To-do list before the first week

✓ Print these slides and the student manual out

✓ Read them intensively as they are main contents in the final

exam

1
ORGANIC CHEMISTRY LAB
Unit 1 – Introduction to organic synthesis laboratory

211B2, Division of Organic Chemistry

Faculty of Chemical Engineering
lvha@hcmut.edu.vn

HCMC, 08/2023
Outlines
❑ Aims and objectives

❑ Course rules

❑ Lab safety rules

❑ Apparatus

❑ Basic techniques

❑ Lab report
3
Outlines

❑ Aims and Objectives

4
Aim & Objectives

To equip the students:

 Lab safety rules

 Fundamental equipment and techniques for organic synthesis

• Principle

• Application

• Apparatus

• Problem and solution

5
Course Outline

1) Lab safety rules

2) Fundamental techniques for organic synthesis

3) Synthesis and purification procedures of organic compounds

4) Melting-point experiment

6
Materials and References

 Trần Thị Việt Hoa, Phạm Thành Quân, Trần Văn Thạnh, Kỹ thuật thực hành
tổng hợp hữu cơ, ĐH Bách Khoa TPHCM, 2006.
 Le Vu Ha, Le Xuan Tien, Nguyen Dang Khoa, Nguyen Thanh Tung, Le Thi
Hong Nhan, Student manual - Organic chemistry lab, HCMUT, 2020.
 James W. Zubrick, The Organic Chem Lab Survival Manual: A Student’s Guide
to Techniques - 8th edition, JohnWiley & Son, 2011.
 Brian S. Furniss et al., Vogel’s Practical Organic Chemistry - 5th edition,
Longman Scientific & Technology, 1989.
 Steven F. Pedersen and Arlyn M. Yers, Understanding the Principles in Organic
Chemistry: A Laboratory Course, Cengage Learning, 2011.
 Jerry R. Mohrig et al., Techniques in Organic Chemistry - 3rd edition, W. H.
Freeman and Company, 2010.
 Donald L. Pavia et al., A Small Scale Approach to Organic Laboratory
Techniques - 3rd edition, Cengage Learning, 2011.

7
Outlines

❑ Course Rules

8
Learning Strategies – Before the lab
 Prepare for the experiment (read the manual, take notes, discuss in your team)

 Spend at least 3 hours per week for the preparation

 Complete pre-lab parts of the lab report

 Prepare your safety glasses, long-sleeve safety coat, and closed-toe shoes

 Be secured by accident insurance and be healthy

9
Learning Strategies – Application for absence
 Must attend all of 12 weeks (Unauthorized absence for a day only → FAILED!!!)
 Inform your instructor of your absence before the absence day (hand-written application
letter for absence, email/SMS/call in emergencies)
 Reasons excused: health/family problems, accidents, pregnancy
 Submit evidences for the problem (before or after the absence)
 Mandatorily attend a make-up class (your instructor signs on the application form
→ go to the class and get the second signature → re-submit to your instructor)

10
 Learning Strategies – In the lab
1. Be on time (15 – 30 min late = lost 50% of the yield score, later = get ZERO!!)

2. Wear protective equipment

3. Submit your partially completed lab report to your instructor

4. Check all given equipment and glassware

5. Start your experiment

6. Discuss with your instructor

11
 Learning Strategies – After the lab
1. Clean up the lab

2. Report all damages to the on-duty group

3. Submit your product to the instructor

4. Complete post-lab parts of your lab report

12
Learning Strategies
Submit the lab report
Approved by lab instructor

Check all glassware and equipment including additional ones

Approved by lab instructor

Assemble experiment system

Approved by lab instructor

Carry out experiment

Approved by lab instructor

Submit product and check all glassware and equipments

Approved by lab instructor

Clean up the lab

 Grade Distribution

Contents Form Percentage (%)

Experimental results Product yield + Lab report + Performance in lab 30

Final exam Fill-in-the-blank, short answers, apparatus drawing 70 (!!!)

(50-70 min, pen, ruler, and calculator required, closed-
book)
Course Plan for Org.Chem.Lab.A

Week Content Note

Introduction to organic synthesis lab
1,2,3,4 liquid-phase separation, solid-phase Very important!!!
separation
DBA-1, aspirin, ethyl acetate, The groups making benzoic acid are
5,6,7,8
benzoic acid responsible for cleanup

Terpineol, DBA-2, ß-naphthol The groups making terpineol are responsible

9,10,11,12
orange, melting point for cleanup

15
Course Plan for Org.Chem.Lab.B

Week Content Note

Introduction to organic synthesis lab
1,2 liquid-phase separation, solid-phase Very important!!!
separation
DBA-1+2, aspirin, ethyl acetate, The groups making terpineol are responsible
3,4,5,6
terpineol for cleanup

16
Tasks of the cleanup groups
1. Before the lab:

- Buy and bring ice to the lab

2. In the lab

- Wash pipets

- Clean up the public places (bench, floor, sink, waste)

- Check glassware and equipment of all groups including additional ones

- Report problems and damages to your instructor and in a lab notebook

17
Outlines

❑ Lab Safety Rules

18
Lab Safety Rules

Remember…
Safety
First, Last, and Always

19
Lab Safety Rules

Accidents
When? Where? What? How?

20
Lab Safety Rules

1. Ethylene glycol

Toxicity
2. Dioxin
3. Batrachotoxin
4. Potassium cyanide
5. Thioacetone Almost organic!!!
6. Dimethyl mercury
7. Fluoroantimonic acid
8. Azidoazide azide
9. Chlorine trifluoride
10. Dimethyl cadmium

21 https://owlcation.com/stem/The-10-Most-Dangerous-Chemicals-Known-to-Man
Lab Safety Rules – Pictographs

22
Lab Safety Rules – Pictographs

23
Lab Safety Rules – Pictographs

24
Lab Safety Rules – Organic synthesis lab

We have all in an organic synthesis lab   

25
Lab Safety Rules
1. Mandatory protective equipment

(used if necessary, available in lab)

26
Lab Safety Rules
1. Mandatory protective equipment

Wear safety glasses at all times in lab!!!

27
Lab Safety Rules
1. Mandatory protective equipment

28
 Lab Safety Rules
1. Mandatory protective equipment

No barefoot; No open-toe shoes; No holed shoes; No flip flop; No pumps

29
Lab Safety Rules
1. Mandatory protective equipment

 No short-sleeve lab coat

 No short, no skirt, no baggy

30
Lab Safety Rules
1. Mandatory protective equipment

☺ Tied-back long hair

 No loose hair

☺ Suitable gloves

31
Lab Safety Rules
1. Mandatory protective equipment

32
Lab Safety Rules
2. Ensure good health conditions

▪ Not healthy
▪ Open wounds
▪ In pregnancy Stop the lab course immediately!!!
▪ Prepare for pregnancy
▪ Doubt about pregnancy

33
Lab Safety Rules
3. Never eat, drink, smoke in lab

…and keep your hands away from your face and body

34
Lab Safety Rules
4. Never work alone

35
 Lab Safety Rules
5. Always be well-prepared and careful
• Read the manual and take notes before the lab
• Understand what you are doing in the lab and the possible hazards
• Carelessness → More accidents
• No fooling around, no playing around

36
Lab Safety Rules
6. Always follow your instructor’s directions

• Do not carry out a new/unknown operation until guided

• In doubt → Ask your instructor, Accidents, problems → Tell your instructor

• Always be responsible and respectful to each other Do not use

a beaker
• Do not touch equipment or chemicals
without permission

37
Lab Safety Rules
7. Know location and operation of safety equipment
✓ Fire extinguisher, fire alarm
✓ Eye wash, shower
✓ First aid kit
✓ Broken glass container, liquid/solid waste container
✓ Mop, broom, dustpan

38
 Lab Safety Rules
8. Working with chemicals

➢ Check chemical labels 2 times before taking

Or
➢ Know all information about chemicals (MSDS) before
using them (toxicity, flammability, volatility…) ???
➢ Never mix chemical unless told to do so
➢ Never transfer used chemicals back into the stock bottle
➢ Never taste any chemical
Or
???

39
 Lab Safety Rules
8. Working with chemicals

➢ Wash hands with soap after using chemicals

➢ Ask your instructor to dispose of any chemical/sample
➢ Store your product at a right place (ask your instructor)
➢ Provide info for all samples (label with Group No., Class)

40
 Lab Safety Rules
9. Working with electrical sources
➢ Be sure your hands and the area are dry before using electrical equipment
➢ Never put anything into electrical outlets
➢ Unplug all electrical equipment after the lab
➢ Keep chemicals away from electrical outlets

41
Lab Safety Rules
10. Working with heat sources

✓ Keep flammables (liquid, solid, gas) away from flame

✓ Use a water bath to heat flammable solvents

Heat solvent

Heat water
42
Lab Safety Rules
11. Working with glassware

✓ Never use glasswares for food or drink

✓ Do not change glassware temperature suddenly (heating, cooling)
✓ Check glassware carefully before using them
✓ Do not use glassware when working with HF, hot H3PO4, or strong hot alkalis
✓ Do not use excessive force to tighten glassware to clamps.
✓ Check all glassware for wetness, cracks and contamination before use.
✓ Never heat sealed or stoppered glassware.
✓ Never stopper or seal glasswares containing any hot volatile compound or any mixture
that will release gases
✓ Use pressure-assistant glasswares for vacuum and high-pressure applications.
✓ Never use a thermometer as a stirring rod

43
Lab Safety Rules
12. Security issues
 Do not allow unauthorized persons to enter the lab
 Look after property of all members (laptop, bag, wallet…) with the utmost care
 Check in/out with your instructor’s permission
 Close the door before leaving the lab if you are the last person

44
Lab Safety Rules

45
First Aid
A set of guidelines which can reduce the damages caused by exposure to
chemicals or injury before expert medical help can be provided

 First aid kit

 Contact information

 Guidelines for first aid providers

 Specific first aid tips

46
 First Aid
First aid kit

✓ Essential medicines, antiseptic

lotions, creams, bandages….
✓ Maintain a list of the contents
✓ Discard the expired medicines
✓ Replacement with fresh stocks

47
First Aid
Contact information
✓ Names and contact details of employees with first aid training certificates
✓ List of blood groups of all lab employees
✓ Names of employees with detailed specific allergies
✓ Telephone numbers of hospitals
✓ Emergency contact number for ambulance, fire service, and police

48
First Aid
Guidelines for first aid providers
✓ Maintain calm and evacuate the area in case there is danger.
✓ Start remedial action to save time before expert medical help can be provided.
✓ Do not attempt to move around the victim unless he/she is exposed to smoke, fire,
hazardous chemicals or vapors.
✓ Ensure that the victim is breathing. If breathing stops, try artificial respiration.
✓ Do not try to remove deeply embedded metal or glass shreds. Bandage the wounds to
control bleeding till medical help arrives.
✓ Intense bleeding can be stopped by pressing the wound with your thumb
✓ In case the victim has fainted turn him/her on the side with the face tilted towards the
floor to prevent choking by the tongue.

49
First Aid – Specific first aid tips
Skin thermal burn - very important!!!

50
 First Aid – Specific first aid tips
Skin chemical burn - very important!!!
1. Hold the affected skin under a stream of running water
for at least 10 – 15 min.
2. Keep the wound open
3. Do not apply any ointment/ cream/iodine/object until
expert medical help can be provided
4. Do not apply strong acids or bases to neutralize the
corrosive liquid on the skin
• Strong acid burns: after washing with water, rinse with dilute ammonia (1–2%) or
sodium bicarbonate (2–3%) solution

• Strong base burns: after washing with water, use a 1% acetic acid solution
51
 First Aid – Specific first aid tips
Chemical eye injury - very important!!!
1. Immediately wash the eyes with water using an eye fountain or eye wash bottle
2. Also flush your eye under a running faucet, kitchen sink sprayer, or shower
3. Move your eye in all directions so that all areas of your eye are rinsed
4. Pull the lower and upper eyelid forward so that any liquid chemical is rinsed away
5. Keep flushing the eye for at least 30 minutes or longer
6. Do not bandage or put any pressure on the eye
7. Immediately transport the injured person to a closest hospital
8. Never apply any chemical to the injured eyes until expert medical help can be provided
Watch the clip:
www.youtube.com/watch?v=NvLo7TGmDmc
(Obligatory for the final exam and for your eye
safety, Engsub is available)
52
First Aid – Specific first aid tips
Poisons

1. Oral poisoning: dilute the stomach contents by drinking a large amount of

water or milk → immediately transport the victim to a medical center
2. Gas poisoning: transfer the victim into the fresh air immediately → If
breathing is stopped or irregular, give artificial respiration → call for an
ambulance oxygen cylinder for taking the victim to the hospital.

53
First Aid – Specific first aid tips

Cuts and wounds

54
First Aid – Specific first aid tips

Cuts and wounds

Small cuts

55
First Aid – Specific first aid tips
Cuts and wounds
Serious wounds
1. Stop bleeding by covering the wound
with clean cloth or sterile gauze and
applying direct pressure.
2. Transport the victim to a hospital
immediately

56
 First Aid – Specific first aid tips
Electric shock

1. Turn off the current at the source.

2. Remove wire with insulator or rubber gloves.
3. Inform your instructor immediately.

57
First Aid – Specific first aid tips
Chemical spills
1. Be calm and responsible
2. Inform everyone immediately
3. Choose and use the most suitable equipment to clean up spills

58
First Aid – Specific first aid tips
Mercury spills

59
 First Aid – Specific first aid tips
Mercury spills

1. Hg is harmful to open wound, breathing and circulatory systems

2. But Hg absorption through skin and digestive system is difficult
3. And vapor pressure of Hg is low (0.00243 atm at 25 oC, compared
to 0.0313 atm of water)
4. In general, elemental Hg has low toxicity compared to organic
mercury compounds (i.e., dimethylmercury)

60
 First Aid – Specific first aid tips
Mercury spills
1. Never use a vacuum cleaner/mop/broom to clean up mercury. It will break the
spills into smaller droplets and spread them into the air and increase exposure.
2. Never pour mercury down a drain.
3. Never use a washer or dryer to clean clothing contaminated with mercury

61
First Aid – Specific first aid tips
Mercury spills

1. Put on gloves. Pick up broken glass pieces with care. Put them all in a bag.
2. Locate visible mercury beads. Use a dropper to collect or draw up them.
Alternatively, use two pieces of cardboard paper to collect them onto a paper
towel or into a bag.
3. Take a flashlight, hold it at a low angle close to the floor in a darkened room and
look for small mercury beads trapped in cracks.
4. Put all mercury and items used to pick up mercury in a trash bag
5. Seal all bags and put them in a secure place until they can be disposed of safely.

62
First Aid – Specific first aid tips
Mercury spills

✓ It is OPTIONAL to sprinkle sulfur powder over the

contaminated area and rub it gently all over the surface and
into the cracks with a paper towel. Sulfur can bind or cover the
mercury so that it can be easily removed and suppresses the
vapor of missing mercury.
✓ Use a paper towel dampened with water to clean up the sulfur
and mercury.
✓ Place the used paper towels in a plastic bag.

63
Outlines

❑ Apparatus

64
Apparatus

Clamp holder

Extension clamp

Clamp stand

Ring support

65
Apparatus

66
Apparatus

Vacuum filtration

67
Apparatus

Gravity filtration Hot gravity filtration

68
Apparatus

69
Apparatus

70
Apparatus
Condensers

Air condenser Liebig condenser Allihn condenser Graham condenser Coil condenser
(Straight condenser) (Bulb condenser)

71
 Apparatus
Temperature-controlled Reflux reaction
reaction apparatus apparatus

72
Outlines

❑ Basic techniques

73
 Basic Techniques – Washing and extracting

Wash vegetables… …then prepare soup

Both need water

and vegetables

This is a wash This is an extraction

To remove unwanted dirt To extract essences
with water into water
You discard water containing dirt You enjoy water containing essences

74
 Basic Techniques – Washing and extracting

to obtain expected
Extracting compounds from a to remove impurities
mixture/a matrix from expected Washing
compounds

Almost the same operation

but very different purposes

75
 Basic Techniques – Extracting

1. Solid-liquid process: dissolving some

components of a solid directly into the solvent
(tea/coffee making, extraction of essential oil from
plants)

2. Liquid-liquid process: pulling some components

from solvent A to solvent B (extracting morphine
from an aqueous solution into EtOAc)

76
 Basic Techniques – Solid-liquid extracting
Extract desired components from a solid material into a liquid solvent

✓ Smaller size of solid materials

✓ Good solubility of the expected compound in solvents
✓ Selectively dissolving the expected compound

77
 Basic Techniques – Liquid-liquid extracting
Extract desired components from solvent A to solvent B

✓ Based on relative solubilities of a compound in two different immiscible

liquids, typically water (polar) and an organic solvent (non-polar)
✓ The solvent enriched with solute(s): the extract
✓ The feed solution depleted of solute(s): the raffinate
✓ The larger the distribution coefficient (Kd = CB/CA), the more efficient the
extraction is
✓ Multiple extraction is always more efficient than single extraction even
with the same total solvent volume

78
 Basic Techniques – Liquid-liquid extracting
Extract desired components from solvent A to solvent B

For example: find a solvent to extract organic compound X from water

→ immiscible with water
→ well dissolve X, unreactive with X
→ low boiling point
→ cheap, non-toxic (optional)

79
 Basic Techniques – Liquid-liquid extracting
Extract desired components from solvent A to solvent B

For example: extraction of hyoscyamine from water into diethyl ether

80
 Basic Techniques – Washing

➢ Wash strong acids (HCl, H2SO4…) with Na2CO3aq (10%), NaHCO3aq, or water
➢ Wash weak organic acids (RCOOH) with Na2CO3aq (10%) or NaHCO3aq
➢ Wash very weak organic acids (phenols) with NaOHaq (5-10%)
➢ Wash strong inorganic bases (NaOH, KOH…) with water
➢ Wash organic bases (aniline, trimethylamine…) with HClaq (5-10%)
➢ Wash neutral compounds with immiscible solvents

81
 Basic Techniques – Washing and extracting
Procedure with a separating funnel
(Read p.11&12 of the student manual, very important!!!)

82
 Basic Techniques – Heating
Heat source Useful range (oC)

Steam bath 25 – 80

Water bath 0 – 70

Silicone oil bath 25 – 230 Electric hot plate

Magnetic hot-plate stirrer
Glycerol bath 25 – 200

Mineral oil bath 25 – 200

Sand bath 25 – 500

Spirit burner
(naked flame)
Electric heating mantle Sand bath on a heating plate

83
 Basic Techniques – Controlled boiling
Boiling stones (boiling chips)

➢ Small pieces of inert porous materials (silicon carbide, glass, carbon,

calcium sulfate, calcium carbonate, polytetrafluoroethylene) added to a
solution/solvent to control boiling:

• Act as nucleation for formation of solvent bubbles.

• Help the liquid boil smoothly without becoming superheated or

bumping

• Improve mass and heat transfer

➢ Used in distillation and boiling liquids (solvents, reaction mixture)

84
 Basic Techniques – Controlled boiling
Boiling stones (boiling chips)
➢ Never add boiling stones to a liquid that is boiling or near its boiling
➢ Never use boiling stones for non-boiling ones
➢ Do not reuse boiling stones without activation
➢ Might be reactive with concentrated solutions of acids or bases
➢ Alternatively, boiling sticks (wood splints) and stirring bar (always used with a magnetic
stirrer) are used to control boiling

Controlled boiling using a boiling stone a boiling stick a stir bar

85
 Basic Techniques – Cooling
Cooling is necessary for crystallization, low-temperature reaction, absorption of heat from
an exothermic reaction or reducing vaporization.
In lab, a cooling bath used to maintain low temperatures (13 °C → -196 °C) contains cooling
agents/mixtures such as:
• Water bath: room temperature
• Ice bath: 0 oC
• Crushed ice + sodium chloride (3:1 by weight): -20 oC
• Crushed ice + calcium chloride (4:5 by weight): -50 oC
• Dry ice (solid CO2) + liquid acetone or isopropanol: -78 oC

86
 Basic Techniques – Drying a liquid
Drying agents (desiccants) are usually anhydrous salts that combine with the water in the
product and hold it as water of crystallization.

After drying, simple decantation or gravity filtration can be performed to remove the
hydrated agent from the product.

87
 Basic Techniques – Drying a liquid
• Anhydrous calcium chloride: do not apply to dry acid, alcohol, phenol, amine, amino acid,
amide, ketone, ester and aldehyde
• Anhydrous sodium sulfate: Na2SO4 loses water at above 32 °C
• Anhydrous magnesium sulfate: one of the best drying agent
• Anhydrous sodium carbonate and potassium carbonate: do not apply to dry acidic
products

Organic compounds Drying agents

R-X (X=Cl, Br, I) CaCl2, CaSO4, P2O5, MgSO4
Alcohol CaSO4, MgSO4, K2CO3, CaO
Ether, saturated hydrocarbon, arenes CaCl2, CaSO4, P2O5
Aldehyde CaSO4, MgSO4, Na2SO4
Ketone CaSO4, MgSO4, Na2SO4
Organic acid CaSO4, MgSO4, Na2SO4
Amine KOH, NaOH, K2CO3, CaO
88
 Basic Techniques – Drying a solid
Solids can be dried in air or in an oven, under atmosphere or vacuum

Desiccator for gently drying samples and storing dried ones

89
 Basic Techniques – Distillation

Separation a mixture of liquids based on difference in their boiling points:

1/ heating a liquid mixture to its boiling point
2/ transferring the vapor to a different portion of the apparatus
3/ condensing the vapor
4/ collecting the condensate in another container
After a distillation process,
- residue in the distilling flask: enriched with non-volatile/less-volatile components
due to their higher bp
- distillate (condensate): enriched with more-volatile ones due to their lower bp

90
 Basic Techniques – Distillation

91
 Basic Techniques – Distillation
A successful distillation depends on:
✓ Difference in the boiling points of the components in the mixture
✓ Difference in their vapor pressures
✓ Distillation rate
✓ Thermometer position
✓ Type of apparatus
✓ Experimental skill
Common distillation methods in lab:
1/ Simple distillation
2/ Vacuum distillation
3/ Fractional distillation
4/ Steam distillation
92
 Basic Techniques – Simple Distillation

Simple distillation involves a single liquid-vapor equilibration (one theoretical

plate) to separate the components boiling below 150 oC (at 1 atm) from:
✓ Non-volatile impurities or solid impurities
✓ Another component with a boiling point that differs by at least 25 oC
In simple distillation, all components in the initial mixture must be miscible
and stable at the boiling points at 1 atm

Procedure and notes for simple distillation: p.18-19-20 of the student manual
(very important for your “ethyl acetate” synthesis, the final test and
even your future work !!!)

93
 Basic Techniques – Simple Distillation

94
 Basic Techniques – Vacuum Distillation
✓ Vacuum distillation at a reduced pressure is used to distill compounds that have a
very high boiling point, i.e. above 150 oC, or might be decomposed or be more
reactive at their boiling point at 1 atm.
✓ To perform a vacuum distillation, all components in the initial mixture must be
miscible and have a boiling point difference of at least 25 oC

95
 Basic Techniques – Fractional Distillation
Fractional distillation is used to separate miscible liquids with similar
boiling points (less than 25 °C), including repeated distillations and
condensations, into component parts called fractions

96
 Basic Techniques – Steam Distillation

A mixture of bromobenzene (bp 156 °C) and water (100 °C)

At 95 oC, Ptotal = pwater + pbromobenzene = 640 mm Hg + 120 mm Hg = 760 mm Hg

→ boiling begins

97
 Basic Techniques – Steam Distillation

✓ Boiling point much higher 100 oC but sensitive to heat

✓ Insoluble or slightly soluble in water Apply steam distillation

to separate this component
✓ Unreactive with water from a matrix or a mixture
✓ Have a high vapor pressure at 100 oC and 1 atm

By adding water or steam, the boiling points of the resulting mixture are depressed,
allowing them to evaporate at temperatures lower than 100 oC.

For example, a mixture of bromobenzene (bp 156 °C) and water (bp 100 °C)

At 95 oC, Ptotal = pwater + pbromobenzene = 640 mm Hg + 120 mm Hg = 760 mm Hg

→ boiling begins at 95 oC

98
 Basic Techniques – External Steam Distillation

99 http://ochemlabtechniques.blogspot.com/p/how-steam-distillation-works.html
 Basic Techniques – External Steam Distillation

100 https://www.doterra.com/US/en/blog/science-research-news-steam-distillation
 Basic Techniques – Internal Steam Distillation

Water and
material

Heat source

101 https://chemdictionary.org/steam-distillation/
 Basic Techniques – Azeotropic Mixture
A mixture of two or more liquids whose proportions cannot be changed by
simple distillation or extraction, e.g. an azeotropic mixture of 95.63 wt.% of EtOH
(bp 78.4 °C) and 4.37 wt.% of water (bp 100 °C) boils at 78.2 °C

azeotropic mixture
102
 Basic Techniques – Azeotropic Mixture

To break an azeotrope (important!!!)

✓ Addition of an additional agent for azeotropic distillation
✓ Distillation with changed pressure
✓ Selective absorption using molecular sieves
✓ Chemical separation by a reaction selective only with one of components
(e.g., CaO to remove water from ethanol, but Na2SO4 and MgSO4 → NO!!!)
✓ Membrane methods

103
 Basic Techniques – Recrystallization

To purify impure solid products in a solvent or a mixture of solvents

Recrystallization efficiency depends on
✓ Product purity
✓ Solvent properties
✓ Solubility of the product and impurities in the used solvent
✓ Temperature range
✓ Experimental skill

Recrystallization of benzoic acid in water by HCMUT students

104
 Basic Techniques – Finding Solvent for Recrystallization

An ideal solvent for recrystallization must satisfy the following properties:

✓ Well dissolve the substance at the boiling point of the solvent
✓ Poorly dissolve or cannot dissolve the substance at lower temperatures
✓ Unreactive with the substance
✓ Have a boiling point at least 10-15 oC lower the melting point of the substance
✓ Volatile, inexpensive and have a low toxicity (optional)

Very important!!!

105
 Basic Techniques – Finding Solvent for Recrystallization

For impurities in the substance, recrystallization will be ideal if

o Impurities are insoluble in the chosen solvent at high temperature
or
o Impurities are very soluble in the chosen solvent at low temperatures
or
o The solubilities of the substance and impurities in the chosen solvent are
similar and the quantity of impurities is small

106
 Basic Techniques – Finding Solvent for Recrystallization
✓ Find a right solvent usually requires prediction, experience and trial
✓ Generally, a compound might be soluble in solvents with similar polarity
✓ Increasing polarity: hexane < cyclohexane < tetrachloromethane < toluene < benzene <
diethyl ether < dichloromethane < chloroform < ethyl acetate < acetone < ethanol <
methanol < water
✓ Experimental procedure to select a solvent for recrystallization of an impure
compound: see p.24&25 of The Student Manual

107
 Basic Techniques – Finding Solvent for Recrystallization

No single solvent is satisfied → think about using two or more solvents

✓ Soluble in a solvent
✓ Slightly soluble or insoluble in another
✓ These two solvent are miscible

108
 Basic Techniques – Recrystallization Procedure
Typical procedure with a single solvent

1. Dissolve with a minimal amount of boiling solvent

2. Slowly cool down to RT then to lower temp
3. Vacuum filtrate

→ Practice: synthesis of DBA

109
 Basic Techniques – Recrystallization Procedure
Other optional steps with a single solvent

➢ Insoluble solids → hot filtration

➢ Unexpected color → decolorization and hot filtration
➢ More details at p.26-27-28 of The Student Manual
➢ Practice: recrystallization of benzoic acid

110
 Basic Techniques – Recrystallization Procedure
Typical procedure with a mixed-solvent system
(solvent A: soluble, solvent B: very slightly soluble)
1. Dissolve the compound in the minimal amount of hot solvent A
2. Add hot solvent B until the solution turns cloudy
3. Make sure that this cloudiness is stable on a hot plate or in a hot water bath
4. Add some drops of hot solvent A to make the solution transparent again
5. Slowly cool, and collect the crystals on a Buchner funnel
6. Wash the crystals with cold solvent B

→ Practice: synthesis of aspirin

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Outlines

❑ LAB REPORT

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 Lab Report

Ask your instructor ☺ ☺ ☺

➢ Lab notebook for all hand-written reports (at least 96 pages)

Or

➢ Separate hand-filled lab report forms

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 Lab Report Form

MUST BE HAND-FILLED!!!
1. Objective

2. Reactions, side reactions and mechanism

3. Properties of used chemicals

4. Procedure flowchart

5. Apparatus

6. Questions and answers (finished after the lab)

7. Yield calculation (finished after the lab)

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 Lab Notebook

MUST BE HAND-WRITTEN!!!

1. Objective

2. Reactions, side reactions and mechanism

3. Properties of used chemicals

4. Procedure flowchart

5. Apparatus

6. Questions and answers (finished after the lab)

7. Yield calculation (finished after the lab)

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 Procedure Flowchart

Reactant 1 Reactant 2 Catalyst Solvent Separate ovals: material

Rectangle: main operation Conditions of operation: reflux, stirring,

For example: reaction, esterification, Reaction
time, temp., pressure, pH
washing, extraction, distillation,
mixing, dissolving, cooling, drying…
No stirring here!!!
Raw product Octagon: Raw product/Intermediate
… purification

Product Diamond: Final product

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 Procedure Flowchart

Extraction Distillation

Layer containing the product here!!! Temp. range to collect product here!!!
(Upper layer or lower layer) (e.g., < 90 oC)
Next step Next step

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Have fun
and
Good luck!!!