15827-60-8

Basic information

• Product Name: Diethylenetriaminepenta(methylene-phosphonic acid)
• Synonyms: dtpmp;DIETHYLENETRIAMINEPENTAKIS(METHYLPHOSPHONIC ACID);DIETHYLENE TRIAMINE PENTA(METHYLENE PHOSPHONIC ACID);DEQUEST(R) 2060;Diethylenetriamine,pentamethylenepentaphosphonicacid;diethylenetriaminepenta(methylenephosphonic);diethylenetriaminepenta(methylphosphonicacid);diethylenetriaminepentakis(methylphos-phonicacid)sol.
• CAS NO: 15827-60-8
• Molecular Formula: C₉H₂₈N₃O₁₅P₅
• Molecular Weight: 573.2
• EINECS: 239-931-4
• Product Categories: Organics;Phosphonate antiscalant;Water treatment
• Mol File: 15827-60-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 1003.3 °C at 760 mmHg
• Flash Point: 560.6 °C
• Appearance: amber viscous liquid
• Density: 1.35 (50% aq.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Aqueous Base (Sparingly), Water
• PKA: 0.59±0.10(Predicted)
• Water Solubility: 500g/L at 25℃
• BRN: 2068968
• CAS DataBase Reference: Diethylenetriaminepenta(methylene-phosphonic acid)(CAS DataBase Reference)
• NIST Chemistry Reference: Diethylenetriaminepenta(methylene-phosphonic acid)(15827-60-8)
• EPA Substance Registry System: Diethylenetriaminepenta(methylene-phosphonic acid)(15827-60-8)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-51/53-41-37/38
• Safety Statements: 26-36-33-28-23-16-9-39
• RIDADR: UN 1789 8/PG 2
• Hazardous Substances Data: 15827-60-8(Hazardous Substances Data)

Usage

Chemical Properties

DTPMP is normally delivered as salts, because the acid form has very limited solubility in water and tends to crystallize in concentrated aqueous solutions. It is a nitrogenous organic polyphosphonic acid. It shows very good inhibition of the precipitation of barium sulfate (BaSO4). At high alkali and high temperature (above 210 °C) environments DTPMPA has better scale and corrosion inhibition effect than other phosphonates.

Uses

Different sources of media describe the Uses of 15827-60-8 differently. You can refer to the following data:
1. The phosphonate Diethylenetriaminepenta(methylenephosphonic acid) is a wastewater pollutant, and a component of phosphorous-containing nanoparticles and materials, such as in the preparation of chitosan nanoparticles for plutonium pulmonary decorporation.
2. Diethylenetriaminepentakis(methylphosphonic acid) solution is suitable for use in a study to investigate the dynamics and kinetics of sodium sulfate crystallization in the presence of various organophosphonic acids. It may be employed as ligand for the characterization of Ce3+ complexes by luminescence spectroscopy.

Advantages

DETMP is an excellent threshold scale inhibitor for carbonate, sulfate and phosphate scales. It inhibits scale formation at extremely low (ppm) dosage levels, sub-stoichiometric concentrations calculated on hardness of water. It is an organophosphonate which shows excellent sequestration of metal ions at stoichiometric concentrations. These properties make it suitable for use in various applications like Peroxide bleaching, Textile auxiliaries, Industrial and Institutional cleaning, Detergent formulations etc.It has excellent hydrolytic and thermal stability meaning it is stable over wide range of pH values and over higher temperatures, making it suitable for high temperature applications. It is also used as a scale inhibitor in oil and gas applications.

Application

Water treatment formulationsDetergent & personal care product additiveIndustrial & institutional cleanersOil field additiveTextile as peroxide bleach Stabilizer & leather auxiliary chemicals

Definition

Diethylenetriamine five methene phosphoric acid are a kind of widely used corrosion inhibiting and descaling agents, outward appearance is brown color or red-brown thick liquid, nontoxic, molecular formula is C9H28O15N3P5, relative molecular weight is 573.2, be soluble in acidic solution, can form polynary ring huge legendary turtle compound with metal ion in the aqueous solution, loosely is scattered in water, destroy the calcium salt crystalline growths such as carbonate, sulfate scale, thereby play scale effect, can suppress the generation of carbonate, sulfate scale.

General Description

Diethylenetriaminepentakis(methylphosphonic acid) (DTPMP) is a multidentate chelating agent. Hydrogen peroxide oxidation of DTPMP is reported. DTPMP, a phosphonate, is commonly used as crystallization inhibitors.

Flammability and Explosibility

Notclassified

Industrial uses

Under alkaline environment and high temperature, anticorrosion-antiscaling property is good.Diethylenetriamine five methene phosphoric acid are used as the anti-incrustation corrosion inhibitor of recirculated cooling water and feedwater in water treatment, be specially adapted to the anti-incrustation corrosion inhibitor of alkaline recirculated cooling water, and can be used for containing the high oil-field flooding of barium carbonate and the anti-incrustation corrosion inhibitor of water coolant, use separately this product in compound drug, without adding dispersion agent, the dirt deposition amount is still very little; This product also can be used as peroxide stabiliser, for textile printing and dyeing in the dispersion agent, oxygen delignification stablizer, chemical fertilizer of sequestrant, pigment trace element carry agent, concrete additive; In addition, at aspects such as papermaking, plating, metal pickling and makeup; Also can make the stablizer of oxidizing bactericide.

Synthesis

The technical grade diethylenetriamine that total amount is 10% will be accounted for, the novel environment friendly formaldehyde that total amount is 58% that accounts for that content is 40% is sent in chemical reaction kettle, starting stirrer stirs, rotating speed is 20 rev/mins, even blend, send into steam immediately in the reactor interlayer, make slowly to heat up in reactor, control temperature between 50 ℃-55 ℃, add slowly and account for the technical grade phosphorous acid crystal that total amount is 30%, be stirred to the follow-up temperature of continuing rising of whole dissolvings, add slowly and account for the catalyzer composite type metallic oxide that total amount is 2%, after stirring, be warming up between 95 ℃-98 ℃, stirring reaction 1.6-1.8 hour, stop, to the reactor steam supply, being cooled to normal temperature, continue to stir, add the aqueous sodium hydroxide solution that appropriate content is 20%, adjust pH is to stop stirring after between 10-10.5 obtaining finished product, during use, can be using diethylenetriamine five methene phosphoric acid as anti-incrustation corrosion inhibitor or clean-out system use and get final product.

InChI:InChI=1/C9H28N3O15P5/c13-28(14,15)5-10(1-3-11(6-29(16,17)18)7-30(19,20)21)2-4-12(8-31(22,23)24)9-32(25,26)27/h1-9H2,(H2,13,14,15)(H2,16,17,18)(H2,19,20,21)(H2,22,23,24)(H2,25,26,27)

Synthetic route

formaldehyd (50-00-0) + 1,5-diamino-3-azapentane (111-40-0) → diethylenetriamine penta(methylenephosphonic acid) (15827-60-8)

Conditions	Yield
With hydrogenchloride; phosphonic Acid In water at 115℃; for 2h; Large scale;	98.3%
With phosphorous acid; methanesulfonic acid In water at 105 - 130℃; for 2.05 - 6.33333h; Product distribution / selectivity; Heating / reflux;	0 - 60.0 %Spectr.
Stage #1: 3-azapentane-1,5-diamine With hydrogenchloride; phosphorus(III) oxide; water at 93℃; Inert atmosphere; Stage #2: formaldehyd; hydrogenchloride In water at 105 - 110℃; for 2.25h;
Stage #1: formaldehyd; 3-azapentane-1,5-diamine With hydrogenchloride; phosphorous acid In water at 93 - 97℃; for 0.666667h; Flow reactor; Stage #2: at 80 - 100℃; for 2h; Time; Autoclave;
Stage #1: 3-azapentane-1,5-diamine With hydrogenchloride; phosphonic Acid In water at 5 - 20℃; for 2h; Large scale; Stage #2: formaldehyd In water at 90 - 95℃; for 3h; Large scale;

diethylenetriaminopentaacetic acid (67-43-6) → diethylenetriamine penta(methylenephosphonic acid) (15827-60-8)

Conditions	Yield
With phosphorus(III) oxide; methanesulfonic acid at 55 - 90℃; for 2h;	89.6 %Spectr.

N,N',N',N'',N''-hydroxymethyl-(2-aminoethyl)ethane-1,2-diamine (1542224-36-1) → diethylenetriamine penta(methylenephosphonic acid) (15827-60-8)

Conditions	Yield
Stage #1: N,N',N',N'',N''-hydroxymethyl-(2-aminoethyl)ethane-1,2-diamine With phosphorus(III) oxide; trifluoroacetic acid In acetonitrile at 35 - 60℃; for 0.333333h; Inert atmosphere; Stage #2: With water In acetonitrile at 85℃; for 0.25h; pH=5.4; Inert atmosphere;

gadolinium(III) oxide + diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) → 3Na(1+)*Gd(3+)*(PO3CH2)2NC2H4N(CH2PO3)C2H4N(CH2PO3)2(10-)*4H(1+)=Na3[Gd((HPO3CH2)2NC2H4N(CH2PO3)C2H4N(CH2PO3H)2)]

Conditions	Yield
With sodium hydroxide In water the phosphonic acid was suspd. in water, pH was adjusted to 5.0 by addn. of NaOH, addn. of Gd2O3, heated at 90°C for 2 h, pH was adjusted with NaOH to 7.5; filtered, evapd. under reduced pressure; elem. anal.;	96%

diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) + nickel diacetate (373-02-4, 14998-37-9, 33025-09-1, 94044-50-5, 98268-31-6) → Ni5(diethylene triamine-N,N,N',N',N'',N''-penta(methylenephosphonic acid)(-10H))2*20H2O

Conditions	Yield
With Na2CO3 In water to soln. of ligand and metal salt in H2O added aq. soln. of Na2CO3 dropwise with stirring; ppt. filtered; washed (hot H2O, aq. acetone, acetone); dried on water bath; elem. anal.;	81%
With aq. Na2CO3 In water slow addn. of aq. soln. of ligand to soln. of metal salt with constant stirring, pptn. on addn. of aq. Na2CO3; addn. of acetone, filtration, washing (hot water, aq. acetone, acetone), drying (60-70°C); elem. anal.;

tetrakis(tetrabutylammonium) octamolybdate + diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) + water (7732-18-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2(C4H9)4N(1+)*(NH2CH2PO3)2Mo5O15(2-)*2CH3NHCH3*H2O=((C4H9)4N)2(NH2CH2PO3)2Mo5O15*2CH3NHCH3*H2O

Conditions	Yield
In water; acetonitrile Mo complex dissolved in CH3CN under stirring, treated with H2O, treated dropwise under vigorous stirring with ligand and DMF, stirred at 65°C for 5 h; cooled to room temp., crystd. for 4 weeks, elem. anal.;	25%

diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) → C9H28N3O18P5

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In water at 60℃; pH 9;

diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) + BDH → diethylenetriamine-N,N,N',N",N"-pentaacetic acid pentasodium salt (140-01-2)

chromium(III) nitrate + diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) → 4Cr(3+)*(C9H18N3O15P5)(10-)*2OH(1-)*H2O = Cr4(C9H18N3O15P5)(OH)2*H2O

Conditions	Yield
With aq. Na2CO3 In water slow addn. of aq. soln. of ligand to soln. of metal salt with constant stirring, pptn. on addn. of aq. Na2CO3; addn. of acetone, filtration, washing (hot water, aq. acetone, acetone), drying (60-70°C); elem. anal.;

diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) + iron(II) acetate (1834-30-6, 2140-52-5, 3094-87-9) → 5Fe(2+)*C9H18N3O15P5(10-)*12H2O = Fe5(C9H18N3O15P5)*12H2O

Conditions	Yield
With aq. Na2CO3 In water slow addn. of aq. soln. of ligand to soln. of metal salt with constant stirring, pptn. on addn. of aq. Na2CO3; addn. of acetone, filtration, washing (hot water, aq. acetone, acetone), drying (60-70°C); elem. anal.;

diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) + cadmium(II) acetate (543-90-8) → Cd5(diethylene triamine-N,N,N',N',N'',N''-penta(methylenephosphonic acid)(-10H))2*16H2O

Conditions	Yield
With aq. Na2CO3 In water slow addn. of aq. soln. of ligand to soln. of metal salt with constant stirring, pptn. on addn. of aq. Na2CO3; addn. of acetone, filtration, washing (hot water, aq. acetone, acetone), drying (60-70°C); elem. anal.;

diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) → 5Co(2+)*C9H18N3O15P5(10-)*16H2O = Co5(C9H18N3O15P5)*16H2O

Conditions	Yield
With aq. Na2CO3 In water slow addn. of aq. soln. of ligand to soln. of metal salt with constant stirring, pptn. on addn. of aq. Na2CO3; addn. of acetone, filtration, washing (hot water, aq. acetone, acetone), drying (60-70°C); elem. anal.;

diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) + copper diacetate (142-71-2) → 5Cu(2+)*C9H18N3O15P5(10-)*15H2O = Cu5(C9H18N3O15P5)*15H2O

Conditions	Yield
With aq. Na2CO3 In water slow addn. of aq. soln. of ligand to soln. of metal salt with constant stirring, pptn. on addn. of aq. Na2CO3; addn. of acetone, filtration, washing (hot water, aq. acetone, acetone), drying (60-70°C); elem. anal.;

diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) + thallium(III) nitrate → thallium(III) diethylenetriaminopentakis(methylenephosphate)

Conditions	Yield
In water mixed at pH 2; NMR;

zirconyl chloride octahydrate + diethylenetriamine penta(methylenephosphonic acid) (15827-60-8) → zirconium diethylene triamine pentamethylene phosphonate

Conditions	Yield
In water aq. amine-compd. added dropwise at room temp. to Zr-compd. in H2O with continuous stirring, stirred for 1 h, allowed to age for 15 h; filtered, washed with H2O, dried at room temp., elem. anal.;

Upstream product

• 67-43-6 diethylenetriaminopentaacetic acid 
• 1542224-36-1 N,N',N',N'',N''-hydroxymethyl-(2-aminoethyl)ethane-1,2-diamine 
• 50-00-0 formaldehyd 
• 111-40-0 3-azapentane-1,5-diamine 

Downstream Products

• 140-01-2 diethylenetriamine-N,N,N',N,N-pentaacetic acid pentasodium salt 

Relevant articles and documents

Production process of diethylenetriaminepenta(methylene-phosphonic acid)

The invention discloses a production process of diethylenetriaminepenta(methylene-phosphonic acid). The production process comprises the following specific operation steps: (1) adding metered hydrochloric acid, diethylenetriamine and phosphorous acid into a reactor in order, performing continuous stirring in the reactor, and maintaining the temperature at =50 DEG C; (2) performing heating to a certain temperature, adding a part of a formaldehyde aqueous solution dropwise at different flow rates, after the addition is completed, performing heat preservation, and performing concentration; and (3) adding hydrochloric acid, performing heating to 110-120 DEG C, adding the remaining formaldehyde aqueous solution dropwise, after the addition is completed, performing heat preservation for a reaction, performing evaporation, performing dilution, performing cooling, and adjusting the pH to obtain the qualified finished product. The method accelerates the reaction rate, not only effectively inhibits the production of by-product hydroxymethylphosphonic acid, improves the conversion rate and product yield of the effective active component diethylenetriaminepenta(methylene-phosphonic acid), butalso shortens the total reaction time, and reduces the production costs; and the method is simple, safe, and easy to operate, and is beneficial to industrial production.

A second ethylene triamine penta methylene phosphonic acid continuous production process

The invention relates to a continuous production process for HTPMP. The process comprises the following steps: adding a certain mole ratio of diethylenetriamine, phosphorous acid, formaldehyde and hydrochloric acid into a mixing kettle, and uniformly mixing under 35 DEG C; pumping into a tubular reactor; after reaction, entering a thermal insulation kettle for thermal insulation and full reaction; after detecting that the phosphorus content is qualified, reducing pressure and externally evaporating formaldehyde; finally, dropwise adding hydrochloric acid for lowering the temperature and diluting to the needed active matter content. The production process adopts continuous feeding and continuous discharging, overcomes the defects of low rate of production, large energy consumption and the like of the current intermittent single-kettle mixing production process, and increases the rate of equipment utilization. The production cycle is shortened, the capacity is increased, the comprehensive energy consumption is reduced, and the large industrial scale production is easily realized.

METHOD FOR THE SYNTHESIS OF AMINOALKYLENEPHOSPHONIC ACID

The present invention is related to a method for the synthesis of an aminoalkylenephosphonic acid or its phosphonate esters comprising the following steps: a) forming, in the presence of an aldehyde or ketone and an acid catalyst, a reaction mixture by mixing a compound comprising at least one HNR1R2 moiety or a salt thereof, with a compound having one or more P-O-P anhydride moieties, said moieties comprising one P atom at the oxidation state (+III) and one P atom at the oxidation state (+III) or (+V), wherein the ratio of moles of aldehyde or ketone to N-H moieties is 1 or more and wherein the ratio of N-H moieties to P-O-P anhydride moieties is 0.3 or more and, b) recovering the resulting aminoalkylenephosphonic acid comprising compound or its phosphonate esters.