5994-61-6

Basic information

• Product Name: N-(Carboxymethyl)-N-(phosphonomethyl)-glycine
• Synonyms: n-(phosphonomethyl)iminodiaceticacidhydrate;n-(carboxymethyl)-n-(phosphonomethyl)-glycine;N-(PHOSPHONOMETHYL)IMINODIACETIC ACID;N-(PHOSPHONOMETHYL)IMINODIACETIC ACID MONOHYDRATE;PMIDA;N-Phosphonomethyl aminodiacetic acid;PMID;N-(PHOSPHONOMETHYL)IMINODIACETIC ACID, 9 5%
• CAS NO: 5994-61-6
• Molecular Formula: C₅H₁₀NO₇P
• Molecular Weight: 227.11
• EINECS: 227-824-5
• Product Categories: Organic Building Blocks;Phosphonic/Phosphinic Acids;Phosphorus Compounds
• Mol File: 5994-61-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: 215 °C (dec.)(lit.)
• Boiling Point: 585.9 °C at 760 mmHg
• Flash Point: 308.2 °C
• Appearance: /
• Density: 1.792 g/cm³
• Vapor Pressure: 3.01E-15mmHg at 25°C
• Refractive Index: 1.577
• PKA: 0.90±0.10(Predicted)
• BRN: 1795744
• CAS DataBase Reference: N-(Carboxymethyl)-N-(phosphonomethyl)-glycine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Carboxymethyl)-N-(phosphonomethyl)-glycine(5994-61-6)
• EPA Substance Registry System: N-(Carboxymethyl)-N-(phosphonomethyl)-glycine(5994-61-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 1
• Hazardous Substances Data: 5994-61-6(Hazardous Substances Data)

Usage

Uses

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine is used in surface modification of cobalt oxide nanoparticle to overcome any toxic effect while functioning as cancer antigen carrier.

Definition

ChEBI: A tertiary amino compound that consists of iminodiacetic acid bearing an N-phosphonomethyl substituent.

General Description

N-(Phosphonomethyl)iminodiacetic acid hydrate is the hydrated form of N-(phosphonomethyl)iminodiacetic acid (PMIDA; H4pmida). The solubility of PMIDA in various solvents and solvent mixtures has been studied. It is the starting material for the synthesis of N-(phosphonomethyl)iminodiacetate (pmida4-), a multidentate organic ligand. PMIDA undergoes molecular oxygen oxidation in the presence of metal salts to form N-(phosphonomethyl)glycine, also known as glyphosate. H4pmida forms the structural unit of various three-dimensional inorganic-organic hybrid compounds.

InChI:InChI=1/C5H10NO7P/c7-4(8)1-6(2-5(9)10)3-14(11,12)13/h1-3H2,(H,7,8)(H,9,10)(H2,11,12,13)

Synthetic route

formaldehyd (50-00-0) + iminodiacetonitrile (628-87-5) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
Stage #1: iminodiacetonitrile With sodium hydroxide In water at 45 - 50℃; for 1h; Stage #2: With phosphorus trichloride Stage #3: formaldehyd at 115 - 120℃; for 2h;	93.8%
Stage #1: iminodiacetonitrile With hydrogenchloride; sulfuric acid In water at 80 - 160℃; under 1500.15 - 15001.5 Torr; for 6h; Inert atmosphere; Autoclave; Stage #2: formaldehyd With phosphonic Acid In water for 3h; Pressure; Temperature; Inert atmosphere; Autoclave; Reflux;	90.52%

Ν,Ν-biscyanomethyl glycine (31611-66-2) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
Stage #1: Ν,Ν-biscyanomethyl glycine With methanesulfonic acid; phosphorus pentoxide In acetonitrile at 25 - 40℃; for 21h; Stage #2: With water; sodium hydroxide In acetonitrile at 90℃; for 7h; Reagent/catalyst; Time; pH-value; Temperature;	97.3%
Stage #1: Ν,Ν-biscyanomethyl glycine With phosphorus(III) oxide; methanesulfonic acid In acetonitrile at 20 - 40℃; for 21h; Stage #2: In water at 90℃; for 7h; Temperature; Time; Concentration; Reagent/catalyst;	97.3 %Spectr.

formaldehyd (50-00-0) + monosodium salt of iminodiacetic acid → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
With hydrogenchloride; phosphorous acid In water at 115 - 120℃; for 2h;	94.1%
With hydrogenchloride; phosphonic Acid In water

iminodiacetic acid hydrochloride + iminodiacetonitrile (628-87-5) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
Stage #1: iminodiacetonitrile With sodium hydroxide In water at 100 - 110℃; for 1h; Stage #2: iminodiacetic acid hydrochloride With dihydrogen peroxide; pyrographite at 80 - 100℃; for 0.5h; Stage #3: With formaldehyd; phosphoric acid at 110℃; for 3h; Reagent/catalyst;	98.5%

formaldehyd (50-00-0) + iminodiacetic acid monosodium → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
With hydrogenchloride; phosphonic Acid In water at 80 - 110℃; for 5h; Temperature;	94.2%

formaldehyd (50-00-0) + iminodiacetic acid (142-73-4) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
With hydrogenchloride; phosphorous acid In water at 100 - 120℃; under 7500.75 - 9000.9 Torr;	93.1%
With phosphonic Acid for 3h; Reflux; Green chemistry;	90.3%
Stage #1: iminodiacetic acid With phosphonic Acid In water Reflux; Stage #2: formaldehyd In water at 130 - 136℃; for 1.75h; Product distribution / selectivity;	67.3%

phosphorous acid (10294-56-1) + iminodiacetic acid (142-73-4) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
With formaldehyd; sulfuric acid	78.2%
With formaldehyd; sulfuric acid	75.3%
With formaldehyd; sulfuric acid	74.2%
With formaldehyd; sulfuric acid In water	59.8%

Ν,Ν-biscyanomethyl glycine (31611-66-2) → phosphonomethylimino-di-acetic acid (5994-61-6) + N,N-bis(cyanomethyl)aminomethylphosphonic acid (76127-84-9)

Conditions	Yield
Stage #1: Ν,Ν-biscyanomethyl glycine With methanesulfonic acid; phosphorus pentoxide In acetonitrile at 25 - 30℃; for 2h; Stage #2: With water; sodium hydroxide at 25℃; Solvent; Time; Temperature; Reagent/catalyst;	A 15.1% B 37.6%
With phosphorus(III) oxide; trifluorormethanesulfonic acid In acetonitrile at 30℃; for 3h; Reagent/catalyst; Temperature; Concentration; Time;	A 13.4 %Spectr. B 65.3 %Spectr.

N-hydroxymethylimino diacetic acid diethyl ester (1531623-12-7) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
Stage #1: N-hydroxymethylimino diacetic acid diethyl ester With methanesulfonic acid; phosphorus pentoxide; Dimethyl phosphite at 50 - 85℃; Stage #2: With water at 85℃; for 1h; Reagent/catalyst; Time; Temperature;	61%

formaldehyd (50-00-0) + 1,4-di(carboxymethyl)-2,5-diketopiperazine (77752-64-8) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
With hydrogenchloride In water	55%

1,3,5-Trioxan (110-88-3) + Diethyl iminodiacetate (6290-05-7) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
Stage #1: 1,3,5-Trioxan; Diethyl iminodiacetate With acetic acid at 80℃; for 6h; Stage #2: With phosphorus pentoxide at 20 - 80℃; for 8h; Stage #3: With water at 100℃; for 6h;	53%

formaldehyd (50-00-0) + phosphorus trichloride hydrolysate + 1,4-di(carboxymethyl)-2,5-diketopiperazine (77752-64-8) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
With hydrogenchloride	88.2%

methyl phosphonic acid monosodium chlorine + iminodiacetic acid disodium salt → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
With chlorine; sodium iodide at 80 - 90℃; for 14h;

formaldehyd (50-00-0) + monosodium salt of iminodiacetic acid + phosphorous acid (10294-56-1) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
With hydrogenchloride	97%, 91%

formaldehyd (50-00-0) + iminodiacetic acid disodium salt → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
With hydrogenchloride; phosphorus trichloride In water Product distribution / selectivity;
With hydrogenchloride; N-methyl N-phosphonomethylglycine; phosphorus trichloride In water Product distribution / selectivity;
With hydrogenchloride; phosphorus trichloride In water Product distribution / selectivity; N-(phosphonomethyl)iminodiacetic acid seeds;

disodium chloromethylphosphonate + disodium salt of bis-carboxymethyl-amine → phosphonomethylimino-di-acetic acid (5994-61-6)

phosphonomethylimino-di-acetic acid (5994-61-6) → N-(phosphonemethyl)glycine (1071-83-6)

Conditions	Yield
Calgon CENTAUR 80-100 mesh (149-177 μm) at 95℃; Product distribution / selectivity;	98.6%
Norit PK at 95℃; Conversion of starting material;	98.3%
Nuchar RGC at 95℃; Conversion of starting material;	98.9%

strontium nitrate + phosphonomethylimino-di-acetic acid (5994-61-6) → [(strontium)2(N-(phosphonomethyl)iminodiacetic acid(-4H))(H2O)]

Conditions	Yield
With 1,3-di(piperidin-4-yl)propane In ethanol; water at 180℃; for 72h; pH=3.42; Autoclave;	81.63%

phosphonomethylimino-di-acetic acid (5994-61-6) + BaCl2*4H2O → [(strontium)2(N-(phosphonomethyl)iminodiacetic acid(-2H))(HPO4)]

Conditions	Yield
With 1,3-di(piperidin-4-yl)propane In ethanol; water at 180℃; for 72h; pH=2.16; Autoclave;	80.74%

phosphonomethylimino-di-acetic acid (5994-61-6) + barium(II) hydroxide → [(barium)2(N-(phosphonomethyl)iminodiacetic acid(-2H))2(H2O)]

Conditions	Yield
With 1,3-di(piperidin-4-yl)propane In ethanol; water at 150℃; for 48h; pH=2.16; Autoclave;	78.87%

phosphonomethylimino-di-acetic acid (5994-61-6) + benzene-1,3,5-tricarboxylic acid (554-95-0) + water (7732-18-5) + magnesium oxide → [Mg15(PMIDA)6(BTC)2(H2O)12]·6H2O

Conditions	Yield
at 180℃; for 168h; pH=5; Autoclave;	77%

phosphonomethylimino-di-acetic acid (5994-61-6) + benzene-1,3,5-tricarboxylic acid (554-95-0) + cobalt(II) diacetate tetrahydrate (6147-53-1) + magnesium oxide → [Co13Mg2(PMIDA)6(BTC)2(H2O)12]·6H2O

Conditions	Yield
With ammonium hydroxide In water at 180℃; for 120h; pH=5; Autoclave;	77%

ammonium molybdate(VI) tetrahydrate + dimethylsulfite (616-42-2) + phosphonomethylimino-di-acetic acid (5994-61-6) → N-(phosphonemethyl)glycine (1071-83-6)

Conditions	Yield
With dihydrogen peroxide In water	76%

erbium(III) chloride hexahydrate + phosphonomethylimino-di-acetic acid (5994-61-6) + iron(II) oxalate dihydrate (6047-25-2) → [ErFe(III)(Fe(II))6(N-(phosphonomethyl)iminodiacetateH)6]*nH2O

Conditions	Yield
With aq. NaOH In further solvent(s) to mixt. of acid, Fe oxalate, ErCl3*6H2O added eutectic mixt. of cholinechloride and malonic acid and aq. NaOH; suspn. magnetically stirred for 1 h at ambient temp.; gel transferred to react. vessel, placed in prehe ated oven (at 150°C) for 90 h; washed 3 times with EtOH with ultrasonic vibration and with water; air dried at ambient temp.;	76%

manganese(II) chloride tetrahydrate + phosphonomethylimino-di-acetic acid (5994-61-6) → Mn(H2O)(N-(phosphonomethyl)iminodiacetate) (821780-71-6)

Conditions	Yield
With tetramethylammonium hydroxide In water High Pressure; to an aq. soln. of Mn-contg. compd. a ligand and TMAOH soln. were added with stirring; the final mixt. with a molar ratio 1 MnCl2*4H2O: 1 H4PMIDA: 4 TMAOH was crystd. in a bomb at 150°C for 5 d; the compd. was filtered and washed with distd. water; elem. anal.; detd.by powder XRD;	75%

phosphonomethylimino-di-acetic acid (5994-61-6) + benzene-1,3,5-tricarboxylic acid (554-95-0) + water (7732-18-5) + nickel(II) acetate tetrahydrate (6018-89-9) + magnesium carbonate → [Mg8Ni12(OH)12(N-(phosphonomethyl)iminodiacetic acid-H4)4(1,3,5-benzenetricarboxylic acid-H3)4(H2O)16]*9H2O

Conditions	Yield
With ammonia at 190℃; for 120h; pH=7; Temperature; pH-value;	75%

barium(II) nitrate + phosphonomethylimino-di-acetic acid (5994-61-6) + cobalt(II) diacetate tetrahydrate (6147-53-1) → [CoBa(PMIDA)(H2O)2]·H2O

Conditions	Yield
With ammonium hydroxide; benzene-1,3,5-tricarboxylic acid In water at 180℃; for 120h; pH=10; Autoclave;	73%

ammonium molybdate(VI) tetrahydrate + phosphonomethylimino-di-acetic acid (5994-61-6) → N-(phosphonemethyl)glycine (1071-83-6)

Conditions	Yield
With sulphur dichloride; dihydrogen peroxide In water	71%
With dihydrogen peroxide In water	68%

cobalt(II) chloride hexahydrate + phosphonomethylimino-di-acetic acid (5994-61-6) → [H3O]6[Co4(H2O)4(N-(phosphonomethyl)iminodiacetic acid(-4H))2(N-(phosphonomethyl)iminodiacetic acid(-3H))2]*2H2O

Conditions	Yield
With (CH3)4NOH; NH4F In ethanol High Pressure; Co salt and NH4F dissolved in EtOH; N-(phosphonomethyl)iminodiacetic acid added with vigorous stirring; Me4NOH added; molar ratio = 1:4:1:1; stirred; mixt. heated at 170°C in autoclave for 5 d; crystals filtered under vac.; washed with EtOH; dried in air; elem. anal.;	70%

fac-[ReI(OH2)3(CO)3](SO3CF3) (1356855-78-1, 811431-04-6) + phosphonomethylimino-di-acetic acid (5994-61-6) → C8H7NO10PRe(2-)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 4h; pH=Ca. 4;	68%

oxovanadium(IV) sulfate + phosphonomethylimino-di-acetic acid (5994-61-6) + sodium hydrogencarbonate (144-55-8) → 2Na(1+)*0.5V2O2(O3PCH2N(CH2CO2)2)2(4-)*5H2O=(Na4[V2O2(O3PCH2N(CH2CO2)2)2]*10H2O)0.5

Conditions	Yield
In water addn. of NaHCO3 (to pH=2 or 4) to mixt. of V-compd. and ligand, stirringat room temp. for 24 h; EtOH addn., crystn. (4°C, 1 week; two crops), collection (filtration), washing (EtOH), drying (vac.); elem. anal.;	67%

Upstream product

• 33454-80-7 N-hydroxymethyl iminodiacetic acid 
• 1531623-12-7 N-hydroxymethylimino diacetic acid diethyl ester 
• 110-88-3 1,3,5-Trioxan 
• 628-87-5 iminodiacetonitrile 
• 6290-05-7 Diethyl iminodiacetate 
• 31611-66-2 Ν,Ν-biscyanomethyl glycine 
• 50-00-0 formaldehyd 
• 10294-56-1 phosphorous acid 
• 142-73-4 iminodiacetic acid 
• 77752-64-8 1,4-di(carboxymethyl)-2,5-diketopiperazine 

Downstream Products

• 1071-83-6 N-(phosphonemethyl)glycine 
• 1066-51-9 Aminomethylphosphonic acid 
• 64-18-6 formic acid 
• 35404-71-8 N-methylaminomethanephosphonic acid 
• 84767-96-4 N-formyl-N-(phosphonomethyl)glycine 
• 68-12-2 N,N-dimethyl-formamide 
• 24569-83-3 N-methyl N-phosphonomethylglycine 
• 50-00-0 formaldehyd 
• 14265-44-2 Phosphate 

Relevant articles and documents

Recycling method for mother liquor of N-(phosphonomethyl)iminodiacetic acid

The invention relates to a recycling method for mother liquor of N-(phosphonomethyl)iminodiacetic acid. According to the invention, with iminodiacetonitrile as a main raw material, through an alkaline hydrolysis process or an acidolysis and alkaline hydrolysis combined process, ammonia gas is recycled or/and monosodium diacid salt is generated by addition of ammonium salt and double decomposition reaction of deamination under heating; a qualified sodium chloride by-product is precipitated and separated through direct hydrolysis of the mother liquor of N-(phosphonomethyl)iminodiacetic acid and common-ion effect of hydrogen chloride; acidic mother liquor can be recycled; the mother liquor, the mother liquor incapable of being reused and washing water can be completely precipitated and separated through the addition of calcium hydroxide; the obtained precipitate can regenerate raw materials and products through an aqueous solution of acid or alkali; N-(phosphonomethyl)iminodiacetic acid is reused or separately synthesized; and the regenerated calcium hydroxide can be repeatedly reused. The novel recycling method provided by the invention can realize clean production of N-(phosphonomethyl)iminodiacetic acid and cyclic utilization of by-products with high added value.

Using glycine crystallization mother liquor to produce N-phosphonomethyl glycine method (by machine translation)

The invention belongs to the technical field of agricultural chemicals, relates to a use of glycine crystallization mother liquor to produce N-phosphonomethyl-glycine is method for treating keratoconjunctival, the method is the mother liquor through the chemical reaction of glycine in completely converted into salt of iminodiacetic acid-containing mother liquor, and then the iminodiacetic acid salt mother liquor and chlorine methyl phosphine acid sodium salt reaction, to obtain N-phosphonomethyl iminodiacetic acid, obtained after the oxidation N-phosphonomethyl glycine. The method is well solved the difficult problem of glycine crystallization mother liquor treatment, the better use of the mother liquor in the glycine residue and its by-product iminodiacetic acid production N-phosphonomethyl glycine, three waste resource, create social benefits and economic benefits; intermediate product generated by this method without the need of separation and purification, does not need to remove inorganic salt, the reaction procedures simplified, the cost saving is even more; in addition the method of the present invention, the whole reaction process is not a large amount of waste liquid produced, also produced of non-formaldehyde, is friendly to the environment. (by machine translation)

Glyphosate alkaline mother liquor processing method

The invention discloses a treatment method of a glyphosate alkaline mother solution, which comprises the following steps that: a hydrochloric acid is added to the mother solution to adjust the pH of the solution to 1-5 to obtain a solution A; the solution A is subjected to membrane separation to obtain a solution B and a sodium chloride solution, and the sodium chloride solution is evaporated to obtain a saturated solution; and the saturated sodium chloride solution is subjected to the Hou soda process to obtain sodium carbonate to be recycled. The treatment method is characterized in that the solution B is concentrated to make the concentration of a solute in the solution B increase to 3-10 times, i.e. a solution C, and then the appropriate amount of glycine and formaldehyde is added to the solution C, so that glyphosate and phosphorous acid in the solution C are reacted completely to obtain glyphosine and the original glyphosine in the solution C; and the glyphosine is neutralized, leached and dried and the like to obtain a glyphosine solid to be recycled. The treatment method has the advantages that the glyphosate, the glyphosine, sodium hypophosphite and the sodium chloride in the glyphosate alkaline mother solution are fully recycled, the waste is reduced, the pollution is reduced, and the utilization rate of the alkaline mother solution is improved.