Group 33

Production of Synthetic
Vanillin from Clove Leaf Oil
Ahlan Fauzi. Khusnul Layli Putri. Muhammad Akbar. Reysa Anggraini. Sauria Karina
1 INTRODUCTION
Vanillin is one of the most popular
flavouring agents in food industry
and its wide range of application
also spreads to the fields of
perfumery and pharmaceutical
intermediates.

“
Vanillin Market Segmentation

Ph.D. Dissertation of Biological and Chemical Engineering in Universidade do Porto

Natural Vanillin from
vanilla beans
takes a lot of time, labor and
land leading to less sustainable
product with high cost.
Alternative ideas of vanillin
manufacturing

CLOVE
GUAIACOL LEAF OIL

LIGNIN
 So far, Indonesia is known as the
world's largest producer of clove oil
which controls 63% of the world
market (Rizal and Djazuli, 2006)

“
Asia Pacific (39.7%) of the total revenue in 2016
followed by Europe (27.33% )

(Grand View Research, 2017).

Global Vanillin Demand
Year Demands (tons)
2016 14,264
2017 15,148.37
2018 16,087.57
2019 17,085
2020 18,144.27
2021 19,269.21
According to Grand Market
2022 20,463.90 Research 2017,
2023 21,732.66 global vanillin demand
2024 23,080.09 expected growth rate is 6.2%
2025 24,511.05 from 2016 to 2025
Global Vanillin Supply

Vanillin Industries Supply Ability

Simagchem corp. 5000 ton/year
Shanghai Fuxin Fine Chemical Co., Ltd. 360 ton/year
Guangzhou Yahe Food Ingredients Co., Ltd. 1100 ton/year

Shanghai Yancui Import and Export Co., Ltd. 3000 ton/year

Anhui Eastmark International Trading Co., Ltd. 10000 ton/year

A.M Food Chemical (Jinan) Co., Ltd. 1000 ton/year

950 tons/year
(2.88 tons/day)
Based on 5% market share target from global demand.
2 PLANT LOCATION
Jl. Raya Modern Industri, Barengkok, Kawasan Industri Cikande, Serang, Banten 42185
(coordinate: -6.1832544, 106.3171502).
 Plant Location Considerations

Raw Material Distribution Product Distribution Water Accesibility

Clove leaf oil
– PT Global Muda Tridharma, Tangerang
Additional material
– PT Asahimas Chemical, South Jakarta
◉ Near Jl. Tol Tangerang-Merak
◉ Near Pelabuhan Merak
◉ 75% of Indonesian food and
beverage industries
Process water is supplied by
PT Sarana Tirta Rejeki for the
whole Kawasan Industri
Cikande

Land Price and Local Min. Wage

◉ Started from Rp1,500,000.00/𝑚2 (lower
than other Jabodetabek)
◉ Minimum wages Rp3,542,713.5 (lower
than Bekasi and Karawang)
 PROCESS
3 SELECTION
 Clove Leaf Oil to Vanillin
General Process

Eugenol
Isomerization Oxidation Purification
Isolation
 Phenolic Compounds
(largest component).
Process Selection of Eugenol Clove Contains 80-85% Eugenol
Leaf Oil
Isolation Method
Non-Phenolic Compounds.

• Fractional distillation is also highly FD CE

Num. Criteria Percentage
efficient R S R S
• Chemical extraction have shorter time 1 Suitability for raw material 20% 3 0.6 5 1.0
reaction
2 Production Capacity 20% 5 1.0 4 0.8
• Fractional distillation is expensive;
3 Process Time 10% 3 0.3 5 0.5
large structures, heavy duty materials,
specialize machinery with staff to be 4 Human Skill Requirement 5% 1 0.05 4 0.2
fully trained 5 Installation 10% 2 0.2 4 0.4
• Dangerous for people because 6 Capital Investment &Ops. Cost 20% 2 0.4 3 0.6
potentially explosion 7 Environmental Risk 15% 1 0.15 4 0.6
Total 100% 2.7 4.1
Rank 2 1
 Catalyst Selection in Eugenol Isomerization
Several factors :
• the type of catalyst, solvent AB TM
Num. Criteria Percentage
• temperature R S R S
• molar ratio (catalyst concentration)
1 Reaction time 30% 3 0.9 4 1.2
• the presence of water
2 Reactant concentration 30% 2 0.6 4 1.2
3 Difficulty 15% 3 0.45 4 0.6
4 Phase 10% 2 0.2 4 0.4
Strong solutions of alkaline base at very high
temperatures (140-190oC) which are very long 5 Hazardous 15% 2 0.3 4 0.6
(5-7 hours) can result in overheating and Total 100% 2.45 4.0
decomposition
The advantages of metal catalyst: Rank 2 1
1. high eugenol conversion rates
2. the process is easier because there is no
thickening of the reactants during the
reaction
3. efficient because the amount of reactants
added is relatively small
4. low hazardous effluent after reaction
(Sharma et al., 2006).
 Oxidizer Selection in Isougenol Oxidation

Several factors : Num. Criteria Percentage

NB KMnO4 H2O2
1. the type of oxidizer, catalyst R S R S R S
2. temperature 1 Conversion 20% 3 0.6 2 0.4 4 0.8
3. oxidizer mole ratio with isoeugenol 2 Concentration 20% 2 0.4 3 0.6 3 0.6
4. reaction time 3 Purity 30% 3 0.9 2 0.6 3 0.9
4 Price 30% 3 0.9 2 0.6 1 0.3
o Nitrobenzene (130oC, 3 hours) produce Total 100% 2.8 2.2 2.6
53.8% (conventional), 86.10%
Rank 1 3 2
(microwaves)
o KMnO4 with18-crown ether-6 catalyst
produce 22.9%.
o H2O2 oxidizer with
methyltrioxorhenium (MTO) catalyst
produce 64-75% at lower temperature
“
(60OC), shorter time (2 hours). But
high prices of MTO and it availability.
 PROCESS
4 DESCRIPTION
Vanillin From Clove Oil Production Process

The plant runs in continuous mode

◉ Large production capacity:

977 tons/yr (>500 tons/yr ◉ The process takes
according to Walas (1988)) many procedures
(>20 unit operations)

◉ Reduces the
◉ High efficiency in
mass and heat
required volume of
transfer
reactors
 Sections of Vanillin Production
1

4
Eugenol
from Clove Eugenol Isoeugenol Vanillin
Oil Isolation Isomerisation Oxidation Purification
Vanillin From Clove Oil Production Process

Vanillin
Purification
Eugenol Isolation Section

Acid-base extraction
method

1. Salts formation
2. Excess clove oil
removal
3. Neutralization
4. Eugenol from by-
products
separation
 Eugenol Isolation Section
Continuous Stirred Tank Reactor (CSTR)
1. Salts Formation
◉ Salt is formed by the
reaction of NaOH 4% and
eugenol
◉ Oil and NaOH ratio is 1:5

Operation Data
Parameter Value
Temperature 45oC
Pressure 1 atm
Conversion 85%
Total Reaction Time 0.5 h
 Eugenol Isolation Section
Continuous Stirred Tank Reactor (CSTR)
1. Salts Formation Product Stream:

Mass Comp.
Feed Stream 1: Component
(%wt)
Mass Comp. Na- 16.25
Component
(%wt) eugenolat
Clove oil 100 Excess clove 8.14
oil
Feed Stream 2:
Sodium 0.47
Mass Comp. Hydroxide
Component
(%wt)
Water 75.13
Sodium 4%
Hydroxide
Water 96
 Eugenol Isolation Section
Top Product Stream:
2. Excess Clove Oil Removal
Density at Mass Comp.
◉ Employs a high rotational speed to separate Component
20oC (g/mL) (%wt)
components of different densities
Clove Oil 1.04 26.74
Feed Stream: Centrifuge Decanter
Water 0.99 73.26
Mass Comp.
Component
(%wt) Bottom Product Stream:

Na- 16.25 Density at Mass Comp.

eugenolat Component
20oC (g/mL) (%wt)
Excess clove 8.14 Na-Eugenolat 2.028 23.38
oil
Sodium 2.13 0.67
Sodium 0.47 Hydroxide
Hydroxide
Water 0.99 75.95
Water 75.13
 Eugenol Isolation Section

3. Neutralization
Continuous Stirred Tank
◉ Strong acid addition (HCl Reactor (CSTR) Operation Data
8%) to obtain eugenol from
Parameter Value
Na-eugenolat
Temperature 45oC
Pressure 1 atm
Conversion 90%
Total Reaction Time 0.5 h

Na-Eugenolat Eugenol
 Eugenol Isolation Section
3. Neutralization
Feed Stream 1: Continuous Stirred Tank Product Stream:
Reactor (CSTR)
Mass Comp. Mass Comp.
Component Component
(%wt) (%wt)
Na-Eugenolat 23.38 Eugenol 10.81
Sodium Hydroxide 0.67 Na-eugenolat 3.32
Sodium 4.41
Water 75.95 Chloride
Feed Stream 2: Sodium 0.16
Mass Comp. Hydroxide
Component (%wt) Water 81.30
HCl 8
Water 92
 Eugenol Isolation Section
Top Product Stream:
4. Eugenol from by-products separation Density at Mass Comp.
Component
20oC (g/mL) (%wt)
◉ Employs a high rotational
Eugenol 1.046 21.82
speed to separate
components of different Centrifuge Decanter Water 0.99 78.18
densities Bottom Product Stream:
Density at Mass Comp.
Component
20oC (g/mL) (%wt)
Na-Eugenolat 2.028 6.59
Sodium 2.13 0.32
Hydroxide
Sodium 2.16 8.74
Chloride
Water 0.99 84.36
 Eugenol Isomerisation
Section
◉ Employs the catalyst
of rhodium(III) chloride
dissolved in ethanolic
solution (99.9%).

Operation Data
Parameter Value
Temperature 150oC
Eugenol Isoeugenol
Pressure 1 atm
Rate constant 3,6087 h-1
Total Reaction Time 5h
 Eugenol Isomerisation
Section

Feed Stream 1: Top Product Stream:

Mass Comp. Mass Comp.

Component Component
(%wt) (%wt)
Eugenol 92.55 Water 92.55

Water 7.44 Ethanol 7.44

Feed Stream 2: Bottom Product Stream:

Mass Comp. Mass Comp.

Component Component
(%wt) (%wt)
Ethanol 92.99 Eugenol 0.007

Water 0.1 Isoeugenol 99.993

Isoeugenol Oxidation
Section

Procedures:

1. K-isoeugenolat
formation
2. Oxidation
3. Neutralization
 Isoeugenol Oxidation
Section
1. K-isoeugenolat Formation Continuous Stirred Tank
Reactor (CSTR)
Operation Data
Parameter Value
Temperature 36.43oC
Pressure 1 atm
Conversion 90%
Total Reaction Time 0.5 h
 Isoeugenol Oxidation
Section
1. K-isoeugenolat Formation Continuous Stirred Tank
Reactor (CSTR)
Feed Stream 1: Product Stream:

Mass Comp. Mass Comp.

Component Component
(%wt) (%wt)

Eugenol 0.007 Isoeugenol 5

Isoeugenol 99.993 K-eugenolat 0.004

Feed Stream 2: K-isoeugenolat 56.21

Mass Comp. KOH 21.86

Component
(%wt) Water 16.87
KOH 76

Water 24
 Isoeugenol Oxidation
Section Continuous Stirred Tank
Reactor (CSTR)
2. Oxidation
◉ The reaction proceeds with the Operation Data
present of nitrobenzene as Parameter Value
oxidator. DMSO acts as Temperature 130oC
solvent of nitrobenzene with
Pressure 1 atm
the ratio of 2:1
Rate constant 5.29 h-1
Total Reaction Time 3h

+
 Product Stream 1:

Mass Comp.
Isoeugenol Oxidation
Component
(%wt)

2. Oxidation
Section Continuous Stirred Tank
Acetaldehyde 25.73

Water 74.27
Feed Stream 1: Reactor (CSTR)
Mass Comp. Product Stream 2:
Component
(%wt)
Mass Comp.
Component
Isoeugenol 5.04 (%wt)
K-eugenolat 0.004 Azobenzene 12.62

K-isoeugenolat 56.21 DMSO 39.28

KOH 21.86 Isoeugenol 2.26

Water 16.87 K-eugenolat 0.002

Feed Stream 2: K-isoeugenolat 11.12

Mass Comp. K-vanilat 13.24
Component
(%wt)
KOH 9.80
DMSO 66.67
Nitrobenzene 11.67
Nitrobenzene 33.33
 Isoeugenol Oxidation
Section
3. Neutralization Continuous Stirred Tank
Reactor (CSTR)
◉ K-vanilat salt is reacted with Operation Data
HCl 25% to obtain vanillin Parameter Value
Temperature 36.43oC
Pressure 1 atm
Conversion 90%
Total Reaction Time 1h
 Product Stream:

Mass Comp.
Isoeugenol Oxidation Component
(%wt)

Section Azobenzene 9.20

DMSO 28.62
3. Neutralization Continuous Stirred Tank
Isoeugenol 1.65
Feed Stream 1: Reactor (CSTR)
HCl 0.95
Component Mass Comp. (%wt)
K-eugenolat 0.001
Azobenzene 12.62
K-isoeugenolat 8.10
DMSO 39.28
K-vanilat 0.96
Isoeugenol 2.26
KCl 14.22
K-eugenolat 0.002
Nitrobenzene 8.5
K-isoeugenolat 11.12
Vanillin 7.44
K-vanilat 13.24
Water 20.35
KOH 9.80 Feed Stream 2:
Nitrobenzene 11.67 Component Mass Comp. (%wt)
HCl 25
Water 75
 Vanillin Purification Section

Procedures:
1. Extraction
2. Sodium Bisulfite
Addition and
Neutralization
3. Re-extraction
4. Spray Drying
 Vanillin Purification Section

1. Extraction
◉ Diethylether is volatile
compound and has low boilling
◉ Diethylether acts as organic point (35oC)  separated with
solvent to extract vanillin from evaporation
dissolved mixture of oxidation
by-product
 Top Product
Vanillin Purification Section Mass Comp.
Component
1. Extraction (%wt)
Feed Stream 1:
Diethylether 9.20
Mass Comp.
Component Isoeugenol 28.62
(%wt)
Azobenzene 9.20 Vanillin 1.65
DMSO 28.62 Water 0.95
Isoeugenol 1.65
HCl 0.95
K-eugenolat 0.001
K-isoeugenolat 8.10
K-vanilat 0.96
KCl 14.22
Feed Stream 2:
Nitrobenzene 8.5
Mass Comp.
Component
Vanillin 7.44 (%wt)
Water 20.35 Diethylether 100
 Operation Data

Vanillin Purification Section Parameter Value

Temperature 30oC
Pressure 1 atm
2. Sodium Bisulfite Addition and
Conversion 100%
Neutralization
Total Reaction Time 1.5 h
◉ NaHSO3 extracts vanillin
dissolved in diethylether to
form vanillin-bisulfite

vanillin-bisulfite
 Product Stream
Mass Comp.
Vanillin Purification Section Component
(%wt)
Recovery with
evaporation and Diethylether 21.22
2. Sodium Bisulfite Addition and condensation Isoeugenol 3.22
Neutralization
NaHSO3 11.27
Feed Stream 1: Form as bottom
Vanillin-bisulfite 24.49
Mass Comp. product in
Component centrifuge Water 39.79
(%wt)
Diethylether 9.20
Isoeugenol 28.62
Vanillin 1.65
Water 0.95

Feed Stream 2:
Mass Comp.
Component
(%wt)
NaHSO3 100
 Operation Data

Vanillin Purification Section Parameter Value

Temperature 40oC
Pressure 1 atm
2. Sodium Bisulfite Addition and
Conversion 100%
Neutralization
Total Reaction Time 1.5 h
◉ Neutralization with 96% sulfuric acid to separate
vanillin from vanillin-bisulfite
Vanillin-bisulfite + H2SO4  Vanillin + Na2SO4 + SO2 + H2O
Bottom Product Stream
Mass Comp.
Component
(%wt)
NaHSO3 9.36
Sulfuric acid 11
Vanillin 43.45
Water 36.18
 Vanillin Purification Section

3. Re-extraction
◉ Re-extraction of vanillin with diethylether
◉ Followed by centrifugation to remove bottom
product, and evaporation to remove the solvent
Feed Stream
Mass Comp.
Component
(%wt)
NaHSO3 9.36
bottom product
Sulfuric acid 11
Vanillin 43.45
Water 36.18
 Vanillin Purification Section
Operation Data
3. Spray drying
Parameter Value
◉ Vanillin is dried to form vaillin powder Heating Agent Steam
Temperature 152oC
Evaporation Rate 100 (kg/h)/m3

Mass Comp.
Component
(%wt)
Vanillin Powder 100
BLOCK FLOW DIAGRAM (BFD)

PFD of Vanilin from

Clove Leaf Oil
PROCESS FLOW DIAGRAM (PFD)

BFD of Vanilin from

Clove Leaf Oil
PROCESS FLOW DIAGRAM (PFD) CONT’D

Stream Information
 MASS & ENERGY
5 BALANCE
 Overall Mass Balance
Components Input Output
kg/year kg/h kg/year kg/h
Acetaldehyde 0 0 162.254 0.02048662
Azobenzene 0 0 671.168 0.08474343
Diethyl Ether 792000 100 792 0.1
Diethylether-Vanillin 0 0
DMSO 2376000 300 2088235 263.666035
Clove Oil 1980000 250 741731 93.652904
Ethyl Alcohol 593406 74.925 305202 38.5356061
Overall Eugenol 0 0

Mass Balance HCl

Isoeugenol
748440
0
94.5
0
69535
120275
8.77967172
15.1862374
K-eugenolat 0 0 97 0.01224747
K-isoeugenolat 0 0 591141 74.6390152
K-vanilat 0 0 70403 8.88926768
KCl 0 0 1037245 130.965278
KOH 896861 113.24003 0 0
Na-eugenolat 0 0 315785 39.8718434
NaHSO3 792000 100 420761 53.1263889
Nitrobenzene 1188000 150 620392 78.3323232
Sodium Chloride 0 0 418784 52.8767677
For more details, click Sodium Hydroxide 285120 36 14964 1.88939394
BIO33_NME REPORT_ASSIGNMENT1.xlsx Sulfur Dioxide 0 0 252164 31.8388889
Sulfuric Acid 633600 80 247542 31.255303
Vanilin 0 0 977043 123.364015
Water 11526253 1455.335 11894989 1501.89255
 Overall Energy Balance
Machines Input Output
Per year Per hour Per year Per hour
Reactor I (P-7 / R -101) 75739.212 9.563031818 75111.192 9.483736364
Decanter Centrifugation I (P-14 / DC-101) -93888.99 -11.85467045 -93155.7423 -11.76208867
Storage I (P-16 / V-106) 0 0 0 0
Reactor II (P-9 / R-102) 97112.00959 12.26161737 113018.8661 14.27005885
Decanter Centrifugation II (P-25 / DC-102) -113018.8661 -14.27005885 -112390.3509 -14.19070087
Reactor III / Kinetic (P-10 / R-103) 314035.0498 39.65089013 134980.2999 17.04296716
Condenser I (P-15 / HX-104) -130866.335 -16.52352714 -275957.2716-34.84308985
Storage II (P-18 / V-105) 0 0 0 0
Cooler I (P-3 / HX-101) -8443.648162 -1.066117192 -8443.648162 -1.066117192
Overall Reactor IV (P-11 / R-104)
Reactor V / Kinetic (P-1 / R-108)
7044.25474 0.889426104 7328.320631 0.925293009
114232.4087 14.42328392 109696.4516 13.85056207
Energy Balance Cooler II (P-12 / HX-102)
Reactor VI (P-13 / R-105)
-92868.88568 -11.7258694 -92868.88568 -11.7258694
16260.32101 2.053070835 141419.5162 17.85599951
Blending Tank I (P-4 / V-103) 48.23686921 0.006090514 7001.373345 0.884011786
Decanter Centrifugation III (P-8 / DC-103) -30372.2404 -3.834878839 -30076.47515 -3.797534741
Reactor VII (P-19 / R-106) 11701.8567 1.477507159 10851.08012 1.370085873
Decanter Centrifugation IV (P-5 / DC-104) -10851.08012 -1.370085873 -10780.24064 -1.361141495
Evaporator I (P-20 / EV-101) 5222.594056 0.659418441 3790.093792 0.478547196
Condenser II (P-2 / HX-103) -3265.704 -0.412336364 -4772.952 -0.602645455
For more details, click
Reactor VIII (P-17 / R-107) 15578.47983 1.966979776 21281.07815 2.687004816
BIO33_NME Blending Tank II (P-21 / V-108) 26003.05584 3.283214121 20429.82514 2.579523376
REPORT_ASSIGNMENT1. -
-2.6016282
xlsx Decanter Centrifugation V (P-6 / DC-105) -20429.82514 -2.579523376 20604.89534
Evaporator II (P-22 / EV-102) 8603.65848 1.086320515 7191.106049 0.907967935
Condenser III (P-23 / HX-105) -3265.704 -0.412336364 -3181.968 -0.401763636
Spray Dryer (P-24 / SDR-101) 0 0 0 0
Total 184309.8591 23.27144685 -133.2268559 -0.016821573
 Mass & Energy Efficiency
Calculation

◉ Efficiency power plant can be calculated with the equation

shown below:
Energy in
η=
Energy out
◉ The calculation of total system efficiency is a simple and
useful method that evaluates what is produced compared to
what is consumed.
184309.8591
𝜂= 𝑥 100% = 138300.429%
133.2268559
Product Conversion
Efficiency

Product conversion efficiency can be calculated

in below:
𝑚𝑒𝑢𝑔𝑒𝑛𝑜𝑙 𝑟𝑒𝑎𝑐𝑡𝑒𝑑
𝜂= x 100%
𝑚𝑐𝑙𝑜𝑣𝑒 𝑜𝑖𝑙
200 𝑘𝑔/ℎ
𝜂= x 100%
250 𝑘𝑔/ℎ
𝜂 = 80%
Product Yield

Product yield based on reactant (clove oil) can

be calculated as:

123.364015 𝑘𝑔/ℎ
𝑌𝑖𝑒𝑙𝑑𝑏𝑎𝑠𝑒𝑑 𝑜𝑛 𝑐𝑙𝑜𝑣𝑒 𝑜𝑖𝑙 = 𝑥 100%
250 𝑘𝑔/ℎ
= 49.34%
Energy Consumption of Unit
Product

𝑇𝑜𝑡𝑎𝑙 𝑟𝑒𝑞𝑢𝑖𝑟𝑒𝑑 𝑒𝑛𝑒𝑟𝑔𝑦

𝐸𝑛𝑒𝑟𝑔𝑦 𝑐𝑜𝑛𝑠𝑢𝑚𝑝𝑡𝑖𝑜𝑛 =
𝑘𝑔 𝑣𝑎𝑛𝑖𝑙𝑙𝑖𝑛 𝑝𝑟𝑜𝑑𝑢𝑐𝑒𝑑
184309.8591 𝑘𝐽/ℎ
𝐸𝑛𝑒𝑟𝑔𝑦 𝑐𝑜𝑛𝑠𝑢𝑚𝑝𝑡𝑖𝑜𝑛 =
123.364015 𝑘𝑔/ℎ
𝑘𝐽
= 1494.0326 𝑣𝑎𝑛𝑖𝑙𝑙𝑖𝑛 𝑝𝑟𝑜𝑑𝑢𝑐𝑒𝑑
𝑘𝑔
4 CONCLUSIONS
1. The ideas of substitute vanillin sources is because natural vanillin from vanilla bean is very
laborious to cultivate, has long production periods and very expensive comparatively to synthetic
counterpart.
2. Clove leaf oil is chosen as main raw material considering the fact of its availability and
potentiality in Indonesia.
3. Kawasan Industri Cikande, Banten, is chosen as vanillin plant location with minimum wages in
Rp 3,542,713.50.
4. Based on the market analysis, the production capacity of writer’s vanillin plant is about 950
ton/year or 2.88 ton/day by fulfilling 5% of global market share.
5. The production of vanillin are divided into 4 section including eugenol isolation, isomerization,
oxidation, and purification.
6. Continuous process is selected due to high production capacity to meet the global vanillin
demand and long purification procedure to have 100% purity of vanillin powder.
7. Purification of vanillin requires extraction and re-extraction method using diethylether as
waterimmiscible organic solvent.
8. The production capacity in this vanillin plant is 977 tons/year which is higher than the vanillin
demand.
Thank You
 Reference

Solvay Chemicals International. 2004. Liquid Specific Soda – Specific Heat. USA: Solvay Chemicals, PCH-1110-0004-W-EN (WW)
Cerveny, L., Krejcikova, A., Marhoul, A. dan Ruzicka, V. 1986. Isomerization of Eugenol to Isoeugenol. [ONLINE] Diakses di
https://www.thevespiary.org/rhodium/Rhodium/Vespiary/talk/files/1268-Isomerization-of-eugenol-to-isoeugenolpdfae22.pdf pada 18
September 2018.
Bryan, Collis. 1950. Vanillin purification by distillation. US Patent No. 2506540A
Mulyono, Edy. 2012. Perancangan Proses Produksi Isoeugenol dan Vanilin dari Eugenol Minyak Daun Cengkeh. Disertasi, Sekolah
Pascasarjana. Bogor: Institut Pertanian Bogor
Cisadesi, Rosi. 2007. Pembuatan Vanilin Semi Sintetik dari Isoeugenol Minyak Cengkeh Dengan Pemanasan Gelombang Mikro.
Skripsi, Sarjana Teknologi Pertanian. Bogor: Institut Pertanian Bogor
Liana, R. L., Hidayat, N. dan Rahmah, N. L. 2014. Permunian Eugenol dari Minyak Daun Cengkeh dengan Reaktan Basa Kuat (Kajian
Konsentrasi Reaktan). Jurnal Industria Vol 3, No 1, Hal 1-12.