CN106883264A - A kind of preparation method of PMIDA - Google Patents
A kind of preparation method of PMIDA Download PDFInfo
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- CN106883264A CN106883264A CN201710269433.0A CN201710269433A CN106883264A CN 106883264 A CN106883264 A CN 106883264A CN 201710269433 A CN201710269433 A CN 201710269433A CN 106883264 A CN106883264 A CN 106883264A
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- pmida
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- celsius
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- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 21
- BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 claims abstract description 17
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 238000011049 filling Methods 0.000 claims abstract description 5
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 4
- HAXVIVNBOQIMTE-UHFFFAOYSA-L disodium;2-(carboxylatomethylamino)acetate Chemical compound [Na+].[Na+].[O-]C(=O)CNCC([O-])=O HAXVIVNBOQIMTE-UHFFFAOYSA-L 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 48
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 15
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 12
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 239000005562 Glyphosate Substances 0.000 description 4
- 238000010923 batch production Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- -1 formaldehyde iminodiacetonitrile Chemical compound 0.000 description 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 4
- 229940097068 glyphosate Drugs 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- TXSYUHBFRFALGY-UHFFFAOYSA-N 2-(cyanomethylamino)acetonitrile Chemical compound N#CCNCC#N.N#CCNCC#N TXSYUHBFRFALGY-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 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
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation method of PMIDA, the problem that environmental protection pressure in the prior art is big, production efficiency is low is which solved.The present invention is obtained Iminodiacetic acid sodium salt first with iminodiacetonitrile as raw material through tubular reactor serialization alkaline hydrolysis, and reaction solution is received in reception kettle；To phosphorous acid, hydrochloric acid, formaldehyde in the reception kettle for filling first step reaction solution, is added, control temperature prepares PMIDA in 100° centigrade~180 degree, receives kettle and keeps 120 degree of backflows Celsius；Reaction solution is cooled to 80 degree Celsius, and regulation pH value is 0~1 scope, obtains finished product.The method can be widely used in the preparation field of PMIDA.
Description
Technical field
The present invention relates to pesticide synthesis technical field, specifically a kind of preparation method of PMIDA.
Background technology
PMIDA abbreviation PMIDA, molecular formula C5H10NO7P, molecular weight 227.1.PMIDA is mainly used in a series of herbicides
And the intermediate raw material of other chemical products, especially as the important intermediate of domestic and international large-tonnage pesticide herbicide glyphosate,
And glyphosate is then a kind of interior suction, low toxicity, low-residual, the efficient, herbicide of wide spectrum, security is had more than other agricultural chemicals, it is wide
It is general for numerous crops such as corn, cotton, soybean, wheat and other plants.
For many years, glyphosate occupies the first place of world pesticide sales volume always.The most common synthesis side of synthesis of glyphosate
Method, has two methods of glycine method and IAD methods to produce, and glycine method generation waste water is more, and environmental protection pressure is larger, generation
Byproduct chloromethane needs to recycle, and current China mainly uses this technique, accounts for 70%.IAD methods synthesis PMIDA has useless
Water is small the characteristics of do not have by-product, and the later stage mainly uses this route, but the technique is batch process production, and the cycle is long,
30 hours one-pot cycles；Energy resource consumption is high, 2 tons of product needed distilled water per ton；Low production efficiency, single production capacity is less than every
It 2 tons.
The Chinese invention patent application of Application No. CN200810204322.2 discloses continuous processing production imino-diacetic
The method of acetonitrile, solves some drawbacks of Batch Process, but the patent still with reactor fractional order reaction, with continuous pipe type
Reactor is compared, and production efficiency is also not reaching to highest, and is condensed no continuous processing.
The content of the invention
The present invention is exactly for big, the low problem of production efficiency, there is provided that solves environmental protection pressure in the prior art
Plant the industrialized process for preparing of production efficiency continuous PMIDA high and free from environmental pollution.
The present invention provides a kind of industrialized process for preparing of PMIDA, and it comprises the following steps：
The first step：With iminodiacetonitrile as raw material, iminodiacetic acid two is obtained through tubular reactor serialization alkaline hydrolysis
Sodium, reaction solution is received in reception kettle；
The preferred technical scheme of this step, iminodiacetonitrile is in molar ratio 1 with liquid caustic soda:2.2 ratio enters simultaneously
Continuous tubular reactor successive reaction, is 40~80 DEG C by heat exchanger controlling reaction temperature, carries out successive reaction, preferably 40~
50℃。
The preferred technical scheme of this step, course of reaction releases ammonia, and after reaction solution is received in reception kettle, ammonia is pumped to
Absorption plant enters water-filling absorption.
This step can obtain the ammoniacal liquor that content is 25%, as byproduct, than the ammoniacal liquor purity that batch process production absorbs
Height, can be used for the production of other products directly as raw material.
Because flow reactor reaction speed is fast, this step is it is possible to prevente effectively from the polymerization of iminodiacetonitrile, improves
Product quality, it is to avoid the generation of impurity, while improve yield.
Second step：To in the reception kettle for filling first step reaction solution, phosphorous acid, hydrochloric acid are added, be well mixed, add first
Aldehyde, stirs, and mixed liquor enters heat exchanger, and control temperature is continuous into tubular reactor in 80 degree~180 degree scope Celsius
Reaction, prepares the solution containing PMIDA, and the solution is received in reception kettle, receives kettle and keeps 120 degree of backflows Celsius；
Condensation reaction
Iminodiacetonitrile, phosphorous acid, hydrochloric acid and formaldehyde, are pressed 1 by the preferred technical scheme of this step:(1~1.2):(2
~2.5):The ratio of (1~1.7) mol ratio is reacted into continuous tubular reactor continuous condensating, is adjusted using heat exchanger and reacted
Temperature is in 120 degree Celsius~130 degree scopes, it is ensured that the temperature of successive reaction, stability of flow.
3rd step：By second step gained reaction solution, 80 degree Celsius are cooled to, regulation pH value is 0~1 scope, is cooled to and takes the photograph
20~30 degree of family name, filtering, obtains finished product.
The preferred pH value of this step is 0.2~0.6 scope.
The flow reactor that this technique is used can be tubular type, or other nanoscale flow reactors.
Compared with prior art, present invention process is rationally, simple to operate, and continuous alkaline hydrolysis solution system is carried out to iminodiacetonitrile
Iminodiacetonitrile, it is to avoid the generation of impurity, while improve yield.Obtained with phosphorous acid, formaldehyde successive reaction again
Product yield and purity are high, and production efficiency is high, reduce cost of labor, reduce steam consumption more than 30%, and with significant
Production capacity advantage and product quality advantage.This step can obtain the ammoniacal liquor that content is 25%, as byproduct, be produced than batch process
The ammoniacal liquor purity of absorption is high, and the production of other products can be used for directly as raw material.
Brief description of the drawings
Fig. 1 is PMIDA preparation flow schematic diagram of the present invention.
Specific embodiment
According to following embodiments, the present invention may be better understood.However, as it will be easily appreciated by one skilled in the art that real
Apply the content described by example and be merely to illustrate the present invention, without should also without limitation on this hair described in claims
It is bright.Temperature mentioned in the present invention, such as without indicating, is degree Celsius.
Embodiment 1
(1) first, to putting into 320 kg of water in dissolution kettle and starting stirring, load weighted iminodiacetic acid (salt) is then put into
Nitrile 200kg.Control temperature after stirring 30 minutes, is transferred to iminodiacetonitrile solution head tank at 40 DEG C.
(2) liquid caustic soda of the mass percent concentration 32% of 534kg is put into liquid caustic soda measuring tank.
(3) above two material is first pressed into iminodiacetonitrile：NaOH=1:2.2 mol ratio ratios enter continuous anti-
Answer device successive reaction.
(4) reaction solution continuously enters reception kettle, reacts the ammonia for producing and enters absorption plant, and reaction terminates insulation reaction 2
Hour.
(5) 80 degree Celsius are warmed up to, vacuum distillation ammonia steams 150 kilograms of ammoniacal liquor.
(6) 65 degree Celsius are cooled to, adds 550 kilograms of hydrochloric acid, 185 kilograms of phosphorous acid to stir.
(7) and then by above-mentioned mixed liquor and 370 kilograms of formaldehyde iminodiacetonitrile is pressed：Formaldehyde=1:1 mol ratio enters changes
Hot device temperature is maintained at 120 degree Celsius, into flow reactor successive reaction.The reaction solution of flow reactor falls into reception kettle,
Keep 120 degree of backflows Celsius, preserving heat after reaction ends 2 hours.
(8) 80 degree are cooled to, adds liquid caustic soda to neutralize, regulation pH value is 0.1, cools to 20~30 degree Celsius, is filtrated to get
435 kilograms of PMIDA, yield 92.19%, purity 98.29%.
Embodiment 2
(1) first, to putting into 320 kg of water in dissolution kettle and starting stirring, load weighted iminodiacetic acid (salt) is then put into
Nitrile 200kg.Control temperature after stirring 30 minutes, is transferred to iminodiacetonitrile solution head tank at 50 DEG C.
(2) in the liquid caustic soda of liquid caustic soda measuring tank input 538kg mass percent concentrations 32%.
(3) above two material is first pressed into iminodiacetonitrile：NaOH=1:2.2 mol ratios enter flow reactor
Successive reaction, heat exchanger controls temperature at 50 degree Celsius.
(4) reaction solution continuously enters reception kettle, and ammonia enters absorption plant, and reaction terminates insulation reaction 2 hours.
(5) 80 degree of vacuum distillation ammonias Celsius are warmed up to, 150 kilograms of ammoniacal liquor is steamed.
(6) 65 degree Celsius are cooled to.1 is pressed by iminodiacetonitrile, phosphorous acid, hydrochloric acid:1.2:2.5 mol ratios add hydrochloric acid
And phosphorous acid, stir.
(7) and then by upper reaction solution and 370 kilograms of formaldehyde iminodiacetonitrile is pressed：Formaldehyde=1:1.7 mol ratios enter changes
Hot device temperature is maintained at 130 degree Celsius, into flow reactor successive reaction.Reaction solution falls into reception kettle, keeps Celsius 120 degree
Backflow, preserving heat after reaction ends 2 hours.
(8) 80 degree are cooled to, adds liquid caustic soda to neutralize, regulation pH value is 0.6, cools to 20~30 degree Celsius, is filtrated to get
432 kilograms of PMIDA, yield 91.96%, purity 98.03%.
Embodiment 3
(1) first, to putting into 320 kg of water in dissolution kettle and starting stirring, load weighted iminodiacetic acid (salt) is then put into
Nitrile 200kg.Control temperature after stirring 30 minutes, is transferred to iminodiacetonitrile solution head tank at 60 DEG C Celsius.
(2) in the liquid caustic soda of liquid caustic soda measuring tank input 530kg mass percent concentrations 32%.
(3) first by above two material 1:2.2 mol ratios enter flow reactor successive reaction, and heat exchanger control temperature is taken the photograph
40~50 degree of family name.
(4) reaction solution continuously enters reception kettle, and ammonia enters absorption plant, and reaction terminates insulation reaction 2 hours.
(5) 80 degree of vacuum distillation ammonias Celsius are warmed up to, 150 kilograms of ammoniacal liquor is steamed.
(6) 65 degree Celsius are cooled to.1 is pressed by iminodiacetonitrile, phosphorous acid, hydrochloric acid:1:2 mol ratios add hydrochloric acid and Asia
Phosphoric acid, stirs.
(7) and then by upper reaction solution and 370 kilograms of formaldehyde iminodiacetonitrile is pressed：Formaldehyde=1:1.5 mol ratios enter changes
Hot device temperature is maintained at 80 degree Celsius, into flow reactor successive reaction.Reaction solution falls into reception kettle, keeps Celsius 120 degree
Backflow, preserving heat after reaction ends 2 hours.
(8) 80 degree Celsius are cooled to, adds liquid caustic soda to neutralize, regulation pH value is 0.5, cool to 20~30 degree Celsius, filtering
Obtain 433 kilograms of PMIDA, yield 91.77%, purity 98.12%.
Embodiment 4
(1) first, to putting into 320 kg of water in dissolution kettle and starting stirring, load weighted iminodiacetic acid (salt) is then put into
Nitrile 200kg.Control temperature after stirring 30 minutes, is transferred to iminodiacetonitrile solution head tank at 80 DEG C Celsius.
(2) in the liquid caustic soda of liquid caustic soda measuring tank input 530kg mass percent concentrations 32%.
(3) first by above two material 1:2.2 mol ratios enter flow reactor successive reaction, and heat exchanger control temperature is taken the photograph
40~50 degree of family name.
(4) reaction solution continuously enters reception kettle, and ammonia enters absorption plant, and reaction terminates insulation reaction 2 hours.
(5) 80 degree of vacuum distillation ammonias are warmed up to, 150 kilograms of ammoniacal liquor is steamed.
(6) 65 degree Celsius are cooled to.1 is pressed by iminodiacetonitrile, phosphorous acid, hydrochloric acid:1.1:2.3 mol ratios add hydrochloric acid
And phosphorous acid, stir.
(7) and then by upper reaction solution and 370 kilograms of formaldehyde iminodiacetonitrile is pressed：Formaldehyde=1:1.2 mol ratios enter changes
Hot device temperature is maintained at 180 degree, into flow reactor successive reaction.Reaction solution falls into reception kettle, is kept for 120 degree Celsius return
Stream, preserving heat after reaction ends 2 hours.
(8) 80 degree Celsius are cooled to, adds liquid caustic soda to neutralize, regulation pH value is 1, cools to 20~30 degree Celsius, is filtered
To 433 kilograms of PMIDA, yield 90.73%, purity 98.09%.
Claims (7)
1. a kind of preparation method of PMIDA, it is characterized in that, comprise the following steps：
The first step：With iminodiacetonitrile as raw material, Iminodiacetic acid sodium salt is obtained through tubular reactor serialization alkaline hydrolysis, instead
Liquid is answered to be received in reception kettle；
Second step：To in the reception kettle for filling first step reaction solution, phosphorous acid, hydrochloric acid are added, be well mixed, add formaldehyde, stirred
Mix uniform, mixed liquor enters heat exchanger, control temperature for 80 degree~180 degree Celsius, into tubular reactor successive reaction, prepare
Solution containing PMIDA, the solution is received in reception kettle, receives kettle and keeps 120 degree of backflows Celsius；
3rd step：By second step gained reaction solution, 80 degree Celsius are cooled to, regulation pH value is 0~1 scope, is cooled to Celsius 20
~30 degree, filtering obtains finished product.
2. the preparation method of PMIDA according to claim 1, it is characterised in that the first step iminodiacetonitrile with
Liquid caustic soda is in molar ratio 1:2.2 ratio enters continuous tubular reactor successive reaction simultaneously, and reaction temperature is controlled by heat exchanger
Spend for 40~80 degree Celsius carry out successive reaction.
3. the preparation method of PMIDA according to claim 1, it is characterised in that the first step is by heat exchanger control
Reaction temperature is 40~50 degree Celsius.
4. the preparation method of PMIDA according to claim 1, it is characterised in that the first step course of reaction releases ammonia
Gas, after reaction solution is received in reception kettle, ammonia is pumped to absorption plant and enters water-filling absorption.
5. the preparation method of PMIDA according to claim 1, it is characterised in that the second step iminodiacetonitrile,
Phosphorous acid, hydrochloric acid and formaldehyde press 1:(1~1.2):(2~2.5):The ratio of (1~1.7) mol ratio enters continuous tubular reactor
Continuous condensating reacts.
6. the preparation method of PMIDA according to claim 1, it is characterised in that the second step is adjusted using heat exchanger
Reaction temperature is in 120 degree Celsius~130 degree scopes.
7. the preparation method of PMIDA according to claim 1, it is characterised in that the pH value range of the 3rd step is
0.2~0.6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201710269433.0A CN106883264A (en) | 2017-04-24 | 2017-04-24 | A kind of preparation method of PMIDA |
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| CN201710269433.0A CN106883264A (en) | 2017-04-24 | 2017-04-24 | A kind of preparation method of PMIDA |
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ID=59183168
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101519360A (en) * | 2008-12-10 | 2009-09-02 | 上海泰禾(集团)有限公司 | Method for preparing iminodiacetic acid |
| CN101671362A (en) * | 2009-09-28 | 2010-03-17 | 南京第一农药集团有限公司 | Process for preparing N-(phosphonomethyl) iminodiacetic acid by hydroxyacetonitrile continuous method |
| CN103613616A (en) * | 2013-12-12 | 2014-03-05 | 重庆紫光化工股份有限公司 | Production equipment and production method of N-phosphonomethyl aminodiacetic acid |
-
2017
- 2017-04-24 CN CN201710269433.0A patent/CN106883264A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101519360A (en) * | 2008-12-10 | 2009-09-02 | 上海泰禾(集团)有限公司 | Method for preparing iminodiacetic acid |
| CN101671362A (en) * | 2009-09-28 | 2010-03-17 | 南京第一农药集团有限公司 | Process for preparing N-(phosphonomethyl) iminodiacetic acid by hydroxyacetonitrile continuous method |
| CN103613616A (en) * | 2013-12-12 | 2014-03-05 | 重庆紫光化工股份有限公司 | Production equipment and production method of N-phosphonomethyl aminodiacetic acid |
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Application publication date: 20170623 |