EXPERIMENT

1

ABAD • CUA • FELICITA • LICERIO • QUINE • SUMABAT

DISTILLATION OF ALCOHOLIC BEVERAGES

ALCOHOLIC

BEVERAGES ? Main content:

Ethyl alcohol / Ethanol produced from fermentation.

ETHANOL

C2H6O= =

FERMENTATION?

GLUCOSE

ENERGYCO2

ETHANOL

Sugar extracted from:fruits, berries, grains

Produces 5-10% alcohol

How about those with 40%+

Alcohol content?DISTILLATION Separate water from alcohol = increase in

alcohol concentration

Difference in the volatility of alcohol and water is utilized

S

liquid vapour

liquid

Proof• Historical origins: gunpowder test• UK: 100 proof = 57.15% ABV• US: 100 proof = 50% ABV%

Alcohol by

volume

• number of milliliters of pure ethanol present in 100 millilitres of solution

• The ABV standard is used worldwide.%

ALCOHOL BY

WEIGHT

• weight of alcohol divided by the total weight of beverage

*International Organization of Legal Metrology

Measuring alcohol

content?

Upon ingestion, alcohol is rapidly absorbed in the gastrointestinal tract.

No enzyme to facilitate its digestion.

Alcohol level in blood rises in a relatively short time.

Functions of the brain are depressed – judgement and self-criticism.

Drinker gradually becomes less alert, awareness of environment become dim and hazy.

Muscular coordination deteriorates, and sleep is facilitated.

Effects of alcohol

intoxication?

Republic Act 10586 Anti-Drunk and

Drugged Driving Act

R-O-H

CH3CH2OH

volatile, flammable, colorless liquid It is completely miscible with water and

organic solvents and is very hydroscopic. Boiling point: 78.37 °C Forms only one hydrogen bond for each

molecule compared to a water molecule (2 hydrogen bonds). thus, ethanol boils faster than water

ETHANOL?

Ginebra san miguel? The largest selling gin in the world in 2012,

according to Drinks International

80 proof

Gin, distilled beverage/spirit which derives its predominant flavour from juniper berries (Juniperus communis).

In the United States, gin is defined as an alcoholic beverage of no less than 40% ABV (80 proof)

Process of vaporizing a liquid, condensing the vapor, and collecting the condensate in another container (Engel, Pavia, Kriz, & Lampman, 2011).

Purification

Separation of liquids with different volatilities.

DISTILLATION?SIMPLE DISTILLATION Difference in boiling points

is very large.

Distillation flask, condenser, receiving flask.

FRACTIONAL DISTILLATION fractionating column

inserted between the distillation flask and the distillation head

Increase surface area in contact with condenser.

As vapours ascend the column, high boiling components are condensed and returned to the flask.

SIMPLE DISTILLATION

SET-UP?

FRACTIONAL DISTILLATION SET-

UP?

At any given temperature, a liquid is in equilibrium with its vapor

Thus, an increase in temperature = increase in liquid’s vapor pressure

BOILING POINT is the state when the Liquid’s vapor pressure = applied pressure (atmospheric pressure)

Sensitive to changes in external pressure Depends on liquid’s polarity, molecular mass, and

over-all size and shape of molecule Intermolecular interactions are disrupted, for a liquid

to boil. Boiling point of a liquid is a measure of its

VOLATILITY, propensity to vaporize

example. Methanol (b.p. 64.7 °C) Ethanol (b.p. 78.5 °C)

thus, methanol is more volatile than ethanol

BOILING POINT?

STEAM DISTILLATION For volatile compounds

immiscible with water

Purification of mixture dome through codstillation

Since immiscible with each other, properties of one component will not affect properties of the other

Isolation of essential oils from plants

OTHER FORMS OF

DISTILLATION?VACUUM DISTILLATION For high boiling-point

liquids

Apparatus connected to a vacuum

Results in a lowered boiling point due to reduced pressure.

Receiving flask has three or four receptacles to collect different fractions.

Distillation is a purification technique in which compounds with different boiling points can be separated by controlled heating.  Vapors from a sufficiently heated sample can be recondensed and collected, purer than the initial mixture.The liquid which has not vaporized is called theresidue, and the liquid which is collected in the receiver is called thedistillate.Since not all chemicals distill the same way, there are several distillation techniques can be preferred depending on the nature of constituents to be purified or to be separated. These include simple distillation, fractional distillation, steam distillation and vacuum distillation.A simple distillation (figure 2) is for purifying liquids of one component (separating nonvolatile liquid impurity or to purify a liquid from solid contaminants), multiple liquids where the differences in boiling points is very large (a low boiling liquid from a high boiling liquid)(b.p difference around 50-70°C). Simple distillations are not effective in removing multiple solvents from one another with a high degree of success.In fractional distillation (figure 3), a fractionating column is inserted between the distillation flask and the distillation head. The fractionating column provides a large surface area in which the mixture can be continuously vaporized and condensed.The principle of a fractionating column is that, as the vapours ascend the column from the boiling mixture below, the high boiling components are condensed and returned to the flask, the ascending column of vapour being thus steadily “scrubbed” by the descending column of liquid condensate. The ascending column of the vapour becomes therefore steadily richer in the lowest boiling component, and the descending column of condensate steadily richer in the highest boiling component.Figure 1 represents the typical curve for simple and fractional distillation. In an ideal fractional distillation, two distinct fractions are obtained. The first corresponds to the component with the lower boiling point and the second to the high-boiling point component. What characterizes a good fractional distillation is the sudden increase in temperature between both fractions, or in other words, a very small volume distilled at temperatures other than the boiling points of the pure liquids. In simple distillation, a much more gradual increase in temperature is observed, reflecting the impure nature of the distillate

                                                   

Figure 1. Simple and fractional distillation curvesSteam distillation is used for separating mixtures of chemicals such as oils, resins, hydrocarbons, etc. which are insoluble in water and may decompose at their B.P.Vacuum distillation is used for separating liquids boiling above 200◦C

Iron stand (2)

Burette clamp

Bunsen burner

Distilling flask

Condenser Distilling

head Receiver

adaptor Lubricant Glycerol Boiling

Chips (3) Thermomet

er

Rubber tubing

Water pump Funnel Graduated

cylinder Watch glass

MATERIALS?

PROCEDURE?Alcoholic Beverage

(25 mL)

0.5 mL distillat

e

0.5 mL distillat

e

0.5 mL distillat

e

0.5 mL distillat

e

0.5 mL distillat

e

0.5 mL distillat

e…..

*subject to distillation (simple/fractional)*collect 0.5ml distillate*take note of temperature at first drop*take note of temperature of each 0.5 mL distillate*stop collection upon reaching 95 °C

Flammability Test

Flammable Non-Flammable

% Ethanol

*add volume of all flammable distillate

CLASS DATA

%Alcohol by Volume

TRUE VALUE = 40%

Group Number:

Simple Distillation

Fractional Distillation

% Error % Error

1 44% - 10%

2 - 34% 15%

3 46% - 15%

4 - 40% 0%

5 34% - 15%

6 - 34% 15%

7 40% - 0%

8 - 84% 110%

9 48% - 20%

10 - 70% 75%

11 50% - 25%

12 - 42% 5%

DISTILLATION CURVE

Fractional distillation characterized by a sudden

increase in the temperature between two fractions

boiling point of more volatile and boiling point of less volatile liquid

Simple distillation characterized by gradual

increase in temperature, reflects the impure nature of the distillate.

How data supports THE conclusion ...

Simple distillation yielded less ethanol percent compared to fractional distillation.

Flammability test Fractional distillation will yield %ethanol closer to the true value

1. The alcoholic beverage was not equal to 25 ml

2. Spillage during transfer of liquids and when collecting from the condenser.

3. Improper heating techniques causing quick temperature increase.

4. Was not able to observe properly during flammability test.

5. Miscalculations or misreadings in gathering data.

SOURCES OF ERROR

ATTAINMENT OF OBJECTIVES...

1. Separate ethanol from alcoholic beverage using distillation.

2. Determine percent ethanol in alcoholic beverage.

3. Compare simple and fractional distillation.

RECOMMENDATIONS...

1. Make sure the apparatus to be used is cleaned and free from anything that may alter the % yield.

2. Amount of heat must be made constant as much as possible.

3. Test tubes should be well-calibrated.

ReferencesBettelheim, F. A. (2013). Introduction to general, organic, and biochemistry. Belmont, CA : Brooks/Cole, Cengage Learning.

Bettelheim, F. A., & Landesberg, J. M. (2010). Laboratory experiments for introduction to general, organic, and biochemistry. Australia : Brooks/Cole Cengage Learning.

Boulder, U. O. (2014, August 12). Distillation. Retrieved from Organic Chemistry: http://orgchem.colorado.edu/Technique/Procedures/Distillation/Distillation.html

Boulton, C. (2001). Brewing yeast and fermentation . Oxford: Blackwell Science.

Engel, R. G., Pavia, D. L., Kriz, G. S., & Lampman, G. M. (2011). Introduction to organic laboratory techniques : a small scale approach. Belmont, CA : Thomson Brooks/Cole.

Geankoplis, C. J. (2003). Transport processes and separation process principles. Upper Saddle River, NJ : Prentice Hall Professional Technical Reference.

Lower, S. (2013, july 31). Raoult's law and distillation. Retrieved from chem1 virtual textbook: http://www.chem1.com/acad/webtext/solut/solut-5.html

Martin, S. F., & Gilbert, J. (2011). Organic chemistry lab experiments : miniscale and microscale. Australia : Brooks/Cole Cengage Learning.

Palleros, D. R. (2000). Experimental organic chemistry. New York : Wiley.

Pedersen, S. F., & Myers, A. M. (2011). Understanding the principles of organic chemistry : a laboratory course. Belmont, CA : Brooks/Cole Cengage Learning.

Rajasekaran, A. (2006, may 25). Fractional distillation of binary solvent mixture.

Retrieved from Pharmaceutical Information, Articles and Blogs: http://www.pharmainfo.net/reviews/fractional-distillation-binary-solvent-mixture

Schmid, A. W. (2008). The hospitality manager's guide to wines, beers, and spirits. Upper Saddle River, N.J: Pearson/Prentice Hall.