CN105669742B - A kind of purification process of glufosinate-ammonium - Google Patents
A kind of purification process of glufosinate-ammonium Download PDFInfo
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- CN105669742B CN105669742B CN201610022729.8A CN201610022729A CN105669742B CN 105669742 B CN105669742 B CN 105669742B CN 201610022729 A CN201610022729 A CN 201610022729A CN 105669742 B CN105669742 B CN 105669742B
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- ammonium
- glufosinate
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- 238000000746 purification Methods 0.000 title claims abstract description 16
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 title claims 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 amino bronsted lowry acids Chemical class 0.000 claims abstract description 7
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 7
- 150000001413 amino acids Chemical class 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 4
- 150000007528 brønsted-lowry bases Chemical class 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 7
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 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 abstract description 35
- 238000000034 method Methods 0.000 abstract description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 4
- 229910017053 inorganic salt Inorganic materials 0.000 abstract description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 150000007529 inorganic bases Chemical class 0.000 abstract description 2
- 238000006386 neutralization reaction Methods 0.000 abstract description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 8
- 238000005406 washing Methods 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000004400 serine Nutrition 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004176 ammonification Methods 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003355 serines Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009423 ventilation 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
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 purification process of glufosinate-ammonium, include the following steps:Glufosinate-ammonium hydrochloride, crude is added in solvent, then adds the aqueous solution of amino bronsted lowry acids and bases bronsted lowry, reacts 0.5 ~ 1.5h, adjusts the pH to 1 ~ 7 of reaction system, then filtered, drying obtains glufosinate-ammonium;By glufosinate-ammonium dissolving in a solvent, it then passes to ammonia and carries out salt-forming reaction, glufosinate-ammonium solid is precipitated, then filtered, drying obtains the glufosinate-ammonium of high-purity.The purifying process of the present invention avoids ethylene oxide, the propylene oxide using the difficult aliphatic amine removed and high risk, step is simple, inorganic salt content is low in obtained glufosinate-ammonium, purity is high, yield is high, and it is safe, technical process carries out neutralization reaction using water or alcohol as solvent, with ammonium hydroxide and inorganic base, meet the feature of environmental protection and economy principle, there is good industrial prospect.Also, the present invention is purified by adding amino acid, purification efficiency and product purity higher.
Description
Technical field
The invention belongs to the purification process of chemicals, and in particular to a kind of purification process of glufosinate-ammonium.
Background technology
Glufosinate-ammonium belongs to the natural disposition contact weedicide that goes out, and has the characteristics that efficient, low toxicity, low-residual and safe, quick-acting
Between between paraquat and glyphosate, be widely used in agricultural production, the structural formula of glufosinate-ammonium is as follows:
。
Contain the inorganic salt by-products such as a large amount of ammonium chloride in glufosinate-ammonium hydrochloride, crude and generate sticky organic impurities, state
Inside also there is the relevant report that glufosinate-ammonium hydrochloride purifying process is studied, as patent CN103819503 is referred to glufosinate-ammonium salt first
Then hydrochlorate ammonification obtains glufosinate-ammonium, which introduces ammonium hydrogen carbonate during the reaction, to most into salt with carbon dioxide
It needs to remove by heat resolve in finished product, is easy to cause product quality decline, and carbon dioxide usage amount is big, utilization rate
It is low.Patent CN201110160129 by glufosinate-ammonium hydrochloride successively by esterification, hydrolysis and in ethylene oxide
With glufosinate-ammonium is obtained by the reaction, finally lead to ammonia and obtain glufosinate-ammonium ammonium salt, the process route is long, and consumption is big, and yield is low, in and
Ethylene oxide is used in reaction, operational hazards coefficient is big, of high cost.
Invention content
The technical problems to be solved by the invention are to provide a kind of purification process of environmentally protective, at low cost glufosinate-ammonium,
And the purity of obtained glufosinate-ammonium is high, yield is high.
For solution more than technical problem, the present invention adopts the following technical scheme that:
A kind of purification process of glufosinate-ammonium, includes the following steps:
Step(1), glufosinate-ammonium hydrochloride, crude is added in solvent, then add the aqueous solution of amino bronsted lowry acids and bases bronsted lowry,
0.5 ~ 1.5h is reacted, adjusts the pH to 1 ~ 7 of reaction system, then filtered, drying obtains glufosinate-ammonium;
Step(2), by step(1)Obtained glufosinate-ammonium dissolving in a solvent, then passes to ammonia and carries out salt-forming reaction,
Glufosinate-ammonium solid is precipitated, then filtered, drying obtains the glufosinate-ammonium of high-purity.
The reaction equation of the present invention is as follows:
。
Preferably, the purity of the glufosinate-ammonium hydrochloride, crude is 70% ~ 90%.
Preferably, step(1)In, the mass ratio that feeds intake of the glufosinate-ammonium hydrochloride, crude and the solvent is 1:
0.5~1.5。
Preferably, step(1)In, the solvent is water, alcohol or water and the mixed solvent of alcohol.
It is further preferred that the alcohol is methanol or ethyl alcohol.
Preferably, step(1)In, the mass concentration of the aqueous solution of the alkali is 20 ~ 40%.
Preferably, step(1)In, the aqueous solution of the alkali be selected from ammonium hydroxide, NaOH aqueous solutions, KOH aqueous solutions,
Na2CO3Aqueous solution, K2CO3One or more of aqueous solution.
It is further preferred that step(1)In, the aqueous solution of the alkali is selected from ammonium hydroxide or NaOH aqueous solutions.
Preferably, step(1)In, the molar ratio of the amino acid and the glufosinate-ammonium hydrochloride for 0.05 ~
0.1:1。
Specifically, the amino acid in the present invention includes the natural or artificial synthesized ammonia such as glycine, serine, phenylalanine
Base acid.
Preferably, step(1)In, reacted at 40 ~ 50 DEG C, be subsequently cooled to -10 ~ 10 DEG C, then carry out the filtering,
Baking step.
Preferably, step(1)In, adjust the pH to 1 ~ 5 of reaction system.
Preferably, step(2)In, mixed solvent of the solvent for water, alcohol or water and alcohol carries out described into salt
The temperature of reaction is 10 ~ 50 DEG C, and the reaction time is 0.5 ~ 2h.
It is further preferred that step(2)In, the solvent is that mass ratio is 1:The mixing of 9 ~ 19 water and methanol is molten
Agent.
Preferably, step(2)In, the ventilation flow rate of the ammonia is 40k ~ 50kg/h.
Preferably, step(2)In, the glufosinate-ammonium and the mass ratio that feeds intake of the solvent are 1:1.5~2.5.
Due to the implementation of above technical scheme, the present invention has following advantage compared with prior art:
The purifying process of the present invention avoids ethylene oxide, the epoxy third using the difficult aliphatic amine removed and high risk
Alkane, step is simple, and inorganic salt content is low in obtained glufosinate-ammonium, and purity is high, yield is high and safe, and technical process is with water
Or alcohol is solvent, carries out neutralization reaction with ammonium hydroxide and inorganic base, meets the feature of environmental protection and economy principle, has industrialization well
Prospect.Also, the present invention is purified by adding amino acid, purification efficiency and product purity higher, and the purification time is significantly
Shorten.
Specific embodiment
The present invention is described in further details below in conjunction with specific embodiment.It should be understood that these embodiments are for saying
The bright basic principles, principal features and advantages of the present invention, and the present invention is not limited by the following examples.It is used in embodiment
Implementation condition can do further adjustment according to specific requirement, and the implementation condition being not specified is usually the condition in routine experiment.
Without indicating, " % " is mass percent, and ratio is mass ratio.
Embodiment 1
By 80 grams of glufosinate-ammonium hydrochloride, crudes(Purity about 80%)It is added in 100 grams of water, adds 2.4 grams of sweet ammonia at normal temperatures
Acid and 30 gram 25% of ammonium hydroxide mixed solution are heated to 40 DEG C and react 1 hour, and pH value 6 is cooled to 10 DEG C, and filtering, methanol washs,
Drying obtains 51 grams of off-white powder, yield 96%, purity 98%.
Embodiment 2
By 80 grams of glufosinate-ammonium hydrochloride, crudes(Purity about 80%)It is added to the mixed solvent of 100 grams of first alcohol and waters(1:1)
In, 3.4 grams of serines and 15 gram 30% of sodium carbonate mixed aqueous solution are added at normal temperatures, are heated to 45 DEG C and are reacted 1 hour, pH
Value is cooled to 5 DEG C, filtering, methanol washing dries and obtains 45 grams of off-white powder, yield 85%, purity 96% to 1.
Embodiment 3
By 80 grams of glufosinate-ammonium hydrochloride, crudes(Purity about 80%)It is added in 100 grams of water, 2.4 grams of dropwise addition is sweet at normal temperatures
Propylhomoserin and 15 gram 30% of NaOH aqueous solutions are heated to 45 DEG C and react 1 hour, and pH value 5 is cooled to 5 DEG C, and filtering, methanol is washed
It washs, drying obtains 50 grams of off-white powder, yield 95%, purity 98%.
Comparative example 1
By 80 grams of glufosinate-ammonium hydrochloride, crudes(Purity about 80%)It is added in 100 grams of water, 15 gram 30% is added dropwise at normal temperatures
NaOH aqueous solutions, be heated to 40 DEG C and react 1 hour, pH value 5 is cooled to 5 DEG C, filtering, and methanol washing, it is white that drying obtains class
48 grams of color solid, yield 90%, purity 95%.
Comparative example 2
By 80 grams of glufosinate-ammonium hydrochloride, crudes(Purity about 80%)It is added in 100 grams of water, adds 25% ammonium hydroxide at normal temperatures
PH value is adjusted to 5, is crystallized 1 hour, filtering, methanol washing, drying obtains 49 grams of off-white powder, yield 89%, purity 95%.
Embodiment 4
100 grams of glufosinate-ammoniums that above-mentioned technique obtains are suspended in 200 grams of methanol, at normal temperatures with the flow velocity of 50kg/h
It is passed through ammonia 1 hour, filters, washing, drying obtains 102 grams of glufosinate-ammonium ammonium salts, yield 93.5%, purity 90%.
Embodiment 5
100 grams of glufosinate-ammoniums that above-mentioned technique obtains are suspended in 200 grams of methanol/waters(95:5)In, at normal temperatures with
The flow velocity of 40kg/h is passed through ammonia 1 hour, filters, and washing, drying obtains 104 grams of glufosinate-ammonium ammonium salts, yield 96%, purity 98%.
Embodiment 6
100 grams of glufosinate-ammoniums that above-mentioned technique obtains are suspended in 200 grams of methanol/waters(80:20)In, at normal temperatures with
The flow velocity of 50kg/h is passed through ammonia 1 hour, filters, and washing, drying obtains 87 grams of glufosinate-ammonium ammonium salts, yield 80%, purity 95%.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar can understand present disclosure and implement according to this, and it is not intended to limit the scope of the present invention, all according to the present invention
The equivalent change or modification that Spirit Essence is made, should be covered by the protection scope of the present invention.
Claims (6)
1. a kind of purification process of glufosinate-ammonium, it is characterised in that:Include the following steps:
Step(1), glufosinate-ammonium hydrochloride, crude is added to the water, then add the aqueous solution of amino bronsted lowry acids and bases bronsted lowry, reaction 0.5
~ 1.5h, adjusts the pH to 5 ~ 6 of reaction system, and then filtered, drying obtains glufosinate-ammonium;The aqueous solution of the alkali is choosing
From ammonium hydroxide, NaOH aqueous solutions, KOH aqueous solutions, Na2CO3Aqueous solution, K2CO3One or more of aqueous solution;
Step(2), by step(1)Obtained glufosinate-ammonium dissolving in a solvent, then passes to ammonia and carries out salt-forming reaction, be precipitated
Glufosinate-ammonium solid, then filtered, drying obtain the glufosinate-ammonium of high-purity.
2. the purification process of glufosinate-ammonium according to claim 1, it is characterised in that:The glufosinate-ammonium hydrochloride, crude
Purity is 70% ~ 90%.
3. the purification process of glufosinate-ammonium according to claim 1, it is characterised in that:Step(1)In, the amino acid with
The molar ratio of the glufosinate-ammonium hydrochloride is 0.05 ~ 0.1:1.
4. the purification process of glufosinate-ammonium according to claim 1, it is characterised in that:Step(1)In, it is anti-at 10 ~ 50 DEG C
Should, -10 ~ 10 DEG C are subsequently cooled to, then carry out the filtering, baking step.
5. the purification process of glufosinate-ammonium according to claim 1, it is characterised in that:Step(2)In, the solvent is
The mixed solvent of water, alcohol or water and alcohol, the temperature for carrying out the salt-forming reaction are 10 ~ 50 DEG C, and the reaction time is 0.5 ~ 2h.
6. the purification process of glufosinate-ammonium according to claim 5, it is characterised in that:Step(2)In, the solvent is matter
Amount is than being 1:9 ~ 19 water and the mixed solvent of methanol.
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