CN110559806A - Binary eutectic solvent and application thereof - Google Patents

Binary eutectic solvent and application thereof Download PDF

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Publication number
CN110559806A
CN110559806A CN201910834948.XA CN201910834948A CN110559806A CN 110559806 A CN110559806 A CN 110559806A CN 201910834948 A CN201910834948 A CN 201910834948A CN 110559806 A CN110559806 A CN 110559806A
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eutectic solvent
component
binary eutectic
absorption
trapping
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黄宽
李子良
钟富裕
蒋文静
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Nanchang University
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Nanchang University
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/18—Absorbing units; Liquid distributors therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/204—Amines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/30—Ionic liquids and zwitter-ions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/40—Nitrogen compounds
    • B01D2257/406—Ammonia

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Gas Separation By Absorption (AREA)

Abstract

The invention discloses a novel binary eutectic solvent and a method for preparing the same in NH3And (4) application in trapping. The eutectic solvent is composed of A, B two components, wherein, A component is proton type ionic salt, B component is phenolic compound or imide compound. In the eutectic solvent provided by the invention, the component A is a hydrogen bond acceptor, the component B is a hydrogen bond donor, and both the component A, B have certain weak acidity which can be NH3Provides a double active site. The eutectic solvent provided by the invention has NH3Large absorption capacity, high selectivity, good cycle performance and low volatility, and is NH in industrial tail gas3The separation and recovery of the (C) provides an efficient, green and environment-friendly absorbent.

Description

Binary eutectic solvent and application thereof
Technical Field
The invention relates to a novel binary eutectic solvent and the application of the eutectic solvent in NH3The application of trapping and concentration, belonging to the field of green chemical industry.
Background
NH3is a poisonous and harmful alkaline gas, which is a main driver for the formation of most secondary particles in PM2.5 and can react with acid gas (SO) in the atmosphere2、NOx) Secondary aerosol is generated by the reaction, thereby causing serious harm to the ecological environment. On the other hand, NH3Can be used for producing ammonia water, nitrogenous fertilizer, ammonium salt, compound fertilizer, soda ash and the like, thereby being widely applied to the fields of chemical industry, light industry, pharmacy, chemical fertilizer and the like. Therefore, for NH in industrial exhaust gas3The separation and the recycling have very important significance.
NH commonly used in industry3The trapping method is acid washing method, and NH is absorbed by aqueous solution of inorganic acid (such as sulfuric acid, nitric acid, etc.)3And finally concentrated to the corresponding ammonium salt. However, the aqueous solution of inorganic acid used in this method is highly corrosive, highly volatile, and absorbs NH3Difficult to be desorbed and recycled, thereby generating a large amount of waste water. Compared with inorganic acid aqueous solution, the Ionic Liquid (ILs) is a novel green solvent, has the characteristics of wide liquid path, extremely low volatility, designable structure and the like, and recently, NH is generated in the solution3The use of the trapping field has made great progress. However, the high viscosity and high cost of ionic liquids greatly hinder their large-scale industrial application. For this reason, there is an urgent need to develop an absorbent for NH, which is more efficient, has a simple preparation process, and has good regeneration properties3And (4) trapping.
eutectic Solvents (DESs) are another new class of green solvents with similar characteristics to ionic liquids, also known as ionic liquid analogs. But compared with the ionic liquid, the eutectic solvent has simpler synthesis steps and lower cost. The eutectic solvent generally consists of two components, namely a hydrogen bond donor and a hydrogen bond acceptor, wherein the hydrogen bond donor generally comprises polyalcohol, carboxylic acid, amide and the like, and the hydrogen bond acceptor generally comprises quaternary ammonium salt, quaternary phosphonium salt and the like. Currently used for NH against eutectic solvents3The research on trapping is still quite limited, the key being to obtain NH3The eutectic solvent absorbent has large absorption capacity, high selectivity and good reversibility. The invention provides a novel binary eutectic solvent which is constructed by taking a proton type ionic salt as a hydrogen bond acceptor and taking a phenol compound or an imide compound as a hydrogen bond donor, wherein the proton type ionic salt and the phenol compound or the imide compound have certain weak acidity and can be NH3The reversible chemical absorption provides double active sites, thereby realizing the NH in the industrial tail gas3high efficiency of trapping.
Disclosure of Invention
The invention aims to provide a novel binary eutectic solvent, which consists of A, B two components, wherein the component A is a proton type ionic salt, and the component B is a phenolic compound or an imide compound.
The proton type ionic salt is specifically selected from one of ethylamine hydrochloride, triethylamine hydrochloride, imidazole hydrochloride, N, N, N ', N' -tetramethyl ethylenediamine dihydrochloride and N, N, N ', N' -tetramethyl-1, 3-propane diamine dihydrochloride, and the structural formula is as follows:
The phenolic compound or imide compound is specifically selected from one of phenol, resorcinol, phloroglucinol, succinimide, phthalimide and 1, 2-cyclohexane dicarboximide, and the structural formula is as follows:
In the binary eutectic solvent, the component A is a hydrogen bond acceptor, the component B is a hydrogen bond donor, and the molar ratio of the two components A, B is 1: 1 to 7. A, B components are mixed evenly according to a certain proportion to prepare the binary eutectic solvent of the invention.
The binary eutectic solvent can be used for synthesizing NH in tail gas discharged in ammonia industry and urea production process3The principle of the high-efficiency trapping is that A, B two components have certain weak acidity, namely NH3Provides a double active site. The binary eutectic solvent is used for NH3The absorption temperature of the trapping is 25-100 ℃, the absorption pressure is 0.01-5 MPa, the desorption temperature is 75-150 ℃, and the desorption pressure is 0.0001-0.01 MPa.
The invention has the beneficial effects that: the binary eutectic solvent provided by the invention has NH3Large absorption capacity, high selectivity, good cycle performance and low volatility. The binary eutectic solvent has cheap and easily obtained synthetic raw materials, simple preparation process and capability of trapping NH in industry3The method has wide application prospect.
The specific implementation mode is as follows:
The present invention will be further illustrated by the following specific examples, but the present invention is not limited to the following examples.
Example 1
Weighing 1.63g (0.02mol) of ethylamine hydrochloride and 13.18g (0.14mol) of phenol in a flask, and stirring and mixing uniformly at 80 ℃ to prepare the binary eutectic solvent.
Example 2
2.03g (0.01mol) of N, N, N ', N' -tetramethyl-1, 3-propanediamine dihydrochloride and 4.71g (0.05mol) of phenol are weighed in a flask, and stirred and mixed uniformly at the temperature of 80 ℃ to prepare the binary eutectic solvent.
Example 3
Weighing 1.63g (0.02mol) of ethylamine hydrochloride and 15.41g (0.14mol) of resorcinol in a flask, and stirring and mixing uniformly at 80 ℃ to prepare the binary eutectic solvent.
Example 4
2.03g (0.01mol) of N, N, N ', N' -tetramethyl-1, 3-propanediamine dihydrochloride and 5.51g (0.05mol) of resorcinol are weighed into a flask, and are stirred and mixed uniformly at the temperature of 80 ℃ to prepare the binary eutectic solvent.
Example 5
Weighing 1.63g (0.02mol) of ethylamine hydrochloride and 17.66g (0.14mol) of phloroglucinol into a flask, and stirring and mixing uniformly at 80 ℃ to prepare the binary eutectic solvent.
Example 6
2.03g (0.01mol) of N, N, N ', N' -tetramethyl-1, 3-propanediamine dihydrochloride and 6.31g (0.05mol) of phloroglucinol are weighed into a flask and stirred and mixed uniformly at the temperature of 80 ℃ to prepare the binary eutectic solvent.
example 7
Weighing 2.75g (0.02mol) of triethylamine hydrochloride and 3.96g (0.04mol) of succinimide in a flask, and stirring and mixing uniformly at 80 ℃ to prepare the binary eutectic solvent.
Example 8
2.09g (0.02mol) of imidazole hydrochloride and 3.96g (0.04mol) of succinimide are weighed in a flask, and stirred and mixed uniformly at 80 ℃ to prepare the binary eutectic solvent.
Example 9
Weighing 2.75g (0.02mol) of triethylamine hydrochloride and 5.89g (0.04mol) of phthalimide in a flask, and stirring and mixing uniformly at 80 ℃ to prepare the binary eutectic solvent.
Example 10
2.09g (0.02mol) of imidazole hydrochloride and 5.89g (0.04mol) of phthalimide are weighed in a flask, and stirred and mixed uniformly at 80 ℃ to prepare the binary eutectic solvent.
Example 11
weighing 2.75g (0.02mol) of triethylamine hydrochloride and 9.19g (0.06mol) of 1, 2-cyclohexane dicarboximide into a flask, and stirring and mixing uniformly at 80 ℃ to prepare the binary eutectic solvent.
Example 12
2.09g (0.02mol) of imidazole hydrochloride and 9.19g (0.06mol) of 1, 2-cyclohexanedicarboximide are weighed into a flask and stirred and mixed evenly at 80 ℃ to prepare the binary eutectic solvent.
Example 13
3.78g (0.02mol) of N, N, N ', N' -tetramethylethylenediamine dihydrochloride and 7.53g (0.08mol) of phenol are weighed in a flask, and stirred and mixed uniformly at 80 ℃ to prepare the binary eutectic solvent.
Example 14
3.78g (0.02mol) of N, N, N ', N' -tetramethylethylenediamine dihydrochloride and 6.61g (0.06mol) of resorcinol are weighed into a flask and stirred and mixed uniformly at the temperature of 80 ℃ to prepare the binary eutectic solvent.
The density and viscosity of the eutectic solvents prepared in examples 1 to 6 at different temperatures are shown in tables 1 and 2, respectively:
TABLE 1 Density of eutectic solvents prepared in examples 1-6 at different temperatures
TABLE 2 viscosity of eutectic solvents prepared in examples 1 to 6 at different temperatures
10g of the eutectic solvent prepared in example 1, example 2 and example 3 was weighed and placed in an absorption cell, and NH was introduced at 40 ℃ under different pressures3Stirring continuously, and calculating NH by the pressure change in the absorption cell after absorption is balanced3The amount of absorption of (c). The results are shown in Table 3:
TABLE 3 eutectic solvents prepared in examples 1-6 for NH at 40 deg.C and different pressures3Absorption amount of
Weighing 10g of the eutectic solvent prepared in example 1, placing the eutectic solvent in an absorption cell, and introducing NH with different pressures at 25 ℃, 40 ℃, 60 ℃ and 80 DEG3Stirring continuously, and calculating NH by the pressure change in the absorption cell after absorption is balanced3The results are shown in Table 4:
Table 4 eutectic solvents prepared in example 1 were applied to NH at different temperatures and pressures3Absorption amount of
0.01MPa 0.02MPa 0.05MPa 0.1MPa
25℃ 0.086g/g 0.123g/g 0.135g/g 0.171g/g
40℃ 0.045g/g 0.056g/g 0.078g/g 0.101g/g
60℃ 0.046g/g 0.065g/g 0.089g/g 0.111g/g
80℃ 0.022g/g 0.035g/g 0.061g/g 0.082g/g
Example 1, example 2 prepared eutectic solvent to NH at 40 ℃3After the absorption is saturated, the mixture is heated to 80 ℃ and vacuumized to 0.0001MPa for desorptionThe desorption time was 2 h. After regeneration is finished, the eutectic solvent is measured again for NH at 40 ℃ and 0.1MPa3The absorption amount was thus repeated 10 times, and the results are shown in Table 5:
Table 5 eutectic solvents prepared in examples 1 and 2 vs NH3Cyclic absorption capacity of
The above data show that the eutectic solvent provided by the present invention is available for NH3The repeated absorption effect is better.
TABLE 6 eutectic solvents prepared in examples 1 and 2 at 40 deg.C and 0.01MPa vs. NH3/CO2Ideal absorption selectivity of
NH3 CO2 NH3/CO2
Example 1 0.045g/g 0.00009g/g 500
Example 2 0.049g/g 0.00010g/g 490
The above data show that the eutectic solvent provided by the present invention is available for NH3/CO2Has excellent absorption selectivity.

Claims (5)

1. A binary eutectic solvent, characterized in that: the eutectic solvent is composed of A, B, wherein the component A is proton type ionic salt, specifically selected from one of ethylamine hydrochloride, triethylamine hydrochloride, imidazole hydrochloride, N, N, N ', N' -tetramethyl ethylenediamine dihydrochloride and N, N, N ', N' -tetramethyl-1, 3-propane diamine dihydrochloride, and the component B is phenolic compound or imide compound, specifically selected from one of phenol, resorcinol, phloroglucinol, succinimide, phthalimide and 1, 2-cyclohexane dicarboximide.
2. The binary eutectic solvent of claim 1, characterized in that: the molar ratio of A, B two components in the eutectic solvent is 1: 1 to 7.
3. the binary eutectic solvent of claim 1 in NH3And (4) application in trapping.
4. Use according to claim 3, characterized in that: NH (NH)3The absorption temperature is 25-100 ℃ and the absorption pressure is 0.01-5 MPa in the trapping process.
5. Use according to claim 3, characterized in that: NH (NH)3The desorption temperature in the trapping process is 75-150 ℃, and the desorption pressure is 0.0001-0.01 MPa.
CN201910834948.XA 2019-09-05 2019-09-05 Binary eutectic solvent and application thereof Pending CN110559806A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111547740A (en) * 2020-03-24 2020-08-18 福州大学化肥催化剂国家工程研究中心 Synthetic ammonia separation process
CN113115980A (en) * 2021-04-01 2021-07-16 中国烟草总公司郑州烟草研究院 Method for reducing phenol content in waste gas
CN113577990A (en) * 2021-06-24 2021-11-02 盐城师范学院 Method for trapping NO by using polyamine-phenol proton type functionalized ionic liquid
CN114436325A (en) * 2022-02-11 2022-05-06 辽宁大学 Method for preparing inorganic porous material in binary eutectic solvent
CN116043591A (en) * 2022-12-15 2023-05-02 浙江工业大学 Method for separating lignocellulose by adopting phenol eutectic solvent

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CN104774643A (en) * 2015-03-30 2015-07-15 浙江大学 Method for extracting and removing basic nitrides from oil product through nitrogen-free eutectic solvent

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US20090008262A1 (en) * 2007-07-05 2009-01-08 King Saud University New method for the preparation of reactive compositions containing superoxide ion
CN104774643A (en) * 2015-03-30 2015-07-15 浙江大学 Method for extracting and removing basic nitrides from oil product through nitrogen-free eutectic solvent

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111547740A (en) * 2020-03-24 2020-08-18 福州大学化肥催化剂国家工程研究中心 Synthetic ammonia separation process
CN113115980A (en) * 2021-04-01 2021-07-16 中国烟草总公司郑州烟草研究院 Method for reducing phenol content in waste gas
CN113115980B (en) * 2021-04-01 2023-06-30 中国烟草总公司郑州烟草研究院 Method for reducing phenol content in waste gas
CN113577990A (en) * 2021-06-24 2021-11-02 盐城师范学院 Method for trapping NO by using polyamine-phenol proton type functionalized ionic liquid
CN113577990B (en) * 2021-06-24 2023-12-22 盐城师范学院 Method for trapping NO by utilizing polyamine-phenol proton functionalized ionic liquid
CN114436325A (en) * 2022-02-11 2022-05-06 辽宁大学 Method for preparing inorganic porous material in binary eutectic solvent
CN116043591A (en) * 2022-12-15 2023-05-02 浙江工业大学 Method for separating lignocellulose by adopting phenol eutectic solvent

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