CN109942435B - Oxidation coupling high-temperature antioxidant solvent-free preparation method - Google Patents
Oxidation coupling high-temperature antioxidant solvent-free preparation method Download PDFInfo
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- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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Abstract
The invention provides an oxidation coupling high-temperature antioxidant solvent-free preparation method, which comprises the following specific preparation steps: adding N-phenyl-alpha-methylnaphthylamine or alkylated N-phenyl-alpha-methylnaphthylamine and alkylated diphenylamine compounds into a reaction vessel, wherein the molar ratio of the N-phenyl-alpha-methylnaphthylamine to the alkylated diphenylamine compounds is 1: 0.2 to 4.0; establishing vacuum, heating to 80-160 ℃ to melt the materials, and starting stirring; adding an oxidation coupling catalyst at the reaction temperature of 80-160 ℃, and reacting for 3-10 h; after the reaction is finished, slowly establishing vacuum till a 2mm HG column is removed, heating to 160-200 ℃, and removing the catalyst to obtain a tawny solid product. The preparation method adopts the direct melting reaction of the raw materials, the oxidation coupling catalyst plays double roles of reaction solvent and catalysis, no additional organic solvent is needed, the materials are uniformly mixed, the reaction condition is mild, and the reaction effect is good.
Description
Technical Field
The invention belongs to the technical field of organic high molecular compounds, and relates to a preparation method of an oxidation coupling high-temperature antioxidant.
Background
At present, amine antioxidants are the most used antioxidants in the field of lubricating oil, and the amine antioxidants are the broadest in application range, and mainly comprise p-phenylenediamine antioxidants, diphenylamine antioxidants, aniline antioxidants, naphthylamine antioxidants and the like. Except a few polymeric phenol antioxidants, the amine antioxidants have stronger stability in oil products and can be used at higher temperature, particularly the alkylated diphenylamine antioxidants can be suitable for mineral oil base oil, can be used as general internal combustion engine oil, and can also be used in lipid synthetic oil and can be used as aircraft engine lubricating oil. In recent years, with the increasingly deep research on the antioxidant mechanism of the oil products, various novel antioxidants are continuously developed, and the use efficiency of the oil products is greatly improved.
U.S. Pat. No.3573206 discloses a low cross-linking polymer of Diphenylamine (DPA) and N-phenyl α -methyl-naphthylamine (PNA) in low polymer yield and containing a large amount of unreacted DPA and PNA. Recently, some amine oligomer antioxidants reported at home and abroad have excellent high-temperature oxidation resistance, and are oxidation coupling products in the fields of aviation lubricating oil and high-temperature special industrial oil. For example, RHY533 developed by the research center for lubricating oil, Vanlube9317, R.T. Vanderbilt, USA, is an oxidative coupling product of the amine antioxidant, and the yield is low.
U.S. Pat. No.6204412 discloses a process for preparing an alkylated diphenylamine polymer comprising alkylating unsubstituted diphenylamine with a plurality of olefins to produce alkylated diphenylamine, and polymerizing the resulting alkylated diphenylamine with other aminic antioxidants to form an alkylated diphenylamine composition, wherein the oxidative coupling agent used is formamide peroxide.
U.S. patent No.2008045425 provides antioxidants for industrial, automotive and aviation lubricants and methods for making the same. Is formed by an alkylated diphenylamine and an alkylated naphthylamine under the action of a metal catalyst. The metal catalyst is a combination of a cation and an organic anion, such as acetylacetone metal. The reaction occurs in the presence of oxygen to form an antioxidant comprising oligomers of the alkylated diphenylamine and the alkylated naphthylamine, and the metal component of the catalyst.
Chinese patent cn.101348720a provides a compound amine antioxidant, which at least contains the following two substances: (1) alkylated diphenylamines; (2) alkylated N-phenyl-alpha-naphthylamines. The composite amine antioxidant is prepared by adding diisobutylene into a mixture of diphenylamine and N-phenyl-alpha-naphthylamine to carry out alkylation reaction in the presence of an acid catalyst. The amine antioxidant provided by the invention has good oil solubility and oxidation resistance, and can be widely applied to various lubricating oils. The antioxidant is prepared by the addition reaction of two amine compounds and olefin by using the same catalyst, the two amine compounds have different structures and different reaction temperatures with the olefin, and the product obtained by the reaction has more complex components and poor product stability.
Chinese patent CN.105733740A provides an amine oligomer antioxidant. The patent antioxidant is synthesized by using various oxidation coupling catalysts in an organic solvent through an alkylated diphenylamine compound and an N-phenyl-alpha-naphthylamine compound, the patent uses an organic and inorganic composite catalyst for reaction, the reaction effect is good, the reaction is mild, the product coupling degree is high, but the method uses a low-flash-point organic solvent, in order to avoid risks, the reaction temperature is low, the reaction time is long, meanwhile, the solvent needs to be distilled off in the post-treatment process, the catalyst used in the method is an organic and inorganic mixed catalyst, the catalyst is high in acidity and complex in components, a large amount of water is needed to remove the residual acid catalyst, and three wastes generated in the production process are more.
Disclosure of Invention
The technical problem is as follows: the invention aims to provide a more reasonable and efficient preparation method for preparing an amine oxidation coupling high-temperature antioxidant, which overcomes the defects of complex reaction conditions, long reaction time, low product yield, low polymerization degree, poor product stability, difficult post-treatment and the like in the prior art.
The technical scheme is as follows: in order to achieve the purpose, the invention provides the following technical scheme:
the invention relates to a solvent-free preparation method of an oxidation coupling high-temperature antioxidant, which comprises the following specific preparation steps:
1) adding N-phenyl-alpha-methylnaphthylamine or alkylated N-phenyl-alpha-methylnaphthylamine and alkylated diphenylamine compounds into a reaction vessel, wherein the molar ratio of the N-phenyl-alpha-methylnaphthylamine to the alkylated diphenylamine compounds is 1: 0.2 to 4.0;
2) establishing vacuum, heating to 80-160 ℃ to melt the materials, and starting stirring;
3) adding an oxidation coupling catalyst at the reaction temperature of 80-160 ℃, and reacting for 3-10 h;
4) after the reaction is finished, slowly establishing vacuum till a 2mm HG column is removed, heating to 160-200 ℃, and removing the catalyst to obtain a tawny solid product.
Preferably, the oxidative coupling catalyst is selected from the group consisting of dialkyl peroxides, peroxyesters, diacyl peroxides
One of them is less.
Preferably, the oxidative coupling catalyst is di-tert-butyl peroxide.
Preferably, the oxidation coupling catalyst used in the reaction process is one, and the oxidation coupling catalyst and alkyldiphenylamine are used
The molar ratio of the compounds is: 1: 0.2 to 1.
Preferably, the reaction vacuum degree is 200-300 mmHG column.
Preferably, the reaction temperature is 120-140 ℃.
Preferably, the temperature of the catalyst removal is 170-180 ℃.
Has the advantages that: compared with the prior art, the invention has the beneficial effects that:
1. the preparation method adopts the direct melting reaction of the raw materials, the oxidation coupling catalyst plays double roles of reaction solvent and catalysis, no additional organic solvent is needed, the materials are uniformly mixed, the reaction condition is mild, and the reaction effect is good.
2. The catalyst used in the method of the invention has single component, and the alcohol with single component is generated after the reaction consumption, and can be quickly separated from the reactant under negative pressure, and can be sold as a product. Compared with the organic-inorganic mixed catalyst in the prior art, the post-treatment of the product is simpler and has less three wastes.
3. The preparation method has the advantages of stable catalyst, higher reaction temperature and short reaction time, and can effectively improve the production efficiency.
Drawings
FIG. 1 shows a mass spectrum of example 2 of the present invention.
Detailed Description
The present invention will be further described with reference to the following examples.
The invention relates to an oxidation coupling high-temperature antioxidant solvent-free preparation method, which comprises the following preparation steps:
1) adding N-phenyl-alpha-methylnaphthylamine or alkylated N-phenyl-alpha-methylnaphthylamine and alkylated diphenylamine compounds into a reaction vessel, wherein the molar ratio of the N-phenyl-alpha-methylnaphthylamine to the alkylated diphenylamine compounds is 1: 0.2 to 4.0;
2) establishing vacuum, heating to 80-160 ℃ to melt the materials, and starting stirring;
3) adding an oxidation coupling catalyst at the reaction temperature of 80-160 ℃, and reacting for 3-10 h;
4) after the reaction is finished, slowly establishing vacuum till a 2mm HG column is removed, heating to 160-200 ℃, and removing the catalyst to obtain a tawny solid product.
Example 1
0.075mol and 16.425g of N-phenyl-alpha-methyl naphthylamine and 0.075mol and 29.475g of P and P diisooctyl diphenylamine are weighed into a 250ml four-neck flask, a thermometer, a condensation reflux pipe, a constant pressure titrator and a stirrer are respectively connected to four necks of the flask, a vacuum 300mmHG column is established, the reaction temperature is 80-100 ℃, 0.15mol and 36.3g of benzoyl peroxide are added, the reaction is refluxed for 10 hours, after the reaction is finished, the mixture is washed to be neutral by hot water, and the dark brown viscous liquid is obtained by reduced pressure distillation.
Example 2
0.075mol and 16.425g of N-phenyl-alpha-methyl naphthylamine and 0.075mol and 29.475g of P and P diisooctyl diphenylamine are weighed into a 250ml four-neck flask, a thermometer, a condensation reflux pipe, a constant pressure titrator and a stirrer are respectively connected to four necks of the flask, a vacuum 300mmHG column is established, the reaction temperature is 120-140 ℃, 0.15mol and 21.9g of di-tert-butyl peroxide are added, the reaction reflux is carried out for 3.5 hours, and after the reaction is finished, 20g of hot water is used for washing, and the pressure reduction distillation is carried out to obtain a yellow brown solid product.
Example 3
Weighing 0.05mol and 10.95g of N-phenyl-alpha-methylnaphthylamine and 0.1mol and 39.3g of P, P diisooctyldiphenylamine by using a 250ml four-neck flask, respectively connecting a thermometer, a condensation reflux pipe, a constant pressure titrator and a stirrer to the four necks of the flask, establishing a vacuum 300mmHG column, adding 0.2mol and 29.2g of di-tert-butyl peroxide at the reaction temperature of 120-140 ℃, refluxing for 4.5h, washing by using 30g of hot water after the reaction is finished, and distilling under reduced pressure to obtain a yellow brown solid product.
Example 4
Weighing 0.05mol of 10.95g of N-phenyl-alpha-methyl naphthylamine and 0.1mol of 39.3g of P, P diisooctyl diphenylamine by using a 250ml four-neck flask, respectively connecting a thermometer, a condensation reflux pipe, a constant pressure titrator and a stirrer to the four necks of the flask, establishing a vacuum 300mmHG column, adding 0.2mol of 48.4g of benzoyl peroxide at the reaction temperature of 80-100 ℃, carrying out reaction reflux for 9 hours, washing the mixture to be neutral by using hot water after the reaction is finished, and carrying out reduced pressure distillation to obtain dark brown viscous liquid.
Example 5
0.075mol and 16.425g of N-phenyl-alpha-methyl naphthylamine and 0.075mol and 29.475g of P and P diisooctyl diphenylamine are weighed into a 250ml four-neck flask, a thermometer, a condensation reflux pipe, a constant pressure titrator and a stirrer are respectively connected to four necks of the flask, a vacuum 200mm HG column is established, the reaction temperature is 100-120 ℃, 0.15mol and 19.8g of tert-butyl peroxyacetate are added, the reaction reflux is carried out for 6 hours, after the reaction is finished, the mixture is washed to be neutral by using hot water, and a yellow brown solid product is obtained by reduced pressure distillation.
Example 6
Weighing 0.05mol of N-phenyl-alpha-methyl naphthylamine and 10.95g of P, P diisooctyl diphenylamine in a 250ml four-neck flask, respectively connecting a thermometer, a condensation reflux pipe, a constant pressure titrator and a stirrer to the four necks of the flask, establishing a vacuum 200mm HG column, dropping 0.2mol of tert-butyl peroxyacetate and 26.4g of tert-butyl peroxyacetate at the reaction temperature of 100-120 ℃, carrying out reaction reflux for 6h, washing the reaction product to be neutral by using hot water after the reaction is finished, and carrying out reduced pressure distillation to obtain a yellow brown solid product.
Initial thermal decomposition temperature test
The products of examples 1-6 were analyzed using a DSC thermogravimetric analyzer to give the following initial thermal decomposition temperatures:
TABLE 1
According to the analysis results in table 1, the initial thermal decomposition temperature of the products of examples 1-6 is 20-50 ℃ higher than that of the alkyl diphenylamine, the N-phenyl-alpha-methyl naphthylamine and the alkylated N-phenyl-alpha-methyl naphthylamine, wherein the products of examples 2 and 5 have the best effect.
Oil viscosity and acid value testing
The products of the different examples, as well as the existing commercial products, were added to the base oil in the same mass fraction of 2%, and the hot-oxygen aging was carried out in an oven at an experimental temperature of 200 ℃, and the viscosity of the oil (kinematic viscosity at 100 ℃) and the acid value were measured as a function of time, with the results as shown in table 2 below:
TABLE 2
Note: the base oil is pentaerythritol ester
The results in table 1 show that the products of example 2 and example 5 synthesized in the present invention have excellent high temperature aging resistance in pentaerythritol ester base oil.
The product has higher oxidative coupling degree, higher thermal decomposition temperature and more stable product, and is suitable for various special high-temperature lubricating oil products. Compared with the prior art, the preparation method disclosed by the patent is simpler to clean, a large amount of organic solvent is not required to be added during cleaning, the reaction by-product is single and can be recovered, the reaction temperature is high, the reaction time is short, the catalyst does not contain inorganic acid, a large amount of water washing is not required for reaction intermediate liquid, the damage to equipment is small, and the three wastes are less.
The oxidation coupling high-temperature antioxidant prepared by the method is a polymer mixture of amine antioxidants, the product of the oxidation coupling high-temperature antioxidant is different from the oligomerization coupling AB in the prior art, more dimer is used, the reaction temperature in the steps of the method is high, the reaction degree is deep, and the product contains AmBnForm of a multimeric coupling body, and also the presence of Ax，ByFormal monomer coupling morphology. The oxidation coupling high-temperature antioxidant prepared by the method has more excellent result reflected on thermal stability, has higher thermal decomposition temperature, and is higher than the thermal decomposition temperature of the existing oligomerization coupling antioxidant by more than 10 ℃.
According to the method, an N-phenyl-alpha-naphthylamine compound (PNA) and an alkylated diphenylamine compound (ODPA) are used and coupled into an amine polymer under the action of an oxidation coupling catalyst, so that the polymer has few side reactions and high effective components, is suitable for various base oils, has excellent high-temperature oxidation resistance, and is particularly suitable for the field of aviation lubricating oil and high-temperature special industrial oil.
Claims (1)
1. An oxidation coupling high-temperature antioxidant solvent-free preparation method is characterized by comprising the following preparation steps:
0.075mol, 16.425g of N-phenyl-alpha-methyl naphthylamine and 0.075mol, 29.475g of P, P diisooctyl diphenylamine are weighed in a 250ml four-neck flask, and the four necks of the flask are respectively connected with a thermometer, a condensation reflux pipe, a constant pressure titrator and a stirrer;
establishing a vacuum 200mm HG column, adding 0.15mol of 19.8g of tert-butyl peroxyacetate at the reaction temperature of 100-120 ℃, and carrying out reaction reflux for 6 hours;
after the reaction is finished, washing the product to be neutral by using hot water, and distilling the product under reduced pressure to obtain a tan solid product.
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| CN201910291587.9A CN109942435B (en) | 2019-04-12 | 2019-04-12 | Oxidation coupling high-temperature antioxidant solvent-free preparation method |
| PCT/CN2019/084407 WO2020206754A1 (en) | 2019-04-12 | 2019-04-25 | Solvent-free preparation method for oxidative coupling high-temperature antioxidant |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
| CN105733740A (en) * | 2014-12-08 | 2016-07-06 | 中国石油天然气股份有限公司 | Amine oligomer anti-oxidant and preparation method thereof |
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- 2019-04-25 WO PCT/CN2019/084407 patent/WO2020206754A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
| CN105733740A (en) * | 2014-12-08 | 2016-07-06 | 中国石油天然气股份有限公司 | Amine oligomer anti-oxidant and preparation method thereof |
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Address after: 226600 No. 226, Nanhai Avenue (middle), Hai'an fine chemical park, Nantong City, Jiangsu Province Patentee after: Jiangsu Feiya Chemical Industry Group Co., Ltd Address before: 226600 No. 226, Nanhai Avenue (middle), Hai'an fine chemical park, Nantong City, Jiangsu Province Patentee before: Jiangsu Feiya Chemical Industry Co., Ltd |