CN116283662A - Method for removing acetone in industrial acetonitrile - Google Patents

Method for removing acetone in industrial acetonitrile Download PDF

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Publication number
CN116283662A
CN116283662A CN202310042866.8A CN202310042866A CN116283662A CN 116283662 A CN116283662 A CN 116283662A CN 202310042866 A CN202310042866 A CN 202310042866A CN 116283662 A CN116283662 A CN 116283662A
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Prior art keywords
acetonitrile
acetone
industrial
ethanol
removing acetone
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CN202310042866.8A
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Inventor
庆九
俞新南
朱小刚
周新建
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NANTONG ACETIC ACID CHEMICAL CO Ltd
Nantong Liyang Chemical Co ltd
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NANTONG ACETIC ACID CHEMICAL CO Ltd
Nantong Liyang Chemical Co ltd
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Priority to CN202310042866.8A priority Critical patent/CN116283662A/en
Publication of CN116283662A publication Critical patent/CN116283662A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C07C253/34—Separation; Purification
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/04—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of alkali metals, alkaline earth metals or magnesium
    • B01J20/041—Oxides or hydroxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C255/03—Mononitriles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00—Aspects relating to sorbent materials
    • B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/42—Materials comprising a mixture of inorganic materials

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to the field of chemical industry, in particular to the field of IPC C07C, and more particularly relates to a method for removing acetone in industrial acetonitrile. The method for removing the acetone in the industrial acetonitrile comprises the following steps: s1, after uniformly mixing a carbon material and an ethanol aqueous solution, dropwise adding a first solution, heating and stirring, and then continuously heating to recover a solvent to obtain a residual material; calcining the rest materials at high temperature to obtain a composite material; s2, installing the composite material body prepared in the step S1 into an adsorption tower, setting temperature and pressure, introducing industrial acetonitrile into the adsorption tower by a pump at a certain flow speed in the direction of gravity, and collecting acetonitrile at a liquid outlet at the top of the tower after adsorbing the acetone. The method utilizes the synergistic adsorption effect of the carbon material and the magnesium oxide on the acetone, efficiently removes trace acetone in the acetonitrile, has simple process flow, is suitable for industrial application, and has good application prospect.

Description

Method for removing acetone in industrial acetonitrile
Technical Field
The invention relates to the field of chemical industry, in particular to the field of IPC C07C, and more particularly relates to a method for removing acetone in industrial acetonitrile.
Background
Acetonitrile is a fairly widely used organic chemical raw material. Acetonitrile is a common polar aprotic solvent in the laboratory, which can be used for the synthesis of drugs and intermediates thereof; in organic synthesis, malononitrile can be produced by reaction with cyanogen chloride; acetonitrile can also be used as a mobile phase separation molecule, and is commonly used for column chromatography and advanced high performance liquid chromatography, but the purity and quality of a mobile phase acetonitrile solvent have important influence on analysis results and an instrument.
Several methods for removing acetonitrile are introduced in the prior art: (1) the removal modes of impurities such as aldehyde ketone, unsaturated nitrile compounds and the like in acetonitrile are as follows: removing unsaturated organic impurities by a strong oxidant, and then obtaining high-purity acetonitrile through adsorption and rectification; (2) the method for removing water in acetonitrile comprises the following steps: extracting, separating and dewatering crude acetonitrile by an organic solvent, and rectifying an extract to obtain finished product refined acetonitrile; (3) and (3) carrying out adsorption treatment on industrial acetonitrile by using the modified activated carbon composite adsorbent, and filtering by using a filter membrane to remove doped solid impurities so as to obtain the high-purity acetonitrile.
The patent of application number CN202011213917.1 proposes a purification method of gradient-grade chromatographic pure acetonitrile, wherein the purification method mainly comprises the steps of sequentially carrying out oxidation neutralization reaction, adsorption column impurity removal treatment and rectification treatment on industrial acetonitrile, and finally obtaining the chromatographic pure acetonitrile. However, this purification method is costly and complicated in process.
The patent of application number CN201910233669.8 provides a method and apparatus for purifying acetonitrile, which mainly obtains finished product refined acetonitrile through at least one extraction and rectification step. The method has the defects of high production energy consumption, large equipment occupation area, high cost and the like of the treatment method.
The patent of application number CN201810779749.9 discloses a method for purifying pesticide residue grade acetonitrile, which mainly utilizes a magnetic ferric oxide active carbon composite adsorbent to adsorb and purify pesticide residue grade pure acetonitrile, and then obtains finished acetonitrile through filtration. The method has the defects of high material cost, low composite property of the adsorption material and the like.
There are various ways to remove impurities from acetonitrile in the prior art, but there is no technology for treating acetone in industrial acetonitrile with modified adsorption composites. Therefore, the method for treating the acetone in the industrial acetonitrile is provided, and the excellent impurity removal effect is achieved through the specific adsorption of the modified adsorption composite material to the acetone in the acetonitrile.
The original technology has the following defects: the method for removing impurities in acetonitrile by the original process basically adopts a redox reaction or multistage rectification mode to remove acetone in acetonitrile products. However, these methods often introduce other impurities or have the disadvantage of high energy consumption for impurity removal.
Disclosure of Invention
In order to solve the above problems, the present invention provides, in a first aspect, a method for removing acetone in industrial acetonitrile, comprising the steps of:
s1, after uniformly mixing a carbon material and an ethanol aqueous solution, dropwise adding a first solution, heating and stirring, and then continuously heating to recover a solvent to obtain a residual material; calcining the rest materials at high temperature to obtain a composite material;
s2, installing the composite material body prepared in the step S1 into an adsorption tower, setting temperature and pressure, introducing industrial acetonitrile into the adsorption tower by a pump at a certain flow speed in the direction of gravity, and collecting acetonitrile at a liquid outlet at the top of the tower after adsorbing the acetone.
Preferably, the carbon material in step S1 includes one or more of carbon nanotubes, graphene, activated carbon, and carbon fibers.
Preferably, the carbon nanotube has an outer diameter of 5-30nm and a specific surface area of 50-200m 2 /g; further preferably, the carbon nanotubes have an outer diameter of 10-20nm and a specific surface area of 100-160m 2 /g。
In some preferred embodiments, the carbon nanotubes are purchased from Shenzhen nanoport Inc., model S-MWNT-1020.
Preferably, the granularity of the graphene is 10-30 mu m, and the bulk density is 0.05-0.1g/cm 3 The method comprises the steps of carrying out a first treatment on the surface of the Further preferably, the graphene has a particle size of 20 μm and is densely packedThe degree of the reaction is 0.07g/cm 3 。
In some preferred embodiments, the graphene is purchased from Qingdao rock-sea carbon materials Inc., model HGP-20.
Preferably, the activated carbon is derived from wood chips.
In some preferred embodiments, the activated carbon is purchased from Fujian Yuan Liu activated carbon Co., ltd., model YL-303.
Preferably, the tensile strength of the carbon fiber is 3500-4500MPa; further preferably, 4020MPa.
In some preferred embodiments, the carbon fibers are purchased from eastern carbon fiber (guangdong) limited under model M55JB.
Preferably, the weight ratio of the carbon material to the ethanol aqueous solution is 1: (15-35).
Preferably, the concentration of ethanol in the ethanol aqueous solution is 95wt%.
Preferably, the first solution is a mixed solution of magnesium chloride and a chelating agent, and the solvent is an ethanol water mixed solution.
Preferably, the molar ratio of the magnesium chloride to the chelating agent is 1: (0.5-2).
Preferably, in the ethanol-water mixture, the concentration of ethanol is 99.5wt%.
Preferably, the chelating agent comprises one or more of acetylacetone, tartaric acid, hydroxyethylidene diphosphonic acid and citric acid.
Preferably, the dosage of the ethanol water mixture is 3-6 times of the total mass of the magnesium chloride and the chelating agent.
Preferably, the preparation method of the solution I comprises the following steps: adding magnesium chloride and chelating agent into ethanol water mixture, heating to 60deg.C, stirring, and chelating for 2-4 hr.
Preferably, the drop amount of the solution I is 4-8 times of the weight of the carbon material.
The specific implementation mode of continuously heating and recycling the solvent after heating and stirring in the step S1 is as follows: heating to 60-80deg.C, stirring for 1-3 hr, continuously heating to 80-110deg.C, and recovering ethanol.
The calcining atmosphere of the high-temperature calcination in the step S1 is nitrogen.
The specific parameters of the high-temperature calcination in the step S1 are as follows: the temperature is 350-550 ℃ and the time is 2-3h.
The inventor creatively discovers that the composite material obtained by adsorbing and calcining the solution I obtained by chelating magnesium chloride and a chelating agent and a specific carbon material can efficiently remove trace acetone in acetonitrile. The magnesium oxide and the carrier carbon material obtained by chelating magnesium chloride and a chelating agent and calcining have certain adsorption capacity to acetone at normal temperature, but the adsorption capacity of a single material is limited, so the inventor creatively discovers that magnesium ion chelate chelated by the chelating agent and a specific carbon material are mixed and adsorbed and calcined at a high temperature under a specific condition, magnesium oxide particles can be tightly combined on the surface of the carbon material to form a composite material, and the adsorption capacity of the prepared composite material to acetone can be greatly improved under the synergistic effect of the two components, so that trace acetone in acetonitrile can be removed efficiently, and the purity of acetonitrile is further improved.
The temperature in step S2 is 20-25 ℃.
The pressure in the step S2 is 4-6MPa.
The flow rate in the step S2 is 1-2L/S.
In the industrial acetonitrile in the step S2, the acetonitrile content is 98-99 wt% and the acetone content is 50-100 ppm.
In some preferred embodiments, the industrial acetonitrile is derived from southbound chemistry, inc.
In a second aspect, the invention provides a product prepared by the method for removing acetone in industrial acetonitrile.
The beneficial effects are that:
1. the method utilizes the synergistic adsorption effect of the carbon material and the magnesium oxide on the acetone to efficiently remove trace acetone in the acetonitrile.
2. According to the method for removing the acetone in the industrial acetonitrile, the adsorption can be completed at normal temperature, and the acetone in the industrial acetonitrile can be completely adsorbed by the composite material as much as possible only by adjusting the pressure and the flow rate, so that the energy is saved, and the adsorption efficiency can be improved.
3. The method for removing the acetone in the industrial acetonitrile has simple process flow, is suitable for industrial application and has good application prospect.
Detailed Description
Examples
The raw materials used in the examples are all derived from the preferred manufacturers and models in the specification.
Example 1
Example 1 provides a method for removing acetone from industrial acetonitrile, comprising the following steps:
s1, dispersing 2kg of carbon nanotubes in a 200L reaction kettle filled with 50kg of ethanol water solution, dropwise adding ethanol solution of chelated magnesium chloride and acetylacetone into the reaction kettle, starting reflux, stirring at 60 ℃ for reaction for 1.5h, continuously heating to 80 ℃, after the reaction is finished, completely recovering ethanol solvent in the reaction kettle, and calcining the evaporated material in a tubular heating furnace at 400 ℃ in a nitrogen atmosphere for 2h to obtain a magnesium oxide/carbon nanotube composite material;
s2, filling the prepared magnesium oxide/carbon nano tube into an adsorption tower with the size of 0.6mX3m, and introducing industrial acetonitrile into the adsorption tower filled with the magnesium oxide/carbon nano tube composite material at the flow rate of 1.6L/S in the gravity direction by a pump at the temperature of 25 ℃ and the pressure of 4MPa, wherein the acetone content in the acetonitrile product after adsorption is 20ppm.
The concentration of ethanol in the ethanol aqueous solution is 95wt%.
The preparation method of the ethanol solution of the chelated magnesium chloride and the acetylacetone for 2 hours comprises the following steps: adding magnesium chloride and acetylacetone into ethanol water mixture, heating to 60deg.C, stirring, and chelating for 2 hr.
The molar ratio of the magnesium chloride to the acetylacetone is 1:2; the dosage of the ethanol water mixed solution is 5 times of the total mass of magnesium chloride and acetylacetone.
In the ethanol-water mixed solution, the concentration of ethanol is 99.5 weight percent.
The dropping amount of the ethanol solution of the chelated magnesium chloride and the acetylacetone for 2h is 14.9kg.
Example 2
Example 2 provides a method for removing acetone from industrial acetonitrile, comprising the following steps:
s1, dispersing 2kg of graphene in a 200L reaction kettle filled with 50kg of ethanol water solution, dropwise adding ethanol solution of chelated magnesium chloride and tartaric acid into the reaction kettle, starting reflux, stirring at 70 ℃ for 2h, continuously heating to 100 ℃ after the reaction is finished, completely recovering ethanol solvent in the reaction kettle, and calcining the evaporated material in a tubular heating furnace at 500 ℃ in a nitrogen atmosphere for 2.5h to obtain a magnesium oxide/graphene composite material;
s2, filling the prepared magnesium oxide/graphene into an adsorption tower with the size of 0.6mX3m, and pumping industrial acetonitrile into the adsorption tower filled with the magnesium oxide/graphene composite material at the flow rate of 1.8L/S against the gravity direction at the temperature of 25 ℃ and the pressure of 4MPa, wherein the acetone content in the acetonitrile product after adsorption is 25ppm.
The concentration of ethanol in the ethanol aqueous solution is 95wt%.
The preparation method of the ethanol solution of the chelated magnesium chloride and the tartaric acid comprises the following steps: adding magnesium chloride and tartaric acid into ethanol-water mixture, heating to 60deg.C, stirring, and chelating for 3 hr.
The molar ratio of the magnesium chloride to the tartaric acid is 1:1; the dosage of the ethanol water mixed solution is 5 times of the total mass of magnesium chloride and tartaric acid.
In the ethanol-water mixed solution, the concentration of ethanol is 99.5 weight percent.
The dropping amount of the ethanol solution of the chelated magnesium chloride and the tartaric acid for 3 hours is 12.3kg.
Example 3
Example 3 provides a method for removing acetone from industrial acetonitrile, comprising the steps of:
s1, dispersing 2kg of active carbon in a 200L reaction kettle filled with 50kg of ethanol water solution, dropwise adding ethanol solution of chelated magnesium chloride and hydroxyethylidene diphosphonic acid into the reaction kettle, starting reflux, stirring at 80 ℃ for reaction for 3 hours, continuously heating to 110 ℃ after the reaction is finished, completely recovering ethanol solvent in the reaction kettle, and calcining the evaporated material in a tubular heating furnace at 550 ℃ under a nitrogen atmosphere for 2 hours to obtain a magnesium oxide/active carbon composite material;
s2, filling the prepared magnesium oxide/activated carbon into an adsorption tower with the size of 0.6mX3m, and pumping industrial acetonitrile into the adsorption tower filled with the magnesium oxide/activated carbon composite material at the flow rate of 1.4L/S against the gravity direction at the temperature of 25 ℃ and the pressure of 5MPa, wherein no acetone is detected in the acetonitrile product after adsorption.
The concentration of ethanol in the ethanol aqueous solution is 95wt%.
The preparation method of the ethanol water mixed solution of the chelated magnesium chloride and the hydroxyethylidene diphosphonic acid for 3 hours comprises the following steps: adding magnesium chloride and hydroxyethylidene diphosphonic acid into ethanol water mixed solution, heating to 60 ℃, stirring, and chelating for 3h to obtain the final product.
The molar ratio of the magnesium chloride to the hydroxyethylidene diphosphonic acid is 1:0.5; the dosage of the ethanol water mixed solution is 5 times of the total mass of magnesium chloride and hydroxyethylidene diphosphonic acid.
In the ethanol-water mixed solution, the concentration of ethanol is 99.5 weight percent.
The dropping amount of the ethanol solution of the chelated magnesium chloride and the hydroxyethylidene diphosphonic acid is 10kg.
Example 4
Example 4 provides a method for removing acetone from industrial acetonitrile, comprising the steps of:
s1, dispersing 2kg of carbon fibers in a 200L reaction kettle filled with 50kg of ethanol water solution, dropwise adding ethanol solution of chelated magnesium chloride and citric acid into the reaction kettle for 3.5h, starting reflux, stirring at 80 ℃ for 2h, continuously heating to 110 ℃ after the reaction is finished, completely recovering ethanol solvent in the reaction kettle, and calcining the evaporated material in a tubular heating furnace at 500 ℃ in nitrogen atmosphere for 3h to obtain a magnesium oxide/carbon fiber composite material;
s2, filling the prepared magnesia/carbon fiber into an adsorption tower with the size of 0.6mX3m, and pumping industrial acetonitrile into the adsorption tower filled with the magnesia/carbon fiber composite material at the flow rate of 1.2L/S against the gravity direction at the temperature of 25 ℃ and the pressure of 6MPa, wherein the acetone content in the acetonitrile product after adsorption is 10ppm.
The concentration of ethanol in the ethanol aqueous solution is 95wt%.
The preparation method of the ethanol-water mixed solution of the chelated magnesium chloride and the citric acid for 3.5 hours comprises the following steps: adding magnesium chloride and citric acid into ethanol water mixed solution, heating to 60deg.C, stirring, and chelating for 3.5 hr.
The molar ratio of the magnesium chloride to the citric acid is 1:1; the dosage of the ethanol water mixed solution is 5 times of the total mass of magnesium chloride and citric acid.
In the ethanol-water mixed solution, the concentration of ethanol is 99.5 weight percent.
The dropping amount of the ethanol solution of the chelated magnesium chloride and the citric acid for 3.5 hours is 14.5kg.
Comparative example 1
Comparative example 1 provides a process for removing acetone from industrial acetonitrile comprising the steps of:
2kg of carbon fibers are filled into an adsorption tower with the size of 0.6mX3m, industrial acetonitrile is pumped into the adsorption tower filled with the carbon fibers at the temperature of 25 ℃ and the pressure of 6MPa by a pump at the flow rate of 1.2L/s against the gravity direction, and the acetone content of an acetonitrile product after adsorption is 35ppm.
Comparative example 2
Comparative example 2 provides a process for removing acetone from industrial acetonitrile comprising the steps of:
s1, heating 14.5kg of ethanol solution of chelated magnesium chloride and citric acid for 3.5h to 110 ℃, completely recovering ethanol solvent in a reaction kettle, and calcining the evaporated material in a tubular heating furnace at 500 ℃ in a nitrogen atmosphere for 3h to obtain a magnesium oxide material;
s2, filling the prepared magnesium oxide into an adsorption tower with the size of 0.6mX3m, and pumping industrial acetonitrile into the adsorption tower filled with the magnesium oxide at the temperature of 25 ℃ and the pressure of 6MPa at the flow rate of 1.2L/S against the gravity direction, wherein the acetone content of the acetonitrile product after adsorption is 45ppm.
The concentration of ethanol in the aqueous ethanol solution was 99.5wt%.
The preparation method of the ethanol solution of the chelated magnesium chloride and the citric acid for 3.5 hours comprises the following steps: adding magnesium chloride and citric acid into ethanol water solution, heating to 60deg.C, stirring, and chelating for 3.5 hr.
The molar ratio of the magnesium chloride to the citric acid is 1:1; the dosage of the ethanol aqueous solution is 5 times of the total mass of magnesium chloride and citric acid.

Claims (10)

1. A method for removing acetone from industrial acetonitrile, comprising the steps of:
s1, after uniformly mixing a carbon material and an ethanol aqueous solution, dropwise adding a first solution, heating and stirring, and then continuously heating to recover a solvent to obtain a residual material; calcining the rest materials at high temperature to obtain a composite material;
s2, installing the composite material body prepared in the step S1 into an adsorption tower, setting temperature and pressure, introducing industrial acetonitrile into the adsorption tower by a pump at a certain flow speed in the direction of gravity, and collecting acetonitrile at a liquid outlet at the top of the tower after adsorbing the acetone.
2. The method according to claim 1, wherein the carbon material in step S1 comprises one or more of carbon nanotubes, graphene, activated carbon, and carbon fibers.
3. The method for removing acetone from industrial acetonitrile according to claim 2, wherein the carbon nanotubes have an outer diameter of 5-30nm and a specific surface area of 50-200m 2 /g。
4. The method for removing acetone from industrial acetonitrile according to claim 2, wherein the graphene has a particle size of 10-30 μm and a bulk density of 0.05-0.1g/cm 3 。
5. The method for removing acetone from industrial acetonitrile according to any one of claims 1 to 4, wherein the weight ratio of carbon material to ethanol aqueous solution is 1: (15-35).
6. The method for removing acetone from industrial acetonitrile according to claim 5, wherein the first solution is a mixed solution of magnesium chloride and a chelating agent, and the solvent is an ethanol-water mixed solution.
7. The method for removing acetone from industrial acetonitrile according to claim 6, wherein the molar ratio of magnesium chloride to chelating agent is 1: (0.5-2).
8. A method of removing acetone from industrial acetonitrile according to claim 7, wherein the chelating agent comprises one or more of acetylacetone, tartaric acid, hydroxyethylidene diphosphonic acid, and citric acid.
9. The method for removing acetone from industrial acetonitrile according to claim 1, wherein the calcining atmosphere for high-temperature calcination in step S1 is nitrogen; the specific parameters of the high-temperature calcination in the step S2 are as follows: the temperature is 350-550 ℃ and the time is 2-3h.
10. A product produced by the method of removing acetone from industrial acetonitrile according to any one of claims 1-9.
CN202310042866.8A 2023-01-28 2023-01-28 Method for removing acetone in industrial acetonitrile Pending CN116283662A (en)

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Publication Number Publication Date
CN116283662A true CN116283662A (en) 2023-06-23

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