96-29-7 Usage
Description
2-Butanone oxime, also known as methyl ethyl ketoxime, is a colorless or light yellow oily transparent liquid with a musty odor. It has strong complexation with metal ions, is volatile in the air, and is flammable. It can react with hydrochloric acid and sulfuric acid to form methyl ethyl ketone. It has a melting point of -29.5°C, boiling points of 152-153°C and 59-60°C (2kPa), a relative density of 0.9232 (20/4°C), and a refractive index of 1.4410. It is immiscible with alcohol and ether but can be dissolved in 10 parts of water.
Uses
Used in Paint and Coating Industry:
2-Butanone oxime is used as an anti-skinning agent and silicon curing agent for alkyd resin coatings. It serves as an antioxidant to prevent skin formation, offering better performance than butyraldehyde oxime and cyclohexanone oxime.
Used in Organic Synthesis:
2-Butanone oxime is utilized in the synthesis of ketoimine and 2,4-dipyridyl-1,3,5-triazapentadiene palladium(II) complexes. It is also employed in the synthesis of novel acetaldiimine cobalt complex, [CoI2((CH3CH2)(CH3)C=NO)2C(CH3)2].
Used in Anti-skinning Process for Oil-based Paints:
For a variety of oil-based paint, alkyd paint, and epoxy paint, 2-Butanone oxime is used as an anti-skinning agent during the storage and transportation of esters.
Oxime oxygen scavenger
Oxime compounds (dimethyl ketone oxime, methyl ethyl ketoxime (butanone oxime), acetaldehyde oxime) knows as a novel oxygen scavenger is disclosed in the U.S. and patented by Drew Chemical Company in 1984. It displays low toxicity, efficiency, fast-performance, and a blunt protective effects. In Europe and other developed countries it has been widely applied, and China it is also successfully developed in the nineties, and has been successful in promotion.
1. Oxygen scavenging performance: oxime compound is an organic compound with an oxime group. Oxime compounds are currently used for boiler shutdown protection and oxygen mainly acetaldehyde oxime, dimethyl ketone oxime (acetone oxime) and methyl ethyl ketone oxime. Oxime compounds have a strong reduction, easy to react with oxygen. When put in a wide temperature and pressure ranges, oximes has good oxygen scavenging performance. The optimum temperature range is 138~336 ℃, and pressure range is 0.3~13.7Mpa. According to comparative experiments, under the same conditions, the rate of oxygen and oxygen efficiency oximes is higher than that of hydrazine.
2. corrosion and passivation: oximes can restore high iron and copper oxide into suboxide, which can be a good solution in the steel magnetic oxide film formed on the surface of the metal surface passivation plays well, corrosion inhibition. Wherein dimethylketoximino is the best, using the minimum amount required. According to comparative experiments, oxime compounds having the same passivation, corrosion inhibition hydrazine, can significantly reduce the iron content in solution at high temperature and pressure conditions. The steel has a protective effect, among which the dimethylketoximino is best, which requires the least amount . Meanwhile, oxime compounds have cleaning actions to copper corrosion products deposited in the pipeline, economizer, etc., which is in the initial period of oximes. This is the reason why furnace copper water content is significantly higher.
3. Volatile: the volatile degree of oxime compounds is higher than that of hydrazine, DEHA, morpholine, cyclohexylamine, etc. It is close to the volatility of NH3. When the steam condenses, highly volatile oxygen scavenger will has a certain amount of condensation agent which is dissolved in water, therefore, helpful to protect the condensate system metal material.
4. decomposition: By experiments under the high temperature and pressure conditions, the decomposition products of oxime compound is NH3, N2, H2O, trace of acetic acid, formic acid produces, no adverse effects on water vapor system.
5. low toxicity: based on the data comparison of LD50, the LD50 for hydrazine is 290mg/kg, acetaldehyde oxime is 1900mg/kg, methyl ethyl ketone oxime is 2800mg/kg, dimethylket oximino 5500mg/kg. So the toxicity of hydrazine is very strong, and toxicity of oxime compound is very small. It belongs to low toxicity compounds. Test through the skin and mucous membrane contact with oxygen scavengers showed no significant oximes oxygen scavenger irritation and damage, but hydrazine causes damage of skin irritation, erosion, mucosal hyperemia.
The above information is edited by the lookchem of Tian Ye.
Preparation
With suitable precautions, to 1 liter of the sodium hydroxylamine di-sulfonate solution from Preparation 2-1 (approx. 1.2 moles) is added 72 gm (1 mole) of methyl ethyl ketone. The mixture is warmed to 70°C. Then the reaction flask is wrapped with insulation and allowed to cool slowly for 12 hr.
After neutralization with 48% sodium hydroxide solution, the oxime is extracted from the reaction mixture with benzene. The benzene solution is distilled fractionally. The product distills between 152° and 154°C; yield, 65 gm (75%).
Preparation
2-Butanone oxime is obtained by the reaction of butanone and hydroxylamine hydrochloride. It can also be synthesized by the reaction between butanone and hydroxylamine sulfate.
Air & Water Reactions
Highly flammable. Water soluble.
Reactivity Profile
2-Butanone oxime is sensitive to heat. Has exploded at least twice when heated in the presence of acidic impurities [Chem. Eng. News, 1974, 52(35), 3]. Reacts with oxidizing agents. Mixtures with strong acids may explode. Reacts with sulfuric acid to form an explosive product .
Fire Hazard
2-Butanone oxime is combustible.
Flammability and Explosibility
Notclassified
Safety Profile
Poison by
intraperitoneal route. Moderately toxic by
subcutaneous route. May explode if heated.
Reacts with sulfuric acid to form an
explosive product. When heated to
decomposition it emits toxic fumes of NOX.
TEST ITEMS
SPECIFICATION
GRADE
EXCELLENT GRADE
MEKO CONTENT
99.7%min
WATER CONTENT
0.04%
ACID NUMBER (KOH mg/g)
0.05 max
CHROMA NO. (PLATINUM-COBALT)
2 max
Check Digit Verification of cas no
The CAS Registry Mumber 96-29-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 96-29:
(4*9)+(3*6)+(2*2)+(1*9)=67
67 % 10 = 7
So 96-29-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H9NO/c1-3-4(2)5-6/h6H,3H2,1-2H3/b5-4-
96-29-7Relevant articles and documents
Analogues of the Herbicide, N-Hydroxy- N-isopropyloxamate, Inhibit Mycobacterium tuberculosis Ketol-Acid Reductoisomerase and Their Prodrugs Are Promising Anti-TB Drug Leads
Kandale, Ajit,Patel, Khushboo,Hussein, Waleed M.,Wun, Shun Jie,Zheng, Shan,Tan, Lendl,West, Nicholas P.,Schenk, Gerhard,Guddat, Luke W.,McGeary, Ross P.
, p. 1670 - 1684 (2021/02/27)
New drugs to treat tuberculosis (TB) are urgently needed to combat the increase in resistance observed among the current first-line and second-line treatments. Here, we propose ketol-acid reductoisomerase (KARI) as a target for anti-TB drug discovery. Twenty-two analogues of IpOHA, an inhibitor of plant KARI, were evaluated as antimycobacterial agents. The strongest inhibitor of Mycobacterium tuberculosis (Mt) KARI has a Ki value of 19.7 nM, fivefold more potent than IpOHA (Ki = 97.7 nM). This and four other potent analogues are slow- and tight-binding inhibitors of MtKARI. Three compounds were cocrystallized with Staphylococcus aureus KARI and yielded crystals that diffracted to 1.6-2.0 ? resolution. Prodrugs of these compounds possess antimycobacterial activity against H37Rv, a virulent strain of human TB, with the most active compound having an MIC90 of 2.32 ± 0.04 μM. This compound demonstrates a very favorable selectivity window and represents a highly promising lead as an anti-TB agent.
Functional panchromatic BODIPY dyes with near-infrared absorption: Design, synthesis, characterization and use in dye-sensitized solar cells
Huaulmé, Quentin,Aumaitre, Cyril,Kontkanen, Outi Vilhelmiina,Beljonne, David,Sutter, Alexandra,Ulrich, Gilles,Demadrille, Renaud,Leclerc, Nicolas
supporting information, p. 1758 - 1768 (2019/08/07)
We report two novel functional dyes based on a boron-dipyrromethene (BODIPY) core displaying a panchromatic absorption with an extension to the near-infrared (NIR) range. An innovative synthetic approach for preparing the 2,3,5,6-tetramethyl-BODIPY unit is disclosed, and a versatile way to further functionalize this unit has been developed. The optoelectronic properties of the two dyes were computed by density functional theory modelling (DFT) and characterized through UV-vis spectroscopy and cyclic voltammetry (CV) measurements. Finally, we report preliminary results obtained using these functional dyes as photosensitizers in dyesensitized solar cells (DSSCs).
High add valued application of turpentine in crop production through structural modification and qsar analysis
Gao, Yanqing,Li, Jingjing,Li, Jian,Song, Zhanqian,Shang, Shibin,Rao, Xiaoping
, (2018/02/17)
Turpentine is a volatile component of resin, which is an abundant forest resource in Southern China. As one of the most important components, the integrated application of-pinene has been studied. The broad-spectrum evaluation of -pinene and its analogues has, therefore, been necessary. In an attempt to expand the scope of agro-activity trials, the preparation and the evaluation of the herbicidal activity of a series of -pinene analogues against three agricultural herbs were carried out. In accordance with the overall herbicidal activity, it is noteworthy that compounds 6k, 6l, and 6m demonstrated extreme activity with IC50 values of 0.065, 0.065, and 0.052 mol active ingredients/hectare against E. crus-galli. The preliminary structure-activity relationship (SAR) was analyzed and the compounds with the appropriate volatility and substituent type that had beneficial herbicidal activity were analyzed. Simultaneously, the quantitative structure-activity relationship (QSAR) model was built and the most important structural features were indicated, which was, to a certain extent, in line with the SAR study. The study aimed to study the application of the forest resource turpentine in agriculture as a potential and alternative approach for comprehensive utilization.