CN112457497A - Preparation method of long-chain alkyl modified hydrogen-containing silicone oil lubricating oil - Google Patents
Preparation method of long-chain alkyl modified hydrogen-containing silicone oil lubricating oil Download PDFInfo
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- CN112457497A CN112457497A CN202011221728.9A CN202011221728A CN112457497A CN 112457497 A CN112457497 A CN 112457497A CN 202011221728 A CN202011221728 A CN 202011221728A CN 112457497 A CN112457497 A CN 112457497A
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- silicone oil
- hydrogen
- containing silicone
- chain alkyl
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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
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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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound 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
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
- C10M2229/0415—Siloxanes with specific structure containing aliphatic substituents used as base material
Abstract
A preparation method of long-chain alkyl modified hydrogen-containing silicone oil lubricating oil comprises the following steps: adding hydrogen-containing silicone oil into a reaction kettle, heating to 60-70 ℃ under stirring, dropwise adding a mixture of dodecene, a Speier catalyst and an amine compound, controlling the dropwise adding time to be 15-30 min, and reacting for 4-8 h at 90-130 ℃ after dropwise adding; and carrying out vacuum reduced pressure distillation on the obtained product, and removing low boiling point to obtain the long-chain alkyl modified hydrogen-containing silicone oil lubricating oil. The lubricating oil prepared by the process has the advantages of simple process, easy operation, high efficiency, good quality and the like.
Description
Technical Field
The invention relates to a preparation method of long-chain alkyl modified hydrogen-containing silicone oil lubricating oil.
Background
The long-chain alkyl modified hydrogen-containing silicone oil lubricating oil is modified silicone oil prepared by grafting long-chain alkyl on a side chain of hydrogen-containing silicone oil. The modified silicone oil has new characteristics on the basis of keeping the characteristics of the conventional methyl silicone oil, optimizes the compatibility and lubricating property of the modified silicone oil with organic matters, and is widely applied to the fields of metal die casting demoulding, plastic demoulding, defoaming agents and the like. When the release agent is used as a release agent, the release agent does not generate chemical reaction with a finished product, is adhered to a mould without being transferred to a processed product, and does not interfere with the painting or secondary processing of the finished product.
The route of the prior art is as follows: 1. tetramethyl hydrogen cyclo-tetrasiloxane is used as a raw material, long-chain alkyl is added to form a mixed ring body, and ring opening telomerization is carried out by an acid catalyst to obtain the catalyst.
The drawbacks of this route are: the raw material tetramethylhydrocyclotetrasiloxane is expensive, and although the product can effectively control molecular weight and viscosity, and has good performance, the cost is high in large-scale production and sale, and the price advantage cannot be formed.
2. The preparation method comprises the steps of taking hydrogen-containing silicone oil and dodecene as raw materials, and carrying out silicon-hydrogen addition reaction by using a Speier catalyst to prepare a product.
The drawbacks of this route are: the Speier catalyst is a homogeneous catalyst, has good catalytic effect, but has large using amount and high cost, is easy to cause olefin isomerization side reaction, silicon-hydrogen crosslinking and product color yellowing, and lacks competitiveness in application in high-end markets.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides the preparation method of the long-chain alkyl modified hydrogen-containing silicone oil lubricating oil, which has the advantages of simple process, easy operation, high efficiency, good quality and the like.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a preparation method of long-chain alkyl modified hydrogen-containing silicone oil lubricating oil comprises the following steps: adding hydrogen-containing silicone oil into a reaction kettle, heating to 60-70 ℃ under stirring, dropwise adding a mixture of dodecene, a Speier catalyst and an amine compound, controlling the dropwise adding time to be 15-30 min, and reacting for 4-8 h at 90-130 ℃ after dropwise adding; and carrying out vacuum reduced pressure distillation on the obtained product, and removing low boiling point to obtain the long-chain alkyl modified hydrogen-containing silicone oil lubricating oil.
Further, the hydrogen content of the hydrogen-containing silicone oil is 0.4-1.6 wt%, and preferably 0.5 wt%.
Still further, the viscosity of the hydrogen-containing silicone oil is 90-170 mpa.s, and preferably 135 mpa.s.
Furthermore, the molar ratio of the hydrogen-containing silicone oil to the dodecene is 1: (1-1.3), preferably 1: 1.2.
Preferably, the vacuum degree of the reduced pressure distillation is-0.0998 to-0.1 MPa, and is preferably-0.1 MPa.
Preferably, the reduced pressure distillation temperature is 20-180 ℃, and preferably 150 ℃.
The Speier catalyst is a mixture of chloroplatinic acid and isopropanol, the mass concentration of Pt is 1%, and the input amount is 1-10 ppm, preferably 5ppm of the mass of the raw materials.
The amine compound is N, N-dimethylaniline, the purity is analytical purity, and the using amount is 0.7-1.9 mg/g, preferably 1.6 mg/g.
The long-chain alkyl modified hydrogen-containing silicone oil lubricating oil is characterized by nuclear magnetic resonance and infrared spectroscopy, and the result shows that the long-chain alkyl modified hydrogen-containing silicone oil lubricating oil prepared by the preparation method of the long-chain alkyl modified hydrogen-containing silicone oil lubricating oil has a single structure and high purity.
Compared with the prior art, the invention has the beneficial effects that: the raw material cost is low; an amine compound is used as a Speier catalyst auxiliary agent, so that the reaction efficiency is improved, the olefin isomerization side reaction is greatly reduced, no gel is generated, and the quality of a finished product is better; strong acid and strong alkali are not needed, post-treatment such as water washing, neutralization and the like is not needed, and reaction steps and time are saved.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of modified silicone oil prepared by the method for preparing long-chain alkyl modified hydrogen-containing silicone oil lubricating oil of example 1.
FIG. 2 is an infrared spectrum of modified silicone oil prepared by the method for preparing long-chain alkyl-modified hydrogen-containing silicone oil lubricating oil of example 1.
Detailed Description
The invention is further described below with reference to the accompanying drawings.
Example 1
A preparation method of long-chain alkyl modified hydrogen-containing silicone oil lubricating oil comprises the following steps: 50g of hydrogen-containing silicone oil is poured into a 500ml three-hole flask at room temperature, stirred, heated to 70 ℃, and then 50.4g of dodecene, 10ppm of Speier catalyst and 1.9mg/g N of N-dimethylaniline are dropwise added for 30min, and then the mixture is maintained at 130 ℃ for 8 h. And finally cooling to room temperature, vacuumizing to remove low boiling, wherein the vacuum degree is-0.0998 MPa, the highest temperature is 150 ℃, and the time is 1.5 hours, so that a qualified product is obtained.
The product index is as follows:
viscosity: 500 to 1200mpa.s
Refractive index: 1.4300-1.4370
Volatile components: 0.1 to 1 percent.
Example 2
A preparation method of long-chain alkyl modified hydrogen-containing silicone oil lubricating oil comprises the following steps: 50g of hydrogen-containing silicone oil is poured into a 50ml three-hole flask at room temperature, stirred, heated to 65 ℃, 46.2g of dodecene, 5ppm of Speier catalyst and 1.6mg/g N of N-dimethylaniline are dropwise added for 20min, and then the mixture is maintained at 110 ℃ for 6 h. And finally cooling to room temperature, vacuumizing to remove low boiling, wherein the vacuum degree is-0.099 MPa, the highest temperature is 150 ℃, and the time is 1.5h, so that a qualified product is obtained.
The product index is as follows:
viscosity: 500 to 1200mpa.s
Refractive index: 1.4300-1.4370
Volatile components: 0.1 to 1 percent.
Example 3
A preparation method of long-chain alkyl modified hydrogen-containing silicone oil lubricating oil comprises the following steps: a preparation method of long-chain alkyl modified hydrogen-containing silicone oil lubricating oil comprises the following steps: 50g of hydrogen-containing silicone oil is poured into a 50ml three-hole flask at room temperature, stirred, heated to 60 ℃, and then 42g of dodecene, 1ppm of Speier catalyst and 0.7mg/g N g of N-dimethylaniline are dropwise added for 15min, and then the mixture is maintained at 90 ℃ for 4 h. And finally cooling to room temperature, vacuumizing to remove low boiling, wherein the vacuum degree is-0.1 MPa, the highest temperature is 150 ℃, and the time is 1.5 hours, so that a qualified product is obtained.
Comparative example 1
50g of hydrogen-containing silicone oil is poured into a 500ml three-hole flask at room temperature, stirred, heated to 70 ℃, and then 50.4g of dodecene and 0.1339g of Speier catalyst are dropwise added for 15min and then maintained at 100 ℃ for 6 h. And finally cooling to room temperature, vacuumizing to remove low boiling, wherein the vacuum degree is-0.099 MPa, the highest temperature is 150 ℃, and the time is 1.5h, so that a qualified product is obtained.
The product index is as follows:
viscosity: 500 to 1200mpa.s
Refractive index: 1.4300-1.4370
Volatile components: 0.1 to 1 percent.
Comparative example 2
Pouring 70g of hydrogen-containing silicone oil into a 500ml three-hole flask at room temperature, stirring, heating to 80 ℃, dropwise adding 70.6g of dodecene and 0.3g of Speier catalyst for 18min, and maintaining at 110 ℃ for 6 h. And finally cooling to room temperature, vacuumizing to remove low boiling, wherein the vacuum degree is-0.099 MPa, the highest temperature is 150 ℃, and the time is 1.5h, so that a qualified product is obtained.
The product index is as follows:
viscosity: 500 to 1200mpa.s
Refractive index: 1.4300-1.4370
Volatile components: 0.1 to 1 percent.
The embodiments described in this specification are merely illustrative of implementations of the inventive concepts, which are intended for purposes of illustration only. The scope of the present invention should not be construed as being limited to the particular forms set forth in the examples, but rather as being defined by the claims and the equivalents thereof which can occur to those skilled in the art upon consideration of the present inventive concept.
Claims (4)
1. The preparation method of the long-chain alkyl modified hydrogen-containing silicone oil lubricating oil is characterized by comprising the following steps: adding hydrogen-containing silicone oil into a reaction kettle, heating to 60-70 ℃ under stirring, dropwise adding a mixture of dodecene, a Speier catalyst and an amine compound, controlling the dropwise adding time to be 15-30 min, and reacting for 4-8 h at 90-130 ℃ after dropwise adding; and carrying out vacuum reduced pressure distillation on the obtained product, and removing low boiling point to obtain the long-chain alkyl modified hydrogen-containing silicone oil lubricating oil.
2. The preparation method of the long-chain alkyl modified hydrogen-containing silicone oil lubricating oil according to claim 1, wherein the hydrogen content of the hydrogen-containing silicone oil is 0.4-1.6 wt%; the viscosity of the hydrogen-containing silicone oil is 90-170 mpa.s; the mol ratio of hydrogen-containing silicone oil to dodecene is 1: (1-1.3); the vacuum degree of the reduced pressure distillation is-0.0998 to-0.1 Mpa; the reduced pressure distillation temperature is 20-180 ℃; the Speier catalyst is a mixture of chloroplatinic acid and isopropanol, the mass concentration of Pt is 1%, and the input amount is 1-10 ppm of the mass of the raw materials; the amine compound is N, N-dimethylaniline, the purity is analytical purity, and the dosage is 0.7-1.9 mg/g.
3. The method for preparing a long-chain alkyl modified hydrogen-containing silicone oil lubricant oil according to claim 2, wherein the amount of N, N-dimethylaniline added is 1.6 mg/g.
4. The method for preparing long-chain alkyl modified hydrogen-containing silicone oil lubricating oil according to claim 2, wherein the hydrogen content of the hydrogen-containing silicone oil is 0.5 wt%, the viscosity of the hydrogen-containing silicone oil is 135mpa.s, the molar ratio of the hydrogen-containing silicone oil to dodecene is 1:1.2, the vacuum degree of reduced pressure distillation is-0.1 Mpa, the temperature of reduced pressure distillation is 150 ℃, and the input amount of Speier catalyst is 5ppm of the mass of the raw materials.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111548499A (en) * | 2020-04-08 | 2020-08-18 | 浙江工业大学 | Preparation method of p-methylstyrene/1-octene co-modified hydrogen-containing silicone oil release agent |
| CN113816983A (en) * | 2021-11-04 | 2021-12-21 | 枣阳市华威硅氟材料有限公司 | Method for catalyzing hydrosilylation reaction by using p-cymene ruthenium dichloride dimer |
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| US6590117B1 (en) * | 2001-11-15 | 2003-07-08 | Crompton Corporation | Promoted hydrosilation reactions |
| CN101402735A (en) * | 2008-11-11 | 2009-04-08 | 宁波润禾化学工业有限公司 | Process for producing long-chain alkyl-silicone oil |
| CN103936782A (en) * | 2014-04-03 | 2014-07-23 | 山东硅科新材料有限公司 | Method for preparing long-chain alkyl siloxane by virtue of catalyzed hydrosilylation |
| CN107365416A (en) * | 2017-08-30 | 2017-11-21 | 山东大学 | A kind of method for preparing modified side chain polysiloxanes |
-
2020
- 2020-11-05 CN CN202011221728.9A patent/CN112457497A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6590117B1 (en) * | 2001-11-15 | 2003-07-08 | Crompton Corporation | Promoted hydrosilation reactions |
| CN101402735A (en) * | 2008-11-11 | 2009-04-08 | 宁波润禾化学工业有限公司 | Process for producing long-chain alkyl-silicone oil |
| CN103936782A (en) * | 2014-04-03 | 2014-07-23 | 山东硅科新材料有限公司 | Method for preparing long-chain alkyl siloxane by virtue of catalyzed hydrosilylation |
| CN107365416A (en) * | 2017-08-30 | 2017-11-21 | 山东大学 | A kind of method for preparing modified side chain polysiloxanes |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111548499A (en) * | 2020-04-08 | 2020-08-18 | 浙江工业大学 | Preparation method of p-methylstyrene/1-octene co-modified hydrogen-containing silicone oil release agent |
| CN113816983A (en) * | 2021-11-04 | 2021-12-21 | 枣阳市华威硅氟材料有限公司 | Method for catalyzing hydrosilylation reaction by using p-cymene ruthenium dichloride dimer |
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