CN115215730A - High-efficiency removal method of aldehyde impurities in alcohols - Google Patents

High-efficiency removal method of aldehyde impurities in alcohols Download PDF

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CN115215730A
CN115215730A CN202210687559.0A CN202210687559A CN115215730A CN 115215730 A CN115215730 A CN 115215730A CN 202210687559 A CN202210687559 A CN 202210687559A CN 115215730 A CN115215730 A CN 115215730A
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sulfonic acid
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aldehyde
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陈晨
吕振国
张巧红
朱祝维
叶易成
翁郭蓥
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Abstract

The invention discloses a method for efficiently removing aldehyde impurities in alcohols, which takes a porous nano silicon dioxide composite material modified by sulfonic acid groups as a catalyst for condensation reaction, is applied to the catalytic conversion removal of trace aldehyde substances in alcohols and the sulfonic acid group modification removalThe porous nano silicon dioxide composite material is made of SiO 2 Using microspheres as a substrate on SiO 2 The surface of the microsphere is connected with sulfonic acid groups. The invention achieves the purpose of introducing a catalytic active center by introducing sulfonic acid groups, obtains high aldehyde impurity removal rate by increasing the specific surface area and promoting the adsorption of substrate molecules, can obtain high conversion rate and product selectivity, can ensure that the conversion rate of substrate aldehydes can reach more than 99.99 percent, can ensure that the selectivity of condensation products can reach more than 99.9 percent, converts aldehyde substances with high hazard into acetal substances with concentration lower than 0.01ppm, extremely low toxicity and higher economic value through condensation reaction, and achieves the multiple purposes of improving the quality of alcohol products, reducing the hazard and improving the economic value.

Description

High-efficiency removal method of aldehyde impurities in alcohols
Technical Field
The invention belongs to the field of catalytic application of solid nano materials, and particularly relates to a high-efficiency removal method of aldehyde impurities in alcohols.
Background
Volatile Organic Compounds (VOCs) are a general term for gaseous or liquid organic compounds that are easily volatilized, and they are easily evaporated into the atmosphere due to their low boiling points. The aldehyde substance is one of common impurities in the alcohol substance, and has high volatility and high toxicity. For example, acetaldehyde (AA) is one of representative substances of VOC, and its trace emission concentration is 0.01ppm, which can enter human body by inhaling vapor and drinking alcoholic beverages. Due to the widespread use of disinfection products, the opportunity for absorption of AA by the average person is significantly increased. AA is a highly reactive compound that interferes with DNA synthesis at multiple sites, causing DNA damage that is closely related to human health. AA was defined by international cancer research institute as "grade 1 carcinogen" (a clear carcinogen).
AA is one of main impurities in ethanol and is inevitably generated on a production line, and the content is usually about 1 to 100 ppm; in addition, due to the easily-oxidizable characteristic of alcohols, the alcohols can be generated by ethanol oxidation during transportation and storage, so that the content of aldehyde substances is increased.
In recent years, removal of aldehydes such as AA from gases and liquids has received much attention. Adsorption and photocatalytic degradation are two main methods for removing aldehydes from alcohols, but are not suitable for removing aldehydes from alcohols because: 1. alcohol substances including ethanol are generally used as an eluent, the molecular polarity, the acid-base property and other properties of the alcohol and aldehyde substances are very similar, and the adsorption of the aldehyde substances in the alcohol substances is difficult to occur; 2. by adopting the photocatalytic degradation method, the degradation of aldehydes and alcohols can be caused at the same time, and the product yield is influenced.
Acetals are a generic name for a class of organic compounds, and are products of condensation of one molecule of aldehyde with two molecules of alcohol, such as acetaldehyde diethyl acetal or benzaldehyde dimethyl acetal, and this type of reaction is called an acetal reaction. Acetals generally have a pleasant fragrance, are significantly reduced in toxicity compared with the corresponding aldehydes, and can be used as food additives. In the traditional catalytic process for industrially synthesizing acetal substances, inorganic acid and alkali are mostly adopted as catalysts, for example: corrosive hydrochloric acid, sodium hydroxide, and the like. The use of homogeneous inorganic acids and bases can lead to equipment corrosion, increased separation costs, and increased environmental pressures. The development of heterogeneous catalysts is considered to be an important way for solving the environmental protection pressure and realizing green production in the process.
The invention provides a novel method for removing aldehyde impurities in alcohols by chemical conversion, aiming at the defects of the existing method for removing the aldehyde substances in the alcohols, and the method takes solid acid as a catalyst and converts aldehyde into acetal substances by utilizing the acetal reaction which can occur between the aldehyde substances and the alcohols, thereby obtaining excellent removal effect.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for efficiently removing aldehyde impurities in alcohols, aiming at the defects of the prior art, the conversion rate of substrate aldehydes can reach more than 99.99 percent, the selectivity of a condensation product can reach more than 99.9 percent, aldehyde substances with high hazard can be converted into acetal substances with concentration lower than 0.01ppm, extremely low toxicity and higher economic value through condensation reaction, and the multiple purposes of improving the quality of alcohol products, reducing the hazard and improving the economic value are achieved.
The technical scheme adopted by the invention for solving the technical problems is as follows: high-efficiency removal method of aldehyde impurities in alcohols, and method thereofThe method takes a porous nano-silica composite material modified by sulfonic acid groups as a catalyst of condensation reaction, is applied to the catalytic conversion removal of trace aldehyde substances in alcohol substances, and takes SiO as the porous nano-silica composite material modified by sulfonic acid groups 2 Microspheres as a substrate on SiO 2 The surface of the microsphere is connected with sulfonic acid groups.
Preferably, the porous nano-silica composite material modified by sulfonic acid groups has a general formula of m (SO) 3 H)-SiO 2 Wherein m is the mass percentage content of the sulfonic acid group in the porous nano-silica composite material modified by the sulfonic acid group, and the numerical range of m is 0.01 to 66 percent; the SiO 2 The particle diameter of the microsphere is 10 to 100 nanometers, and the specific surface area is 30 to 500m 2 /g。
Preferably, the concentration of the trace aldehyde substance in the alcohol substance is in the range of 0.1 to 5000ppm under the liquid phase reaction conditions.
Preferably, the removal process is realized by condensation reaction, the substrate molecules of the reaction are aldehyde and alcohol, the product of the reaction is corresponding acetal product, the reaction temperature of the condensation reaction is between room temperature and 90 ℃, and the reaction time is between 5 and 240 minutes.
Furthermore, the reaction temperature of the condensation reaction is 20-30 ℃, and the reaction time is 40-90 minutes.
Preferably, the introduction of the sulfonic acid group is realized by hydrolyzing mercaptoorganosilane and then oxidizing with hydrogen peroxide or potassium permanganate.
Further, the sulfonic acid group modified porous nano-silica composite material is prepared by adopting a reverse microemulsion method, and the specific preparation method comprises the following steps:
1) Mixing a surfactant, an organic phase and a cosurfactant to form an inverse microemulsion A, and mixing ammonia water with the mass concentration of 25-28% and deionized water to form a solution B;
2) Mixing low-carbon alcohol orthosilicate and mercaptoorganosilane serving as silicon sources to prepare a solution C, wherein the low-carbon alcohol orthosilicate is methyl orthosilicate or ethyl orthosilicate;
3) Mixing the inverse microemulsion A with the solution B to obtain a solution D, adding the solution C into the solution D under the condition of stirring, wherein the mixed solution comprises the following components in percentage by mass: 22% of surfactant, 8% of water, 52% of organic phase, 3% of ammonia water, 12% of cosurfactant, 0.3-6% of low carbon alcohol orthosilicate ester and 0.3-6% of mercaptoorganosilane; aging the mixed solution for 2-48 h, adding ethanol or acetone with the mass 5-10 times that of the low carbon alcohol orthosilicate for demulsification, and centrifuging to collect solids; and then washing the solid with ethanol for 2-6 times to remove the surfactant, drying at 80-150 ℃ to obtain a solid synthetic material, oxidizing the synthetic material with hydrogen peroxide or potassium permanganate, and finally obtaining the granular sulfonic acid group modified porous nano-silica composite material with uniform size.
The sulfonic acid group modified porous nano silicon dioxide composite material prepared by adopting the reverse microemulsion method has uniform and stable size and is prepared on SiO 2 The surface of the microsphere is stably connected with sulfonic acid groups, so that a solid acid catalyst with high specific surface area and suitable acid amount can be provided for removing aldehyde impurities in alcohol substances. When the catalyst is applied to the removal of aldehyde impurities in alcohol substances, the excellent removal effect of the aldehyde impurities can be obtained under the mild condensation reaction condition.
Preferably, the specific method for oxidizing by using hydrogen peroxide or potassium permanganate comprises the following steps: 1g of the synthetic material was mixed with 20mL of 30% H 2 O 2 Or mixing potassium permanganate solution, adding 20mL of 1mol/L hydrochloric acid solution, carrying out acidification and oxidation for 4 hours at the rotating speed of 200r under the water bath condition of 400 ℃, and finally washing with clear water to be neutral.
Further, in the step 2), the molar ratio of the mercaptoorganosilane to the lower alcohol orthosilicate is in a range from 0.005 to 1.5, so as to obtain the best catalytic performance.
Preferably, the surfactant is an anionic surfactant, a long-chain nonionic surfactant or a cationic surfactant, the anionic surfactant is sodium linear alkyl benzene sulfonate or sodium alpha-alkenyl sulfonate, and the long-chain nonionic surfactant is an organic surfactantThe surfactant comprises primary amine, np series surfactant or Tween series surfactant, wherein the cationic surfactant is hexadecyl trimethyl ammonium bromide, the organic phase is cyclohexane, n-hexane or toluene, and the cosurfactant is n-butylamine, n-propylamine or cyclohexylamine. Small molecular amine substances such as n-butylamine, n-propylamine or cyclohexylamine are used as cosurfactant and can be added into SiO 2 Rich pore canal structure is manufactured on the surface of the microsphere substrate, so that SiO is formed 2 The microspheres have a high specific surface area.
Compared with the prior art, the invention has the following advantages: the invention relates to a novel method for efficiently removing aldehyde impurities in alcohol substances. The method applies the porous nano-silica composite material modified by sulfonic acid groups to the catalytic removal of aldehyde impurities in alcohol substances, achieves the purpose of introducing catalytic active centers by introducing the sulfonic acid groups, obtains high aldehyde impurity removal rate by increasing the specific surface area and promoting the adsorption of substrate molecules, can obtain high conversion rate and product selectivity, can ensure that the conversion rate of substrate aldehydes can reach more than 99.99 percent, and the selectivity of condensation products can reach more than 99.9 percent, converts the aldehyde substances with high hazard into acetal substances with concentration lower than 0.01ppm, extremely low toxicity and higher economic value by condensation reaction, and achieves the multiple purposes of improving the quality of the alcohol products, reducing the hazard and improving the economic value.
Drawings
FIG. 1 is a scanning electron micrograph of Material A;
fig. 2 is a nitrogen adsorption/desorption curve of material a.
Detailed Description
The invention is described in further detail below with reference to the accompanying examples.
Material A (33 SO) 3 H-SiO 2 ) The preparation of (1): 15g of Np-7, 35.1g of cyclohexane and 8.1g of n-butylamine are mixed to obtain reverse microemulsion A;5.35g of deionized water is added with 2g of ammonia water to obtain a solution B; mixing 1.20g of methyl orthosilicate and 0.67g of 3-mercaptopropyltriethoxysilane to obtain a solution C; pouring the solution B into the inverse microemulsion A to obtain a solution D, adding the solution C into the solution D under vigorous stirring, and aging for 9 hours; then, the user can use the device to perform the operation,adding 10mL of acetone for demulsification, stirring for 30 minutes, and centrifuging to obtain a solid; adding 30mL of ethanol into the solid, heating and stirring at 80 ℃ for 10 minutes, centrifuging, and repeating the step for multiple times until the surfactant is completely removed; drying at 80 ℃ to obtain a solid synthetic material; 1g of synthetic material was mixed with 20mL of 30% H 2 O 2 After the solutions are mixed, adding 20mL 1mol/L hydrochloric acid solution, then carrying out acidification and oxidation for 4h at the rotating speed of 200r under the water bath condition of 400 ℃, finally washing with clear water to be neutral, and finally obtaining a granular material A with uniform size, namely the sulfonic acid group modified porous nano-silica composite material 33SO 3 H-SiO 2 。
The scanning electron micrograph of the material A is shown in figure 1, and the nitrogen adsorption and desorption curve is shown in figure 2. From FIG. 2, it can be calculated that the specific surface area of the material A reaches 461m 2 The/g, the average aperture is 5.1nm, which shows that the mesoporous silicon dioxide material has rich mesoporous channels and high specific surface area.
Preparation of materials B-I: the preparation method of the materials B to I is the same as that of the material A, but the difference is that the content of the sulfonic acid group is different from that of the material A, and the materials B to I are respectively as follows: material B:0.01SO 3 H-SiO 2 (ii) a Material C:2SO 3 H-SiO 2 (ii) a Material D:5SO 3 H-SiO 2 (ii) a Material E:15SO 3 H-SiO 2 (ii) a Material F:28SO 3 H-SiO 2 (ii) a Material G:40SO 3 H-SiO 2 (ii) a Material H:50SO 3 H-SiO 2 (ii) a Material I:66SO 3 H-SiO 2 。
1. Example 1: application of material A in removal of acetaldehyde in ethanol
The material A is used as a catalyst for removing acetaldehyde in ethanol: taking 0.1g of the material A as a catalyst, adding into a reaction kettle, and then adding 5.8g of acetaldehyde and 6.4g of ethanol; starting a stirring device, reacting at the temperature of 25 ℃, and stopping the reaction after 30 minutes; and (3) taking out part of reactants after cooling, quantitatively analyzing acetaldehyde and ethanol and a product diethoxyethane by adopting a gas chromatograph internal standard method, and calculating the conversion rate and selectivity according to the change of the reactants and the product before and after the reaction. The reaction conditions and results are shown in Table 1.
2. Example 2 to example 26: application of materials A to I in removal of aldehyde impurities in different alcohols
The materials A to I are respectively applied to the removal of aldehyde impurities in different alcohols, the specific reactants and reaction conditions are shown in Table 1, and the reaction conversion rate, namely the removal rate of the aldehyde impurities, is also shown in Table 1.
TABLE 1 reaction results of catalytic removal of aldehyde impurities in alcohols with different catalysts
Figure BDA0003700216980000051

Claims (10)

1. The method is characterized in that a porous nano-silica composite material modified by sulfonic acid groups is used as a catalyst for condensation reaction and applied to catalytic conversion removal of trace aldehyde substances in alcohols, and the porous nano-silica composite material modified by the sulfonic acid groups is SiO 2 Microspheres as a substrate on SiO 2 The surface of the microsphere is connected with sulfonic acid groups.
2. The method for efficiently removing aldehyde impurities in alcohols according to claim 1, wherein the porous nano-silica composite material modified by sulfonic acid groups has a general formula of m (SO) 3 H)-SiO 2 Wherein m is the mass percentage content of the sulfonic acid group in the porous nano-silica composite material modified by the sulfonic acid group, and the numerical range of m is 0.01 to 66 percent; the SiO 2 The particle diameter of the microsphere is 10 to 100 nanometers, and the specific surface area is 30 to 500m 2 /g。
3. The method as claimed in claim 1, wherein the concentration of the trace aldehydes in the alcohols is 0.1-5000 ppm under the liquid phase reaction condition.
4. The method of claim 1, wherein the removal process is performed by condensation reaction, the substrate molecules of the reaction are aldehyde and alcohol, the reaction product is the corresponding acetal product, the reaction temperature of the condensation reaction is between room temperature and 90 ℃, and the reaction time is between 5 minutes and 240 minutes.
5. The method as claimed in claim 4, wherein the condensation reaction is carried out at 20-30 deg.C for 40-90 min.
6. The method for efficiently removing the aldehyde impurities in the alcohols according to any one of claims 1 to 5, wherein the introduction of the sulfonic acid groups is realized by hydrolyzing mercaptoorganosilane and oxidizing with hydrogen peroxide or potassium permanganate.
7. The method for efficiently removing the aldehyde impurities in the alcohols according to claim 6, wherein the porous nano-silica composite material modified by the sulfonic acid groups is prepared by a reversed-phase microemulsion method, and the specific preparation method comprises the following steps:
1) Mixing a surfactant, an organic phase and a cosurfactant to form an inverse microemulsion A, and mixing ammonia water with the mass concentration of 25-28% and deionized water to form a solution B;
2) Mixing low-carbon alcohol orthosilicate and mercaptoorganosilane serving as silicon sources to prepare a solution C, wherein the low-carbon alcohol orthosilicate is methyl orthosilicate or ethyl orthosilicate;
3) Mixing the reversed-phase microemulsion A with the solution B to obtain a solution D, adding the solution C into the solution D under the condition of stirring, wherein the obtained mixed solution comprises the following components in percentage by mass: 22% of surfactant, 8% of water, 52% of organic phase, 3% of ammonia water, 12% of cosurfactant, 0.3-6% of low carbon alcohol orthosilicate ester and 0.3-6% of mercaptoorganosilane; aging the mixed solution for 2-48 h, adding ethanol or acetone with the mass 5-10 times that of the low-carbon alcohol orthosilicate for demulsification, and centrifuging to collect solids; and then washing the solid with ethanol for 2-6 times to remove the surfactant, drying at 80-150 ℃ to obtain a solid synthetic material, oxidizing the synthetic material with hydrogen peroxide or potassium permanganate, and finally obtaining the granular sulfonic acid group modified porous nano-silica composite material with uniform size.
8. The method for efficiently removing the aldehyde impurities in the alcohols according to claim 7, wherein the specific method for oxidizing by hydrogen peroxide or potassium permanganate comprises the following steps: 1g of the synthetic material was mixed with 20mL of 30% H 2 O 2 Or after mixing the potassium permanganate solution, adding 20mL of 1mol/L hydrochloric acid solution, carrying out acidification and oxidation for 4 hours at the rotating speed of 200r under the water bath condition of 400 ℃, and finally washing with clear water to be neutral.
9. The method as claimed in claim 7, wherein the molar ratio of mercaptoorganosilane to lower orthosilicic acid alcohol ester in step 2) is in the range of 0.005-1.5.
10. The method as claimed in claim 7, wherein the surfactant is an anionic surfactant, a long-chain nonionic surfactant or a cationic surfactant, the anionic surfactant is sodium linear alkylbenzene sulfonate or sodium alpha-olefin sulfonate, the long-chain nonionic surfactant is an organic primary amine, an Np series surfactant or a tween series surfactant, the cationic surfactant is hexadecyl trimethyl ammonium bromide, the organic phase is cyclohexane, n-hexane or toluene, and the cosurfactant is n-butylamine, n-propylamine or cyclohexylamine.
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彭建兵等: "磺酸基官能化介孔材料的表征及其催化性能", 《精细化工中间体》, vol. 41, no. 1, pages 61 - 65 *

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