1-octaamine - 1-octanamina

1-octaamine
Octyl Amine Structural Formula V.1.svg
1-octanamine-3D.gif
IUPAC name
Octan-1-amina
General
Other names n-octilamina
1-aminooctano
Caprilamina
Semi-developed formula CH 3 - (CH 2 ) 7 - NH 2
Molecular formula C 8 H 19 N
Identifiers
CAS number 111-86-4[1]
RTECS number RG8050000
ChEBI 7728
ChEMBL CHEMBL1160509
ChemSpider 7851
PubChem 8143
SOME SF0V8U4T67
KEGG C01740
Physical properties
Appearance Yellow liquid
Odor Ammoniacal
Density 782 kg/; 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
Chemical properties
Solubility in water 0,2 g/L
log P 3,06
Family Amina
Dangerousness
Flash point 335,15 K (62 °C)
NFPA 704

NFPA 704.svg

2
3
0
Related compounds
amines 1-hexanamina
1-heptanamina
1-nonanamina
Dodecilamina
Azocano
diaminas 1,8-octanediamine
polyamines Tetraethylenepentamine
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 1-octanamina , also known as n-octylamine or simply octylamine , is a primary amine of molecular formula C 8 H 19 N . In nature, it is found in apples. [ 2 ]

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 ]

Synthesis

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 ]

Applications

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 ]

Precautions

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 ]

See also

The following compounds are isomers of 1-octaamine:

References

  1. CAS number
  2. ^ Hans-Dieter Belitz, Werner Grosch, Peter Schieberle (2001). Springer, ed. Textbook of Food Chemistry . p. 800. ISBN 978-3-540-41096-6 .
  3. Octylamine (ChemSpider)
  4. a b Octylamine (Chemical Book)
  5. Arno Behr. Applied homogeneous catalysis . p. 265.
  6. 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.
  7. 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.
  8. 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.
  9. Octan-1-amine 111-86-4 Precursor and Downstream Products (Molbase)
  10. 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.
  11. Octylamine (Chemical Land)
  12. 1-Octylamine, 99% (Alfa Aesar)
  13. ^ 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 .
  14. 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.
  15. 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.
  16. ^ Jiří MALIŠ, Monika KŘÍSTKOVÁ (2005). "STRUCTURE OF VERMICULITE MODIFIED BY ORGANIC MOLECULES" . Acta Geodyn Geomater. 2 (2): 138 . Retrieved July 22, 2016 .
  17. Amine modified clay sorbents (2010). Venkata Subba Rao Kambala, Ravendra Naidu. Patente US 9284201 B2.
  18. 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.
  19. 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.