CN109320550A - The preparation method of L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylic acid salt solution - Google Patents
The preparation method of L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylic acid salt solution Download PDFInfo
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- CN109320550A CN109320550A CN201811302644.0A CN201811302644A CN109320550A CN 109320550 A CN109320550 A CN 109320550A CN 201811302644 A CN201811302644 A CN 201811302644A CN 109320550 A CN109320550 A CN 109320550A
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- glufosinate
- ammonium
- carboxylic acid
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- 239000002253 acid Substances 0.000 title claims abstract description 22
- 239000012266 salt solution Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000011260 aqueous acid Substances 0.000 claims abstract description 11
- 239000003513 alkali Substances 0.000 claims abstract description 9
- 239000012528 membrane Substances 0.000 claims abstract description 6
- 235000002639 sodium chloride Nutrition 0.000 claims description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 5
- 238000002425 crystallisation Methods 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- 239000012467 final product Substances 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- 239000000243 solution Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- -1 salts small molecule Chemical class 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 238000012271 agricultural production Methods 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000196324 Embryophyta 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
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 102000005396 glutamine synthetase Human genes 0.000 description 1
- 108020002326 glutamine synthetase Proteins 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000009333 weeding Methods 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
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- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to field of agricultural herbicide, for the low problem of finished product purity, provide a kind of L-glufosinate-ammonium acid or the preparation method of L-glufosinate-ammonium carboxylic acid salt solution, the technical solution is as follows: certain density L-glufosinate-ammonium hydrochloric acid saline solution is adjusted downward to PH=1.8-2.2 with alkali certain temperature, then with the inorganic salts generated in organic membrane separating process, L-glufosinate-ammonium aqueous acid is obtained；Or L-glufosinate-ammonium hydrochloric acid saline solution is adjusted downward to PH=6.5-7 with alkali certain temperature, then with the inorganic salts generated in organic membrane separating process, obtain L-glufosinate-ammonium carboxylic acid salt solution.Under the action of organic film, separating inorganic salts reduce and generate crystallization purifying, so that the purity of final product is higher.
Description
Technical field
The present invention relates to field of agricultural herbicide, water-soluble more particularly, to a kind of L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylate
The preparation method of liquid.
Background technique
Glufosinate-ammonium (glufosinate-ammonium) is by German Hirst company (existing Beyer Co., Ltd) development and production, chemistry
Entitled 4- { hydroxyl (methyl) phosphono }-DL- high lactamine ammonium salt is glutamine synthetase inhibitor, non-selective to tag
Type herbicide.Studies have shown that its activity of weeding is only limitted to L- isomers, D body is active without biological weed control, therefore L-glufosinate-ammonium
Bioactivity is 2 times of the DL raceme of comparable sodium.
Glufosinate-ammonium hydrochloride is not suitable for being directly used in agricultural production, can after being removed the hydrogen chloride combined on molecule with alkali
For agricultural production.
Reaction process is as follows:
But since the inorganic salts that neutralization reaction generates are soluble easily in water, lead to inorganic salts and L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylic
Acid sodium-salt is difficult to separate, and is easy to produce the situation that crystallization purifying causes finished product purity low, and therefore, there are also improve space.
Summary of the invention
In view of the deficiencies of the prior art, the present invention intends to provide a kind of L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylic
The preparation method of acid salt aqueous solution has the advantages that finished product purity is high.
To achieve the above object, the present invention provides the following technical scheme that
The preparation method of a kind of L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylic acid salt solution, by certain density L-glufosinate-ammonium salt
Acid salt aqueous solution is adjusted downward to PH=1.8-2.2 with alkali certain temperature, then with the inorganic salts generated in organic membrane separating process, obtains
To L-glufosinate-ammonium aqueous acid；Or L-glufosinate-ammonium hydrochloric acid saline solution is adjusted downward to PH=6.5-7 with alkali certain temperature, then use
The inorganic salts generated in organic membrane separating process obtain L-glufosinate-ammonium carboxylic acid salt solution.
By using above-mentioned technical proposal, under the organic film effect of specific materials, certain pore size, inorganic salts small molecule can
To pass through organic film, and the big organic molecule difficulty such as L-glufosinate-ammonium is sour, L-glufosinate-ammonium carboxylate passes through, so that it is inorganic to reach separation
The effect of salt reduces and generates the situation that crystallization purifying causes finished product purity low, so that L-glufosinate-ammonium aqueous acid and L- grass ammonium
The purity of phosphine carboxylic acid saline solution is higher, and L-glufosinate-ammonium acid and the loss of L-glufosinate-ammonium carboxylate are few, reduce cost.
The present invention is further arranged to: ee >=80% of the L-glufosinate-ammonium hydrochloride.
By using above-mentioned technical proposal, by ee >=80% of L-glufosinate-ammonium hydrochloride, so that L-glufosinate-ammonium hydrochloride
Activity is higher, so that the activity of manufactured L-glufosinate-ammonium aqueous acid and L-glufosinate-ammonium carboxylic acid salt solution are higher, removes
Careless effect is preferable.
The present invention is further arranged to: the concentration range of the certain density L-glufosinate-ammonium hydrochloride is 1%-30%.
By using above-mentioned technical proposal, avoid L-glufosinate-ammonium hydrochloride concentration it is excessively high cause in mixed liquor solvent insufficient and
So that inorganic salts, which are insoluble in, to be caused to inhibit the phenomenon that neutralization reaction in solvent, guarantee that neutralization reaction is gone on smoothly.
The present invention is further arranged to: the certain temperature is 0 DEG C -60 DEG C.
It is 0 DEG C -60 DEG C by mixeding liquid temperature by using above-mentioned technical proposal, so that neutralization reaction is in is suitable for
Reaction temperature, simultaneously because solvent is water, the case where reducing solvent evaporation and solvent is caused to reduce.
The present invention is further arranged to: the alkali be sodium hydroxide, potassium hydroxide, ammonia, the inorganic salts generated in the process according to
Secondary is sodium chloride, potassium chloride, ammonium chloride.
By using above-mentioned technical proposal, so that neutralization reaction rate is very fast and the inorganic salts that generate are soluble easily in water, it is convenient for
Separation.
The present invention is further arranged to: the carboxylate is L-glufosinate-ammonium carboxylic acid sodium salt, L-glufosinate-ammonium carboxylic acid potassium salt, L- grass
Ammonium phosphine carboxylic acid ammonium salt.
By using above-mentioned technical proposal, so that L-glufosinate-ammonium carboxylate is soluble easily in water and molecular weight is larger, it is difficult to pass through
Organic film, convenient for being separated with inorganic salts.
The present invention is further arranged to: L-glufosinate-ammonium in the L-glufosinate-ammonium aqueous acid obtained after film process: inorganic salts >=
98:2, L-glufosinate-ammonium acid loss≤1%.
By using above-mentioned technical proposal, so that the purity of L-glufosinate-ammonium acid is higher, and significant loss is less, control at
This.
The present invention is further arranged to: L-glufosinate-ammonium carboxylic acid in the L-glufosinate-ammonium carboxylic acid salt solution obtained after film process
Salt: inorganic salts >=98:2, L-glufosinate-ammonium carboxylate loss≤1%.
By using above-mentioned technical proposal, so that the purity of L-glufosinate-ammonium carboxylate is higher, and significant loss is less, control
Cost.
In conclusion the invention has the following advantages:
1. under the action of organic film, separating inorganic salts reduce and generate the situation that crystallization purifying causes finished product purity low, make
The purity for obtaining L-glufosinate-ammonium aqueous acid and L-glufosinate-ammonium carboxylic acid salt solution is higher；
2. passing through ee >=80% of L-glufosinate-ammonium hydrochloride, so that manufactured L-glufosinate-ammonium aqueous acid and L-glufosinate-ammonium
The activity of carboxylic acid salt solution is higher, and herbicidal effect is preferable；
3. the concentration for passing through L-glufosinate-ammonium hydrochloride in L-glufosinate-ammonium hydrochloric acid saline solution is 1%-30%, L- grass ammonium is avoided
Phosphonium salt hydrochlorate excessive concentration leads to solvent deficiency in mixed liquor and inorganic salts, which are insoluble in solvent, to be caused to inhibit neutralization reaction
The case where, guarantee that neutralization reaction is gone on smoothly.
Specific embodiment
With reference to embodiments, invention is further described in detail.
Embodiment 1
A kind of preparation method of L-glufosinate-ammonium acid:
500L reaction kettle puts into 200kg16%L- glufosinate-ammonium hydrochloric acid saline solution, and temperature control is no more than 60 DEG C, is slowly added dropwise
20% sodium hydrate aqueous solution is adjusted PH=1.8-2.2, is formed the free amino acid of smart glufosinate-ammonium using isoelectric point, finally delayed
Slow stirring 30 minutes, PH is stable at 1.8-2.2.
Obtained aqueous solution crosses organic film, is slowly added to 300kg deionized water elution inorganic salts, finally obtains
The L-glufosinate-ammonium aqueous acid of 120kg22%, sodium chloride content 0.22%.
Embodiment 2
500L reaction kettle puts into 200kg16%L- glufosinate-ammonium hydrochloric acid saline solution, and temperature control is no more than 60 DEG C, is slowly added dropwise
25% ammonia spirit is adjusted PH=1.8-2.2, is formed the free amino acid of smart glufosinate-ammonium using isoelectric point, be finally slowly stirred
30 minutes, PH was stable at 1.8-2.2.
Obtained aqueous solution crosses organic film, is slowly added to 300kg deionized water elution inorganic salts, finally obtains
The L-glufosinate-ammonium aqueous acid of 120kg22.1%, ammonium chloride content 0.21%.
Embodiment 3
500L reaction kettle puts into 200kg16%L- glufosinate-ammonium hydrochloric acid saline solution, and temperature control is no more than 60 DEG C, is slowly added dropwise
20% sodium hydrate aqueous solution adjusts PH=6.5-7, forms the amino acid mono-sodium salt of smart glufosinate-ammonium, is finally slowly stirred 30 points
Clock, PH are stable at 6.5-7.
Obtained aqueous solution crosses organic film, is slowly added to 600kg deionized water elution inorganic salts, finally obtains
The L-glufosinate-ammonium sodium-salt aqueous solution of 120kg24.7%, sodium chloride content 0.2%.
Embodiment 4
500L reaction kettle puts into 200kg16%L- glufosinate-ammonium hydrochloric acid saline solution, and temperature control is no more than 60 DEG C, is slowly added dropwise
25% ammonia spirit adjusts PH=6.5-7, forms the amino acid mono-sodium salt of smart glufosinate-ammonium, is finally slowly stirred 30 minutes, PH is steady
Due to 6.5-7.
Obtained aqueous solution crosses organic film, is slowly added to 600kg deionized water elution inorganic salts, finally obtains
The L-glufosinate-ammonium ammonium salt aqueous solution of 120kg24.8%, ammonium chloride content 0.23%.
According to embodiment 1- embodiment 4, the content of inorganic salts only has 0.2%-0.23%, the purity of final product in final product
It is higher.
The embodiment of present embodiment is presently preferred embodiments of the present invention, not limits protection of the invention according to this
Range, therefore: the equivalence changes that all structures under this invention, shape, principle are done, should all be covered by protection scope of the present invention it
It is interior.
Claims (8)
1. the preparation method of a kind of L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylic acid salt solution, it is characterized in that: by certain density L-
Glufosinate-ammonium hydrochloric acid saline solution is adjusted downward to PH=1.8-2.2 with alkali certain temperature, then with the nothing generated in organic membrane separating process
Machine salt obtains L-glufosinate-ammonium aqueous acid；Or L-glufosinate-ammonium hydrochloric acid saline solution is adjusted downward to PH=6.5-7 with alkali certain temperature,
Then with the inorganic salts generated in organic membrane separating process, L-glufosinate-ammonium carboxylic acid salt solution is obtained.
2. the preparation method of L-glufosinate-ammonium acid according to claim 1 or L-glufosinate-ammonium carboxylic acid salt solution, it is characterized in that:
Ee >=80% of the L-glufosinate-ammonium hydrochloride.
3. the preparation method of L-glufosinate-ammonium acid according to claim 1 or L-glufosinate-ammonium carboxylic acid salt solution, it is characterized in that:
The concentration range of the certain density L-glufosinate-ammonium hydrochloride is 1%-30%.
4. the preparation method of L-glufosinate-ammonium acid according to claim 1 or L-glufosinate-ammonium carboxylic acid salt solution, it is characterized in that:
The certain temperature is 0 DEG C -60 DEG C.
5. the preparation method of L-glufosinate-ammonium acid according to claim 1 or L-glufosinate-ammonium carboxylic acid salt solution, it is characterized in that:
The alkali is sodium hydroxide, potassium hydroxide, ammonia, and the inorganic salts generated in the process are followed successively by sodium chloride, potassium chloride, ammonium chloride.
6. the preparation method of L-glufosinate-ammonium acid according to claim 1 or L-glufosinate-ammonium carboxylic acid salt solution, it is characterized in that:
The carboxylate is L-glufosinate-ammonium carboxylic acid sodium salt, L-glufosinate-ammonium carboxylic acid potassium salt, L-glufosinate-ammonium ammonium carboxylate salt.
7. the preparation method of L-glufosinate-ammonium acid according to claim 1 or L-glufosinate-ammonium carboxylic acid salt solution, it is characterized in that:
L-glufosinate-ammonium in the L-glufosinate-ammonium aqueous acid obtained after film process: inorganic salts >=98:2, L-glufosinate-ammonium acid loss≤1%.
8. the preparation method of L-glufosinate-ammonium acid according to claim 1 or L-glufosinate-ammonium carboxylic acid salt solution, it is characterized in that:
L-glufosinate-ammonium carboxylate in the L-glufosinate-ammonium carboxylic acid salt solution obtained after film process: inorganic salts >=98:2, L-glufosinate-ammonium carboxylic acid
Salt loss≤1%.
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| CN201811302644.0A CN109320550A (en) | 2018-11-02 | 2018-11-02 | The preparation method of L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylic acid salt solution |
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| CN201811302644.0A CN109320550A (en) | 2018-11-02 | 2018-11-02 | The preparation method of L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylic acid salt solution |
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| CN201811302644.0A Pending CN109320550A (en) | 2018-11-02 | 2018-11-02 | The preparation method of L-glufosinate-ammonium acid or L-glufosinate-ammonium carboxylic acid salt solution |
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Application publication date: 20190212 |