1-octaamine - 1-octanamina
|Other names|| n-octilamina |
|Semi-developed formula||CH 3 - (CH 2 ) 7 - NH 2|
|Molecular formula||C 8 H 19 N|
|Density||782 kg/m³; 0,782 g/cm³|
|Molar mass||129.24 g / mol|
|Melting point||−1 °C (272 K)|
|Boiling point||176 °C (449 K)|
|Critical temperature||368 °C (641 K)|
|Vapor pressure||1 mmHg (20 °C)|
|Refractive index (n D )||1,429|
|Solubility in water||0,2 g/L|
|Flash point||335,15 K (62 °C)|
|NFPA 704|| |
|amines|| 1-hexanamina |
|Values in the SI and under standard conditions|
(25 ℃ and 1 atm ), unless otherwise indicated.
Physical and chemical properties
At room temperature, 1-octaamine is a yellow liquid with an odor similar to ammonia . Solidifies at -1 ° C and boils at 176 ° C. Practically insoluble in water - just 0.2 g / L - its solubility is much higher in hydrophobic solvents ( log P = 3.06). Like other alkylamines, it is less dense than water ( ρ = 0.782 g / cm³ ), so it floats in it. It is a flammable compound that reaches its flash point at 62 ° C. [ 3 ]
Neutralizes acids in exothermic reactions forming salts and water. May be incompatible with isocyanates , halogenated organic compounds, peroxides , phenols (acids), epoxides , anhydrides, and acid halides . Hydrogen gas can be generated when combined with strong reducing agents such as hydrides . [ 4 ]
1-octaamine can be obtained by hydrogenation of octanedienylamine , a compound that is obtained by telomerization of 1,3-butadiene with ammonia . [ 5 ] Another form of synthesis of 1-octaamine is by reduction of imino (octylimino) azanium, using borohydride ion exchange resin [(BER) -CuSO 4 ] as reducing agent in methanol ; in addition to 1- octaamine, dioctylamine is obtained as a reaction product. [ 6 ]A third synthesis route consists of the selective N -deacetylation at room temperature of N -octylacetamide , using the Schwartz reagent (zirconocene hydrochloride), obtaining a yield close to 95%. [ 7 ] Lastly, it is also possible to make this amine by anti-Markovnikov hydroamination of 1-octene ; the reaction is based on a hidrozirconización followed by amination with electrophiles of nitrogen . [ 8 ]
In turn, 1-octaamine is a precursor of more complex amines such as n-hexyl-n-octaamine , N -n-octylidene-n-octylamine, N -octyl-hydroxylamine and N -propan-2-yloctan-1 -amine. [ 9 ] Also, from the oxidation aerobic 1-octanamina a catalyst of ruthenium on you are obtained nitrile corresponding ( octanonitrilo ). [ 10 ]
1-Octanamine is used in the synthesis of organic compounds and surfactants , as a corrosion inhibitor , detergent, fabric softener, antistatic agent, disinfectant , insecticide , emulsifier , dispersant, and water treatment agent. [ 11 ] Also as a reagent in the preparation of 2H- indazoles and 1H-indazolones, used as inhibitors of myeloperoxidase (MPO). [ 12 ]
This amine has numerous uses as a solvent or catalyst . For example, in the preparation of size-adjustable silica nanoparticles, water is the reagent while different primary amines - such as 1-octaamine or dodecylamine - act as catalysts. [ 13 ] Similarly, synthesis of nanocrystals of cadmium selenide (CdSe) with the same cubic structure as sphalerite , can be carried out using 1-octanamina as solvent. [ 14 ] On the other hand, 1-octaamine, absorbed on silica gel, is capable of effectively removing heavy metals such as copper (II), cadmium (II), lead (II), nickel (II) and silver (I). [ 15 ]
Intercalation in minerals
1-Octaamine has been used as an organic compound capable of intercalating in the interlaminar space of certain clay minerals - such as smectite and vermiculite -, causing the mineral structure to expand in a direction perpendicular to the clay sheets. The species thus produced have properties that make them of interest in various industrial applications. [ 16 ] In this sense, the use of 1-octanamine has been proposed to modify phyllosilicates such as palygorskite so that they can adsorb hydrophobic contaminants such as AFFF foams, surfactantsand perfluorinated compounds. [ 17 ]
The intercalation capacity of this amine has also been investigated in the case of vanadyl phosphate (α-VOPO 4 .2H 2 O), having concluded that 1-octaamine forms bimolecular layers in the interlaminar space; intercalation produces two phases - which coexist simultaneously - with different orientations of the alkyl chain . [ 18 ] Likewise, the study of the intercalation of 1- octaamine in H- magadiite with different solvents has shown that absorption increases with increasing amine concentration but that it also depends on the specific solvent used. [ 19 ]
1-Octaamine is a toxic compound for humans; inhalation, ingestion, or skin contact can cause injury and even death. Its combustion can give off irritating, corrosive and toxic gases. As a combustible material it may burn, but does not ignite immediately. However, when 1-octaamine is heated, the vapors generated can form explosive mixtures with air. [ 4 ]
The following compounds are isomers of 1-octaamine:
- 2-etil-1-hexanamina (isooctilamina)
- CAS number
- Hans-Dieter Belitz, Werner Grosch, Peter Schieberle (2001). Springer, ed. Textbook of Food Chemistry . p. 800. ISBN 978-3-540-41096-6 .
- Octylamine (ChemSpider)
- Octylamine (Chemical Book)
- Arno Behr. Applied homogeneous catalysis . p. 265.
- Tae Bo Si, Nung Min Yoon (1997). «Reducing Characteristics of Borohydride Exchange Resin–CuSO4 in Methanol». Bulletin of the Chemical Society of Japan 70 (5): 1101-1107. Consultado el 18 de junio de 2016.
- Prakash R. Sultane, Trimbak B. Mete and Ramakrishna G. Bhat (2014). «Chemoselective N-deacetylation under mild conditions». Org Biomol Chem. 12 (2): 261-264. Consultado el 22 de julio de 2016.
- Alexandra E. Strom, John F. Hartwig (2013). «One-Pot Anti-Markovnikov Hydroamination of Unactivated Alkenes by Hydrozirconation and Amination». J Org Chem. 78 (17): 8909-14. Consultado el 22 de julio de 2016.
- Octan-1-amine 111-86-4 Precursor and Downstream Products (Molbase)
- Venkatesan, S., Kumar, A. S., Lee, J.-F., Chan, T.-S. and Zen, J.-M. (2012). «Room Temperature Aerobic Oxidation of Amines by a Nanocrystalline Ruthenium Oxide Pyrochlore Nafion Composite Catalyst». Chem. Eur. J. 18 (20): 6147-6151. Consultado el 22 de febrero de 2017.
- Octylamine (Chemical Land)
- 1-Octylamine, 99% (Alfa Aesar)
- El Hawi N, Nayral C, Delpech F, Coppel Y, Cornejo A, Castel A, Chaudret B. (2009). "Silica nanoparticles grown and stabilized in organic nonalcoholic media" . Langmuir 25 (13): 7540-5 . Retrieved July 22, 2016 .
- Zhang LJ, Shen XC, Liang H. (2010). «A mild phosphine-free synthesis of alkylamine-capped CdSe nanocrystals». J Nanosci Nanotechnol. 10 (8): 4949-84. Consultado el 23 de julio de 2016.
- Bowe CA, Pooré DD, Benson RF, Martin DF. (2003). «Extraction of heavy metals by amines adsorbed onto silica gel». J Environ Sci Health A Tox Hazard Subst Environ Eng. 38 (11): 2653-60. Consultado el 22 de julio de 2016.
- Jiří MALIŠ, Monika KŘÍSTKOVÁ (2005). "STRUCTURE OF VERMICULITE MODIFIED BY ORGANIC MOLECULES" . Acta Geodyn Geomater. 2 (2): 138 . Retrieved July 22, 2016 .
- Amine modified clay sorbents (2010). Venkata Subba Rao Kambala, Ravendra Naidu. Patente US 9284201 B2.
- Zhang LJ, Shen XC, Liang H. (2010). «Solid-state 51V NMR investigation of the intercalation of alkylamines into layered alpha-vanadyl phosphate». Langmuir 26 (12): 10115-21. Consultado el 22 de julio de 2016.
- Oh-Yun Kwon, Soon-Yong Jeong, Jeong-Kwon Suh, Beyong-Hwan Ryu, Jung-Min Lee (1996). «Effects of Organic Solvents in the Intercalation of Octylamine into H-magadiite». Journal of Colloid and Interface Science 177 (2): 677-680. Consultado el 22 de julio de 2016.