CN104557580B - A kind of preparation method of iminodiacetic acid - Google Patents
A kind of preparation method of iminodiacetic acid Download PDFInfo
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- CN104557580B CN104557580B CN201510046412.3A CN201510046412A CN104557580B CN 104557580 B CN104557580 B CN 104557580B CN 201510046412 A CN201510046412 A CN 201510046412A CN 104557580 B CN104557580 B CN 104557580B
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- iminodiacetic acid
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- ammonia
- ammonium
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- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 17
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 13
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 12
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 11
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 10
- 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 9
- 230000007062 hydrolysis Effects 0.000 claims abstract description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 9
- 235000011152 sodium sulphate Nutrition 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005864 Sulphur Substances 0.000 claims abstract description 4
- 239000012266 salt solution Substances 0.000 claims abstract description 4
- 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 abstract description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 18
- BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 239000003513 alkali Substances 0.000 abstract description 5
- 239000000243 solution Substances 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 229940043237 diethanolamine Drugs 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- -1 pharmacy Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 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
- CSIFGMFVGDBOQC-UHFFFAOYSA-N 3-iminobutanenitrile Chemical compound CC(=N)CC#N CSIFGMFVGDBOQC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000013522 chelant Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 238000009713 electroplating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses the preparation method of a kind of iminodiacetic acid, comprise the following steps: A) iminodiacetonitrile sodium hydroxide hydrolysis is become iminodiacetic acid disodium salt solution；B) in this hydrolyzate, addition ammonium sulfate or ammonium hydrogen sulfate, to certain pH, neutralize NaOH and the part iminodiacetic acid disodium salt of excess, and the ammonia simultaneously reclaiming generation makes ammoniacal liquor or liquefied ammonia；C) add sulphur acid for adjusting pH, decrease temperature crystalline, isolated iminodiacetic acid, after filtrate concentrating and separating sodium sulphate, be applied to the reaction of lower batch.Replace part of sulfuric acid that iminodiacetonitrile alkali solution liquid is acidified with ammonium sulfate or ammonium hydrogen sulfate, can effectively solve the problem that during acidifying, heat release is violent, ammonium sulfate low for added value or ammonium hydrogen sulfate be changed into the ammonia that added value is high simultaneously.
Description
Technical field
The invention belongs to technical field of fine, particularly relate to the preparation method of a kind of iminodiacetic acid.
Background technology
Iminodiacetic acid has another name called Diglycocol, aminodiacetic acid, is called for short I DA, and molecular formula is NH (CH2COOH)2, it is a kind of
Important fine chemical product, has the strongest complexing, can form chelate with many kinds of metal ions, and it is in agricultural chemicals, dye
The aspect extensive application such as the process of material, chemical industry, water, medicine, functional polymer, electronics, be agricultural chemicals, pharmacy, rubber,
Surfactant, complexing agent, food additives, electroplating industry, synthesis metal conditioner and ion exchange resin thereof etc.
Important source material and intermediate.
Domestic industry metaplasia produces the method for iminodiacetic acid mainly four kinds, iminodiacetonitrile alkali hydrolysis method, iminodiacetic acid (salt)
Nitrile acid-hydrolysis method, chloroactic acid method and diethanol amine oxidizing process.Wherein, chloroactic acid method is by anti-to monoxone and ammoniacal liquor, calcium hydroxide
Ying Hou, is acidified with hydrochloric acid, generates iminodiacetic acid hydrochlorid, stands crystallization, suction filtration, pickling, is dissolved in hot water, adds
Enter sodium hydroxide solution, generate iminodiacetic acid, crystallize, separate, obtain product after drying, the method technical maturity, but
There is the shortcomings such as long flow path, product purity is low, cost is high, " three wastes " serious；Iminodiacetonitrile acid-hydrolysis method is by imino group
Diacetonitrile directly obtains iminodiacetic acid and ammonium chloride or ammonium sulfate with hydrochloric acid or sulphuric acid hydrolysis；Diethanol amine oxidizing process and
Iminodiacetonitrile alkali hydrolysis method is all first raw material to be become iminodiacetic acid disodium salt, is then acidified with hydrochloric acid or sulfuric acid and obtains
Iminodiacetic acid and sodium chloride or the mixture of sodium sulphate, then isolated iminodiacetic acid, reaction equation is as follows:
1) iminodiacetonitrile alkali hydrolysis method
NH(CH2CN)2+NaOH+H2O→NH(CH2COONa)2+NH3
NH(CH2COONa)2+HCl→NH(CH2COOH)2+NaCl
Or:
NH(CH2COONa)2+H2SO4→NH(CH2COOH)2+Na2SO4
2) iminodiacetonitrile acid-hydrolysis method
NH(CH2CN)2+HCl+H2O→NH(CH2COOH)2+NH4Cl
NH(CH2CN)2+H2SO4+H2O→NH(CH2COOH)2+(NH4)2SO4
3) diethanol amine oxidizing process
NH(CH2CH2OH)2+NaOH→NH(CH2COONa)2+H2
NH(CH2COONa)2+HCl→NH(CH2COOH)2+NaCl
Or:
NH(CH2COONa)2+H2SO4→NH(CH2COOH)2+Na2SO4
At present, after iminodiacetonitrile basic hydrolysis, acidization is the preparation method of the most commonly used iminodiacetic acid, and conventional divides
It is that iminodiacetic acid disodium salt hydrochloric acid or sulfuric acid are acidified into iminodiacetic acid and corresponding inorganic salts from method, utilizes
Iminodiacetic acid in water, solubility is little and the two is separated by characteristic that inorganic salts solubility in water is big, mother liquor is applied mechanically continuously；
Or iminodiacetic acid disodium salt is acidified into iminodiacetic acid one sodium salt and sodium chloride or sodium sulphate, recycles imino group
The dissolubility property of SDA salt and inorganic salts first isolates inorganic salts, then is acidified isolated iminodiacetic acid, mother liquor
Apply mechanically.Because iminodiacetonitrile hydrolyzate is strong basicity, when adding the sulfuric acid acidifying initial stage, reaction is acutely, discharges substantial amounts of heat
Amount, causes reaction hot-spot, and product section carbonizes, and darkens, and reacts more difficult control, often needs to add activated carbon decolorizing
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 to provide the preparation method of a kind of iminodiacetic acid, uses ammonium sulfate
Or ammonium hydrogen sulfate replaces part of sulfuric acid to be acidified iminodiacetonitrile alkali solution liquid, simultaneously by ammonium sulfate low for added value or
Ammonium hydrogen sulfate changes into the ammonia that added value is high.The method is simple to operate, can effectively solve the problem that during acidifying, heat release is violent.
The invention provides the preparation method of a kind of iminodiacetic acid, comprise the following steps:
A) iminodiacetonitrile sodium hydroxide hydrolysis is become iminodiacetic acid disodium salt solution；
B) in this hydrolyzate, a certain amount of ammonium sulfate or ammonium hydrogen sulfate are added to certain pH, the NaOH of neutralization excess and portion
Dividing iminodiacetic acid disodium salt, the ammonia simultaneously reclaiming generation makes ammoniacal liquor or liquefied ammonia；
C) adding sulphur acid for adjusting pH, decrease temperature crystalline, (filtration) isolated iminodiacetic acid, filtrate concentrates (filtration) and separates
The reaction of lower batch it is applied to after sodium sulphate.
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.
Test result indicate that, the present invention obtains iminodiacetic acid purity up to more than 99.0%, ammonia in ammonium sulfate or ammonium hydrogen sulfate
The rate of recovery up to more than 90%.
Detailed description of the invention
The invention provides the preparation method of a kind of iminodiacetic acid, comprise the following steps: A) by iminodiacetonitrile hydrogen-oxygen
Change sodium and be hydrolyzed into iminodiacetic acid disodium salt solution；B) in this hydrolyzate, a certain amount of ammonium sulfate or ammonium hydrogen sulfate are added extremely
Certain pH, neutralizes NaOH and the part iminodiacetic acid disodium salt of excess, reclaim simultaneously the ammonia of generation make ammoniacal liquor or
Liquefied ammonia.C) sulphur acid for adjusting pH, decrease temperature crystalline, isolated iminodiacetic acid, mother liquor concentrations separating sodium sulfate, mother liquor are added
It is applied to the reaction of lower batch.
The source of all raw materials is not particularly limited by the present invention, for commercially available.
In order to further illustrate the present invention, the preparation of a kind of iminodiacetic acid yield present invention provided below in conjunction with embodiment
Method is described in detail.
Embodiment 1:
By iminodiacetonitrile (100g, 95%, 1mol) sodium hydroxide solution (585g, 15%, 2.2mol) 60-65 DEG C of hydrolysis,
Being heated to 100 DEG C after having hydrolyzed, be incubated 1h, be cooled to 60 DEG C, be dividedly in some parts ammonium sulfate regulation pH=9.5, reaction discharges
Ammonia use water absorbs, and continues the sulfuric acid of dropping 93wt% and is neutralized to pH value for for 2.0, is cooled to 40 DEG C of insulation 1h, filtration,
Filter cake 15ml water washs, and is dried, and obtains the iminodiacetic acid solid of white.The filtrate obtained is steamed water and is concentrated, and isolates
Sodium sulphate, filtrate is applied to lower batch, applies mechanically three batches continuously, and after applying mechanically, three lot data see table.
Embodiment 2:
By iminodiacetonitrile (100g, 95%, 1mol) sodium hydroxide solution (585g, 15%, 2.2mol) 60-65 DEG C of hydrolysis,
Being heated to 100 DEG C after having hydrolyzed, be incubated 1h, be cooled to 60 DEG C, be dividedly in some parts ammonium hydrogen sulfate regulation pH=9.5, reaction discharges
Ammonia use water absorb, continue the sulfuric acid of dropping 93wt% and be neutralized to pH value for for 2.0, be cooled to 40 DEG C of insulation 1h, filtration,
Filter cake 15ml water washs, and is dried, and obtains the iminodiacetic acid solid of white.The filtrate obtained is steamed water and is concentrated, and isolates
Sodium sulphate, filtrate is applied to lower batch, applies mechanically three batches continuously, and after applying mechanically, three lot data see table.
The above is only the preferred embodiment of the present invention, it is noted that for those skilled in the art,
Under the premise without departing from the principles of the invention, it is also possible to make some improvements and modifications, these improvements and modifications also should be regarded as this
Bright protection domain.
Claims (3)
1. the preparation method of an iminodiacetic acid, it is characterised in that comprise the following steps:
A) iminodiacetonitrile sodium hydroxide hydrolysis is become iminodiacetic acid disodium salt solution；
B) in this hydrolyzate, ammonium sulfate or ammonium hydrogen sulfate are added to certain pH, the NaOH of neutralization excess and part imino group
Oxalic acid disodium salt, the ammonia simultaneously reclaiming generation makes ammoniacal liquor or liquefied ammonia；
C) add sulphur acid for adjusting pH, decrease temperature crystalline, isolated iminodiacetic acid, be applied to down after filtrate concentrating and separating sodium sulphate
Batch is reacted；
Described step B) pH is 8-10.
2. the preparation method of as claimed in claim 1 iminodiacetic acid, it is characterised in that described step B) pH is 9.0-9.5.
3. the preparation method of as claimed in claim 1 or 2 iminodiacetic acid, it is characterised in that described step C) pH is 2.0-2.5.
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104974054B (en) * | 2015-06-16 | 2017-12-19 | 重庆紫光化工股份有限公司 | The method and device of iminodiacetic acid is prepared using iminodiacetonitrile production mother liquor |
| 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 |
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 |
-
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 |
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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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