107-29-9 Usage
Description
Acetaldoxime, also known as Acetaldehyde oxime, is a colorless liquid or crystalline solid with a pungent odor. It is a reducing agent with low toxicity and serves as an important intermediate in various chemical syntheses. Acetaldoxime is characterized by its two crystalline modifications, one melting at 12°C and the other at 46.5°C, and has a relative molecular mass of 59.07. It is very soluble in water, ethanol, and ether, and is flammable and irritative to the eyes, respiratory system, and skin.
Uses
1. Used in Pesticide Synthesis:
Acetaldoxime is used as a pesticide intermediate for the synthesis of pesticides such as Methomyl and Thiodicarb, which are excellent large-scale pesticides.
2. Used in Organic Synthesis:
It serves as an organic synthesis intermediate, being an important component in the creation of acylamides through the aldehyde oxime one-pot method. With the presence of a catalyst like InCl3, acetaldehyde oxime replaces water and reacts with nitrile water to create acylamide at a high yield.
3. Used in Chemical Synthesis as a Stabilizer and Plasticizer:
When melted, Acetaldoxime acts as an excellent solvent for many inorganic and organic compounds, making it useful in organic synthesis, as a stabilizer, and as a plasticizer.
4. Used as an Alcohol Denaturant:
Acetaldoxime is also utilized as an alcohol denaturant, which is a substance added to ethanol to render it unfit for human consumption.
5. Used in Pharmaceutical Synthesis:
Acetaldoxime is involved in the rearrangement reaction to prepare acetamide using nickel(II) acetate as a catalyst, which is an important step in the synthesis of various pharmaceutical compounds.
6. Used in the Preparation of Heterocyclic Compounds:
It acts as a precursor to prepare heterocyclic compounds such as spiroisoxazoline, which have potential applications in the pharmaceutical and chemical industries.
7. Used in the Preparation of Alkylated (Z)-Oximes:
Acetaldoxime is used to prepare alkylated (Z)-oximes by deprotonation followed by reaction with benzyl bromide, which can be further utilized in various chemical and pharmaceutical applications.
8. Used as an Oxygen Scavenger in Boiler Water:
Acetaldoxime is used as an oxygen scavenger in boiler water, replacing the highly toxic hydrazine in the 1990s due to its lower toxicity and higher deoxidizing effect.
Preparation
With suitable precautions, to a solution of 325 gm (4.68 moles) of hy-droxylamine hydrochloride in 300 ml of water mixed with a solution of 255 gm (2.55 moles) of sodium carbonate in 600 ml of water, cooled in an ice-salt mixture, is added dropwise, with stirring, a solution of 200 gm (4.55 moles) of acetaldehyde in 100 ml of water. After standing overnight, the solution is saturated with sodium chloride and the product is separated by repeated extractions with ether.
The combined ether extracts are dried over calcium chloride, filtered, and distilled to afford 215 gm (80%), b.p. 112-114°C (760 mm Hg).
Because many aldehydes are not very water soluble, this reaction may be carried out either with vigorous stirring or by adding sufficient alcohol to make the reaction mixture homogeneous. When the product has to be purified by distillation, it has been recommended that the flask be im-mersed into an oil bath maintained at a constant temperature above the anticipated boiling point of the product rather than warming the product and oil bath up to the boiling range from room temperature. By this technique heptaldoxime, b.p. 103-107°C (66 mm Hg), m.p. 53-55°C, cy-clohexanone oxime, b.p. 100-105°C (10-12 mm Hg), m.p. 87-88°C; and methyl ethyl ketoxime, b.p. 150-155°C, have been prepared. The treatment of a carbonyl compound with a hydroxylamine salt, with or without a solvent (or water), and with a neutralization step of the hydroxylamine salt using a simple base may be considered as a general preparative procedure.
Preparation
Acetaldehyde oxime is produced through the reaction between hydroxylamine and acetaldehyde aqueous solution. The reaction equation is as follows: CH3CHO+NH2OH?HCl+NaOH→CH3CH=NOH+NaCl+H2O
In current industrial production, high levels of crystalline hydroxylamine sulfate are widely used as raw material, made into a 20%~50% aqueous solution and combined with acetaldehyde to create acetaldehyde oxime. The reaction equation is as follows: CH3CHO+(NH2OH)2?H2SO4→CH3CH=NOH
In the aforementioned addition of acetaldehyde into hydroxylamine sulfate aqueous solution, the reaction occurs for 2 hours in 40~50℃ temperature. After it is cooled, inorganic salts are removed to achieve a clear aqueous solution of approximately 50% acetaldehyde oxime. Through inspection, it is revealed that there are very few impurities in addition to acetaldehyde and water in the solution, and the yield of acetaldehyde oxime is above 90% (as hydroxylamine sulfate). Extraction and refinement of this solution can yield a product of over 90% acetaldehyde oxime.
Storage
Keep in cool, ventilated storerooms, away from fire and heat sources. Storage heat should not exceed 30℃.Store separately from oxidants, acids and edible chemical substances – do not mix together. Employ explosion-proof lighting and ventilation facilities. Do not handle with machinery and tools that easily produce sparks. The storage area should have emergency measures for leaks and adequate storage equipment.
Store in a sealed and dark container.
Toxicity level
Highly toxic
Acute Toxicity
Abdominal injection – small mice LD50: 100Mg/kg
Explosivity characteristics
May explode when mixed with water vapor and air.
Flammability characteristics
Flammable; releases toxic nitrogen oxide gas at high temperatures
Storage and Transport
Ventilated, low-temperature and dry storage; store and ship separately from oxidants.
Extinguishing agents
Dry powder, carbon dioxide, sand, foam
Air & Water Reactions
Highly flammable. Easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Very soluble in water.
Reactivity Profile
Acetaldoxime may explode or decompose violently during distillation if samples have been previously been exposed to the air, which causes formation of peroxides of various types. Reacts as both a weak acid and as a weak base. Gives acetaldehyde and a hydroxylammonium salt if heated with aqueous acid. A nickel-catalyzed aldoxime rearrangement to an amide went out of control when a different solvent was employed [J. Loss Prev., 1993, 6(2), 69].
Health Hazard
May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Safety Profile
Poison via intraperitoneal route. Mutation data reported. A dangerous fire hazard with a flash point at room temperature. When heated to decomposition it emits toxic fumes of NOx. See also ALDEHYDES.
Potential Exposure
Used as a chemical intermediate and as an antioxidant and radical scavenger with applications in many industries, including detergents, pharmaceuticals, plastics, paints and lacquers, rubber, and textiles
Shipping
UN2332 Acetaldehyde oxime, Hazard Class: 3; Labels: 3-Flammable liquid.
Incompatibilities
Vapor may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong acids (such as hydrochloric, sulfuric, and nitric), strong bases. The beta-form is able to form unstable peroxides
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed
Check Digit Verification of cas no
The CAS Registry Mumber 107-29-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 107-29:
(5*1)+(4*0)+(3*7)+(2*2)+(1*9)=39
39 % 10 = 9
So 107-29-9 is a valid CAS Registry Number.
InChI:InChI=1/C2H5NO/c1-2-3-4/h2,4H,1H3/b3-2-
107-29-9Relevant articles and documents
Lewis acidic strength controlled highly selective synthesis of oxime via liquid-phase ammoximation over titanosilicates
Zhuo, Zuoxi,Wu, Lizhi,Wang, Lei,Ding, Yichun,Zhang, Xiaoqian,Liu, Yueming,He, Mingyuan
, p. 55685 - 55688 (2014)
The Lewis acidity of titanosilicates determines the selectivity of the oxime in ammoximation. Higher Lewis acidic strength of Ti active sites could promote free H2O2 to participate in the highly efficient formation of NH2OH by lowering the reaction activation energy for the formation of Ti-OOH species, and thus fundamentally suppress the side reactions of deep oxidation.
Geiseler et al.
, p. 49,51, 52, 54, 56 (1973)
Separation and purification method for acetaldehyde oxime
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Paragraph 0031-0065, (2020/02/19)
The invention discloses a separation and purification method for acetaldehyde oxime, and relates to the technical field of separation and purification of oxime. The method comprises the following steps: 1) performing an oxime exchange reaction on cyclohexanone oxime and acetaldehyde to obtain an acetaldehyde oxime reaction solution, performing neutralization by using a base, and after the neutralization is completed, controlling the pH of the acetaldehyde oxime reaction solution to 7; 2) adding toluene into the acetaldehyde oxime reaction solution, performing distillation under reduced pressure to separate acetaldehyde oxime and cyclohexanone to obtain an acetaldehyde oxime and toluene mixed liquid and the cyclohexanone; 3) adding extractant water into the obtained acetaldehyde oxime and toluene mixed liquid, and separating the toluene and the acetaldehyde oxime by using a continuous extraction process to obtain an acetaldehyde oxime aqueous solution and the toluene, respectively; and4) performing reduced-pressure rectification on the acetaldehyde oxime aqueous solution to obtain the acetaldehyde oxime product. The method provided by the invention has simple operation and high purity and yield of the acetaldehyde oxime, does not generate waste liquid, and is an environment-friendly green process route for production separation and purification of the acetaldehyde oxime.
Method for preparing oxime
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Paragraph 0034; 0035; 0036, (2018/09/08)
The invention discloses a method for preparing oxime. The method is characterized in that catalytic reaction for oxime synthesis is performed by using a titanium silicate molecular sieve of a MSE topological structure as a catalyst and using ketone or aldehyde, ammonia and hydrogen peroxide as a reaction system, wherein in the reaction system, the weight ratio of ketone or aldehyde to the catalystto a solvent is 1:(0.03 to 0.15):(1 to 15); the molar ratio of the ketone or aldehyde to the ammonia is 1:(1 to 4); the catalyst is Ti-MSE or a combination body of Ti-MSE and silicon dioxide or a titanium-containing molecular sieve. Compared with the prior art, the method has the advantages that the selectivity is high; the catalytic activity is high; the aftertreatment is simple and convenient;the conversion rate of reactants of ketone or aldehyde reaches up to 99 percent; the product oxime selectivity reaches up to 99 percent, so that the molecular sieve shows excellent catalytic activityin the specific catalysis field; the application field of the molecular sieve is expanded; a novel and environment-friendly ammoxidation oxime preparation path is provided; certain industrial popularization and application prospects and prominent economic values are realized.
