Synthesis of Acetone

ACETONE

Simplest & most imp. ketone

Ketone

most stable organic grp

• Dimethyl ketone

• Propanone

• β-Ketopropan

• Dimethyl formaldehyde

ACETONE SYNONYMS

2-Propanone / Propan-2-one

ACETONE IUPAC

• Colorless, flammable liquid (ignites upon exposure to fire), boiling at 133 °F (56.2 °C). 

• Many fats, resins, and organic materials dissolve easily in it

• Dissolves/miscible in water.

Acetone characteristics

Ketonemia

Acetone present in blood

Ketonuria

Acetone present in urine

• Used to make artificial fibers, explosives, resins, paints, inks, cosmetics (including nail-polish remover), coatings, and adhesives.

• Solvent for extraction

• Gas sterilization

• Also used as a denaturant (same with Methanol & Benzene) in denatured alcohol.

• Used in defatting prior to chemexfoliation (skin peeling through chemicals) 

ACETONE: USES

sleeping sickness

Tsetse flies (vector of the parasitic protozoan known to produce the often fatal disease called

Acetone, Carbon dioxide, Octenol

Substance attracted by Tsetse flies

• Phenol Process or Hock Process

CUMENE PROCESS aka

• Benzene (reactant) then reacts to another reactant Propene aka Propylene to form Cumune aka Isopropylbenzene (intermediate product) then it will interact with Oxygen to form Cumene hyperoxide (very unstable) then it will react to an acid like dil. H2SO4 Sulfuric acid in the presence of H20 to break it into Phenol and Acetone (83%) 

CUMENE PROCESS

Hydration and Oxidation

WACKER-HOECHST PROCESS 2 parts

• Propylene aka. Propene it will interact with H20 hence the process is Hydration then it will form 2-Propanol / Propan-2-ol (a 2° alcohol)

When an alkene (Propylene) reacts with H2O its forms a 2° alcohol

WACKER-HOECHST PROCESS Hydration

• When (2-propanol) 2° alcohol oxidize it forms a ketone (Acetone)

WACKER-HOECHST PROCESS Oxidation

Pyridine, CrO3 chromate, and DCM 

WACKER-HOECHST PROCESS Other oxidizing agent that can be used

• Through the process of Pyrolysis (used of heat)

• Performed in the actual exp. by using Ca acetate (yields more acetone) and Na acetate then applying heat

DRY DISTILLATION OF ACETATES

ACETONE-BUTANOL-ETHANOL FERMENTATION

aka. ABE Fermentation

Chaim Weizmann

ACETONE-BUTANOL-ETHANOL FERMENTATION developed by

Clostridium acetobutylicum

• ABE Fermentation

developed by Chaim Weizmann with the aid of

• RESULT: No change in the colorless solution

• If the sx is Aldehyde the + result will be Silver mirror

ACETONE AND TOLLEN’S REAGENT

BERNHARD TOLLENS

ACETONE AND TOLLEN’S REAGENT Named after

• Red Violet Solution which is negative (-)    (ketones)

• Magenta or brilliant purplish pink color solution which is positive (aldehydes) +

SCHIFF’S TEST

ACETONE WITH NaOCl (Sodium hypochlorite)

• Can be compared to Iodoform Test

• Used to distinguish Methyl ketone (means there is a methyl grp. attached to a carbonyl grp)  after oxidation 

• Brown solution

• A pale yellow precipitate of iodoform

• Ketone is not a methyl grp. since the carbonyl grp is attached to a Ethyl grp

ACETONE WITH NaOCl (Sodium hypochlorite)