CN1805925A - Process for purification of aqueous acid solutions - Google Patents
Process for purification of aqueous acid solutions Download PDFInfo
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- CN1805925A CN1805925A CN 200580000485 CN200580000485A CN1805925A CN 1805925 A CN1805925 A CN 1805925A CN 200580000485 CN200580000485 CN 200580000485 CN 200580000485 A CN200580000485 A CN 200580000485A CN 1805925 A CN1805925 A CN 1805925A
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- acid
- aqueous solution
- processed water
- purification process
- solution
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/04—Processes using organic exchangers
Abstract
A process for the purification of aqueous acid solutions which can dispense with the step of removing chloride ions and which is reduced in the damage to an ion exchanger (such as an ion-exchange column) and thereby permits repeated use of an ion exchanger and lengthened service thereof to bring about a cut in the manufacturing cost. Specifically, a process for the purification of an aqueous solution of an acid (A) by passing an aqueous solution to be treated which contains an acid (A) and a contaminant acid (B) through an ion-exchange column filled with an anion-exchange resin having an anion adsorption selectivity between acids (A) and (B), characterized in that an aqueous solution of acid (A) having a concentration lower than that of the aqueous solution to be treated is passed through the column prior to the passing of the aqueous solution to be treated through the column.
Description
Technical field
The present invention relates to the purification process of aqueous acid, relate more specifically to remove effectively and efficiently with the isethionic acid purification process of these aqueous acids that are the contained impurity such as sulfuric acid of aqueous acids such as the hydroxyl alkansulfonic acid of representative or alkansulfonic acid.
Background technology
The aqueous solution that with the isethionic acid is the hydroxyl alkansulfonic acid of representative or alkansulfonic acid etc. is owing to contain impurity sulfuric acid in its manufacturing processed, need from the above-mentioned aqueous solution, to remove sulfuric acid all the time, but because these acid are similar to the sulfuric acid characteristic, be difficult to separate by operations such as distillations, therefore make spent ion exchange resin come from the above-mentioned processed aqueous solution, to remove sulfuric acid, for example in the patent documentation 1, use chlorine type basic anion exchange resin to remove impurity sulfuric acid contained in the aqueous methane sulfonic acid.
Yet, in this method,, from the above-mentioned aqueous acid that obtains, remove chlorion so need to use to strip to handle to wait because chlorion can be sneaked in the aqueous acid that obtains, in addition, chlorion can't be removed from the above-mentioned aqueous acid that obtains fully.
On the other hand, as the method in the aqueous acid of avoiding chlorion to sneak into obtaining, can consider to use OH type basic anion exchange resin as ion exchange resin, but if in the purifying of aqueous acid, use OH type basic anion exchange resin, then be accompanied by the temperature rising that this ion exchange resin and sour neutralization heat cause, damage for ion exchanger self and cornice, the work-ing life of ion exchanger (comprising post) is short, the cost of producing apparatus rises, the industrialization adaptability shortcoming of purifying aqueous acid.
Patent documentation 1: the Japanese Patent spy opens the 2001-64249 communique
The announcement of invention
The problem that invention will solve
Therefore, the object of the present invention is to provide unnecessary operations such as not needing to remove chlorion, and can lower the ion exchanger damage of (comprising post), reuse ion exchanger, can prolong the work-ing life of ion exchanger, reduce the purification process of the aqueous acid of manufacturing cost.
Solve the method for problem
The inventor is conscientiously research in view of the above problems, thereby finished the present invention.Promptly, the purification process of the aqueous solution of acid provided by the invention (A) be by make contain acid (A) and as the processed water solution of the acid (B) of impurity by having filled the purification process that acid (A) and sour (B) is had the aqueous solution of the acid (A) that the ion exchange tower of the anionite-exchange resin (C) of anionic adsorption selectivity carries out, it is characterized in that, pass through above-mentioned processed water solution in the aqueous solution (calling " aqueous solution of rare acid (A) " in the following text) back by the acid lower (A) than the concentration of above-mentioned processed water solution.
In above-mentioned the present invention better be: anionite-exchange resin (C) is OH type basic anion exchange resin; The acid concentration of the aqueous solution of rare acid (A) is below 30 quality %; The aqueous solution of rare acid (A) obtains by dilution processed water solution; Processed water solution be anionite-exchange resin (C) to as the saturated back of the absorption of the acid (B) of impurity from the effusive solution of ion exchange tower; The aqueous solution of rare acid (A) is after processed water solution is carried out purification process pure water to be passed through ion exchange tower and the aqueous solution of effusive acid (A); The throughput of the aqueous solution of rare acid (A) is to make the total amount of the aqueous acid medium of rare acid (A) be not less than the amount of the ion-exchange group total amount of the anionite-exchange resin (C) in the ion exchange tower; The throughput of the aqueous solution of rare acid (A) is the amount that makes the ion-exchange group total amount equivalent of the total amount of aqueous acid medium of rare acid (A) and the anionite-exchange resin (C) in the ion exchange tower; The aqueous solution of rare acid (A) and the above stream mode of processed water solution are passed through; Acid (B) is sulfuric acid, and acid (A) is alkansulfonic acid; Acid (A) is hydroxyl alkansulfonic acid, especially isethionic acid.
In addition, the purification process of the aqueous solution of isethionic acid provided by the invention is by making the purification process of the aqueous solution that contains the isethionic acid that isethionic acid and impurity vitriolic processed water solution undertakies by the ion exchange tower of having filled at isethionic acid and vitriolic OH type basic anion exchange resin, it is characterized in that, after by the aqueous solution of the isethionic acid lower, pass through above-mentioned processed water solution than the concentration of above-mentioned processed water solution.
The effect of invention
Effect of the present invention is to provide does not need to remove unnecessary operations such as chlorion, and can lower the ion exchanger damage of (comprising post), reuse ion exchanger, can prolong the work-ing life of ion exchanger, reduce the purification process of the aqueous acid of manufacturing cost.
The best mode that carries out an invention
Among the present invention, processed water solution as the purifying object, the aqueous solution that promptly contains the acid (A) of acid (B) as impurity, be not particularly limited, get final product so long as be difficult to remove the aqueous solution of the acid (A) of acid contained in the processed water solution (B), specifically can exemplify and be main component for example and contain the vitriolic aqueous solution with alkansulfonic acid or hydroxyl alkansulfonic acid as impurity with operations such as distillations.In addition, above-mentioned processed water solution in the method for the present invention of following explanation, can be anionite-exchange resin (C) to as the saturated back of the absorption of the acid (B) of impurity from the effusive solution of ion exchange tower.
The aqueous solution of above-mentioned alkansulfonic acid or hydroxyl alkansulfonic acid is because its manufacture method contains the sulfuric acid of trace as impurity, sulfuric acid and these alkansulfonic acids or hydroxyl alkansulfonic acid similar performance are difficult to by operations such as distillations above-mentioned sulfuric acid as impurity be removed from this aqueous solution.
Therefore, among the present invention in the processed water solution object lesson of the contained acid as impurity (B) can exemplify for example sulfuric acid.
The present invention contains acid (A) and comes the aqueous solution of purifying acid (A) as the processed water solution of the acid (B) of impurity by having filled the ion exchange tower that acid (A) and acid (B) are had the anionite-exchange resin (C) of anionic adsorption selectivity (that is, adsorber acid (A) is different with the ability of sour (B)) by making.That is the aqueous solution of the acid (A) that significantly reduced of the content that obtains the acid (B) in the processed water solution.
Anionite-exchange resin used in the present invention (C) is not particularly limited, so long as being had anionic adsorption selectivity, sour (A) and sour (B) can use, in order to economize the purposes such as operation that remove chlorion, better be OH type basic anion exchange resin, can use for example OH type weak base anion-exchange resin etc.More specifically, better be to use OH type weak base anion-exchange resin of selling on the market of the ダ イ ヤ イ オ Application WA-20 (trade(brand)name) of デ ユ オ ラ イ ト A-561 (trade(brand)name), Mitsubishi Chemical's system of ロ one system ア Application De Ha one ス corporate system for example and similarity etc.
Purification process of the present invention is from the work-ing life that can lower the ion exchanger damage of (comprising post), repeated use ion exchanger, prolongation ion exchanger, the aspect that reduces the manufacturing cost of purifying acid (A) aqueous solution, allowing above-mentioned processed water solution when having filled the ion exchange tower of anionite-exchange resin (C), allowing processed water solution pass through ion exchange tower again after allowing the aqueous solution of rare acid (A) by ion exchange tower earlier.
The aqueous solution of rare acid (A) is not particularly limited, and the concentration that can be for example acid (A) better is below 20 quality % below 30 quality %.If concentration surpasses the aqueous solution of the acid (A) of 30 quality %, anionite-exchange resin, particularly OH type basic anion exchange resin can react with acid (B), heat release causes phenomenons such as expansion, causes the damage of ion exchanger and post, and then shortens the life-span of device.Concentration as tartaric acid (A) is low excessively, and then the purification efficiency on the industry reduces, so better be more than 5 quality %.
The aqueous solution of rare acid (A) can be the aqueous solution of pure or highly purified acid (A), also can be the aqueous solution that dilution processed water solution obtains.In addition, as described later, the aqueous solution of rare acid (A) can be after processed water solution is carried out purification process pure water to be passed through ion exchange tower and the aqueous solution of effusive acid (A).
In the purification process of the present invention, the aqueous solution of above-mentioned rare acid (A) passes through ion exchanger with processed water solution after by ion exchanger again.
Here, the structure to the aqueous solution of purifying acid (A) among the present invention describes.With the isethionic acid in the hydroxyl alkansulfonic acid as acid (A), with sulfuric acid for example as acid (B), with as will containing of the processed water solution micro-vitriolic isethionic acid aqueous solution and describe as an example as the diluent of the processed water solution of the aqueous solution of rare acid (A), but the present invention is not limited to these examples.
At first with above-mentioned rare isethionic acid aqueous solution by having filled the ion exchange tower of anionite-exchange resin (C) with anionic adsorption selectivity, because anionite-exchange resin is to vitriolic adsorption selectivity height in sulfuric acid and the isethionic acid, therefore the ion-exchange group of the anionite-exchange resin of the importing oral-lateral in nearly ion exchange tower is replaced by sulfuric acid successively.Sulfuric acid is impurity, its amount is few, and the translational speed of isethionic acid in ion exchange tower is faster than sulfuric acid, so near the ion-exchange group introducing port, all replaced by isethionic acid up to the ion-exchange group of the spout of ion exchange tower thereafter.
At this moment, if the throughput of the aqueous solution of rare acid (A) makes the total amount of the aqueous acid medium (A) of rare acid (A) be lower than the ion-exchange group total amount of the anionite-exchange resin (C) in the ion exchange tower, then the outflow oral-lateral of ion exchange tower is remaining a not metathetical ion-exchange group, owing to can sustain damage with the sulfuric acid reaction ion exchanger etc. in the processed water solution that passes through afterwards, so better be that the throughput of setting the aqueous solution of rare acid (A) is, make the total amount of the aqueous acid medium (A) of rare acid (A) be not less than the amount of the ion-exchange group total amount of the anionite-exchange resin (C) in the ion exchange tower.Consider the purification efficiency on the industry, in allowed limits, the total amount of acid (A) can be lower than the ion-exchange group total amount slightly, and such scope is included in the above-mentioned preferred range certainly.
In addition, if rare isethionic acid aqueous solution passes through in a large number, the total amount of the isethionic acid in rare isethionic acid aqueous solution surpasses the ion-exchange group total amount of the anionite-exchange resin (C) in the ion exchange tower, then rare isethionic acid aqueous solution directly flows out outside the ion exchange tower, the industrial purification efficiency of the isethionic acid aqueous solution descends, in addition, amount by contained impurity sulfuric acid metathetical ion exchange resin also increases, be to make the amount of the ion-exchange group total amount equivalent of the interior anionite-exchange resin (C) of total amount and the ion exchange tower of aqueous acid medium of rare acid (A) so be more preferably the throughput of the aqueous solution of setting rare acid (A).Consider the purification efficiency on the industry of isethionic acid, in allowed limits, above-mentioned isethionic acid can exceed this equivalent slightly, and such scope is included in the above-mentioned preferred range certainly.
By rare isethionic acid aqueous solution is passed through, anionite-exchange resin is temporarily replaced by isethionic acid, so even also can sustain damage hardly by processed water solution anionite-exchange resin etc. afterwards.
Then, will be as processed water solution contain the vitriolic isethionic acid aqueous solution by the ion exchange tower under this state.As mentioned above, anionite-exchange resin is temporarily replaced by isethionic acid, so the isethionic acid concentration of processed water solution is not particularly limited, can be rare isethionic acid aqueous solution, also can be the isethionic acid aqueous solution of high density, the angle of the purification efficiency on the industry, better be to use the isethionic acid aqueous solution of high density, particularly, better be that concentration surpasses 30 quality %, be more preferably more than 40 quality %.The isethionic acid concentration of processed water solution does not have specific upper limit, if but the decline of the purification efficiency on the excessive concentration industry, so better be below 60 quality %.
To pass through ion exchange tower as the isethionic acid aqueous solution of processed water solution, the spout of the isethionic acid elder generation arrival ion exchange tower that translational speed is fast (at this moment, for example can know by following method, promptly measure the pH of effluent liquid, confirm that pH is below 3), so, then can obtain the few refining isethionic acid aqueous solution of sulfuric acid content if from collecting effluent liquid here.
The ion-exchange group of ion exchange resin is along with containing passing through of the vitriolic isethionic acid aqueous solution as processed water solution, replaced by sulfuric acid successively to the isethionic acid that the spout side draught invests ion exchange resin from the importing oral-lateral of ion exchange tower, so when all ion-exchange groups are replaced as sulfuric acid, can stop the collection of the isethionic acid aqueous solution.Thereby this time can learn by analyze collecting the analysis that liquid carries out sulfuric acid concentration at any time, if guarantee reproducibility with same condition, then, analyze the sulfuric acid concentration in the processed water solution, calculate the throughput of processed water solution and can know the time that collection stops by carrying out preliminary experiment.
Ion exchange resin after stopping to collect can for example by regeneration such as aqueous sodium hydroxide solutions, repeat above-mentioned operation with known method.
In purification process of the present invention, from the angle of the damage of further attenuating ion exchanger etc., processed water solution better is to pass through ion exchange tower in the mode of upper reaches (upwards flowing).
Embodiment
Below, exemplify embodiments of the invention, the present invention is further detailed, but the present invention is not limited to these embodiment.
(embodiment 1)
In the tower of the polyvinyl chloride (PVC) RESINS system of volume 31.4L (internal diameter 20cm, high 1m), pack into 25.5LOH type weak base anion-exchange resin (ロ one system ア Application De Ha one ス system, trade(brand)name: デ ユ オ ラ イ ト A-561), constitute ion exchange tower.The aqueous solution of preparing isethionic acid concentration 46 quality %, sulfuric acid concentration 1.6 quality % is as processed water solution, and the aqueous solution that this processed water solution is diluted to 2 times with pure water is as the dilution isethionic acid aqueous solution.
The above stream mode of the above-mentioned dilution isethionic acid of the 24.5L aqueous solution by above-mentioned ion exchange tower (11L/hr), is followed above stream mode by above-mentioned processed water solution (16L/hr).Mensuration is from the pH of the effluent liquid of tower, and pH is lower than 3 o'clock collection effluent liquid and analyzes, and obtaining 80kg isethionic acid concentration is refining (high purity) isethionic acid aqueous solution of 44 quality %, sulfuric acid concentration 0.0034 quality %.
Then, pass through pure water, the raffinate of the isethionic acid aqueous solution in the wash-out ion exchange tower with concurrent (flowing downward).Then,, make the ion-exchange group of ion exchange resin return to the OH type, by pure water (60L/hr), be neutral up to effluent liquid, regenerating ion exchange resin with concurrent with the aqueous sodium hydroxide solution (60L/hr) of concurrent by 1.5N.
Then, similarly repeat aforesaid operations, make the isethionic acid aqueous solution of the extremely low high density of impurity vitriolic concentration continuously, even the result does not almost change to the 75th batch of isethionic acid concentration and sulfuric acid concentration yet, obtain the 75kg high purity isethionic acid aqueous solution, the rate of recovery of the high purity isethionic acid aqueous solution that the damage of ion exchange resin causes is declined by less than 10%.
(embodiment 2)
Obtain the 80kg purified isethionic acid aqueous solution (a) similarly to Example 1 afterwards, again above-mentioned processed water solution is passed through ion exchange tower, when processed water solution amounts to by 144L as a result, the composition of finding effluent liquid be identical composition by preceding processed water solution, obtain the isethionic acid aqueous solution (b) of 78kg isethionic acid concentration 46 quality %, sulfuric acid concentration 0.95 quality % during this.Then, pass through 18L pure water (16L/hr) with concurrent, the result obtains the isethionic acid aqueous solution (c) of 22kg isethionic acid concentration 46 quality %, sulfuric acid concentration 1.6 quality %, pass through 25L pure water (16L/hr) with concurrent again, the result obtains rare isethionic acid aqueous solution (d) of 28kg isethionic acid concentration 25 quality %, sulfuric acid concentration 0.8 quality %.
So far in the operation, from the rate of recovery of calculating isethionic acid by isethionic acid total amount and above-mentioned (a)～(d) contained isethionic acid amount of ion exchange tower, the result is 99 quality %.Then,, make the ion-exchange group of ion exchange resin return to the OH type, by pure water (60L/hr), be neutral up to effluent liquid, regenerating ion exchange resin with concurrent with the aqueous sodium hydroxide solution (60L/hr) of concurrent by 1.5N.
Then, as the 2nd operation, use aforesaid operations resulting (b)～(d) and above-mentioned processed water solution, with (d), (b), (c) and the order of processed water solution pass through ion exchange tower, carry out and above-mentioned same operation, obtain 100kg isethionic acid concentration 45 quality %, the isethionic acid aqueous solution (e) of sulfuric acid concentration 0.020 quality %, 78kg isethionic acid concentration 46 quality %, the isethionic acid aqueous solution (f) of sulfuric acid concentration 0.95 quality %, again pure water is passed through ion exchange tower, obtain 22kg isethionic acid concentration 46 quality %, the isethionic acid aqueous solution (g) of sulfuric acid concentration 1.6 quality %, 28kg isethionic acid concentration 23 quality %, rare isethionic acid aqueous solution (h) of sulfuric acid concentration 0.810 quality %.In addition, the rate of recovery of isethionic acid is 99 quality %.
Then, with above-mentioned similarly regenerate after, repeat 10 times with the 2nd same operation, result and similarly obtain the isethionic acid aqueous solution (e)～(h) the 2nd time, the rate of recovery of isethionic acid all is 99 quality % in addition.
(comparative example 1)
Except not by rare isethionic acid, from the beginning by the processed water solution, carry out similarly to Example 1, the result is owing to the heating and the expansion of ion exchange resin, and the crack appears in ion exchange tower, can't carry out the purification process of processed water solution.
The possibility of utilizing on the industry
Adopt the present invention, unnecessary operations such as not needing to remove chlorion can be provided, and can lower from Ion exchanger is reused in the damage of sub-permutoid (comprising post), can prolong making of ion exchanger Use the life-span, reduce the purification process of the aqueous acid of manufacturing cost.
Claims (14)
1. the purification process of the aqueous solution of acid (A), it be make contain acid (A) and as the processed water solution of the acid (B) of impurity by having filled the purification process that acid (A) and sour (B) is had the aqueous solution of the acid (A) that the ion exchange tower of the anionite-exchange resin (C) of anionic adsorption selectivity carries out, it is characterized in that, after by the aqueous solution of the acid (A) lower, pass through above-mentioned processed water solution than the concentration of described processed water solution.
2. the purification process of the aqueous solution of acid as claimed in claim 1 (A), its feature are that also anionite-exchange resin (C) is OH type basic anion exchange resin.
3. the purification process of the aqueous solution of acid as claimed in claim 1 or 2 (A), its feature also be, than the acid concentration of the aqueous solution of the low acid of the concentration of processed water solution (A) below 30 quality %.
4. as the purification process of the aqueous solution of each the described acid (A) in the claim 1～3, its feature also is, obtains by dilution processed water solution than the aqueous solution of the low acid of the concentration of processed water solution (A).
5. as the purification process of the aqueous solution of each the described acid (A) in the claim 1～3, its feature also is, processed water solution be anionite-exchange resin (C) to as the saturated back of absorption of the acid (B) of impurity from the effusive solution of ion exchange tower.
6. as the purification process of the aqueous solution of each the described acid (A) in the claim 1～3, its feature also is, than the aqueous solution of the low acid of the concentration of processed water solution (A) be after processed water solution is carried out purification process with pure water by ion exchange tower and the aqueous solution of effusive acid (A).
7. as the purification process of the aqueous solution of each the described acid (A) in the claim 1～4, its feature also is, is to make the total amount of the aqueous acid medium of rare acid (A) be not less than the amount of the ion-exchange group total amount of the anionite-exchange resin (C) in the ion exchange tower than the throughput of the aqueous solution of the low acid of the concentration of processed water solution (A).
8. as the purification process of the aqueous solution of each the described acid (A) in the claim 1～4, its feature also is, is the amount that makes the ion-exchange group total amount equivalent of the total amount of aqueous acid medium of rare acid (A) and the anionite-exchange resin (C) in the ion exchange tower than the throughput of the aqueous solution of the low acid of the concentration of processed water solution (A).
9. as the purification process of the aqueous solution of each the described acid (A) in the claim 1～8, its feature also is, passes through than the aqueous solution and the above stream mode of processed water solution of the low acid of the concentration of processed water solution (A).
10. as the purification process of the aqueous solution of each the described acid (A) in the claim 1～9, its feature is that also acid (B) is sulfuric acid.
11. as the purification process of the aqueous solution of each the described acid (A) in the claim 1～10, its feature is that also acid (A) is alkansulfonic acid.
12. as the purification process of the aqueous solution of each the described acid (A) in the claim 1～10, its feature is that also acid (A) is the hydroxyl alkansulfonic acid.
13. the purification process of the aqueous solution of acid as claimed in claim 12 (A), its feature are that also acid (A) is isethionic acid.
14. the purification process of the aqueous solution of isethionic acid, it is the purification process that makes the aqueous solution of the isethionic acid that contains isethionic acid and undertaken by the ion exchange tower of having filled at isethionic acid and vitriolic OH type basic anion exchange resin as the vitriolic processed water solution of impurity, it is characterized in that, after by the aqueous solution of the isethionic acid lower, pass through above-mentioned processed water solution than the concentration of described processed water solution.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004126828 | 2004-04-22 | ||
| JP126828/2004 | 2004-04-22 |
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| Publication Number | Publication Date |
|---|---|
| CN1805925A true CN1805925A (en) | 2006-07-19 |
| CN100577641C CN100577641C (en) | 2010-01-06 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200580000485A Expired - Fee Related CN100577641C (en) | 2004-04-22 | 2005-04-21 | Process for purification of aqueous acid solutions |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP4758894B2 (en) |
| CN (1) | CN100577641C (en) |
| WO (1) | WO2005102993A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106458647A (en) * | 2014-06-10 | 2017-02-22 | 栗田工业株式会社 | Operating method for regeneration type ion exchange device |
| CN110776419A (en) * | 2019-11-14 | 2020-02-11 | 郑州工程技术学院 | Green and clean production process for preparing dibutyl phthalate |
| CN113045459A (en) * | 2021-03-31 | 2021-06-29 | 潜江永安药业股份有限公司 | Method for removing sulfate radical in isethionate |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI399342B (en) * | 2007-04-25 | 2013-06-21 | Tokuyama Corp | Process for the preparation of waste liquid containing tetraalkylammonium ion |
| JP5672333B2 (en) * | 2013-04-25 | 2015-02-18 | 栗田工業株式会社 | Operation method of regenerative ion exchanger |
| TWI648224B (en) * | 2014-06-13 | 2019-01-21 | 日商栗田工業股份有限公司 | Operation method of regenerative ion exchange device |
| JP6421021B2 (en) * | 2014-11-25 | 2018-11-07 | オルガノ株式会社 | Method and apparatus for purification of high concentration sulfate solution |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4041571A1 (en) * | 1990-12-22 | 1992-06-25 | Basf Ag | METHOD FOR RELEASING ORGANIC SULPHONIC ACIDS |
| JPH06184088A (en) * | 1992-12-22 | 1994-07-05 | Mitsui Toatsu Chem Inc | Method for purifying taurine by ion exchange resin |
| JP3981430B2 (en) * | 1997-01-20 | 2007-09-26 | 株式会社Ａｄｅｋａ | Process for producing pure alkanesulfonic acid |
| FR2796941B1 (en) * | 1999-07-27 | 2001-09-14 | Atofina | PURIFICATION OF ALKANESULFONIC ACIDS |
-
2005
- 2005-04-21 WO PCT/JP2005/007612 patent/WO2005102993A1/en active Application Filing
- 2005-04-21 JP JP2006519501A patent/JP4758894B2/en active Active
- 2005-04-21 CN CN200580000485A patent/CN100577641C/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106458647A (en) * | 2014-06-10 | 2017-02-22 | 栗田工业株式会社 | Operating method for regeneration type ion exchange device |
| CN106458647B (en) * | 2014-06-10 | 2020-07-24 | 栗田工业株式会社 | Method for operating regenerative ion exchanger |
| CN110776419A (en) * | 2019-11-14 | 2020-02-11 | 郑州工程技术学院 | Green and clean production process for preparing dibutyl phthalate |
| CN110776419B (en) * | 2019-11-14 | 2020-07-28 | 郑州工程技术学院 | Green and clean production process for preparing dibutyl phthalate |
| CN113045459A (en) * | 2021-03-31 | 2021-06-29 | 潜江永安药业股份有限公司 | Method for removing sulfate radical in isethionate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100577641C (en) | 2010-01-06 |
| WO2005102993A1 (en) | 2005-11-03 |
| JPWO2005102993A1 (en) | 2007-08-16 |
| JP4758894B2 (en) | 2011-08-31 |
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