JP2006212617A - Separation and recovery method of phosphoric acid, organic acid, and amino acid, and treatment method of organic materials - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a separation and recovering method of phosphoric acid, an organic acid, and an amino acid with a high efficiency. <P>SOLUTION: In the separation and recovery method of phosphoric acid, an organic acid, and an amino acid, a liquid to be treated containing phosphoric acid, an organic acid, and an amino acid is caused to pass through a strongly basic anion exchange resin to let the resin to adsorb the phosphoric acid, and subsequently an aqueous solution of sodium hydroxide is caused to pass through the strongly basic anion exchange resin to let the resin to desorb the phosphoric acid, which is subsequently recovered. The organic acid and amino acid passing through the strongly basic anion exchange resin unadsorbed are caused to pass through a weakly basic anion exchange resin (preferably an ultra porous PEI chitosan resin) to let the resin to adsorb the organic acid, and subsequently an aqueous solution of sodium hydroxide is caused to pass through the weakly basic anion exchange resin to let the resin to desorb the organic acid, which is subsequently recovered. The amino acid passing through the weakly basic anion exchange resin unadsorbed can be isolated by a well-know method in the art. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a method for separating and recovering phosphoric acid, organic acid, and amino acid, and a method for treating organic substances.

  Conventionally, in the treatment method of phosphorus-containing organic wastewater, as means for removing phosphorus and nitrogen, there are many methods combining biological nitrification denitrification treatment method, anaerobic aerobic method, coagulation precipitation method, etc. One example is a high-load denitrification process. In addition, as a means of recovering phosphorus from the high-load denitrification process, a magnesium compound is added at the previous stage of the biological treatment means, the produced magnesium phosphate compound is added, and the produced magnesium ammonium phosphate is solid-liquid together with concentrated sludge. A process of separating and composting is disclosed (for example, see Patent Document 1).

  However, the conventional high-load denitrogenation process has problems such as complicated operation due to large load fluctuations related to biological treatment means, and the necessity of using a large amount of chemicals for dephosphorization. was there. Moreover, since the process with phosphorus collection | recovery disclosed by the said patent document 1 is isolate | separated in the state with which the collect | recovered phosphorus and sludge were mixed, the recycling | reuse use of the collect | recovered phosphorus is restricted to a compost. Therefore, there is a problem that phosphorus cannot be efficiently recovered.

The organic acid separation method is used for, for example, concentrating the organic acid in a facility where the organic acid is used or manufactured, or removing the organic acid from waste water of a factory or the like.
In the case of concentrating the organic acid, after the organic acid is adsorbed on, for example, an anion exchange resin (substance), the organic acid is eluted from the anion exchange resin using an alkaline aqueous solution or an organic solvent. A concentrated organic acid is obtained by performing a treatment such as distillation or membrane separation on the solution from which the organic acid is eluted.

  On the other hand, in the case of wastewater treatment for removing organic acid, after the organic acid contained in the wastewater is adsorbed on the anion exchange resin, the organic acid is separated from the anion exchange resin using an alkaline aqueous solution. Is going.

  In any of the above cases, in order to separate the organic acid from the anion exchange resin when used for the concentration of the organic acid, a large amount of an aqueous alkali solution or the like is required, and in order to concentrate the separated organic acid, Many processes such as distillation are required. Therefore, there is a drawback that it takes much cost to separate and recover the concentrated organic acid from the anion exchange resin (see, for example, Patent Document 2).

In addition, it is clear that when processing operations such as subcritical water treatment, fermentation, and superheated steam carbonization are performed on fish meal, activated sludge, meat and bone meal, etc., a large amount of phosphoric acid, various amino acids and organic acids are produced in the aqueous phase. It has become. In order to effectively use these as resources, it is necessary to develop a highly efficient separation and recovery process.
Japanese Examined Patent Publication No. 1-2558 JP 2004-089904 A

  That is, the present invention has been made in view of the above problems, and an object thereof is to provide a method for separating and recovering phosphoric acid, organic acid and amino acid with high efficiency.

  In order to achieve the above object, in the method for separating and recovering phosphoric acid according to the present invention, the liquid to be treated containing phosphoric acid is passed through a strongly basic anion exchange resin to remove phosphoric acid from a strongly basic anion. Next, the aqueous solution of sodium hydroxide is passed through the strong basic anion exchange resin, and the phosphoric acid is desorbed to recover the phosphoric acid.

  In the organic acid separation / recovery method of the present invention, the liquid to be treated containing an organic acid is passed through a weakly basic anion exchange resin to adsorb the organic acid to the weakly basic anion exchange resin, Then, an aqueous solution of sodium hydroxide is passed through the weakly basic anion exchange resin, and the organic acid is desorbed to recover the organic acid.

  In the method for separating and recovering phosphoric acid and organic acid of the present invention, the liquid to be treated containing phosphoric acid and organic acid is passed through a strongly basic anion exchange resin, and phosphoric acid is strongly basic anion. Next, the aqueous solution of sodium hydroxide is passed through the strong basic anion exchange resin to desorb the phosphoric acid, the phosphoric acid is recovered, and the strong basic anion exchange resin is The liquid to be treated is passed through a weakly basic anion exchange resin to adsorb an organic acid on the weakly basic anion exchange resin, and then an aqueous sodium hydroxide solution is added to the weakly basic anion exchange resin. And the organic acid is desorbed to recover the organic acid.

  In the separation / recovery method, the liquid to be treated is obtained by decomposing, in a subcritical state, organic waste including food waste and garbage including sludge, fish meal, animal manure, waste wood, and waste plastic. There may be.

  The method for separating and recovering phosphoric acid and amino acid according to the present invention is a method for separating and recovering phosphoric acid and amino acid, wherein a liquid to be treated containing phosphoric acid and an organic acid is used as a strongly basic anion exchange resin. Through which the phosphoric acid is adsorbed on the strongly basic anion exchange resin, and then an aqueous sodium hydroxide solution is passed through the strong basic anion exchange resin to desorb the phosphoric acid, The acid is recovered, and the amino acid is separated and recovered using the liquid to be treated that has passed through the strongly basic anion exchange resin.

  In the method for separating and recovering an organic acid and an amino acid according to the present invention, the liquid to be treated containing the organic acid and the amino acid is passed through a weakly basic anion exchange resin to remove the organic acid from the weakly basic anion exchange resin. Next, an aqueous solution of sodium hydroxide is passed through the weakly basic anion exchange resin to desorb the organic acid, and the organic acid is recovered and passed through the weakly basic anion exchange resin. Amino acids are separated and recovered using the treated liquid.

  In the method for separating and recovering phosphoric acid, organic acid and amino acid of the present invention, the liquid to be treated containing phosphoric acid, organic acid and amino acid is passed through a strongly basic anion exchange resin to strengthen phosphoric acid. Adsorbed on a basic anion exchange resin, and then a sodium hydroxide aqueous solution is passed through the strong basic anion exchange resin to desorb the phosphoric acid to recover the phosphoric acid; The liquid to be treated that has passed through the anion exchange resin is passed through the weakly basic anion exchange resin to adsorb the organic acid to the weakly basic anion exchange resin, and then the aqueous sodium hydroxide solution is added to the weakly aqueous anion exchange resin. The organic acid is desorbed by passing through a basic anion exchange resin to recover the organic acid, and an amino acid is separated and recovered using the liquid to be treated that has passed through the weak basic anion exchange resin.

  In the organic acid separation / recovery method of the present invention, a liquid to be treated containing two or more organic acids is allowed to pass through a weakly basic anion exchange resin to adsorb the organic acid to the weakly basic anion exchange resin. Next, the aqueous solution of sodium hydroxide is passed through the weakly basic anion exchange resin to desorb the organic acid, and the organic acid is recovered. The conditions for adsorbing to the neutral anion exchange resin and the conditions for the organic acid to desorb from the weakly basic anion exchange resin are adjusted to recover each organic acid.

  In the method for treating an organic substance of the present invention, a liquid to be treated obtained by sublimation of an organic substance with subcritical water treatment, fermentation, or superheated steam, which contains phosphoric acid, an amino acid, and an organic acid, A strong basic anion exchange resin is passed through to adsorb phosphoric acid on the strong basic anion exchange resin, and then an aqueous sodium hydroxide solution is passed through the strong basic anion exchange resin to Acid is desorbed, phosphoric acid is recovered, and the liquid to be treated that has passed through the strongly basic anion exchange resin is passed through the weakly basic anion exchange resin, so that the organic acid is weakly anion exchanged. Next, the aqueous solution of sodium hydroxide is passed through the weakly basic anion exchange resin to desorb the organic acid to recover the organic acid, and the weakly basic anion exchange resin is Using the processed liquid that passed The amino acid to separate and recover.

  In the method for separating and recovering phosphoric acid, organic acid and amino acid of the present invention with high efficiency, phosphoric acid, organic acid and amino acid are selectively used by using strongly basic anion exchange resin and weakly basic anion exchange resin. In addition, it can be separated and recovered efficiently. As a result, these can be effectively used as resources or energy.

  The best mode for carrying out the present invention will be described below. In addition, this invention is not limited by these.

  In the present invention, a phosphoric acid single component system, a phosphoric acid and organic acid two component system, a method for separating and recovering phosphoric acid with high selectivity, an organic acid two component system, an organic acid and two amino acid components In any system, organic acids or organic acids and amino acids can be separated and recovered with high selectivity, and the above two methods are combined to efficiently combine phosphoric acid, amino acids, and organic acids, Separate and collect.

[Separation and recovery of phosphoric acid]
Separation of phosphoric acid is performed using an OH type strongly basic anion exchange resin. In the present invention, first, it has been found that when a liquid containing phosphoric acid is passed through an OH type strongly basic anion exchange resin column, a large amount of phosphoric acid is adsorbed. The OH type strongly basic anion exchange resin can separate phosphoric acid with high selectivity in a phosphoric acid single component system.

  Next, when a mixture of phosphoric acid, amino acid, and organic acid was passed through an OH type strongly basic anion exchange resin column, it was found that only phosphoric acid was adsorbed, and so-called complete separation that the others passed through occurred. OH type strongly basic anion exchange resin is highly selective in phosphoric acid and organic acid two-component system, phosphoric acid and amino acid two-component system, phosphoric acid and organic acid and amino acid three-component system. Can be separated. In any of the two-component system and the three-component system, the organic acid and the amino acid are not limited to one type and may be a plurality of types.

  In the case of a two-component system or a three-component system, the adsorption amount of phosphoric acid to the OH type strongly basic anion exchange resin can be adjusted by selecting the pH of the liquid to be treated.

  The recovery of phosphoric acid is performed by desorbing the adsorbed phosphoric acid with 0.5 M to 3 M NaOH after the column is saturated with phosphoric acid. This desorption can be performed with a smaller amount of NaOH than the amount of the liquid to be treated. Therefore, phosphoric acid can be concentrated and recovered.

[Separation and recovery of organic acids]
The recovery of the organic acid is performed using a weakly basic anion exchange resin. Of the weakly basic anion exchange resins, superporous PEI (polyethyleneimine) chitosan resin is preferable. In the present invention, a liquid containing an organic acid is passed through a commercially available weakly basic anion exchange resin column or superporous PEI (polyethyleneimine) chitosan resin (with a porosity of about 0.8 and a pore diameter of about 0.1 micron). And found that organic acids are adsorbed. This adsorption can selectively separate the organic acid in both the organic acid and organic acid binary system and the organic acid and amino acid binary system. In particular, in the case of an organic acid and an organic acid two-component system, the two components can be separated by the strength of adsorption of the organic acid to the ion exchange resin. The strength of organic acid adsorption is, for example, formic acid> pyroglutamic acid >> lactic acid >> acetic acid.

  The recovery of the organic acid is performed by desorbing the adsorbed organic acid with 0.5 M to 3 M NaOH after the column is saturated with the organic acid. This desorption can be performed with a smaller amount of NaOH than the amount of the liquid to be treated. Therefore, the organic acid can be concentrated and recovered.

  When three or more kinds of organic acids are contained, individual organic acids can be separated and recovered by performing the above operations in order from those with strong adsorption. Moreover, you may use as a raw material of methane fermentation, without isolate | separating into each organic acid.

[Separation and recovery of amino acids]
The separation and recovery of amino acids are performed using a known method such as using a strongly acidic ion exchange resin.

  Each of the organic acid and amino acid may be a single component or multiple components. Even when a multi-component amino acid coexists with phosphoric acid, only phosphoric acid is adsorbed to the strongly basic anion exchange resin, and each amino acid passes with hardly adsorbing the strongly basic anion exchange resin. Even if a multi-component organic acid coexists with phosphoric acid, only phosphoric acid is adsorbed on the strongly basic anion exchange resin, and each organic acid passes with hardly adsorbing the strongly basic anion exchange resin. Even if phosphoric acid, multi-component organic acid, and multi-component amino acid coexist, only phosphoric acid is adsorbed to strongly basic anion exchange resin, and each organic acid and each amino acid is strongly basic anion exchange resin. Passes almost without adsorption.

  When a weakly basic anion exchange resin is brought into contact with a solution in which a multicomponent organic acid and a multicomponent amino acid coexist, only the organic acid is adsorbed, and each amino acid passes with almost no adsorption. Since the adsorbed organic acid has a difference in the strength of adsorption depending on the type of organic acid, component separation can be performed in the organic acid adsorption process and the desorption process with caustic soda.

[Examples to which the separation / recovery method of the present invention can be applied]
The separation / recovery method of the present invention can be applied without particular limitation when a specific acid is separated / recovered from one or more of phosphoric acid, organic acid and amino acid. For example, livestock products, agricultural products, marine products, natural organic materials such as wood and plants and their waste, food and food waste, synthetic organic materials including plastics and organochlorine compounds, rubber, fiber and their waste, and activity Sewage treatment waste containing sludge and surplus sludge, waste water treatment waste containing organic matter such as subcritical water treatment, fermentation, decomposed by heated steam, fermented solution of industrial organic acid, industrial and domestic wastewater Etc. In particular, it is preferable to use the organic matter-containing material decomposed by subcritical water treatment, fermentation, and heated steam for the separation / recovery method of the present invention.

  FIG. 1 is a diagram for explaining a process of separating phosphoric acid, amino acid, and organic acid from organic substances decomposed by subcritical water treatment, fermentation, and superheated steam by the separation / recovery method of the present invention. As shown in this figure, when operations such as subcritical water treatment, fermentation, and superheated steam carbonization are performed on organic substances, phosphoric acid, amino acids, and organic acids are generated. When these acids are separated and recovered from phosphoric acid, amino acids, and organic acids by the method shown in FIG. 1, useful acids can be obtained and reused.

  Specifically, when a fish tail that is a waste of marine products is hydrolyzed using subcritical water (473K, 5 minutes), it is separated into an aqueous phase and a solid phase. When this aqueous phase is separated using an organic solvent, an aqueous phase containing a large amount of phosphoric acid and lactic acid is obtained. When this phosphoric acid and lactic acid are used in the phosphoric acid organic acid two-component separation / recovery method, high-purity phosphoric acid can be obtained. In addition, lactic acid can be reused after being treated with a weakly basic anion exchange resin, or can be directly used for methane fermentation. For example, 0.6 t phosphoric acid and 0.4 t lactic acid can be recovered from 100 t fish.

  Moreover, the phosphoric acid in waste water is concentrated by microorganisms by activated sludge processing. When it is treated with subcritical water, microorganisms are destroyed and dissolved, and phosphoric acid present therein is dissolved in water. The concentration of phosphoric acid increases rapidly at a temperature of 180 ° C. or higher at which microorganisms decompose, and is almost constant at 220 ° C. Other main products are pyroglutamic acid, which is a protein-derived degradation product, and acetic acid derived from cellulose. By using the separation / recovery method of the present invention, phosphoric acid can be selectively adsorbed and recovered. By using other organic acids for methane fermentation, it becomes possible to make excess sludge into resources and energy.

  Thus, the hydrolyzate of organic substance using subcritical water is preferable because the useful phosphoric acid and organic acid can be easily obtained by using the separation / recovery method of the present invention.

  Hereinafter, the present invention will be described in detail with reference to examples. The present invention is not limited by these.

[Separation and recovery of phosphoric acid]
(Single component system of phosphoric acid)
Example 1
Using an experimental apparatus of a batch method or Shallow Bed method, an adsorption equilibrium relationship of phosphoric acid to an OH type strongly basic anion exchange resin column (manufactured by Mitsubishi Chemical Corporation, DIAION SA10A) was determined. The results are shown in FIG. From FIG. 2, it was found that phosphoric acid was adsorbed in a large amount, that the adsorption isotherm was not affected by the initial concentration, and that the equilibrium relationship showed a unique behavior.

(Example 2)
The influence of the inlet concentration C ₀ on the single component breakthrough curve of phosphoric acid in DIAION SA10A (change in outlet concentration with time) was shown. The results are shown in FIG. From FIG. 3, the shape of the breakthrough curve was sharp regardless of the inlet concentration. As the column inlet concentration increased, the breakthrough time decreased.

(Example 3)
An elution (desorption) curve in a phosphoric acid single component system was determined. A 1000 mol / m ³ NaOH aqueous solution was used as an eluent. The results are shown in FIG. In the figure, C ₀ is the inlet concentration of phosphoric acid in the adsorption process. In either case, a sharp elution curve was obtained, and it was found that high concentration phosphoric acid could be concentrated and recovered irreversibly in a short time.

  From Examples 1 to 3, it was found that phosphoric acid can be highly selectively separated by using an OH type strongly basic anion exchange resin column.

(Phosphoric acid and organic acid two-component system)
Example 4
The two-component adsorption equilibrium relation of phosphoric acid-lactic acid with respect to DIAION SA10A) was determined. The results are shown in FIG. It was found that phosphoric acid was selectively adsorbed on DIAIONSA 10A over lactic acid. For other organic acids (formic acid, pyroglutamic acid, and acetic acid), the adsorption equilibrium relationship was similarly determined, and phosphoric acid was selectively adsorbed.

(Example 5)
The binary breakthrough curve and elution curve of phosphoric acid and lactic acid in DIAION SA10A were determined. The results are shown in FIG. FIG. 6 (a) shows that phosphoric acid is highly selectively adsorbed. Further, from FIG. 6 (b), it was found that phosphoric acid was separated with a purity of 90% or more. It was also found that high concentration of phosphoric acid can be recovered.

  From Examples 4 and 5, it was found that phosphoric acid can be highly selectively separated even in a two-component system of phosphoric acid and organic acid when an OH type strongly basic anion exchange resin column is used.

[Separation and recovery of amino acids and organic acids]
(2 component system of phosphoric acid and organic acid)
(Example 6)
The pH dependence of the adsorption amounts of pyroglutamic acid and L-alanine in the superporous PEI chitosan resin (PEI-Ch) was determined. The results are shown in FIG. L-alanine did not adsorb in the entire pH range. On the other hand, pyroglutamic acid showed the maximum adsorption amount around pH 3.7.

(Example 7)
A binary breakthrough curve and an elution curve of pyroglutamic acid and L-alanine in PEI-Ch were determined. The results are shown in FIG. FIG. 8 (a) clearly shows that only pyroglutamic acid is adsorbed and complete separation from amino acids is possible. From FIG. 8 (b), it was found that high concentration pyroglutamic acid not contaminated with L-alanine can be concentrated and recovered.

(Organic acid two-component system)
(Example 8)
The adsorption isotherm of lactic acid and pyroglutamic acid in PEI-Ch was determined. The results are shown in FIG. FIG. 9 shows that pyroglutamic acid has higher selectivity than lactic acid, and thus PEI-Ch is effective in separating organic acids.

Example 9
The adsorption isotherm of lactic acid and acetic acid in PEI-Ch was determined. The results are shown in FIG. FIG. 10 shows that lactic acid has higher adsorption selectivity than acetic acid.
(Example 10)
The pH dependency of the amount of lactic acid and acetic acid adsorbed on PEI-Ch was determined. The results are shown in FIG. From FIG. 11, the difference in the adsorption amount of lactic acid and acetic acid was maximized at pH = 2.01.

Example 9
The adsorption isotherm of lactic acid and acetic acid in PEI-Ch was determined. The results are shown in FIG. FIG. 10 shows that lactic acid has higher adsorption selectivity than acetic acid.

(Example 10)
The pH dependency of the amount of lactic acid and acetic acid adsorbed on PEI-Ch was determined. The results are shown in FIG. From FIG. 11, the difference in the adsorption amount of lactic acid and acetic acid was maximized at pH = 2.01.

(Example 11)
The adsorption isotherm of lactic acid and formic acid in PEI-Ch was determined. The results are shown in FIG. From FIG. 12, it was found that formic acid has higher adsorption selectivity than lactic acid.

(Example 12)
The pH dependence of the amount of lactic acid and formic acid adsorbed on PEI-Ch was determined. The results are shown in FIG. From FIG. 13, at pH = 2.09, the difference in the adsorption amount of lactic acid and acetic acid was maximized.

(Example 13)
The adsorption isotherm of lactic acid and pyroglutamic acid in PEI-Ch was determined. The results are shown in FIG. FIG. 15 indicates that pyroglutamic acid has higher adsorption selectivity than lactic acid.

(Example 14)
The pH dependence of the adsorption amounts of lactic acid and pyroglutamic acid in PEI-Ch was determined. The results are shown in FIG. From FIG. 16, at pH = 1.74, the difference in the adsorption amount of lactic acid and pyroglutamic acid was maximized.

As a result of examining the adsorption isotherms of lactic acid, acetic acid, formic acid and pyroglutamic acid in PEI-Ch from Examples 8 to 14, the strength of adsorption is
Since formic acid, pyroglutamic acid> lactic acid> acetic acid, it was found that the components could be separated.

(Example 15)
Fish meal (100 t) was hydrolyzed using subcritical water (473 K, 5 minutes), and separated into an aqueous phase and a solid phase. The aqueous phase contained a large amount of phosphoric acid and lactic acid. High purity phosphoric acid (0.6 t) can be obtained by using the phosphoric acid and lactic acid by using the above-described phosphoric acid organic acid two-component separation / recovery method. In addition, lactic acid (0.4 t) was obtained.

(Example 16)
The surplus sludge of activated sludge having a water content of 91.4% was hydrolyzed using subcritical water. The yield of organic acid and phosphoric acid contained in the water-soluble component of this decomposition product corresponding to the reaction temperature was examined. The results are shown in FIG. From this figure, it was found that the concentration of phosphoric acid suddenly increased at a temperature of 180 ° C. or higher at which microorganisms decompose, and was almost constant at 220 ° C. In addition, pyroglutamic acid, which is a protein-derived degradation product, and acetic acid derived from cellulose, were the main products. By using the separation / recovery method of the present invention, phosphoric acid could be selectively adsorbed and recovered.

  Further, the yield of acetic acid corresponding to the reaction time was examined. The results are shown in FIG. From this figure, it was found that a treatment of about 10 minutes was sufficient to obtain a useful organic acid.

  FIG. 1 is a diagram for explaining a process for separating phosphoric acid, amino acid, and organic acid from organic substances decomposed by subcritical water treatment, fermentation, and heated steam using the separation / recovery method of the present invention.   FIG. 2 is a diagram showing an adsorption isotherm of H3PO4 by OH-type DIAION SA10A.   FIG. 3 is a diagram showing the influence of the inlet concentration on the breakthrough curve of H3PO4 by OH-type DIAION SA10A.   FIG. 4 is a diagram showing an elution curve of H3PO4 adsorbed on the OH-type DIAION SA10A column.   FIG. 5 is a diagram showing a phosphoric acid-lactic acid binary adsorption isotherm in OH-type DIAION SA10A.   FIG. 6 is a diagram showing a phosphate-lactic acid binary component breakthrough curve and an elution curve in OH-type DIAION SA10A.   FIG. 7 is a diagram showing the pH dependence of the adsorption amounts of pyroglutamic acid and L-alanine in PEI-Ch.   FIG. 8 is a diagram showing a binary breakthrough curve and an elution curve of pyroglutamic acid and L-alanine in PEI-Ch.   FIG. 9 is a diagram showing adsorption isotherms of lactic acid and pyroglutamic acid in PEI-Ch.   FIG. 10 is a diagram showing adsorption isotherms of lactic acid and acetic acid in PEI-Ch.   FIG. 11 is a diagram showing the pH dependency of the adsorption amounts of lactic acid and acetic acid in PEI-Ch.   FIG. 12 is a diagram showing adsorption isotherms of lactic acid and formic acid in PEI-Ch.   FIG. 13 is a diagram showing the pH dependency of the adsorption amounts of lactic acid and formic acid in PEI-Ch.   FIG. 14 is a diagram showing adsorption isotherms of lactic acid and pyroglutamic acid in PEI-Ch.   FIG. 15 is a diagram showing the pH dependence of the adsorption amounts of lactic acid and pyroglutamic acid in PEI-Ch.   FIG. 16 is a diagram showing the yield of organic acid contained in the water-soluble soluble component of this decomposition product corresponding to the reaction temperature.   FIG. 17 shows the acetic acid yield corresponding to the reaction time.

Claims (9)

The liquid to be treated containing phosphoric acid is passed through a strongly basic anion exchange resin to adsorb phosphoric acid to the strongly basic anion exchange resin,
Next, a method for separating and recovering phosphoric acid, in which a sodium hydroxide aqueous solution is passed through the strongly basic anion exchange resin to desorb the phosphoric acid to recover the phosphoric acid. The liquid to be treated containing an organic acid is passed through a weakly basic anion exchange resin to adsorb the organic acid to the weakly basic anion exchange resin,
Next, a method for separating and recovering an organic acid, wherein an aqueous sodium hydroxide solution is passed through the weakly basic anion exchange resin to desorb the organic acid, thereby recovering the organic acid. A method for separating and recovering phosphoric acid and organic acid,
A liquid to be treated containing phosphoric acid and an organic acid is passed through a strongly basic anion exchange resin to adsorb phosphoric acid to the strongly basic anion exchange resin. Passing through a strongly basic anion exchange resin, desorbing the phosphoric acid, recovering the phosphoric acid,
The liquid to be treated that has passed through the strongly basic anion exchange resin is passed through a weakly basic anion exchange resin to adsorb the organic acid to the weakly basic anion exchange resin, and then an aqueous sodium hydroxide solution is added. A method for separating and recovering phosphoric acid and organic acid, which passes through the weakly basic anion exchange resin and desorbs the organic acid salt to recover the organic acid. The separation / recovery method according to claim 1,
Separation characterized in that the liquid to be treated is a food waste and garbage including sludge, fish meal, animal manure, waste wood, and organic matter including waste plastics, which are decomposed in a subcritical state.・ Recovery method. A method for separating and recovering phosphoric acid and amino acid,
A liquid to be treated containing phosphoric acid and an organic acid is passed through a strongly basic anion exchange resin to adsorb phosphoric acid to the strongly basic anion exchange resin. Passing through a strongly basic anion exchange resin, desorbing the phosphoric acid, recovering the phosphoric acid,
A method for separating and collecting phosphoric acid and organic acid, wherein amino acids are separated and collected using the liquid to be treated that has passed through the strongly basic anion exchange resin. A method for separating and collecting organic acids and amino acids,
A liquid to be treated containing an organic acid and an amino acid is passed through a weakly basic anion exchange resin to adsorb the organic acid to the weakly basic anion exchange resin, and then the aqueous sodium hydroxide solution is added to the weak aqueous anion exchange resin. Passing through a basic anion exchange resin, desorbing the organic acid, recovering the organic acid,
A method for separating and recovering phosphoric acid and organic acid, wherein amino acids are separated and recovered using the liquid to be treated that has passed through the weakly basic anion exchange resin. A method for separating and recovering phosphoric acid, organic acid and amino acid,
The liquid to be treated containing phosphoric acid, organic acid and amino acid is passed through a strongly basic anion exchange resin to adsorb phosphoric acid to the strongly basic anion exchange resin, and then an aqueous sodium hydroxide solution is added. , Passing through the strongly basic anion exchange resin, desorbing the phosphoric acid, recovering the phosphoric acid,
The liquid to be treated that has passed through the strongly basic anion exchange resin is allowed to pass through a weakly basic anion exchange resin to adsorb the organic acid to the weakly basic anion exchange resin, and then an aqueous sodium hydroxide solution Is passed through the weakly basic anion exchange resin to desorb the organic acid to recover the organic acid,
A method for separating / recovering phosphoric acid, organic acid and amino acid, wherein amino acid is separated / recovered using the liquid to be treated that has passed through the weakly basic anion exchange resin. A liquid to be treated containing two or more organic acids is passed through a weakly basic anion exchange resin to adsorb the organic acid to the weakly basic anion exchange resin. A separation / recovery method for recovering an organic acid by passing a weakly basic anion exchange resin, desorbing the organic acid,
Organic acid separation / recovery method for recovering each organic acid by adjusting the conditions for the organic acid to adsorb to the weakly basic anion exchange resin and the conditions for the organic acid to desorb from the weakly basic anion exchange resin . A liquid to be treated obtained by sublimation treatment of organic matter with subcritical water treatment, fermentation, or superheated steam, which contains phosphoric acid, amino acid, and organic acid, and passes through strongly basic anion exchange resin Then, the phosphoric acid is adsorbed on the strong basic anion exchange resin, and then the aqueous solution of sodium hydroxide is passed through the strong basic anion exchange resin to desorb the phosphoric acid, thereby Recovered,
The liquid to be treated that has passed through the strongly basic anion exchange resin is allowed to pass through a weakly basic anion exchange resin to adsorb the organic acid to the weakly basic anion exchange resin, and then an aqueous sodium hydroxide solution Is passed through the weakly basic anion exchange resin to desorb the organic acid to recover the organic acid,
A method for treating an organic substance, wherein an amino acid is separated and recovered using a liquid to be treated that has passed through the weakly basic anion exchange resin.

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