2664-61-1

Basic information

• Product Name: 3,3',3''-NITRILOTRIS(PROPIONAMIDE)
• Synonyms: 3,3’,3’’-nitrilotris-propanamid;3,3',3''-NITRILOTRIS(PROPIONAMIDE);Nitrilotrispropionamide;3,3'',3''-NITRILOTRIS(PROPIONAMIDE) 98+%;3,3',3''-Nitrilotris(propanamide);3,3',3''-Nitrilotripropanamide
• CAS NO: 2664-61-1
• Molecular Formula: C₉H₁₈N₄O₃
• Molecular Weight: 230.26
• EINECS: 220-196-3
• Mol File: 2664-61-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 183 °C
• Boiling Point: 634.3°Cat760mmHg
• Flash Point: 337.4°C
• Appearance: /
• Density: 1.233g/cm³
• Vapor Pressure: 5.41E-16mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: 3,3',3''-NITRILOTRIS(PROPIONAMIDE)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3',3''-NITRILOTRIS(PROPIONAMIDE)(2664-61-1)
• EPA Substance Registry System: 3,3',3''-NITRILOTRIS(PROPIONAMIDE)(2664-61-1)

Safety Data

• Hazardous Substances Data: 2664-61-1(Hazardous Substances Data)

Usage

General Description

3,3',3''-NITRILOTRIS(PROPIONAMIDE) is a chemical compound with the molecular formula C9H18N4O3. It is also known as tris(propionamide) or TPA. 3,3',3''-NITRILOTRIS(PROPIONAMIDE) is primarily used as a viscosity-reducing agent and thickening stabilizer in the industrial production of aqueous solutions, especially in the oil and gas industry. It is a colorless, odorless solid that is highly soluble in water. TPA is also used as a chelating agent to bind metal ions in various industrial processes, including water treatment and metal extraction. Additionally, it has applications in the cosmetic and personal care industries as an emollient and humectant.

InChI:InChI=1/C9H18N4O3/c10-7(14)1-4-13(5-2-8(11)15)6-3-9(12)16/h1-6H2,(H2,10,14)(H2,11,15)(H2,12,16)

Synthetic route

2-propenamide (79-06-1) → 3,3',3''-nitrilotripropanamide (2664-61-1)

Conditions	Yield
With ammonium hydroxide at 20℃; for 24h;	57%
With ammonia; water
With ammonia

acrylic acid methyl ester (292638-85-8) → 3,3',3''-nitrilotripropanamide (2664-61-1) + 3,3'-imino-di-propionic acid diamide (44994-32-3)

Conditions	Yield
With ammonia at 20℃; mehrmonatige Einwirkung;
With methanol; ammonia at 20℃; mehrmonatige Einwirkung;

acrylic acid methyl ester (292638-85-8) → 3,3',3''-nitrilotripropanamide (2664-61-1)

Conditions	Yield
With ammonia In methanol at 37℃; for 48h;

3,3',3''-nitrilotripropanamide (2664-61-1) → Tris(3-aminopropyl)amine (4963-47-7)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 18h;	35%

3,3',3''-nitrilotripropanamide (2664-61-1) → acrylonitrile (107-13-1)

Conditions	Yield
With manganese oxide
With silica gel

3,3',3''-nitrilotripropanamide (2664-61-1) → bis(3-aminopropyl)amine (56-18-8) + Tris(3-aminopropyl)amine (4963-47-7)

Conditions	Yield
With lithium aluminium tetrahydride

3,3',3''-nitrilotripropanamide (2664-61-1) → 3,3',3''-nitrilotripropanoic acid (817-11-8)

Conditions	Yield
With sodium hydroxide Heating;

3,3',3''-nitrilotripropanamide (2664-61-1) → tris[[(3-hydroxypicolinyl)carbonyl]-2-aminopropyl]amine

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / LiAlH4 / tetrahydrofuran / 18 h / 20 °C 2: tetrahydrofuran / 19 h / Heating View Scheme

3,3',3''-nitrilotripropanamide (2664-61-1) → 3-[Bis-(2-hydroxycarbamoyl-ethyl)-amino]-N-hydroxy-propionamide (69778-14-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2N NaOH / Heating 2: 90 percent / 1-ethyl-3-(dimethylaminopropyl)carbodiimide / tetrahydrofuran; H2O / Ambient temperature; pH ca. 4.8 3: 84 percent / H2 / 10percent Pd-C / methanol / 12 h / 760 Torr / Ambient temperature View Scheme

3,3',3''-nitrilotripropanamide (2664-61-1) → N-Benzyloxy-3-[bis-(2-benzyloxycarbamoyl-ethyl)-amino]-propionamide (141621-29-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2N NaOH / Heating 2: 90 percent / 1-ethyl-3-(dimethylaminopropyl)carbodiimide / tetrahydrofuran; H2O / Ambient temperature; pH ca. 4.8 View Scheme

3,3',3''-nitrilotripropanamide (2664-61-1) → N,N',N''-triformamid (131457-36-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 View Scheme

3,3',3''-nitrilotripropanamide (2664-61-1) → 3,3',3''-Nitrilotripropylisocyanid (2456-97-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 3: Cl-C(O)-CCl3 View Scheme

Upstream product

• 79-06-1 2-propenamide 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 56-18-8 bis(3-aminopropyl)amine 
• 4963-47-7 Tris(3-aminopropyl)amine 
• 817-11-8 3,3',3''-nitrilotripropanoic acid 
• 141621-29-6 N-Benzyloxy-3-[bis-(2-benzyloxycarbamoyl-ethyl)-amino]-propionamide 
• 107-13-1 acrylonitrile 

Relevant articles and documents

Dendrimers: A new class of corrosion inhibitors for mild steel in 1?M HCl: Experimental and quantum chemical studies

The inhibition properties of two ammonia cored dendrimers have been investigated for mild steel corrosion in 1?M hydrochloric acid solution using chemical, electrochemical, surface and quantum chemical calculation methods. It was observed that inhibition efficiency increases with increasing the concentration of both the dendrimers and maximum efficiency was obtained at 50?ppm (50?mgL??1) concentration. Potentiodynamic study suggested that investigated dendrimers behaved as mixed inhibitors and their adsorption on mild steel surface obeyed the Langmuir adsorption isotherm. Scanning electron microscopy (SEM) and energy dispersive X-ray spectroscopy (EDX) examinations of mild steel surface confirmed the inhibition behavior of investigated inhibitor molecules. Atomic force microscopic (AFM) study revealed that studied compounds increases the surface smoothness of AFM micrographs by adsorbing on the metallic surface. Several quantum chemical calculations parameters were calculated and the results obtained were found to be consistent with the experimental findings.

General method for the synthesis of trishydroxamic acids

Triscarboxylic acids, when treated with hydroxylamines in the presence of water-soluble carbodiimide in THF-H2O, at pH≈4.8, yield the corresponding trishydroxamic acids in good yields.