CN104910030A - Synthesis technology for high-purity ethanolamine aminocarboxylic chelating agent - Google Patents
Synthesis technology for high-purity ethanolamine aminocarboxylic chelating agent Download PDFInfo
- Publication number
- CN104910030A CN104910030A CN201510243980.2A CN201510243980A CN104910030A CN 104910030 A CN104910030 A CN 104910030A CN 201510243980 A CN201510243980 A CN 201510243980A CN 104910030 A CN104910030 A CN 104910030A
- Authority
- CN
- China
- Prior art keywords
- solution
- formaldehyde
- sodium cyanide
- synthesis technique
- temperature
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a synthesis technology for a high-purity ethanolamine aminocarboxylic chelating agent. The synthesis technology comprises the following steps: first, ethanolamine and water are mixed, the temperature is kept at 30-60 DEG G, formaldehyde and a sodium cyanide solution are dripped in the mixed solution slowly, and at the same time, nitrogen is blown into the mixed solution and ammonia gas is discharged; second, after dripping is finished, the temperature of the system is risen to 90-100 DEG C, thermal insulation is carried out for 1-2h, nitrogen is input, the ammonia gas is discharged continuously until thermal insulation is over; third, the solution obtained from the second step is subjected to decoloring and filtering, then the pH of the solution is adjusted to 2-5 by utilization of acid, and crystallization is carried out at a temperature of 30-60 DEG C. The synthesis technology can lower the NTA content effectively, raises the operation safety, raises the yield, shortens reaction steps and time, and lowers the reaction cost.
Description
Technical field
The present invention relates to the synthesis technique of chemical industry preparation, particularly a kind of synthesis technique of high purity ethanol amine amino carboxy chelating agent.
Background technology
Ethanolamines amino carboxy chelating agent comprises 2-hydroxyethyliminodiacetic acid sodium (HIDA) and N, N-bicine N-(DHEG), it is widely used in the extraction of rare metal, boiler, the scale removal of water pipe and the dyeing auxiliaries of phthalocyanine pigment as complexing agent, and consumption is very large.The sodium salt of HIDA is the stablizer of SYNTHETIC OPTICAL WHITNER, and at Losantin type chlorinated lime, sodium hypochlorite bleaching liquid, Sodium peroxoborate, can prevent from after adding HIDA sodium salt decomposing and release oxygen, keep satisfactory stability in the SYNTHETIC OPTICAL WHITNER such as SPC-D.DHEG can not only use as complexing agent, uses also very extensive in biological buffer simultaneously.
The current main concentration of production is in several external major company, and external production company mainly concentrates on the U.S., West Europe, Japan, and domestic manufacturer mainly concentrates on the north.
On existing market, dominating process route has three kinds, is respectively Mono Chloro Acetic Acid condensation method, sodium cyanide method, prussic acid method.Wherein condensation method raw material is cheaply easy to get, and equipment used and technique are simply, dangerous little in production process.Its shortcoming is that productive rate is low, and its productive rate is generally about 50%.Prussic acid method, yield is relatively high, but danger is comparatively large, and technical process is complicated, is not suitable for large the carrying out produced.
And sodium cyanide synthesis method has advantage clearly relative to first two method, one, technical process is simple, dangerous little; Its two, yield is high, consume raw materials cost relatively low; Existing sodium cyanide synthesis method for directly at high temperature to drip sodium cyanide and formaldehyde in thanomin, by product ammonia in reaction process can with sodium cyanide and formaldehyde reaction, cause containing a large amount of impurity NTA in final product, cause the defect that the impurity NTA of this synthesis path existence is higher.Understand from documents and materials, NTA belongs to the material of carinogenicity, and a lot of country has stopped using this material of NTA.
Summary of the invention
The present invention is directed to the problem that the NTA that exists in existing sodium cyanide synthesis method is higher, provide a kind ofly effectively can reduce NTA content, improve processing safety, yield is high, shorten reactions steps and time, the synthesis technique of the ethanolamines amino carboxy chelating agent of reduction reaction cost.
The technical scheme that the present invention solves the employing of its technical problem is:
A synthesis technique for high purity ethanol amine amino carboxy chelating agent, synthesis technique comprises the steps:
(1) thanomin mixes with water, keeps 30 ~ 60 DEG C, formaldehyde and sodium cyanide solution is slowly instilled in mixed solution, blasts nitrogen simultaneously, discharges ammonia in mixed solution;
(2) system is warming up to 90 ~ 100 DEG C after terminating by dropping, is incubated 1 ~ 2 hour, continues to blast nitrogen, discharge ammonia, stops at the end of insulation;
(3) solution that obtains of step (2) is through decolouring, after filtration, after regulating its pH to 2 ~ 5 with acid, in 30 ~ 60 DEG C of crystallizatioies;
Institute's amount of water is 1 ~ 3 times of thanomin quality;
Described thanomin is Monoethanolamine MEA BASF or diethanolamine, and the mol ratio of itself and sodium cyanide and formaldehyde is:
Monoethanolamine MEA BASF: sodium cyanide: formaldehyde=1: 1.95 ~ 2.35: 1.95 ~ 2.35;
Diethanolamine: sodium cyanide: formaldehyde=1: 0.95 ~ 1.35: 0.95 ~ 1.35.
Further, in step (1) while of formaldehyde and sodium cyanide and etc. mole to drip.Formaldehyde and the sodium cyanide solution total time slowly instilled in mixed solution is 1 ~ 3 hour, and the flow blasting nitrogen in mixed solution is 2 ~ 10 m
3/ h.
Further, the discoloring agent that step (3) described decolouring is selected is gac or hydrogen peroxide, and consumption is waits 0.1 ~ 1% of feed liquid total mass of decolouring, and bleaching time is 0.5h, and the solution obtained is colourless.
Further, the acid that step (3) acidifying is used is hydrochloric acid or sulfuric acid.
Further, pH is regulated to be 2 ~ 3 in step (3).
Further, the temperature of step (3) crystallization is 30 ~ 50 DEG C.
Reaction principle of the present invention is:
(1) HIDA synthesis
(2) DHEG synthesis
Side reaction:
note:in above equation
be NTA,
be HIDA,
be DHEG.
Beneficial effect of the present invention is:
(1) technological operation is simply controlled, by controlling raw material sodium cyanide and formaldehyde to adding speed in thanomin, can control the carrying out reacted, and being of value to the generation controlling reaction side reaction.
(2) control the temperature of reaction soln, temperature-rise period proceed step by step, in dropping process, reduce reaction soln temperature, drip row intensification again after terminating, control the generation of side reaction.
(3) while carrying out at a lower temperature reacting, in reaction soln, blast nitrogen to discharge ammonia, the ammonia concentration participating in side reaction is reduced, and then reduces the content of NTA in product.
(4) improve the security of operation, reduce production cost.
Embodiment
Below in conjunction with embodiment, technical scheme of the present invention is described further.
the detection method used in embodiment and comparative example:
(1) detection method of product titration content:
Take 1g sample (being accurate to 0.0001g), add ammonia-ammonium chloride buffer solution 10mL that 70mL water and pH are 10, after sample dissolution, add 5g/L eriochrome black T indicating liquid 5, with zinc chloride standard titration solution [
c(ZnCl)=0.1mol/L] to be titrated to solution be red-violet colour.
The massfraction of product
w, numerical value represents with " % ", calculates by formula (1):
W=
V×
c×(
M/
m)×1000×100 ……(1)
In formula (1):
v: the volume of zinc chloride standard titration solution, unit is mL;
c: the concentration of zinc chloride standard titration solution, unit mol/L;
m: the molar mass of product, unit is g/mol;
m: the quality of sample, unit is g.
(2) the HPLC detection method of NTA:
With reference to GB/T1401-1998.
the reagent used in embodiment and comparative example:
Monoethanolamine MEA BASF: solid, analytical pure; Diethanolamine: solid, analytical pure; Formaldehyde solution: analytical pure, mass concentration is 36.5%; Sodium cyanide solution: analytical pure, mass concentration is 30.2%; Water: distilled water; Nitrogen: purity is greater than 99.99%; The vitriol oil: analytical pure, massfraction is 90%; Concentrated hydrochloric acid: analytical pure, massfraction is 37%; Hydrogen peroxide: mass concentration 30%.
embodiment 1
60g Monoethanolamine MEA BASF and 60g water is added in the four-hole bottle of 500mL, in the aqueous solution of Monoethanolamine MEA BASF, formaldehyde solution 172.90g and sodium cyanide solution 343.07g is dripped with the while of grade mole at the temperature of 40 ~ 50 DEG C, drip flow for being respectively 87.16g/h and 170.40g/h, blast nitrogen ammonia excretion, nitrogen flow is 10m simultaneously
3/ h, drips after terminating and system is warming up to 90 ~ 95 DEG C, and be incubated 2h at this temperature, stops blasting nitrogen, obtain 2-hydroxyethyliminodiacetic acid sodium solution after insulation.
With gac 1g to 2-hydroxyethyliminodiacetic acid sodium solution decolouring 0.5h, then remove after gac after filtration, 2-hydroxyethyliminodiacetic acid sodium solution is warming up to 90 DEG C, adjust after pH to 2.5 in 40 DEG C of crystallizatioies with the vitriol oil.Obtain 2-hydroxyethyliminodiacetic acid sodium dry product 102.00g, its product titration content is 98.5%, and wherein NTA content (HPLC) is 0.5%, product yield 74.22%.
embodiment 2
60g Monoethanolamine MEA BASF and 60g water is added in the four-hole bottle of 500mL, in the aqueous solution of Monoethanolamine MEA BASF, drip formaldehyde solution 172.90g and sodium cyanide solution 343.07g at the temperature of 30 ~ 35 DEG C simultaneously, drip flow for being respectively 80g/h and 160g/h, blast nitrogen ammonia excretion, nitrogen flow is 5m simultaneously
3/ h, drips after terminating and system is warming up to 95 ~ 100 DEG C, and be incubated 2h at this temperature, stops blasting nitrogen, obtain 2-hydroxyethyliminodiacetic acid sodium solution after insulation.
With gac 2g to 2-hydroxyethyliminodiacetic acid sodium solution decolouring 0.5h, then remove after gac after filtration, 2-hydroxyethyliminodiacetic acid sodium solution is warming up to 90 DEG C, adjust after pH to 2.0 in 40 DEG C of crystallizatioies with concentrated hydrochloric acid.Obtain 2-hydroxyethyliminodiacetic acid sodium dry product 131.20g, its product titration content is 97.02%, and wherein NTA content (HPLC) is 1.5%, product yield 71.05%.
embodiment 3
60g Monoethanolamine MEA BASF and 100g water is added in the four-hole bottle of 500mL, at the temperature of 30 ~ 40 DEG C Monoethanolamine MEA BASF the aqueous solution in first drip sodium cyanide solution 343.07g, dropping flow is 228.71g/h, formaldehyde solution 172.90g is dripped again after sodium cyanide solution dropwises, dropping flow is 86.45g/h, start to blast nitrogen ammonia excretion when dripping sodium cyanide solution, nitrogen flow is 5m
3/ h, is warming up to 90 ~ 100 DEG C by system after twice dropping terminates, and is incubated 2h at this temperature, stops blasting nitrogen, obtain 2-hydroxyethyliminodiacetic acid sodium solution after insulation.
With gac 7g to 2-hydroxyethyliminodiacetic acid sodium solution decolouring 0.5h, then remove after gac after filtration, 2-hydroxyethyliminodiacetic acid sodium solution is warming up to 90 DEG C, adjust after pH to 3.0 in 40 DEG C of crystallizatioies with the vitriol oil.Obtain 2-hydroxyethyliminodiacetic acid sodium dry product 135.21g, its product titration content is 95.50%, and wherein NTA content (HPLC) is 3.0%, product yield 66.32%.
embodiment 4
60g Monoethanolamine MEA BASF and 60g water is added in the four-hole bottle of 500mL, in the aqueous solution of Monoethanolamine MEA BASF, formaldehyde solution 172.90g and sodium cyanide solution 343.07g is dripped with the while of grade mole at the temperature of 50 ~ 60 DEG C, dropping flow is 87.16g/h and 170.40g/h, blast nitrogen ammonia excretion, nitrogen flow is 3m simultaneously
3/ h, drips after terminating and system is warming up to 95 ~ 100 DEG C, and be incubated 2h at this temperature, stops blasting nitrogen, obtain 2-hydroxyethyliminodiacetic acid sodium solution after insulation.
With gac 3g to 2-hydroxyethyliminodiacetic acid sodium solution decolouring 0.5h, then remove after gac after filtration, 2-hydroxyethyliminodiacetic acid sodium solution is warming up to 90 DEG C, adjust after pH to 2.0 in 50 DEG C of crystallizatioies with concentrated hydrochloric acid.Obtain 2-hydroxyethyliminodiacetic acid sodium dry product 148.60g, its product titration content is 98.50%, and wherein NTA content (HPLC) is 0.5%, product yield 83.88%.
embodiment 5
103g diethanolamine and 100g water is added in the four-hole bottle of 500mL, in the aqueous solution of diethanolamine, formaldehyde solution 91.66g and sodium cyanide solution 179.66g is dripped with the while of grade mole at the temperature of 50 ~ 60 DEG C, drip flow and be respectively 61.11g/h and 119.77g/h, blast nitrogen ammonia excretion, nitrogen flow is 2m simultaneously
3/ h, drips after terminating and system is warming up to 95 ~ 100 DEG C, and be incubated 1h at this temperature, stops blasting nitrogen, obtain N, N-bicine N-sodium solution after insulation.
With gac to N, N-bicine N-sodium solution decolouring 0.5h, then remove after gac after filtration, N, N-bicine N-sodium solution is warming up to 90 DEG C, adjust after pH to 2.0 in 40 DEG C of crystallizatioies with the vitriol oil.Obtain N, N-bicine N-sodium dry product 137.31g, its product titration content is 99.05%, and wherein NTA content (HPLC) is 0.3%, product yield 85.00%.
embodiment 6
103g diethanolamine and 100g water is added in the four-hole bottle of 500mL, in the aqueous solution of diethanolamine, drip formaldehyde solution 100g and sodium cyanide solution 196g at the temperature of 50 ~ 60 DEG C simultaneously, drip flow and be respectively 100g/h and 196g/h, blast nitrogen ammonia excretion, nitrogen flow is 2m simultaneously
3/ h, drips after terminating and system is warming up to 95 ~ 100 DEG C, and be incubated 1h at this temperature, stops blasting nitrogen, obtain N, N-bicine N-sodium solution after insulation.
With hydrogen peroxide 10g to N, N-bicine N-sodium solution decolouring 0.5h, more after filtering, N, N-bicine N-sodium solution is warming up to 90 DEG C, adjusts after pH to 2.5 in 30 DEG C of crystallizatioies with the vitriol oil.Obtain N, N-bicine N-sodium dry product 142.48g, its product titration content is 98.85%, and wherein NTA content (HPLC) is 0.5%, product yield 86.01%.
embodiment 7
103g diethanolamine and 100g water is added in the four-hole bottle of 500mL, at the temperature of 50 ~ 60 DEG C Monoethanolamine MEA BASF the aqueous solution in first drip sodium cyanide solution 196g, dripping flow is 130.67 g/h, after sodium cyanide solution dropwises, drip formaldehyde solution 100g again, dripping flow is 100 g/h, and start to blast nitrogen ammonia excretion when dripping sodium cyanide solution, nitrogen flow is 3m
3/ h, is warming up to 95 ~ 100 DEG C by system after twice dropping terminates, and is incubated 1h at this temperature, stops blasting nitrogen, obtain N, N-bicine N-sodium solution after insulation.
With gac 3g to N, N-bicine N-sodium solution decolouring 0.5h, then remove after gac after filtration, N, N-bicine N-sodium solution is warming up to 90 DEG C, adjust after pH to 3.0 in 50 DEG C of crystallizatioies with the vitriol oil.Obtain N, N-bicine N-sodium dry product 119.61g, its product titration content is 96.53%, and wherein NTA content (HPLC) is 2.5%, product yield 70.51%.
comparative example 1
60g Monoethanolamine MEA BASF and 100g water is added in the four-hole bottle of 500mL, in the aqueous solution of Monoethanolamine MEA BASF, drip formaldehyde solution 172.90g and sodium cyanide solution 343.07g at the temperature of 90 ~ 100 DEG C simultaneously, drip flow and be respectively 86.45g/h and 171.54g/h, be incubated 2h at this temperature after dropping terminates, obtain 2-hydroxyethyliminodiacetic acid sodium solution.
With gac 5g to 2-hydroxyethyliminodiacetic acid sodium solution decolouring 0.5h, then remove after gac after filtration, 2-hydroxyethyliminodiacetic acid sodium solution is warming up to 90 DEG C, adjust after pH to 2.5 in 40 DEG C of crystallizatioies with the vitriol oil.Obtain 2-hydroxyethyliminodiacetic acid sodium dry product 148.60g, its product titration content is 94%, and wherein NTA content (HPLC) is 5.0%, product yield 70.05%.
comparative example 2
103g diethanolamine and 100g water is added in the four-hole bottle of 500mL, in the aqueous solution of diethanolamine, drip formaldehyde solution 91.66g and sodium cyanide solution 179.66g at the temperature of 95 ~ 100 DEG C simultaneously, drip flow and be respectively 61.11g/h and 119.77g/h, 1h is incubated at this temperature after dropping terminates, obtain N, N-bicine N-sodium solution.
With gac 3g to N, N-bicine N-sodium solution decolouring 0.5h, then remove after gac after filtration, N, N-bicine N-sodium solution is warming up to 90 DEG C, adjust after pH to 2.0 in 40 DEG C of crystallizatioies with the vitriol oil.Obtain N, N-bicine N-sodium dry product 137.31g, its product titration content is 95.05%, and wherein NTA content (HPLC) is 4.5%, product yield 85.00%.
According to the above embodiments, the present invention is described in detail.It should be noted that, above embodiment is just to illustrating invention.Under the prerequisite not departing from spirit of the present invention and essence, those skilled in the art can design multiple alternative of the present invention and improvement project, and it all should be understood to be within protection scope of the present invention.
Claims (6)
1. a synthesis technique for high purity ethanol amine amino carboxy chelating agent, is characterized in that, synthesis technique comprises the steps:
(1) thanomin mixes with water, keeps 30 ~ 60 DEG C, formaldehyde and sodium cyanide solution is slowly instilled in mixed solution, blasts nitrogen simultaneously, discharges ammonia in mixed solution;
(2) system is warming up to 90 ~ 100 DEG C after terminating by dropping, is incubated 1 ~ 2 hour, continues to blast nitrogen, discharge ammonia, stops at the end of insulation;
(3) solution that obtains of step (2) is through decolouring, after filtration, after regulating its pH to 2 ~ 5 with acid, in 30 ~ 60 DEG C of crystallizatioies;
Institute's amount of water is 1 ~ 3 times of thanomin quality;
Described thanomin is Monoethanolamine MEA BASF or diethanolamine, and the mol ratio of itself and sodium cyanide and formaldehyde is:
Monoethanolamine MEA BASF: sodium cyanide: formaldehyde=1: 1.95 ~ 2.35: 1.95 ~ 2.35;
Diethanolamine: sodium cyanide: formaldehyde=1: 0.95 ~ 1.35: 0.95 ~ 1.35.
2. synthesis technique according to claim 1, is characterized in that, in step (1) while of formaldehyde and sodium cyanide and etc. mole to drip.
3. synthesis technique according to claim 1 and 2, is characterized in that, the discoloring agent that step (3) described decolouring is selected is gac or hydrogen peroxide.
4. synthesis technique according to claim 3, is characterized in that, step (3) acidifying acid used is hydrochloric acid or sulfuric acid.
5. synthesis technique according to claim 4, is characterized in that, regulates pH to be 2 ~ 3 in step (3).
6. synthesis technique according to claim 5, is characterized in that, the temperature of step (3) crystallization is 30 ~ 50 DEG C.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510243980.2A CN104910030B (en) | 2015-05-14 | 2015-05-14 | A kind of synthesis technique of high purity ethanol amine amino carboxy chelating agent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510243980.2A CN104910030B (en) | 2015-05-14 | 2015-05-14 | A kind of synthesis technique of high purity ethanol amine amino carboxy chelating agent |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104910030A true CN104910030A (en) | 2015-09-16 |
CN104910030B CN104910030B (en) | 2018-03-23 |
Family
ID=54079535
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510243980.2A Active CN104910030B (en) | 2015-05-14 | 2015-05-14 | A kind of synthesis technique of high purity ethanol amine amino carboxy chelating agent |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104910030B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105646254A (en) * | 2016-02-02 | 2016-06-08 | 石家庄杰克化工有限公司 | Novel continuous automated reaction process for preparing aminopolycarboxylic acids chelating agent |
CN110256266A (en) * | 2019-05-17 | 2019-09-20 | 佳化化学科技发展(上海)有限公司 | A kind of preparation method and detection method of hydroxyethyliminodiacetic acid disodium |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4115634A (en) * | 1976-12-01 | 1978-09-19 | Air Products & Chemicals, Inc. | Amine salts of amino acids as delayed action catalysts |
WO1991003200A1 (en) * | 1989-08-28 | 1991-03-21 | The General Hospital Corporation | Hydroxy-aryl metal chelates for diagnostic nmr imaging |
DE4211713A1 (en) * | 1992-04-08 | 1993-10-14 | Basf Ag | New amino di:carboxylic-N,N-di:acetic acid deriv., useful as complexing agents - is prepd. from amino di:carboxylic acids, formaldehyde and hydrocyanic acid, or alkali metal cyanide, with amino di:carboxylic acid-N,N-di:acetonitrile as intermediate |
WO2000069807A1 (en) * | 1999-05-19 | 2000-11-23 | The Dow Chemical Company | Process for purifying aqueous tertiary amine and alkanolamine solutions |
EP1661961A2 (en) * | 2004-11-26 | 2006-05-31 | Fuji Photo Film Co., Ltd. | Metal polishing composition and method of polishing using the same |
JP2008066588A (en) * | 2006-09-08 | 2008-03-21 | Fujifilm Corp | Polishing solution |
CN102906062A (en) * | 2010-05-21 | 2013-01-30 | 陶氏环球技术有限责任公司 | Aminocarboxylate powders with improved purity and flow ability properties |
-
2015
- 2015-05-14 CN CN201510243980.2A patent/CN104910030B/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4115634A (en) * | 1976-12-01 | 1978-09-19 | Air Products & Chemicals, Inc. | Amine salts of amino acids as delayed action catalysts |
WO1991003200A1 (en) * | 1989-08-28 | 1991-03-21 | The General Hospital Corporation | Hydroxy-aryl metal chelates for diagnostic nmr imaging |
DE4211713A1 (en) * | 1992-04-08 | 1993-10-14 | Basf Ag | New amino di:carboxylic-N,N-di:acetic acid deriv., useful as complexing agents - is prepd. from amino di:carboxylic acids, formaldehyde and hydrocyanic acid, or alkali metal cyanide, with amino di:carboxylic acid-N,N-di:acetonitrile as intermediate |
WO2000069807A1 (en) * | 1999-05-19 | 2000-11-23 | The Dow Chemical Company | Process for purifying aqueous tertiary amine and alkanolamine solutions |
EP1661961A2 (en) * | 2004-11-26 | 2006-05-31 | Fuji Photo Film Co., Ltd. | Metal polishing composition and method of polishing using the same |
JP2008066588A (en) * | 2006-09-08 | 2008-03-21 | Fujifilm Corp | Polishing solution |
CN102906062A (en) * | 2010-05-21 | 2013-01-30 | 陶氏环球技术有限责任公司 | Aminocarboxylate powders with improved purity and flow ability properties |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105646254A (en) * | 2016-02-02 | 2016-06-08 | 石家庄杰克化工有限公司 | Novel continuous automated reaction process for preparing aminopolycarboxylic acids chelating agent |
CN110256266A (en) * | 2019-05-17 | 2019-09-20 | 佳化化学科技发展(上海)有限公司 | A kind of preparation method and detection method of hydroxyethyliminodiacetic acid disodium |
CN110256266B (en) * | 2019-05-17 | 2022-06-28 | 佳化化学科技发展(上海)有限公司 | Preparation method and detection method of hydroxyethyl iminodiacetic acid disodium salt |
Also Published As
Publication number | Publication date |
---|---|
CN104910030B (en) | 2018-03-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104262391B (en) | A kind of environment friendly clean producing method of high-purity glufosinate-ammonium | |
CN105461579B (en) | A kind of preparation method of iminodisuccinic acid and its salt | |
CN102477493B (en) | Silicon-removing phosphorus-removing purifying method of sodium-modified vanadium-extraction leachate | |
FR2940282B1 (en) | METHOD FOR AMMONOLYSIS OF 11-BROMOUNDECANOIC ACID | |
CN107641714B (en) | Wet recovery processing method for lead-containing raw material | |
CN102304294B (en) | High water-solubility optical bleaching agent with bactericidal effect as well as synthesis method and application thereof | |
CN101939292A (en) | Methods for salt production | |
CN109369428A (en) | A kind of preparation method of green chelating agent methylglycine diacetic acid trisodium | |
US8454929B2 (en) | Continuous process for preparation of calcium thiosulfate liquid solution | |
CN104910030A (en) | Synthesis technology for high-purity ethanolamine aminocarboxylic chelating agent | |
CN102311657B (en) | Low-water-solubility fluorescent whitening agent with bactericidal action as well as synthesis method and application thereof | |
CN105985251B (en) | A kind of amino acids process for cleanly preparing such as iminodiacetic acid | |
CN110241270A (en) | A kind of amination modified glycosyl aldehyde tanning agent and preparation method thereof | |
US6121444A (en) | Process for preparing substituted 4,4'-diaminostilbene-2,2'-disulphonic acid salts | |
CN109400492B (en) | Preparation method of tetrasodium aspartate diacetate | |
CN105541673A (en) | Method for achieving pipe-type continuous production of CLT acid nitride | |
CN105541667A (en) | Method for producing CLT acid nitride in continuous pipelization mode | |
CN105541904B (en) | A kind of purification process of glufosinate-ammonium | |
CN105541668A (en) | Method for achieving pipe-type continuous production of CLT acid chloride | |
CN108456202B (en) | Preparation method of azilsartan with low amide impurity content | |
CN108623487A (en) | A kind of preparation method of chelating agent N, N`- ethylenediamine disuccinic acid sodium salt | |
CN101298439B (en) | Fluorescent whitening agent containing 2,5-disulfonic aniline group quaternary ammonium salt, synthesis and use thereof | |
CN101307031A (en) | Amino-chloro-benzene-containing quaternary ammonium salt type fluorescent whitener, synthesizing method thereof and applications | |
CN110343053A (en) | A kind of preparation method of ultraviolet absorbing agent | |
CN105669742B (en) | A kind of purification process of glufosinate-ammonium |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |