CN105063658B - The method for preparing iminodiacetic acid - Google Patents
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Abstract
The present invention provides a kind of method for preparing iminodiacetic acid, prepared using the method for substep electrolysis, Iminodiacetic acid sodium salt is electrolysed to the sodium of iminodiacetic acid one first, then the sodium of iminodiacetic acid one is electrolysed to iminodiacetic acid, using the method for electrolysis, its advantage is environmental protection, electrolytic process, which produces accessory substance tool, to have been widely used, cell reaction process is simple, it is easy to operate, and the mode relative to once electrolytic is electrolysed by the way of substep is electrolysed, Iminodiacetic acid sodium salt is electrolysed to can use larger current density during one sodium of iminodiacetic acid, therefore efficiency is higher.
Description
Technical field
The present invention relates to the method for preparing iminodiacetic acid, iminodiacetic acid is more particularly to prepared by electrolysis
Method.
Background technology
Iminodiacetic acid (salt) is the important intermediate of the careless broad-spectrum herbicide-glyphosate pesticide of production drought.Glyphosate is
A kind of non-selective, noresidue steriland herbicide, it is highly effective to prennical root weeds, it is widely used in glue, mulberry, tea, orchard
And sugarcane field.
The method of synthesis of iminodiacetic acid is many both at home and abroad at present, but last process is all by iminodiacetic acid sodium salt
Lead to superacidulated mode and obtain iminodiacetic acid, the method for being acidified with acid can consume substantial amounts of soda acid, while a large amount of sodium salts of by-product, by
In the reason for solubility, the iminodiacetic acid being still dissolved in mother liquor containing about 60g/L, the method not only produces substantial amounts of useless
Liquid, brings serious environmental problem, and conversion ratio is relatively low, it is impossible to reach complete conversion.
The content of the invention
It is an object of the invention to overcome the shortcomings of above-mentioned technology, so as to provide a kind of side for preparing iminodiacetic acid
Method, prepares simple, high conversion rate and pollution-free.
The technical solution adopted in the present invention is such：A kind of method for preparing iminodiacetic acid, using substep electricity
Prepared by the method for solution, specifically carry out as follows：
A kind of method for preparing iminodiacetic acid, is prepared, specifically as follows using the method for substep electrolysis
Carry out：
S1：Iminodiacetic acid disodium salt solution is prepared into the sodium salt of iminodiacetic acid one by way of electrolysis molten
Liquid；
（1）Electrolytic process is carried out in the three Room electrolytic cells containing anode chamber, cathode chamber and medial compartment；It is electrolysed institute's obtaining current
Density is 100-5000 A/m2；
（2）It is 5-40% by concentration, temperature is flowed for 50-90 DEG C of iminodiacetic acid disodium salt solution with 0-200 mm/s
Speed reaches by once electrolytic or cyclic electrolysis by the medial compartment of the electrolytic cell and is fully converted to the sodium of iminodiacetic acid one
Medial compartment is exported after salting liquid, pH value control is 3-8；
（3）At the same time, it is 1-50% by concentration, temperature is that 50-90 DEG C of acid solution imports the anode of the electrolytic cell
Room, and moisturizing is continued to the acid solution of importing, the elevated acid solution of concentration is exported into anode chamber, while collecting oxygen or chlorine
Gas；
（4）At the same time, it is 1-35% by concentration, temperature imports the electrolytic cell for 50-90 DEG C of sodium hydroxide solution
Cathode chamber, cathode chamber is exported by the elevated sodium hydroxide solution of concentration, while collecting hydrogen；
S2：The sodium salt solution of iminodiacetic acid one is prepared into iminodiacetic acid (salt) acid solution by way of electrolysis；
（1）Electrolytic process is carried out in the three Room electrolytic cells containing anode chamber, cathode chamber and medial compartment；It is electrolysed institute's obtaining current
Density is 100-2000 A/m2；
（2）It is 5-40% by concentration, temperature is flowed for 50-90 DEG C of the sodium salt solution of iminodiacetic acid one with 0-200 mm/s
The fast medial compartment by the electrolytic cell, after once electrolytic or cyclic electrolysis reach that 30-50% is converted into iminodiacetic acid
Solution exports medial compartment, and pH value control is 0.1-2；Cool down solution outside groove to separate out after iminodiacetic acid (salt) acid crystal, mother liquor and Asia
Intermediate compartment circulation electrolysis is entered back into after the mixing of the sodium salt solution of aminodiacetic acid one；
（3）At the same time, it is 1-50% by concentration, temperature is that 50-90 DEG C of acid solution imports the anode of the electrolytic cell
Room, and moisturizing is continued to the acid solution of importing, the elevated acid solution of concentration is exported into anode chamber, while collecting oxygen or chlorine
Gas；
（4）At the same time, it is 1-35% by concentration, temperature imports the electrolytic cell for 50-90 DEG C of sodium hydroxide solution
Cathode chamber, cathode chamber is exported by the elevated sodium hydroxide solution of concentration, while collecting hydrogen.
It is further improved to be：The iminodiacetic acid disodium salt solution is iminodiacetic acid disodium salt or imino group
The mixed solution of diethyl acid disodium salt and the sodium salt of iminodiacetic acid one, the iminodiacetic acid disodium salt solution is before electrolysis
By secondary filter.
It is further improved to be：The acid solution is sulfuric acid or hydrochloric acid or phosphoric acid or other inorganic acids or above-mentioned sour mixed
Compound.
It is further improved to be：The water persistently supplemented is distilled water or deionized water.
It is further improved to be：Solution in electrolytic process, three rooms parallel fluid flow or series flow in a cell.
It is further improved to be：The material of anode chamber is titanium, stainless steel, copper, plastics or metal liner plastics；Cathode chamber
Material is nickel, stainless steel, copper, carbon steel, plastics or metal liner plastics；The material of medial compartment is nickel, stainless steel, copper, carbon steel, plastics
Or metal liner plastics.
It is further improved to be：Barrier film between anode chamber and medial compartment is cation-exchange membrane or porous septum, negative electrode
Barrier film between room and medial compartment is cation-exchange membrane or porous septum.
It is further improved to be：Cation-exchange membrane in anode chamber is that the cation in PEM, cathode chamber is handed over
Film is changed for PEM or sodium ion exchange film.
It is further improved to be：Anode in anode chamber analyses oxygen electrode or DSA analysis chloride electrode, stainless steel electrode, carbon for DSA
Material electrode, platinum electrode；Negative electrode in cathode chamber is Ni-based active electrode, nickel electrode, copper electrode, stainless steel electrode, ferroalloy electricity
Pole, carbon electrode.
It is further improved to be：Step S1 and step S2 is electrolysed in same electrolytic cell or in independent electrolysis
It is electrolysed in groove.
By using preceding solution, the beneficial effects of the invention are as follows：Using the method for substep electrolysis, by imino-diacetic
Acetic acid disodium salt is converted into after the sodium salt of iminodiacetic acid one, then converting by the sodium salt of iminodiacetic acid one is imino-diacetic
Acetic acid, its advantage includes：(1), without using mineral acid acidified Iminodiacetic acid sodium salt, thus make in solution without inorganic
Salt, also just the need for no later separation, and then eliminates the problem of brine waste is handled；(2), electrolytic process produces accessory substance
NaOH, hydrogen, oxygen（Or chlorine）, tool has been widely used；(3), cell reaction process is simple, easy to operate, using substep
The mode of electrolysis is electrolysed the mode relative to once electrolytic, and first Iminodiacetic acid sodium salt is electrolysed to iminodiacetic acid
Larger current density can be used during one sodium, therefore efficiency is higher.
Brief description of the drawings
Fig. 1 is electrolytic cell schematic diagram.
Embodiment
The present invention is further illustrated below in conjunction with embodiment.
Electrolytic cell as shown in Figure 1, is made up of anode chamber, three rooms of cathode chamber and medial compartment, by two barrier films between three Room
Separate；Comprising an anode in anode chamber, a negative electrode is included in cathode chamber；Electrolytic cell, can be acyclic type or bipolar type knot
Structure, the electrolytic process of this method can be that one group of electrolytic cell or the combination of multigroup electrolytic cell are carried out.
Film and electrode assemblie in electrolytic cell are core, the material of anode chamber is titanium, stainless steel, copper, plastics or
Metal liner plastics；The material of cathode chamber is nickel, stainless steel, copper, carbon steel, plastics or metal liner plastics；The material of medial compartment be nickel,
Anode in stainless steel, copper, carbon steel, plastics or metal liner plastics, anode chamber analyses oxygen electrode or DSA analysis chloride electrode for DSA, stainless
Steel electrode, carbon materials electrode, platinum electrode；Negative electrode in cathode chamber is Ni-based active electrode, nickel electrode, copper electrode, stainless steel electrode,
Iron electrode, carbon electrode, electrode can be tabular or netted, the effective dimensions of monolithic negative electrode and anode be 500 mm ×
500 mm, die opening is 10 mm, and medial compartment is separated with anode chamber with PEM, and cathode chamber and medial compartment are handed over sodium ion
Change film to separate, the electrolyte of each room of electrolytic cell is entered by bottom, top outflow is powered with certain current density and is electrolysed to centre
Room pH is that the acidifying of the sodium of iminodiacetic acid one terminates for 5-7, and electrolysis to medial compartment PH is iminodiacetic acid acid for 0.1-2
Change terminates.
A kind of method for preparing iminodiacetic acid, is prepared, specifically as follows using the method for substep electrolysis
Carry out：
S1：Iminodiacetic acid disodium salt solution is prepared into the sodium salt of iminodiacetic acid one by way of electrolysis molten
Liquid；
（1）Electrolytic process is carried out in the three Room electrolytic cells containing anode chamber, cathode chamber and medial compartment；It is electrolysed institute's obtaining current
Density is 100-5000 A/m2；
（2）It is 5-40% by concentration, temperature is flowed for 50-90 DEG C of iminodiacetic acid disodium salt solution with 0-200 mm/s
Speed reaches by once electrolytic or cyclic electrolysis by the medial compartment of the electrolytic cell and is fully converted to the sodium of iminodiacetic acid one
Medial compartment is exported after salting liquid, pH value control is 3-8；
（3）At the same time, it is 1-50% by concentration, temperature is that 50-90 DEG C of acid solution imports the anode of the electrolytic cell
Room, and moisturizing is continued to the acid solution of importing, the elevated acid solution of concentration is exported into anode chamber, while collecting oxygen or chlorine
Gas；
（4）At the same time, it is 1-35% by concentration, temperature imports the electrolytic cell for 50-90 DEG C of sodium hydroxide solution
Cathode chamber, cathode chamber is exported by the elevated sodium hydroxide solution of concentration, while collecting hydrogen；
S2：The sodium salt solution of iminodiacetic acid one is prepared into iminodiacetic acid (salt) acid solution by way of electrolysis；
（1）Electrolytic process is carried out in the three Room electrolytic cells containing anode chamber, cathode chamber and medial compartment；It is electrolysed institute's obtaining current
Density is 100-2000 A/m2；
（2）It is 5-40% by concentration, temperature is flowed for 50-90 DEG C of the sodium salt solution of iminodiacetic acid one with 0-200 mm/s
The fast medial compartment by the electrolytic cell, after once electrolytic or cyclic electrolysis reach that 30-50% is converted into iminodiacetic acid
Solution exports medial compartment, and pH value control is 0.1-2；Cool down solution outside groove to separate out after iminodiacetic acid (salt) acid crystal, mother liquor and Asia
Intermediate compartment circulation electrolysis is entered back into after the mixing of the sodium salt solution of aminodiacetic acid one；
（3）At the same time, it is 1-50% by concentration, temperature is that 50-90 DEG C of acid solution imports the anode of the electrolytic cell
Room, and moisturizing is continued to the acid solution of importing, the elevated acid solution of concentration is exported into anode chamber, while collecting oxygen or chlorine
Gas；
（4）At the same time, it is 1-35% by concentration, temperature imports the electrolytic cell for 50-90 DEG C of sodium hydroxide solution
Cathode chamber, cathode chamber is exported by the elevated sodium hydroxide solution of concentration, while collecting hydrogen.
The iminodiacetic acid disodium salt solution employed in this method is iminodiacetic acid disodium salt or imido
The mixed solution of base diethyl acid disodium salt and the sodium salt of iminodiacetic acid one, in order to ensure to produce the pure of the sodium of iminodiacetic acid one
Cleanliness, the iminodiacetic acid disodium salt solution passes through secondary filter before electrolysis.
The acid solution employed in this method is sulfuric acid or hydrochloric acid or phosphoric acid or other inorganic acids or above-mentioned sour
Mixture.
In order to improve the solution in efficiency, electrolytic process, three rooms parallel fluid flow or series flow in a cell.
In this method, step S1 and step S2 is electrolysed in same electrolytic cell or entered in independent electrolytic cell
Row electrolysis.
By the following examples and the effect of this method of comparative example is illustrated：
Embodiment 1
Iminodiacetic acid disodium salt concentration 5%, temperature 50 C, S1, S2 current density is 100 A/m2, die opening 1.5
Cm, cathode chamber uses sodium ion exchange film with medial compartment, and anolyte is 5% sulfuric acid, and anode DSA analyses oxygen electrode, and catholyte is 5% hydrogen
Sodium oxide molybdena, negative electrode is Ni-based activated cathode.The mm/s of flow velocity 0, solution cyclic electrolysis to pH is 2, and current efficiency is 97%.
Embodiment 2
Iminodiacetic acid disodium salt concentration 50%, 90 DEG C of temperature, S1, S2 current density are 1000 A/m2, die opening
1.5 cm, cathode chamber uses sodium ion exchange film with medial compartment, and anolyte is 5% sulfuric acid, and anode DSA analyses oxygen electrode, and catholyte is
5% NaOH, negative electrode is Ni-based activated cathode.The mm/s of flow velocity 200, solution cyclic electrolysis to pH is 0.1, and current efficiency is
96%。
Embodiment 3
Iminodiacetic acid disodium salt concentration 40%, 80 DEG C of temperature, the A/m of S1 current densities 30002, S2 current densities it is equal
For 1000 A/m2, the cm of die opening 1.5, cathode chamber is with medial compartment using sodium ion exchange film, and anolyte is 5% sulfuric acid, anode
DSA analyses oxygen electrode, and catholyte is 5% NaOH, and negative electrode is Ni-based activated cathode.The mm/s of flow velocity 2, solution cyclic electrolysis to pH
For 1, current efficiency is 93%.
Embodiment 4
Iminodiacetic acid disodium salt concentration 30%, temperature 70 C, S1, S2 current density is 2000 A/m2, die opening
1.5 cm, cathode chamber uses sodium ion exchange film with medial compartment, and anolyte is 5% sulfuric acid, and anode DSA analyses oxygen electrode, and catholyte is
5% NaOH, negative electrode is Ni-based activated cathode.The mm/s of flow velocity 2, solution cyclic electrolysis to pH is 2, and current efficiency is 92%.
Embodiment 5
Iminodiacetic acid disodium salt concentration 40%, 80 DEG C of temperature, the A/m of S1 current densities 50002, S2 current densities 100
A/m2, the cm of die opening 1.5, cathode chamber is with medial compartment using sodium ion exchange film, and anolyte is 10% sulfuric acid, anode DSA analysis oxygen
Electrode, catholyte is 10% NaOH, and negative electrode is Ni-based activated cathode.The mm/s of flow velocity 2, solution cyclic electrolysis to pH is 2, electricity
It is 94% to flow efficiency.
Embodiment 6
Iminodiacetic acid disodium salt concentration 40%, 80 DEG C of temperature, S1 current densities 5000A/m2, S2 current densities 2000
A/m2, the cm of die opening 1.5, cathode chamber is with medial compartment using proton ion exchange membrane, and anolyte is 5% sulfuric acid, anode DSA analysis oxygen
Electrode, catholyte is 5% NaOH, and negative electrode is Ni-based activated cathode.The mm/s of flow velocity 2, solution cyclic electrolysis to pH is 2, electricity
It is 90% to flow efficiency.
Embodiment 7
Iminodiacetic acid disodium salt concentration 40%, 80 DEG C of temperature, S1 current densities 100A/m2, S2 current densities 2000
A/m2, the cm of die opening 1.5, cathode chamber is with medial compartment using proton ion exchange membrane, and anolyte is 5% sulfuric acid, anode DSA analysis oxygen
Electrode, catholyte is 15% NaOH, and negative electrode is Ni-based activated cathode.The mm/s of flow velocity 2, solution cyclic electrolysis to pH is 2, electricity
It is 92% to flow efficiency.
Embodiment 8
Iminodiacetic acid disodium salt concentration 40%, 80 DEG C of temperature, S1 current densities 2500A/m2, S2 current densities 1000
A/m2, the cm of die opening 1.5, cathode chamber is with medial compartment using sodium ion exchange film, and anolyte is 20% hydrochloric acid, anode DSA analysis chlorine
Electrode, catholyte is 5% NaOH, and negative electrode is Ni-based activated cathode.The mm/s of flow velocity 2, solution cyclic electrolysis to pH is 0.1,
Current efficiency is 95%.
Embodiment 9
Iminodiacetic acid disodium salt concentration 40%, 80 DEG C of temperature, the A/m of S1 current densities 20002, S2 current densities 1000
A/m2, the cm of die opening 1.5, cathode chamber is with medial compartment using sodium ion exchange film, and anolyte is 5% sulfuric acid, anode DSA analysis oxygen electricity
Pole, catholyte is 5% NaOH, and negative electrode is nickel screen.The mm/s of flow velocity 2, solution cyclic electrolysis to pH is 2, and current efficiency is
96%。
The general principle and principal character and its advantage of the present invention has been shown and described above, the technical staff of the industry should
The understanding, the present invention is not limited to the above embodiments, the original for simply illustrating the present invention described in above-described embodiment and explanation
Reason, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these changes and improvements
It all fall within the protetion scope of the claimed invention, the claimed scope of the invention is by appending claims and its equivalent circle
It is fixed.
Claims (9)
1. a kind of method for preparing iminodiacetic acid, it is characterised in that：Prepared, specifically pressed using the method for substep electrolysis
Following method is carried out：
S1 ：Iminodiacetic acid disodium salt solution is prepared into the sodium salt solution of iminodiacetic acid one by way of electrolysis；
（1）Electrolytic process is carried out in the three Room electrolytic cells containing anode chamber, cathode chamber and medial compartment；It is electrolysed institute's power taking current density
For 1000-5000 A/ m2；
（2）It is 5-40% by concentration, temperature is logical with 0-200 mm/s flow velocitys for 50-90 DEG C of iminodiacetic acid disodium salt solution
The medial compartment of the electrolytic cell is crossed, reaches that to be fully converted to the sodium salt of iminodiacetic acid one molten by once electrolytic or cyclic electrolysis
Medial compartment is exported after liquid, the control of pH values is 3-8；
（3）At the same time, it is 1-50% by concentration, temperature is that 50-90 DEG C of acid solution imports the anode chamber of the electrolytic cell,
And moisturizing is continued to the acid solution of importing, the elevated acid solution of concentration is exported into anode chamber, while collecting oxygen or chlorine；
（4）At the same time, it is 1-35% by concentration, temperature is that 50-90 DEG C of sodium hydroxide solution imports the negative electrode of the electrolytic cell
Room, cathode chamber is exported by the elevated sodium hydroxide solution of concentration, while collecting hydrogen；
S2 ：The sodium salt solution of iminodiacetic acid one is prepared into iminodiacetic acid (salt) acid solution by way of electrolysis；
（1）Electrolytic process is carried out in the three Room electrolytic cells containing anode chamber, cathode chamber and medial compartment；It is electrolysed institute's power taking current density
For 1000-2000 A/ m2；
（2）It is 5-40% by concentration, temperature is logical with 0-200 mm/s flow velocitys for 50-90 DEG C of the sodium salt solution of iminodiacetic acid one
Cross the medial compartment of the electrolytic cell, by once electrolytic or cyclic electrolysis reach 30-50% after being converted into iminodiacetic acid it is molten
Liquid exports medial compartment, and the control of pH values is 0.1-2；Cool down solution outside groove to separate out after iminodiacetic acid (salt) acid crystal, mother liquor and Asia
Intermediate compartment circulation electrolysis is entered back into after the mixing of the sodium salt solution of aminodiacetic acid one；
（3）At the same time, it is 1-50% by concentration, temperature is that 50-90 DEG C of acid solution imports the anode chamber of the electrolytic cell,
And moisturizing is continued to the acid solution of importing, the elevated acid solution of concentration is exported into anode chamber, while collecting oxygen or chlorine；
（4）At the same time, it is 1-35% by concentration, temperature is that 50-90 DEG C of sodium hydroxide solution imports the negative electrode of the electrolytic cell
Room, cathode chamber is exported by the elevated sodium hydroxide solution of concentration, while collecting hydrogen；
Barrier film between anode chamber and medial compartment is cation-exchange membrane, and the barrier film between cathode chamber and medial compartment is handed over for cation
The cation-exchange membrane changed in film, anode chamber is PEM, the cation-exchange membrane in cathode chamber for PEM or
Sodium ion exchange film.
2. the method for preparing iminodiacetic acid as described in claim 1, it is characterised in that：The iminodiacetic acid two
Sodium salt solution is molten for the mixing of iminodiacetic acid disodium salt or iminodiacetic acid disodium salt and the sodium salt of iminodiacetic acid one
Liquid, the iminodiacetic acid disodium salt solution passes through secondary filter before electrolysis.
3. the method for preparing iminodiacetic acid as described in claim 1, it is characterised in that：The acid solution is sulfuric acid
Or hydrochloric acid or phosphoric acid or other inorganic acids.
4. the method for preparing iminodiacetic acid as described in claim 1, it is characterised in that：The acid solution be sulfuric acid,
Hydrochloric acid, phosphoric acid, the mixture of other inorganic acids.
5. the method for preparing iminodiacetic acid as described in claim 1, it is characterised in that：The water persistently supplemented is distillation
Water or deionized water.
6. the method for preparing iminodiacetic acid as described in claim 1, it is characterised in that：Electrolytic process, electrolytic cell used
For acyclic type or bipolar type, solution in three rooms parallel fluid flow or series flow in a cell.
7. the method for preparing iminodiacetic acid as described in claim 1, it is characterised in that：The material of anode chamber be titanium,
Stainless steel, copper, plastics or metal liner plastics；The material of cathode chamber is nickel, stainless steel, copper, carbon steel, plastics or metal liner plastics；
The material of medial compartment is nickel, stainless steel, copper, carbon steel, plastics or metal liner plastics.
8. the method for preparing iminodiacetic acid as described in claim 1, it is characterised in that：Anode in anode chamber is DSA
Analyse oxygen electrode or DSA analysis chloride electrode, stainless steel electrode, carbon materials electrode, platinum electrode；Negative electrode in cathode chamber is Ni-based activity electricity
Pole, nickel electrode, copper electrode, stainless steel electrode, iron electrode, carbon electrode.
9. the method for preparing iminodiacetic acid as described in claim 1, it is characterised in that：Step S1 and step S2 exists
It is electrolysed or is electrolysed in independent electrolytic cell in same electrolytic cell.
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| US5986128A (en) * | 1996-11-01 | 1999-11-16 | Monsanto Company | Use of monosodium iminodiacetic acid solutions in the preparation of N-phosphonomethyliminodiacetic acid |
| EP1004571A1 (en) * | 1998-05-27 | 2000-05-31 | Showa Denko Kabushiki Kaisha | Processes for producing amino acid having secondary or tertiary amino group and three or more carboxyl groups and its salt |
| CN101445464A (en) * | 2008-12-25 | 2009-06-03 | 广西壮族自治区化工研究院 | Method for preparing iminodiacetic acid from iminodiacetic acid disodium salt |
| CN101781224A (en) * | 2010-03-20 | 2010-07-21 | 杭州天创净水设备有限公司 | Cleaning production process of iminodiacetic acid |
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| US5986128A (en) * | 1996-11-01 | 1999-11-16 | Monsanto Company | Use of monosodium iminodiacetic acid solutions in the preparation of N-phosphonomethyliminodiacetic acid |
| EP1004571A1 (en) * | 1998-05-27 | 2000-05-31 | Showa Denko Kabushiki Kaisha | Processes for producing amino acid having secondary or tertiary amino group and three or more carboxyl groups and its salt |
| CN101445464A (en) * | 2008-12-25 | 2009-06-03 | 广西壮族自治区化工研究院 | Method for preparing iminodiacetic acid from iminodiacetic acid disodium salt |
| CN101781224A (en) * | 2010-03-20 | 2010-07-21 | 杭州天创净水设备有限公司 | Cleaning production process of iminodiacetic acid |
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