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

• 50-00-0 formaldehyd 
• 142-73-4 iminodiacetic acid 
• 10294-56-1 phosphorous acid 
• 77752-64-8 1,4-di(carboxymethyl)-2,5-diketopiperazine 
• 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 

Downstream Products

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

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.

New process for clean production of pmida and cyclic utilization of byproducts

The invention relates to a new process for clean production of pmida and cyclic utilization of byproducts. According to the new process, iminodiacetonitrile serves as a main raw material, ammonia gas or/and a regenerated diacid monosodium salt are recovered by an alkaline hydrolysis or acid hydrolysis and alkaline hydrolysis coordinating process and an ammonium salt added and heating deamination double decomposition reaction, a qualified sodium chloride byproduct is precipitated and separated through the direct hydrolysis of pmida mother liquor and the common-ion effect of hydrogen chloride, acidic mother liquor can be cyclically applied mechanically, mother liquor, mother liquor, which cannot be applied mechanically, and washing water can be completely precipitated and separated through adding calcium hydroxide, raw materials and products can be regenerated from precipitates by an aqueous solution of acid or alkali, the precipitates are applied mechanically or are used for independently synthesizing the pmida, and regenerated calcium hydroxide can be repeatedly applied mechanically. According to the new process, the clean production of the pmida and the cyclic and high-added-value utilization of the byproducts can be realized.

A method for synthesizing pmida (by machine translation)

The invention discloses a synthesis method of N-(Phosphonomethyl) iminodiacetic acid (PMIDA) using iminodiacetonitrile as the raw material. The method comprises the following steps: using mixed acid as a hydrolytic reagent, hydrolyzing the iminodiacetonitrile in the mixed acid water solution to obtain acid salt of the iminodiacetic acid, and then performing the condensation reaction of the hydrolyzation solution with phosphorous acid and formaldehyde at the presence of hydrochloric acid to obtain the N-(Phosphonomethyl) iminodiacetic acid, wherein the mixed acid is hydrochloric acid and sulfuric acid, or hydrochloric acid and orthophosphorous acid. According to the invention, the mixed acid is used as a hydrolytic reagent; meanwhile, high temperature and high pressure are adopted to enable the hydrolyzation to be more thorough; at the same time, no waste gas is emitted; and the periodic time of the whole synthesis process is short, the operation is simple, the utilization ratio of the raw materials is high, the side product is few, energy consumption is low and the three wastes are less.