Diisobutylamine

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Diisobutylamine
Diisobutylamine line structure.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-819-3
PubChem CID
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]
Appearancecolorless 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]
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg
Warning
H226, H301, H302, H314, H412
P210, P273, P280, P303+P361+P353, P304+P340+P310, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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]

Contents

Applications

Environmental

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

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

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]

Related Research Articles

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

A lubricant is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, transporting foreign particles, or heating or cooling the surfaces. The property of reducing friction is known as lubricity.

<span class="mw-page-title-main">Chemical industry</span> Industry (branch), which is engaged in the manufacturing of chemical products

The chemical industry comprises the companies and other organizations that develop and produce industrial, specialty and other chemicals. Central to the modern world economy, it converts raw materials into commodity chemicals for industrial and consumer products. It includes industries for petrochemicals such as polymers for plastics and synthetic fibers; inorganic chemicals such as acids and alkalis; agricultural chemicals such as fertilizers, pesticides and herbicides; and other categories such as industrial gases, speciality chemicals and pharmaceuticals.

<span class="mw-page-title-main">Corrosion</span> Gradual destruction of materials by chemical reaction with its environment

Corrosion is a natural process that converts a refined metal into a more chemically stable oxide. It is the gradual deterioration of materials by chemical or electrochemical reaction with their environment. Corrosion engineering is the field dedicated to controlling and preventing corrosion.

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Hydroxylamine</span> Inorganic compound

Hydroxylamine is an inorganic compound with the formula NH2OH. The material is a white crystalline, hygroscopic compound. Hydroxylamine is almost always provided and used as an aqueous solution. It is consumed almost exclusively to produce Nylon-6. The oxidation of NH3 to hydroxylamine is a step in biological nitrification.

<span class="mw-page-title-main">Flux (metallurgy)</span> Chemical used in metallurgy for cleaning or purifying molten metal

In metallurgy, a flux is a chemical cleaning agent, flowing agent, or purifying agent. Fluxes may have more than one function at a time. They are used in both extractive metallurgy and metal joining.

<span class="mw-page-title-main">Titanium tetrachloride</span> Inorganic chemical compound

Titanium tetrachloride is the inorganic compound with the formula TiCl4. It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. TiCl4 is a volatile liquid. Upon contact with humid air, it forms thick clouds of titanium dioxide and hydrochloric acid, a reaction that was formerly exploited for use in smoke machines. It is sometimes referred to as “tickle” or “tickle 4”, as a phonetic representation of the symbols of its molecular formula.

<i>N</i>-Methylethanolamine Chemical compound

N-Methylethanolamine is an alkanolamine with the formula CH3NHCH2CH2OH. It is flammable, corrosive, colorless, viscous liquid. It is an intermediate in the biosynthesis of choline.

In chemistry, a corrosion inhibitor or anti-corrosive is a chemical compound that, when added to a liquid or gas, decreases the corrosion rate of a material, typically a metal or an alloy, that comes into contact with the fluid. The effectiveness of a corrosion inhibitor depends on fluid composition, quantity of water, and flow regime. Corrosion inhibitors are common in industry, and also found in over-the-counter products, typically in spray form in combination with a lubricant and sometimes a penetrating oil. They may be added to water to prevent leaching of lead or copper from pipes.

<span class="mw-page-title-main">Extreme pressure additive</span>

Extreme pressure additives, or EP additives, are additives for lubricants with a role to decrease wear of the parts of the gears exposed to very high pressures. They are also added to cutting fluids for machining of metals.

Microbial corrosion, also called microbiologically influenced corrosion (MIC), microbially induced corrosion (MIC), or biocorrosion, is when microbes affect the electrochemical environment of the surface they are on. This usually involves building a biofilm, which can lead to either an increase in corrosion of the surface or, in a process called microbial corrosion inhibition, protect the surface from corrosion. Microbial corrosion is worth discussing because it causes trillions of dollars in damage around the globe annually and because every surface that is in some way exposed to the environment is also exposed to microbially induced corrosion. Microbes can corrode in two ways. They can produce byproducts from their cellular processes that corrode metals, or they can keep normal corrosion inhibitors from functioning, leaving surfaces open to attack from other environmental factors.

<span class="mw-page-title-main">Naphthenic acid</span> Chemical compound

Naphthenic acids (NAs) are mixtures of several cyclopentyl and cyclohexyl carboxylic acids with molecular weights of 120 to well over 700 atomic mass units. The main fractions are carboxylic acids with a carbon backbone of 9 to 20 carbons. McKee et al. claim that "naphthenic acids (NAs) are primarily cycloaliphatic carboxylic acids with 10 to 16 carbons", although acids containing up to 50 carbons have been identified in heavy petroleum. The term naphthenic acid has roots in the somewhat archaic term "naphthene" used to classify hydrocarbons. It was originally used to describe the complex mixture of petroleum-based acids when the analytical methods available in the early 1900s could identify only a few naphthene-type components with accuracy. Today "naphthenic" acid is used in a more generic sense to refer to all of the carboxylic acids present in petroleum, whether cyclic, acyclic, or aromatic compounds, and carboxylic acids containing heteroatoms such as N and S. Although commercial naphthenic acids often contain a majority of cycloaliphatic acids, multiple studies have shown they also contain straight chain and branched aliphatic acids and aromatic acids; some naphthenic acids contain >50% combined aliphatic and aromatic acids.

Oil additives are chemical compounds that improve the lubricant performance of base oil. The manufacturer of many different oils can utilize the same base stock for each formulation and can choose different additives for each specific application. Additives comprise up to 5% by weight of some oils.

<span class="mw-page-title-main">Cleaning agent</span> Substance used to remove dirt or other contaminants

Cleaning agents or hard-surface cleaners are substances used to remove dirt, including dust, stains, foul odors, and clutter on surfaces. Purposes of cleaning agents include health, beauty, removing offensive odor, and avoiding the spread of dirt and contaminants to oneself and others. Some cleaning agents can kill bacteria and clean at the same time. Others, called degreasers, contain organic solvents to help dissolve oils and fats.

<span class="mw-page-title-main">2-Acrylamido-2-methylpropane sulfonic acid</span> Chemical compound

2-Acrylamido-2-methylpropane sulfonic acid (AMPS) was a Trademark name by The Lubrizol Corporation. It is a reactive, hydrophilic, sulfonic acid acrylic monomer used to alter the chemical properties of wide variety of anionic polymers. In the 1970s, the earliest patents using this monomer were filed for acrylic fiber manufacturing. Today, there are over several thousands patents and publications involving use of AMPS in many areas including water treatment, oil field, construction chemicals, hydrogels for medical applications, personal care products, emulsion coatings, adhesives, and rheology modifiers.

<span class="mw-page-title-main">Alkylation unit</span>

An alkylation unit (alky) is one of the conversion processes used in petroleum refineries. It is used to convert isobutane and low-molecular-weight alkenes (primarily a mixture of propene and butene) into alkylate, a high octane gasoline component. The process occurs in the presence of an acid such as sulfuric acid (H2SO4) or hydrofluoric acid (HF) as catalyst. Depending on the acid used, the unit is called a sulfuric acid alkylation unit (SAAU) or hydrofluoric acid alkylation unit (HFAU). In short, the alky produces a high-quality gasoline blending stock by combining two shorter hydrocarbon molecules into one longer chain gasoline-range molecule by mixing isobutane with a light olefin such as propylene or butylene from the refinery's fluid catalytic cracking unit (FCCU) in the presence of an acid catalyst.

1-Vinylimidazole is a water-soluble basic monomer that forms quaternizable homopolymers by free-radical polymerization with a variety of vinyl and acrylic monomers. The products are functional copolymers, which are used as oil field chemicals and as cosmetic auxiliaries. 1-Vinylimidazole acts as a reactive diluent in UV lacquers, inks, and adhesives.

Corrosion inhibitors for the petroleum industry are substances used in the oil industry to protect equipment and pipelines against corrosion. Corrosion is a daily problem in the oil industry due to the presence in crude oil of water contaminated with salts, gases and other corrosive contaminants in the production process. Corrosion inhibitors can be classified according to their chemical composition as either organic inhibitors or inorganic inhibitors. They can also be classified by the way they act as anodic or cathodic inhibitors. Cathodic inhibitors act as catalysts to slow down corrosion, while anodic inhibitors protect metal surfaces by acting as physical barriers.

Corrosion inhibitors are substances used in the oil industry to protect equipment and pipes against corrosion. Corrosion is a common problem in the oil industry due to the presence of water, gases, and other corrosive contaminants in the production environment.

References

  1. Haynes, W. M. (2012). CRC Handbook of Chemistry and Physics (93 ed.).
  2. "135186 Diisobutylamine". Sigma-Aldrich. Retrieved 24 December 2021.
  3. 1 2 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. USpatent 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.