CN114957671A - High-temperature methyl silicone oil and preparation method and application thereof - Google Patents
High-temperature methyl silicone oil and preparation method and application thereof Download PDFInfo
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- CN114957671A CN114957671A CN202210445989.1A CN202210445989A CN114957671A CN 114957671 A CN114957671 A CN 114957671A CN 202210445989 A CN202210445989 A CN 202210445989A CN 114957671 A CN114957671 A CN 114957671A
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/398—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing boron or metal atoms
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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
- C10M155/00—Lubricating compositions characterised by the additive being a macromolecular compound containing atoms of elements not provided for in groups C10M143/00 - C10M153/00
- C10M155/02—Monomer containing silicon
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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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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Abstract
The invention provides high-temperature methyl silicone oil which has a structure shown in a formula I; in the formula I, m + n is 45-850. The invention provides a preparation method of high-temperature methyl silicone oil, which comprises the following steps: under the action of a catalyst, carrying out polymerization reaction on a methyl silicone oil monomer and low-molecular-weight methyl silicone oil to obtain a polymer; and reacting the polymer with organic iron to obtain the high-temperature methyl silicone oil. The high-temperature methyl silicone oil provided by the invention has excellent high-temperature performance, viscosity-temperature performance and low-temperature performance, the initial oxidation temperature is above 330 ℃, and the high-temperature methyl silicone oil has a good industrial application prospect. The present invention also provides a lubricant comprising: high-temperature methyl silicone oil.
Description
Technical Field
The invention belongs to the technical field of methyl silicone oil, and particularly relates to high-temperature methyl silicone oil and a preparation method and application thereof.
Background
Methyl silicone oil is an organic polymer formed by combining an inorganic silica main chain and a methyl branch chain, wherein the main chain is of a silicon-oxygen-silicon (Si-O-Si) structure, and the Si-O bond energy is 460kJ/mol and is higher than the C-C bond energy (348kJ/mol), so that the methyl silicone oil has more excellent heat resistance than other organic polymers. However, the methyl silicone oil can only be used in an open system at the temperature of-50-180 ℃ for a long time, and when the use temperature exceeds 200 ℃, the oxidation reaction is easy to generate gel, so that the service life is greatly shortened. Although the introduction of phenyl groups into the silicone oil molecule can raise the use temperature to 250 ℃, the viscosity-temperature coefficient is correspondingly increased, and the condensation point is increased.
With the continuous advance of industrial development, the application field of high-temperature-resistant oil products is continuously expanded, the use requirements on high-temperature heat conduction oil are increased in emerging development fields such as solar photo-thermal power generation and the like besides the traditional industry, and the requirements on the use temperature, the service life and the like of the oil products are further improved. The high-temperature methyl silicone oil which has excellent high-temperature performance, viscosity-temperature performance and low-temperature performance and is low in cost is provided for the market, and the high-temperature methyl silicone oil has extremely important significance.
Disclosure of Invention
In view of the above, the present invention aims to provide a high temperature methyl silicone oil, and a preparation method and an application thereof, and the high temperature methyl silicone oil provided by the present invention has excellent high temperature performance, viscosity temperature performance and low temperature performance, and is low in cost.
The invention provides high-temperature methyl silicone oil which has a structure shown in a formula I:
in the formula I, m + n is 45-850.
Preferably, the kinematic viscosity of the high-temperature methyl silicone oil is 50-10000 mm 2 /s。
The invention provides a preparation method of high-temperature methyl silicone oil, which comprises the following steps:
under the action of a catalyst, carrying out polymerization reaction on a methyl silicone oil monomer and low molecular weight methyl silicone oil to obtain a polymer;
and reacting the polymer with organic iron to obtain the high-temperature methyl silicone oil.
Preferably, the catalyst is tetramethylammonium hydroxide.
Preferably, the methyl silicone oil monomer is selected from octamethylcyclotetrasiloxane and/or dimethylcyclosiloxane.
Preferably, the low molecular weight methyl silicone oil has the structure of formula II:
(CH 3 ) 3 SiO(Si(CH 3 ) 2 O) x Si(CH 3 ) 3 in the formula II, the compound is shown in the specification,
in the formula II, x is 3-7.
Preferably, the organic iron is selected from one or more of ferrocene and organic iron.
Preferably, the iron organic acid is selected from iron alkyl acid.
Preferably, the polymerization reaction further comprises, after completion:
heating the decomposition catalyst;
the method also comprises the following steps after the reaction of the polymer and the organic iron is finished:
and distilling the obtained reaction product to obtain the high-temperature methyl silicone oil.
The present invention provides a lubricant comprising: the high-temperature methyl silicone oil in the technical scheme or the high-temperature methyl silicone oil prepared by the method in the technical scheme.
The high-temperature methyl silicone oil provided by the invention has excellent high-temperature performance, viscosity-temperature performance and low-temperature performance, the initial oxidation temperature is above 330 ℃, and the high-temperature methyl silicone oil has a good industrial application prospect.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides high-temperature methyl silicone oil which has a structure shown in a formula I:
in the formula I, m + n is 45-850.
In the invention, the m + n is preferably 100-800, more preferably 200-700, more preferably 300-600, and most preferably 400-500.
In the invention, the kinematic viscosity of the high-temperature methyl silicone oil is preferably 50-10000 mm 2 S, more preferably 100 to 9000mm 2 (ii) s, more preferably 500 to 8000mm 2 (ii)/s, more preferably 1000 to 8000mm 2 (ii)/s, more preferably 2000 to 6000mm 2 More preferably 3000 to 5000 mm/s 2 S, most preferably 4000mm 2 /s。
The invention provides a preparation method of high-temperature methyl silicone oil, which comprises the following steps:
under the action of a catalyst, carrying out polymerization reaction on a methyl silicone oil monomer and low-molecular-weight methyl silicone oil to obtain a polymer;
and reacting the polymer with organic iron to obtain the high-temperature methyl silicone oil.
In the present invention, the catalyst is preferably tetramethylammonium hydroxide.
In the present invention, the methyl silicone oil monomer is preferably selected from octamethylcyclotetrasiloxane and/or dimethylcyclosiloxane (dimethylsiloxane mixed ring body).
In the present invention, the low molecular weight methyl silicone oil preferably has the structure of formula II:
(CH 3 ) 3 SiO(Si(CH 3 ) 2 O) x Si(CH 3 ) 3 in the formula II, the compound is shown in the specification,
in the formula II, x is 3-7.
In the invention, x is preferably 4-6, and more preferably 5.
In the present invention, the method for preparing the low molecular weight methyl silicone oil preferably comprises:
under the action of an acid catalyst, methyl silicone oil and hexamethyldisiloxane react to obtain low-molecular-weight methyl silicone oil.
In the present invention, the acidic catalyst is preferably an inorganic liquid acid, more preferably sulfuric acid, and more preferably concentrated sulfuric acid.
In the present invention, the methyl silicone oil is preferably selected from octamethylcyclotetrasiloxane and/or dimethylcyclosiloxane (dimethylsiloxane mixed ring body).
In the invention, the mass ratio of the methyl silicone oil to the hexamethyldisiloxane is preferably (1.8-2.2): 1, more preferably 2: 1; the ratio of the mass of the acidic catalyst to the total mass of the (methyl silicone oil and hexamethyldisiloxane) is preferably (0.03-0.06): 1, more preferably (0.04 to 0.05): 1.
in the invention, the reaction temperature is preferably 20-40 ℃, more preferably 25-35 ℃, and most preferably 30 ℃; the reaction time is preferably 6 to 10 hours, more preferably 7 to 9 hours, and most preferably 8 hours.
In the present invention, the reaction preferably further comprises, after completion of the reaction:
removing the acid catalyst from the obtained reaction product, and washing.
In the present invention, the washing is preferably water, more preferably distilled water; the number of washing is preferably 2 to 4, and more preferably 3.
In the present invention, the mass ratio of the methyl silicone oil monomer to the low molecular weight methyl silicone oil is preferably 1: (0.001 to 0.1), more preferably 1: (0.01 to 0.08), more preferably 1: (0.03-0.06), most preferably 1: (0.04-0.05).
In the present invention, the ratio of the mass of the catalyst to the total mass of (methyl silicone oil monomer + low molecular weight methyl silicone oil) is preferably (0.0005 to 0.002): 1, more preferably (0.001 to 0.0015): 1, most preferably (0.0012-0.0013): 1.
in the invention, the temperature of the polymerization reaction is preferably 115-125 ℃, more preferably 118-122 ℃, and most preferably 120 ℃; the time of the polymerization reaction is preferably 6 to 8 hours, more preferably 6.5 to 7.5 hours, and most preferably 7 hours.
In the present invention, it is preferable that the polymerization reaction further comprises, after completion of the polymerization reaction:
the decomposition catalyst is heated.
In the invention, the temperature of the heating decomposition catalyst is preferably 125-165 ℃, more preferably 130-160 ℃, and most preferably 140-150 ℃; the time for heating the decomposition catalyst is preferably 1-3 h, more preferably 1.5-2.5 h, and most preferably 2 h.
In the invention, the organic iron is preferably selected from one or more of ferrocene and organic iron; the organic iron is preferably selected from iron alkyls, more preferably from iron isooctanoate.
In the present invention, the mass ratio of the polymer to the organic iron is preferably 1: (0.05 to 0.15), more preferably 1: (0.08 to 0.12), most preferably 1: 0.1.
in the invention, the temperature for the reaction of the polymer and the organic iron is preferably 200-280 ℃, more preferably 210-270 ℃, more preferably 220-260 ℃, more preferably 230-250 ℃, and most preferably 240 ℃; the reaction time of the polymer and the organic iron is preferably 0.5-2.5 h, more preferably 1-2 h, and most preferably 1.5 h.
In the present invention, it is preferable that the reaction between the polymer and the organic iron is completed by further comprising:
and distilling the obtained reaction product to obtain the high-temperature methyl silicone oil.
In the present invention, the light ends are removed by distillation.
In the invention, the distillation temperature is preferably 300-310 ℃, and more preferably 305 ℃; the distillation pressure is preferably-0.096 MPa to-0.099 MPa, and more preferably-0.097 MPa to-0.098 MPa; the distillation time is preferably 2.0-2.5 h, more preferably 2.1-2.4 h, and most preferably 2.2-2.3 h.
The present invention provides a lubricant comprising: the high-temperature methyl silicone oil in the technical scheme or the high-temperature methyl silicone oil prepared by the method in the technical scheme.
The high-temperature methyl silicone oil provided by the invention has excellent high-temperature performance, viscosity-temperature performance and low-temperature performance, the initial oxidation temperature is above 330 ℃, and the high-temperature methyl silicone oil has a good industrial application prospect.
The dimethyl siloxane mixed ring body used in the following embodiment of the invention is DMC provided by Lucy chemical industry; octamethylcyclotetrasiloxane is D4 supplied by the seiko silicone factory in the west of the river.
The low molecular weight methyl silicone oil is prepared according to the following method:
reacting 200g of octamethylcyclotetrasiloxane and 100g of hexamethyldisiloxane at 25-35 ℃ for 8h by using concentrated sulfuric acid as a catalyst, removing acid water, washing for 3 times by using distilled water, and removing water to obtain the low-molecular-weight methyl silicone oil. The kinematic viscosity of the low molecular weight methyl silicone oil at 25 ℃ is 3.30mm 2 /s。
Example 1
450g of octamethylcyclotetrasiloxane and 50g of low-molecular-weight methylsilicone oil ((CH) 3 ) 3 SiO(Si(CH 3 ) 2 O) x Si(CH 3 ) 3 And x is 5) and 0.5g of tetramethylammonium hydroxide are added into a three-neck flask, the mixture is reacted for 6 hours at 110-120 ℃, the temperature is raised to 135-145 ℃ for decomposing catalyst for 1 hour, 0.5g of ferrocene is added, the mixture is reacted for 1.5 hours at 220-230 ℃, the temperature is raised to 300-310 ℃ under the vacuum degree of-0.098 MPa, and light fractions are removed for 1 hour, so that the high-temperature methyl silicone oil is obtained.
Example 2
490g of octamethylcyclotetrasiloxane and 10g of low-molecular-weight methylsilicone oil ((CH) 3 ) 3 SiO(Si(CH 3 ) 2 O) x Si(CH 3 ) 3 X is 5) and 1.0g of tetramethylammonium hydroxide are added into a three-necked flask, the mixture is reacted for 8 hours at the temperature of 110-120 ℃, the temperature is increased to 135-145 ℃ for decomposing catalyst for 2 hours, 0.75g of iron isooctanoate is added, the mixture is reacted for 1 hour at the temperature of 240-250 ℃, the temperature is increased to 310-320 ℃ under the vacuum degree of-0.098 MPa, and light fractions are removed for 1.5 hours, so that the high-temperature methyl silicone oil is obtained.
Example 3
485g of a mixed ring of dimethylsiloxane and 15g of low molecular weight methylsilicone oil ((CH) 3 ) 3 SiO(Si(CH 3 ) 2 O) x Si(CH 3 ) 3 X is 5) and 0.75g of tetramethylammonium hydroxide are added into a three-necked flask, the mixture is reacted for 7 hours at the temperature of 110-120 ℃, the temperature is increased to 145-155 ℃ for decomposition catalyst for 1.5 hours, 0.75g of ferrocene is added, the mixture is reacted for 0.5 hour at the temperature of 250-260 ℃, the temperature is increased to 310-330 ℃ under the vacuum degree of-0.098 MPa, and light fractions are removed for 1 hour, so that high-temperature methyl silicone oil is obtained.
Performance detection
The kinematic viscosity and the initial oxidation temperature of the high-temperature methyl silicone oil prepared by the embodiment of the invention are detected, and the detection method of the kinematic viscosity comprises the following steps: GB/T265 petroleum products kinematic viscosity determination and kinetic viscosity calculation; the onset oxidation temperature was determined by high Pressure Differential Scanning Calorimetry (PDSC).
The detection result is as follows:
| item | Example 1 | Example 2 | Example 3 | No. 100 methyl silicone oil |
| Kinematic viscosity (25 ℃), mm 2 /s | 99.80 | 1503 | 998.4 | 99.90 |
| Initial oxidation temperature,. degree.C | 338.5 | 354.9 | 345.2 | 284.8 |
The high-temperature methyl silicone oil provided by the invention has excellent high-temperature performance, viscosity-temperature performance and low-temperature performance, the initial oxidation temperature is above 330 ℃, and the high-temperature methyl silicone oil has a good industrial application prospect.
While the invention has been described and illustrated with reference to specific embodiments thereof, such description and illustration are not intended to limit the invention. It will be clearly understood by those skilled in the art that various changes in form and details may be made therein without departing from the true spirit and scope of the invention as defined by the appended claims, to adapt a particular situation, material, composition of matter, substance, method or process to the objective, spirit and scope of this application. All such modifications are intended to be within the scope of the claims appended hereto. Although the methods disclosed herein have been described with reference to particular operations performed in a particular order, it should be understood that these operations may be combined, sub-divided, or reordered to form equivalent methods without departing from the teachings of the present disclosure. Accordingly, unless specifically indicated herein, the order and grouping of the operations is not a limitation of the present application.
Claims (10)
1. A high temperature methyl silicone oil having the structure of formula I:
in the formula I, m + n is 45-850.
2. A high-temperature methyl silicone oil according to claim 1, wherein the kinematic viscosity of the high-temperature methyl silicone oil is 50 to 10000mm 2 /s。
3. A preparation method of high-temperature methyl silicone oil comprises the following steps:
under the action of a catalyst, carrying out polymerization reaction on a methyl silicone oil monomer and low-molecular-weight methyl silicone oil to obtain a polymer;
and reacting the polymer with organic iron to obtain the high-temperature methyl silicone oil.
4. The method of claim 3, wherein the catalyst is tetramethylammonium hydroxide.
5. A method according to claim 3, wherein the methyl silicone oil monomer is selected from octamethylcyclotetrasiloxane and/or dimethylcyclosiloxane.
6. The method according to claim 3, wherein the low molecular weight methyl silicone oil has the formula II:
(CH 3 ) 3 SiO(Si(CH 3 ) 2 O) x Si(CH 3 ) 3 in the formula II, the compound is shown in the specification,
in the formula II, x is 3-7.
7. The method according to claim 3, wherein the organic iron is selected from one or more of ferrocene and organic iron.
8. The method according to claim 7, wherein the iron organic acid is selected from iron alkyl acid.
9. The method of claim 3, further comprising, after completion of the polymerization reaction:
heating the decomposition catalyst;
the method also comprises the following steps after the reaction of the polymer and the organic iron is finished:
and distilling the obtained reaction product to obtain the high-temperature methyl silicone oil.
10. A lubricant, comprising: the high temperature methyl silicone oil of claim 1, or the high temperature methyl silicone oil prepared by the method of claim 3.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3865784A (en) * | 1973-12-05 | 1975-02-11 | Union Carbide Corp | Stabilized organosilicon polymers |
| JPH0273895A (en) * | 1988-09-09 | 1990-03-13 | Tonen Corp | Silicone oil composition excellent in heat-resistant stability |
| CN106146853A (en) * | 2016-06-30 | 2016-11-23 | 东莞市贝特利新材料有限公司 | LED liquid casting glue heat-resistant agent and preparation method thereof |
| CN108610484A (en) * | 2018-05-25 | 2018-10-02 | 广州盛泰诺新材料科技有限公司 | A kind of thermostable transparent methyl-silicone oil and its synthetic method |
| CN110484197A (en) * | 2019-08-23 | 2019-11-22 | 武汉双键开姆密封材料有限公司 | A kind of preparation method of room curing and high temperature resistant silicone adhesives |
| CN111320755A (en) * | 2020-04-24 | 2020-06-23 | 中国石油化工股份有限公司 | Polytitanosiloxane and preparation method thereof |
-
2022
- 2022-04-26 CN CN202210445989.1A patent/CN114957671A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3865784A (en) * | 1973-12-05 | 1975-02-11 | Union Carbide Corp | Stabilized organosilicon polymers |
| JPH0273895A (en) * | 1988-09-09 | 1990-03-13 | Tonen Corp | Silicone oil composition excellent in heat-resistant stability |
| CN106146853A (en) * | 2016-06-30 | 2016-11-23 | 东莞市贝特利新材料有限公司 | LED liquid casting glue heat-resistant agent and preparation method thereof |
| CN108610484A (en) * | 2018-05-25 | 2018-10-02 | 广州盛泰诺新材料科技有限公司 | A kind of thermostable transparent methyl-silicone oil and its synthetic method |
| CN110484197A (en) * | 2019-08-23 | 2019-11-22 | 武汉双键开姆密封材料有限公司 | A kind of preparation method of room curing and high temperature resistant silicone adhesives |
| CN111320755A (en) * | 2020-04-24 | 2020-06-23 | 中国石油化工股份有限公司 | Polytitanosiloxane and preparation method thereof |
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