Methylethyl ketone oxime

Last updated
Methylethyl ketone oxime
MEKOstr'.png
Names
IUPAC name
(2E)-N-Hydroxy-2-butanimine
Other names
MEKO, 2-Butanone oxime
Identifiers
  • 96-29-7 Yes check.svgY
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.270 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-496-6
PubChem CID
UNII
  • InChI=1S/C4H9NO/c1-3-4(2)5-6/h6H,3H2,1-2H3/b5-4+ X mark.svgN
    Key: WHIVNJATOVLWBW-SNAWJCMRSA-N X mark.svgN
  • InChI=1/C4H9NO/c1-3-4(2)5-6/h6H,3H2,1-2H3/b5-4+
    Key: WHIVNJATOVLWBW-SNAWJCMRBX
  • CC/C(=N/O)/C
Properties
C4H9NO
Appearancecolourless liquid
Density 0.923 g/cm3
Melting point −15 °C (5 °F; 258 K)
Boiling point 152 °C (306 °F; 425 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Methylethyl ketone oxime is the organic compound with the formula C2H5C(NOH)CH3. This colourless liquid is the oxime derivative of methyl ethyl ketone. MEKO, as it is called in the paint industry, is used to suppress "skinning" of paints: the formation of a skin on paint before it is used. It is particularly used in alkyd paints. MEKO functions by binding the drying agents, metal salts that catalyze the oxidative crosslinking of drying oils. Once the paint is applied to a surface, MEKO evaporates, thereby allowing the drying process to proceed. Other antiskinning agents have been used, including phenolic antioxidants (E.G butylated hydroxytoluene), but these tend to yellow the paint. [1] This oxime is also used in some types of RTV silicones.

Related Research Articles

Acrylic paint Water resistant paint type

Acrylic paint is a fast-drying paint made of pigment suspended in acrylic polymer emulsion and plasticizers, silicon oils, defoamers, stabilizers, or metal soaps. Most acrylic paints are water-based, but become water-resistant when dry. Depending on how much the paint is diluted with water, or modified with acrylic gels, mediums, or pastes, the finished acrylic painting can resemble a watercolor, a gouache, or an oil painting, or have its own unique characteristics not attainable with other media.

Ketone Class of organic compounds having structure RCOR´

In chemistry, a ketone is a functional group with the structure R2C=O, where R can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond). The simplest ketone is acetone (R = R' = methyl), with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.

Paint Pigment applied over a surface that dries as a solid film

Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture to objects. Paint can be made or purchased in many colors—and in many different types, such as watercolor or synthetic. Paint is typically stored, sold, and applied as a liquid, but most types dry into a solid. Most paints are either oil-based or water-based and each have distinct characteristics. For one, it is illegal in most municipalities to discard oil-based paint down household drains or sewers. Clean up solvents are also different for water-based paint than they are for oil-based paint. Water-based paints and oil-based paints will cure differently based on the outside ambient temperature of the object being painted Usually the object being painted must be over 10 °C (50 °F), although some manufacturers of external paints/primers claim they can be applied when temperatures are as low as 2 °C (35 °F).

Oxime

An oxime is a chemical compound belonging to the imines, with the general formula RR'C=NOH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.

Hydroxylamine Inorganic compound

Hydroxylamine is an inorganic compound with the formula NH2OH. The pure material is a white, unstable crystalline, hygroscopic compound. However, hydroxylamine is almost always provided and used as an aqueous solution. It is used to prepare oximes, an important functional group. It is also an intermediate in biological nitrification. In biological nitrification, the oxidation of NH3 to hydroxylamine is mediated by the enzyme ammonia monooxygenase (AMO). Hydroxylamine oxidoreductase (HAO) further oxidizes hydroxylamine to nitrite.

Hydrazone

Hydrazones are a class of organic compounds with the structure R
1
R
2
C
=NNH
2
. They are related to ketones and aldehydes by the replacement of the oxygen with the NNH
2
functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.

Imine

An imine is a functional group or chemical compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen (H) or an organic group (R). If this group is not a hydrogen atom, then the compound can sometimes be referred to as a Schiff base. The carbon atom has two additional single bonds. The term "imine" was coined in 1883 by the German chemist Albert Ladenburg.

Drying oil

A drying oil is an oil that hardens to a tough, solid film after a period of exposure to air, at room temperature. The oil hardens through a chemical reaction in which the components crosslink by the action of oxygen. Drying oils are a key component of oil paint and some varnishes. Some commonly used drying oils include linseed oil, tung oil, poppy seed oil, perilla oil, and walnut oil. Their use has declined over the past several decades, as they have been replaced by alkyd resins and other binders.

Poppyseed oil is an edible oil from poppy seeds.

Limonene Chemical compound

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The D-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common L-isomer is found in mint oils and has a piny, turpentine-like odor. The compound is one of the main volatile monoterpenes found in the resin of conifers, particularly in the Pinaceae, and of orange oil.

Phosgene oxime, or CX, is an organic compound with the formula Cl2CNOH. It is a potent chemical weapon, specifically a nettle agent. The compound itself is a colorless solid, but impure samples are often yellowish liquids. It has a strong, disagreeable odor and a violently irritating vapor.

1,4-Benzoquinone Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

Semicarbazide Chemical compound

Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.

An oil drying agent, also known as siccative, is a coordination compound that accelerates (catalyzes) the hardening of drying oils, often as they are used in oil-based paints. This so-called "drying" occurs through free-radical chemical crosslinking of the oils. The catalysts promote this free-radical autoxidation of the oils with air.

Hydroxylammonium sulfate Chemical compound

Hydroxylammonium sulfate (NH3OH)2SO4, is the sulfuric acid salt of hydroxylamine. It is primarily used as an easily handled form of hydroxylamine, which is explosive when pure.

Biomimetic antifouling coatings are special coatings that prevent the accumulation of marine organisms on a surface. Typical antifouling coatings are not biomimetic but are based on synthetic chemical compounds that can have deleterious effects on the environment. Prime examples are tributyltin compounds, which are components in paints to prevent biofouling of ship hulls. Although highly effective at combatting the accumulation of barnacles and other problematic organisms, organotin-containing paints are damaging to many organisms and have been shown to interrupt marine food chains.

Acetaldoxime Chemical compound

Acetaldoxime is the chemical compound with formula C2H5NO. It is one of the simplest oxime-containing compounds, and has a wide variety of uses in chemical synthesis.

Hydroxylamine-<i>O</i>-sulfonic acid Chemical compound

Hydroxylamine-O-sulfonic acid ("HOSA") is the inorganic compound with molecular formula H3NO4S that is formed by the sulfonation of hydroxylamine with oleum. It is a white, water-soluble and hygroscopic, solid, commonly represented by the condensed structural formula H2NOSO3H, though it actually exists as a zwitterion and thus is more accurately represented as +H3NOSO3. It is used as a reagent for the introduction of amine groups (–NH2), for the conversion of aldehydes into nitriles and alicyclic ketones into lactams (cyclic amides), and for the synthesis of variety of nitrogen-containing heterocycles.

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

N-Hydroxyphthalimide is the N-hydroxy derivative of phthalimide. The compound is used, inter alia, as catalyst for oxidation reactions, in particular for the selective oxidation with molecular oxygen under mild conditions.

2,3,4-Pentanetrione Chemical compound

2,3,4-Pentanetrione (or IUPAC name pentane-2,3,4-trione, triketopentane or dimethyl triketone) is the simplest linear triketone, a ketone with three C=O groups. It is an organic molecule with formula CH3COCOCOCH3.

References

  1. J. Bielman "Antiskinning Agents" in "Additives for Coatings" J. H. Bielman, Ed. Wiley-VCH, 2000, Weinheim. ISBN   3-527-29785-5.