Ho Chi Minh University of Technology

Vietnam National University Ho Chi Minh City

FRACTIONAL DISTILLATION
EUCALYPTOL
From Eucalyptus globulus
Instructor: Dr. Xuan - Tien Le
Group: 2

Ho Chi Minh City, 26th May 2021

 MEMBERS OF
GROUP 2
FULL NAME Student ID

1 Tran The Danh 1810067

2 Nguyen Chi An 1810003

3 Nguyen Truong Nhu Hao 1810133

4 Lam Bao Long 1810291

5 Ong Thi Ngoc Khanh 1810230

TABLE OF 01 INTRODUCTION
FRACTIONAL
CONTENT 02 DISTILLATION
S EUCALYPTOL
03 PRODUCTION
 01
INTRODUCTIO
N
Presented by Nguyen Chi An
Eucalyptus
globulus L.
(Sounthern Blue gum)
 WHERE DO THEY LIVE?

AUSTRAL
IA

AMERICA
(California, Hawaii)

TASMANI
A
 TREE
DESCRIPTION
- Large
- Smooth bark
- Pale color
- Typically 30 – 45m
E. globulus LEAVES
- Young leaves: arranged in
opposite pairs, sessile, egg-
shaped, up to 150mm long
- Adult leaves: arranged alternately,
dark green, lance-shaped, up to
300mm long
 DESCRIPTION
FLOWERS &
FRUITS
- Flowers: always white
- Fruits: woody conical
capsule with valves
FLOWER BUDS E. globulus
- Arranged in group or 3 – 6
in leaf axils
- Usually sessille
- Mature buds: conical-
shaped, green, has a central
knob
Eucalyptus
essential oil
&
Eucalyptol
 EUCALYPTUS ESSENTIAL
OIL

Essential oil content in leaves: ~ 1-3%

Major constituents: Eucalyptol (45 – 85%) & -

Pinene (1 – 25%)

Constituent content change by environmental,

age, growth regulator,…
EUCALYPTUS ESSENTIAL
OIL
EUCALYPTUS ESSENTIAL
OIL
EUCALYPTUS ESSENTIAL
OIL
 FORMULA
EUCALYPTOL
C10H18O

M=154.249g/mol PHYSICAL
1,8 – cineole PROPERTIES
PHYSICAL - Density: 0.9225g/cm3
DESCRIPTION - Melting point: 1.5oC
- Colorless liquid with
- Boiling point: 176oC
a camphor-like odor
- Insoluble in water
- Spicy cooling taste

IUPAC NAME
1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane
 USES

EUCALYPTOL
MARKET PRICE
 02
FRACTIONAL
DISTILLATION
Presented by Nguyen Truong Nhu Hao
 WHY DO WE USE FRACTIONAL
DISTILLATION?
ESSIENTIAL OIL
CRUDE OIL

CONTAMINA
OBJECTIONA DARK COLOR
TED
BLE ODOR
decomposition of
certain aldehydes or presence of metals,
complex plant
sulfur compounds fine plant dust
substances
 A technique is used
to isolate or purify
various components Differences in the
present in essential FRACTIONA volatility of
oils. L compounds.
Based on

DISTILLATIO The pressure and

The most common method
due to the operational
N temperature of the
distillation process.
simplicity and low costs.
FRACTIONAL
DISTILLATION
SYSTEM IN
LABORATORY
● A temperature gradient is form in
the column : coolest at the top and
hottest at the bottom.

● As the mixed vapor ascends the

temperature gradient, some of the
vapor condenses and returns to the
distilling flask.
 TYPE OF COLUMN

a. Vigreux b. Steel Wool c. Glass Beads

INDUSTRIAL FRACTIONAL DISTILLATION
Industrial fractional distillation

● Molecules start to rise up the

column, making their way
through bubble caps in each
tray.

● The bubble caps slow down the

rate of the rising vapor and
eventually the vapor gets too
cool, condenses and are
collected as liquid in the trays.
 Essential oils are a blend of terpenes and other
volatile compounds.

presence of
high temperature Most terpenes are thermally unsteady,
light or
decomposing, or oxidizing.
oxygene

VACUUM FRACTIONAL
DISTILLATION

Decrease the volatile Separate the hydrocarbon terpenes

mixture’s temperature of from the terpenes with other chemical
vaporization. functions.
 at ion
i still n
D lum
Co

FRACTIONA
L
Energy input
DISTILLATIO
N
Va
Pre cuum
ss u
re
 03
EUCALYPTOL
PRODUCTION
 Raw
materials
STEP
Crude oil
1

Fractional
distillation

STEP
Eucalyptus 2
By product
leaf oil

Purification Freezing

STEP
High-Eucalyptol High-Eucalyptol
3
oil oil
 STEP 1
Pretreatment &
Steam Distillation
Presented by Lam Bao Long
PROCEDURE
Raw materials

1 – 1.5h
Steam 2-2.5h
Distillation 0.5h

Condense

Separation

Crude oil
 RAW MATERIALS

Leaves of Eucalyptus globulus

Leaves after treatment
(from China)
 STEAM DISTILLATION

DIRECT
DIRECT INDIRECT
INDIRECT

Steam from separate boiler

Mixture of plant materials and
carried away volatile organic
water is boiled directly.
compounds.
STEAM DISTILLATION SYSTEM WITH
SEPARATE BOILER
STEAM DISTILLATION MODEL
 STEP 2
Fractional
Distillation
Presented by Tran The Danh
 EUCALYPTUS CRUDE OIL COMPONENTS

45% 18% 10%

1,8 – CINEOLE LIMONENE P-CYMENE

176 – 177oC 176oC 177oC

9% 4% 14%

-TERPINENE -PINENE OTHER

183oC 156oC
 BATCH DISTILLATION

Beside 80%-eucalyptol-oil, produce byproduct

with eucalyptol content ~30% - 70%

Non-specified product, low price, limited

outlet

Unstable product quality

 BATCH DISTILLATION
Need to empty residue after every batch & feed
again

High labor & energy consumption

Low effective production time

Low production efficiency

Using in small-scale production

 CONTINUOUS
BATCH DISTILLATION
DISTILLATION
 IMPROVES…
10 times
Productivity

+20%
Effective production time

-15%
Energy consumption

+25%
Yield
…when compare with batch distillation
 OPERATING CONDITIONS

MASS FLOW TEMPERATURE PRESSURE

400 – 450 kg/h 3 – 15KPa

110 – 160oC
(Crude oil) (vacuum)

EUCALYPTOL NUMBER OF
REFLUX RATIO
CONTENT FRACTIONS
45 – 62.5wt%
3 10 - 15
(Crude oil)

EUCALYPTOL Top cut: <11wt%

CONTENT STANDARD Eucalyptol-rich cut: >80wt%
STEPS TO SELECT OPERATING
CONDITION
OPERATE 3 – 15KPa
VACUUM SYSTEM

FEED SPECIFIED
AMOUNT OF CRUDE 110 – 160oC
OIL

OPERATE R=10 – 15
REFLUX SYSTEM 1-2h

ANALYSE SAMPLE
 STEPS TO SELECT OPERATING
CONDITION
ANALYSE SAMPLE

COMPAR
E WITH
STANDA
RD

OPERATE ADJUST
CONTINOUS FEEDING OPERATING
SYSTEM CONDITIONS
 RESULTS & DISCUSSION

Feed
Mass Top cut Eucalyptol-rich Bottom cut
Exp eucalyptol
flow (1st fraction) cut (2nd fraction) (3rd fraction)
content
1 450kg/h 62.5% 62kg/h (3%) 345kg/h (80.5%) 43kg/h (5%)
2 420kg/h 62.5% 90kg/h (4%) 300kg/h (85.5%) 30kg/h (6%)
3 450kg/h 58% 100kg/h (3%) 315kg/h (81.5%) 35kg/h (5%)
4 420kg/h 58% 125kg/h (5%) 255kg/h (92%) 40kg/h (4%)
5 430kg/h 45% 200kg/h (11%) 200kg/h (82%) 30kg/h (10%)
6 400kg/h 53% 130kg/h (10%) 238kg/h (81%) 32kg/h (9%)
7 400kg/h 58% 100kg/h (1%) 285kg/h (80.5%) 15kg/h (6%)
 STEP 3
Further
purification
Presented by Ong Thi Ngoc Khanh
MARKET ANALYSIS
 METHODS OF PURIFICATION

>99wt% 85.1wt%

TAKE STRONG ACID

REFRIGERATED
AS EXTRACTION
CENTRIFUGATION
AGENT
BYPRODUCT PURIFICATION PROCEDURE
Pre-treated oil

Phenol (ratio 0,3:1) Stop when

Vacumn Distillation - Top scope temperature: 45-80oC
- Removing time: 1-6h
Kettle base solution
Access when:
Water Atmospheric - Top scope temperature: 90-100oC
Distillation - Removing time: 1-6h

Aezotrope mixture
Vibrating layer and
drying

High-
Eucalyptol oil
 RESULTS & DISCUSSION

exp1 exp2 exp3 exp4

Initial content 37% 45% 50% 32%
Amount of phenol 56.28% 80% 100% 50%
Pressure 2.4KPa 3.2KPa 4.0KPa 3.0KPa
Water ratio 1:1 1.05:1 1.74:1 1.07:1
Purity 99.2% 99.2% 99.9% 98.9%
Yield 70.5% 75% 78% 71%
 PROS & CONS

PRO
CONS
S
 High purity and
 recovery rate  Consume large amount
 Stable process of solvent
 Large-scale production  High operating cost
potential
 ANOTHER METHOD OF FRACTIONAL
DISTILLATION

Pre-treated oil

Top product
C2 – C4 alcohol Vacumn Distillation -Pinene

High-
Eucalyptol oil
 RESULTS & DISCUSSION

exp1 exp2 exp3

Initial content 63% 60% 58%
Amount of ethanol 6% 8% 10%
Pressure 1KPa 2KPa 4KPa
R1 and R2 10-16 12-18 15-20
Purity 96.5% 93.12% 94.34%
Yield 75.35% 76.75% 75.85%
 PROS & CONS

PROS CONS
 Simple technology
and stable process  Batch distillation
 High purity high
yield
 Flexible operation
Thanks for
listening! Do you have any
questions?
danh.tran_2108@hcmut.edu.vn

https://www.facebook.com/danh.tran2108/

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