CN112920216A - Preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide - Google Patents
Preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide Download PDFInfo
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- CN112920216A CN112920216A CN202110142434.5A CN202110142434A CN112920216A CN 112920216 A CN112920216 A CN 112920216A CN 202110142434 A CN202110142434 A CN 202110142434A CN 112920216 A CN112920216 A CN 112920216A
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- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 79
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 48
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 claims abstract description 37
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 31
- LTJSXGVQCAVSJW-UHFFFAOYSA-N [K+].[K+].[S-][S-] Chemical compound [K+].[K+].[S-][S-] LTJSXGVQCAVSJW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 24
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 230000035484 reaction time Effects 0.000 claims description 8
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 8
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 8
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 4
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 claims description 4
- 230000008901 benefit Effects 0.000 abstract description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 5
- 239000007789 gas Substances 0.000 abstract description 5
- 229910000037 hydrogen sulfide Inorganic materials 0.000 abstract description 5
- 239000006087 Silane Coupling Agent Substances 0.000 abstract description 3
- PKDCQJMRWCHQOH-UHFFFAOYSA-N triethoxysilicon Chemical compound CCO[Si](OCC)OCC PKDCQJMRWCHQOH-UHFFFAOYSA-N 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000002351 wastewater Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 239000002699 waste material Substances 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
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
A preparation method of bis- [3- (triethoxysilicon) -propyl ] -disulfide relates to the technical field of synthesis of silane coupling agents, in particular to a preparation method of bis- [3- (triethoxysilicon) -propyl ] -disulfide. The method comprises the following steps: step 1, reacting potassium hydroxide with water to prepare a potassium hydroxide solution; step 2, adding potassium carbonate and sulfur powder into the potassium hydroxide solution, and reacting to prepare a potassium disulfide solution; step 3, adding a phase transfer catalyst into a potassium disulfide solution, then dropwise adding 3-chloropropyltriethoxysilane, and reacting to obtain bis- [3- (triethoxysilyl) -propyl ] -disulfide; the molar ratio of the potassium hydroxide to the potassium carbonate to the sulfur powder to the 3-chloropropyltriethoxysilane is (1.2-1.5) to (0.3-0.6) to (1.2-1.8) to 1. The method has the advantages of avoiding the generation of hydrogen sulfide gas, being simple in post-treatment, being green and environment-friendly and improving the economic benefit.
Description
Technical Field
The invention relates to the technical field of synthesis of silane coupling agents, in particular to a preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide.
Background
Bis- [3- (triethoxysilyl) -propyl ] -disulfide is a commonly used silane coupling agent and is widely used in various rubber industries. At present, the preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide generally comprises the steps of reacting sodium hydrosulfide, sodium carbonate and sulfur powder to prepare sodium disulfide, and then reacting the sodium disulfide with 3-chloropropyltriethoxysilane under the action of a phase transfer catalyst to prepare the bis- [3- (triethoxysilyl) -propyl ] -disulfide. Absorption by a falling film absorber is required, increasing equipment cost and floor space. Meanwhile, the generated wastewater is mainly sodium salt wastewater containing sodium chloride and sodium carbonate, so that the post-treatment difficulty is increased, and the production cost is increased.
Disclosure of Invention
The invention aims to provide a preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide, which aims to avoid generating hydrogen sulfide gas, has simple post-treatment, is green and environment-friendly and improves economic benefit.
The invention provides a preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide, which is characterized by comprising the following steps:
step 1, reacting potassium hydroxide with water to prepare a potassium hydroxide solution;
step 2, adding potassium carbonate and sulfur powder into the potassium hydroxide solution, and reacting to prepare a potassium disulfide solution;
step 3, adding a phase transfer catalyst into a potassium disulfide solution, then dropwise adding 3-chloropropyltriethoxysilane, and reacting to obtain bis- [3- (triethoxysilyl) -propyl ] -disulfide;
the molar ratio of the potassium hydroxide to the potassium carbonate to the sulfur powder to the 3-chloropropyltriethoxysilane is (1.2-1.5) to (0.3-0.6) to (1.2-1.8) to 1.
Further, in the step 2, the reaction temperature of the potassium hydroxide solution, the potassium carbonate and the sulfur powder is 60-100 ℃, and the reaction time is 1-3 hours.
Further, in the step 2, the reaction temperature of potassium carbonate and sulfur powder in the potassium hydroxide solution is 70-80 ℃, and the reaction time is 1.5-2.5 h.
Further, in the step 3, the phase transfer catalyst is any one or more of tetrabutylammonium bromide, tetrabutylammonium chloride, dodecyltrimethylammonium chloride and tetradecyltrimethylammonium chloride.
Further, in the step 3, 3-chloropropyltriethoxysilane is dripped into the potassium disulfide solution, the dripping temperature is 60-90 ℃, and the dripping time is 1-3 hours.
Further, in the step 3, 3-chloropropyltriethoxysilane is dripped into the potassium disulfide solution, the dripping temperature is 75-85 ℃, and the dripping time is 1.5-2.5 h.
Further, in the step 3, after the dropwise addition of the 3-chloropropyltriethoxysilane is finished, the reaction temperature is controlled to be 60-100 ℃ for reaction, and the reaction time is 3-5 hours.
Further, in the step 3, after the dropwise addition of the 3-chloropropyltriethoxysilane is finished, the reaction temperature is controlled to be 80-90 ℃ for reaction, and the reaction time is 3.5-4.
Further, the molar ratio of the potassium hydroxide, the potassium carbonate, the sulfur powder and the 3-chloropropyltriethoxysilane is 1.3:0.4:1.5: 1.
Compared with the preparation method adopting sodium hydrosulfide, sodium carbonate and sulfur powder, the preparation method of bis- [3- (triethoxy silicon) -propyl ] -disulfide provided by the invention has the following innovation points and beneficial effects:
1. the invention adopts potassium hydroxide, potassium carbonate and sulfur powder to react to prepare the potassium disulfide, and the potassium disulfide is taken as a sulfur carrier in the second step of reaction, so that toxic gas is not generated in the reaction process. By replacing the raw materials, the generation of hydrogen sulfide gas is avoided, the process is safer, and the production cost is reduced.
2. The three wastes generated in the preparation process are mainly potassium salt wastewater containing potassium chloride and potassium carbonate, and compared with sodium salt wastewater, the potassium salt wastewater can be directly used for producing potassium fertilizer, so that the method has a certain economic value. Meanwhile, a post-treatment mode of multi-effect evaporation is not needed, so that the post-treatment cost is reduced, and the wastewater has economic value, is more environment-friendly, has good economic benefit and has industrial production value.
The invention provides a preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide, which is characterized in that potassium hydroxide and potassium carbonate are used for replacing sodium hydrosulfide, sodium carbonate and sulfur powder to react, compared with sodium hydroxide, potassium hydroxide has higher reaction activity because the electronic layer of potassium is one layer more than that of sodium, and can react with sulfur under the action of potassium carbonate as a pH buffering agent according to a certain molar ratio to prepare dipotassium disulfide. Meanwhile, dipotassium disulfide can be used as a sulfur donor to react with 3-chloropropyltriethoxysilane, and the dipotassium disulfide and the 3-chloropropyltriethoxysilane react to generate bis- [3- (triethoxysilyl) -propyl ] -disulfide and a byproduct potassium chloride under the action of a phase transfer catalyst. Compared with the traditional sodium hydrosulfide and sodium carbonate process, the preparation method disclosed by the invention not only avoids the generation of hydrogen sulfide gas and ensures the safety in the production process, but also can recycle the wastewater and avoid the situation that the post-treatment implementation is difficult. Therefore, the method has the advantages of avoiding the generation of hydrogen sulfide gas, being simple in post-treatment, being green and environment-friendly and improving the economic benefit.
Detailed Description
The invention is further illustrated by the following examples.
Example 1:
the preparation method of the bis- [3- (triethoxysilicane) -propyl ] -disulfide comprises the following steps:
step 1, reacting potassium hydroxide with water to prepare a potassium hydroxide solution;
step 2, adding potassium carbonate and sulfur powder into a potassium hydroxide solution, wherein the reaction temperature is 60-100 ℃, the reaction time is 1-3 hours, and reacting to obtain a potassium disulfide solution;
step 3, adding a phase transfer catalyst into the potassium disulfide solution, then dropwise adding 3-chloropropyltriethoxysilane, wherein the dropwise adding temperature is 60-90 ℃, and the dropwise adding time is 1-3 h; and after the dropwise addition of the 3-chloropropyltriethoxysilane is finished, controlling the reaction temperature to be 60-100 ℃ for reaction for 3-5 h, and reacting to obtain the bis- [3- (triethoxysilyl) -propyl ] -disulfide.
The molar ratio of the potassium hydroxide to the potassium carbonate to the sulfur powder to the 3-chloropropyltriethoxysilane is (1.2-1.5): (0.3-0.6): 1.2-1.8): 1.
The phase transfer catalyst is one or more of tetrabutylammonium bromide, tetrabutylammonium chloride, dodecyl trimethyl ammonium chloride and tetradecyl trimethyl ammonium chloride.
Example 2:
the preparation method of the bis- [3- (triethoxysilicane) -propyl ] -disulfide comprises the following steps:
step 1, reacting potassium hydroxide with water to prepare a potassium hydroxide solution;
step 2, adding potassium carbonate and sulfur powder into a potassium hydroxide solution, wherein the reaction temperature is 70-80 ℃, the reaction time is 1.5-2.5 hours, and reacting to obtain a potassium disulfide solution;
step 3, adding a phase transfer catalyst into the potassium disulfide solution, and then dropwise adding 3-chloropropyltriethoxysilane at the dropping temperature of 75-85 ℃ for 1.5-2.5 h; and after the dropwise addition of the 3-chloropropyltriethoxysilane is finished, controlling the reaction temperature to be 80-90 ℃ for reaction for 3.5-4 h, and reacting to obtain the bis- [3- (triethoxysilyl) -propyl ] -disulfide.
The molar ratio of the potassium hydroxide, the potassium carbonate, the sulfur powder and the 3-chloropropyltriethoxysilane is 1.3:0.4:1.5: 1.
The phase transfer catalyst is one or more of tetrabutylammonium bromide, tetrabutylammonium chloride, dodecyl trimethyl ammonium chloride and tetradecyl trimethyl ammonium chloride.
Example 3:
the preparation method of the bis- [3- (triethoxysilicane) -propyl ] -disulfide comprises the following steps:
step 1, adding 80g of aqueous solution containing 36.34g of potassium hydroxide into a 500mL flask to prepare a potassium hydroxide solution;
step 2, adding 27.55g of potassium carbonate and 23.92g of sulfur powder into a potassium hydroxide solution, controlling the reaction temperature to be 80 ℃, and reacting for 2 hours under the temperature condition to obtain a potassium disulfide solution;
and 3, adding 2g of tetrabutylammonium bromide into the potassium disulfide solution, stirring for about 10 minutes, and then dropwise adding 120g of 3-chloropropyltriethoxysilane under the condition that the reaction temperature is controlled to be 75 ℃ for 2 hours. After the dropwise addition of the 3-chloropropyltriethoxysilane is finished, carrying out heat preservation reaction at the temperature of 90 ℃ for 4 hours. After the reaction, liquid separation, suction filtration and distillation post-treatment are carried out, and 115.83g of colorless to light yellow transparent liquid, namely the bis- [3- (triethoxysilyl) -propyl ] -disulfide, is finally obtained.
The calculated yield of the 3-chloropropyltriethoxysilane is 97.88 percent, the total sulfur content is 14.27 percent, the chlorine content is 0.25 percent, and the impurity content is 2.93 percent, thereby meeting the requirements of the technical standards.
Example 4:
the preparation method of the bis- [3- (triethoxysilicane) -propyl ] -disulfide comprises the following steps:
step 1, adding 90g of aqueous solution containing 42.46g of potassium hydroxide into a 500mL flask to prepare potassium hydroxide solution;
step 2, adding 31g of potassium carbonate and 28.7g of sulfur powder into a potassium hydroxide solution, controlling the reaction temperature to be 100 ℃, and reacting for 3 hours under the temperature condition to obtain a potassium disulfide solution;
and 3, adding 2g of tetrabutylammonium bromide into the potassium disulfide solution, stirring for about 10 minutes, and then dropwise adding 135g of 3-chloropropyltriethoxysilane under the condition that the reaction temperature is controlled to be 80 ℃ for 1.5 hours. After the dropwise addition of the 3-chloropropyltriethoxysilane is finished, carrying out heat preservation reaction at the temperature of 85 ℃ for 4.5 h. After the reaction, liquid separation, suction filtration and distillation post-treatment are carried out, and 129.35g of colorless to light yellow transparent liquid, namely the bis- [3- (triethoxysilyl) -propyl ] -disulfide, is finally obtained.
The calculated yield of the 3-chloropropyltriethoxysilane is 97.15 percent, the total sulfur content is 14.86 percent, the chlorine content is 0.27 percent, the impurity content is 3.02 percent, and the requirements of the technical standards are met.
Example 5:
the preparation method of the bis- [3- (triethoxysilicane) -propyl ] -disulfide comprises the following steps:
step 1, adding 90g of aqueous solution containing 42.4g of potassium hydroxide into a 500mL flask to prepare potassium hydroxide solution;
step 2, adding 37.31g of potassium carbonate and 25.92g of sulfur powder into a potassium hydroxide solution, controlling the reaction temperature to be 75 ℃, and reacting for 2.5 hours under the temperature condition to obtain a potassium disulfide solution;
and 3, adding 2g of tetrabutylammonium bromide into the potassium disulfide solution, stirring for about 10 minutes, and then dropwise adding 130g of 3-chloropropyltriethoxysilane under the condition that the reaction temperature is controlled at 90 ℃ for 2.5 hours. After the dropwise addition of the 3-chloropropyltriethoxysilane is finished, carrying out heat preservation reaction at the temperature of 95 ℃ for 5 hours. After the reaction, liquid separation, suction filtration and distillation post-treatment are carried out, and 125.14g of colorless to light yellow transparent liquid, namely the bis- [3- (triethoxysilyl) -propyl ] -disulfide, is finally obtained.
The calculated yield of the 3-chloropropyltriethoxysilane is 97.61 percent, the total sulfur content is 14.35 percent, the chlorine content is 0.22 percent, the impurity content is 3.57 percent, and the requirements of the regulations are met.
Example 6:
the preparation method of the bis- [3- (triethoxysilicane) -propyl ] -disulfide comprises the following steps:
step 1, adding 80g of aqueous solution containing 44g of potassium hydroxide into a 500mL flask to prepare a potassium hydroxide solution;
step 2, adding 36.16g of potassium carbonate and 29.77g of sulfur powder into a potassium hydroxide solution, controlling the reaction temperature to be 70 ℃, and reacting for 1.5 hours under the temperature condition to obtain a potassium disulfide solution;
and 3, adding 2g of tetrabutylammonium bromide into the potassium disulfide solution, stirring for about 10 minutes, and then dropwise adding 140g of 3-chloropropyltriethoxysilane under the condition that the reaction temperature is controlled to be 60 ℃, wherein the dropwise adding time is 2 hours. After the dropwise addition of the 3-chloropropyltriethoxysilane is finished, carrying out heat preservation reaction at the temperature of 70 ℃ for 3.5 h. After the reaction, liquid separation, suction filtration and distillation post-treatment are carried out, and 132.83g of colorless to light yellow transparent liquid, namely the bis- [3- (triethoxysilyl) -propyl ] -disulfide, is finally obtained.
The calculated yield of the 3-chloropropyltriethoxysilane is 96.20 percent, the total sulfur content is 14.42 percent, the chlorine content is 0.21 percent, and the impurity content is 2.74 percent, thereby meeting the requirements of the technical standards.
Claims (9)
1. A preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide is characterized by comprising the following steps:
step 1, reacting potassium hydroxide with water to prepare a potassium hydroxide solution;
step 2, adding potassium carbonate and sulfur powder into the potassium hydroxide solution, and reacting to prepare a potassium disulfide solution;
step 3, adding a phase transfer catalyst into a potassium disulfide solution, then dropwise adding 3-chloropropyltriethoxysilane, and reacting to obtain bis- [3- (triethoxysilyl) -propyl ] -disulfide;
the molar ratio of the potassium hydroxide to the potassium carbonate to the sulfur powder to the 3-chloropropyltriethoxysilane is (1.2-1.5) to (0.3-0.6) to (1.2-1.8) to 1.
2. The preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide as claimed in claim 1, wherein in the step 2, the reaction temperature of the potassium hydroxide solution, the potassium carbonate and the sulfur powder is 60-100 ℃, and the reaction time is 1-3 h.
3. The preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide as claimed in claim 1 or 2, wherein in the step 2, the reaction temperature of potassium carbonate and sulfur powder in potassium hydroxide solution is 70-80 ℃, and the reaction time is 1.5-2.5 h.
4. The method for preparing bis- [3- (triethoxysilyl) -propyl ] -disulfide as claimed in claim 1, wherein in step 3, the phase transfer catalyst is any one or more of tetrabutylammonium bromide, tetrabutylammonium chloride, dodecyltrimethylammonium chloride and tetradecyltrimethylammonium chloride.
5. The preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide according to claim 1, wherein in the step 3, 3-chloropropyltriethoxysilane is dripped into the potassium disulfide solution, the dripping temperature is 60-90 ℃, and the dripping time is 1-3 h.
6. The method for preparing bis- [3- (triethoxysilyl) -propyl ] -disulfide according to claim 1 or 5, wherein in the step 3, 3-chloropropyltriethoxysilane is dripped into the potassium disulfide solution, the dripping temperature is 75-85 ℃, and the dripping time is 1.5-2.5 h.
7. The preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide as claimed in claim 1, wherein in step 3, after the dropwise addition of 3-chloropropyltriethoxysilane is completed, the reaction is carried out at a reaction temperature of 60-100 ℃ for 3-5 h.
8. The preparation method of bis- [3- (triethoxysilyl) -propyl ] -disulfide as claimed in claim 1 or 7, wherein in the step 3, after the dropwise addition of 3-chloropropyltriethoxysilane is finished, the reaction is carried out at a reaction temperature of 80-90 ℃ for 3.5-4 h.
9. The method for preparing bis- [3- (triethoxysilyl) -propyl ] -disulfide as claimed in claim 1, wherein the molar ratio of potassium hydroxide, potassium carbonate, sulfur powder and 3-chloropropyltriethoxysilane is 1.3:0.4:1.5: 1.
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| CN113461726A (en) * | 2021-07-20 | 2021-10-01 | 山东阳谷华泰化工股份有限公司 | Preparation method of sulfur-containing silane coupling agent |
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| CN104910202A (en) * | 2014-03-12 | 2015-09-16 | 江苏圣奥化学科技有限公司 | Method for preparing sulfur-containing silane coupling agent |
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