CN101684125B - Fluorine-containing silicon carbon hydrogen compound and preparation method thereof - Google Patents
Fluorine-containing silicon carbon hydrogen compound and preparation method thereof Download PDFInfo
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- CN101684125B CN101684125B CN2008102316361A CN200810231636A CN101684125B CN 101684125 B CN101684125 B CN 101684125B CN 2008102316361 A CN2008102316361 A CN 2008102316361A CN 200810231636 A CN200810231636 A CN 200810231636A CN 101684125 B CN101684125 B CN 101684125B
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- methyl trifluoro
- trifluoro propyl
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Abstract
The invention discloses a fluorine-containing silicon carbon hydrogen compound and a preparation method thereof. The method synthesizes the novel fluorine-containing silicon carbon hydrogen compound, and the chemical name of the compound is bis(3-alkyl propyl silicon) methyl trifluoro-propyl silane and is represented by a molecular structural formula (I). The compound has good low-temperature characteristics, high viscosity index, high thermal decomposition temperature and better tribological properties, and can be used as lubricant of a moving part such as a bearing of a space satellite scanning mechanism and the like.
Description
Technical field
The present invention relates to a kind of fluorine silicon hydrocarbon polymer and preparation method thereof.
Background technology
Along with development of aviation and aerospace technology; Had higher requirement with machinery long lifetime, high reliability in the space; The inefficacy of space mechanism moving parts becomes the bottleneck problem that further develops of restriction spacecraft, therefore, the lubrication technology research of space motion parts is significant.Though airship or satellite can adopt solid lubricant film, soft metal coating, railway grease to lubricate, in general, surpass the space mechanism in 1 year work-ing life, and major part all has liquid lubrication means.Explore the liquid lubricant that has utmost point low-vapor pressure, high thermal stability and a good low-temperature fluidity with development and become one of gordian technique of space vehicle and aircraft security reliability service.
U.S. NASA result of study report, the silicon hydrocarbon compound is the unit molecule compound that comprises silicon, carbon and protium in the molecule structure.Result of study shows; Compare with synthetic hydrocarbon oil with MO; The silicon hydrocarbon compound has and has high temperature performance preferably preferably, and low volatility and viscosity temperature characteristic preferably are expected to become the novel aq lubricant that future space machinery is used under coldcondition.
Generally speaking; Fluorinated organic compound all has good lubricating property; Therefore if active element F is incorporated in the silicon hydrocarbon compound, then can improve the lubricity of silicon hydrocarbon, resulting fluorine silicon hydrocarbon polymer also has the excellent properties of silicon hydrocarbon oil itself simultaneously.
Summary of the invention
The object of the present invention is to provide a kind of fluorine silicon hydrocarbon polymer and Preparation Method thereof.
The present invention has synthesized a kind of new fluorine silicon hydrocarbon polymer, and chemical name is two (trialkyl propyl group silicon) methyl trifluoro propyl silane, and molecular structure is represented with formula (I)
When R is C
8H
17The time, chemical name is two (trioctylphosphine propyl group silicon) methyl trifluoro propyl silane, is abbreviated as SiFC
8H; When R is C
10H
21, chemical name is two (three decyl propyl group silicon) methyl trifluoro propyl silane, is abbreviated as SiFC
10H.
Institute's synthetic two (trioctylphosphine propyl group silicon) methyl trifluoro propyl silane compound is colourless or weak yellow liquid, and density (25 ℃) is 0.8874, and viscosity (25 ℃) is 67mm
2/ s, zero pour is less than-55 ℃; Two (three decyl propyl group silicon) methyl trifluoro propyl silane compound is colourless or weak yellow liquid, and density (25 ℃) is 0.8783, and viscosity (25 ℃) is 100mm
2/ s, zero pour is less than-55 ℃.
The synthetic of two (trialkyl propyl group silicon) methyl trifluoro propyl silane compound involved in the present invention can be represented with following chemical equation:
The compound method of compound may further comprise the steps:
A, through the reaction of methyl trifluoro propyl dichlorosilane and propenyl magnesium bromide, generation methyl trifluoro propyl diallyl silane;
B, methyl trifluoro propyl diallyl silane and trialkyl hydrogen silane are mixed according to stoichiometric ratio, add H
2PtCl
6Mass percent concentration be 4.3% H
2PtCl
6-PhNMe
2Solution catalyzing carries out addition reaction, H
2PtCl
6-PhNMe
2The dripping quantity of solution is 0.1%～0.3% of a methyl trifluoro propyl diallyl silane quality; Temperature of reaction is 90 ℃～100 ℃, and the reaction times is 10～15 days, generates title product two (trialkyl propyl group silicon) methyl trifluoro propyl silane;
C, will react gained compound after removing by filter catalyzer, be heated to 230-250 ℃, and under 2mmHg vacuum tightness, distill, remove lighting end wherein, promptly obtain required target compound.
Fluorine silicon hydrocarbon polymer through the present invention preparation has excellent cold property, high viscosity index (HVI) and high heat decomposition temperature and tribological property preferably, and the lubricating oil that can be used as moving partss such as Aerospace Satellite scanning mechanism bearing uses.
Embodiment
Below in conjunction with specific embodiment the present invention is elaborated:
Embodiment 1:
The synthetic of two (trioctylphosphine propyl group silicon) methyl trifluoro propyl silane (is abbreviated as SiFC
8H):
A, methyl trifluoro propyl diallyl silane synthetic: get in the anhydrous ether solution that bromopropylene (150g) is added dropwise to Mg (30g) and produce propenyl magnesium bromide Grignard reagent.Afterwards the above-mentioned Grignard reagent that obtains is added dropwise in the anhydrous ether solution of methyl trifluoro propyl dichlorosilane (105g).Reaction slowly adds the entry stopped reaction after finishing.The magnesium salts that the filtering reaction generates washs magnesium salts three times with anhydrous ether solution, and merging filtrate is removed ether, and underpressure distillation obtains title product, and IR spectroscopy confirms that title product is a methyl trifluoro propyl diallyl silane, is colourless liquid.
B, addition reaction:
Get trioctylphosphine hydrogen silane (110g) and methyl trifluoro propyl diallyl silane (25g), put into 500ml single port bottle, drip 4.3% the H configure
2PtCl
6-PhNMe
2Solution 0.5g is warming up to 90 ℃～100 ℃, reacts 10～15 days.Monitor with ir spectra therebetween, till the two key charateristic avsorption bands of methyl trifluoro propyl diallyl silane disappeared, proved response finished.
C, separation are purified:
With the reaction gained compound after removing by filter catalyzer; Be heated to 230-250 ℃, and under the vacuum tightness of about 2mmHg left and right sides, distill, remove lighting end wherein; Promptly obtain required target compound two (trioctylphosphine propyl group silicon) methyl trifluoro propyl silane; Be weak yellow liquid, density (25 ℃) is 0.8874, and viscosity (25 ℃) is 67mm
2/ s, zero pour is less than-55 ℃.
Embodiment 2:
The synthetic of two (three decyl propyl group silicon) methyl trifluoro propyl silane (is abbreviated as SiFC
10H):
Methyl trifluoro propyl diallyl silane is synthetic with embodiment 1, gets three decyl hydrogen silanes (118g) and methyl trifluoro propyl diallyl silane (25g), puts into 500ml single port bottle, 4.3% the H that dropping configures
2PtCl
6-PhNMe
2Solution 0.6g is warming up to 90 ℃～100 ℃, reacts 10～15 days.Monitor with ir spectra therebetween, till the two key charateristic avsorption bands of methyl trifluoro propyl diallyl silane disappeared, proved response finished.
The compound process of reaction gained is purified with embodiment 1 described method, promptly obtain required target compound two (three decyl propyl group silicon) methyl trifluoro propyl silane, be weak yellow liquid, density (25 ℃) is 0.8874, and viscosity (25 ℃) is 67mm
2/ s, zero pour is less than-55 ℃.
Through above technology implementation scheme, two kinds of fluorine silicon hydrocarbon polymers of synthetic have good low-temperature performance and very high viscosity index, and its part physicochemical property is as shown in table 1.
The basic physicals of table 1. two (trialkyl propyl group silicon) methyl trifluoro propyl silane
Two kinds of fluorine silicon hydrocarbon polymers that the present invention synthesizes; Through SRV micro-moving frictional wear experimental test; Test-results is as shown in table 2, can find, as steel-steel lubricant; Compare with four (three decyl silicon) tetrapropyl silane (being abbreviated as SiCH) and polyalphaolefin (being abbreviated as PAO), two kinds of fluorine silicon hydrocarbon polymers have antiwear and friction reduction property and advantages of high bearing capacity relatively preferably.
Table 2, SRV fine motion rub(bing)test result (steel-steel, frequency 25Hz, 30min, room temperature)
"-" friction was lost efficacy
Claims (3)
1. fluorine silicon hydrocarbon polymer, chemical name is two (trialkyl propyl group silicon) methyl trifluoro propyl silane, molecular structure is represented with formula (I)
2. the preparation method of fluorine silicon hydrocarbon polymer according to claim 1 is characterized in that this method may further comprise the steps:
A, methyl trifluoro propyl diallyl silane synthetic: get in the anhydrous ether solution that bromopropylene 150g is added dropwise to 30g Mg and produce propenyl magnesium bromide Grignard reagent; Afterwards the above-mentioned Grignard reagent that obtains is added dropwise in the anhydrous ether solution of 105g methyl trifluoro propyl dichlorosilane; Reaction slowly adds the entry stopped reaction after finishing; The magnesium salts that the filtering reaction generates washs magnesium salts three times with anhydrous ether solution, and merging filtrate is removed ether, and underpressure distillation obtains title product, and IR spectroscopy confirms that title product is a methyl trifluoro propyl diallyl silane, is colourless liquid;
B, addition reaction:
Get 110g trioctylphosphine hydrogen silane and 25g methyl trifluoro propyl diallyl silane, put into 500ml single port bottle, drip 4.3% the H configure
2PtCl
6-PhNMe
2Solution 0.5g is warming up to 90 ℃～100 ℃, reacts 10～15 days; Monitor with ir spectra therebetween, till the two key charateristic avsorption bands of methyl trifluoro propyl diallyl silane disappeared, proved response finished;
C, separation are purified:
With the reaction gained compound after removing by filter catalyzer; Be heated to 230-250 ℃, and under 2mmHg vacuum tightness, distill, remove lighting end wherein; Obtain target compound two (trioctylphosphine propyl group silicon) methyl trifluoro propyl silane; Being weak yellow liquid, is 0.8874 under 25 ℃ of the density, and viscosity is 67mm down for 25 ℃
2/ s, zero pour is less than-55 ℃.
3. the preparation method of fluorine silicon hydrocarbon polymer according to claim 1 is characterized in that this method may further comprise the steps:
A, methyl trifluoro propyl diallyl silane synthetic: get in the anhydrous ether solution that bromopropylene 150g is added dropwise to 30g Mg and produce propenyl magnesium bromide Grignard reagent; Afterwards the above-mentioned Grignard reagent that obtains is added dropwise in the anhydrous ether solution of 105g methyl trifluoro propyl dichlorosilane; Reaction slowly adds the entry stopped reaction after finishing; The magnesium salts that the filtering reaction generates washs magnesium salts three times with anhydrous ether solution, and merging filtrate is removed ether, and underpressure distillation obtains title product, and IR spectroscopy confirms that title product is a methyl trifluoro propyl diallyl silane, is colourless liquid;
B, addition reaction: get 118g three decyl hydrogen silanes and 25g methyl trifluoro propyl diallyl silane, put into 500ml single port bottle, drip 4.3% the H configure
2PtCl
6-PhNMe
2Solution 0.6g is warming up to 90 ℃～100 ℃, reacts 10～15 days; Monitor with ir spectra therebetween, till the two key charateristic avsorption bands of methyl trifluoro propyl diallyl silane disappeared, proved response finished;
C, separation are purified:
With the reaction gained compound after removing by filter catalyzer; Be heated to 230-250 ℃, and under 2mmHg vacuum tightness, distill, remove lighting end wherein; Obtain target compound two (three decyl propyl group silicon) methyl trifluoro propyl silane; Being weak yellow liquid, is 0.8874 under 25 ℃ of the density, and viscosity is 67mm down for 25 ℃
2/ s, zero pour is less than-55 ℃.
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| CN2008102316361A CN101684125B (en) | 2008-09-26 | 2008-09-26 | Fluorine-containing silicon carbon hydrogen compound and preparation method thereof |
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| CN2008102316361A CN101684125B (en) | 2008-09-26 | 2008-09-26 | Fluorine-containing silicon carbon hydrogen compound and preparation method thereof |
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| CN101684125B true CN101684125B (en) | 2012-02-29 |
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| CN113736536A (en) * | 2020-05-28 | 2021-12-03 | 中国石油化工股份有限公司 | Silicon hydrocarbon lubricating oil composition and preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308393A (en) * | 1980-10-08 | 1981-12-29 | E. I. Du Pont De Nemours And Company | Fluorine containing organosilicon compounds |
| EP0465177A1 (en) * | 1990-06-29 | 1992-01-08 | Shin-Etsu Chemical Co., Ltd. | Fluorine-containing organic silicon compounds |
| CN1180706A (en) * | 1996-10-26 | 1998-05-06 | 希尔斯股份公司 | Process for preparing fluoroalkyl-containing organosilicon compounds and their use |
| CN1456564A (en) * | 2003-05-28 | 2003-11-19 | 中国科学院上海有机化学研究所 | Mixed fluorinated cyclosiloxane, preparing method and use thereof |
| CN1461764A (en) * | 2002-05-29 | 2003-12-17 | 黄振宏 | Organic poly-molecular polymer containing fluorine, silicon and its production technology |
-
2008
- 2008-09-26 CN CN2008102316361A patent/CN101684125B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308393A (en) * | 1980-10-08 | 1981-12-29 | E. I. Du Pont De Nemours And Company | Fluorine containing organosilicon compounds |
| EP0465177A1 (en) * | 1990-06-29 | 1992-01-08 | Shin-Etsu Chemical Co., Ltd. | Fluorine-containing organic silicon compounds |
| CN1180706A (en) * | 1996-10-26 | 1998-05-06 | 希尔斯股份公司 | Process for preparing fluoroalkyl-containing organosilicon compounds and their use |
| CN1461764A (en) * | 2002-05-29 | 2003-12-17 | 黄振宏 | Organic poly-molecular polymer containing fluorine, silicon and its production technology |
| CN1456564A (en) * | 2003-05-28 | 2003-11-19 | 中国科学院上海有机化学研究所 | Mixed fluorinated cyclosiloxane, preparing method and use thereof |
Non-Patent Citations (1)
| Title |
|---|
| 李战雄等.合成氟硅润滑油的新方法.《有机硅材料》.2006,第20卷(第6期), * |
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