CN105541904A - Purification method for glufosinate-ammonium - Google Patents
Purification method for glufosinate-ammonium Download PDFInfo
- Publication number
- CN105541904A CN105541904A CN201610022720.7A CN201610022720A CN105541904A CN 105541904 A CN105541904 A CN 105541904A CN 201610022720 A CN201610022720 A CN 201610022720A CN 105541904 A CN105541904 A CN 105541904A
- Authority
- CN
- China
- Prior art keywords
- careless ammonium
- ammonium phosphine
- ammonium
- glufosinate
- purification process
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000746 purification Methods 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title abstract description 12
- 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 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- QLULGSLAHXLKSR-UHFFFAOYSA-N azane;phosphane Chemical compound N.P QLULGSLAHXLKSR-UHFFFAOYSA-N 0.000 claims description 25
- 239000007864 aqueous solution Substances 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- CDXRGXUDSDPCOI-UHFFFAOYSA-N N.OP(O)=O Chemical class N.OP(O)=O CDXRGXUDSDPCOI-UHFFFAOYSA-N 0.000 claims description 10
- MNNILAUAPXGGHC-UHFFFAOYSA-N N.P.Cl Chemical compound N.P.Cl MNNILAUAPXGGHC-UHFFFAOYSA-N 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 239000012046 mixed solvent Substances 0.000 claims description 7
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 229910017053 inorganic salt Inorganic materials 0.000 abstract description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract 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 7
- 239000002253 acid Substances 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- CYOOVEAWXNAHJA-UHFFFAOYSA-N azane;phosphane Chemical compound N.N.P CYOOVEAWXNAHJA-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 1
- 238000004176 ammonification Methods 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 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
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 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
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 239000003643 water by type 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
- C07F9/30—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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a purification method for glufosinate-ammonium. The method comprises the following steps that 1, a glufosinate-ammonium hydrochloride crude product is added into a solvent, then, an alkaline water solution is added to be subjected to a neutral reaction, the pH value of the reaction system is adjusted to be 1-4.5, and then filtering and drying are performed to obtain glufosinate-ammonium acid; 2, the glufosinate-ammonium acid obtained in the first step is dissolved into the solvent, then, ammonia gas is introduced to be subjected to a salt forming reaction, glufosinate-ammonium solid is separated out, and filtering and drying are performed to obtain high-purity glufosinate-ammonium. According to the purification technology, fatty amine hard to remove and high-risk ethylene oxide and epoxypropane are prevented from being used, the steps are simple, the obtained glufosinate-ammonium is low in inorganic salt content and high in purity, yield and safety, water or alcohol is used as the solvent in the technological process, ammonium hydroxide and inorganic base are used for being subjected to a neutral reaction, the purification method conforms to the environmental protection and economy principle, and the good industrial prospect is achieved.
Description
Technical field
The invention belongs to the purification process of chemical, be specifically related to a kind of purification process of careless ammonium phosphine.
Background technology
Grass ammonium phosphine belongs to the natural disposition contact weedicide that goes out, and have efficient, low toxicity, low residue and safety feature, between its quick-acting between Paraquat and glyphosate, be widely used in agriculture production, the structural formula of careless ammonium phosphine is as follows:
。
Contain the inorganic salt by-product such as a large amount of ammonium chloride in grass ammonium phosphine hydrochloride, crude and produce thickness organic impurity, the domestic relevant report also having careless ammonium phosphonium salt hydrochlorate purifying process to study, as patent CN103819503 refer to first by careless ammonium phosphonium salt hydrochlorate ammonification salify, then careless ammonium phosphonic acids is obtained with carbonic acid gas, this technique introduces bicarbonate of ammonia in reaction process, need to be removed by thermal degradation in the finished product, quality product is easily caused to decline, and carbon dioxide usage amount is large, utilization ratio is low.Patent CN201110160129 by careless ammonium phosphonium salt hydrochlorate successively through esterification, hydrolysis reaction and obtain careless ammonium phosphonic acids with the neutralization reaction of oxyethane, finally logical ammonia obtains careless ammonium phosphine ammonium salt, this operational path is long, consume large, yield is low, in neutralization reaction, use oxyethane, its operational hazards coefficient is large, and cost is high.
Summary of the invention
Technical problem to be solved by this invention is to provide the purification process of a kind of environmental protection, careless ammonium phosphine that cost is low, and the purity of the careless ammonium phosphine obtained is high, productive rate is high.
For solving above technical problem, the present invention adopts following technical scheme:
A purification process for careless ammonium phosphine, comprises the steps:
Step (1), careless ammonium phosphine hydrochloride, crude to be joined in solvent, and then the aqueous solution adding alkali carries out neutralization reaction, regulate pH to 1 ~ 4.5 of reaction system, then after filtration, dry and obtain careless ammonium phosphonic acids;
Step (2), careless ammonium phosphonic acids step (1) obtained dissolve in a solvent, then pass into ammonia and carry out salt-forming reaction, separate out careless ammonium phosphine solid, then after filtration, dry and obtain highly purified careless ammonium phosphine.
The reaction formula of above-mentioned reaction process is:
.
Preferably, the purity of described careless ammonium phosphine hydrochloride, crude is 70% ~ 90%.
Preferably, in step (1), described careless ammonium phosphine hydrochloride, crude and the mass ratio that feeds intake of described solvent are 1:0.5 ~ 1.5.
Preferably, in step (1), described solvent is the mixed solvent of water, alcohol or water and alcohol.
Further preferably, described alcohol is methyl alcohol or ethanol.
Preferably, in step (1), the mass concentration of the aqueous solution of described alkali is 20 ~ 40%.
Preferably, in step (1), the aqueous solution of described alkali is for being selected from ammoniacal liquor, the NaOH aqueous solution, the KOH aqueous solution, Na
2cO
3the aqueous solution, K
2cO
3one or more in the aqueous solution.
Further preferably, in step (1), the aqueous solution of described alkali is for being selected from ammoniacal liquor or the NaOH aqueous solution.
Preferably, in step (1), the temperature of carrying out described neutralization reaction is 10 ~ 50 DEG C.
Preferably, in step (2), described solvent is the mixed solvent of water, alcohol or water and alcohol.
Further preferably, in step (2), described solvent is mass ratio is the water of 1:9 ~ 19 and the mixed solvent of methyl alcohol.
Preferably, in step (2), the temperature of carrying out described salt-forming reaction is 10 ~ 50 DEG C, and the reaction times is 0.5 ~ 2h.
Preferably, in step (2), the ventilation flow rate of described ammonia is 40k ~ 50kg/h.
Preferably, in step (2), described careless ammonium phosphonic acids and the mass ratio that feeds intake of described solvent are 1:1.5 ~ 2.5.
Due to the enforcement of above technical scheme, the present invention compared with prior art has following advantage:
Purifying process of the present invention is avoided using the difficult fatty amine of removing and oxyethane, the propylene oxide of high risk, step is simple, in the careless ammonium phosphine obtained, inorganic salt content is low, purity is high, productive rate is high, and security is high, technological process for solvent, carries out neutralization reaction with ammoniacal liquor and mineral alkali with water or alcohol, meet the feature of environmental protection and economy principle, there is good industrial prospect.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further details.Should be understood that these embodiments are for illustration of ultimate principle of the present invention, principal character and advantage, and the present invention is not limited by the following examples.The implementation condition adopted in embodiment can do further adjustment according to specific requirement, and not marked implementation condition is generally the condition in normal experiment.Without indicating, " % " is mass percent, and ratio is mass ratio.
Embodiment 1
80 grams of careless ammonium phosphine hydrochloride, crude (purity about 80%) are joined in 100 grams of water, adds the ammoniacal liquor adjust ph to 1 of 25% at normal temperatures, crystallization, filter, methanol wash, dry and obtain off-white color solid 50 grams, productive rate 95%, purity 95%.
Embodiment 2
80 grams of careless ammonium phosphine hydrochloride, crude (purity about 80%) are joined in the mixed solvent (1:1) of 100 grams of first alcohol and waters, adds the aqueous sodium carbonate adjust ph to 4 of 30% at normal temperatures, crystallization, filter, methanol wash, dry and obtain off-white color solid 40 grams, productive rate 75%, purity 90%.
Embodiment 3
80 grams of careless ammonium phosphine hydrochloride, crude (purity about 80%) are joined in 100 grams of water, drips 30 grams of 30%NaOH solution adjust ph to 2 at normal temperatures, crystallization, filter, methanol wash, dry and obtain off-white color solid 49 grams, productive rate 93%, purity 93%.
Embodiment 4
80 grams of careless ammonium phosphine hydrochloride, crude (purity about 80%) are joined in 100 grams of water, at 50 DEG C, drips 30 grams of 30%KOH aqueous solution adjust ph to 3, crystallization, filter, methanol wash, dry and obtain off-white color solid 44 grams, productive rate 83%, purity 91%.
Embodiment 5
100 grams that above-mentioned technique are obtained careless ammonium phosphonic acids are suspended in 200 grams of methyl alcohol, pass into ammonia 1 hour at normal temperatures with the flow of 45kg/h, filter, and washing is dried and obtained 102 grams of careless ammonium phosphine ammonium salts, productive rate 93.5%, purity 90%.
Embodiment 6
100 grams that above-mentioned technique are obtained careless ammonium phosphonic acids are suspended in 200 grams of methanol/water (90:10), pass into ammonia 1 hour at normal temperatures with the flow of 45kg/h, filter, and washing is dried and obtained 104 grams of careless ammonium phosphine ammonium salts, productive rate 96%, purity 98%.
Embodiment 7
100 grams that above-mentioned technique are obtained careless ammonium phosphonic acids are suspended in 200 grams of methanol/water (80:20), pass into ammonia 1 hour at normal temperatures with the flow of 40kg/h, filter, and washing is dried and obtained 87 grams of careless ammonium phosphine ammonium salts, productive rate 80%, purity 98%.
Above-described embodiment is only for illustrating technical conceive of the present invention and feature; its object is to person skilled in the art can be understood content of the present invention and implement according to this; can not limit the scope of the invention with this; all equivalences done according to spirit of the present invention change or modify, and all should be encompassed within protection scope of the present invention.
Claims (10)
1. a purification process for careless ammonium phosphine, is characterized in that: comprise the steps:
Step (1), careless ammonium phosphine hydrochloride, crude to be joined in solvent, and then the aqueous solution adding alkali carries out neutralization reaction, regulate pH to 1 ~ 4.5 of reaction system, then after filtration, dry and obtain careless ammonium phosphonic acids;
Step (2), careless ammonium phosphonic acids step (1) obtained dissolve in a solvent, then pass into ammonia and carry out salt-forming reaction, separate out careless ammonium phosphine solid, then after filtration, dry and obtain highly purified careless ammonium phosphine.
2. the purification process of careless ammonium phosphine according to claim 1, is characterized in that: the purity of described careless ammonium phosphine hydrochloride, crude is 70% ~ 90%.
3. the purification process of careless ammonium phosphine according to claim 1, it is characterized in that: in step (1), described solvent is the mixed solvent of water, alcohol or water and alcohol.
4. the purification process of careless ammonium phosphine according to claim 3, is characterized in that: described alcohol is methyl alcohol or ethanol.
5. the purification process of careless ammonium phosphine according to claim 1, is characterized in that: in step (1), and the aqueous solution of described alkali is for being selected from ammoniacal liquor, the NaOH aqueous solution, the KOH aqueous solution, Na
2cO
3the aqueous solution, K
2cO
3one or more in the aqueous solution.
6. the purification process of careless ammonium phosphine according to claim 5, is characterized in that: in step (1), and the aqueous solution of described alkali is for being selected from ammoniacal liquor or the NaOH aqueous solution.
7. the purification process of careless ammonium phosphine according to claim 1, is characterized in that: in step (1), the temperature of carrying out described neutralization reaction is 10 ~ 50 DEG C.
8. the purification process of careless ammonium phosphine according to claim 1, it is characterized in that: in step (2), described solvent is the mixed solvent of water, alcohol or water and alcohol.
9. the purification process of careless ammonium phosphine according to claim 8, is characterized in that: in step (2), and described solvent is mass ratio is the water of 1:9 ~ 19 and the mixed solvent of methyl alcohol.
10. the purification process of careless ammonium phosphine according to claim 1, is characterized in that: in step (2), the temperature of carrying out described salt-forming reaction is 10 ~ 50 DEG C, and the reaction times is 0.5 ~ 2h.
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| CN201610022720.7A CN105541904B (en) | 2016-01-14 | 2016-01-14 | A kind of purification process of glufosinate-ammonium |
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| CN201610022720.7A CN105541904B (en) | 2016-01-14 | 2016-01-14 | A kind of purification process of glufosinate-ammonium |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106188134A (en) * | 2016-07-01 | 2016-12-07 | 永农生物科学有限公司 | A kind of L glufosinate-ammonium or the separation of its salt and process for purification |
| CN107434811A (en) * | 2016-05-25 | 2017-12-05 | 利尔化学股份有限公司 | A kind of method of glufosinate-ammonium purifying |
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| CN102268037A (en) * | 2011-06-15 | 2011-12-07 | 永农生物科学有限公司 | Process for purifying glufosinate-ammonium |
| CN103819503A (en) * | 2014-02-15 | 2014-05-28 | 山东滨农科技有限公司 | Glufosinate purifying technology |
| CN103827127A (en) * | 2011-09-30 | 2014-05-28 | 明治制果药业株式会社 | Method for producing glufosinate P free acid |
| CN104059102A (en) * | 2014-06-12 | 2014-09-24 | 浙江工业大学 | Method for preparing high-purity glufosinate-ammonium by adopting organic alkali deacidification method |
| CN104262391A (en) * | 2014-07-08 | 2015-01-07 | 重庆紫光化工股份有限公司 | Environmentally-friendly clean production method of high-purity glufosinate-ammonium |
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-
2016
- 2016-01-14 CN CN201610022720.7A patent/CN105541904B/en active Active
Patent Citations (6)
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| CN102268037A (en) * | 2011-06-15 | 2011-12-07 | 永农生物科学有限公司 | Process for purifying glufosinate-ammonium |
| CN103827127A (en) * | 2011-09-30 | 2014-05-28 | 明治制果药业株式会社 | Method for producing glufosinate P free acid |
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| CN104059102A (en) * | 2014-06-12 | 2014-09-24 | 浙江工业大学 | Method for preparing high-purity glufosinate-ammonium by adopting organic alkali deacidification method |
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| CN107434811A (en) * | 2016-05-25 | 2017-12-05 | 利尔化学股份有限公司 | A kind of method of glufosinate-ammonium purifying |
| CN107434811B (en) * | 2016-05-25 | 2019-04-09 | 利尔化学股份有限公司 | A kind of method of glufosinate-ammonium purifying |
| CN106188134A (en) * | 2016-07-01 | 2016-12-07 | 永农生物科学有限公司 | A kind of L glufosinate-ammonium or the separation of its salt and process for purification |
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