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Diisobutylamine

From Wikipedia, the free encyclopedia
Diisobutylamine
Names
IUPAC name
N-isobutyl-2-methylpropan-1-amine
Other names
2-Methyl-N-(2-methylpropyl)-1-propanamine
Identifiers
3D model (JSmol)
1209251
ChemSpider
ECHA InfoCard 100.003.473 Edit this at Wikidata
EC Number
  • 203-819-3
RTECS number
  • TX1750000
UNII
UN number UN2361
  • Key: NJBCRXCAPCODGX-UHFFFAOYSA-N
  • InChI=1/C8H19N/c1-7(2)5-9-6-8(3)4/h7-9H,5-6H2,1-4H3
  • CC(C)CNCC(C)C
Properties
C8H19N
Molar mass 129.243 g/mol [1]
Appearance colorless liquid
Density 0.74 g/mL
Melting point −77 °C (−107 °F; 196 K)
Boiling point 139 °C (282 °F; 412 K)
5 g/L (20 °C)
Vapor pressure 0.972 kPa
Thermochemistry
-1.387 kJ/g
14 kJ/g
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable, corrosive; highly toxic
GHS labelling:[2]
GHS02: FlammableGHS05: CorrosiveGHS06: Toxic
Warning
H226, H301, H302, H314, H412
P210, P273, P280, P303+P361+P353, P304+P340+P310, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Flash point 29.44 °C (84.99 °F; 302.59 K)
290 °C (554 °F; 563 K)
Explosive limits 0.9-6.3%
Lethal dose or concentration (LD, LC):
100 — 145 mg/kg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diisobutylamine is an organic compound with the formula ((CH3)2CHCH2)2NH. Classified as a secondary amine, the molecule contains two isobutyl groups. This colorless liquid is a weak base that is useful as an inhibitor of bacterial growth, as a precursor to various fertilizers, and a corrosion inhibitor.[3]

Applications

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Environmental

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Diisobutylamine has been used in water flooding operations to control the growth of sulfate reducing bacteria. When water was treated with low concentrations of diisobutylamine, the microorganisms usually present were killed. This has wide environmental impacts, because even microorganisms resistant to normal bactericides were removed from the water by the diisobutylamine.[4]

Diisobutylamine is also used as a precursor to various fertilizers, and it is produced when plants or agents in soil break down butylate fertilizers.[5]

Industrial

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It is a precursor to the herbicide called butylate.[3]

It is used as an agent to minimize corrosion in processes involving hydrocarbon streams which contain residual ammonia or amines. Being more basic, diisobutylamine reacts preferentially with any mineral acids in the stream (i.e. HCl). Also because diisobutylamine is more basic, its conjugate acid is less acidic, leading to a less corrosive salt formed.[6]

Another use of diisobutylamine is in preventing corrosion and cleaning surfaces containing titanium nitride (i.e. semiconductors in computer chips, solar panels, bioMEMS, etc.). When mixed with an oxidizing agent, water, and a borate species, the mixture can clean particles, residues, metal ion contaminants, and organic contaminants all without damaging the low-k dielectrics.[7]

Diisobutylamine has also been used to help improve storage conditions of fuel oils. Commercial fuel oils are often subject to discoloration or formation of insoluble sludge during storage which causes a loss of value. However, when stored with amine salts containing diisobutylamine, the change in color or formation of sludge of the oil is significantly reduced.[8]

Plastic polymers treated with basic species including diisobutylamine show rapid decrosslinking of the polymer network. This suggests that reworkable polymer materials could be formed that could easily be degraded and recycled.[9]

Reactions

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Diisobutylamine reacts with arylphosphonic dichlorides to give arylphosphonic amines.[10]

Diisobutylamine reacts with dimethyldioxirane to give diisobutylhydroxylamine, as typical for oxidation of secondary amines to give hydroxylamines.[11]

References

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  1. ^ Haynes, W. M. (2012). CRC Handbook of Chemistry and Physics (93 ed.).
  2. ^ "135186 Diisobutylamine". Sigma-Aldrich. Retrieved 24 December 2021.
  3. ^ a b Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_001. ISBN 9783527303854.
  4. ^ US patent 3054748A, Edward O. Bennett & Edward B. Hodge, "Process for the Control of Bacteria in Water Flooding Operations in Secondary Oil Recovery", published 1962-09-18 
  5. ^ Montgomery, John Harold. Agrochemicals Desk Reference: Environmental Data. p. 64.
  6. ^ Lack, Joel E. "Strong Base Amines to Minimize Corrosion in Systems Prone to Form Corrosive Salts". US Patent 2012149615.
  7. ^ Cooper, Emanuel; George Totir; Makonnen Payne. "Composition for and Method of Suppressing Titanium Nitride Corrosion". European Patent WO2012051380.
  8. ^ Geller, Henry C.; Bernard Miller Sturgis (1956). Cracked Fuel Oil Stabilized With Amine Salts of Dithiocarbamic Acids.
  9. ^ Malik, Jitendra; Stephen J. Clarson (December 31, 2001). "A Thermally Reworkable UV Curable Acrylic Adhesive Prototype". International Journal of Adhesion and Adhesives. 22 (4): 283–289. doi:10.1016/S0143-7496(02)00005-2. S2CID 98179814.
  10. ^ Freedman, Leon D.; G. O. Doak. The Preparation of Amides of Arylphosphonic Acids III. Amides of Secondary Amines.
  11. ^ Murray, Robert W.; Megh Singh (2006). A High Yield One-Step Synthesis of Hydroxylamines. pp. 3509–3522.