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WO2011025030A1 - Absorbant pour l'élimination de composés organiques volatils - Google Patents

Absorbant pour l'élimination de composés organiques volatils Download PDF

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Publication number
WO2011025030A1
WO2011025030A1 PCT/JP2010/064805 JP2010064805W WO2011025030A1 WO 2011025030 A1 WO2011025030 A1 WO 2011025030A1 JP 2010064805 W JP2010064805 W JP 2010064805W WO 2011025030 A1 WO2011025030 A1 WO 2011025030A1
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WIPO (PCT)
Prior art keywords
absorbent
volatile organic
voc
organic compound
epoxy
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PCT/JP2010/064805
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English (en)
Japanese (ja)
Inventor
茂夫 藤井
賢美 伏谷
通秀 渡嘉敷
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NEGISHI SEISAKUSHO CO Ltd
Negishiken
NEGISHIKEN CO Ltd
Original Assignee
NEGISHI SEISAKUSHO CO Ltd
Negishiken
NEGISHIKEN CO Ltd
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Priority to JP2011528905A priority Critical patent/JP5641655B2/ja
Publication of WO2011025030A1 publication Critical patent/WO2011025030A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/202—Alcohols or their derivatives
    • B01D2252/2023—Glycols, diols or their derivatives
    • 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
    • B01D2252/205—Other organic compounds not covered by B01D2252/00 - B01D2252/20494
    • 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
    • B01D2257/702—Hydrocarbons
    • B01D2257/7027—Aromatic hydrocarbons
    • 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
    • B01D2257/704—Solvents not covered by groups B01D2257/702 - B01D2257/7027
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2258/00—Sources of waste gases
    • B01D2258/02—Other waste gases
    • B01D2258/0258—Other waste gases from painting equipments or paint drying installations
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters

Definitions

  • the present invention relates to an absorbent for removing volatile organic compounds (hereinafter referred to as “VOC”) in exhaust, a method for purifying exhaust using the VOC absorbent, and a method for recovering VOC and absorbent. More specifically, in particular, aromatic hydrocarbons such as toluene contained in exhaust discharged from printing, painting, textile industry, wood product manufacturing industry, adhesive-related industry, film processing industry, chemical industry factory and laboratory, etc.
  • VOC volatile organic compounds
  • the present invention relates to an absorbent used for absorption recovery of VOC, which includes esters such as acetate, ketones such as methyl ethyl ketone (MEK), and a method for purifying exhaust containing VOC using the absorbent.
  • Volatile VOCs are generally widely used in industry, particularly in the fields of painting and printing, for example, in the field of printing such as gravure printing and offset printing, in the field of coating outer walls of buildings, and in petroleum fields such as gas stations. .
  • VOC evaporates and diffuses in the air and causes odor and photochemical smog.
  • the first combustion method is a method in which exhaust gas is collected by a duct and passed through a catalyst or removed by newly adding fuel to burn VOC.
  • This combustion method has a feature that the exhaust gas removal rate is large, but dioxins may be generated depending on the temperature conditions, and in addition to the fact that a large amount of CO 2 gas is discharged by combustion, there is a running cost. High is considered a drawback. Further, since the apparatus needs to be enlarged and requires a large amount of investment, it is difficult to install the apparatus because of the high cost of processing exhaust gas from a small source. There is also a problem that VOC cannot be collected and reused.
  • a physical adsorption method is particularly widespread, and the exhaust is brought into contact with a solid powder adsorbent, mainly activated carbon and zeolite, and the contained VOC is adsorbed and removed. .
  • VOC can be desorbed and recovered after adsorption, and VOC and the adsorbent can be reused, respectively, and there is an advantage that the recovery rate is high. In addition, there is an advantage in environmental conservation that no CO 2 is emitted.
  • the liquid absorption method is a method in which exhaust is contacted and absorbed with an absorbing solution, and after absorption, is separated and recovered by a method such as distillation. There is a method of contacting the exhaust liquid with the absorbing liquid in a shower-like state or by a method of bubbling exhaust gas into the absorbing liquid.
  • a high boiling point hydrocarbon solvent such as kerosene, a mixture of glycol monoalkyl ether and decene, an aqueous solution or emulsion of other surfactants, and the like are used.
  • Patent Document 1 Japanese Patent Laid-Open No. 52-37585 (Patent Document 1)) has already been proposed. A mixture of esters, silicate esters, phosphate esters and the like and refined mineral oil is described.
  • the esters in VOC react with the moisture in the air and the dissolved moisture when an ester absorbent is used to release acid free and remain in the absorbing solution.
  • the hydrolysis is further promoted by its acid catalysis, but there is no suggestion in Patent Document 1 regarding this problem, and the absorbing solution absorbs the liberated acid.
  • an alkali deoxidation step and a water treatment step including a salt generated during the deoxidation are further required.
  • an object of the present invention is an absorbent for absorbing and removing VOC contained in exhaust gas, and exhibits a high removal rate regardless of the type of VOC component. Further, in the absorption process, the present invention provides a liquid absorbent capable of simultaneously removing acid liberated by contact of esters with air, a method for purifying exhaust containing VOC using the absorbent, and a method for recovering VOC and absorbent. .
  • the inventors of the present invention have identified a specific from the mutual dissolution relationship between each component of the VOC and the absorbent component that the inventors have focused on. It has been found that the acid liberated by the absorption of VOC along with the absorption of VOC can be solved, and that the above problems can be solved, and the present invention has been completed based on these findings.
  • an absorbent for removing a volatile organic compound in exhaust gas wherein the absorbent contains an epoxy compound.
  • the component further blended with the epoxy compound is at least one medium selected from the group consisting of an ester other than the epoxidized ester, a polyether, a mineral oil-based or synthetic oil-based lubricating oil fraction, and a poly ⁇ -olefin.
  • An absorbent for removing a volatile organic compound according to any one of claims 1 to 8 is provided.
  • a method for recovering a volatile organic compound and an absorbent comprising: separating an sorbent containing the volatile organic compound obtained in the absorption step into a distillation and separating the volatile organic compound into an absorbent.
  • the absorbent for removing VOC in exhaust according to claim 1 it is possible to provide an absorbent capable of absorbing low concentration VOC in exhaust exhausted in large quantities such as printing and painting with a high removal rate. it can.
  • the acid liberated by hydrolysis of the ester contained in the absorbed VOC can be removed simultaneously during the absorption process.
  • the absorption rate is further improved, and the acid removal in the absorption process is facilitated, and separation from VOC in the distillation treatment by specifying a high molecular weight material. Becomes easy.
  • the recovery method according to claims 11 and 12 can also absorb the VOC, remove the acid, and recover and reuse the VOC and the absorbent by utilizing the characteristics of the epoxy compound according to the present invention.
  • the VOC to be subjected to the absorption treatment is not particularly limited, and any treatment can be performed.
  • esters that liberate an acid by hydrolysis can be treated without any problem. can do.
  • VOC-containing exhaust gas applicable to the VOC removal absorbent according to the present invention includes aromatic hydrocarbons such as toluene, amides such as dimethylformamide, heterocyclic compounds such as N-methylpyrrolidone, ketones such as methyl ethyl ketone, It contains one or more alcohols such as isopropyl alcohol and esters such as ethyl acetate.
  • Such a VOC-containing exhaust gas is an exhaust gas generated from a manufacturing process in various industries as described above, and specifically includes VOC in a wide range of 10 to 5000 ppm.
  • exhaust that is generated in large quantities in various fields such as printing, painting, and fiber and that contains a relatively low concentration of VOC is suitable for exerting the effect of the absorbent according to the present invention.
  • the absorbent for removing VOC in exhaust gas according to the present invention contains an epoxy compound and may be solid, that is, granular, but is normally liquid.
  • the epoxy compound is an organic compound having an epoxy group in the molecule, and the epoxy compound suitable as an absorbent for removing VOC in exhaust gas according to the present invention has a molecular weight of 250 or more, more preferably 300 or more. And a boiling point of 200 ° C. or higher.
  • the epoxy compound having such properties has the ability to absorb the used gaseous VOC contained in the exhaust gas, and can remove the acid contained in the absorbed VOC in the absorption process.
  • suitable epoxy compounds are those selected from the group consisting of compounds represented by the following general formulas 1 to 11, and may be one or a mixture of two or more. 1.
  • Alicyclic epoxy type is one or a mixture of two or more.
  • R is a saturated or unsaturated linear or branched alkyl group having 11 to 18 carbon atoms, COOR 1 or
  • R 1 is a linear or branched alkyl group having 4 to 13 carbon atoms, and n is an integer of 1 or 2.
  • R is a linear or branched alkylene group having 1 to 4 carbon atoms, —COOCH 2 —, —CH 2 OOC (CH 2 ) n COOCH 2 —, and n is an integer of 4 to 8. is there. 2.
  • Alcohol type
  • R is a linear or branched alkyl group having 12 to 18 carbon atoms or a phenylalkyl group.
  • R is a linear alkylene group having 2 to 8 carbon atoms, neopentyl group, hydrogenated bisphenol A, or cyclohexanedimethyl group.
  • R and R ′ are each a hydrogen atom or a methyl group, and n is an integer of 1-20.
  • R is a linear alkylene group having 2 to 10 carbon atoms
  • R ′ is a hydrogen atom or a methyl group
  • n + m is an integer of 2 to 6.
  • R is a linear or branched alkyl group having 8 to 18 carbon atoms.
  • R ′ is a linear or branched alkylene group. 4). Ester type
  • R is an alkyl group having 11 to 17 carbon atoms, an alkylphenyl group, a phenylalkyl group, or an alkylcyclohexyl group.
  • R is a linear or branched alkylene group having 4 to 8 carbon atoms, a cyclohexyl group, or a phenyl group. 5.
  • R and R 1 are a hydrogen atom, a linear or branched alkyl group, or an alkyl ester group, and R + R 1 has 16 to 36 carbon atoms.
  • the epoxy group is present in the alicyclic structure, and the chain of the alkyl group R so that the molecular weight is 250 or more. The one whose length is controlled is used.
  • epoxy compounds belonging to the general formulas 1 and 2 include dibutyl epoxyhexahydrophthalate, dipentyl epoxyhexahydrophthalate, dihexyl epoxyhexahydrophthalate, diheptylepoxyhexahydrophthalate, epoxyhexahydrophthalic acid-di Examples include -2-ethylhexyl (EPS), epoxyhexahydrophthalic acid-di-n-octyl, epoxyhexahydrophthalic acid-di-epoxidized stearyl, epoxyhexahydrophthalic acid diisodecyl, etc., but removal rate against VOC From the above viewpoint, epoxyhexahydrophthalic acid-di-2-ethylhexyl (EPS) and epoxyhexahydrophthalic acid-di-n-octyl are preferable.
  • EPS -2-ethylhexyl
  • EPS epoxyhexahydrophthalic acid-di-2-eth
  • Such an epoxy compound preferably has a molecular weight of 250 or more and a boiling point of 200 ° C. or more.
  • the epoxy compounds belonging to the alcohol type are represented by general formulas 4 to 6, and specific examples include ethylene glycol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, and 1.4-cyclohexanedimethanol diglycidyl ether. And propylene glycol diglycidyl ether, butylene glycol diglycidyl ether, hexylene glycol diglycidyl ether, and decamethylene glycol diglycidyl ether.
  • the epoxy compound belonging to the phenol type is a compound represented by the general formulas 7 and 8, and specific examples include bisphenol A diglycidyl ether, methylene diphenol diglycidyl ether, ethylene diphenol diglycidyl ether, and the like. Can do.
  • epoxy compounds represented by the general formulas 9 and 10 belonging to the ester type include glycidyl benzoate, glycidyl toluate, glycidyl ether xylenol, diglycidyl phthalate, and diglycidyl hexahydrophthalate. , Adipic acid diglycidyl ether, sebacic acid diglycidyl ether, decanedicarboxylic acid diglycidyl ether, and the like.
  • epoxy compound represented by the general formula 11 belonging to the alkyl type examples include octyl epoxy stearate, butyl epoxy stearate, epoxy stearyl epoxy stearate, epoxy hexadecyl, epoxy stearyl octylate and the like. .
  • the alicyclic epoxy type compound is excellent in VOC solubility in exhaust VOC absorption treatment, free acid removal is possible, and VOC and absorbent recovery processing are suitable in that they have a molecular weight and boiling point suitable for distillation separation and are stable against hydrolysis, and are preferably epoxyhexahydrophthalic acid diesters such as epoxyisohydrophthalic acid diisodecyl, Preferred are di-2-ethylhexyl hexahydrophthalate and di-n-octyl epoxyhexahydrophthalate.
  • These alcohol-type compounds are also excellent in VOC solubility in exhaust VOC absorption treatment, free acid removal is possible, and suitable for distillation separation in VOC and absorbent recovery treatment. It is suitable in that it has a molecular weight and a boiling point and is stable to hydrolysis, and is a diglycidyl ether (BPO) of a polyether having a liquid bisphenol A skeleton, for example,
  • HBE hydrogenated bisphenol A diglycidyl ether
  • the absorbent according to the present invention may be a mixture of an epoxy compound and a medium.
  • the medium has a solubilizing action with respect to the epoxy compound, and has an action of making solid and liquid epoxy compounds into solution.
  • organic acid esters such as polyethers and liquid hydrocarbons are preferable.
  • the ester include phthalic acid ester and aliphatic dibasic acid ester.
  • phthalic acid esters include, but are not limited to, dibutyl phthalate, dipentyl phthalate, dihexyl phthalate, diheptyl phthalate, di-2-ethylhexyl phthalate, dioctyl phthalate, diisononyl phthalate, and diisodecyl phthalate. Can do.
  • Examples of the aliphatic dibasic acid ester include esters of dibasic acid such as adipic acid, azelaic acid, and sebacic acid, such as di-2-ethylhexyl adipate, diisononyl adipate, diisodecyl adipate, di-azelainate Examples thereof include 2-ethylhexyl, di-2-ethylhexyl sebacate and the like, and those usually used can be appropriately selected.
  • polyalkylene glycol can be used as the polyether.
  • the polyalkylene glycol one having an average molecular weight of 300 to 15,000, preferably 500 to 2,000 can be selected.
  • polypropylene glycol (PPG) or polyethylene having an average molecular weight within the above range can be selected.
  • a glycol (PEG) etc. can be mentioned.
  • liquid hydrocarbons include mineral oil-based lubricating oil fractions, for example, straight-run oils having a kinematic viscosity at 100 ° C. of 3 to 80 mm 2 / s, preferably 2 to 30 mm 2 / s, more preferably 3 to 10 mm 2 / s. systems distillate or cracked oil-based fraction or mixed oil-based fractions thereof, liquid paraffin, the lubricating oil fraction 100 ° C. kinematic viscosity equivalent 20 ⁇ 80mm 2 / s, preferably 3 ⁇ 30mm 2 / s And ⁇ -olefin oligomer (PAO) having an average molecular weight of 300 to 3,000 or the like.
  • mineral oil-based lubricating oil fractions for example, straight-run oils having a kinematic viscosity at 100 ° C. of 3 to 80 mm 2 / s, preferably 2 to 30 mm 2 / s, more preferably 3 to 10 mm 2 / s.
  • Such media can be used singly or in combination of two or more.
  • plastic plasticizers can be used.
  • the absorbent according to the present invention contains an epoxy compound as an essential component, and may contain any effective amount.
  • the epoxy compound is preferably 5% or more, more preferably 10% or more, and particularly preferably 50% or more. Of course, 100% may be used, but it may be absorbed depending on the type of VOC and the concentration in the exhaust gas.
  • the content of the epoxy compound in the agent can be adjusted as appropriate.
  • the mixing ratio may be appropriately determined from the viewpoint of compatibility with the absorbent, etc., but in the case of two types, for example, when PPG and PEG are mixed, It can be used in a ratio of 90:10 to 10:90, preferably 70:30 to 30:70.
  • the above medium has a synergistic effect not only in the dissolution action of the epoxy compound but also in the VOC removal rate.
  • the absorbent comprising the epoxy compound according to the present invention not only has the ability to absorb the used VOC contained in the exhaust gas, but can also remove the acid contained in the absorbed VOC during the absorption process.
  • the ester compound in the VOC component may generate an acid by hydrolysis.
  • a regenerated VOC neutralization step is usually required in addition to the VOC absorption step.
  • the process of the water containing the salt after a neutralization process is also needed.
  • the absorbent comprising the epoxy compound according to the present invention can be used not only as an absorbing solution for exhaust VOC, but also can be removed simultaneously by reacting with an acid, as exemplified by the following reaction with acetic acid. Absorption and acid removal can be processed in a single step.
  • the absorbent When the absorbent is used repeatedly, it deteriorates due to the reaction with the above-mentioned acid, but since the deteriorated absorbent can be discarded by combustion, a special treatment step is unnecessary.
  • the exhaust gas purification method In the exhaust gas purification method according to the present invention, low-concentration VOCs contained in a large amount of exhaust gas are absorbed and removed, and the VOC-containing exhaust gas is passed through an absorption tower filled with a liquid absorbent. An absorption process for dissolving and absorbing VOC in the liquid absorbent is employed. In the absorption process, the VOC-containing exhaust gas and the absorbent may be contacted by any method capable of gas-liquid contact. However, a bubbling method or an absorption tower in which the VOC exhaust gas is finely passed through the absorbent from the bottom of the absorption tower. It is convenient to carry out by a shower method in which the absorbent is sprayed from the top.
  • the processing air volume of the VOC-containing exhaust gas is preferably in the range of 0.5 to 200 m 3 / min, preferably in the range of 100 m 3 / min or less, and if it does not reach 0.5 m 3 / min, a large amount of waste should be processed. However, there is no practical value. On the other hand, if it exceeds 200 m 3 / min, the absorbent is scattered, and the absorption of VOC becomes insufficient, causing the problem that VOC is diffused into the atmosphere. .
  • the temperature of the absorption treatment may be the ambient temperature.
  • an obstacle effective for gas-liquid contact may be present in the absorption tower.
  • An absorption process comprising absorbing the VOC in the absorbent by bringing the exhaust VOC into contact with the absorbent, and 2) subjecting the VOC-containing absorbent obtained in the absorption process to a distillation treatment,
  • a method for recovering exhaust VOC and absorbent comprising a separation step comprising separating VOC and absorbent is provided.
  • the absorption step is based on gas-liquid contact between the exhaust VOC and the absorbent, and a bubbling method and a shower method can be adopted as described above.
  • the absorbent that has absorbed the exhaust VOC can be subjected to a distillation treatment at a predetermined temperature determined by the type of the VOC component, thereby obtaining VOC as a distillate component and an absorbent as a residue component.
  • the VOC obtained by distillation can be reused as it is, and the absorbent can be recycled and used.
  • An absorption tower may be installed in the absorption process, and a distillation tower may be installed in the separation process.
  • the absorption tower is as described above, and the distillation tower may be provided with a number of stages so that the VOC and the absorbent can be separated.
  • the absorption rate is obtained from the difference in VOC concentration between the container (2) inlet and the container (4) outlet.
  • a simple speed measurement VOC sensor (combination of a polymer thin film element and an interference enhanced reflection method) manufactured by Violet Co., Ltd. is used.
  • Acid absorption test by test tube method Take 10 ml of absorbent in a test tube, add a predetermined amount of acetic acid and continue stirring. The acetic acid concentration in the air above the liquid level is measured using a VOC sensor at regular intervals.
  • Types of absorbents In Examples and the like, the following absorbents and media were used.
  • Epoxyhexahydrophthalic acid-di-2-ethylhexyl (2) Hydroxylated bisphenol A diglycidyl ether (HBE) (3) Bisphenol A polyether diglycidyl ether (BPO) (4) Polypropylene glycol (PPG) average molecular weight: 700 (5) Polyethylene glycol (PEG) Average molecular weight: 700 (6) Liquid paraffin (7) Di-2-ethylhexyl phthalate (DOP)
  • EPS Epoxyhexahydrophthalic acid di-2-ethylhexyl (referred to as “EPS”, hereinafter the same) (molecular weight; 410, boiling point;> 250 ° C.) as an absorbent, and methyl ethyl ketone (hereinafter referred to as “MEK”) as VOC.
  • the VOC absorption capacity of the absorbent was measured by the VOC absorption capacity test method. Table 1 shows the absorption rate as an evaluation result.
  • Example 2 Except that ethyl acetate was used in place of MEK as VOC, the same absorbent was used for the VOC absorbency test under the same method and conditions as in Example 1. Table 1 shows the absorption rate as an evaluation result.
  • Example 3 Except for using toluene instead of MEK as VOC, the same absorbent was subjected to the VOC absorbency test by the same method and conditions as in Example 1. Table 1 shows the absorption rate as an evaluation result.
  • Example 4 Except that methanol was used instead of MEK as VOC, the same absorbent was subjected to the VOC absorbency test by the same method and conditions as in Example 1. Table 1 shows the absorption rate as an evaluation result.
  • Example 5 Except that tetrahydrofuran (hereinafter referred to as “THF”) was used as VOC instead of MEK, the same absorbent was subjected to the VOC absorbency test under the same method and conditions as in Example 1. .
  • Table 1 shows the absorption rate as an evaluation result.
  • Example 6 Except that acrylic acid was used as the VOC, the same absorbent was subjected to the VOC absorbency test by the same method and conditions as the absorption method and absorption conditions of Example 1. Table 1 shows the absorption rate as an evaluation result.
  • Example 7 Except for using ethyl acrylate as the VOC, the same absorbent was subjected to the VOC absorbency test by the same method and conditions as the absorption method and absorption conditions of Example 1. Table 1 shows the absorption rate as an evaluation result.
  • Example 8 Except for using butyl acrylate as the VOC, the same absorbent was used for the VOC absorbency test in the same manner and under the same absorption method and absorption conditions as in Example 1. Table 1 shows the absorption rate as an evaluation result.
  • Example 9 Except that 2-ethylhexyl acrylate was used as the VOC, the same absorbent was used in the VOC absorbency test by the same method and conditions as in Example 1. Table 1 shows the absorption rate as an evaluation result.
  • Example 10 Except for using N-methylpyrrolidone as the VOC, the same absorbent was used in the VOC absorbency test by the same method and conditions as in Example 1. Table 1 shows the absorption rate as an evaluation result.
  • Comparative Example 2 The VOC absorbability test was performed in the same method and conditions as in Comparative Example 1 except that ethyl acetate was used instead of MEK as VOC. The evaluation results are shown in Table 1 as absorption rates.
  • Comparative Example 3 The VOC absorbability test was performed by the same method and conditions as in Comparative Example 1 except that toluene was used in place of MEK as VOC. The evaluation results are shown in Table 1 as absorption rates. Comparative Example 4 A VOC absorbency test was performed in the same manner and under the same conditions as in Comparative Example 1 except that ethyl acetate was used as VOC, and an equal volume mixture of polypropylene glycol (PPG) and polyethylene glycol (PEG) was used as the absorbent. The evaluation results are shown in Table 1.
  • PPG polypropylene glycol
  • PEG polyethylene glycol
  • Examples 15-17 EPS was taken as 10 ml of absorbent in a test tube, and a predetermined amount of acetic acid was added thereto and stirring was continued. As shown in Table 2, the concentration of acetic acid in the air on the liquid surface was measured with a sensor at regular intervals. The measurement results are shown in Table 2.
  • Examples 18-21 As the absorbent, (A) bisphenol A diglycidyl ether, (B) epoxypropylphenyl ether, (C) ethylene glycol diglycidyl ether, and (D) hydrogenated bisphenol A diglycidyl ether in the proportions shown in Table 2, respectively.
  • a mixed absorbent mixed with -2-ethylhexyl was prepared and subjected to an acid absorption test of an epoxy compound by the test tube method in the same manner as in Examples 11-13. The measurement results are shown in Table 2.
  • Examples 26-29 Using the absorbent shown in Table 2, the acid absorbability of acetic acid was evaluated.
  • As absorbent a mixture of EPS 20%, PPG 40% and PEG 40% (Example 26), HBE 20%, PPG 40% and PEG 40% mixture (Example 27), BPO 20%, PPG 40% and PEG 4% mixture (Example 28) ), A mixture of 20% HBE and 80% liquid paraffin (Example 29), respectively.
  • PPG and PEG having an average molecular weight of 700 were used.
  • Comparative Example 7 A mixed solution of PPG 50% and PEG 50% was used as the absorbent, and the acid absorption capacity of acetic acid was evaluated under the conditions shown in Table 2.
  • the di-2-ethylhexyl phthalate (DOP) of Comparative Examples 5 and 6 and the polypropylene glycol / polypropylene glycol mixture of Comparative Example 7 show that the concentration of acetic acid on the liquid surface increases with time. Although there was no tendency to decrease, the acid neutralization effect was not exhibited, but the epoxy compounds of Examples 15 to 17 and Examples 22 to 25 and the epoxy compound-containing compositions of Examples 18 to 21 and Examples 26 to 29 were used. According to this, the concentration of acetic acid on the liquid surface decreased with time, and the effect of acid removal of the composition was shown, and a markedly significant acid neutralization effect was obtained.
  • DOP di-2-ethylhexyl phthalate
  • Example 30 The change over time in the absorption capacity of VOC when MEK and ethyl acetate were used as the VOC and EPS was used as the absorbent was measured by the VOC absorption capacity test apparatus using the bubbling method. Table 3 shows the measurement results.
  • Example 31 Using a VOC absorber designed in common with the VOC absorbency test device described above, continuous operation was performed to evaluate the durability of the VOC absorbency of the absorbent.
  • Air is introduced from the air blower at an air volume of 30 m 3 / min into the VOC 300 ml inlet chamber (volume 4 m 3 ), passed through the absorbent 200 L in the absorption tank (volume 5 m 3 ), and VOC via the outlet chamber (volume 100 L). The air was removed. The VOC concentration was measured at measuring points 1 (in the piping between the inlet chamber and the absorption tank) and 2 (in the outlet piping of the outlet chamber). The evaluation results are shown in Table 4.
  • the present invention provides an absorbent that absorbs and removes VOC in exhaust gas, a method for purifying exhaust gas using the absorbent, and a method for recovering VOC and absorbent.
  • the present invention eliminates VOC in a wide range of industrial fields that handle VOC. As a method, the utility value is great, and the applicability is extremely great from the viewpoint of environmental conservation.

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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)
  • Treating Waste Gases (AREA)

Abstract

L'invention vise à proposer un absorbant liquide pour une élimination de composés organiques volatils qui a un rapport d'absorption élevé des composés organiques volatils (COV) dans un échappement et est capable d'éliminer simultanément des acides isolés par hydrolyse d'esters dans les COV, et de fournir un procédé de purification pour des COV dans un échappement à l'aide dudit absorbant. L'invention porte également sur un absorbant qui comprend un composé époxy et est liquide dans un état normal, sur un procédé de purification pour un échappement contenant des COV à l'aide dudit absorbant, et sur un procédé de récupération pour les COV et l'absorbant. Le composé époxy est un composé organique qui a un groupe époxy dans chaque molécule, et le composé époxy qui est optimal comme absorbant pour éliminer les COV dans l'échappement a une masse moléculaire d'au moins 250 et un point d'ébullition d'au moins 200°C. L'absorbant comprenant le composé époxy est capable d'absorber simultanément les COV et d'éliminer les acides isolés.
PCT/JP2010/064805 2009-08-31 2010-08-31 Absorbant pour l'élimination de composés organiques volatils Ceased WO2011025030A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3320963A1 (fr) * 2016-11-15 2018-05-16 Basf Se Procédé pour enlever un hydrocarbure aromatique d'un flux de gaz
JP2018140333A (ja) * 2017-02-27 2018-09-13 株式会社根岸製作所 不飽和結合を有する揮発性有機化合物モノマーを含有する排気の脱臭方法
CN113144830A (zh) * 2021-03-02 2021-07-23 江苏双良新能源装备有限公司 一种pvc手套生产过程中voc废气处理装置及工艺
CN116585856A (zh) * 2023-06-21 2023-08-15 无锡海霖格科技有限公司 一种挥发性有机物吸收剂及其制备方法和吸收系统
WO2024159869A1 (fr) * 2023-02-01 2024-08-08 南通星辰合成材料有限公司 Agent d'absorption de gaz résiduaire au toluène pour la production d'une résine époxy, procédé de traitement et système

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02303522A (ja) * 1989-05-16 1990-12-17 Toho Chem Ind Co Ltd 吸収剤組成物
JPH06341737A (ja) * 1993-05-28 1994-12-13 Nippondenso Co Ltd 冷媒再生装置
JPH10249196A (ja) * 1997-03-17 1998-09-22 Asahi Denka Kogyo Kk 有機ガス吸収剤
JP2001505478A (ja) * 1996-07-22 2001-04-24 ダウ ドイチュランド インコーポレイティド 煙道ガス中のポリハロゲン化芳香族化合物又は多核芳香族炭化水素の濃度を減少させる方法
JP2008540939A (ja) * 2005-04-07 2008-11-20 マシスン トリ−ガス，インコーポレイティド 流体を貯蔵および浄化する方法およびシステム
JP2009195828A (ja) * 2008-02-21 2009-09-03 Kenji Nakajima 有機溶剤を含む被処理ガスの処理設備、有機溶剤の回収方法および有機溶剤の再利用方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02303522A (ja) * 1989-05-16 1990-12-17 Toho Chem Ind Co Ltd 吸収剤組成物
JPH06341737A (ja) * 1993-05-28 1994-12-13 Nippondenso Co Ltd 冷媒再生装置
JP2001505478A (ja) * 1996-07-22 2001-04-24 ダウ ドイチュランド インコーポレイティド 煙道ガス中のポリハロゲン化芳香族化合物又は多核芳香族炭化水素の濃度を減少させる方法
JPH10249196A (ja) * 1997-03-17 1998-09-22 Asahi Denka Kogyo Kk 有機ガス吸収剤
JP2008540939A (ja) * 2005-04-07 2008-11-20 マシスン トリ−ガス，インコーポレイティド 流体を貯蔵および浄化する方法およびシステム
JP2009195828A (ja) * 2008-02-21 2009-09-03 Kenji Nakajima 有機溶剤を含む被処理ガスの処理設備、有機溶剤の回収方法および有機溶剤の再利用方法

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3320963A1 (fr) * 2016-11-15 2018-05-16 Basf Se Procédé pour enlever un hydrocarbure aromatique d'un flux de gaz
WO2018091385A1 (fr) * 2016-11-15 2018-05-24 Basf Se Procédé permettant un enrichissement en hydrocarbure aromatique à partir d'un flux de gaz brut
JP2018140333A (ja) * 2017-02-27 2018-09-13 株式会社根岸製作所 不飽和結合を有する揮発性有機化合物モノマーを含有する排気の脱臭方法
JP7042456B2 (ja) 2017-02-27 2022-03-28 株式会社根岸製作所 不飽和結合を有する揮発性有機化合物モノマーを含有する排気の脱臭方法
CN113144830A (zh) * 2021-03-02 2021-07-23 江苏双良新能源装备有限公司 一种pvc手套生产过程中voc废气处理装置及工艺
WO2024159869A1 (fr) * 2023-02-01 2024-08-08 南通星辰合成材料有限公司 Agent d'absorption de gaz résiduaire au toluène pour la production d'une résine époxy, procédé de traitement et système
CN116585856A (zh) * 2023-06-21 2023-08-15 无锡海霖格科技有限公司 一种挥发性有机物吸收剂及其制备方法和吸收系统

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