CN113069889A - Method for trapping toluene by using eutectic solvent - Google Patents
Method for trapping toluene by using eutectic solvent Download PDFInfo
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- CN113069889A CN113069889A CN202110462827.4A CN202110462827A CN113069889A CN 113069889 A CN113069889 A CN 113069889A CN 202110462827 A CN202110462827 A CN 202110462827A CN 113069889 A CN113069889 A CN 113069889A
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title claims abstract description 272
- 239000002904 solvent Substances 0.000 title claims abstract description 57
- 230000005496 eutectics Effects 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 41
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 27
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims abstract description 25
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000126 substance Substances 0.000 claims abstract description 22
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229940040102 levulinic acid Drugs 0.000 claims abstract description 11
- TZYULTYGSBAILI-UHFFFAOYSA-M trimethyl(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC=C TZYULTYGSBAILI-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims abstract description 9
- 235000019743 Choline chloride Nutrition 0.000 claims abstract description 9
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims abstract description 9
- 229960003178 choline chloride Drugs 0.000 claims abstract description 9
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000010521 absorption reaction Methods 0.000 claims description 114
- 239000007789 gas Substances 0.000 claims description 96
- 238000003860 storage Methods 0.000 claims description 37
- 239000012855 volatile organic compound Substances 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000005303 weighing Methods 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 5
- 238000004364 calculation method Methods 0.000 claims description 3
- 239000012159 carrier gas Substances 0.000 claims description 3
- 230000008859 change Effects 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 2
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- -1 organic acid salt Chemical class 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 238000003795 desorption Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002608 ionic liquid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000002250 absorbent Substances 0.000 description 4
- 230000002745 absorbent Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 101100480489 Arabidopsis thaliana TAAC gene Proteins 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 230000009970 fire resistant effect Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 159000000000 sodium salts Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- CVLHGLWXLDOELD-UHFFFAOYSA-N 4-(Propan-2-yl)benzenesulfonic acid Chemical compound CC(C)C1=CC=C(S(O)(=O)=O)C=C1 CVLHGLWXLDOELD-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
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Classifications
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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
- B01D53/1487—Removing organic compounds
-
- 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
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
- B01D2257/708—Volatile organic compounds V.O.C.'s
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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)
- Treating Waste Gases (AREA)
- Gas Separation By Absorption (AREA)
Abstract
The invention provides a method for trapping toluene by using a eutectic solvent, which comprises the following steps: absorbing toluene by using a eutectic solvent, wherein the eutectic solvent comprises a substance A and a substance B, the substance A comprises any one of tetraethylammonium chloride, allyl trimethyl ammonium chloride, choline chloride or triethyl benzyl ammonium chloride, the substance B comprises any one of phenol, ethylene glycol or levulinic acid, and the molar ratio of the substance A to the substance B is 1: 1-1: 4. The method not only effectively recovers the toluene, ensures the safety, but also effectively solves the problem of environmental protection in the treatment of the toluene tail gas.
Description
Technical Field
The invention relates to a toluene tail gas recovery process, in particular to a method for capturing toluene by using a eutectic solvent.
Background
Toluene, as a common Volatile Organic Compound (VOCs), can not only cause harm to human bodies, but also damage the environment in the using process, thereby causing serious environmental pollution. Therefore, there is a need to find a suitable way to reduce the emission of toluene to reduce the losses caused by its emission.
The conventional toluene treatment techniques include an adsorption method, a catalytic oxidation method, a biological treatment method, a plasma technique treatment method, and an absorption method. The absorption method is a traditional and mature treatment process, and is to use the solubility of toluene in certain solvents and use oily solvents with high boiling points and low vapor pressure to absorb and purify toluene-containing tail gas. The absorption method is favored by researchers because of its many advantages, such as low cost, simple operation, and good treatment effect. The selection of the absorbent is a key factor influencing the absorption effect. From the viewpoint of "green chemistry", the ideal absorbent should not only be a compound having a significant absorption capacity and a high selectivity for harmful gases, but also have the property of causing little or no environmental pollution.
CN103143237A discloses a toluene-containing tail gas recovery process in the production of fire-resistant mica tapes, which comprises the following steps: (1) introducing toluene-containing tail gas discharged from a fire-resistant mica tape production device from the bottom of an absorption tower, carrying out gas-liquid countercurrent contact with an absorption liquid of an organic acid salt or inorganic acid ester (salt) aqueous solution sprayed from the top of the absorption tower at 20-70 ℃ and 0.1MPa to finish a toluene absorption process, and discharging the toluene-removed gas from the top of the absorption tower after reaching the standard;
(2) when the absorption rate of toluene tail gas in an absorption tower reaches 75-90%, toluene-containing absorption liquid enters a storage tank, the toluene-containing absorption liquid is heated by a pump through a heater and enters a desorption tower to be desorbed at 90-120 ℃ and 0.1MPa, a toluene-water azeotrope is obtained at the top of the desorption tower, the azeotrope is condensed and enters a layering tank to be layered, the upper layer is rich in toluene, and toluene is obtained after drying;
(3) when the desorption rate of the absorption liquid reaches more than 95 percent, taking out the toluene generated after desorption from the layering tank for production and reuse; and introducing the desorbed absorption liquid into a storage tank from the desorption tower, cooling to 20-50 ℃, and pumping to the absorption tower for recycling. In the patent, inorganic acid salt or inorganic acid ester (salt) aqueous solution is adopted, organic acid is acetic acid, oxalic acid, phthalic acid, terephthalic acid, isophthalic acid, citric acid, naphthoic acid, benzenesulfonic acid, methanesulfonic acid, p-toluenesulfonic acid (meta, para or ortho), xylene sulfonic acid and cumene sulfonic acid, and corresponding organic acid salt is sodium salt, potassium salt and ammonium salt of the organic acid; the inorganic acid is carbonic acid, silicic acid, sulfuric acid, phosphoric acid, and the corresponding inorganic acid ester (salt) is sodium salt, potassium salt, or ammonium salt of the above inorganic acid. The temperature of the desorption tower is between 90 and 120 ℃, a large amount of energy is consumed, particularly, various three wastes generated by the desorption tower need to be further treated, and the waste on the production cost and the maintenance cost is caused to production enterprises invisibly.
Therefore, it is an urgent technical problem to provide a method for treating VOCs (particularly toluene) which is inexpensive, easy to operate, and has a good treatment effect, and which effectively increases the amount of absorption of volatile organic compounds such as toluene.
Disclosure of Invention
The invention provides a method for trapping toluene by using a eutectic solvent. The method not only effectively recovers the toluene, ensures the safety, but also effectively solves the problem of environmental protection in the treatment of the toluene tail gas.
The technical scheme of the invention is as follows:
a method of capturing toluene using a eutectic solvent, the method comprising:
absorbing toluene by using a eutectic solvent, wherein the eutectic solvent comprises a substance A and a substance B, the substance A comprises any one of tetraethylammonium chloride, allyl trimethyl ammonium chloride, choline chloride or triethyl benzyl ammonium chloride, the substance B comprises any one of phenol, ethylene glycol or levulinic acid, and the molar ratio of the substance A to the substance B is 1: 1-1: 4.
Further, the composition of the eutectic solvent is tetraethylammonium chloride/phenol, allyltrimethylammonium chloride/ethylene glycol, allyltrimethylammonium chloride/levulinic acid, choline chloride/phenol, choline chloride/levulinic acid, triethylbenzylammonium chloride/phenol, triethylbenzylammonium chloride/levulinic acid or triethylbenzylammonium chloride/ethylene glycol.
Further, after the method is operated, the absorption amount of toluene absorbed by the eutectic solvent is 10-360mg/g, wherein the calculation formula of the absorption amount is as follows:
the unit of the total content of the sodium hydroxide is mg/g,
wherein the dimension is mg, m0Is the mass m of the absorption bottle1M is the mass of the absorption bottle (7) after the eutectic solvent is added2To complete the mass of the absorption bottle after trapping.
Further, the method is performed in the following system:
the system comprises N connected in sequence2The device comprises a gas storage cylinder, a VOCs gas storage cylinder, a buffer cylinder, an absorption cylinder, a gas chromatograph and a computer; wherein, the N is2The gas storage bottle is divided into two branch pipelines after passing through a pressure reducing valve and a first pipeline switch, one branch pipeline is communicated into the VOCs gas storage tank through a flow regulator and a pressure regulator which are sequentially arranged on the pipeline after passing through a second pipeline switch, and gas discharged from the top of the VOCs gas storage tank enters the buffer bottle from the bottom of the buffer bottle through a pipeline; the other branch pipeline is switched by a third pipeline and then returns to the buffer bottle from the bottom of the buffer bottle after passing through a flow regulator and a pressure regulator which are sequentially arranged on the pipeline;
a pipeline discharged from the top of the buffer bottle is divided into two branch pipelines, wherein one branch pipeline leads gas into the absorption bottle through a fourth pipeline switch, the absorption bottle is arranged in a constant-temperature water bath kettle, and the absorbed gas is discharged from the pipeline at the top of the absorption bottle, enters the gas chromatograph, then transmits the acquired data to a software client on a computer, and reads the data and analyzes the chart; and the other branch pipeline directly enters the gas chromatograph through a fifth pipeline switch and then transmits the acquired data to a software client on a computer for data comparison and analysis.
Further, the method comprises the steps of:
s1: the mass meter for weighing the absorption bottle is m0Filling the eutectic solvent into the absorption bottle, and weighing the absorption bottle after the eutectic solvent is added into the absorption bottle to obtain m1，m1-m0Namely the mass of the eutectic solvent;
s2: said N is2Introducing nitrogen in a gas storage bottle into the VOCs gas storage tank, introducing the nitrogen serving as carrier gas of the gas in the VOCs gas storage tank into the buffer bottle together, setting the total amount of the gas which enters the absorption bottle unchanged, and adding the N2Introducing nitrogen in a gas storage bottle into the buffer bottle to dilute gas in the buffer bottle, so as to adjust the partial pressure of VOCs gas to change the content of VOCs gas in the absorption bottle, wherein the gas in the VOCs gas storage tank is toluene;
s3: after the toluene gas is collected for a period of time, the toluene concentration in the absorption bottle is measured, when the toluene concentration is basically kept unchanged, the absorption saturation is achieved, the trapping is completed, and the mass of the absorption bottle is measured and recorded as m2，m2-m1Namely the quality of the trapped toluene;
and calculating the result of the absorption amount according to the calculation formula of the absorption amount.
Further, the total pressure of all the gases in the buffer bottle is P0The partial pressure of the gas from the VOCs gas storage tank in the buffer bottle is P, and when the third pipeline switch is closed, P/P 01 is ═ 1; when the third pipeline switch is turned on, P/P is more than 0.10＜1。
Further, the absorption temperature in the absorption bottle is 20-45 ℃.
Further, the absorption temperature in the absorption flask was 25 ℃, 30 ℃, 40 ℃.
Further, in the eutectic solvent, the molar ratio of the substance A to the substance B is 1: 2. 1: 2.5, 1: 3. 1: 4.
further, in the eutectic solvent, substance a: the molar value of substance B was 1: at time 3, at P/P0The absorption amount of toluene of the eutectic solvent is up to 257mg/g when the eutectic solvent is 1.
Further, the eutectic solvent is prepared as follows:
adding the substance B into the container, weighing the substance A according to the molar ratio of the substance A to the substance B, adding the substance A into the container, and stirring on a magnetic stirrer until the substance A is in a liquid state. And then, putting the container into a vacuum drying oven for drying, setting the temperature to be 60 ℃, and drying for 6 hours to obtain the eutectic solvent.
The invention has the following technical effects:
1. since the introduction of the concept of "green chemistry", ionic liquids have been increasingly used as absorbents to reduce environmental damage instead of traditional organic substances. The eutectic solvent as an ionic liquid analogue not only has the excellent properties which are comparable to the ionic liquid, such as: low vapor pressure, difficult volatilization, low melting point, strong thermal stability and chemical stability, and also has the advantages of low cost, simple preparation and biodegradability which are not possessed by the ionic liquid. The invention utilizes the advantages of the eutectic solvent to trap the toluene, and produces unexpected technical effects.
2. In all the eutectic solvents for absorbing VOCs (such as toluene) in the invention, when the mixture ratio of the substance A and the substance B is 1:3, the toluene absorption is maximum. Among these eutectic solvents, triethylbenzylammonium chloride/phenol is particularly the best absorption solvent. The p-pi conjugation is generated in the phenol, so that hydrogen bonds are generated between hydroxyl serving as electron donating groups and triethylbenzyl ammonium chloride, and when the content of the phenol is low, pi … pi bonds exist between the phenol and the toluene for toluene absorption besides the absorption of the hydrogen bonds of the eutectic solvent to the toluene; when the mixture ratio of the two is 1:3, the superposition of pi … pi bonds and OH … pi bonds exists between the redundant phenol and the toluene, so that the absorption of the toluene is promoted; when the mixture ratio of the two is 1:4, in addition to the above, a sufficient amount of phenol forms another OH … OH hydrogen bond network inside the phenol, and the formation of such a hydrogen bond network inhibits the combination of phenol with toluene, so that the absorption capacity of toluene is decreased.
Drawings
Fig. 1 is a system/process flow diagram for capturing toluene with a eutectic solvent in the present invention.
FIG. 2 is a graph in which absorption curves at 25 ℃ and 30 ℃ are plotted with eutectic solvents of different compositions as abscissa and absorption as ordinate, respectively, in inventive experiment 1.
FIG. 3 shows P/P in test example 2 of the present invention0The absorption of toluene is plotted on the abscissa and the absorption of toluene is plotted on the ordinate against the absorption of triethylbenzylammonium chloride/phenol at different molar ratios at an absorption temperature of 30 ℃.
FIG. 4 shows P/P in test example 3 of the present invention0The absorption of toluene is plotted on the abscissa and on the ordinate as triethylbenzylammonium chloride/phenol (molar ratio 1:3) at different temperatures.
Reference numerals:
1-N2a gas cylinder;
2-VOCs gas storage tank;
3-a buffer bottle;
4-an absorption bottle;
5-gas chromatography;
6-a computer;
7-constant temperature water bath;
a-1, A-2, A-3, A-4 and A-5 are all pipeline switches.
Detailed Description
The method for capturing toluene of the present invention was carried out using the system shown in figure 1,
as shown in FIG. 1, the system comprises N connected in sequence2The device comprises a gas storage bottle 1, a VOCs gas storage tank 2, a buffer bottle 3, an absorption bottle 4, a gas chromatograph 5, a computer 6 and a constant-temperature water bath 7; wherein, the N is2The gas storage cylinder 1 is divided into two branch pipelines after passing through a pressure reducing valve and a first pipeline switch A-1, and one branch pipeline is communicated with the VOCs gas storage cylinder through a flow regulator and a pressure regulator which are sequentially arranged on the pipeline after passing through a second pipeline switch A-2The tank 2 is used for discharging gas from the top of the VOCs gas storage tank 2 and then feeding the gas into the buffer bottle 3 from the bottom of the buffer bottle 3 through a pipeline; the other branch pipeline passes through a third pipeline switch A-3 and then returns to the buffer bottle 3 from the bottom of the buffer bottle 3 after passing through a flow regulator and a pressure regulator which are sequentially arranged on the pipeline;
a pipeline discharged from the top of the buffer bottle 3 is divided into two branch pipelines, wherein one branch pipeline leads gas into the absorption bottle 4 through a fourth pipeline switch A-4, the absorption bottle 4 is arranged in a constant-temperature water bath 7, the absorbed gas is discharged from the pipeline at the top of the absorption bottle 4 and enters the gas chromatograph 5, and then the acquired data is transmitted to a software client on a computer 6 for data reading and chart analysis; the other branch pipeline directly enters the gas chromatograph 5 through a fifth pipeline switch A-5 and then transmits the acquired data to a software client on a computer 6 for data comparison and analysis.
The method for capturing the toluene by using the eutectic solvent is implemented by using the system of FIG. 1, and comprises the following steps:
s1: the mass meter of the weighing absorption bottle 4 is m0About 2g of the eutectic solvent was charged into a glass absorption bottle 4 having a height of 15cm and a diameter of 15cm, and the mass of the absorption bottle 4 to which the eutectic solvent was added was weighed to be m1，m1-m0The specific mass of the eutectic solvent is obtained;
S2：N2introducing nitrogen in the gas storage bottle 1 into a VOCs gas storage tank 2, introducing the nitrogen serving as carrier gas of the gas in the VOCs gas storage tank 2 into a buffer bottle 3, setting the total amount of the inlet gas into an absorption bottle 4 to be 100ml/min unchanged, and introducing N into the absorption bottle2Introducing nitrogen in the gas storage bottle 1 into the buffer bottle 3 to dilute the gas in the buffer bottle 3, so as to adjust the partial pressure of the VOCs gas to change the content of the VOCs gas entering the absorption bottle 4, wherein the gas in the VOCs gas storage tank 5 is toluene;
further, the total pressure of all the gases in the buffer bottle 3 is P0The partial pressure of the gas from the VOCs gas storage tank 2 in the buffer bottle 6 is P, and when the third pipeline switch A-3 is closed, P/P 01 is ═ 1; when the third pipeline switch is turned on，0.1＜P/P0＜1；
Further, the absorption temperature in the absorption flask 4 was 25 ℃, 30 ℃, 40 ℃.
Further, in the eutectic solvent, the molar ratio of the substances A and B is 1: 2. 1: 2.5, 1: 3. 1: 4.
s3: after the toluene gas is collected for a period of time, the toluene concentration in the absorption bottle 4 is measured, when the toluene concentration is basically kept unchanged, the absorption saturation is achieved, the trapping is completed, and the mass of the absorption bottle 4 is measured and recorded as m2，m2-m1Namely the quality of the trapped toluene;
specifically, when the concentration of toluene outputted to the gas chromatograph is measured, only the switches A-1, A-2 and A-5 are turned on, the indication on the flow regulator on the branch controlled by the switch A-2 is adjusted to a desired value, and the content of toluene which is not absorbed by the low eutectic solvent is measured by the gas chromatograph, so that the total amount of the intake air introduced into the absorption bottle 4 is 100 ml/min.
If the toluene content in the absorption bottle 4 is changed, the switch A-5 is closed, the switch A-4 is opened, the indication number on the flow regulator on the shunt circuit controlled by the switch A-3 is adjusted, and N is added2The nitrogen in the gas storage bottle 1 is introduced into the buffer bottle 3 to dilute the gas in the buffer bottle 3, and the content of the toluene after the toluene is absorbed by the eutectic solvent is measured until the gas is in a stable state within a period of time. Weigh the total mass m of the absorption flask 4 at this time2. The toluene absorption (mg toluene/g absorbent) is calculated as follows:
Test example 1
Eutectic solvents with different compositions are prepared, and the molar ratio of the substance A to the substance B is 1:3 as follows:
triethylbenzylammonium chloride/phenol (abbreviated as TEBAC: Ph)
Tetraethylammonium chloride/phenol (abbreviation TEBAC: Ph)
Allyl trimethyl ammonium chloride/phenol (abbreviation TAAC: Ph)
Choline chloride/phenol (abbreviation ChCl: Ph)
Triethylbenzylammonium chloride/ethylene glycol (TEBAC: EG)
Allyl trimethyl ammonium chloride/ethylene glycol (TAAC: LA)
Choline chloride/levulinic acid (ChCl: LA)
Allyl trimethyl ammonium chloride/levulinic acid (TAAC: EG)
Triethylene glycol (TEG) as a control group
Ionic liquid [ Emin ] [ Tf2N ] as control group
As shown in FIG. 2, absorption curves at 25 ℃ and 30 ℃ were plotted with eutectic solvents of different compositions as abscissa and absorption as ordinate, respectively.
The experimental results show that under the condition of 25 ℃ or 30 ℃, the ratio of triethyl benzyl ammonium chloride-phenol 1:3 the solution has the best absorption effect. The reason is probably that p-pi conjugation is generated in phenol, so that a hydrogen bond is generated between hydroxyl and triethylbenzyl ammonium chloride as an electron donating group, besides a part of hydrogen bond for forming a eutectic solvent absorbs toluene, a pi … pi bond is also present between phenol and toluene for absorbing toluene, and the action of the two is superposed, so that triethylbenzyl ammonium chloride-phenol shows a better absorption effect than other eutectic solvents under the same proportioning condition.
Test example 2
Taking triethylbenzylammonium chloride/phenol as an example, the total flow of gas admitted into the trap bottle was set at 100ml/min, the toluene content was varied by varying the partial pressure of toluene, and the above toluene trapping experiments were performed at a temperature of 30 ℃ by adjusting different molar ratios of triethylbenzylammonium chloride/phenol.
As shown in FIG. 3, in P/P0The absorption of toluene is plotted on the abscissa and the absorption of triethylbenzylammonium chloride/phenol at different molar ratios is plotted on the ordinate.
The experimental results show that the triethyl benzyl ammonium chloride-phenol is prepared in a weight ratio of 1: the solution absorption effect was best at a molar ratio of 3. The p-pi conjugation is generated in the phenol, so that hydrogen bonds are generated between hydroxyl serving as electron donating groups and triethylbenzyl ammonium chloride, and when the content of the phenol is low, pi … pi bonds exist between the phenol and the toluene for toluene absorption besides the absorption of the hydrogen bonds of the eutectic solvent to the toluene; when the mixture ratio of the two is 1:3, the superposition of pi … pi bonds and OH … pi bonds exists between the redundant phenol and the toluene, so that the absorption of the toluene is promoted; when the mixture ratio of the two is 1:4, in addition to the above, a sufficient amount of phenol forms another OH … OH hydrogen bond network inside the phenol, and the formation of such a hydrogen bond network inhibits the combination of phenol with toluene, so that the absorption capacity of toluene is decreased.
Test example 3
Triethylbenzylammonium chloride/phenol (molar ratio 1:3) was used as an example, and the toluene trapping experiment was performed at 25 ℃, 30 ℃ and 40 ℃ by setting the total flow rate of gas introduced into the trap bottle to 100ml/min and changing the toluene content by changing the partial pressure of toluene.
As shown in FIG. 4, in P/P0As the abscissa and the ordinate, the absorption of toluene was plotted as the curves of triethylbenzylammonium chloride/phenol (1: 3) at different temperatures.
The experiment result shows that the higher the temperature is, the poorer the solution absorption effect of the triethyl benzyl ammonium chloride-phenol is.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention in any way, but any modifications or equivalent variations made according to the technical spirit of the present invention are within the scope of the present invention as claimed.
Claims (10)
1. A method for efficiently capturing toluene using a eutectic solvent, the method comprising:
absorbing toluene by using a eutectic solvent, wherein the eutectic solvent comprises a substance A and a substance B, the substance A comprises any one of tetraethylammonium chloride, allyl trimethyl ammonium chloride, choline chloride or triethyl benzyl ammonium chloride, the substance B comprises any one of phenol, ethylene glycol or levulinic acid, and the molar ratio of the substance A to the substance B is 1: 1-1: 4.
2. The method according to claim 1, characterized in that the composition of the eutectic solvent is tetraethylammonium chloride/phenol, allyltrimethylammonium chloride/ethylene glycol, allyltrimethylammonium chloride/levulinic acid, choline chloride/phenol, choline chloride/levulinic acid, triethylbenzylammonium chloride/phenol, triethylbenzylammonium chloride/levulinic acid or triethylbenzylammonium chloride/ethylene glycol.
3. The method according to claim 2, wherein the absorption amount of toluene absorbed by the eutectic solvent after the method is operated is 10-360mg/g, wherein the absorption amount is calculated by the following formula:
the unit of the total content of the sodium hydroxide is mg/g,
wherein the dimension is mg, m0Is the mass m of the absorption bottle (4)1M is the mass of the absorption bottle (4) after the eutectic solvent is added2To complete the mass of the absorption bottle (4) after trapping.
4. A method according to any of claims 1-3, characterized in that the method is carried out in a system of:
the system comprises N connected in sequence2The device comprises a gas storage bottle (1), a VOCs gas storage tank (2), a buffer bottle (3), an absorption bottle (4), a gas chromatograph (5), a computer (6) and a constant-temperature water bath kettle (7); wherein, the N is2The gas storage bottle (1) is divided into two branch pipelines after passing through a pressure reducing valve and a first pipeline switch (A-1), one branch pipeline passes through a second pipeline switch (A-2) and then is introduced into the VOCs gas storage tank (2) through a flow regulator and a pressure regulator which are sequentially arranged on the pipeline, and gas discharged from the top of the VOCs gas storage tank (2) enters the buffer bottle (3) from the bottom of the buffer bottle (3) through a pipeline; the other branch pipeline passes through a third pipeline switch (A-3) and then passes through flow regulators sequentially arranged on the pipelineAnd the pressure regulator returns to the buffer bottle (3) from the bottom of the buffer bottle (3);
a pipeline discharged from the top of the buffer bottle (3) is divided into two branch pipelines, wherein one branch pipeline leads gas into the absorption bottle (4) through a fourth pipeline switch (A-4), the absorption bottle (4) is arranged in a constant-temperature water bath pot (7), and the absorbed gas is discharged from the pipeline at the top of the absorption bottle (4) and enters the gas chromatograph (5), and then the acquired data is transmitted to a software client on a computer (6) for data reading and chart analysis; the other branch pipeline directly enters the gas chromatograph (5) through a fifth pipeline switch (A-5) and then transmits the acquired data to a software client on a computer (6) for data comparison and analysis.
5. The method of claim 4, comprising the steps of:
s1: the mass meter for weighing the absorption bottle (4) is m0Filling the eutectic solvent into the absorption bottle (4), and weighing the absorption bottle (4) with the eutectic solvent added into the absorption bottle to obtain m1，m1-m0Namely the mass of the eutectic solvent;
s2: said N is2Introducing nitrogen in the gas storage bottle (1) into the VOCs gas storage tank (2) for being used as carrier gas of the gas in the VOCs gas storage tank (2) into the buffer bottle (3) together, setting the total amount of the inlet gas into the absorption bottle (4) unchanged, and passing the N through2Introducing nitrogen in a gas storage bottle (1) into the buffer bottle (3) to dilute the gas in the buffer bottle (3), so as to adjust the partial pressure of VOCs gas to change the content of the VOCs gas in the absorption bottle (4), wherein the gas in the VOCs gas storage tank (5) is toluene;
s3: after the toluene gas is collected for a period of time, the toluene concentration in the absorption bottle (4) is measured, when the toluene concentration is basically kept unchanged, the absorption saturation is achieved, the trapping is completed, and the mass of the absorption bottle (4) is measured and recorded as m2，m2-m1Namely the quality of the trapped toluene;
and calculating the result of the absorption amount according to the calculation formula of the absorption amount.
6. A method according to claim 5, characterized in that the total pressure of all gases in the buffer vessel (3) is P0The partial pressure of gas from the VOCs gas storage tank (2) in the buffer bottle (6) is P, and when the third pipeline switch (A-3) is closed, P/P01 is ═ 1; when the third pipeline switch is turned on, P/P is more than 0.10＜1。
7. The method according to claim 6, characterized in that the absorption temperature in the absorption flask (4) is 20-45 ℃.
8. The method according to claim 7, characterized in that the absorption temperature in the absorption flask (4) is 25 ℃, 30 ℃, 40 ℃.
9. The method according to claim 6, wherein the molar ratio of the substance A to the substance B in the eutectic solvent is 1: 2. 1: 2.5, 1: 3. 1: 4.
10. the method according to claim 9, characterized in that in the eutectic solvent, substance a: the molar value of substance B was 1: at time 3, at P/P0The absorption amount of toluene of the eutectic solvent is up to 257mg/g when the eutectic solvent is 1.
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