydroxyl-triazinyl-thiocarbamic acid deravative according to claim 3, it is characterized in that alkali is triethylamine, pyridine, 2,4,6-collidine, N, accelerine, N, N-Diethyl Aniline, yellow soda ash, sodium bicarbonate, sodium hydroxide or potassium hydroxide.
CNB2006100234442A 2006-01-19 2006-01-19 Extreme pressure wear-resistant agent containing hydroxyl-triazinyl-thiocarbamic acid deravative and preparing method Expired - Fee Related CN100494329C (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111303061A (en) * 2020-04-08 2020-06-19 玛可索(苏州)石化有限公司 Arylamine compound and preparation method and application thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111303061A (en) * 2020-04-08 2020-06-19 玛可索(苏州)石化有限公司 Arylamine compound and preparation method and application thereof
CN111303061B (en) * 2020-04-08 2021-05-11 玛可索(苏州)石化有限公司 Arylamine compound and preparation method and application thereof

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