CN112250867A - Preparation method of methyl silicone oil - Google Patents
Preparation method of methyl silicone oil Download PDFInfo
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- CN112250867A CN112250867A CN202011171144.5A CN202011171144A CN112250867A CN 112250867 A CN112250867 A CN 112250867A CN 202011171144 A CN202011171144 A CN 202011171144A CN 112250867 A CN112250867 A CN 112250867A
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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
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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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
- C08G77/06—Preparatory processes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention relates to a preparation method of methyl silicone oil, which comprises the following steps: preparing modified diatomite; preparing a mixture containing an organic ligand, zirconium tetrachloride and a heteropoly acid; and (3) synthesizing the dimethyl silicone oil. According to the invention, the heteropoly acid, the metal-organic framework and the diatomite are combined to prepare the composite catalyst, so that multi-scale dispersion and solid support of molecular level, atomic level and the like are realized, the characteristics of the heteropoly acid, the diatomite and the organic-metal framework that the catalytic effect is synergistically enhanced can be fully exerted, the catalytic effect in dimethyl silane synthesis can be improved, the generation of byproducts is inhibited, and dimethyl silane with high purity and high yield is obtained; by adopting the composite catalyst, the catalyst can be recovered, the using amount of the catalyst can be obviously reduced, neutralization is not needed, and the amount of waste water is small.
Description
Technical Field
The invention relates to the technical field of synthesis of methyl silicone oil, in particular to a preparation method of methyl silicone oil.
Background
The methyl silicone oil is colorless and odorless transparent liquid, has the advantages of no toxicity, no odor, good chemical stability, high temperature resistance, small demoulding force and the like, and is widely used in the fields of plastics, rubber and the like.
It is generally employed industrially to prepare low molar mass dimethylcyclosiloxanes by equilibration with trimethylsiloxy-terminated low molar mass dimethylpolysiloxanes. The choice of catalyst is very important during its synthesis. Catalysts for methylsilicone oil synthesis fall into two broad categories: an acidic catalyst and a basic catalyst. Typical acidic catalysts are concentrated sulfuric acid, trifluoromethanesulfonic acid, solid acid catalysts and the like, and basic catalysts are potassium hydroxide. Although it has high catalytic activity, the dosage is large, the product needs neutralization and water washing, the product yield is low, the catalyst has high corrosion to equipment, and the production cost is increased.
Disclosure of Invention
In view of the above, there is a need to provide a method for preparing methyl silicone oil, which is used to solve the technical problem of product yield in the existing method for preparing methyl silicone oil in the prior art.
The invention provides a preparation method of methyl silicone oil, which comprises the following steps:
preparing modified diatomite;
preparation of a mixture containing organic ligands, zirconium tetrachloride and heteropolyacids: adding an organic ligand and zirconium tetrachloride into an organic solvent, stirring for 0.5-1 h, then adding concentrated hydrochloric acid, stirring for 2-4 h, then adding heteropoly acid, and stirring for 1-2 h to obtain a mixture containing the organic ligand, the zirconium tetrachloride and the heteropoly acid;
preparing a composite catalyst: mixing modified diatomite with the mixture containing the organic ligand, zirconium tetrachloride and heteropoly acid, stirring for 0.5-1 h, and carrying out hydrothermal reaction to obtain a composite catalyst;
and (3) synthesizing dimethyl silicone oil: mixing low-molar-mass dimethyl cyclosiloxane, hexamethyldisiloxane and the composite catalyst, stirring and reacting for 3-5 hours at 70-90 ℃, filtering and recovering the composite catalyst after the reaction is finished, and removing low-boiling-point substances in the filtrate for 3-5 hours at 120-130 ℃ and under the negative pressure of 0.06-0.09 MPa to obtain the simethicone.
Further, the preparation method of the modified diatomite comprises the following specific steps:
and sequentially calcining the diatomite, treating with dilute sulfuric acid and treating with a cetyl trimethyl ammonium bromide solution to obtain the modified diatomite.
Furthermore, the calcining temperature is 550-650 ℃, and the calcining time is 1-3 h;
the concentration of the dilute sulfuric acid is 1-3 mol/L, the dosage ratio of the diatomite to the dilute sulfuric acid is 1g (5-10 ml), the treatment temperature of the dilute sulfuric acid is 40-60 ℃, and the treatment time is 3-5 h;
the mass fraction of the cetyl trimethyl ammonium bromide solution is 3-5%, the mass ratio of the diatomite to the cetyl trimethyl ammonium bromide solution is 1 (4-6), the treatment temperature of the cetyl trimethyl ammonium bromide solution is 70-80 ℃, and the treatment time is 1-3 hours.
Further, the organic ligand is one or more of terephthalic acid, trimesic acid and biphenyldicarboxylic acid; the organic solvent is ethanol or N, N-dimethylformamide; the heteropoly acid is one or more of phosphotungstic acid, silicotungstic acid, phosphomolybdic acid and silicomolybdic acid.
Furthermore, the mass ratio of the organic ligand, the zirconium tetrachloride, the concentrated hydrochloric acid and the heteropoly acid is 1 (0.6-1.5) to 1.6-2 to 0.3-0.5, and the dosage ratio of the organic ligand to the organic solvent is 1g (10-20) ml.
Furthermore, the dosage ratio of the modified diatomite to the mixture containing the organic ligand, zirconium tetrachloride and heteropoly acid is 1g (5-10) ml.
Furthermore, the temperature of the hydrothermal reaction is 150-180 ℃, and the time of the hydrothermal reaction is 6-8 h.
Further, after the hydrothermal reaction is finished, drying and activating the hydrothermal product at 120-150 ℃ for 12-24 h to finally obtain the composite catalyst.
Further, the low molar mass dimethylcyclosiloxane is one or more of hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane.
Furthermore, the mass ratio of the low-molar-mass dimethyl cyclosiloxane, the hexamethyldisiloxane and the composite catalyst is 1 (0.01-0.03) to (0.005-0.01).
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, the heteropoly acid, the metal-organic framework and the diatomite are combined to prepare the composite catalyst, so that multi-scale dispersion and solid support of molecular level, atomic level and the like are realized, the characteristics of the heteropoly acid, the diatomite and the organic-metal framework that the catalytic effect is synergistically enhanced can be fully exerted, the catalytic effect in dimethyl silane synthesis can be improved, the generation of byproducts is inhibited, and dimethyl silane with high purity and high yield is obtained; by adopting the composite catalyst, the catalyst can be recovered, the using amount of the catalyst can be obviously reduced, neutralization is not needed, and the amount of waste water is small.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The invention provides a preparation method of methyl silicone oil, which comprises the following steps:
s1 preparation of modified diatomaceous earth: and sequentially calcining the diatomite, treating with dilute sulfuric acid and treating with a cetyl trimethyl ammonium bromide solution to obtain the modified diatomite. In the process, the calcining temperature is 550-650 ℃, and the calcining time is 1-3 h; the concentration of the dilute sulfuric acid is 1-3 mol/L, the dosage ratio of the diatomite to the dilute sulfuric acid is 1g (5-10 ml), the treatment temperature of the dilute sulfuric acid is 40-60 ℃, and the treatment time is 3-5 h; the mass fraction of the cetyl trimethyl ammonium bromide solution is 3-5%, the mass ratio of the diatomite to the cetyl trimethyl ammonium bromide solution is 1 (4-6), the treatment temperature of the cetyl trimethyl ammonium bromide solution is 70-80 ℃, and the treatment time is 1-3 hours. According to the invention, the diatomite is sequentially subjected to calcination, dilute sulfuric acid treatment and hexadecyl trimethyl ammonium bromide solution treatment, so that the pore structure of the diatomite can be optimized, the surface property of the diatomite can be changed, and the loading capacity of heteropoly acid and organic ligand can be improved. Furthermore, the mesh number of the modified diatomite is 200-300 meshes.
S2 preparation of a mixture containing organic ligands, zirconium tetrachloride and heteropolyacids: adding an organic ligand and zirconium tetrachloride into an organic solvent, stirring for 0.5-1 h, then adding concentrated hydrochloric acid, stirring for 2-4 h, then adding heteropoly acid, and stirring for 1-2 h to obtain a mixture containing the organic ligand, the zirconium tetrachloride and the heteropoly acid. In the process, the organic ligand is one or more of terephthalic acid, trimesic acid and biphenyldicarboxylic acid; the organic solvent is ethanol or N, N-dimethylformamide; the heteropoly acid is one or more of phosphotungstic acid, silicotungstic acid, phosphomolybdic acid and silicomolybdic acid; the mass ratio of the organic ligand to the zirconium tetrachloride to the concentrated hydrochloric acid to the heteropoly acid is 1 (0.6-1.5) to 1.6-2 to 0.3-0.5, and the dosage ratio of the organic ligand to the organic solvent is 1g (10-20) ml.
S3 preparation of the composite catalyst: and mixing the modified diatomite with the mixture containing the organic ligand, zirconium tetrachloride and heteropoly acid, stirring for 0.5-1 h, and carrying out hydrothermal reaction to obtain the composite catalyst. The dosage ratio of the modified diatomite to the mixture containing the organic ligand, zirconium tetrachloride and heteropoly acid is 1g (5-10) ml. The temperature of the hydrothermal reaction is 150-180 ℃, and the time of the hydrothermal reaction is 6-8 h. After the hydrothermal reaction is finished, drying and activating the hydrothermal product at 120-150 ℃ for 12-24 h to finally obtain the composite catalyst.
S4 Synthesis of Dimethicone: mixing low-molar-mass dimethyl cyclosiloxane, hexamethyldisiloxane and the composite catalyst, stirring and reacting for 3-5 hours at 70-90 ℃, filtering and recovering the composite catalyst after the reaction is finished, and removing low-boiling-point substances in the filtrate for 3-5 hours at 120-130 ℃ and under the negative pressure of 0.06-0.09 MPa to obtain the dimethyl silicone oil. In the present embodiment, the low molar mass dimethylcyclosiloxane is one or more of hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane, and octamethylcyclotetrasiloxane is preferable. The mass ratio of the low-molar-mass dimethyl cyclosiloxane to the hexamethyldisiloxane to the composite catalyst is 1 (0.01-0.03) to 0.005-0.01.
In the present invention, the temperature used is room temperature unless otherwise specified.
For avoiding redundancy, in each example and comparative example of the invention, the modified diatomite is prepared by the following steps:
the modified diatomite is calcined at 600 ℃ for 2 hours, then added into 2mol/L dilute sulfuric acid according to the dosage ratio of 1g:10ml, treated at 50 ℃ for 4 hours, dried, added into 5 mass percent hexadecyl trimethyl ammonium bromide solution according to the mass ratio of 1:5, and treated at 75 ℃ for 2 hours to obtain the modified diatomite. The mesh number of the obtained modified diatomite is 200-300 meshes.
Example 1
(1) Adding terephthalic acid and zirconium tetrachloride into N, N-dimethylformamide, stirring for 0.8h, then adding concentrated hydrochloric acid, stirring for 3h, then adding phosphotungstic acid, and stirring for 1.5h to obtain a mixture containing an organic ligand, zirconium tetrachloride and heteropoly acid. Wherein the mass ratio of the terephthalic acid to the zirconium tetrachloride to the concentrated hydrochloric acid to the phosphotungstic acid is 1:1:1.8:0.4, and the dosage ratio of the terephthalic acid to the N, N-dimethylformamide is 1g:15 ml.
(2) And mixing the modified diatomite and the mixture containing the organic ligand, zirconium tetrachloride and heteropoly acid according to the dosage ratio of 1g to 8ml, stirring for 0.8h, carrying out hydrothermal reaction for 7h at 160 ℃, and then drying and activating for 18h at 130 ℃ to obtain the composite catalyst.
(3) Mixing octamethylcyclotetrasiloxane, hexamethyldisiloxane and the composite catalyst according to the mass ratio of 1:0.02:0.008, stirring and reacting for 4 hours at 80 ℃, filtering and recovering the composite catalyst after the reaction is finished, and removing low-boiling-point substances in the filtrate for 3-5 hours at 120-130 ℃ and under the negative pressure of 0.06-0.09 MPa to obtain the simethicone.
Example 2
(1) Adding trimesic acid and zirconium tetrachloride into N, N-dimethylformamide, stirring for 0.5h, then adding concentrated hydrochloric acid, stirring for 2h, then adding phosphomolybdic acid, and stirring for 1h to obtain a mixture containing an organic ligand, zirconium tetrachloride and heteropoly acid. Wherein the mass ratio of the trimesic acid to the zirconium tetrachloride to the concentrated hydrochloric acid to the phosphomolybdic acid is 1:0.6:1.6:0.3, and the dosage ratio of the trimesic acid to the N, N-dimethylformamide is 1g:10 ml.
(2) And mixing the modified diatomite and the mixture containing the organic ligand, zirconium tetrachloride and heteropoly acid according to the dosage ratio of 1g:5ml, stirring for 0.5h, carrying out hydrothermal reaction for 8h at 150 ℃, and then drying and activating for 24h at 120 ℃ to obtain the composite catalyst.
(3) Mixing octamethylcyclotetrasiloxane, hexamethyldisiloxane and the composite catalyst according to the mass ratio of 1:0.01:0.005, stirring and reacting for 5 hours at 70 ℃, filtering and recovering the composite catalyst after the reaction is finished, and removing low-boiling-point substances in the filtrate for 3-5 hours at 120-130 ℃ and under the negative pressure of 0.06-0.09 MPa to obtain the simethicone.
Example 3
(1) Adding the biphenyldicarboxylic acid and the zirconium tetrachloride into N, N-dimethylformamide, stirring for 1h, then adding the concentrated hydrochloric acid, stirring for 4h, then adding the silicotungstic acid, and stirring for 2h to obtain a mixture containing the organic ligand, the zirconium tetrachloride and the heteropoly acid. Wherein the mass ratio of the biphenyldicarboxylic acid to the zirconium tetrachloride to the concentrated hydrochloric acid to the silicotungstic acid is 1:1.5:2:0.5, and the dosage ratio of the biphenyldicarboxylic acid to the N, N-dimethylformamide is 1g:20 ml.
(2) And mixing the modified diatomite and the mixture containing the organic ligand, zirconium tetrachloride and heteropoly acid according to the dosage ratio of 1g to 10ml, stirring for 1h, carrying out hydrothermal reaction for 6h at 180 ℃, and then drying and activating for 24h at 150 ℃ to obtain the composite catalyst.
(3) Mixing octamethylcyclotetrasiloxane, hexamethyldisiloxane and the composite catalyst according to the mass ratio of 1:0.03:0.01, stirring and reacting for 3 hours at 90 ℃, filtering and recovering the composite catalyst after the reaction is finished, and removing low-boiling-point substances in the filtrate for 3-5 hours at 120-130 ℃ and under the negative pressure of 0.06-0.09 MPa to obtain the simethicone.
Comparative example 1
The procedure for the synthesis of dimethylsilicone oil in comparative example 1 is identical to that of example 1, except that the catalyst of comparative example 1 is obtained by the following procedure:
(1) adding terephthalic acid and zirconium tetrachloride into N, N-dimethylformamide, stirring for 0.8h, then adding concentrated hydrochloric acid, stirring for 3h, then adding phosphotungstic acid, and stirring for 1.5h to obtain a mixture containing an organic ligand, zirconium tetrachloride and heteropoly acid. Wherein the mass ratio of the terephthalic acid to the zirconium tetrachloride to the concentrated hydrochloric acid to the phosphotungstic acid is 1:1:1.8:0.4, and the dosage ratio of the terephthalic acid to the N, N-dimethylformamide is 1g:15 ml.
(2) And carrying out hydrothermal reaction on the mixture containing the organic ligand, zirconium tetrachloride and heteropoly acid at 160 ℃ for 7h, and then drying and activating at 130 ℃ for 18h to obtain the composite catalyst.
Comparative example 2
The procedure for the synthesis of dimethylsilicone oil in comparative example 2 is identical to that of example 1, except that the catalyst of comparative example 1 is obtained by the following procedure:
(1) adding concentrated hydrochloric acid into N, N-dimethylformamide, stirring for 3h, then adding phosphotungstic acid, and stirring for 1.5h to obtain a heteropoly acid-containing mixture. Wherein the mass ratio of concentrated hydrochloric acid to phosphotungstic acid is 4.5:1, and the dosage ratio of phosphotungstic acid to N, N-dimethylformamide is 1g:20 ml.
(2) And mixing the modified diatomite and the mixture containing the heteropoly acid according to the dosage ratio of 1g to 8ml, stirring for 0.8h, carrying out hydrothermal reaction for 7h at 160 ℃, and then drying and activating for 18h at 130 ℃ to obtain the composite catalyst.
The dimethylsilicone fluids obtained in examples 1-3 and comparative examples 1-2 were tested and the results are shown in Table 1.
TABLE 1
As can be seen from Table 1, the dimethylsilicone fluids obtained in the embodiments 1-3 of the present invention have high yield, which indicates that the composite catalyst of the present invention is favorable for improving the catalytic effect.
The comparative examples 1 and 2 each had a lower yield than example 1, because the composite catalysts obtained in comparative examples 1 and 2 did not have diatomaceous earth and organic ligands added thereto, respectively, and did not achieve multi-scale dispersion and immobilization on a molecular level, an atomic level, etc., resulting in poor catalytic effects of the catalysts obtained.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, the heteropoly acid, the metal-organic framework and the diatomite are combined to prepare the composite catalyst, so that multi-scale dispersion and solid support of molecular level, atomic level and the like are realized, the characteristics of the heteropoly acid, the diatomite and the organic-metal framework that the catalytic effect is synergistically enhanced can be fully exerted, the catalytic effect in dimethyl silane synthesis can be improved, the generation of byproducts is inhibited, and dimethyl silane with high purity and high yield is obtained; by adopting the composite catalyst, the catalyst can be recovered, the using amount of the catalyst can be obviously reduced, neutralization is not needed, and the amount of waste water is small.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention.
Claims (10)
1. The preparation method of the methyl silicone oil is characterized by comprising the following steps:
preparing modified diatomite;
preparation of a mixture containing organic ligands, zirconium tetrachloride and heteropolyacids: adding an organic ligand and zirconium tetrachloride into an organic solvent, stirring for 0.5-1 h, then adding concentrated hydrochloric acid, stirring for 2-4 h, then adding heteropoly acid, and stirring for 1-2 h to obtain a mixture containing the organic ligand, the zirconium tetrachloride and the heteropoly acid;
preparing a composite catalyst: mixing modified diatomite with the mixture containing the organic ligand, zirconium tetrachloride and heteropoly acid, stirring for 0.5-1 h, and carrying out hydrothermal reaction to obtain a composite catalyst;
and (3) synthesizing dimethyl silicone oil: mixing low-molar-mass dimethyl cyclosiloxane, hexamethyldisiloxane and the composite catalyst, stirring and reacting for 3-5 hours at 70-90 ℃, filtering and recovering the composite catalyst after the reaction is finished, and removing low-boiling-point substances in the filtrate for 3-5 hours at 120-130 ℃ and under the negative pressure of 0.06-0.09 MPa to obtain the simethicone.
2. The method for preparing methyl silicone oil according to claim 1, wherein the step of preparing modified diatomite comprises the following steps:
and sequentially calcining the diatomite, treating with dilute sulfuric acid and treating with a cetyl trimethyl ammonium bromide solution to obtain the modified diatomite.
3. The method for preparing the methyl silicone oil according to claim 2, wherein the calcination temperature is 550-650 ℃, and the calcination time is 1-3 h;
the concentration of the dilute sulfuric acid is 1-3 mol/L, the dosage ratio of the diatomite to the dilute sulfuric acid is 1g (5-10 ml), the treatment temperature of the dilute sulfuric acid is 40-60 ℃, and the treatment time is 3-5 h;
the mass fraction of the cetyl trimethyl ammonium bromide solution is 3-5%, the mass ratio of the diatomite to the cetyl trimethyl ammonium bromide solution is 1 (4-6), the treatment temperature of the cetyl trimethyl ammonium bromide solution is 70-80 ℃, and the treatment time is 1-3 hours.
4. The method for preparing the methyl silicone oil according to claim 1, wherein the organic ligand is one or more of terephthalic acid, trimesic acid and biphenyl dicarboxylic acid; the organic solvent is ethanol or N, N-dimethylformamide; the heteropoly acid is one or more of phosphotungstic acid, silicotungstic acid, phosphomolybdic acid and silicomolybdic acid.
5. The method for preparing methyl silicone oil according to claim 1, wherein the mass ratio of the organic ligand to the zirconium tetrachloride to the concentrated hydrochloric acid to the heteropoly acid is 1 (0.6-1.5) to (1.6-2) to (0.3-0.5), and the amount ratio of the organic ligand to the organic solvent is 1g (10-20) ml.
6. The preparation method of the methyl silicone oil according to claim 1, wherein the dosage ratio of the modified diatomite to the mixture containing the organic ligand, the zirconium tetrachloride and the heteropoly acid is 1g (5-10) ml.
7. The method for preparing methyl silicone oil according to claim 1, wherein the temperature of the hydrothermal reaction is 150 to 180 ℃, and the time of the hydrothermal reaction is 6 to 8 hours.
8. The preparation method of the methyl silicone oil according to claim 1, characterized in that after the hydrothermal reaction is finished, the hydrothermal product is dried and activated at 120-150 ℃ for 12-24 hours to finally obtain the composite catalyst.
9. The method for preparing methyl silicone oil according to claim 1, wherein the low molar mass dimethyl cyclosiloxane is one or more of hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane.
10. The method for preparing methyl silicone oil according to claim 1, wherein the mass ratio of the low molar mass dimethyl cyclosiloxane, hexamethyldisiloxane and the composite catalyst is 1 (0.01-0.03): (0.005-0.01).
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