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

Description

Diethylenetriaminepenta(methylene-phosphonic acid), also known as Diethylenetriaminepentakis(methylphosphonic acid) (DTPMP), is a multidentate chelating agent and a phosphonate. It is a brown or red-brown thick liquid, nontoxic, with a molecular formula of C9H28O15N3P5 and a relative molecular weight of 573.2. DTPMP is soluble in acidic solutions and can form polynary ring compounds with metal ions in aqueous solutions. It is commonly used as a crystallization inhibitor and demonstrates excellent inhibition of barium sulfate (BaSO4) precipitation.

Uses

1. Water Treatment Formulations:
Diethylenetriaminepenta(methylene-phosphonic acid) is used as a corrosion and scale inhibitor for recirculated cooling water and feedwater. It is particularly effective in alkaline recirculated cooling water systems and can also be used for controlling barium carbonate in high oil-field flooding and as an anti-incrustation corrosion inhibitor for water coolants.
2. Detergent & Personal Care Product Additive:
Diethylenetriaminepenta(methylene-phosphonic acid) is used as an additive in the detergent and personal care industry, where it helps prevent the formation of scale and corrosion.
3. Industrial & Institutional Cleaners:
In the industrial and institutional cleaning sector, Diethylenetriaminepenta(methylene-phosphonic acid) is used to prevent scaling and corrosion on equipment and surfaces.
4. Oil Field Additive:
Diethylenetriaminepenta(methylene-phosphonic acid) is used as an additive in the oil field to inhibit scaling and corrosion, particularly in high-temperature and alkaline environments.
5. Textile Industry:
In the textile industry, Diethylenetriaminepenta(methylene-phosphonic acid) is used as a peroxide bleach stabilizer and a leather auxiliary chemical, enhancing the performance and quality of textile products.
6. Research Applications:
Diethylenetriaminepentakis(methylphosphonic acid) solution is used in studies investigating the dynamics and kinetics of sodium sulfate crystallization in the presence of various organophosphonic acids. It may also be employed as a ligand for the characterization of Ce3+ complexes by luminescence spectroscopy.
7. Wastewater Treatment:
Diethylenetriaminepenta(methylene-phosphonic acid) is a component of phosphorous-containing nanoparticles and materials, such as in the preparation of chitosan nanoparticles for plutonium pulmonary decorporation, helping to treat wastewater pollutants.
8. Other Applications:
Diethylenetriaminepenta(methylene-phosphonic acid) can also be used as a peroxide stabilizer in textile printing and dyeing, an oxygen delignification stabilizer, a chemical fertilizer sequestrant, a pigment trace element carrier agent, and a concrete additive. Additionally, it is utilized in papermaking, plating, metal pickling, and as a stabilizer of oxidizing bactericide in various industries.

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.

Flammability and Explosibility

Notclassified

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

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

The present invention is related to a new method for the synthesis of alpha-aminoalkylenephosphonic acid or its phosphonate esters comprising the steps of forming a reaction mixture by mixing a P-O-P anhydride moiety comprising compound, having one P-atom at the oxidation state (+111) and the other P-atom at the oxidation state (+111) or (+V), an aminoalkanecarboxylic acid and an acid catalyst, wherein said reaction mixture comprises an equivalent ratio of alpha-aminoalkylene carboxylic acid to P-O-P anhydride moieties of at least 0.2, and recovering the resulting alpha-aminoalkylene phosphonic acid compound or an ester thereof from the reaction mixture.