78-95-5 Usage
Chemical Properties
colourless to dark yellow liquid
Uses
Different sources of media describe the Uses of 78-95-5 differently. You can refer to the following data:
1. Couplers for color photography, enzyme
inactivator, insecticides, perfumes, intermediate,
organic synthesis, tear gas, polymerization of vinyl
monomers.
2. Manufacture of couplers for color photography;
intermediate in manufacture of
perfumes, antioxidants, drugs, plant growth
regulators, defoliants, and herbicides
3. Chloroacetone was used in the synthesis of double-chain nonionic surfactants with an acid decomposition function via acid-catalyzed condensation with fatty alcohols (octyl, decyl and dodecyl). It was also used in the synthesis of meso-tetramethyl tetrakis-(4-phenoxy acetone)calix[4]pyrrole. It can also be used to make dye couplers for color photography and used in the Feist-Benary synthesis of furans.
Definition
A lachrymator.
Synthesis Reference(s)
Journal of the American Chemical Society, 77, p. 5274, 1955 DOI: 10.1021/ja01625a016Synthesis, p. 188, 1987 DOI: 10.1055/s-1987-27886
General Description
A yellow-colored liquid with an irritating pungent odor. Light sensitive, but stabilized with the addition of small amounts of water and/or calcium carbonate. Slightly soluble in water and denser than water. Vapors much heavier than air. Irritates skin and eyes. Very toxic by ingestion or inhalation. Used to make other chemicals. A lachrymator.
Air & Water Reactions
Highly flammable. Water soluble.
Reactivity Profile
CHLOROACETONE turns dark and resinifies on prolonged exposure to light [Merck]. This occurred in a bottle during storage for two years on a shelf in diffused light. A few days after the bottle was moved, Chloroacetone exploded [Ind. Eng. News 9: 184(1931)]. Is stabilized by addition of 0.1% water or 0.1% CaCO3.
Hazard
Strong irritant to tissue, eyes, and mucous
membranes; toxic by ingestion and skin contact.
Upper respiratory tract irritant.
Health Hazard
TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will 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 and poison 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.
Flammability and Explosibility
Flammable
Safety Profile
Poison by inhalation,
ingestion, and skin contact. Mutation data
reported. A lachrymator poison gas. See also
CHLORINATED HYDROCARBONS,
ALIPHATIC; ACETONE. Flammable
when exposed to heat or flame, or oxidizers. Old material can explode. When heated to
decomposition it emits highly toxic fumes.
Purification Methods
Dissolve it in water and shake it repeatedly with small amounts of diethyl ether which extracts, preferentially, 1,1-dichloroacetone present as an impurity. The chloroacetone is then extracted from the aqueous phase using a large amount of diethyl ether, and distilled at slightly reduced pressure. It is dried with CaCl2 and stored at Dry-ice temperature. Alternatively, it was stood over CaSO4, distilled and stored over CaSO4. It is steam volatile. The 2,4-dinitrophenylhydrazone forms yellow needles from EtOH with m 120o or 124o. [Beilstein 1 IV 3215.] LACHRYMATOR with toxic vapour.
Check Digit Verification of cas no
The CAS Registry Mumber 78-95-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 8 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 78-95:
(4*7)+(3*8)+(2*9)+(1*5)=75
75 % 10 = 5
So 78-95-5 is a valid CAS Registry Number.
InChI:InChI=1/C3H5ClO/c1-3(5)2-4/h2H2,1H3
78-95-5Relevant articles and documents
PHOTOINDUCED REACTIONS OF ORGANIC COMPOUNDS WITH TRANSITION METAL COMPLEXES. II. REACTION OF PtCl62- WITH ACETONE TO GIVE A ?-ACETONYL COMPLEX OF PLATINUM(IV). DETECTION OF PLATINUM(III) COMPOUNDS BY ESR
Nizova, G. V.,Serdobov, M. V.,Nikitaev, A. T.,Shul'Pin, G. B.
, p. 139 - 144 (1984)
Light irradiation of a PtCl62- solution in acetone affords a ?-acetonyl complex of platinum(IV), 2-.Prolonged irradiation yields CH3COCH2Cl and PtCl42-.The signals of a platinum(III) complex and CH3COCH2-radical are detected in the ESR spectrum of the frozen solution of PtCl62- in acetone irradiated at 77 K.The proposed mechanism of the reaction involves electron transfer from the enol tautomer of acetone to PtCl62-.
Gas-phase oxidation of CH2-=-C(CH3)CH2Cl initiated by OH radicals and Cl atoms: Kinetics and fate of the alcoxy radical formed
Rivela, Cynthia,Gibilisco, Rodrigo G.,Teruel, Mariano A.
, p. 480 - 484 (2015)
Relative kinetics of the reactions of OH radicals and Cl atoms with 3-chloro-2-methyl-1-propene has been studied for the first time at 298-K and 1-atm by GC-FID. Rate coefficients are found to be (in cm3-molecule-1-s-1): k1 (OH-+-CH2-=-C(CH3)CH2Cl)-=-(3.23-±-0.35)-×-10-11, k2 (Cl-+-CH2-=-C(CH3)CH2Cl)-=-(2.10-±-0.78)-×-10-10 with uncertainties representing-±-2σ. Product identification under atmospheric conditions was performed by solid phase microextraction/GC-MS for OH reaction. Chloropropanone was identified as the main degradation product in accordance with the decomposition of the 1,2-hydroxy alcoxy radical formed. Additionally, reactivity trends and atmospheric implications are discussed.
Towards sustainable manufacture of epichlorohydrin from glycerol using hydrotalcite-derived basic oxides
Lari, Giacomo M.,Pastore, Giorgio,Mondelli, Cecilia,Pérez-Ramírez, Javier
supporting information, p. 148 - 159 (2018/01/12)
Commercial two-step processes to convert glycerol into epichlorohydrin are more benign compared to the predominant industrial route starting from propene in terms of materials requirements and CO2 emissions. Still, the use of alkali hydroxides in stoichiometric amounts in the second reaction, i.e., the dehydrochlorination of the dichloropropanol intermediate, leads to the formation of large amounts of salt wastes, thus limiting the greenness of the technology. Here, we show for the first time that the latter transformation can be selectively conducted in the gas phase in the presence of a heterogeneous hydrotalcite-derived mixed oxide of Al and Mg. Upon reaction, the lamellar solid is rehydrated to a hydrotalcite-like compound, which can effectively activate the alcoholic group of dichloropropanol owing to its strong Br?nsted basic character and moderately high surface area. In-depth characterisation of the porous, compositional, structural and acid/base properties demonstrates that the HCl formed during the reaction causes the progressive exchange of interlayer OH groups by Cl atoms, thus gradually diminishing the reactivity of the material. Facile calcination restores the original mixed oxide structure and is shown to enable three equivalent consecutive reaction runs. Since the HCl evolved along with water upon regeneration can be recycled in the first step of the process, i.e., glycerol hydrochlorination, our approach paves the way for a waste-free and more atom efficient biobased epichlorohydrin production process.
Reactions of diazo ketones with activated unsaturated compounds in the presence of gallium trichloride
Novikov,Tomilov,Nefedov
, p. 404 - 408 (2015/01/08)
Diazoacetone reacts with methyl acrylate in the presence of anhydrous GaCl3 to give isomeric methyl 2-acetylcyclopropanecarboxylates rather than pyrazolines obtained from diazo esters or by noncatalytic reactions. In a similar reaction, diazoacetophenone yields methyl 2-benzoylcyclopropanecarboxylates, benzoylmethyl acrylate, and benzoylmethyl 2-benzoylcyclopropanecarboxylate via partial transesterification. Addition of an equimolar amount of GaCl3 to diazoacetone in the system CH2Cl2-HCl-H2O unexpectedly produces 4,5-dimethylfuran-3(2H)-one and 1,1'-oxybis(propan-2-one).
