CN104557580A - Method for preparing iminodiacetic acid - Google Patents
Method for preparing iminodiacetic acid Download PDFInfo
- Publication number
- CN104557580A CN104557580A CN201510046412.3A CN201510046412A CN104557580A CN 104557580 A CN104557580 A CN 104557580A CN 201510046412 A CN201510046412 A CN 201510046412A CN 104557580 A CN104557580 A CN 104557580A
- Authority
- CN
- China
- Prior art keywords
- acid
- iminodiacetic acid
- preparation
- value
- iminodiethanoic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 19
- FUXALCGRSSRCQE-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-7-yl)ethanamine Chemical compound NCCC1=CC=CC2=C1OCC2 FUXALCGRSSRCQE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 9
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 8
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 8
- 235000011152 sodium sulphate Nutrition 0.000 claims abstract description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 239000012266 salt solution Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- PNBCICAOOHSPGU-UHFFFAOYSA-M [OH-].[Na+].N(CC#N)CC#N Chemical compound [OH-].[Na+].N(CC#N)CC#N PNBCICAOOHSPGU-UHFFFAOYSA-M 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 15
- BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 abstract description 13
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 3
- 238000004064 recycling Methods 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 abstract 1
- 239000000413 hydrolysate Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910017053 inorganic salt Inorganic materials 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- -1 pharmacy Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- KKHJQZVEUKJURX-UHFFFAOYSA-N 2-(carboxymethylamino)acetic acid;hydrochloride Chemical compound Cl.OC(=O)CNCC(O)=O KKHJQZVEUKJURX-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- JBJKVKUJDRKYKM-UHFFFAOYSA-L disodium 2-(carboxylatomethylamino)acetate hydrochloride Chemical compound Cl.[Na+].[Na+].N(CC(=O)[O-])CC(=O)[O-] JBJKVKUJDRKYKM-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for preparing iminodiacetic acid is characterized by comprising the following steps: (A), hydrolyzing iminodiacetonitrile into iminodiacetic acid disodium salt solution by virtue of sodium hydroxide; (B) adding ammonium sulfate or ammonium bisulfate into the hydrolysate to reach a certain pH value, neutralizing excessive sodium hydroxide and part of iminodiacetic acid disodium salt, and simultaneously recycling the produced ammonia so as to prepare ammonia water or liquid ammonia; and (C), adding sulfuric acid to regulate the pH value, cooling for crystallizing, separating so as to obtain iminodiacetic acid, and concentrating the filtrate to separate sodium sulfate to be used in the reaction in the next batch. The method for preparing iminodiacetic acid according to the claim 1 is characterized in that the pH value in the step (B) is 8-10. 3. The method for preparing iminodiacetic acid according to the claim 2 is characterized in that the pH value in the step (B) is 9.0-9.5. The method for preparing iminodiacetic acid according to any one of the claims 1-3 is characterized in that the pH value in the step (C) is 2.0-2.5.
Description
Technical field
The invention belongs to technical field of fine, particularly relate to a kind of preparation method of iminodiethanoic acid.
Background technology
Iminodiethanoic acid has another name called Diglycocol, aminodiacetic acid, and be called for short I DA, molecular formula is NH (CH
2cOOH)
2it is a kind of important fine chemical product, there is very strong complexing action, energy and many kinds of metal ions form inner complex, they are extensive application in agricultural chemicals, dyestuff, chemical industry, water treatment, medicine, functional polymer, electronics etc., is important source material and the intermediate of agricultural chemicals, pharmacy, rubber, tensio-active agent, complexing agent, foodstuff additive, electroplating industry, synthetic metals surface treatment agent and ion exchange resin thereof etc.
The method that domestic industryization produces iminodiethanoic acid mainly contains four kinds, iminodiacetonitrile alkali hydrolysis method, iminodiacetonitrile acid-hydrolysis method, chloroactic acid method and diethanolamine oxidation style.Wherein, chloroactic acid method is by after Mono Chloro Acetic Acid and ammoniacal liquor, calcium hydroxide reaction, with hcl acidifying, generate iminodiacetic acid hydrochlorid, leave standstill crystallization, suction filtration, pickling, be dissolved in hot water, add sodium hydroxide solution, generate iminodiethanoic acid, after crystallization, separation, drying, obtain product, the method technical maturity, but there is long flow path, the shortcoming such as product purity is low, cost is high, " three wastes " serious; Iminodiacetonitrile acid-hydrolysis method iminodiacetonitrile and hydrochloric acid or sulphuric acid hydrolysis is directly obtained iminodiethanoic acid and ammonium chloride or ammonium sulfate; Diethanolamine oxidation style and iminodiacetonitrile alkali hydrolysis method are all first raw material is become iminodiacetic acid disodium salt, then the mixture of iminodiethanoic acid and sodium-chlor or sodium sulfate is obtained with hydrochloric acid or sulfuric acid acidation, be separated and obtain iminodiethanoic acid, reaction equation is as follows:
1) iminodiacetonitrile alkali hydrolysis method
NH(CH
2CN)
2+NaOH+H
2O→NH(CH
2COONa)
2+NH
3
NH(CH
2COONa)
2+HCl→NH(CH
2COOH)
2+NaCl
Or:
NH(CH
2COONa)
2+H
2SO
4→NH(CH
2COOH)
2+Na
2SO
4
2) iminodiacetonitrile acid-hydrolysis method
NH(CH
2CN)
2+HCl+H
2O→NH(CH
2COOH)
2+NH
4Cl
NH(CH
2CN)
2+H
2SO
4+H
2O→NH(CH
2COOH)
2+(NH
4)
2SO
4
3) diethanolamine oxidation style
NH(CH
2CH
2OH)
2+NaOH→NH(CH
2COONa)
2+H
2
NH(CH
2COONa)
2+HCl→NH(CH
2COOH)
2+NaCl
Or:
NH(CH
2COONa)
2+H
2SO
4→NH(CH
2COOH)
2+Na
2SO
4
At present, after iminodiacetonitrile basic hydrolysis, acidization is the preparation method of the iminodiethanoic acid commonly used the most, conventional separation method is that iminodiacetic acid disodium salt hydrochloric acid or sulfuric acid acidation are become iminodiethanoic acid and corresponding inorganic salt, utilize that iminodiethanoic acid solubleness in water is little and the two separates by inorganic salt solubleness in water is large characteristic, mother liquor is applied mechanically continuously; Or iminodiacetic acid disodium salt acidifying is become iminodiethanoic acid one sodium salt and sodium-chlor or sodium sulfate, the dissolubility property of recycling iminodiethanoic acid one sodium salt and inorganic salt first isolates inorganic salt, acidifying is separated and obtains iminodiethanoic acid, mother liquid recycle again.Because iminodiacetonitrile hydrolyzed solution is strong basicity, reacts violent when adding the sulfuric acid acidation initial stage, discharge a large amount of heats, cause reaction local superheating, product section carbonizes, and darkens, react more difficult control, often need to add activated carbon decolorizing to improve the outward appearance of product.
Summary of the invention
In view of this, the technical problem to be solved in the present invention is the preparation method providing a kind of iminodiethanoic acid, replace part of sulfuric acid to carry out acidifying to iminodiacetonitrile alkali solution liquid with ammonium sulfate or monoammonium sulfate, ammonium sulfate low for added value or monoammonium sulfate are changed into the high ammonia of added value simultaneously.The method is simple to operate, the problem that when effectively can solve acidifying, heat release is violent.
The invention provides a kind of preparation method of iminodiethanoic acid, comprise the following steps:
A) iminodiacetonitrile sodium hydroxide hydrolysis is become iminodiacetic acid disodium salt solution;
B) in this hydrolyzed solution, add a certain amount of ammonium sulfate or monoammonium sulfate to certain pH, neutralize excessive sodium hydroxide and part iminodiacetic acid disodium salt, the ammonia simultaneously reclaiming generation makes ammoniacal liquor or liquefied ammonia;
C) add sulphur acid for adjusting pH, decrease temperature crystalline, (filtration) are separated and obtain iminodiethanoic acid, apply mechanically to lower batch of reaction after concentrated (filtration) separating sodium sulfate of filtrate.
Preferably, described step B) pH is 8-10, more excellent, pH is 9.0-9.5.
Preferably, described step C) pH is 2.0-2.5.
Experimental result shows, the present invention obtains iminodiethanoic acid purity can reach more than 99.0%, and in ammonium sulfate or monoammonium sulfate, the rate of recovery of ammonia can reach more than 90%.
Embodiment
The invention provides a kind of preparation method of iminodiethanoic acid, comprise the following steps: A) iminodiacetonitrile sodium hydroxide hydrolysis is become iminodiacetic acid disodium salt solution; B) in this hydrolyzed solution, add a certain amount of ammonium sulfate or monoammonium sulfate to certain pH, neutralize excessive sodium hydroxide and part iminodiacetic acid disodium salt, the ammonia simultaneously reclaiming generation makes ammoniacal liquor or liquefied ammonia.C) add sulphur acid for adjusting pH, decrease temperature crystalline, separation obtain iminodiethanoic acid, mother liquor concentrations separating sodium sulfate, and mother liquid recycle is to lower batch of reaction.
The restriction that the present invention is not special to the source of all raw materials, for commercially available.
In order to further illustrate the present invention, below in conjunction with embodiment, the preparation method to a kind of iminodiethanoic acid yield provided by the invention is described in detail.
Embodiment 1:
By iminodiacetonitrile (100g, 95%, 1mol) sodium hydroxide solution (585g, 15%, 2.2mol) 60-65 DEG C hydrolysis, be hydrolyzed post-heating to 100 DEG C, insulation 1h, is cooled to 60 DEG C, adds ammonium sulfate in batches and regulates pH=9.5, react the ammonia water discharged to absorb, the sulfuric acid continuing to drip 93wt% is neutralized to pH value for being 2.0, is cooled to 40 DEG C of insulation 1h, filter, filter cake 15ml water washing, dry, obtain the iminodiethanoic acid solid of white.The filtrate obtained is steamed water and is concentrated, and isolate sodium sulfate, filtrate is applied mechanically to lower batch, applies mechanically three batches continuously, and after applying mechanically, three lot data see the following form.
Embodiment 2:
By iminodiacetonitrile (100g, 95%, 1mol) sodium hydroxide solution (585g, 15%, 2.2mol) 60-65 DEG C hydrolysis, be hydrolyzed post-heating to 100 DEG C, insulation 1h, is cooled to 60 DEG C, adds monoammonium sulfate in batches and regulates pH=9.5, react the ammonia water discharged to absorb, the sulfuric acid continuing to drip 93wt% is neutralized to pH value for being 2.0, is cooled to 40 DEG C of insulation 1h, filter, filter cake 15ml water washing, dry, obtain the iminodiethanoic acid solid of white.The filtrate obtained is steamed water and is concentrated, and isolate sodium sulfate, filtrate is applied mechanically to lower batch, applies mechanically three batches continuously, and after applying mechanically, three lot data see the following form.
The above is only the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention; can also make some improvements and modifications, these improvements and modifications also should be considered as protection scope of the present invention.
Claims (4)
1. a preparation method for iminodiethanoic acid, is characterized in that, comprises the following steps:
A) iminodiacetonitrile sodium hydroxide hydrolysis is become iminodiacetic acid disodium salt solution;
B) in this hydrolyzed solution, add ammonium sulfate or monoammonium sulfate to certain pH, neutralize excessive sodium hydroxide and part iminodiacetic acid disodium salt, the ammonia simultaneously reclaiming generation makes ammoniacal liquor or liquefied ammonia;
C) add sulphur acid for adjusting pH, decrease temperature crystalline, separation obtain iminodiethanoic acid, apply mechanically to lower batch of reaction after filtrate concentrating and separating sodium sulfate.
2. the preparation method of iminodiethanoic acid as claimed in claim 1, is characterized in that, described step B) pH is 8-10.
3. the preparation method of iminodiethanoic acid as claimed in claim 2, is characterized in that, described step B) pH is 9.0-9.5.
4. the preparation method of iminodiethanoic acid as described in claim any one of claim 1-3, is characterized in that, described step C) pH is 2.0-2.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510046412.3A CN104557580B (en) | 2015-01-29 | 2015-01-29 | A kind of preparation method of iminodiacetic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510046412.3A CN104557580B (en) | 2015-01-29 | 2015-01-29 | A kind of preparation method of iminodiacetic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104557580A true CN104557580A (en) | 2015-04-29 |
| CN104557580B CN104557580B (en) | 2016-08-17 |
Family
ID=53074760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104557580B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104974054A (en) * | 2015-06-16 | 2015-10-14 | 重庆紫光化工股份有限公司 | Method and apparatus for preparing iminodiacetic acid by using iminodiacetonitrile to produce mother liquor |
| CN109369429A (en) * | 2018-12-29 | 2019-02-22 | 重庆紫光化工股份有限公司 | The device and method of iminodiacetic acid is prepared using iminodiacetonitrile feed liquid |
| CN109678742A (en) * | 2018-12-29 | 2019-04-26 | 重庆紫光化工股份有限公司 | A method of utilizing separation equipment separating iminodiacetic acid |
| CN111100022A (en) * | 2019-10-30 | 2020-05-05 | 石家庄市栾城区华英工贸有限责任公司 | Method for preparing carboxylic acid compounds by catalyzing nitrile compounds to hydrolyze with Lewis acid |
| CN115141111A (en) * | 2022-07-29 | 2022-10-04 | 苏州科熔新材料技术研究有限公司 | Technology for preparing IDA from ammonium bicarbonate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1172070A (en) * | 1997-07-11 | 1998-02-04 | 王天伦 | Method for producing ammonium sulfate by using waste ammonia water |
| CN1594281A (en) * | 2004-07-05 | 2005-03-16 | 四川省天然气化工研究院 | Process for preparing iminodiacetic acid |
| CN103265443A (en) * | 2013-06-05 | 2013-08-28 | 重庆紫光化工股份有限公司 | Industrial production method of high-purity iminodiacetic acid |
-
2015
- 2015-01-29 CN CN201510046412.3A patent/CN104557580B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1172070A (en) * | 1997-07-11 | 1998-02-04 | 王天伦 | Method for producing ammonium sulfate by using waste ammonia water |
| CN1594281A (en) * | 2004-07-05 | 2005-03-16 | 四川省天然气化工研究院 | Process for preparing iminodiacetic acid |
| CN103265443A (en) * | 2013-06-05 | 2013-08-28 | 重庆紫光化工股份有限公司 | Industrial production method of high-purity iminodiacetic acid |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104974054A (en) * | 2015-06-16 | 2015-10-14 | 重庆紫光化工股份有限公司 | Method and apparatus for preparing iminodiacetic acid by using iminodiacetonitrile to produce mother liquor |
| CN109369429A (en) * | 2018-12-29 | 2019-02-22 | 重庆紫光化工股份有限公司 | The device and method of iminodiacetic acid is prepared using iminodiacetonitrile feed liquid |
| CN109678742A (en) * | 2018-12-29 | 2019-04-26 | 重庆紫光化工股份有限公司 | A method of utilizing separation equipment separating iminodiacetic acid |
| CN109369429B (en) * | 2018-12-29 | 2021-06-01 | 重庆紫光化工股份有限公司 | Device and method for preparing iminodiacetic acid by utilizing iminodiacetonitrile feed liquid |
| CN109678742B (en) * | 2018-12-29 | 2021-07-20 | 重庆紫光化工股份有限公司 | Method for separating iminodiacetic acid by using separation equipment |
| CN111100022A (en) * | 2019-10-30 | 2020-05-05 | 石家庄市栾城区华英工贸有限责任公司 | Method for preparing carboxylic acid compounds by catalyzing nitrile compounds to hydrolyze with Lewis acid |
| CN115141111A (en) * | 2022-07-29 | 2022-10-04 | 苏州科熔新材料技术研究有限公司 | Technology for preparing IDA from ammonium bicarbonate |
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Denomination of invention: A preparation method of iminodiacetic acid Effective date of registration: 20210809 Granted publication date: 20160817 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2021500000036 |
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Denomination of invention: A kind of preparation method of iminodiacetic acid Effective date of registration: 20220811 Granted publication date: 20160817 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2022500000056 |
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Denomination of invention: A preparation method of iminodiacetic acid Effective date of registration: 20230317 Granted publication date: 20160817 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2023500000020 |