CN112691508A - Preparation method of diamine ternary eutectic solvent and efficient SO trapping method thereof2Use of - Google Patents

Preparation method of diamine ternary eutectic solvent and efficient SO trapping method thereof2Use of Download PDF

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CN112691508A
CN112691508A CN202110044319.4A CN202110044319A CN112691508A CN 112691508 A CN112691508 A CN 112691508A CN 202110044319 A CN202110044319 A CN 202110044319A CN 112691508 A CN112691508 A CN 112691508A
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diamine
absorption
eutectic solvent
ternary eutectic
hydrogen bond
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CN112691508B (en
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朱倩
王超
邹义儒
朱文帅
陈志刚
李华明
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Jiangsu 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
    • B01D53/1493—Selection of liquid materials for use as absorbents
    • 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
    • B01D53/1456—Removing acid components
    • B01D53/1481—Removing sulfur dioxide or sulfur trioxide
    • 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
    • B01D2252/50—Combinations of absorbents
    • B01D2252/504—Mixtures of two or more absorbents

Abstract

The invention discloses a preparation method of diamine ternary eutectic solvent and high-efficiency SO trapping method thereof2The use of (1). The invention relates to a diamine ternary eutectic solvent which is applied to SO and is prepared by regulating different amine substances and different proportions thereof in diamine ternary eutectic solvent, and synthesizing different amine substances and diamine ternary eutectic solvents with different proportions through design2Absorption of (2). The diamine provided by diamine substance in diamine ternary eutectic solvent forms hydrogen bond with ethylene glycol, and the hydrogen bond and SO2Form strong charge interaction between the two, thereby realizing SO2The diamine ternary eutectic solvent is used as an absorbent to absorb SO2The gas is absorbed under the pressure of 0-1.5 bar, the absorption temperature is 0-80 ℃, and the absorption time is 1-6 h. After absorption, SO2The desorption is easy, the desorption temperature is 50-100 ℃, and the desorption time is about 2-6 h. And conventional SO trapping2Compared with the method, the highest absorption capacity can reach 0.82g SO2/g DES。

Description

Preparation method of diamine ternary eutectic solvent and efficient SO trapping method thereof2Use of
Technical Field
The invention relates to a preparation method of diamine ternary eutectic solvent and high-efficiency SO trapping method2The method of (1).
Background
SO2Is a colorless, strong, pungent acidic gas, and is also a common atmospheric pollutant, which is mainly derived from the combustion of fossil fuels. When SO is in the air2Too high a concentration of (b) can cause diseases of the respiratory system of the human body, and can also form acid rain to corrode buildings and harm the natural environment.
However, pure SO2Has a great industrial application, for example, as a bleaching agent for cloth and a preservative for foods. And pure SO2The price is relatively high. Therefore, SO in the industrial flue gas is realized2On the one hand, can avoid a large amount of SO2The emission causes air pollution, and on the other hand, the 'changing of waste into valuable' of the flue gas can be realized. The industrial dominant methods of flue gas desulfurization so far mainly include limestone method, gypsum method and ammonia absorption method. However, these conventional absorption methods still have some obvious disadvantages, such as the contamination of the absorbent, the non-recyclability of the absorbent, and the possibility of secondary contamination of the absorbed product, which greatly limits the application. Therefore, a series of safe, effective and renewable absorbents are designed and developed to capture SO with high efficiency2Are very significant. Currently, the common flue gas desulfurization technologies in industry can be classified into three types according to the phase state of the desulfurizing agent: dry desulfurization, semi-dry desulfurization and wet desulfurization, the dominant desulfurization mode in the desulfurization field belongs to the wet desulfurization direction, wet desulfurization is a mature method, and wet desulfurization is also used for a large amount of SO in flue gas2Removal of (2) SO by current wet absorption2The technology mainly comprises an alkali liquor absorption method, an ionic liquid absorption method and a eutectic solvent absorption method. Wherein, the alkali liquor absorption method is the most widely used desulfurization technology in China, and the alkali liquor absorption method sprays alkali liquor on the top of the tower, and then blows flue gas into the bottom of the tower to realize SO in the flue gas2Converting into gypsum and other substances, and removing the gypsum. Although the process is mature at present, the method has the problems of high energy consumption, easy secondary pollution and the like, thereby limiting the development of the technology.
In the past decades, Ionic Liquids (IL) have received much attention due to their high thermal stability, low vapor pressure and wide liquid range. A variety of have been developed for SO2Absorbed IL, conventional IL absorbed SO2The mode of action of (a) is achieved by weak physical action, thereby resulting in relatively low absorption capacity. Despite their advantages over traditional lyes, these IL's still suffer from problems such as expensive starting materials, complicated synthetic procedures, and difficulty in degradation, which limits their large-scale use.
In recent years, as a new class of "green" solvents, eutectic solvents (DES) have potential applications in various fields. The eutectic solvent is a solvent which is composed of two or three components, namely a Hydrogen Bond Acceptor (HBA) and a Hydrogen Bond Donor (HBD) in a certain stoichiometric ratio and is liquid at normal temperature through the action of hydrogen bonds. At present, the eutectic solvent can be synthesized by a simple method such as a heating synthesis method, a vacuum evaporation method and a freeze-drying method. Because of its simple synthesis method, the eutectic solvent can be prepared in large scale at a relatively low cost. At present, the development of eutectic solvent gradually tends to be prepared by utilizing non-toxic and easily biodegradable natural compounds, and the eutectic solvent is expected to be applied to industrial absorption of SO2Instead of the traditional alkali liquor and ionic liquid, the SO in the flue gas is realized2The high-efficiency absorption is realized.
Disclosure of Invention
The invention aims to provide a preparation method of diamine ternary eutectic solvent and high-efficiency SO trapping method2The application of the composition is mainly to design and synthesize different amine substances and diamine ternary eutectic solvents with different proportions, and the composition is applied to SO2Absorption of (2). The diamine provided by diamine substance in diamine ternary eutectic solvent forms hydrogen bond with ethylene glycol, and the hydrogen bond and SO2Form strong charge interaction between the two, thereby realizing SO2High efficiency of trapping.
The invention is realized by the following technical scheme:
a preparation method of diamine ternary eutectic solvent comprises the following steps:
mixing the hydrogen bond donor and the hydrogen bond acceptor according to the proportion, and then uniformly stirring for a certain time under the condition of oil bath to obtain uniform transparent liquid, namely the required diamine ternary eutectic solvent;
further, the hydrogen bond donor is any two of diethylenetriamine, triethylene tetramine, acetamide, ethylenediamine, ethanolamine, diethanolamine, triethanolamine, tetrabutylammonium chloride and tetrabutylammonium bromide; hydrogen bond donor I and hydrogen bond donor II;
further, the hydrogen bond acceptor is any one of ethylene glycol, glycerol, polyethylene glycol-200 and polyethylene glycol-400.
The molar ratio of the hydrogen bond donor I to the hydrogen bond donor II to the hydrogen bond acceptor is (1-2): (1-2): (1-3).
The temperature of the oil bath is 70-100 ℃, and the stirring time is 1-4 h.
The diamine ternary eutectic solvent prepared by the invention is used for efficiently trapping SO2The application of the method comprises the steps of using a double-chamber gas trapping device, placing diamine ternary eutectic solvent in an absorption tank, and placing SO2Placing in a gas storage tank, mixing diamine ternary eutectic solvent and SO2Interaction for efficient SO absorption2The absorption pressure is 0-1.5 bar, the absorption temperature is 0-80 ℃, and the absorption time is 1-6 h. SO trapped by eutectic solvent2The desorption is easy, the desorption temperature is 50-100 ℃, and the desorption time is 2-6 h.
The invention discloses a ternary eutectic solvent for efficiently trapping SO2The method mainly designs and synthesizes different amine substances and diamine ternary eutectic solvents with different proportions for SO2Absorption of (2). The diamine provided by diamine substance in diamine ternary eutectic solvent forms hydrogen bond with ethylene glycol, and the hydrogen bond and SO2Form strong charge interaction between the two, thereby realizing SO2The highest absorption capacity can reach 0.82 g/g.
The invention has the beneficial effects that:
(1) the eutectic solvent prepared by the invention has the advantages of simple synthesis method, low cost, no pollution to the environment and the like.
(2) The method is simple and efficient to operate, and can realize SO at normal temperature and normal pressure2High efficiency of trapping.
(3) The invention can realize the recycling of the diamine eutectic solvent.
Drawings
FIG. 1 shows SO2Infrared spectrogram of ternary eutectic solvent before and after absorption.
FIG. 2 is SO2Nuclear magnetic hydrogen spectrum of the ternary eutectic solvent before and after absorption.
The specific implementation mode is as follows:
the technical solution of the present invention is further illustrated by the following specific examples.
The invention adopts a 'double-chamber' gas trapping device, and an absorption device consists of two stainless steel tanks made of 316L materials. The capacity is 122.300cm3(V1) The larger volume stainless steel tank of (a) is referred to as a gas storage tank. The capacity is 46.187cm3(V2) The smaller volume stainless steel tank is referred to as the absorption tank, which is equipped with a magnetic stirrer. The absorption temperature of the two stainless steel tanks was controlled using a super thermostatic water bath with a precision of + -0.1K. Two pressure sensors with a precision of + -0.2% transfer the pressure from the respective stainless steel tanks to a digital display meter and record on a terminal computer. Before an absorption experiment, a certain mass of eutectic solvent (omega) is placed into an absorption tank, and the two stainless steel tanks are vacuumized for about 2-3 hours. At this time, the pressure in the canister is recorded as P0. Then, SO is added2Introducing into a gas storage tank and recording the pressure as P1. The two tank bodies are connected together through a thin tube with a valve. Adding SO2After introduction from the gas holder into the absorption tank, absorption starts. When the absorption reached equilibrium, the pressure in the absorption tank was recorded as P2Pressure in the gas tank is recorded as P'1. SO in absorption tank2Can be passed through Pso2＝P2-P0And (4) obtaining. At this time, SO2The absorption capacity of (a) is calculated by the following formula:
Figure BDA0002896570870000031
example 1
Weighing 0.1000g of prepared diamine ternary DES (the weight ratio of substances of diethylenetriamine, acetamide and ethylene glycol is 1: 1: 2, and the mixture is stirred for 2 hours under the condition of 80 ℃ oil bath) in an absorption tank, stirring the mixture by using a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing the sealed absorption tank and gas storage tank in a constant-temperature water bath with the accurate temperature control of 25 ℃, filling SO2The maximum absorption capacity was 0.82g/g, and was not changed 2 hours after the absorption reached equilibrium.
Example 2
Weighing 0.1000g of prepared diamine ternary DES (the weight ratio of substances of diethylenetriamine, acetamide and ethylene glycol is 1: 1: 2, and the mixture is stirred for 2 hours under the condition of 70 ℃ oil bath) in an absorption tank, stirring the mixture by using a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing the sealed absorption tank and gas storage tank in a constant-temperature water bath with the accurate temperature control of 25 ℃, filling SO2The maximum absorption capacity was 0.74g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 3
Weighing 0.1000g of prepared diamine ternary DES (the weight ratio of substances of diethylenetriamine, acetamide and ethylene glycol is 1: 1: 2, stirring for 2 hours under the condition of 90 ℃ oil bath) in advance, placing the mixture in an absorption tank, stirring by using a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing the sealed absorption tank and gas storage tank in a constant-temperature water bath with the accurate temperature control of 25 ℃, filling SO2The maximum absorption capacity was 0.71g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 4
Weighing 0.1000g of prepared diamine ternary DES (the weight ratio of substances of diethylenetriamine, acetamide and ethylene glycol is 1: 1: 2, and the mixture is stirred for 1 hour under the condition of 80 ℃ oil bath) in an absorption tank, stirring the mixture by using a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing the sealed absorption tank and gas storage tank in a constant-temperature water bath with the accurate temperature control of 25 ℃, filling SO2The maximum absorption capacity was 0.68g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 5
Weighing 0.1000g of prepared diamine ternary DES (the weight ratio of substances of diethylenetriamine, acetamide and ethylene glycol is 1: 1: 2, and the mixture is stirred for 3 hours under the condition of 80 ℃ oil bath) in an absorption tank, stirring the mixture by using a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing the sealed absorption tank and gas storage tank in a constant-temperature water bath with the accurate temperature control of 25 ℃, filling SO2The maximum absorption capacity was 0.81g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 6
Weighing 0.1000g of prepared diamine ternary DES (the weight ratio of substances of diethylenetriamine, acetamide and ethylene glycol is 1: 1: 1, and the mixture is stirred for 2 hours under the condition of 80 ℃ oil bath) in an absorption tank, stirring the mixture by using a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing the sealed absorption tank and gas storage tank in a constant-temperature water bath with the accurate temperature control of 25 ℃, filling SO2The maximum absorption capacity was 0.65g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 7
Weighing 0.1000g of prepared diamine ternary DES (the weight ratio of substances of diethylenetriamine, acetamide and ethylene glycol is 1: 1: 3, and the mixture is stirred for 2 hours under the condition of 80 ℃ oil bath) in an absorption tank, stirring the mixture by using a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing the sealed absorption tank and gas storage tank in a constant-temperature water bath with the accurate temperature control of 25 ℃, filling SO2The maximum absorption capacity was 0.68g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 8
Weighing 0.1000g of prepared diamine ternary DES (the weight ratio of substances of diethylenetriamine, acetamide and ethylene glycol is 1: 2: 2, and the mixture is stirred for 2 hours under the condition of 80 ℃ oil bath) in an absorption tank, stirring the mixture by using a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing the sealed absorption tank and gas storage tank in a constant-temperature water bath with the accurate temperature control of 25 ℃, filling SO2The maximum absorption capacity was 0.66g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 9
Weighing 0.1000g of prepared diamine ternary DES (diethylenetriamine, acetamide and ethylene glycol in a ratio of 1: 1: 2), and oil-bathing at 80 deg.CStirring for 2 hours under the condition) is placed in an absorption tank and stirred by a magnetic stirrer, the absorption tank and a gas storage tank are sealed and then placed in a constant temperature water bath with the temperature accurately controlled at 40 ℃, SO is filled in the constant temperature water bath2The maximum absorption capacity was 0.68g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 10
Weighing 0.1000g of prepared diamine ternary DES (synthesized by stirring for 2 hours under the condition of 80 ℃ oil bath) in an absorption tank, stirring with a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing in a constant temperature water bath with accurate temperature control of 40 ℃, charging SO2The maximum absorption capacity was 0.65g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 11
Weighing 0.1000g of prepared diamine ternary DES (synthesized by stirring triethylene tetramine, acetamide and ethylene glycol at a ratio of 1: 1: 2 for 2 hours under the condition of 80 ℃ oil bath), placing in an absorption tank, stirring with a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing in a constant-temperature water bath with accurate temperature control of 25 ℃, filling SO2The maximum absorption capacity was 0.58g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 12
Weighing 0.1000g of prepared diamine ternary DES (diethylene triamine, ethylene diamine and ethylene glycol with the mass ratio of 1: 1: 2, stirring for 2 hours under the condition of 80 ℃ oil bath), placing in an absorption tank, stirring with a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing in a constant-temperature water bath with the temperature accurately controlled at 25 ℃, filling SO2The maximum absorption capacity was 0.61g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 13
Weighing 0.1000g of prepared diamine ternary DES (diethylene triamine, tetrabutylammonium chloride and ethylene glycol with the mass ratio of 1: 1: 2, stirring for 2 hours under the condition of 80 ℃ oil bath), placing in an absorption tank, stirring with a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing in a constant-temperature water bath with the temperature accurately controlled at 25 ℃, and filling SO2The maximum absorption capacity was 0.71g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 14
Weighing 0.1000g of pre-prepared diamine ternary DES (synthesized by stirring acetamide, ethanolamine and ethylene glycol at a ratio of 1: 1: 2 for 2 hours under the condition of 80 ℃ oil bath), placing in an absorption tank, stirring with a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing in a constant temperature water bath with accurate temperature control of 25 ℃, charging SO2The maximum absorption capacity was 0.55g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 15
Weighing 0.1000g of prepared diamine ternary DES (synthesized by stirring for 2 hours under the condition of 80 ℃ oil bath) in an absorption tank, stirring with a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing in a constant temperature water bath with accurate temperature control of 25 ℃, charging SO2The maximum absorption capacity was 0.44g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 16
Weighing 0.1000g of pre-prepared diamine ternary DES (synthesized by stirring acetamide, triethanolamine and ethylene glycol at a ratio of 2: 1: 2 for 2 hours under the condition of 80 ℃ oil bath), placing in an absorption tank, stirring with a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing in a constant temperature water bath with accurate temperature control of 25 ℃, charging SO2The maximum absorption capacity was 0.42g/g, until the absorption became constant 2 hours after the equilibrium was reached.
Example 17
Weighing 0.1000g of prepared diamine ternary DES (synthesized by stirring for 2 hours under the condition of 80 ℃ oil bath) in an absorption tank, stirring with a magnetic stirrer, sealing the absorption tank and a gas storage tank, placing in a constant temperature water bath with accurate temperature control of 25 ℃, charging SO2The maximum absorption capacity was 0.72g/g, and was not changed 2 hours after the absorption reached equilibrium.
Example 18
0.1000g of the pre-prepared bis is weighedAmine ternary DES (synthesized by stirring for 2 hours under the condition of 80 ℃ oil bath according to the mass ratio of diethylenetriamine, acetamide and polyethylene glycol-200 of 1: 1: 2) is placed in an absorption tank and stirred by a magnetic stirrer, the absorption tank and a gas storage tank are sealed and then placed in a constant temperature water bath with the accurate temperature control of 25 ℃, SO is filled in the constant temperature water bath2The maximum absorption capacity was 0.55g/g, until the absorption became constant 2 hours after the equilibrium was reached.
From FIG. 1 and FIG. 2, we can see that the diamine ternary eutectic solvent successfully absorbs SO2And the mode of action is hydrogen bond formed by amino and glycol and SO2Strong electric charge between them.

Claims (6)

1. The preparation method of the diamine ternary eutectic solvent is characterized by comprising the following steps:
mixing the hydrogen bond donor and the hydrogen bond acceptor in proportion, and then uniformly stirring for a period of time under the condition of oil bath to obtain uniform transparent liquid, namely the required diamine ternary eutectic solvent;
the hydrogen bond donor is any two of diethylenetriamine, triethylene tetramine, acetamide, ethylenediamine, ethanolamine, diethanolamine, triethanolamine, tetrabutylammonium chloride and tetrabutylammonium bromide; hydrogen bond donor I and hydrogen bond donor II;
the hydrogen bond acceptor is any one of ethylene glycol, glycerol, polyethylene glycol-200 and polyethylene glycol-400.
2. The method for preparing the diamine ternary eutectic solvent according to claim 1, wherein the molar ratio of the hydrogen bond donor I to the hydrogen bond donor II to the hydrogen bond acceptor is (1-2): (1-2): (1-3).
3. The method for preparing the diamine ternary eutectic solvent according to claim 1, wherein the temperature of the oil bath is 70-100 ℃ and the stirring time is 1-4 h.
4. Diamine ternary oligomer prepared by the preparation method of any one of claims 1 to 3Co-melting solvent for efficiently trapping SO2The use of (1).
5. Use according to claim 4, characterised in that the diamine-based ternary eutectic solvent is placed in an absorption tank, SO, using a "two-chamber" gas capture device2Placing in a gas storage tank, mixing diamine ternary eutectic solvent and SO2When the double-amine ternary eutectic solvent interacts with each other, the absorption pressure is 0-1.5 bar, the absorption temperature is 0-80 ℃, the absorption time is 1-6 h, and the double-amine ternary eutectic solvent is used for treating SO2And (4) trapping.
6. Use according to claim 5, characterized in that SO is trapped2The later eutectic solvent can effectively realize SO2The desorption temperature is 50-100 ℃, and the desorption time is 2-6 h.
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