CN100372857C - Production process of N-phosphono methyl glycine - Google Patents
Production process of N-phosphono methyl glycine Download PDFInfo
- Publication number
- CN100372857C CN100372857C CNB200410014897XA CN200410014897A CN100372857C CN 100372857 C CN100372857 C CN 100372857C CN B200410014897X A CNB200410014897X A CN B200410014897XA CN 200410014897 A CN200410014897 A CN 200410014897A CN 100372857 C CN100372857 C CN 100372857C
- Authority
- CN
- China
- Prior art keywords
- reaction
- phosphonomethyl
- glycine
- formaldehyde
- glyphosate
- 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.)
- Expired - Lifetime
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- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000005562 Glyphosate Substances 0.000 claims abstract description 10
- 229940097068 glyphosate Drugs 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 229910052742 iron Inorganic materials 0.000 claims abstract description 4
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000012452 mother liquor Substances 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- -1 alcohol compound Chemical class 0.000 claims description 4
- 150000003672 ureas Chemical class 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 3
- 235000013877 carbamide Nutrition 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000005191 phase separation Methods 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
Abstract
The present invention discloses a method for producing N-phosphono-methyl glycine, which is characterized in that N-phosphono methyliminodiacetic acid reacts with the oxygen in order to generate N-phosphono-methyl glycine under the condition that a carbon catalyst containing Mn, Fe, Co or Ni exists. The present invention uses the catalyst and oxidizing agents to control the degree of oxidation, and target products have favorable selectivity and high yield; formaldehyde is a reaction system is eliminated to stabilize the quality of glyphosate or glyphosate salt; impurities in the reaction system are eliminated, reaction mother liquid can be repeatedly used for 5 to 6 times, and the prepared solid glyphosate not only has low energy consumption, but also has high yield.
Description
Technical field:
The present invention relates to a kind of production method of glyphosate.
Background technology:
Existing glyphosate production technology generally adopts oxygenatedchemicals to make oxygenant (routine H
2O
2, NaClO etc.), though easy to use, cost height, and oxidation products complexity have more amount formaldehyde, formic acid by product in the reaction liquid phase, cause glyphosate and salt thereof to store quality problems such as instability, and the oxidation poor selectivity of PMIDA.
Summary of the invention:
The object of the present invention is to provide the production method of the N-(phosphonomethyl) glycine that a kind of target product selectivity is good, yield is high.
Technical solution of the present invention is:
A kind of production method of N-(phosphonomethyl) glycine; its feature: with N-phosphonomethyliminoacidetic acidetic solution in the presence of the Pd/carbon catalyst that contains Mn, Fe, Co, Cu or Ni; with oxygenous gas reaction, generate the N-(phosphonomethyl) glycine, reaction formula is:
The concentration of N-phosphonomethyliminoacidetic acidetic is 3～50% in the N-phosphonomethyliminoacidetic acidetic solution, and oxygen concentration is 5～97%V/V in the oxygenous gas.Temperature of reaction is 20～300 ℃, and pressure is 0.1～20MPa.After reaction was finished, gaseous product discharged, and the solid phase separation obtains high purity glyphosate, and formaldehyde in the reaction mother liquor is removed.The concrete grammar of removing formaldehyde is: the alcohol compound or the carbamide compounds of adding and formaldehyde reaction in the liquid phase of reaction mother liquor, and remove this reaction product.Described alcohol compound is methyl alcohol or ethanol, and carbamide compounds is a urea.
The present invention makes target product selectivity good, the yield height by catalyzer and oxygenant controlled oxidation degree; By removal, make glyphosate or its salt steady quality to formaldehyde in the reaction system; By removing of impurity in the reaction system abandoned, reaction mother liquor can be applied mechanically 5～6 times, and not only energy consumption is low to produce solid glyphosate, and the yield height.
The invention will be further described below in conjunction with embodiment.
Embodiment:
Embodiment:
A kind of production method of N-(phosphonomethyl) glycine; the N-phosphonomethyliminoacidetic acidetic solution that with concentration is 3～50% (examples 3%, 10%, 30%, 50%) is containing in the presence of Mn (or Fe, Co, one of Cu, Ni) Pd/carbon catalyst; with oxygenous concentration be the gas reaction of 5～97% (V/V) (example 5%, 25%, 55%, 75%, 97%); generate the N-(phosphonomethyl) glycine, reaction formula is:
Temperature of reaction is 20～300 ℃ (20 ℃, 100 ℃, 200 ℃, 300 ℃ of examples), and pressure is 0.1～20MPa (routine 0.1MPa, 3MPa, 10MPa, 15MPa, 20MPa).After reaction was finished, gaseous product discharged, and solid phase is separated, and promptly obtains high purity glyphosate.Add in the reaction mother liquor and the methyl alcohol of formaldehyde reaction (or ethanol, urea), and adopt ordinary method to remove this reaction product, reaction mother liquor is back to reaction system.
Claims (3)
1. the production method of a N-(phosphonomethyl) glycine; it is characterized in that: with N-phosphonomethyliminoacidetic acidetic solution in the presence of the Pd/carbon catalyst that contains Mn, Fe, Co, Cu or Ni; with oxygenous gas reaction, generate the N-(phosphonomethyl) glycine, reaction formula is:
Wherein the concentration of N-phosphonomethyliminoacidetic acidetic is 3～50% in the N-phosphonomethyliminoacidetic acidetic solution, and oxygen concentration is 5～97%V/V in the oxygenous gas; Temperature of reaction is 20～300 ℃, and pressure is 0.1～20MPa; After reaction was finished, gaseous product discharged, and the solid phase separation obtains high purity glyphosate, and formaldehyde in the reaction mother liquor is removed.
2. the production method of N-(phosphonomethyl) glycine according to claim 1 is characterized in that: the concrete grammar of removing formaldehyde is: the alcohol compound or the carbamide compounds of adding and formaldehyde reaction in the liquid phase of reaction mother liquor, and remove this reaction product.
3. the production method of N-(phosphonomethyl) glycine according to claim 2 is characterized in that: alcohol compound is methyl alcohol or ethanol, and carbamide compounds is a urea.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200410014897XA CN100372857C (en) | 2004-05-12 | 2004-05-12 | Production process of N-phosphono methyl glycine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200410014897XA CN100372857C (en) | 2004-05-12 | 2004-05-12 | Production process of N-phosphono methyl glycine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1609111A CN1609111A (en) | 2005-04-27 |
| CN100372857C true CN100372857C (en) | 2008-03-05 |
Family
ID=34763303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB200410014897XA Expired - Lifetime CN100372857C (en) | 2004-05-12 | 2004-05-12 | Production process of N-phosphono methyl glycine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100372857C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101353358B (en) * | 2008-09-05 | 2011-01-19 | 江苏好收成韦恩农化股份有限公司 | Method for preparing N-(phosphonomethyl) glycine with improved reaction system |
| CN102241703B (en) * | 2011-05-07 | 2014-05-07 | 安徽国星生物化学有限公司 | Improved method for preparing glyphosate from N-phosphonomethyl aminodiacetic acid |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969398A (en) * | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| CN1032784A (en) * | 1987-10-26 | 1989-05-10 | 孟山都公司 | Produce the method for N-phosphonomethylglycine |
| CN1041365A (en) * | 1988-09-26 | 1990-04-18 | 孟山都公司 | The production method of N-(phosphonomethyl) glycine |
| CN1298322A (en) * | 1998-02-25 | 2001-06-06 | 孟山都公司 | Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
| CN1308633A (en) * | 1998-07-06 | 2001-08-15 | 辛根塔参与股份公司 | Preparation of N-phosphonomethylglycine salts |
| CN1362962A (en) * | 1999-07-23 | 2002-08-07 | 巴斯福股份公司 | Method of producing glyphosate or a salt thereof |
| WO2003068387A1 (en) * | 2002-02-14 | 2003-08-21 | Monsanto Technology Llc | Oxidation catalyst and process for its preparation and process for oxidation using it |
-
2004
- 2004-05-12 CN CNB200410014897XA patent/CN100372857C/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969398A (en) * | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| CN1032784A (en) * | 1987-10-26 | 1989-05-10 | 孟山都公司 | Produce the method for N-phosphonomethylglycine |
| CN1041365A (en) * | 1988-09-26 | 1990-04-18 | 孟山都公司 | The production method of N-(phosphonomethyl) glycine |
| CN1298322A (en) * | 1998-02-25 | 2001-06-06 | 孟山都公司 | Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
| CN1308633A (en) * | 1998-07-06 | 2001-08-15 | 辛根塔参与股份公司 | Preparation of N-phosphonomethylglycine salts |
| CN1362962A (en) * | 1999-07-23 | 2002-08-07 | 巴斯福股份公司 | Method of producing glyphosate or a salt thereof |
| WO2003068387A1 (en) * | 2002-02-14 | 2003-08-21 | Monsanto Technology Llc | Oxidation catalyst and process for its preparation and process for oxidation using it |
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| Publication number | Publication date |
|---|---|
| CN1609111A (en) | 2005-04-27 |
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Owner name: JIANGSU HAOSHOUCHENG WEIENNONGHUA CO., LTD. Free format text: FORMER NAME OR ADDRESS: JIANGSU HAOSHOUCHENG WIEN PESTICIDE CHEMICAL CO., LTD. |
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Address after: Old Kai, Qidong, Jiangsu, Donggang Patentee after: JIANGSU GOOD HARVEST-WEIEN AGROCHEMICAL Co.,Ltd. Address before: Old Kai, Qidong, Jiangsu, Donggang Patentee before: JJiangsu Good-harvest Weien Agrochemical Co.,Ltd. |
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Granted publication date: 20080305 |