CN110548542A - Reaction control phase transfer catalyst for chloropropene epoxidation and preparation method thereof - Google Patents
Reaction control phase transfer catalyst for chloropropene epoxidation and preparation method thereof Download PDFInfo
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- CN110548542A CN110548542A CN201910890749.0A CN201910890749A CN110548542A CN 110548542 A CN110548542 A CN 110548542A CN 201910890749 A CN201910890749 A CN 201910890749A CN 110548542 A CN110548542 A CN 110548542A
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
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- C07—ORGANIC CHEMISTRY
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- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
- B01J2231/72—Epoxidation
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Abstract
The invention discloses a reaction control phase transfer catalyst for chloropropene epoxidation and a preparation method thereof, belonging to the field of catalytic chemistry. The specific synthesis method comprises the following steps: dissolving K-type phosphotungstic acid in 30% hydrogen peroxide for oxidation reaction to obtain a peroxyphosphotungstic acid aqueous solution, then dropwise adding the peroxyphosphotungstic acid aqueous solution into an ethanol solution of hexadecyltrimethylammonium chloride, and stirring and reacting for 3 hours at the temperature of 40 ℃. Filtering to obtain white powder after the reaction is finished, and washing with water, washing with absolute ethyl alcohol and drying in vacuum to obtain the hexadecyl trimethyl peroxyphosphotungstic acid catalyst. The method takes hexadecyl trimethyl peroxyphosphotungstic acid as a catalyst, chloropropene and hydrogen peroxide as raw materials, and the yield of the epoxy chloropropane prepared by a one-pot method under the condition of no solvent and no auxiliary agent reaches 97.7 percent, the selectivity is more than 99 percent, and the product yield reaches more than 96 percent. After the reaction is finished, the catalyst is separated out, and the catalyst is recovered by a filtration method. The catalytic reaction process has the advantages of simple operation, mild reaction conditions, low production cost, stable catalyst property and convenient recovery, and is beneficial to industrial production.
Description
Technical Field
The invention relates to the field of catalytic chemistry, in particular to a reaction control phase transfer catalyst for chloropropene epoxidation and a preparation method thereof.
Background
Epichlorohydrin is an important organic synthetic intermediate and a fine chemical product, 85 percent of the epichlorohydrin is used for producing epoxy resin globally, and China is the largest producing country and consuming country of epoxy resin. The propylene high-temperature chlorination method and the propylene acetate method are main processes for producing epoxy chloropropane at the present stage, and the two methods are mature and stable in operation, but inevitably generate waste water, have high production energy consumption and seriously corrode equipment. Therefore, the development of a simple, efficient and green epichlorohydrin synthesis process is significant.
Hydrogen peroxide, as a green oxygen source, is widely used in research on epoxidation of olefins. The method for directly synthesizing the epichlorohydrin is the simplest method by catalyzing and epoxidizing the chloropropene by using the hydrogen peroxide as an oxidant. Japanese unexamined patent publication Hei 4-5028 and patent CN1639143A disclose a method for synthesizing epichlorohydrin by epoxidation of propylene with hydrogen peroxide using titanosilicate as a catalyst. The titanosilicate catalysts are relatively expensive to prepare, the process is not mature enough, and sufficient catalytic activity is not obtained in the known production methods. Patent CN 101205219B reports a reaction process for preparing propylene oxide by directly reacting propylene with hydrogen peroxide, which is a clean oxygen source, under the action of a reaction-controlled phase transfer catalyst. However, additional organic solvent and phosphate promoter were used in the catalytic reaction system, and the conversion of propylene was only 93%. Similarly, patent CN100575349C reports that in the presence of phosphotungstic acid as a catalyst and alkylphenol ethoxylates as a cocatalyst, hydrogen peroxide is used as an oxidant to directly generate epichlorohydrin, and the excessive chloropropene and an organic auxiliary agent are used in the reaction process, which is not favorable for industrial production.
Under the situation that the environmental protection requirement is more and more strict, the aim of realizing green production becomes the development of enterprises is achieved. In a catalytic reaction system, the preparation of the catalyst which is simple, efficient and easy to recycle is very important.
Disclosure of Invention
The invention provides a method for synthesizing a novel catalyst hexadecyl trimethyl peroxyphosphotungstic acid aiming at the defects in the existing epoxy chloropropane synthesis process. The method is simple and easy to implement, the reaction conditions are mild, the used raw materials are safe and easy to obtain, and the method is convenient for industrial production. Hydrogen peroxide is used as an oxygen source, and cetyl trimethyl peroxyphosphotungstic acid can directly catalyze chloropropene to synthesize epichlorohydrin under the condition of no other organic solvent or auxiliary agent.
The invention is realized by the following technical scheme:
The phosphotungstic acid is easy to dissolve in hydrogen peroxide, and the hydrogen peroxide can oxidize the phosphotungstic acid at room temperature to obtain the peroxyphosphotungstic acid solution. The hexadecyl trimethyl ammonium chloride is easy to dissolve in absolute ethyl alcohol, and the peroxyphosphotungstic acid solution is dripped into the ethanol solution of the hexadecyl trimethyl ammonium chloride at the temperature of 40 ℃, so that the hexadecyl trimethyl peroxyphosphotungstic acid solid can be obtained. Reacting for 3 hours at constant temperature to ensure that the reaction is more sufficient. The crude catalyst is obtained by filtration, and a small amount of unreacted reactants are washed away by water washing and ethanol washing to obtain a pure compound.
Advantageous effects
In the process of catalyzing and epoxidizing chloropropene by the synthesized hexadecyl trimethyl peroxyphosphotungstic acid, other organic solvents and auxiliaries are not needed, the molar ratio of chloropropene to hydrogen peroxide is 1:1, the yield of epichlorohydrin is up to 97.7%, the selectivity is more than 99%, and the yield is 96%. The catalyst belongs to a reaction control phase transfer catalyst, and after the reaction is finished, the catalyst is separated out and filtered for recovery. The catalyst still has higher catalytic activity after 7 times of circulation, and has good selectivity, and the yield of the epichlorohydrin obtained by the reaction is high.
In conclusion, the catalyst synthesized by the method is used for catalyzing chloropropene to synthesize epoxy chloropropane, and has the advantages of simple process operation, mild reaction conditions, low production cost and convenient catalyst recovery, thereby being more beneficial to industrial implementation.
Drawings
to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings required for the embodiments will be briefly described below, and the following drawings only show some embodiments of the present invention and thus should not be construed as limiting the scope fig. 1 is an infrared spectrum of hexadecyl trimethyl peroxyphosphotungstic acid provided in example 1 of the present invention, 1075 cm -1 is an absorption peak of P — O bond in PO 4 3- , 955 cm -1 is an absorption peak of W = O bond, 845 cm -1 is an absorption peak of O-O bond, 785, 715, 645 cm -1 are absorption peaks of cation.
Detailed Description
The following examples are further illustrative of the nature of the invention and are not to be construed as limiting the invention. The starting materials used in the present invention are commercially available.
example 1
1.152 kg of phosphotungstic acid solid and 1.7L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 40 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 40 ℃. After the reaction is finished, cooling to room temperature, filtering under reduced pressure to obtain crude catalyst white powder, washing the white powder with 40L of distilled water, then washing with 10L of ethanol, filtering, and drying in vacuum at 40 ℃ for 6 h to obtain 735 g of white catalyst powder in total.
Example 2
1.152 kg of phosphotungstic acid solid and 1.7L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 45 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 45 ℃. After the reaction is finished, cooling to room temperature, filtering under reduced pressure to obtain crude catalyst white powder, washing the white powder with 40L of distilled water, then washing with 10L of ethanol, filtering, and drying in vacuum at 40 ℃ for 6 h to obtain 728 g of white catalyst powder in total.
example 3
1.152 kg of phosphotungstic acid solid and 1.7L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 50 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 50 ℃. After the reaction is finished, cooling to room temperature, filtering under reduced pressure to obtain crude catalyst white powder, washing the white powder with 40L of distilled water, then washing with 10L of ethanol, filtering, and drying in vacuum at 40 ℃ for 6 h to obtain 713 g of white catalyst powder in total.
Example 4
1.152 kg of phosphotungstic acid solid and 1.7L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 55 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding, continuously stirring and reacting for 3 h at 55 ℃. After the reaction is finished, the mixture is cooled to room temperature, reduced pressure filtration is carried out to obtain a crude catalyst white powder, the white powder is washed by 40L of distilled water and then by 10L of ethanol, filtration is carried out, vacuum drying is carried out for 6 h at 40 ℃, and 708 g of white catalyst powder in total is obtained.
Example 5
1.152 kg of phosphotungstic acid solid and 1.7L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 60 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 60 ℃. After the reaction, the reaction mixture was cooled to room temperature, and filtered under reduced pressure to obtain a crude catalyst white powder, which was washed with 40L of distilled water and then 10L of ethanol, filtered, and vacuum-dried at 40 ℃ for 6 hours to obtain 694 g in total of white catalyst powder.
Example 6
1.152 kg of phosphotungstic acid solid and 1.5L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 40 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 40 ℃. After the reaction is finished, cooling to room temperature, filtering under reduced pressure to obtain crude catalyst white powder, washing the white powder with 40L of distilled water, then washing with 10L of ethanol, filtering, and drying in vacuum at 40 ℃ for 6 h to obtain 732 g of white catalyst powder in total.
Example 7
1.152 kg of phosphotungstic acid solid and 1.3L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 40 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 40 ℃. After the reaction is finished, cooling to room temperature, filtering under reduced pressure to obtain crude catalyst white powder, washing the white powder with 40L of distilled water, then washing with 10L of ethanol, filtering, and drying in vacuum at 40 ℃ for 6 h to obtain 725 g of white catalyst powder in total.
Example 8
1.152 kg of phosphotungstic acid solid and 1.1L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 40 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 40 ℃. After the reaction is finished, cooling to room temperature, filtering under reduced pressure to obtain crude catalyst white powder, washing the white powder with 40L of distilled water, then washing with 10L of ethanol, filtering, and drying in vacuum at 40 ℃ for 6 h to obtain 718 g of white catalyst powder in total.
Example 9
1.152 kg of phosphotungstic acid solid and 1.0L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 40 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 40 ℃. After the reaction is finished, cooling to room temperature, filtering under reduced pressure to obtain crude catalyst white powder, washing the white powder with 40L of distilled water, then washing with 10L of ethanol, filtering, and drying in vacuum at 40 ℃ for 6 h to obtain 710 g of white catalyst powder in total.
Example 10
1.152 kg of phosphotungstic acid solid and 0.9L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 40 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 40 ℃. After the reaction is finished, cooling to room temperature, filtering under reduced pressure to obtain crude catalyst white powder, washing the white powder with 40L of distilled water, then washing with 10L of ethanol, filtering, and drying in vacuum at 40 ℃ for 6 h to obtain 706 kg of white catalyst powder in total.
Example 11
1.152 kg of phosphotungstic acid solid and 0.85L of 30% hydrogen peroxide are added into a 5L glass reaction kettle, and the mixture is stirred for reaction at room temperature in a dark place. Meanwhile, 0.397 kg of hexadecyl trimethyl ammonium chloride and 8L of absolute ethyl alcohol are added into a 50L glass reaction kettle and heated and dissolved at 40 ℃. After 2 h, dropwise adding the peroxyphosphotungstic acid solution obtained from a 5L glass reaction kettle into a 50L glass reaction kettle by using a metering pump, and after dropwise adding is finished, continuously stirring and reacting for 3 h at 40 ℃. After the reaction is finished, cooling to room temperature, filtering under reduced pressure to obtain crude catalyst white powder, washing the white powder with 40L of distilled water, then washing with 10L of ethanol, filtering, and drying in vacuum at 40 ℃ for 6 h to obtain total 700 g of white catalyst powder.
Application example 12
454g of 30% hydrogen peroxide, 306 g of chloropropene, and 53.4 g of the catalyst obtained in examples 1 to 11 were charged in a 5L glass reactor. And (3) reacting the mixed solution at 55 ℃ for 6 h, cooling, separating the solution (the generated epichlorohydrin is at the lower layer), detecting the conversion rate and the selectivity by gas chromatography, and calculating to obtain the yield of the epichlorohydrin. The above experiment was repeated a plurality of times, and the results are shown in table 1.
Application example 13
Table 1 shows that the catalyst obtained under the conditions of example 1 has the best catalytic effect, and therefore the catalyst in example 1 was used for the purpose of research on the effect of recycling. The reaction conditions were the same as in application example 12, and 454g of 30% hydrogen peroxide, 306 g of chloropropene, and 53.4 g of the catalyst prepared in example 1 were charged in a 5L glass reactor. Reacting the mixed solution at 55 ℃ for 6 h, cooling, separating liquid, cooling the lower-layer epichlorohydrin to 10 ℃, separating out a large amount of white catalyst solid, performing suction filtration, washing with absolute ethyl alcohol, and drying, wherein the single-pass recovery rate of the catalyst is 93%. The cycle test was carried out with the recovered catalyst, the conversion and selectivity were checked by gas chromatography, and the yield of epichlorohydrin was calculated, with the results shown in table 2.
TABLE 1 Effect of catalysts prepared under different conditions on catalyzing chloropropene to prepare epichlorohydrin
TABLE 2 catalyst recycle effect
The embodiments described above are some, but not all embodiments of the invention. The detailed description of the embodiments of the present invention is not intended to limit the scope of the invention as claimed, but is merely representative of selected embodiments of the invention.
Claims (7)
1. A reaction control phase transfer catalyst for chloropropene epoxidation and a preparation method thereof are characterized by comprising the following steps:
Dissolving K-type phosphotungstic acid in 30% hydrogen peroxide for oxidation reaction to obtain a peroxyphosphotungstic acid aqueous solution, then dropwise adding the peroxyphosphotungstic acid aqueous solution into an ethanol solution of hexadecyltrimethylammonium chloride, and stirring and reacting for 3 hours at the temperature of 40 ℃; filtering to obtain white powder after the reaction is finished, and washing with water, washing with absolute ethyl alcohol and drying in vacuum to obtain the hexadecyl trimethyl peroxyphosphotungstic acid catalyst.
2. The reaction-controlled phase transfer catalyst for the epoxidation of chloropropene as claimed in claim 1, wherein the reaction-controlled phase transfer catalyst comprises: the molar ratio of the K-type phosphotungstic acid to the hydrogen peroxide is 1: 20-1: 40.
3. The reaction-controlled phase transfer catalyst for the epoxidation of chloropropene as claimed in claim 1, wherein the reaction-controlled phase transfer catalyst comprises: dissolving K-type phosphotungstic acid in hydrogen peroxide, and stirring the two at room temperature in the dark for reaction for 2 h.
4. The reaction-controlled phase transfer catalyst for the epoxidation of chloropropene as claimed in claim 1, wherein the reaction-controlled phase transfer catalyst comprises: the molar ratio of the K-type phosphotungstic acid to the hexadecyl trimethyl ammonium chloride is (1: 3) - (1): 4.
5. The reaction-controlled phase transfer catalyst for the epoxidation of chloropropene as claimed in claim 1, wherein the reaction-controlled phase transfer catalyst comprises: adding hexadecyl trimethyl ammonium chloride into a proper amount of absolute ethyl alcohol, and stirring and dissolving at 40 ℃.
6. The reaction-controlled phase transfer catalyst for the epoxidation of chloropropene as claimed in claim 1, wherein the reaction-controlled phase transfer catalyst comprises: dropwise and slowly adding the peroxyphosphotungstic acid aqueous solution obtained by the reaction into an ethanol solution of hexadecyltrimethylammonium chloride, and violently stirring and reacting for 3 hours at the temperature of 40 ℃.
7. The reaction-controlled phase transfer catalyst for the epoxidation of chloropropene as claimed in claim 1, wherein the reaction-controlled phase transfer catalyst comprises: cooling after the reaction is finished, filtering under reduced pressure to obtain white powder, washing with a large amount of distilled water, then washing with a small amount of ethanol, and finally drying in vacuum at 30 ℃.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113893875A (en) * | 2021-11-12 | 2022-01-07 | 泉州师范学院 | Preparation method of double-bond epoxidation phase transfer catalyst with high recovery rate |
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| CN1900071A (en) * | 2005-07-21 | 2007-01-24 | 中国科学院大连化学物理研究所 | Process for preparing epoxy chloropropane |
| CN107824219A (en) * | 2017-11-22 | 2018-03-23 | 山东玉皇化工有限公司 | A kind of phase transfer catalyst and preparation method thereof and a kind of method that glutaric acid is prepared using cyclopentene |
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