CN113072577A - Method for preparing long-chain fluoroalkyl siloxane - Google Patents
Method for preparing long-chain fluoroalkyl siloxane Download PDFInfo
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- CN113072577A CN113072577A CN202110284965.8A CN202110284965A CN113072577A CN 113072577 A CN113072577 A CN 113072577A CN 202110284965 A CN202110284965 A CN 202110284965A CN 113072577 A CN113072577 A CN 113072577A
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- chloroplatinic acid
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- hexafluoroisopropanol
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- -1 fluoroalkyl siloxane Chemical class 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 32
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 8
- 229910000077 silane Inorganic materials 0.000 claims abstract description 8
- 150000004687 hexahydrates Chemical class 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 3
- WFLOTYSKFUPZQB-UHFFFAOYSA-N 1,2-difluoroethene Chemical compound FC=CF WFLOTYSKFUPZQB-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000035484 reaction time Effects 0.000 claims description 4
- 229920002978 Vinylon Polymers 0.000 claims 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006459 hydrosilylation reaction Methods 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 5
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 3
- FYQFWFHDPNXORA-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C FYQFWFHDPNXORA-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- MHQSODYIEVVICX-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-tetracosafluorododec-1-ene Chemical group FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F MHQSODYIEVVICX-UHFFFAOYSA-N 0.000 description 1
- NKAMGQZDVMQEJL-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C NKAMGQZDVMQEJL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- SLIOYUPLNYLSSR-UHFFFAOYSA-J tetrachloroplatinum;hydrate;dihydrochloride Chemical compound O.Cl.Cl.Cl[Pt](Cl)(Cl)Cl SLIOYUPLNYLSSR-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for preparing long-chain fluoroalkyl siloxane, which takes long-chain fluoro fluoroethylene and alkoxy silane as raw materials to prepare the long-chain fluoroalkyl siloxane through hydrosilylation, and is characterized in that hexafluoroisopropanol solution of chloroplatinic acid is taken as a catalyst; the platinum catalyst is used in an amount of 10 parts of the amount of the alkoxysilane substance‑5～10‑4. Under the protection of nitrogen, adding hexafluoroisopropanol into chloroplatinic acid hexahydrate to completely dissolve the chloroplatinic acid to prepare a chloroplatinic acid/hexafluoroisopropanol solution with the concentration of 1-10 mM; sequentially adding alkoxy silane, long-chain fluoro vinyl fluoride and a prepared chloroplatinic acid/hexafluoroisopropanol solution into a reactor, and reacting for 30-60 min at 40-80 ℃; and distilling the reaction liquid under reduced pressure to obtain the target product long-chain fluoroalkyl siloxane. The method has the advantages of simple process, mild reaction conditions, and high product yield and purity.
Description
Technical Field
The invention relates to a preparation method of long-chain fluoroalkyl siloxane, belonging to the field of fluorosilicone chemistry.
Background
Due to the super-strong hydrophobic and oleophobic properties, durability and chemical stability of the fluoroalkyl siloxane, the fluoroalkyl siloxane has important application in special coating materials. The long-chain (generally more than 5 carbons) fluoroalkyl siloxane has the characteristics of high fluorine content, flexible structure and the like, so that compared with short-chain fluoroalkyl siloxane, the long-chain fluoroalkyl siloxane has more excellent unique performances of super hydrophobicity, self-cleaning, self-repairing and the like, and has extremely high application value and commercial value on high-end equipment and devices.
By noble goldBelongs to the field of catalytic hydrosilylation reaction to prepare siloxane, is one of the most important means for functionalizing organic silicon, and especially has high application value in the industrial production of fluoroalkyl siloxane and derivatives thereof. In 1957, Speier discovered chloroplatinic acid hydrate (H)2PtCl6*H2O) is a very effective homogeneous hydrosilylation catalyst (hereinafter designated as Speier catalyst). The discovery of the Speier catalyst greatly improves the yield and the reaction rate of the hydrosilylation reaction, and is also the catalyst which is most widely applied in industry at present. However, the Speier catalyst still has the defects of large catalyst dosage, low selectivity on target products and no catalytic activity for some reactions. In particular, for hydrosilylation of fluoroalkyl siloxanes, especially long-chain fluoroalkyl siloxanes, long-chain fluorine-containing olefins themselves are less reactive than small-molecule olefins, and further, due to poor compatibility of fluorocarbons with catalysts and solvents, hydrosilylation requires longer reaction time, higher reaction temperature and reaction pressure, which increases the formation of silane self-coupling byproducts on the one hand, and fluorine-containing olefins are easily isomerized at high temperatures on the other hand, thereby reducing the yield and purity of the main product (y. furukawa, Journal of Polymer Science Part a: Polymer Chemistry).
Patent document CN 104497033 a adopts a method of polyvinyl siloxane supported chloroplatinic acid catalyst to improve the activity of the catalyst, but the preparation process of the supported catalyst in the method is complex and is not beneficial to industrial application.
Patent document CN103936782A discloses adding a co-catalyst such as pyruvic acid to a chloroplatinic acid/isopropanol catalyst system to improve the yield of hydrosilylation reaction products, but this method is limited to the preparation of long chain alkyl hydrocarbon siloxanes, and has little catalytic effect on long chain fluorocarbon siloxanes.
Disclosure of Invention
The invention aims to provide a method for preparing long-chain fluoroalkyl siloxane, which has the advantages of simple process, mild reaction conditions and high product yield and purity.
In order to achieve the above-mentioned objects of the invention,the invention adopts the technical scheme that the method for preparing the long-chain fluoroalkyl siloxane adopts long-chain fluoro alkyl ethylene and alkoxy silane as raw materials and prepares the long-chain fluoroalkyl siloxane through hydrosilylation reaction, and is characterized in that hexafluoroisopropanol solution of chloroplatinic acid is used as a catalyst. The amount of the platinum catalyst (calculated by chloroplatinic acid) is 10 of the amount of the alkoxy silane substance-5～10-4Preferably 3X 10-5～5×10-5. The concentration of the platinum catalyst is too low, which affects the catalytic efficiency, and the concentration of the platinum catalyst is too high, which does not obviously improve the yield.
In further detail, a method of preparing a long chain fluoroalkyl siloxane, comprising the steps of:
(1) under the protection of nitrogen, adding hexafluoroisopropanol into chloroplatinic acid hexahydrate to completely dissolve the chloroplatinic acid to prepare a chloroplatinic acid/hexafluoroisopropanol solution with the concentration of 1-10 mM. The concentration of the chloroplatinic acid/hexafluoroisopropanol solution is preferably 2-5 mM.
(2) And (3) sequentially adding alkoxy silane, long-chain fluorocarbon vinyl and prepared chloroplatinic acid/hexafluoroisopropanol solution into the reactor, and reacting for 30-60 min at 40-80 ℃. The preferred molar ratio of the alkoxy silane to the long-chain fluoro alkyl ethylene is 1: 0.9-1.05. The reaction temperature is preferably 40-55 ℃, and the reaction time is preferably 30-40 min.
(3) And distilling the reaction liquid under reduced pressure to obtain the target product long-chain fluoroalkyl siloxane.
The long chain fluorocarbon vinyl has the following formula F (CF)2)nCHCH2And n is 3 to 10.
Said alkoxysilane having the formula HSi (OC)nH2n+1)3And n is 1 to 2.
Due to the adoption of the technical scheme, the invention has the following beneficial effects:
1. the catalyst is prepared from hexafluoroisopropanol, and the method is simple and does not need a special preparation process. Hexafluoroisopropanol is a conventional reagent and is commercially available.
2. The coordination of hexafluoroisopropanol and platinum greatly increases the solubility and catalytic efficiency of platinum in a fluorine phase system, greatly shortens the hydrosilylation reaction time, and improves the reaction efficiency.
3. The reaction condition is mild, the reaction temperature is low, the reaction is carried out under normal pressure, the process operation is simple, convenient and safe, and the industrial production is easy to realize.
4. The product yield is high, and the yield is over 95 percent and can reach 97 percent at most.
Detailed Description
The present invention is further described in detail below with reference to specific examples, which are intended to be illustrative only and are not intended to limit the scope of the present invention. It will be appreciated by those skilled in the art that the present invention encompasses all alternatives, modifications and equivalents as may be included within the scope of the claims.
In the embodiment of the invention, the content of each substance is quantitatively analyzed by using a gas chromatograph, and the content is quantitatively determined by using an Agilent 7820 type gas chromatograph and an FID (field intensity distribution Detector) and an area normalization method.
Example 1
Under the protection of nitrogen, a certain amount of hexafluoroisopropanol is added into chloroplatinic acid hexahydrate to completely dissolve the chloroplatinic acid, and a chloroplatinic acid/hexafluoroisopropanol solution with the concentration of 5mM is prepared.
Adding 52.96g of trimethoxy silane and 150g of perfluorohexylethylene into a 500mL round-bottom flask in sequence, adding 4.33mL of chloroplatinic acid/hexafluoroisopropanol under stirring, heating in an oil bath to 40 ℃ after the addition is finished, reacting for 30min, detecting that the reaction raw materials are completely consumed by GC, stopping heating, and distilling the crude product under reduced pressure to obtain 200.82g of a product with the purity of 98.5 percent and the yield of 97.46 percent.
Example 2
Under the protection of nitrogen, a certain amount of hexafluoroisopropanol is added into chloroplatinic acid hexahydrate to completely dissolve the chloroplatinic acid, and a chloroplatinic acid/hexafluoroisopropanol solution with the concentration of 5mM is prepared.
Adding 64.08g of triethoxysilane and 135g of perfluorooctylethylene into a 500mL round-bottom flask in sequence, adding 3.90mL of chloroplatinic acid/hexafluoroisopropanol under stirring, heating the flask to 50 ℃ in an oil bath after the addition is finished, reacting for 50min, detecting that the reaction raw materials are completely consumed by GC, stopping heating, and distilling the crude product under reduced pressure to obtain 194.12g of a product with the purity of 98.8% and the yield of 96.34%.
Example 3
Under the protection of nitrogen, a certain amount of hexafluoroisopropanol is added into chloroplatinic acid hexahydrate to completely dissolve the chloroplatinic acid, and a chloroplatinic acid/hexafluoroisopropanol solution with the concentration of 5mM is prepared.
Adding 76.29g of trimethoxy silane and 160g of perfluorodecyl ethylene in turn into a 500mL round-bottom flask, adding 4.20mL of chloroplatinic acid/hexafluoroisopropanol under stirring, heating the flask to 55 ℃ in an oil bath after the addition is finished, reacting for 60min, detecting that the reaction raw materials are completely consumed by GC, stopping heating, and distilling the crude product under reduced pressure to obtain 228.91g of a product with the purity of 98 percent and the yield of 95.08 percent.
Comparative example 1
And (2) sequentially adding 35.31g of triethoxysilane and 100g of perfluorohexylethylene into a 250mL pressure reaction kettle, adding 5.78mL of chloroplatinic acid/isopropanol with the concentration of 5mM while stirring, heating the mixture to 110 ℃ in an oil bath after the addition is finished, reacting for 5 hours under the reaction pressure of 0.6MPa, stopping heating, cooling the crude product, and performing reduced pressure distillation on the crude product to obtain 83.28g of a product with the purity of 77.6 percent and the yield of 47.76 percent.
Claims (10)
1. A process for preparing long-chain fluoroalkyl siloxane features that the hexafluoroisopropanol solution of chloroplatinic acid is used as catalyst.
2. The method as set forth in claim 1, wherein the amount of the platinum catalyst is 10% of the amount of the alkoxysilane substance-5～10-4。
3. The method as set forth in claim 1, wherein the platinum catalyst is used in an amount of 3 x 10 based on the amount of the alkoxysilane substance-5～5×10-5。
4. The method of claim 1, wherein said long chain fluorocarbon vinyl group has the following molecular weightFormula F (CF)2)nCHCH2And n is 3 to 10.
5. The process as claimed in claim 1, wherein the alkoxysilane has the formula HSi (OC)nH2n+1)3And n is 1 to 2.
6. The method of claim 1, including the steps of:
(1) under the protection of nitrogen, adding hexafluoroisopropanol into chloroplatinic acid hexahydrate to completely dissolve the chloroplatinic acid to prepare a chloroplatinic acid/hexafluoroisopropanol solution with the concentration of 1-10 mM;
(2) sequentially adding alkoxy silane, long-chain fluoro vinyl fluoride and a prepared chloroplatinic acid/hexafluoroisopropanol solution into a reactor, and reacting for 30-60 min at 40-80 ℃;
(3) and distilling the reaction liquid under reduced pressure to obtain the target product long-chain fluoroalkyl siloxane.
7. The method according to claim 6, wherein the concentration of the chloroplatinic acid/hexafluoroisopropanol solution is 2 to 5 mM.
8. The method as set forth in claim 6, wherein the reaction temperature in the step (2) is 40 to 55 ℃.
9. The method as set forth in claim 6, wherein the reaction time in the step (2) is 30 to 40 min.
10. The method as set forth in claim 6, wherein the molar ratio of alkoxysilane to long-chain fluorocarbon vinylon is 1: 0.9-1.05.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110284965.8A CN113072577A (en) | 2021-03-12 | 2021-03-12 | Method for preparing long-chain fluoroalkyl siloxane |
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| CN202110284965.8A CN113072577A (en) | 2021-03-12 | 2021-03-12 | Method for preparing long-chain fluoroalkyl siloxane |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114057973A (en) * | 2021-12-07 | 2022-02-18 | 广州予能新材料科技有限公司 | Organic silicon modified polyurethane material and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106866972A (en) * | 2017-02-21 | 2017-06-20 | 陕西科技大学 | Touch the preparation method and application of the panel glass antifouling anti-fingerprint resin of fluorine silicon |
-
2021
- 2021-03-12 CN CN202110284965.8A patent/CN113072577A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106866972A (en) * | 2017-02-21 | 2017-06-20 | 陕西科技大学 | Touch the preparation method and application of the panel glass antifouling anti-fingerprint resin of fluorine silicon |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114057973A (en) * | 2021-12-07 | 2022-02-18 | 广州予能新材料科技有限公司 | Organic silicon modified polyurethane material and preparation method thereof |
| CN114057973B (en) * | 2021-12-07 | 2023-04-28 | 广州予能新材料科技有限公司 | Organosilicon modified polyurethane material and preparation method thereof |
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