108-22-5 Usage
Description
Isopropenyl acetate is a kind of organic compound, corresponding to the acetate ester of the enol tautomer of acetone. It appears as a clear, colorless liquid with a fruit-like odor. It has a moderate solubility in water and a low flash point. It has a lower density than water but heavier vapor than the air. It is widely used as an industrial and consumer based solvent. For example, it is used as the principal precursor to acetylacetone and some other important chemicals. It can also be used as a kind of food additive. Moreover, it is also applied to coatings, cleaning fluids and printing inks as well as used as cosmetic and personal care solvent and fragrance solvents. It has various kinds of advantages including being a good resin solvent, belonging to a Non-HAP (hazardous air pollutant solvent), having mild odor and undergoing fast evaporating. It is manufactured through treatment of acetone with ketene. However, it is highly flammable and of certain toxicity, therefore proper protective measures should be used during the operation.
References
https://pubchem.ncbi.nlm.nih.gov/compound/Isopropenyl_acetate#section=Artificial-Sources
http://www.monumentchemical.com/documents/IPAc_TDS_MC.pdf
https://en.wikipedia.org/wiki/Isopropenyl_acetate
Chemical Properties
clear colorless to very slightly yellow liquid
Uses
Different sources of media describe the Uses of 108-22-5 differently. You can refer to the following data:
1. Reagent for acylation of potential enols.
2. Iodine in isopropenyl acetate is a unique catalyst for the acetylation of a variety of alcohols, phenols and amines under solvent free conditions. It is used as a solvent for cellulose, plastics, oil and fats. It is also a building block used for various organic synthesis.
Synthesis Reference(s)
Journal of the American Chemical Society, 88, p. 2054, 1966 DOI: 10.1021/ja00961a043
Air & Water Reactions
Highly flammable. Soluble in water.
Reactivity Profile
Isopropenyl acetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Hazard
Flammable, dangerous fire risk.
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. May polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Flammability and Explosibility
Flammable
Safety Profile
Moderately toxic by
ingestion. A skin, eye, and mucous
membrane irritant. A very dangerous fire
hazard when exposed to heat or flame; can
react vigorously with oxidizing materials. To
fight fire, use alcohol foam, CO2, dry
chemical. When heated to decomposition it
emits acrid smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 108-22-5 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 8 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 108-22:
(5*1)+(4*0)+(3*8)+(2*2)+(1*2)=35
35 % 10 = 5
So 108-22-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O2/c1-3-4-7-5(2)6/h3H,1,4H2,2H3
108-22-5Relevant articles and documents
-
Charles et al.
, p. 2084 (1959)
-
Preparation of various enantiomerically pure (benzotriazol-1-yl)- and (benzotriazol-2-yl)-alkan-2-ols
Pchelka, Beata K.,Loupy, Andre,Petit, Alain
, p. 2516 - 2530 (2006)
(S)-(-)-(Benzotriazol-1-yl)- and (S)-(-)-(benzotriazol-2-yl)-alkan-2-ols 7a-9a, 7b-9b and their (R)-(+)-acetates 10a-12a and 10b-12b were prepared in high enantiomeric excess via lipase from Pseudomonas fluorescens (Amano AK) catalyzed enantioselective acetylation of racemic alcohols 4a-6a and 4b-6b with vinyl acetate in tert-butyl methyl ether or toluene at 23 °C. The enantioselectivity of this transformation was dependent on the length of the alkyl chain with E-values ranging from 30 to 57. Several benzotriazole substituted ketones 1a-3a and 1b-3b were synthesized from 1H-benzotriazole and corresponding haloketones. These compounds were stereoselectively reduced with Baker's yeast in water or in organic solvent containing 5% v/v of water at 30 °C to give the (S)-(-)-alcohol. Better stereoselectivity was observed in the kinetic resolution of racemic alcohols 4a-6a and 4b-6b (ee = 69-92% at 44-52% conversion) compared to reduction of corresponding prochiral ketones 1a-3a and 1b-3b with Baker's yeast (ee = 40-67% at 39-89% conversion). Enhanced enantioselectivities were observed at lower temperatures.
Suzuki et al.
, p. 3707,3708 (1969)
Energy-saving efficient isopropenyl acetate synthesis method
-
Paragraph 0050-0055, (2017/04/14)
The invention discloses an energy-saving efficient isopropenyl acetate synthesis method which comprises the following steps: (1) feeding acetic acid into a container, performing heating treatment on the acetic acid so as to generate an ethenone gas from the acetic acid in a catalytic cracking manner, introducing the ethenone gas into a cooler; (2) feeding an acetone solution into a mixing dish, simultaneously feeding a catalyst into the mixing dish, mixing, uniformly stirring, pumping the mixed liquid into the cooler by using a metering pump; (3) conveying the mixed gas in the cooler into a synthesis reaction tower, and enabling the mixed gas to generate a reaction gas in the synthesis reaction tower; and (4) condensing the generated reaction gas so as to obtain a coarse product, refining the coarse product, cooling, crystallizing and drying, thereby obtaining a product. According to the energy-saving efficient isopropenyl acetate synthesis method disclosed by the invention, the ethenone gas and the acetone steam are enabled to have homogeneous reaction directly, so that the reaction efficiency is effectively improved, the transfer amount of acetone is greatly reduced, and the comprehensive utilization rate is increased.
Highly efficient dynamic kinetic resolution of secondary aromatic alcohols with low-cost and easily available acid resins as racemization catalysts
Cheng, Yongmei,Xu, Gang,Wu, Jianping,Zhang, Chensheng,Yang, Lirong
supporting information; experimental part, p. 2366 - 2369 (2010/06/13)
A new and efficient dynamic kinetic resolution (DKR) process of secondary aromatic alcohols was developed with acid resins as racemization catalysts. Acid resin CD8604 was shown to have excellent racemization activity and good biocompatibility. When employing CD8604 and complex acyl donors as racemization catalyst and acyl donor, respectively, enantiomerically pure aromatic acetate was obtained with excellent yield and ee values through the DKR process. It is noteworthy that the system could be reused more than 10 times with little loss of yield and ee value.
