rev 29/12/24

TDA1

Tris(dioxa-3,6-heptyl)amine

Molecular Formula  : C15H33NO6

Synonyms

• Tris(2-(2-methoxyethoxy)ethyl)amine
• 70384-51-9
• Tris(dioxa-3,6-heptyl)amine
• Tris[2-(2-methoxyethoxy)ethyl]amine
• Tris(3,6-dioxaheptyl)amine

Molecular Weight    323.43 g/mol

Densité 1.011
Boiling point  163°C to 171°C ( Pressure 1 mmHg)
Flash point  162°C (323°F)
Refractive index  1.4486

 Depositor-Supplied Synonyms

• Tris(2-(2-methoxyethoxy)ethyl)amine
• 70384-51-9
• Tris(dioxa-3,6-heptyl)amine
• Tris[2-(2-methoxyethoxy)ethyl]amine
• Tris(3,6-dioxaheptyl)amine
• TDA-1
• 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]ethanamine
• Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-
• Ethanamine, 2-(2-methoxyethoxy)-N,N-bis(2-(2-methoxyethoxy)ethyl)-
• tris-(2-(2-methoxyethoxy)ethyl)amine

Chemical synthesis

Almost all TDA-1 synthesis start from Diethylene glycol monomethyl ether  (in short MDG for methyl diglycol )

Diethylene glycol monomethyl ether contains an alcohol ether structure, is an excellent high-boiling point solvent, can dissolve organic molecules, synthetic polymers and natural macromolecules, and has certain water solubility, so that the diethylene glycol monomethyl ether is widely used as a solvent for dyes, synthetic resins, nitrocellulose, cellulose acetate, oils and the like, and is also used as a high-boiling point solvent in printing ink, paint and the like, and is also used as a cleaning agent, a plasticizer, an extracting agent and the like. It is available at very competitive price from various manufacturers all around the world

At present methyl diglycol is made starting from ethylen oxide/water and methanol  (Ethylen oxide comes from oxydation of ethylen with oxygen or air on a silver catalyst) ,  .If needed it can be produced by reaction of diethylene glycol with methanol using acid catalyst (2018 China patent CN111233641 )



Reaction to produce TDA-1 consist of   ammonia reaction on MDG at elevated temperature with a catalyst (generally Nickel catalyst doped with various additives) .The reaction  gives a mixture of mono, di and tri amine .By optimisation a the catalyst and the type of chemical reactor used it is possible  to have TDA-1 being the main product .Reaction is made using MDG as solvent .The purification is made by vaccum distillation

Another route consist of starting from chloro derivative of MDG which can be obtained following various way anf make it to react with ammonia .

See below the various way to get TDA-1 with reference of patents giving details on the working conditions







More detailed info on TDA-1 synthesis  HERE

Examples of TDA-1 use

Tris(dioxa-3,6-heptyl)amine is a specialized chemical compound, notable for its unique structure and applications in chemical synthesis and materials science.

Tris(3,6-dioxaheptyl)amine acts as a phase transfer catalyst used in the preparation of various product like 1,3-dideaza-2'-deoxyadenosine and related benzimidazole 2'-deoxyribonucleosides.

 It is also used as an intermediate in the synthesis of telithromycin. Further, it is used in the oxidation of arylmethanols under phase-transfer conditions.

In addition to this, it acts as a cryptand during phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine.More examples of uses below .

• Process for the disproportionation of silanes

  Publication Number: US-4548917-A  Priority Date: 1983-02-25  

  
  
• Process for the preparation of fluorobenzonitriles

  Publication Number: EP-0049186-B1  Priority Date: 1980-09-25  

  
  
• Preparation of benzenoid ethers and thioethers

  Publication Number: US-4287125-A  Priority Date: 1979-06-27  

  
  
• Preparation of hydrogenosilanes

  Publication Number: US-4629801-A    Priority Date: 1985-02-04  
• Isomerization of bromohalogenobenzenes

  Publication Number: US-4479022-A  Priority Date: 1981-04-08  

  
  
• Preparation of hydrogenated silanes by redistribution of hydrosilanes

  Publication Number: US-4567286-A  Priority Date: 1983-09-28  

   
• Process for preparing trifluoroethoxybenzene or trifluoroethylthiobenzene

  Publication Number: US-4816596-A  Priority Date: 1985-03-29  

  
  
• Preparation of aliphatic/aromatic ethers

  Publication Number: US-4314086-A  Priority Date: 1979-06-20  

  
  
• Process for solubilizing organic or mineral salts in organic solvents

  Publication Number: US-4343745-A  Priority Date: 1979-03-02  

  Abstract: The invention provides a process for solubilizing an organic or mineral salt in an organic solvent, said process comprising contacting an organic or mineral salt 

  
  
• Isomerization of bromohalogenobenzenes

  Publication Number: US-4479022-A  Priority Date: 1981-04-08  

• Preparation of silane from methyldichlorosilane and chlorosilanes
• Publication Number: US-4605543-A  Priority Date: 1983-09-28  
• Process for the preparation of tris-(polyoxaalkyl)-amines
• Publication Number: EP-0005094-B1  Priority Date: 1978-04-21  
• New organomagnesium complexes in solid form, process for their preparation, and their use
• Publication Number: US-4835316-A  Priority Date: 1986-10-03  
• CA3117586A1 2018-10-26 2020-04-30 Championx Usa Inc. Ether amine additives for steam-injection oil recovery
  
  Disclosed herein are improved methods of enhanced oil recovery and additives therefor. One or more additives, may be added to steam in steam-assisted oil recovery methods resulting in vapor compositions that comprise the additive and steam. The one or more additives may also be added to water, and the resulting water-additive mixture vaporized to provide a vapor composition comprising the additive and steam. Formation of the vapor composition is followed by injection of the vapor composition into a subterranean reservoir including heavy oil and/or bitumen. [0012] The vapor compositions may condense during and/or after injection to form aqueous condensates. Vapor compositions derived from water-additive mixtures comprising, consisting essentially of, or consisting of water and 125 ppm to 250 ppm of one or more additives condense to form aqueous condensates having a lower oil/water dynamic interfacial tension than water alone. 
• • Positive photosensitive composition
    EP-2296039-B1; Grant Date: 2013-09-25

  • Preparation containing ZnO cubane mixture, and method of manufacturing ZnO semiconductor layer using said preparation
    JP-5683477-B2; Grant Date: 2015-03-1
• • Process for the preparation of optically active methadones in high enantiomeric purity
    US-6143933-A; Grant Date: 2000-11-07