CN109942435A - A kind of oxidation coupling high-temperature antioxidant non-solvent preparation - Google Patents
A kind of oxidation coupling high-temperature antioxidant non-solvent preparation Download PDFInfo
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- CN109942435A CN109942435A CN201910291587.9A CN201910291587A CN109942435A CN 109942435 A CN109942435 A CN 109942435A CN 201910291587 A CN201910291587 A CN 201910291587A CN 109942435 A CN109942435 A CN 109942435A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—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
- 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
- C07C211/55—Diphenylamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
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- 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
- 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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- Oil, Petroleum & Natural Gas (AREA)
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- Medicinal Chemistry (AREA)
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- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of oxidation coupling high-temperature antioxidant non-solvent preparations, specific preparation process is as follows: N- phenyl-Alpha-Methyl naphthylamines or alkylation N- phenyl-Alpha-Methyl naphthylamines and alkylated diphenylamine class compound being added in the reaction vessel, molar ratio is 1:0.2~4.0;Vacuum is established, 80~160 DEG C of thawing materials are warming up to, opens stirring;Oxidation coupling catalyst is added at 80~160 DEG C in reaction temperature, reacts 3~10h;After reaction, it slowly establishes vacuum to 2mmHG column to go, is warming up to 160~200 DEG C, Removal of catalyst obtains Tan solid product.Preparation method of the present invention uses the direct frit reaction of raw material, and oxidation coupling catalyst itself plays a dual role of reaction dissolvent and catalysis, and without additional addition organic solvent, material is uniformly mixed, and reaction condition is mild, and reaction effect is good.
Description
Technical field
The invention belongs to organic high molecular compound technical fields, are related to a kind of preparation side of oxidation coupling high-temperature antioxidant
Method.
Background technique
Amine antioxidants are that lubricating oil field uses earliest, the most wide kind antioxidant of use scope, wherein mainly at present
There are p-phenylenediamine kind antioxidant, diphenylamine antioxidant, aniline kind antioxidant, naphthylamines kind antioxidant etc..Except a small number of polymerism phenol
Kind antioxidant, amine antioxidants stronger stability in oil product, can use at a higher temperature, especially be alkylated two
Aniline kind antioxidant can be suitably used in mineral oil base oil, as general purpose engine oil, while can be used for lipid synthetic oil
In, as aviation engine lubricating oil.In recent years, all kinds of novel as people are increasingly deep to oil product antioxidation mechanism research
Antioxidant is increasingly developed, the significant increase service efficiency of oil product.
United States Patent (USP) U.S.pat.No.3573206 discloses a kind of diphenylamines (DPA) and N- phenyl Alpha-Methyl naphthylamines
(PNA) the low cross-polymerization body that polymerization is formed contains a large amount of unreacted DPA and PNA wherein polymeric yield is lower.Most
The some amine oligomer antioxidants closely reported both at home and abroad have splendid pyro-oxidation resistance, are used for aeroengine oil, high temperature
Special industrial is exactly this kind of oxidation coupling product with oily field.Such as the exploitation of China Petroleum Lanzhou lubricating oil research center
The Vanlube9317 of RHY533, the production of R.T.Vanderbilt company, the U.S. are this amine antioxidants oxidation coupling products,
Yield is lower.
United States Patent (USP) U.S.pat.No.6204412 discloses a kind of method for preparing alkylated diphenylamine polymer, the party
Method includes unsubstituted diphenylamines and a variety of olefin alkylation reactions, and the alkylated diphenylamine of generation and other amine antioxidants are poly-
Close, formed alkylated diphenylamine composition, used in oxidation coupling agent be peroxidating formamide.
United States Patent (USP) U.S.pat.No.2008045425 provides the antioxygen for industry, motor vehicle and aeroengine oil
Agent and preparation method thereof.It is formed under the action of metallic catalyst with a kind of alkylated diphenylamine and alkylation naphthylamines.The gold
Metal catalyst is the combination of cation and organic anion, such as cetylacetone metallic.The reaction occurs in the presence of oxygen, thus
Form the anti-of the metal component of the oligomer comprising the alkylated diphenylamine and the alkylation naphthylamines and the catalyst
Oxidant.
Chinese patent CN.101348720A provides a kind of composite amine antioxidant, wherein at least contains following two substance:
(1) alkylated diphenylamine;(2) it is alkylated N- phenyl-α-naphthylamine.The composite amine antioxidant is the presence in acidic catalyst
Under, diisobutylene is added in diphenylamines and the mixture of N- phenyl-α-naphthylamine and is alkylated what reaction was prepared.The hair
The amine antioxidants of bright offer have good oil-soluble energy and antioxygenic property, can be widely applied in each class lubricating oil.
Antioxidant is that two kinds of aminated compounds are made using same catalyst and alkene addition reaction of the same race in the patent, two kinds of amines
It is different to close object structure, different from olefine reaction temperature, the product composition that this reaction obtains is complex, and product stability is poor.
Chinese patent CN.105733740A provides a kind of amine oligomer antioxidant.The patent antioxidant is by being alkylated
Diphenylamine compound, N- phenyl-α-naphthylamine class compound are synthesized using a variety of oxidation coupling catalyst in organic solvent, should
Patent is reacted using organic plus inorganic composite catalyst agent, and reaction effect is good, and reaction is mild, and product degree of coupling is high, but the party
Method has used low-flash organic solvent, and to avoid risk, reaction temperature is low, and the reaction time is long, at the same post-processing need to evaporate it is molten
Agent, the catalyst that this method uses are organic-inorganic mixed catalyst, and the strong complicated component of acidity of catalyst needs a large amount of water
Remaining acid catalyst is removed, the three wastes generated in production process are more.
Summary of the invention
Technical problem: amine oxidation coupling high temperature antioxygen is more rationally efficiently prepared the purpose of the present invention is to provide a kind of
The preparation method of agent overcomes existing reaction condition complicated, and the reaction time is long, and product yield is low, and the degree of polymerization is low, product stability
The defects of difference, post-processing is difficult.
Technical solution: to achieve the above object, the invention provides the following technical scheme:
A kind of oxidation coupling high-temperature antioxidant non-solvent preparation of the invention, specific preparation process is as follows:
1) N- phenyl-Alpha-Methyl naphthylamines or alkylation N- phenyl-Alpha-Methyl naphthylamines and alkylation are added in the reaction vessel
Diphenylamine compound, molar ratio are 1:0.2~4.0;
2) vacuum is established, 80~160 DEG C of thawing materials are warming up to, opens stirring;
3) oxidation coupling catalyst is added at 80~160 DEG C in reaction temperature, reacts 3~10h;
4) it after reaction, slowly establishes vacuum to 2mmHG column to go, is warming up to 160~200 DEG C, Removal of catalyst obtains
Tan solid product.
Preferably, the oxidation coupling catalyst is dialkyl peroxide, in peroxide lipid, diacyl peroxide
Extremely
Few one kind.
Preferably, the oxidation coupling catalyst is di-tert-butyl peroxide.
Preferably, oxidation coupling catalyst used in reaction process is one kind, oxidation coupling catalyst and alkyl diphenyl
Amine
The molar ratio of compound are as follows: 1:0.2~1.
Preferably, reaction vacuum degree is in 200~300mmHG column.
Preferably, reaction temperature is 120~140 DEG C.
Preferably, Removal of catalyst temperature is 170~180 DEG C.
The utility model has the advantages that compared with prior art, the beneficial effects of the present invention are:
1. preparation method of the present invention use the direct frit reaction of raw material, oxidation coupling catalyst itself play reaction dissolvent and
It is catalyzed double action, without additional addition organic solvent, material is uniformly mixed, and reaction condition is mild, and reaction effect is good.
2. catalyst component used in the method for the present invention is single, the alcohol of one-component is generated after reaction consumption, in negative pressure
Under separated from reactant quickly, can be used as product retail.Organic-inorganic in the post-processing compared with the prior art of product
Mixed catalyst is more simple, and the three wastes are few.
3. catalyst stabilization in preparation method of the present invention, reaction temperature is higher, and the reaction time is short, can effectively improve production effect
Rate.
Detailed description of the invention
Fig. 1 is 2 mass spectrogram of the embodiment of the present invention.
Specific embodiment
The present invention will be further described with reference to the examples below.
A kind of oxidation coupling high-temperature antioxidant non-solvent preparation of the invention, this method preparation step are as follows:
1) N- phenyl-Alpha-Methyl naphthylamines or alkylation N- phenyl-Alpha-Methyl naphthylamines and alkylation are added in the reaction vessel
Diphenylamine compound, molar ratio are 1:0.2~4.0;
2) vacuum is established, 80~160 DEG C of thawing materials are warming up to, opens stirring;
3) oxidation coupling catalyst is added at 80~160 DEG C in reaction temperature, reacts 3~10h;
4) it after reaction, slowly establishes vacuum to 2mmHG column to go, is warming up to 160~200 DEG C, Removal of catalyst obtains
Tan solid product.
Embodiment 1
Using 250ml four-hole boiling flask, it is weighed into 0.075mol, N- phenyl-Alpha-Methyl naphthylamines of 16.425g, 0.075mol,
The P of 29.475g, P di-iso-octyldiphenylamine, four mouthfuls of difference jointing temp meters of flask, condensing reflux pipe, constant pressure titration kit and stirring
Device establishes vacuum 300mmHG column, 80~100 DEG C of reaction temperature, 0.15mol, 36.3g benzoyl peroxide, reaction reflux is added
10h is washed using hot water to neutrality, vacuum distillation obtains dark brown viscous liquid after reaction.
Embodiment 2
Using 250ml four-hole boiling flask, it is weighed into 0.075mol, N- phenyl-Alpha-Methyl naphthylamines of 16.425g, 0.075mol,
The P of 29.475g, P di-iso-octyldiphenylamine, four mouthfuls of difference jointing temp meters of flask, condensing reflux pipe, constant pressure titration kit and stirring
Device establishes vacuum 300mmHG column, and reaction temperature is at 120~140 DEG C, addition 0.15mol, 21.9g di-t-butyl peroxide, instead
Should flow back 3.5h, after reaction, be washed using 20g hot water, and vacuum distillation obtains Tan solid product.
Embodiment 3
Using 250ml four-hole boiling flask, it is weighed into 0.05mol, N- phenyl-Alpha-Methyl naphthylamines of 10.95g, 0.1mol, 39.3g
P, P di-iso-octyldiphenylamine, four mouthfuls of difference jointing temp meters of flask, condensing reflux pipe, constant pressure titration kit and blender are established true
0.2mol is added at 120~140 DEG C in empty 300mmHG column, reaction temperature, and 29.2g di-t-butyl peroxide reacts reflux 4.5h,
After reaction, it is washed using 30g hot water, vacuum distillation obtains Tan solid product.
Embodiment 4
Using 250ml four-hole boiling flask, it is weighed into 0.05mol, N- phenyl-Alpha-Methyl naphthylamines of 10.95g, 0.1mol, 39.3g
P, P di-iso-octyldiphenylamine, four mouthfuls of difference jointing temp meters of flask, condensing reflux pipe, constant pressure titration kit and blender are established true
Empty 300mmHG column, reaction temperature at 80~100 DEG C, be added 0.2mol, 48.4g benzoyl peroxide, reaction reflux 9h, reaction
After, it is washed using hot water to neutrality, is evaporated under reduced pressure to dark brown viscous liquid.
Embodiment 5
Using 250ml four-hole boiling flask, it is weighed into 0.075mol, N- phenyl-Alpha-Methyl naphthylamines of 16.425g, 0.075mol,
The P of 29.475g, P di-iso-octyldiphenylamine, four mouthfuls of difference jointing temp meters of flask, condensing reflux pipe, constant pressure titration kit and stirring
Device establishes vacuum 200mmHG column, and reaction temperature is at 100~120 DEG C, addition 0.15mol, 19.8g tert-butyl peroxy acetate, instead
Should flow back 6h, after reaction, be washed using hot water to neutrality, vacuum distillation obtains Tan solid product.
Embodiment 6
Using 250ml four-hole boiling flask, it is weighed into 0.05mol, N- phenyl-Alpha-Methyl naphthylamines of 10.95g, 0.01mol, 39.3g
P, P di-iso-octyldiphenylamine, four mouthfuls of difference jointing temp meters of flask, condensing reflux pipe, constant pressure titration kit and blender are established true
Empty 200mmHG column, reaction temperature instill 0.2mol at 100~120 DEG C, and 26.4g tert-butyl peroxy acetate reacts reflux 6h, instead
After answering, washed using hot water to neutrality, vacuum distillation obtains Tan solid product.
Originate thermal decomposition temperature test
Examples 1 to 6 product is analyzed using DSC thermogravimetric analyzer, product starting thermal decomposition temperature is obtained and is as follows:
Table 1
Analyzing result according to table 1 can be seen that Examples 1 to 6 product starting thermal decomposition temperature compared with alkyl diphenylamine, N- benzene
Base-α methyl naphthylamines, the starting thermal decomposition temperature for being alkylated N- phenyl Alpha-Methyl naphthylamines are 20~50 DEG C high, wherein embodiment 2, and 5 produce
Product effect is optimal.
Oil viscosity and acid value test
Different embodiment products and existing market product are added in base oil according to identical mass fraction 2%,
Thermo-oxidative ageing is carried out in an oven, and experimental temperature is 200 DEG C, and over time, (100 DEG C of movements are viscous for detection oil viscosity
Degree) and acid value situation of change, as a result such as the following table 2:
Table 2
Note: base oil uses pentaerythritol esters
According to the embodiment 2 and 5 product of embodiment synthesized in the table 1 as the result is shown present invention in pentaerythritol esters base oil
In have excellent high-temperature aging resisting performance.
Product has higher oxidation coupling degree in the present invention, and thermal decomposition temperature is higher, and product is more stable, is suitable for various
In special high temperature lubricating oil product.Compared with prior art, the preparation method cleaning of this patent is simpler, in cleaning without addition
A large amount of organic solvents, byproduct of reaction is single and recyclable, and reaction temperature is high, and the reaction time is short, and inorganic acid is free of in catalyst,
Reaction intermediate fluid does not need a large amount of water washing, small to equipment damage, and the three wastes are few.
The oxidation coupling high-temperature antioxidant prepared by the method for the invention is the polymer mixture of amine antioxidants,
Product is different from the oligomeric coupling AB of the prior art, in the majority with dimer, and reaction temperature is high in the method for the present invention step, reaction interval
Degree is deep, and not only there is A in productmBnThe poly coupling body of form, but also there are Ax, ByThe monomer of form couples form.This
It is more excellent that oxidation coupling high-temperature antioxidant prepared by inventive method is reflected in the result on thermal stability, has higher heat
Decomposition temperature, than existing oligomeric high 10 DEG C of coupling antioxidant thermal decomposition temperature or more.
This method of the present invention uses N- phenyl-α-naphthylamine class compound (PNA), alkylated diphenylamine class compound
(ODPA), under the action of oxidation coupling catalyst, it is coupled into amine polymer, polymer side reaction is few, product effective component
Height is suitable for all kinds of base oils, has splendid high-temperature oxidation resistance, is particularly suitable for aeroengine oil field and high temperature is special
Kind industry oil.
Claims (7)
1. a kind of oxidation coupling high-temperature antioxidant non-solvent preparation, it is characterised in that preparation step is as follows:
1) N- phenyl-Alpha-Methyl naphthylamines or alkylation N- phenyl-Alpha-Methyl naphthylamines and alkylation hexichol are added in the reaction vessel
Aminated compounds, molar ratio are 1:0.2~4.0;
2) vacuum is established, 80~160 DEG C of thawing materials are warming up to, opens stirring;
3) oxidation coupling catalyst is added at 80~160 DEG C in reaction temperature, reacts 3~10h;
4) it after reaction, slowly establishes vacuum to 2mmHG column to go, is warming up to 160~200 DEG C, Removal of catalyst obtains yellowish-brown
Color solid product.
2. a kind of oxidation coupling high-temperature antioxidant non-solvent preparation according to claim 1, which is characterized in that described
Oxidation coupling catalyst is at least one of dialkyl peroxide, peroxide lipid, diacyl peroxide.
3. a kind of oxidation coupling high-temperature antioxidant non-solvent preparation according to claim 1, which is characterized in that described
Oxidation coupling catalyst is di-tert-butyl peroxide.
4. a kind of oxidation coupling high-temperature antioxidant non-solvent preparation according to claim 1, which is characterized in that reaction
Oxidation coupling catalyst used in process is one kind, the molar ratio of oxidation coupling catalyst and alkyl diphenyl amine compound
Are as follows: 1:0.2~1.
5. a kind of oxidation coupling high-temperature antioxidant non-solvent preparation according to claim 1, which is characterized in that reaction
Vacuum degree is in 200~300mmHG column.
6. a kind of oxidation coupling high-temperature antioxidant non-solvent preparation according to claim 1, which is characterized in that reaction
Temperature is 120~140 DEG C.
7. a kind of oxidation coupling high-temperature antioxidant non-solvent preparation according to claim 1, which is characterized in that removing
Catalyst temperature is 170~180 DEG C.
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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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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN114426901A (en) * | 2022-01-21 | 2022-05-03 | 中国石油化工股份有限公司 | High-temperature antioxidant solution and preparation method thereof |
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 antioxidant and preparation method thereof |
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- 2019-04-12 CN CN201910291587.9A patent/CN109942435B/en active Active
- 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 antioxidant and preparation method thereof |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114426901A (en) * | 2022-01-21 | 2022-05-03 | 中国石油化工股份有限公司 | High-temperature antioxidant solution 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 |