MXPA98000628A - Procedure for the preparation of n-fosfonometilglic - Google Patents
Procedure for the preparation of n-fosfonometilglicInfo
- Publication number
- MXPA98000628A MXPA98000628A MXPA/A/1998/000628A MX9800628A MXPA98000628A MX PA98000628 A MXPA98000628 A MX PA98000628A MX 9800628 A MX9800628 A MX 9800628A MX PA98000628 A MXPA98000628 A MX PA98000628A
- Authority
- MX
- Mexico
- Prior art keywords
- glyphosate
- salt
- mixture
- process according
- ions
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title description 3
- XDDAORKBJWWYJS-UHFFFAOYSA-N Glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims abstract description 67
- 239000005562 Glyphosate Substances 0.000 claims abstract description 47
- 229940097068 glyphosate Drugs 0.000 claims abstract description 47
- 239000011780 sodium chloride Substances 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052742 iron Inorganic materials 0.000 claims abstract description 14
- 150000002500 ions Chemical class 0.000 claims abstract description 12
- -1 Iron ions Chemical class 0.000 claims abstract description 7
- 238000007792 addition Methods 0.000 claims abstract description 6
- 239000002244 precipitate Substances 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 5
- 229910000460 iron oxide Inorganic materials 0.000 claims description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N Iron(III) oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002505 iron Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229960004887 ferric hydroxide Drugs 0.000 claims description 2
- MSNWSDPPULHLDL-UHFFFAOYSA-K iron(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Fe+3] MSNWSDPPULHLDL-UHFFFAOYSA-K 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- NCNCGGDMXMBVIA-UHFFFAOYSA-L Iron(II) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000005755 formation reaction Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 235000014413 iron hydroxide Nutrition 0.000 description 5
- RUTXIHLAWFEWGM-UHFFFAOYSA-H Iron(III) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 4
- 229940032950 ferric sulfate Drugs 0.000 description 4
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- 230000001419 dependent Effects 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- 230000003311 flocculating Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000002363 herbicidal Effects 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940032296 ferric chloride Drugs 0.000 description 1
- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 1
- 229910001447 ferric ion Inorganic materials 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
Abstract
N- (phosphonomethylglycine) (glyphosate) or a salt or ionic form thereof is removed from an aqueous mixture as an effluent stream where it is present through the addition to the mixture of ions capable of forming a salt of glyphosate of insoluble or partially soluble complex, and remove the complex salt of the mixture. Iron ions (III) are particularly suitable. In a preferred integral process, glyphosate is recovered from the glyphosate salt of comple
Description
PROCEDURE FOR THE PREPARATION OF N-PHOSPHONOMETHYLGLYCINE
DESCRIPTION OF THE INVENTION
The present invention relates to processes for the preparation of N-phosphonomethylglycine (glyphosate), a broad-spectrum herbicide, which is widely used throughout the world. In particular, the invention relates to means for reducing the amount glyphosate, which is expelled with the effluent from manufacturing processes. There are several well known manufacturing routes through which glyphosate can be prepared, for example the routes established in US 3,969,398, US 3, 799, 758, US 3,927,080, US 4,237,065 and US 4,065,491, but all these routes have a problem. common. This is, however, an efficient procedure, usually there will be some waste of the product. Potentially, the presence of glyphosate in effluent can present environmental problems due to its herbicidal properties. The waste of the product is, of course, also undesirable from the point of view of the manufacturer who wishes to produce glyphosate as economically as possible and, for all these reasons, it is essential that little product be expelled with effluent from the plant.
EP-A-0323821 addresses the problem of treating the waste stream from a glyphosate plant and suggests the solution of contacting the waste stream with a transition metal catalyst in a mixture or solution. The mixture or solution should be contacted with a gas containing molecular oxygen and the reaction mass heated to a temperature sufficient to initiate and sustain the oxidation reactions of the phosphonomethylglycine derivatives. This process has the disadvantage, however, that it is expensive since the catalyst, when making contact with the molecular oxygen-containing gas and the heating add cost. In addition, the reaction should usually be conducted at elevated pressure which, again, increases the costs of the treatment procedure. The present invention relates to an efficient and cost-effective process for removing glyphosate or a salt or derivative thereof from a mixture in which it is present, wherein the mixture is the effluent of a glyphosate manufacturing process. In a first aspect of the present invention, there is provided a process for removing N- (phosphonomethylglycine) (glyphosate) or a salt or ionic form thereof from an aqueous mixture in which it is present, wherein the aqueous mixture is an effluent of A method of manufacturing glyphosate, the process comprises adding to the mixture ions capable of forming a glyphosate salt of insoluble or partially soluble complex, and removing the complex salt from the mixture. Examples of water-soluble salts of glyphosate include the sodium salts (for example monosodium and disodium salts), potassium, ammonium, trimethylsulfonium and isopropylammonium. The ionic forms of glyphosate include the protonated form of zwitterion. When the ions are added to an aqueous mixture containing glyphosate, the inventors of the present short form a complex salt. The complex salt is insoluble in water and precipitates in the solution. The ions added to the mixture can be iron ions (11), calcium, magnesium or aluminum. However, iron ions (III) are preferred since they form at least soluble complex salts which are, therefore, very easily removed. The formation and / or solubility of the complex salt may be pH dependent and, usually, acidic or neutral conditions may be required. In the case of iron (III), the pH of the mixture containing glyphosate can be adjusted to a pH of 6 or less before the addition of the iron salt (III). It is preferred that the pH be from 1 to 4, for example about pH 3.
The ions, which are added to the glyphosate-containing mixture, will preferably be added to the form of a water-soluble salt. As, as mentioned above, the formation of the complex salt appears to be pH dependent, the salt must be one which is soluble in acidic solutions, for example, a pH of 5 or less. In the case of iron (III), the soluble salt may be, for example, sulfate, chloride or hydroxide. The formation of salts of glyphosate complex with metal ions has been observed, for example, by Hensley et al, (Weed Research 18, 293-297 (1978)) and the salts of glyphosate complex with iron (III) have been discussed by MacBride et al. Soil Sci. Soc. Am. J. 53, 1668-1673. However, the effect does not seem to have been perceived as useful or in any industrial use. The structure of the complex salts is not completely clear but, in the case of iron (11), a complex salt is formed that appears to contain a 1: 1 ratio of glyphosate and iron (III), which is insoluble in water and seems to precipitate out of the solution almost quantitatively at room temperature. Once formed, the precipitate that contains glyphosate can be removed through any suitable method, some of the simplest and most effective methods are filtration and centrifugation. In order to assist the separation process, it can be an advantage to employ a flocculating surfactant in this step. Suitable flocculating surfactants are well known and readily available to those skilled in the art. In this way, the process of the present invention allows the glyphosate to be removed from the effluent of a glyphosate manufacturing process, and this may have extremely beneficial environmental effects, since the release of the glyphosate with the effluent can be avoided. Of course, it is preferred from the manufacturer's point of view whether glyphosate can be removed from the precipitate and the inventors hereby also advise a method to achieve this object once the glyphosate salt fraction of the complex has been separated. , this can be used to form an alkaline aqueous suspension. The increase in pH causes the decomposition of the glyphosate salt of the complex to give a soluble glyphosate salt, and when iron (lll) is used as the counterion, the precipitation of the iron hydroxide (III) and the iron oxide ( III) hydrated. In this way this method is particularly advantageous since it not only allows the recovery of glyphosate in a form that can be recombined with glyphosate produced in the manufacturing process, but also ensures that the iron (III), which was originally used for precipitate the glyphosate, has been recovered in a form in which it can be converted to a soluble iron salt (III) and reused in the process of the effluent treatment of the invention. In general, the pH of the suspension will be greater than 8, but it is more usual for a higher pH, for example 12 above it, to be used. Typically, the suspension will have a pH of about 12.2-12.8, usually around 12.4. The rise in the pH of the mixture causes the formation of iron hydroxide (III) or hydrated iron oxide, which can then be removed from the mixture by any appropriate method. The suspension can be formed in two stages: first, water can be added to the precipitate and mixed to form a suspension and subsequently, a base can be added to the mixture. However, in an alternative procedure, the glyphosate-containing complex salt can be added directly to an alkaline solution. In general, this will have the advantage of giving a more concentrated glyphosate solution. In any process, the suspension can be formed at room temperature. Any base can be used to raise the pH of the solution, but the bases that result in the formation of a water-soluble glyphosate salt are particularly suitable, since the separation of iron hydroxide (l l l) from glyphosate is then made much easier. Examples of especially suitable bases include sodium and potassium hydroxide. In order to keep the amount of solution at a minimum, it is preferred that the base be relatively concentrated. Conveniently, the base will be a commercially available base, for example, 50% w / w sodium hydroxide. The iron hydroxide (11) can be removed from the mixture through a variety of known methods, but one particularly suitable is centrifugation. Once the iron hydroxide (11 I) has been removed from the process, the aqueous solution of the glyphosate salt can be recombined with the product of the main part of the process. The process of the present invention can be operated either as an intermittent procedure or as a continuous process. Now the invention will be further illustrated through the following non-limiting examples.
EXAMPLE 1
Formation of a salt of glyphosate complex through the addition of ferric sulfate to a solution containing glyphosate An aqueous solution (300 ml) containing 1% w / w of phosphonomethyl glycine and 20% w / w of sodium chloride , with a total organic carbon content estimated at 1 310 mg / l, treated with 7.2 g of a 50% w / w ferric sulfate solution, the pH being maintained between 0.9 and 1.1 using a sodium hydroxide solution. After removing the precipitate by filtration, it was found that the total organic carbon content of the liquors is 60 mg / l.
EJ EM PLO 2
Formation of a glyphosate complex salt through the addition of ferric chloride to a solution containing glyphosate. An aqueous solution as described in the example
1 above (300 ml), treated with 7.7 g of a 50% w / w solution of ferric chloride hexahydrate, the pH of the suspension being maintained at 1.0 using a sodium hydroxide solution. After removing the precipitate through filtration, it was estimated that the total organic carbon content of the filtrates is 70 mg / l.
EXAMPLE 3
Recovery of glyphosate A typical process effluent containing N-phosphonomethylglycine (119.7 g to 1.35% w / w) was treated with an aqueous solution of ferric sulfate (9.0 g to 45% w / w), maintaining the pH at 4.0 through the addition of 47% of a sodium hydroxide solution. The resulting precipitate was filtered and formed into a suspension with a sodium hydroxide solution (38.4 g to 23.5% w / w), for one hour at a pH of 12.7. The removal of the hydrous ferrous oxide hydroxide (ferric hydroxide) through filtration produced a pale yellow solution, which was found, through high performance liquid chromatography, containing 71.8% of the phosphonomethylglycine present in the original sample .
EXAMPLE 4
Ferric Ion Recirculation The hydrated ferric oxide of Example 3 is charged to an additional 120 g portion of the process effluent at a pH of 1.3, together with the freshly prepared ferric sulfate solution (1.8 g to 45%), and used to precipitate the phosphonomethylglycine from this solution. Thus, the method of the present invention has the advantages that it ensures a high rate of recovery of the glyphosate from a solution containing a soluble glyphosate salt and, particularly when an iron salt has been used (11). to precipitate glyphosate, it allows a high recovery of iron (III), which can then be recirculated and reused to recover more glyphosate. The method of the invention, therefore, provides an economical way to remove glyphosate from the effluent where it is present, which, unlike the prior art processes, does not involve the use of expensive reagents or severe reaction conditions such as high temperature and pressure.
Claims (11)
1 . A process for removing N- (phosphonomethylglycine) (glyphosate) or a salt or an ionic form thereof from an aqueous mixture where it is present, wherein the aqueous mixture is an effluent from a process for making glyphosate, the process is characterized in that it comprises adding to the mixture, ions capable of forming a complex and soluble or partially soluble glyphosate salt, and removing the complex salt from the mixture.
2. The process according to claim 1, characterized in that the ions are calcium, magnesium, aluminum or iron ions (III) .-
3. The process according to claim 2, characterized in that the ions are iron ions (III) and the pH of the glyphosate-containing mixture is adjusted to a pH of 6 or less before the addition of the iron salt (III). .
4. The process according to claim 3, characterized in that the pH of the mixture is adjusted from 1 to 4, for example a pH of about 3.
5. The method according to any of claims 1 to 4, characterized in that the ions are added in the form of a salt, which is soluble in an aqueous solution at the pH of the mixture containing the glyphosate.
6. The process according to claim 5, further characterized in that the ion is iron (11) and the soluble salt is the sulfate, chloride or hydroxide.
7. The process according to claim 1, or claim 2, characterized in that the precipitate is removed by filtration or centrifugation.
8. The process according to any of claims 2 to 7, characterized in that the ions capable of forming a glyphosate salt of insoluble or partially soluble complex are iron ions (III), which further comprises recovering glyphosate from the precipitate of the salt of complex through a process comprising forming an aqueous suspension of the above having a pH greater than 8 and removing the resulting ferric hydroxide or hydrated ferric oxide from the suspension to give an aqueous solution containing glyphosate.
9. The process according to claim 8, characterized in that the pH of the suspension is above a pH of 12.
10. The process according to claim 8 or 9, characterized in that the suspension is formed by adding water to the precipitate and subsequently adding a base or adding the precipitate to an aqueous solution of the base. eleven . The process according to claim 10, characterized in that the base is an alkali metal hydroxide.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9515265.8 | 1995-07-25 | ||
| GBGB9515265.8A GB9515265D0 (en) | 1995-07-25 | 1995-07-25 | Chemical process |
| PCT/GB1996/001548 WO1997005149A1 (en) | 1995-07-25 | 1996-06-27 | Process for the preparation of n-phosphonomethyglycine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MXPA98000628A true MXPA98000628A (en) | 1998-04-01 |
| MX9800628A MX9800628A (en) | 1998-04-30 |
Family
ID=10778236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX9800628A MX9800628A (en) | 1995-07-25 | 1996-06-27 | Process for the preparation of n-phosphonomethyglycine. |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5898082A (en) |
| EP (1) | EP0842182B1 (en) |
| JP (1) | JP3667345B2 (en) |
| KR (1) | KR100438851B1 (en) |
| CN (1) | CN1068007C (en) |
| AT (1) | ATE208781T1 (en) |
| AU (1) | AU701535B2 (en) |
| BG (1) | BG63696B1 (en) |
| BR (1) | BR9609692A (en) |
| CA (1) | CA2224522C (en) |
| CZ (1) | CZ291133B6 (en) |
| DE (1) | DE69617020T2 (en) |
| DK (1) | DK0842182T3 (en) |
| ES (1) | ES2163029T3 (en) |
| GB (1) | GB9515265D0 (en) |
| HU (1) | HU219316B (en) |
| IL (1) | IL123022A (en) |
| MX (1) | MX9800628A (en) |
| MY (1) | MY113506A (en) |
| NO (1) | NO322972B1 (en) |
| NZ (1) | NZ311119A (en) |
| PL (1) | PL184805B1 (en) |
| RO (1) | RO119720B1 (en) |
| RU (1) | RU2159247C2 (en) |
| SK (1) | SK282217B6 (en) |
| TR (1) | TR199800114T1 (en) |
| TW (1) | TW332207B (en) |
| WO (1) | WO1997005149A1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10007702A1 (en) | 2000-02-19 | 2001-08-23 | Sueddeutsche Kalkstickstoff | Process for the preparation of N- (phosphonomethyl) glycine |
| DE60115019T2 (en) * | 2000-05-22 | 2006-08-03 | Monsanto Technology Llc. | REACTION SYSTEMS FOR THE PREPARATION OF N- (PHOSPHONOMETHYL) GLYCINE COMPOUNDS |
| BRPI0514527B1 (en) | 2004-08-19 | 2014-12-02 | Monsanto Technology Llc | Herbicidal composition, batch process for preparing a glyphosate salt solution, continuous process for preparing a finished composition in the form of a glyphosate salt solution and tank mix herbicidal composition |
| CN102775012B (en) * | 2012-07-18 | 2014-07-02 | 常州大学 | Method for removing high concentration phosphorus in glyphosate wastewater |
| CN103351070B (en) * | 2013-07-26 | 2015-05-06 | 闽南师范大学 | Method for treating glyphosate waste water |
| US9868650B2 (en) | 2015-12-21 | 2018-01-16 | International Business Machines Corporation | Method for removing glyphosate from a solution using functionalized polymeric nanoparticles |
| CN106277249A (en) * | 2016-08-29 | 2017-01-04 | 南京工业大学 | A kind of method removing waste water glyphosate |
| CN114933289B (en) * | 2022-06-22 | 2024-03-15 | 四川福思达生物技术开发有限责任公司 | Co-production process for glyphosate and ferric phosphate |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5735720B2 (en) * | 1973-05-17 | 1982-07-30 | ||
| US4033896A (en) * | 1976-06-18 | 1977-07-05 | Monsanto Company | Method of corrosion inhibition and compositions therefor |
| US4481026A (en) * | 1982-11-16 | 1984-11-06 | Stauffer Chemical Company | Aluminum N-phosphonomethylglycine and its use as a herbicide |
| US4472189A (en) * | 1982-12-27 | 1984-09-18 | Stauffer Chemical Co. | Stannic N-phosphonomethyglycine and its use as a herbicide |
| US4851131A (en) * | 1987-12-31 | 1989-07-25 | Monsanto Company | Process for treating glyphosate process waste streams |
| US5087740A (en) * | 1989-08-17 | 1992-02-11 | Monsanto Company | Process for purifying N-phosphonomethylglycine |
| GB9423254D0 (en) * | 1994-11-16 | 1995-01-04 | Zeneca Ltd | Process |
-
1995
- 1995-07-25 GB GBGB9515265.8A patent/GB9515265D0/en active Pending
-
1996
- 1996-06-27 EP EP96920995A patent/EP0842182B1/en not_active Expired - Lifetime
- 1996-06-27 HU HU9900146A patent/HU219316B/en not_active IP Right Cessation
- 1996-06-27 ES ES96920995T patent/ES2163029T3/en not_active Expired - Lifetime
- 1996-06-27 PL PL96324617A patent/PL184805B1/en unknown
- 1996-06-27 NZ NZ311119A patent/NZ311119A/en not_active IP Right Cessation
- 1996-06-27 MX MX9800628A patent/MX9800628A/en unknown
- 1996-06-27 KR KR10-1998-0700566A patent/KR100438851B1/en not_active IP Right Cessation
- 1996-06-27 TR TR1998/00114T patent/TR199800114T1/en unknown
- 1996-06-27 SK SK99-98A patent/SK282217B6/en not_active IP Right Cessation
- 1996-06-27 AU AU62362/96A patent/AU701535B2/en not_active Ceased
- 1996-06-27 RU RU98103267/04A patent/RU2159247C2/en not_active IP Right Cessation
- 1996-06-27 CA CA002224522A patent/CA2224522C/en not_active Expired - Fee Related
- 1996-06-27 CN CN96195811A patent/CN1068007C/en not_active Expired - Lifetime
- 1996-06-27 IL IL12302296A patent/IL123022A/en not_active IP Right Cessation
- 1996-06-27 DK DK96920995T patent/DK0842182T3/en active
- 1996-06-27 BR BR9609692A patent/BR9609692A/en not_active IP Right Cessation
- 1996-06-27 JP JP50730397A patent/JP3667345B2/en not_active Expired - Fee Related
- 1996-06-27 AT AT96920995T patent/ATE208781T1/en active
- 1996-06-27 CZ CZ1998206A patent/CZ291133B6/en not_active IP Right Cessation
- 1996-06-27 US US08/983,112 patent/US5898082A/en not_active Expired - Lifetime
- 1996-06-27 WO PCT/GB1996/001548 patent/WO1997005149A1/en active IP Right Grant
- 1996-06-27 RO RO98-00106A patent/RO119720B1/en unknown
- 1996-06-27 DE DE69617020T patent/DE69617020T2/en not_active Expired - Fee Related
- 1996-07-03 TW TW085108054A patent/TW332207B/en not_active IP Right Cessation
- 1996-07-23 MY MYPI96003026A patent/MY113506A/en unknown
-
1998
- 1998-01-23 NO NO19980312A patent/NO322972B1/en not_active IP Right Cessation
- 1998-02-10 BG BG102240A patent/BG63696B1/en unknown
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