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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C17/00—Preparation of halogenated hydrocarbons
  • C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
  • C07C17/363—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by elimination of carboxyl groups
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  • A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
  • A62D3/20—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by hydropyrolysis or destructive steam gasification, e.g. using water and heat or supercritical water, to effect chemical change
• • A—HUMAN NECESSITIES
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  • A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
  • A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
  • A62D3/36—Detoxification by using acid or alkaline reagents
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  • A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
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  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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  • C02F1/66—Treatment of water, waste water, or sewage by neutralisation; pH adjustment
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  • C07—ORGANIC CHEMISTRY
  • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
  • C07B35/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving a change in the type of bonding between two carbon atoms already directly linked
  • C07B35/06—Decomposition, e.g. elimination of halogens, water or hydrogen halides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C19/00—Acyclic saturated compounds containing halogen atoms
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/04—Saturated ethers
  • C07C43/12—Saturated ethers containing halogen
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
  • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
  • C07C53/19—Acids containing three or more carbon atoms
  • C07C53/21—Acids containing three or more carbon atoms containing fluorine
• • A—HUMAN NECESSITIES
  • A62—LIFE-SAVING; FIRE-FIGHTING
  • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
  • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
  • A62D2101/20—Organic substances
  • A62D2101/22—Organic substances containing halogen
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F2101/00—Nature of the contaminant
  • C02F2101/30—Organic compounds
  • C02F2101/36—Organic compounds containing halogen

Definitions

• the present invention relates to a method for decomposing polyfluorocarboxylic acids.
• This application claims priority based on Japanese Patent Application No. 2021-077490 filed in Japan on April 30, 2021, the content of which is incorporated herein.
• Non-Patent Document 1 describes that when heated at 307° C. for 65 hours, it decomposes by 4%.
• various studies have been made on methods for decomposing polyfluorocarboxylic acids in particular. For example, a method of reacting with iron powder at a high temperature of 350 ° C.
• Patent Document 1 a method of decomposing by reaction with hydrogen peroxide (Patent Document 2), a method of heating with peroxodisulfate ions (Patent Document 3), etc. It has been known. However, the method described in Patent Literature 1 requires a very high-temperature reaction, and is severely restricted in equipment for industrial implementation. In the method described in Patent Document 2, the decomposition rate of polyfluorocarboxylic acid is low. In the method described in Patent Document 3, an excessive amount of peroxodisulfate, which is an oxidizing substance, is required in order to achieve a high decomposition rate, resulting in costs and management.
• the present invention aims to provide a method for efficiently decomposing polyfluorocarboxylic acids in a simpler and cheaper manner.
• the inventors of the present invention have found that the above problems can be solved by the following configuration. Specifically, the present inventors have found that the decomposition of polyfluorocarboxylic acids is improved when a mixture containing polyfluorocarboxylic acids, water, and a basic compound is heated. [1] A mixture containing a polyfluorocarboxylic acid, water, and a basic compound is heated, and the mass ratio of the polyfluorocarboxylic acid to water (polyfluorocarboxylic acid:water) is 1:1.
• the basic compound is at least one selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate.
• the decomposition method according to any one of [1] to [4], which is more preferably 1 hour or more and less than 12 hours, and still more preferably 1 hour or more and less than 6 hours.
• the polyfluorocarboxylic acids have a fluorinated alkyl group having 4 to 16 carbon atoms, preferably a fluorinated alkyl group having 5 to 15 carbon atoms, and a fluorinated alkyl group having 6 to 14 carbon atoms.
• the polyfluorocarboxylic acid is a perfluorocarboxylic acid or a salt thereof, preferably nonafluoropentanoic acid, perfluorooctanoic acid, perfluorononanoic acid, perfluorodecanoic acid, perfluoroundecanoic acid, perfluorododecanoic acid or a salt thereof, [ 1] The decomposition method according to any one of [6]. [8] The decomposition method according to [7], wherein the perfluorocarboxylic acid is perfluorooctanoic acid.
• the basic compound is at least one selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate.
• compound preferably sodium hydroxide or potassium hydroxide, more preferably potassium hydroxide, the production method according to [10].
• the temperature in the heating is more than 150°C and less than 195°C, preferably 155 to 190°C, more preferably 160 to 185°C, even more preferably 165 to 180°C, and the heating time is preferably 1 to 24 hours,
• the production method according to any one of [10] to [13], which is more preferably 1 hour or more and less than 12 hours, and further preferably 1 hour or more and less than 6 hours.
• the polyfluorocarboxylic acids have a fluorinated alkyl group having 6 to 16 carbon atoms, preferably a fluorinated alkyl group having 5 to 15 carbon atoms, and a fluorinated alkyl group having 6 to 14 carbon atoms.
• the polyfluorocarboxylic acid is a perfluorocarboxylic acid or a salt thereof, preferably nonafluoropentanoic acid, perfluorooctanoic acid, perfluorononanoic acid, perfluorodecanoic acid, perfluoroundecanoic acid, perfluorododecanoic acid or a salt thereof, [ 10] The production method according to any one of [15]. [17] The production method according to [16], wherein the perfluorocarboxylic acid is perfluorooctanoic acid.
• polyfluorocarboxylic acids can be efficiently decomposed by a simpler and cheaper method.
• a first aspect of the present invention is a method for decomposing perfluorocarboxylic acids, in which a mixture containing polyfluorocarboxylic acids, water, and a basic compound is heated.
• a polyfluorocarboxylic acid means a compound (polyfluorocarboxylic acid) in which a monovalent organic group having two or more fluorine atoms is bonded to a carboxy group, and salts and precursors thereof.
• the salt include alkali metal salts, alkaline earth metal salts, and ammonium salts of polyfluorocarboxylic acids, with lithium salts, sodium salts, potassium salts, ammonium salts, calcium salts, and magnesium salts being preferred. More preferred are sodium, potassium and ammonium salts.
• the precursor include fluorinated alcohols, fluorinated aldehydes, fluorine atom-containing acid halides, and fluorinated carboxylic acid esters.
• a fluorinated alcohol is a compound in which the oxygen atom of the carbonyl group in the carboxy group of polyfluorocarboxylic acid is replaced with two hydrogen atoms.
• a fluorinated aldehyde is a compound in which a hydroxyl group in the carboxy group of a polyfluorocarboxylic acid is substituted with a hydrogen atom.
• An acid halide having a fluorine atom is a compound in which the hydroxyl group in the carboxy group of polyfluorocarboxylic acid is substituted with a halogen atom.
• a fluorinated carboxylic acid ester is a compound in which a hydrogen atom of a hydroxyl group in a carboxy group of a polyfluorocarboxylic acid is substituted with a monovalent hydrocarbon group.
• the polyfluorocarboxylic acids of the present embodiment preferably have a fluorinated alkyl group, and more preferably have a perfluoroalkyl group.
• the fluorinated alkyl group may be a fluorinated alkyl group having an etheric oxygen atom.
• a fluorinated alkyl group having an etheric oxygen atom means a fluorinated alkyl group having an oxygen atom inserted between carbon-carbon bonds in the fluorinated alkyl group.
• the fluorinated alkyl group is preferably attached to the carbon atom of the carbonyl group in the polyfluorocarboxylic acids.
• the number of carbon atoms in the fluorinated alkyl group or perfluoroalkyl group is preferably 4-16, more preferably 5-15, even more preferably 6-14.
• the polyfluorocarboxylic acid is preferably a carboxylic acid having a perfluoroalkyl group, a salt thereof, or a precursor thereof, and more preferably a carboxylic acid having a perfluoroalkyl group or a salt thereof.
• the fluorinated alkyl group is an alkyl group represented by —C n H 2n+1 (n is a positive integer) or a group in which at least two hydrogen atoms of a cycloalkyl group are replaced with fluorine atoms. , may be linear or branched.
• a perfluoroalkyl group is an alkyl group represented by —C n H 2n+1 (n is a positive integer) or a group in which all hydrogen atoms of a cycloalkyl group are replaced with fluorine atoms.
• polyfluorocarboxylic acids having a fluorinated alkyl group having 4 to 16 carbon atoms include polyfluoropentanoic acid, polyfluorooctanoic acid, polyfluorononanoic acid, polyfluorodecanoic acid, polyfluoroundecanoic acid, polyfluorododecanoic acid, poly fluorotetradecanoic acid and the like.
• Carboxylic acids having a perfluoroalkyl group include nonafluoropentanoic acid, perfluorooctanoic acid, perfluorononanoic acid, perfluorodecanoic acid, perfluoroundecanoic acid, and perfluorododecanoic acid, with perfluorooctanoic acid being preferred.
• the polyfluorocarboxylic acid of this embodiment is preferably a perfluorocarboxylic acid represented by the following general formula (A1) or a salt thereof. (R F COO) n1 M (A1)
• R F is a perfluoroalkyl group having 4 to 16 carbon atoms which may have an etheric oxygen atom.
• Perfluoroalkyl groups are as described above.
• the perfluoroalkyl group may be linear, branched, or have a cyclic structure.
• a perfluoroalkyl group is preferably linear.
• the number of carbon atoms is more preferably 4 to 16, more preferably 5 to 15, and even more preferably 6 to 14.
• the number of etheric oxygen atoms is preferably 1 to 4, more preferably 1 to 3.
• M represents H, Li, Na, K, NH4 , Ca, or Mg.
• n1 is 1 when M is H, Li, Na, K, NH4, n1 is 2 when M is Ca, Mg.
• M is preferably Li, Na, K, NH4 . They are water soluble and easy to handle.
• polyfluorocarboxylic acids are heated with water and a basic compound.
• Polyfluorocarboxylic acids may or may not be dissolved in water, and are preferably dissolved.
• the mass ratio of polyfluorocarboxylic acids to water is preferably 1:1 ⁇ 10 15 to 1:0.01, more preferably 1:1 ⁇ 10 12 to 1:0.1. , 1:1 ⁇ 10 9 to 1:1 is more preferred, and 1:1 ⁇ 10 6 to 1:10 is particularly preferred.
• efficient decomposition is possible even if the concentration of polyfluorocarboxylic acids is high, and further reduction is possible even if the concentration of polyfluorocarboxylic acids is low.
• the concentration of perfluorooctanoic acids be 25 mass ppb or less.
• the concentration of perfluorooctanoic acid can be reduced to 25 mass ppb or less, further to about 10 mass ppb by adjusting the reaction time and reaction temperature.
• the content of polyfluorocarboxylic acids relative to the total mass of the mixture is preferably 0.001 to 5% by mass, more preferably 0.005 to 4% by mass, and even more preferably 0.01 to 3% by mass.
• the heating temperature is preferably higher than 150°C and lower than 195°C, more preferably 155 to 190°C, even more preferably 160 to 185°C, and particularly preferably 165 to 180°C. If it is higher than 150°C, a sufficient decomposition rate can be ensured, which is suitable for industrial implementation. If the temperature is less than 195° C., the temperature can be easily adjusted by heating steam or the like. Heating temperature means the temperature of the mixture during heating.
• the heating time is not particularly limited, and is usually 1 to 24 hours. According to the method of the present embodiment, polyfluorocarboxylic acids can be sufficiently decomposed in a short time of less than 12 hours, further less than 6 hours.
• polyfluorocarboxylic acids are acidic compounds, especially at high concentrations, basic compounds are added to increase the decomposition rate of polyfluorocarboxylic acids and to prevent corrosion.
• basic compounds include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and the like.
• potassium hydroxide is more preferred.
• the amount of the basic compound in the mixture is preferably equal to or greater than that of the polyfluorocarboxylic acids.
• the ratio of the number of moles of the basic compound to the number of moles of the polyfluorocarboxylic acid in the mixture is preferably from 0.01 to 50,000,000, more preferably from 0.1 to 500,000, and even more preferably from 1 to 5,000.
• the content of the basic compound with respect to the total mass of the mixture is preferably 50% by mass or less, more preferably 30% by mass or less, and even more preferably 15% by mass or less. If it is below the above upper limit, it can be easily supplied to the treatment process using a solution of sodium hydroxide, potassium hydroxide, or the like.
• the basic compound content relative to the total mass of the mixture is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and even more preferably 1% by mass or more. That is, the content of the basic compound with respect to the total mass of the mixture is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass, even more preferably 1 to 15% by mass.
• substances other than the above-described polyfluorocarboxylic acids, water, and basic compounds may coexist.
• the substance include alcohols, carboxylic acids, salts of inorganic acids and organic acids, and the like.
• One aspect of the present invention preferably contains methanol.
• a further aspect of the present invention preferably contains potassium iodide.
• metal powder, hydrogen peroxide, ozone, and peroxodisulfate ions are not substantially contained, and more preferably that they are not contained.
• substantially free means that the total content thereof is 1% by mass or less relative to the total mass of the mixture.
• the metal powder include powdered iron, copper, lead, aluminum, zinc, and the like.
• a fluorinated compound obtained by decomposing a polyfluorocarboxylic acid by the method of the present embodiment is represented by the following formula (D1).
• Rf-H (D1) Rf is a fluorinated alkyl group having 3 to 15 carbon atoms which may have an etheric oxygen atom.
• the fluorinated alkyl groups here are the groups as defined above.
• the fluorinated alkyl group may be linear, branched, or have a ring structure.
• the fluorinated alkyl group is preferably linear. Further, the number of carbon atoms is more preferably 4-14, more preferably 5-13.
• the fluorinated compound (D1) is water-insoluble and can be easily separated from water used for decomposition by layer separation.
• the method of this embodiment may be carried out in the presence of nitrogen, air, or other gases, or may be carried out in a state in which these gases are degassed.
• the operating pressure is not particularly limited, and it may be pressurized or depressurized, but by-products produced by decomposition while depressurizing can be removed at the same time.
• the absolute pressure when reducing the pressure is preferably 0.001 to 0.099 MPa, more preferably 0.01 to 0.09 MPa, even more preferably 0.1 to 0.09 MPa.
• any equipment that does not corrode can be used, and various metals, glasses, and ceramics can be used.
• the decomposition rate of polyfluorocarboxylic acids calculated by the following formula based on the mass of polyfluorocarboxylic acids before decomposition can be 90.0% or more. It can be 95.0% or more.
• the mass of the polyfluorocarboxylic acid in the mixture can be calculated from measurement by liquid chromatography-mass spectrometry, which will be described later.
• the method of the present embodiment can efficiently decompose polyfluorocarboxylic acids.
• Decomposition rate (%) (mass of polyfluorocarboxylic acids before decomposition - mass of polyfluorocarboxylic acids after decomposition) / mass of polyfluorocarboxylic acids before decomposition x 100
• the initial pH of the mixture containing the basic compound before decomposition is preferably 10 or higher, more preferably 12 or higher.
• the upper limit of the initial pH is usually 14. That is, the initial pH is preferably 10-14, more preferably 10-12. If the initial pH is within the above range, the decomposition rate of polyfluorocarboxylic acids is further improved.
• a second aspect of the present invention is a method for producing a fluorinated compound, comprising decomposing a polyfluorocarboxylic acid to obtain a fluorinated compound.
• the details of each compound, its decomposition method, and the fluorinated compound are as described above in the first aspect.
• the recovery rate of the fluorinated compound which is the decomposition product of the polyfluorocarboxylic acid, calculated by the following formula based on the mass of the polyfluorocarboxylic acid before decomposition is 60.0% or more. It can be 70.0% or more.
• the mass of the fluorinated compound in the mixture can be determined by a method of specifying the structure by NMR and then calculating the number of moles and converting it into a mass, or a method of calculating according to the liquid chromatography-mass spectrometry method described later. can.
• a fluorinated compound which is a decomposition product of polyfluorocarboxylic acids
• Recovery rate (%) (mass of fluorinated compound produced by decomposition/molecular weight of fluorinated compound produced by decomposition)/(mass of polyfluorocarboxylic acid before decomposition/molecular weight of polyfluorocarboxylic acid) x 100
• Test liquid 1 A mixture was obtained by mixing 0.15 g of perfluorooctanoic acid (PFOA) and 1,500.0 g of distilled water to obtain a test liquid 1.
• PFOA concentration in test liquid 1 was measured, it was 87 mass ppm.
• a 1-liter Hastelloy autoclave equipped with a stirrer was evacuated with a vacuum pump, test liquid 1 was charged in such a way that air did not enter, the internal temperature was adjusted to 170° C. with an oil bath, and the autoclave was kept under stirring for 5 hours. . After cooling, the PFOA concentration in the content was measured and found to be 5.9 ppm by mass, and the PFOA decomposition rate calculated based on the concentration of the charged PFOA was 93.2%.
• Example 1 1.5 g of PFOA, 1,000.2 g of distilled water, and 2.1 g of 48% potassium hydroxide aqueous solution were mixed to obtain a 1,500 mass ppm PFOA solution (hereinafter referred to as PFOA solution 1). Further, 54.95 g of PFOA solution 1, 464.8 g of distilled water, and 31.35 g of 48% potassium hydroxide aqueous solution were mixed to obtain a mixture, which was used as test liquid 2. When the PFOA concentration in test liquid 2 was measured, it was 154 mass ppm. After holding at 170° C. for 5 hours and cooling in the same manner as in Comparative Example 1, the PFOA concentration in the contents was measured and found to be 5.9 ppm by mass. The calculated percentage was 96.2%.
• Example 2 A mixture was obtained by mixing 55.21 g of PFOA solution 1, 434.9 g of distilled water, 30.51 g of 48% potassium hydroxide aqueous solution, and 30.4 g of potassium iodide, and used as test solution 3.
• the PFOA concentration in test liquid 3 was measured, it was 170 mass ppm.
• the PFOA concentration in the contents was measured and found to be 4.2 ppm by mass. The percentage was calculated to be 97.5%.
• Example 3 55.04 g of PFOA solution 1, 215.2 g of distilled water, 32.56 g of 48% aqueous potassium hydroxide solution, and 30.61 g of potassium iodide and 220.08 g of methanol are mixed to obtain a mixture, A test liquid 4 was used. When the PFOA concentration in test liquid 4 was measured, it was 154 mass ppm. After holding at 170° C. for 5 hours and cooling in the same manner as in Comparative Example 1, the PFOA concentration in the contents was measured and found to be 0.3 ppm by mass. The percentage was calculated to be 99.8%.
• Example 4 15.4 g of PFOA, 449.0 g of distilled water, and 50.7 g of 48% potassium hydroxide aqueous solution were mixed to obtain test solution 5 as a slurry mixture. It was carried out in the same manner as in Comparative Example 1 except that the autoclave was opened and the test solution 5 was charged. The resulting liquid was transparent and separated into two layers, and 10.1 g of the lower layer and 494.75 g of the upper layer were recovered. When the PFOA concentration in the upper layer was measured, it was 600 mass ppm. Further, when the decomposition rate of PFOA was calculated, it was 98.1%. When the lower layer was collected and analyzed by NMR , it was confirmed to be C7F15H , and the recovery rate based on the mass of the charged PFOA was 73.4%.
• polyfluorocarboxylic acids can be decomposed at a high decomposition rate, and fluorinated compounds, which are decomposition products of polyfluorocarboxylic acids, can be efficiently recovered.
• the method of the present invention is effective in preventing environmental pollution caused by fluorine-containing organic compounds.

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