3016 Oxidation of ricinoleic acid (from castor oil) with KMnO 4 to azelaic acid

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1 6 Oxidation of ricinoleic acid (from castor oil) with KMnO 4 to azelaic acid CH -(CH ) OH (CH ) -COOH KMnO 4 /KOH HOOC-(CH ) -COOH C H 4 O (.) KMnO 4 KOH (.) (6.) C H 6 O 4 (.) Classification Reaction types and substance classes oxidation alkene, carboxylic acid, renewable resources Work methods heating under reflux, stirring with magnetic stir bar, stirring with KPG stirrer, adding dropwise with an addition funnel, shaking out, extracting, evaporating with rotary evaporator, filtering, recrystallizing, heating with oil bath Instruction (batch scale 4 mmol) Equipment ml round-bottom flask, ml three-neck flask, reflux condenser, internal thermometer, addition funnel with pressure balance, heatable magnetic stirrer, magnetic stir bar, KPG-stirrer, 4 ml beaker, ml beaker, ml Erlenmeyer flask, separating funnel, rotary evaporator, Buechner funnel, suction flask, desiccator, oil bath Substances castor oil potassium hydroxide potassium permanganate ethanol (bp C) tert-butyl methyl ether (bp C) conc. sulfuric acid Celite (filter help) ice 4 g (etwa 4 mmol) 4. g ( mmol).6 g ( mmol) 4 ml ml ml g

2 Preparation of ricinoleic acid from castor oil Reaction 4 g (about 4 mmol) castor oil are filled in a ml round bottom flask with magnetic stir bar and reflux condenser, containing a solution of. g (6 mmol) KOH in 4 ml ethanol. The mixture is heated under stirring for 4 hours under reflux. Work up The cooled mixture is poured in a 4 ml beaker containig g ice. Then carefully, under strong stirring with a glas rod the solution of ml conc. sulphuric acid in 6 ml water is added until clear acidic reaction; thereby the crude ricinoleic acid separates as an oil. The phases are separated in the separating funnel, the aqueous phase is extracted with ml tertbutyl methyl ether. Oil and ether extract are combined and the solvent is evaporated at a rotary evaporator. The ricinoleic acid remains as oily residue. Yield: g (etwa 4 mmol) Oxidation of the ricinoleic acid Reaction g (4 mmol) crude ricinoleic acid are dissolved in a ml Erlenmeyer flask, containing a solution of. g (6 mmol) KOH in ml water. In a ml three-neck flask equipped with KPG-stirrer and internal thermometer,.6 g ( mmol) potassium permanganate are dissolved in ml water at an internal temperature of about C. Under strong stirring the alkaline solution in the Erlenmeyer flask is added at once to the ricinoleic acid in the threeneck flask. A reflux condenser is installed on the free openingof the flask and the mixture is stirred without further heating or cooling until the colour of permanganate has disappeared (about minutes). For a better examination of the colour, a small sample of the solution is diluted in a test tube with water. Work up The reflux condenser is replaced for a short time through an addition funnel with pressure balance. Under stirring a solution of ml conc. sulfuric acid in ml water is slowly added dropwise. The reaction mixture with the reflux condenser is heated in an oil bath for minutes to about C in order to reach a better conglomeration and precipitation of the product. The mixture is filtered over a large Buechner funnel, the filterpaper of which has been moistened and covered with a layer of Celite. The filter residue is boiled in a ml beaker with ml water and again filtered. The combined filtrates are concentrated under reduced pressure at a rotary evaporator (about hpa) to - ml. The flask is put in an ice bath, the product crystallizes. It is sucked off, washed with little cold water and dried in the desiccator. Crude yield: 4. g For purification the crude product is dissolved in about ml hot water and filtered while hot. It is slowly cooled down to room temperature, again cooled in an ice bath, sucked off, then washed with ml ice water and dried in the desiccator. Yield:. g (. mmol, %); colourless solid, mp 4-6 C

3 Waste management Waste disposal Waste aqueous phase from preparation of the ricinoleic acid evaporated tert-butyl methyl ether (might contain ethanol) filter residue with Celite aqueous filtrates from preparation of the azelaic acid evaporated water Disposal solvent water mixtures, halogen free organic solvent, halogen free solid waste, free from mercury, containing heavy metal solvent water mixtures, halogen free sewerage system Time hours Break After isolation of the ricinoleic acid After sucking off the MnO Before recrystallization Degree of difficulty Medium Analytics TLC TLC-conditions: adsorbant: eluent: visualization: Merck silica gel 6 F 4, x cm ethanol Tillmanns-reagent-TLC-solution. The spots appear as pink marks after the plate was dipped in the solution and dried by a slight heating with a hot-air dryer. reagent solution:.%ige solution from,6-dichlorophenolindophenol sodium salt in % ethanol R f (ricinoleic acid). R f (azelaic acid).6

4 TLC a) ricinoleic acid b) crude product c) azelaic acid a b c C NMR spectrum of the pure product (6. MHz, DMSO-D 6 ) 4 6 HOOC COOH δ (ppm) Assignment. C-, C-.6 C-. C-4, C-6. C-, C-.4 COOH. solvent 4

5 H NMR spectrum of the crude product ( MHz, DMSO-D 6 ) H NMR spectrum of the pure product ( MHz, DMSO-D 6 ) 4 6 HOOC COOH δ (ppm) Multiplicity Number of H Assignment. m 6 4-H, -H, 6-H.4 m 4 -H, -H. t, J =. Hz 4 -H, -H ~ bs COOH.4 solvent

6 IR spectrum of the crude product (KBr) 6 Transmission [%] 4 4 Wellenzahl [cm - ] IR spectrum of the pure product (KBr) 6 Transmission [%] 4 4 Wellenzahl [cm - ] (cm - ) Assignment - O-H-valence, carboxylic acid 6, C-H-valence, alkane, O-H 4 C=O-valence, carboxylic acid 6

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