CN111205207A - Antioxidant and application - Google Patents
Antioxidant and application Download PDFInfo
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- CN111205207A CN111205207A CN202010185407.1A CN202010185407A CN111205207A CN 111205207 A CN111205207 A CN 111205207A CN 202010185407 A CN202010185407 A CN 202010185407A CN 111205207 A CN111205207 A CN 111205207A
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- lubricating oil
- tert
- butyl
- hydroxyphenyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/02—Preparation of carboxylic acid esters by interreacting ester groups, i.e. transesterification
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
- C10M135/30—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/048—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution, non-macromolecular and macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Abstract
The invention relates to an antioxidant and application thereof, in particular to an antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ] and application thereof in lubricating oil, aiming at solving the technical problems of inhibiting and delaying the oxidation and deterioration of the lubricating oil and prolonging the service time of the lubricating oil, the invention provides an antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ] "which has good oxidation resistance and thermal stability, low toxicity and good compatibility, can effectively control the increase of the viscosity and acid value of the lubricating oil and reduce the occurrence of high-temperature deposits.
Description
Technical Field
The invention relates to an antioxidant and application thereof, in particular to an antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ] and application thereof in lubricating oil.
Background
The lubricating oil consists of 80-90% of base oil, the base oil is mainly hydrocarbon compound formed by hydrocarbon, the hydrocarbon compound exposed to oxygen and heated condition is easy to oxidize and deteriorate, and metal parts, such as copper and iron, contacting with the using part of the lubricating oil are also catalysts for promoting oxidation, so the oxidative deterioration of the lubricating oil inevitably arouses attention of people.
In order to inhibit and delay the oxidation and deterioration of the lubricating oil and prolong the service life of the lubricating oil, the addition of the antioxidant is the most effective method, the antioxidant can inhibit the oxidation of the lubricating oil and reduce the increase of the acid value and viscosity of the lubricating oil, and the most used antioxidants in the market at present mainly comprise phenols and arylamines.
In the process of implementing the embodiment of the invention, the inventor finds that at least the following defects exist in the background art;
in recent years, due to the influence of environmental protection pressure, emission regulations, fuel economy and resource exhaustion, lubricating oil is required to have better oxidation resistance and thermal stability so as to meet the rigorous requirements of engines and industrial applications, and the existing antioxidant is not enough to meet the requirements of the current society on the lubricating oil.
Disclosure of Invention
The invention aims to provide an antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ], which has good oxidation resistance and thermal stability, low toxicity and good compatibility, can effectively control the increase of the viscosity and acid value of lubricating oil, and reduces the occurrence of high-temperature sediments.
In order to achieve the above object, the technical scheme of the present invention is to provide an antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ], which has a chemical structure:
a lubricating oil functional package comprising from about 1% to about 75% of 2, 2-thiobis [ pentaerythritol 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] and at least one other lubricating oil additive.
Further wherein the at least one other lubricating oil additive is selected from the group consisting of detergents, dispersants, antioxidants, extreme pressure agents, friction modifiers, anti-foam agents, anti-corrosion agents, pour point depressants.
A lubricating oil composition comprising at least one oil of lubricating viscosity and an antioxidant which is 2, 2-thiobis [ pentaerythritol 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ].
Further, the proportion of the 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ] in the total lubricating oil composition is 0.1% -1%.
Further, the lubricating oil composition further comprises at least one lubricating oil additive.
Preferably, the proportion of the 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ] in the total lubricating oil composition is 0.2% to 0.5%.
Further, the lubricating oil composition is characterized by comprising the following components:
67.9% -78.3% of GTL base oil;
10% -15% of synthesized diester base oil;
3% -8% of a tackifier;
7.4% -9.6% of lubricating oil functional complexing agent;
the lubricating oil functional complexing agent is formed by compounding various additives according to requirements.
0.2-0.5% of 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ].
The functional compound agent for the lubricating oil has the advantages of high lubricating performance,
preferably, the components of the lubricating oil composition are as follows:
67.9% -78.3% of GTL base oil;
10% -15% of synthesized diester base oil;
3% -8% of a tackifier;
0.1% -0.2% of polymethacrylate pour point depressant;
7.3% -9.4% of lubricating oil functional complexing agent;
0.2-0.5% of 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ].
Preferably, the tackifier used in the lubricating oil composition is a hydrogenated styrene isoprene type tackifier, and the hydrogenated styrene isoprene type tackifier is prepared by decocting three types of base oil with 10.5% of dry glue.
Preferably, the GTL base oil used in the present invention is a shell GTL base oil.
Preferably, the GTL base oil used in the present invention is shell GTL420 and shell GTL 430.
The preparation method of the 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid pentaerythritol ester comprises the following steps:
weighing a certain amount of pentaerythritol powder, dissolving the pentaerythritol powder into an N, N-dimethyl amide solution, slowly dripping the pentaerythritol powder into a certain amount of 3, 5-methyl ester under the protection of nitrogen, heating to 155-165 ℃, reacting for 4-6 hours, using sodium methoxide as a catalyst, wherein the molar ratio of the 3, 5-methyl ester to the pentaerythritol is 4: 4-4: 4.6, carrying out an ester exchange reaction, recrystallizing with methanol after the experiment is finished, and drying to obtain white to yellowish powder of 3- (3, 5-di-tert-3-butyl-4-hydroxyphenyl) pentaerythritol propionate.
The preparation method of the 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ]:
adding a certain amount of thiophenyl ethanol and 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate into a reaction container, wherein the molar ratio of the thiophenyl ethanol to the 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate is 2: 1-3: 1, adding 0.5-0.8% of hydrogen oxidation catalyst, starting stirring and heating, starting a vacuum system to ensure that the reaction pressure is 0.08-0.2 MP a, controlling the reaction temperature at 140-160 ℃, and reacting for 4-8 h. And after the reaction is finished, cooling to 50 ℃, removing the catalyst through vacuum filtration, and then distilling the filtrate under reduced pressure at the temperature of 150-180 ℃ under the condition of 0.06-0.10 MP a to remove unreacted raw materials to obtain a brownish red transparent thick liquid product, namely antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ].
The reaction equation is as follows:
compared with the prior art, the invention has the following beneficial effects:
1. the invention synthesizes an antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ], which is a phenolic ester compound. The phenolic ester functional group has good oxidation resistance;
2. the antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ] synthesized by the invention has good thermal stability, low toxicity and good compatibility;
3. the antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ] synthesized by the invention contains sulfur elements, has good corrosion resistance and can effectively inhibit the increase of acid value;
4. the antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ] engine lubricating oil has an oil change period of over 1.5-2.0 kilometers, which is longer than that of the engine lubricating oil of international brands in the market.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
Synthesis of 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid pentaerythritol ester: weighing 0.1 mol of pentaerythritol powder, dissolving the pentaerythritol powder in 100 g N, N-dimethyl amide solution, slowly dripping the solution into 0.105 mol of 3, 5-methyl ester under the protection of nitrogen, heating the solution to 160 ℃, reacting for 5 hours, carrying out transesterification reaction by using 0.5 g of sodium methoxide as a catalyst, recrystallizing the product by using methanol after the experiment is finished, and drying the product to obtain white powder of 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate. The reaction equation is as follows:
synthesis of 2, 2-thiobis [ pentaerythritol 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ]:
2 mol of thiophenylethanol and 1 mol of pentaerythritol 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate are added into a 500 mL three-neck reaction flask, 0.6% of hydrogen oxidation catalyst is added, stirring and heating are started, a vacuum system is started, the reaction pressure is ensured to be 0.12 MP a, the reaction temperature is controlled at 155 ℃, and the reaction time is 6 hours. After the reaction is finished, the temperature is reduced to 50 ℃, the catalyst is removed by vacuum filtration, and then the filtrate is subjected to vacuum distillation at the temperature of 160 ℃ under the condition of 0.08 MP a to remove the unreacted raw materials, so as to obtain a brownish red transparent thick liquid product, namely antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ]. The reaction equation is as follows:
comparison of antioxidant Properties of 2, 2-Thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) Pentaerythrityl propionate ] antioxidant and 2, 6-di-tert-butyl-p-cresol T501
The experimental method comprises the following steps: ASTM D2272 rotating oxygen bomb method
The experimental principle is as follows: the oil sample, distilled water and copper wire coil were placed together in a glass container with a lid and then placed in an oxygen bomb capable of measuring pressure. The bomb was charged with oxygen at 620kpa at room temperature and placed in a 150 ℃ oil bath. As the oil was oxidized, oxygen was consumed from the bomb, and when the specified pressure drop of 175kpa was reached, the experiment was stopped, the time spent was called the oxidation induction period. The longer the oxidation induction period, the better the antioxidant properties of the oil.
The addition amount of antioxidant is 0.8% (weight ratio)
The results of the experiment are shown in table 1 below:
the experimental results show that the antioxidant performance of the antioxidant in the first-class, second-class and third-class base oils is far better than that of a commercial product T501.
Evaluation of high-temperature Oxidation resistance of antioxidant of the present invention
The antioxidant properties of the antioxidants were evaluated using the U.S. Federal test method FTM 5308.7. The base oil was pentaerythritol tetranonyl ester, with 2% tricresyl phosphate (antiwear agent) and 0.05% benzotriazole (corrosion inhibitor) added. The antioxidant 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ] was added in an amount calculated on the active ingredient thereof for comparison. In the actual product, they all have 50% of active ingredient (dissolved in the base solvent). The results of the oxidation experiments are shown in tables 2 and 3 below.
As can be seen from tables 2 and 3, the antioxidant 2, 2-thiobis [ pentaerythritol 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] of the present invention is an excellent antioxidant and can control the increase in viscosity and the increase in acid value of oils well.
An engine oil incorporating the antioxidant 2, 2-thiobis [ pentaerythritol 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] as shown in Table 4 below:
the results of four formulation schemes in the ASTM D7097B high temperature deposit test (oil sludge control capability) are shown in table 5 below:
as can be seen from the experimental results in Table 5, the high temperature deposits in the engine lubricating oil scheme with the antioxidant of the present invention are significantly less than those in the engine lubricating oil scheme without the antioxidant of the present invention, indicating that the antioxidant 2, 2-thiobis [ pentaerythritol 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] of the present invention has an excellent ability to control high temperature deposits.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
Claims (10)
1. A novel antioxidant, wherein the antioxidant is 2, 2-thiobis [ pentaerythritol 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], having the formula:
2. a lubricating oil composition comprising at least one oil of lubricating viscosity and the antioxidant pentaerythritol 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] of claim 1.
3. The lubricating oil composition of claim 2, wherein the proportion of 2, 2-thiobis [ pentaerythritol 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] in the total lubricating oil composition is 0.1% to 1%.
4. The lubricating oil composition of claim 3, wherein the proportion of 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] in the total lubricating oil composition is 0.2% to 0.5%.
5. Lubricating oil composition according to any of claims 2-4, characterized in that the lubricating oil composition further comprises at least one lubricating oil additive.
6. The lubricating oil composition of claim 5, wherein the components of the lubricating oil composition are as follows:
67.9% -78.3% of GTL base oil;
10% -15% of synthesized diester base oil;
3% -8% of a tackifier;
7.4% -9.6% of lubricating oil functional complexing agent;
0.2-0.5% of 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ].
7. The lubricating oil composition of claim 5, wherein the components of the lubricating oil composition are as follows:
67.9% -78.3% of GTL base oil;
10% -15% of synthesized diester base oil;
3% -8% of a tackifier;
0.1% -0.2% of polymethacrylate pour point depressant;
7.3% -9.4% of lubricating oil functional complexing agent;
0.2-0.5% of 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) pentaerythritol propionate ].
8. The lubricating oil composition according to claim 6 or 7, wherein the tackifier used in the lubricating oil composition is a hydrogenated styrene isoprene type tackifier, and the hydrogenated styrene isoprene type tackifier is prepared by decocting three types of base oil with 10.5% of dry glue.
9. A lubricating oil functional package comprising from about 1% to about 75% of the pentaerythrityl 2, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] of claim 1 and at least one other lubricating oil additive.
10. The functional complex of lubricating oil of claim 9, wherein the at least one other lubricating oil additive is selected from the group consisting of detergents, dispersants, antioxidants, extreme pressure agents, friction modifiers, anti-foam agents, anti-corrosion agents, pour point depressants.
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| CN202010185407.1A CN111205207A (en) | 2020-03-17 | 2020-03-17 | Antioxidant and application |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6291703B1 (en) * | 1998-02-09 | 2001-09-18 | Ciba Specialty Chemicals Corporation | Preparation of substituted hydroxyhydrocinnamate esters by continuous transesterification using reactive distillation |
| WO2004033699A1 (en) * | 2002-10-10 | 2004-04-22 | Ciba Specialty Chemicals Holding Inc. | Process for the preparation of phenolic carboxylic acid derivatives by enzymatic catalysis |
| CN103319387A (en) * | 2013-06-19 | 2013-09-25 | 常州大学 | Preparation method of thiophenol compound antioxidant product |
-
2020
- 2020-03-17 CN CN202010185407.1A patent/CN111205207A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6291703B1 (en) * | 1998-02-09 | 2001-09-18 | Ciba Specialty Chemicals Corporation | Preparation of substituted hydroxyhydrocinnamate esters by continuous transesterification using reactive distillation |
| WO2004033699A1 (en) * | 2002-10-10 | 2004-04-22 | Ciba Specialty Chemicals Holding Inc. | Process for the preparation of phenolic carboxylic acid derivatives by enzymatic catalysis |
| CN103319387A (en) * | 2013-06-19 | 2013-09-25 | 常州大学 | Preparation method of thiophenol compound antioxidant product |
Non-Patent Citations (2)
| Title |
|---|
| STEPHEN D. PASTOR 等: "S-(HYDROXYMETHYL) 4-HYDROXYPHENYL SULFIDES:SYNTHESIS AND SELECTED CHEMISTRY OF SOME STABLE HEMIMERCAPTALS", 《PHOSPHOROUS AND SULFUR AND THE RELATED ELEMENTS》 * |
| 李维义 等: "季戊四醇酯抗氧剂的合成进展", 《合成材料老化与应用》 * |
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Application publication date: 20200529 |