Acetone

Acetone, with the CAS register number 67-64-1, is a clear colorless liquid with a sweetish odor. The substance which is the organic compound with the formula C₃H₆O has EINECS register number 200-662-2. Acetone is soluble in water. Acetone can form explosive mixtures with chromic anhydride, chromyl alcohol, hexacholromelamine, hydrogen peroxide, permonosulfuric acid, potassium terbutoxide and thioglycol. You should keep Acetone away from heat, sparks and flame. What's more, Acetone should be stored in a cool, dry place, and its container should be kept closed when not in use.

Properties: Acetone is the most representative compound of aliphatic ketone, which has the typical reaction of ketone. For example, Acetone reacts with sodium hydrogensulfite to give additive product of colorless crystalline, reacts with hydrogen cyanide to generacte acetone cyanohydrin [(CH₃)₂C(OH)CN]. In addition, Acetone can be restored by reductant into isopropyl alcohol and pinacolone. Acetone is relatively stable with oxidan, however, reacts with strong oxidizer oxidation, like alkaline potassium permanganate or chromium acid, can generate acetic acid, formic acid, carbon dioxide and water.

When Acetone coexists with alkali, it will generate diacetone alcohol. Otherwise, it can be used to produce bisphenol A with phenol using acid as the catalyst. Acetone reacts with Grignard reagent to generates tertiary alcohol. Meanwhile, Acetone will happen a thermal decomposition at 500~1000 °C to give ethenone, give isobutylene and aldehydes at 170~260 °C, moreover, generate isobutylene and acetic at 300~350 °C.

Production: Previously, Acetone was produced by the dry distillation of acetates, for example calcium acetate. During World War I, Acetone was produced via bacterial fermentation, as developed by Chaim Weizmann in order to help the British war effort. This Acetone Butanol Ethanol process was abandoned due to the small yields. Nowadays, Acetone is produced directly or indirectly from propylene. Approximately 83 % of Acetone is produced via the cumene process, as a result, acetone production is tied to phenol production. In the cumene process, benzene is alkylated with propylene and the resulting cumene (isopropylbenzene) is oxidized by air to give phenol and Acetone:

Besides, Acetone can be produced by acetylene with water vapor using zinc oxide as the catalyst.

2 C₂H₂ + 3 H₂O → (CH₃)₂CO + CO₂↑ + 2 H₂↑

In addition, oxidation or dehydrogenation of isopropyl alcohol can be used to prepare Acetone. The isopropyl alcohol reacts with hydrogen peroxide to give Acetone. The isopropyl alcohol and acraldehyde can be used to generate Acetone.

Uses: Acetone is also used extensively as a solvent for the safe transporting and storing of acetylene, which cannot be safely pressurized as a pure compound. Acetone is used in a variety of general medical and cosmetic applications and is also listed as a component in food additives and food packaging. In the laboratory, Acetone is used as a polar aprotic solvent in a variety of organic reactions, such as SN₂ reactions.

Acetone can be used as the active ingredient in nail polish remover and as paint thinner. Acetone is a good solvent for most plastics and synthetic fibers including those used in laboratory bottles made of polystyrene, polycarbonate and some types of polypropylene. It also can be used as a solvent and production of methyl methacrylate and bisphenol A. The procedures of producing methyl methacrylate and bisphenol A are as the following:

(CH₃)₂CO + HCN → (CH₃)₂C(OH)CN
(CH₃)₂C(OH)CN + CH₃OH → CH₂=(CH₃)CCO₂CH₃ + NH₃
(CH₃)₂CO + 2 C₆H₅OH → (CH₃)₂C(C₆H₄OH)₂ + H₂O

Many millions of kilograms of Acetone are consumed in the production of the solvents methyl isobutyl alcohol and methyl isobutyl ketone. These products arise via an initial aldol condensation to give diacetone alcohol.

2 (CH₃)₂CO → (CH₃)₂C(OH)CH₂C(O)CH₃

When you are using Acetone, you should be very cautious about it. Acetone is highly flammable and irritant, which is irritating to eyes. If repeated exposure, Acetone may cause skin dryness or cracking. Its vapours may cause drowsiness and dizziness. In addition, you should keep its container in a well-ventilated place and keep Acetone away from sources of ignition - No smoking.

Descriptors computed from structure of Acetone:
(1)Canonical SMILES: CC(=O)C
(2)InChI: InChI=1S/C3H6O/c1-3(2)4/h1-2H3
(3)InChIKey: CSCPPACGZOOCGX-UHFFFAOYSA-N

Toxicity of Acetone:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	intraperitoneal	8gm/kg (8000mg/kg)	BEHAVIORAL: COMA GASTROINTESTINAL: ALTERATION IN GASTRIC SECRETION	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 18, Pg. 218, 1884.
dog	LDLo	oral	8gm/kg (8000mg/kg)	BEHAVIORAL: ATAXIA BEHAVIORAL: COMA MUSCULOSKELETAL: JOINTS	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 18, Pg. 218, 1884.
dog	LDLo	subcutaneous	5gm/kg (5000mg/kg)		Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 18, Pg. 218, 1884.
guinea pig	LD50	skin	> 9400uL/kg (9.4mL/kg)		Toxicology and Applied Pharmacology. Vol. 7, Pg. 559, 1965.
guinea pig	LDLo	subcutaneous	5gm/kg (5000mg/kg)		Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933.
human	TCLo	inhalation	500ppm (500ppm)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943.
man	LDLo	unreported	1159mg/kg (1159mg/kg)		"Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man	TCLo	inhalation	440ug/m3/6M (0.44mg/m3)	BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(8), Pg. 42, 1977.
man	TCLo	inhalation	10mg/m3/6H (10mg/m3)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(8), Pg. 42, 1977.
man	TCLo	inhalation	12000ppm/4H (12000ppm)	GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: MUSCLE WEAKNESS	Annals of Occupational Hygiene. Vol. 16, Pg. 73, 1973.
man	TDLo	oral	2857mg/kg (2857mg/kg)	BEHAVIORAL: COMA KIDNEY, URETER, AND BLADDER: OTHER CHANGES	"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 64, 1969.
man	TDLo	oral	2857mg/kg (2857mg/kg)	BEHAVIORAL: COMA	Diabetes. Vol. 15, Pg. 810, 1966.
mouse	LC50	inhalation	44gm/m3/4H (44000mg/m3)		Current Toxicology. Vol. 1, Pg. 47, 1993.
mouse	LD50	intraperitoneal	1297mg/kg (1297mg/kg)		Shell Chemical Company. Unpublished Report. Vol. -, Pg. 1, 1961.
mouse	LD50	oral	3gm/kg (3000mg/kg)		Pharmaceutical Chemistry Journal Vol. 14, Pg. 162, 1980.
mouse	LDLo	intravenous	4gm/kg (4000mg/kg)		FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 86, 1970.
rabbit	LD50	oral	5340mg/kg (5340mg/kg)		FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 86, 1970.
rabbit	LDLo	intravenous	1576mg/kg (1576mg/kg)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Journal of Pharmacology and Experimental Therapeutics. Vol. 33, Pg. 175, 1928.
rabbit	LDLo	skin	20mL/kg (20mL/kg)		Union Carbide Data Sheet. Vol. 5/7/1970,
rat	LC50	inhalation	50100mg/m3/8H (50100mg/m3)		American Industrial Hygiene Association Journal. Vol. 20, Pg. 364, 1959.
rat	LD50	intravenous	5500mg/kg (5500mg/kg)		Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 1, 1974.
rat	LD50	oral	5800mg/kg (5800mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: TREMOR	Journal of Toxicology and Environmental Health. Vol. 15, Pg. 609, 1985.
rat	LDLo	intraperitoneal	500mg/kg (500mg/kg)	BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: MUSCLE WEAKNESS KIDNEY, URETER, AND BLADDER: RENAL FUNCTION TESTS DEPRESSED	Journal of Pharmacy and Pharmacology. Vol. 11, Pg. 150, 1959.