Report Compiled 1

Department of Chemical and Environmental Engineering

University of Nottingham

BENZALDEHYDE

PRODUCTION

GROUP 12

Group Members: 1) Adamu AbuBakar Rasheed

2) Cobham Emmanuel Itam

3) Nasir Muzaffar Kotriwala

4) Teh Yong Chuan

Lecturers: 1) Prof. Dominic Foo

2) Dr. Denny Ng

3) Dr. Lam Hon Loong

nasir

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- 010096

nasir

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- 009390

nasir

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nasir

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- 005831

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- 006379

Table of Content

1.0 Introduction 1

2.0 Overview of Reaction Pathways 1

2.1 Chlorination of Toluene coupled with Hydrolysis of Benzal Chloride 1

2.2 Liquid Phase Oxidation of Toluene 2

2.3 Oxidation of Benzyl Alcohol 4

3.0 Reaction Path Selection 5

4.0 Process Synthesis 6

5.0 Process Flow Diagram (Liquid Phase Oxidation of Toluene) 7

6.0 Hysys Simulation Diagram 8

7.0 Mass Balance 9

References 10

1 | P a g e

1.0 Introduction

Benzaldehyde, the most valuable industrial aromatic aldehyde, is used as a flavouring agent

for food and an intermediate for pharmaceuticals, dyes, perfume and flavouring chemicals.

(Opgrande,J.W 2004) (Kantam,M.L., et al.2002).

2.0 Overview of Reaction Pathways

Liquid-Phase Air Oxidation of Toluene and Acid Hydrolysis of Benzalchloride, which are

principally used by current industry to manufacture Benzaldehyde, along with the

discontinued industrial process of Oxidation of Benzyl Alcohol to manufacture Benzaldehyde

have been evaluated to manufacture 50,000 MTA of Benzaldehyde.(Ullmann, 2003)

2.1 Chlorination of Toluene coupled with Hydrolysis of Benzal Chloride

Overall Reaction

Reactivity of Chlorine molecule, facilitated by means of activation via light or heat, enables

exchanging a hydrogen atom with the methyl molecule. Consequently, benzalchloride and

benzylchloride are produced. Benzalchloride, the intermediate for hydrolysis in presence of

presence of concentrated sulphuric acid, needs to be free from benzylchloride. (len1, 2008)

The undesirable formation of benzylchloride can be minimized by the maintaining the

chlorination temperature between 195-197oC at 1 atm. (len1, 2008). The recommended

operating conditions for hydrolysis are 100-200oC at atmospheric pressure. (len1, 2008)

Economical Potential

C6H5CH3 + Cl2 + H2O C6H5CHO + 2HCL

Kg mole 1 1 1 1 2

Mole Weight 92.14 70.91 18.02 106.12 36.46

Kg 92.14 70.91 18.02 106.12 72.92

Kg/Kg C6H5CHO 0.87 0.69 0.17 1.00 0.69

$/Kg 1.33 0.38 0 3.81 0.11

Table 1: Economic Potential of Chlorination of Toluene coupled with Hydrolysis.

Price adapted from (ICIS, 2011) and (Creators, 2010)

Gross Profit = [(3.81 x 1) + (0.11 x 0.69) – (1.33 x 0.87) - (0.38 x 0.69)] x 1000

= $ 2466.60/tonne of benzaldehyde

2 | P a g e

Safety

The chemicals involved are stable in terms of reactivity. Toluene is flammable and

combustible. Chlorine gas is easily vaporised due to its low boiling point.(Vee Gee Scientific

Inc., 2004)

Environmental Impact

All the raw materials and product found in this process are long-term biodegradable.

Especially, toluene is dangerous to aquatic life in high concentration and fouling shoreline

(Mark Van, et al., 1997). Furthermore, hydrochloric acid will accelerate the dissolution of

mineral like carbonates and all aluminosilicates. Thus it contributes to the decay of buildings

and structure (National Pollutant Inventory, 2011) Chlorine is extremely harmful to humans;

may cause tracts burn, skin burn or eyes burn if contacted. (Matheson Tri-Gas, Inc., 2002)

Dilute sulphuric acid, which isn’t permitted to be flushed into water at large scale, is formed

as a waste product in substantial quantities.(Ullman,2003)(Cartwright,2003)

2.2 Liquid Phase Oxidation of Toluene

Overall Reaction

Adapted from (Hoorn, et al., 2005)

Air oxidation of Toluene in liquid-phase is currently the world’s largest source of synthetic

Benzaledyhde.(Opgrande,J.W 2004) Vapour-phase oxidation of Toleuene, the dominant

3 | P a g e

process to manufacture Benzaldehyde in 1950-60s, isn’t industrially important anymore.

Instead, liquid-phase oxidation offers higher yields of Benzaldehyde and lower undesirable

by-products of Carbon Monoxide and Carbon Dioxide relatively. (Opgrande,J.W 2004)

Manganese(II) acetate, amongst various possible catalysts, has been selected to oxidize

Toluene in liquid-phase. Bromide promoter, acetic acid solvent and Lewis Acid [stannous(II)

chloride], which increases selectivity of Benzaldehyde, in the composite catalyst system

facilitate higher Benzaldehyde yields, milder operating conditions [1200C, 70-400 psig] and

cheaper catalyst costs in comparison to other catalysts respectively. 18% Single-pass

Toluene conversion and 68% Benzaldehyde selectivity have been used in our analysis.

(Chaudhari, et al., 2008)

Economic Potential

Since the side-reactions are not negligible selectivity of each product has been accounted

for ascertaining the economic potential.(Chaudhari, et al., 2008) 18kg of Toluene would be

consumed, when taking 100 kg Toluene as basis, as single-pass conversion is 18% .

C6H5CH3 + O2 C6H5CHO + C6H5COOH + C6H5CH2OCOCH3 + C6H5CH2OH

Mole (kmol) 1 1 1 1 1 1

Mole Weight (kg/kmol)

92.14 16 106.12 122.12 150.18 108.14

Selectivity - - 68 17 10.20 5.30

Weight (kg) 18 6.25 12.24 3.06 1.86 0.954

kg/kg benzaldehyde

1.47 0.51 1 0.25 0.15 0.078

$/kg 1.33 0 3.81 1.94 3.9 3.5

Table 2: Economy Potential for Liquid Phase Oxidation of Toluene.

Price adapted from (ICIS, 2011)

Gross Profit = [(3.81 x 1) + (1.94 x 0.25) + (3.9 x 0.15) + (3.5 x 0.078) – (1.33 x 1.47) - 0] x 1000

= $ 3197.90/tonne of benzaldehyde.

Safety

Toluene must be prevented from undergoing exothermic polymerisation as it can lead to

fire/explosion hazard. (Emerald, 2006) (Vee Gee Scientific Inc., 2004)


Minor emissions of Carbon monoxide and Carbon Monoxide occur. (Chaudhari, et al., 2008)

Leakage of Toluene and Manganese(II) Acetate may harm aquatic life (Mark Van, et al.,

1997), (Orica Chemicals, 2008). However, Manganese Acetate can be reused for the

oxidation process instead of harmful disposal by recovering it via solvent extraction or

distillation.

4 | P a g e

2.3 Oxidation of Benzyl Alcohol

Overall Reaction

Adapted from (Satrio & Doraiswamy, 2000)

Benzylchloride, in presence of sodium hydroxide, is hydrolysed to benzyl alcohol followed by

further oxidation of the product, benzyl alcohol to benzaldehyde in the same reactor using

sodium hypochlorite. (Satrio & Doraiswamy, 2000) Single-pass conversion and selectivity,

under the recommended operating conditions are 90oC and 10 bars, are limited to 18.1%

and 45.3% respectively. (Satrio & Doraiswamy, 2000)

Economic Potential

Since the side-reactions are not negligible selectivity of each product has been accounted

for ascertaining the economic potential. Since 18.1% single-pass conversion of benzyl

chloride occurs 18.1kg of toluene are assumed to be consumed taking 100kg of benzyl

chloride as basis.

C6H5CH2Cl + NaOH + NaOCl C6H5CHO + C6H5CH2OH

Mole (kmol) 1 1 1 1 1

Mole Weight (kg/kmol)

126.58 40.00 74.44 106.12 108.14

Selectivity - - - 45.3 54.7

Weight (kg) 18.1 5.72 10.64 8.20 9.91

kg/kg benzaldehyde

2.21 0.70 1.30 1.00 1.20

$/kg 1.97 0.65 0.24 3.81 3.50

Table 3: Economic Potential for Oxidation of Benzyl Alcohol

Price adapted from (Seper, 2001), (ICIS, 2011) and (Johnston, 2010)

Gross Profit = [(2.21 x 1.97) + (0.65 x 0.7) + (0.24 x 1.3) - (3.81 x 1)-(3.5 x 1.2)] x 1000

= $ 2889.30/tonne of benzaldehyde

5 | P a g e

Safety

All chemicals involved in the reaction are combustible. Sodium hydroxide is very hazardous

in case of skin contact (Sciencelab, 2010). Lastly, benzyl chloride is corrosive and inhalation

of air containing benzyl chloride may cause lung burn (SEPA, 2011).


Sodium hydroxide, by virtue of raising the pH of aquatic environment, is very toxic to

aquatic life. (Horizon, 2004)

3.0 Reaction Path Selection

Reaction Path Gross Profit ($/tonne)

1) Liquid Phase Oxidation of Toluene 3197.90

2) Chlorination of Toluene coupled with Hydrolysis of Benzal Chloride 2466.60

3) Oxidation of Benzyl Alcohol 2899.30

Table 4: Economy Potential Comparison between Various Processes.

Considering the aforementioned factors, liquid phase oxidation of toluene is deemed to be

the most appropriate reaction pathway for large-scale benzaldehyde manufacture.

Firstly, liquid phase oxidation of toluene exhibits highest economy potential as shown in

Table 4. Secondly, the 68 % selectivity of benzaldehyde significantly exceeds that achieved

in oxidation of benzyl alcohol whilst roughly maintaining the same single-pass

conversion[18%]. Furthermore, Benzaldehyde produced from chlorination process doesn’t

conform to food grade quality, thereby reducing the flexibility of demand for our

benzaldehyde product. (Chaudhari, et al., 2008) Furthermore, the by-product of the

Chlorination process, Hydrochloric Acid may potentially sell at depressed prices if there’s

abundant supply of Hydrochloric acid in our petrochemical complex.(Seider, et al. 2010)

Higher capital and maintenance cost are required by the chlorination process in order to

combat corrosiveness, which may potentially lead to emission of poisonous chlorine.

Moreover, oxidation of alcohol employs Sodium Hydroxide, which is harmful to aquatic life

if leaked. Furthermore, hydrochloric acid in chlorination of toluene may cause decay of

building and structure. Conversely, Liquid phase oxidation of toluene, by producing only

minor emissions of Carbon Monoxide and Carbon Dioxide, avoids substantial emissions of

pollutant residues. Hence, it’s relatively the most environmental friendly process.

6 | P a g e

4.0 Process Synthesis

The oxidation agent can theoretically be either pure Oxygen or Air. Air is selected as all

industrial processes employing liquid-phase oxidation of Toluene use Air. Since the patent,

relied upon in this study, doesn’t report any adverse effect on the catalyst by use of Air it

implies that the inert Nitrogen doesn’t need to be removed before the reactor.

(Chaudhari, et al., 2008) Moreover, the substantial amount of inert Nitrogen absorbs the

heat generated by the exothermic oxidation reaction, thereby maintaining the reactor

effluent temperature at a mild temperature of 135.8°C. Air has been provided in excess in

order to facilitate recycled Toluene to be completely consumed.

Owing to unavailability of published kinetics data for the catalyst, used in this study, the

Arrhenius graph couldn’t be used to ascertain the favourable operating temperature range.

Instead, personal judgement was used to ascertain the optimum combination of single-pass

conversion and Benzaldehyde selectivity to be 18% and 68% from the various experiment

results, which occur at 120°C and 300 psig as reported in the patent. 76% Benzaledhyde

selectivity was also reported. However, it wasn’t selected since the single-pass conversion

was limited to only 10% (Chaudhari, et al., 2008)

Since the reactor effluent is distributed between liquid and vapour phases, partial

condensation has been used after the reactor as liquid is easier to separate than vapour.

The vapours of unconverted Oxygen and inert Nitrogen, collected by vapour recovery

system, aren’t recycled as recycle costs aren’t economically viable considering that air is free

of charge.

Benzaldehyde produced from liquid oxidation of Toluene often contains minor odiferous

impurities that discolour the product and are difficult to remove by distillation.

(Ullmann,2003) These impurities have been removed by treating the impure benzaldehyde

simultaneously with water and zinc powder followed by distillation. (Jongsma, C., 2008)

A direct distillation sequence was used to recover the products as it’s generally considered

to be the most desirable sequence. Slightly higher than atmospheric pressures, in order to

avoid vacuum operation, were used in distillation columns as the boiling points of Toluene,

Benzaldehyde and Benzoic Acid(110°C, 179°C and 249°C) are widely spread at atmospheric

pressure. The difficult separation of separating the relatively low output of Benzyl Alcohol

and Benzyl acetate, which have boiling points of 205.4°C and 212°C , wasn’t pursued owing

to the capital-intensive nature. Catalyst is recovered for recycle by means of solvent

extraction of the bottoms product of the last distillation tower (Chaudhari, et al., 2008).

Prior to recycle of Toluene an adiabatic flash drum is used to remove in order to prevent

vapour from entering the pump feeding Toluene to the reactor.The Benzaldehyde recovered

is 98.6% pure, which exceeds the industrial specification of 98.0%.(Opgrande,J.W. 2004)

BENZALDEHYDE: LIQUID PHASE OXIDATION OF TOLUENEAir

101.3Kpa, 300C

C-01

E-01

C-02

E-02

C-03

E-03

Reactor at 1200C and

2170Kpa

Toluene

Storage

P-01

HE-01

E-05

V-01

F-01

V-02

To Stack

Treatment to

remove impurities

causing

discoloration

before distillation

Impurities

V-03

HE-02D-01

E-06

P-03

Heat in

Heat out

R-01

D-02

E-08

E-09

P-04

P-05

Heat in

Heat out

R-02

Benzaldehyde

Storage

Under

Nitrogen

Blanket

Heat in

Heat out

Benzoic Acid

StorageHeated

Tank

CATALYST

RECOVERY BY LLE

By

Products

Storage

D-03

735000Kg/h

1200C

2170Kpa

135.80C

2170Kpa

44.970C

2158Kpa44.97

0C

2158Kpa

25660kg/h

101Kpa

44.970C

120Kpa

110.60C

120Kpa

49830kg/h

44.970C

2158Kpa

49830kg/h

193.60C

122Kpa

9388kg/h

115.30C

118Kpa

40440kg/h

300C

2172Kpa

61260kg/h

E-07

101.3Kpa

21200kg/h

228.40C

120Kpa

3051kg/h

300C

6336kg/h

184.80C

118Kpa

6336kg/h

E-11

256.60C

120Kpa

1608kg/h

300C

1608kg/h

E-10

P-06

R-03

E-12

300C

3051kg/h

209.90C

118Kpa

1608kg/h

1200C

2172Kpa

61260kg/h

To Stack

F-02

300

C

40440kg/h

300C

40440kg/h

P-07

P-02

LEGENDC- CompressorsHE- HeaterR- ReboilerE- CoolerP- PumpD- Distillation ColumnF- Flash DrumV- ValveD-01 Toluene ColumnD-02 Benzaldehyde Column

D-03 Benzoic Acid Column

Mon Oct 24 21:18:11 2011 Case: H:\PSD\PSD CW\PSD COMPLETED SIMULATION GROUP 12.HSC Flowsheet: Case (Main)

Compressor

Air 1

QComp-1

Pump1

Make-upToluene

PressurisedToluene

QP-1

InterCooler

2

QCool1

Comp2

3

QComp2

InterCooler2

4

QCool2

K-100

55

Qcomp3

InterCooler3

PressurisedAir

QCool3

Heater1

ToluenetoReactor

QHeat1

Reactor

Products

FlashDrum

Cooler1

6

QCooler

Air toatmosphere

7 Treatmentof impuritiescausingdiscolorationbeforedistillation

Impurities

8

Valve 1ToFlash

Valve 29

E-103

gdfgd

VLV-102to stack

CondenserRecyletoluene

Qcond

RCY-1

RrecycleToluene

V-100

ToStacktoo

Torecycle

MIX-100

Toluene

TolueneColumn

10

Tolueneand Air

Heatin

E-01

BenzaldehydeColumn

Benzaldehyde

E-02

Heatin 2

Bottoms

BenzoicAcidColumn

BZolandBacetate

Benzoicacid

E-102

Heat in3

ByProducts

Cooler2

Benzaldehyde to storage

HE-01

Cooler3

To Storage

HE-02

Cooler4

BZoic andCatalyst

HE-03

LiquidLiquidSeparation

CatalystRecovery

Benzoic Acid tostorage


Material Streams

Vapour Fraction

Temperature

Pressure

Molar Flow

Mass Flow

Liquid Volume Flow

Heat Flow

C

kPa

kgmole/h

kg/h

m3/h

kJ/h

Air

1.0000

30.00

101.3

2.548e+004

7.350e+005

849.7

3.547e+006

1

1.0000

163.2

278.9

2.548e+004

7.350e+005

849.7

1.039e+008

Make-up Toluene

0.0000

30.00

101.3

230.1

2.120e+004

24.37

3.101e+006

Pressurised Toluene

0.0000

31.92

2172

667.2

6.126e+004

70.40

8.364e+006

2

1.0000

120.0

276.9

2.548e+004

7.350e+005

849.7

7.101e+007

3

1.0000

306.2

837.0

2.548e+004

7.350e+005

849.7

2.149e+008

4

1.0000

120.0

835.0

2.548e+004

7.350e+005

849.7

7.051e+007

55

1.0000

278.1

2172

2.548e+004

7.350e+005

849.7

1.924e+008

Pressurised Air

1.0000

120.0

2170

2.548e+004

7.350e+005

849.7

6.936e+007

Toluene to Reactor

0.0000

120.0

2170

667.2

6.126e+004

70.40

1.834e+007

Products

1.0000

135.8

2170

2.619e+004

7.963e+005

917.9

8.769e+007

6

0.9798

45.00

2168

2.619e+004

7.963e+005

917.9

-9.731e+006

Vapour Fraction

Temperature

Pressure

Molar Flow

Mass Flow

Liquid Volume Flow

Heat Flow

C

kPa

kgmole/h

kg/h

m3/h

kJ/h

Air to atmosphere

1.0000

44.97

2158

2.566e+004

7.464e+005

862.5

-2.935e+006

7

0.0000

204.6

2158

530.0

4.983e+004

55.37

9.239e+006

Impurities

1.0000

204.6

2158

0.0000

0.0000

0.0000

0.0000

8

0.0000

204.6

2158

530.0

4.983e+004

55.37

9.239e+006

To Flash

0.9798

44.97

2158

2.619e+004

7.963e+005

917.9

-9.731e+006

9

0.5127

123.7

120.0

530.0

4.983e+004

55.37

9.239e+006

to stack

1.0000

40.69

101.3

2.566e+004

7.464e+005

862.5

-2.935e+006

Recyle toluene

0.0167

30.00

108.0

446.2

4.044e+004

46.47

5.029e+006

recycle Toluene

0.0000

30.00

108.0

437.2

4.006e+004

46.03

5.066e+006

To Stack too

1.0000

30.00

108.0

7.438

231.3

0.2703

-5.279e+004

To recycle

0.0000

30.00

108.0

438.8

4.021e+004

46.20

5.082e+006

Toluene

0.0000

30.00

101.3

667.2

6.126e+004

70.40

8.167e+006

Vapour Fraction

Temperature

Pressure

Molar Flow

Mass Flow

Liquid Volume Flow

Heat Flow

C

kPa

kgmole/h

kg/h

m3/h

kJ/h

10

0.0698

110.6

120.0

530.0

4.983e+004

55.37

2.204e+005

Toluene and Air

1.0000

115.3

118.0

446.2

4.044e+004

46.47

2.571e+007

Benzaldehyde

1.0000

184.8

118.0

59.71

6336

6.046

-9.385e+005

Bottoms

0.0000

193.6

122.0

83.74

9388

8.899

-1.021e+007

BZol and Bacetate

1.0000

209.9

118.0

10.86

1443

1.372

-2.025e+006

Benzoic acid

0.0000

256.5

120.0

13.17

1608

1.481

-4.048e+006

By Products

0.0000

228.4

120.0

24.03

3051

2.853

-6.640e+006


0.0000

30.00

118.0

59.71

6336

6.046

-5.272e+006

To Storage

0.0000

30.00

118.0

10.86

1443

1.372

-3.083e+006

BZoic and Catalyst

0.0000

30.00

120.0

13.17

1608

1.481

-4.701e+006

Catalyst Recovery

0.0000

30.00

120.0

0.0000

0.0000

0.0000

0.0000

Benzoic Acid to storage

0.0000

30.00

120.0

13.17

1608

1.481

-4.701e+006


Compositions

Comp Mole Frac (Toluene)

Comp Mole Frac (Nitrogen)

Comp Mole Frac (Oxygen)

Comp Mole Frac (BZal)

Comp Mole Frac (BZoicAcid)

Comp Mole Frac (BZ-Acetate)

Comp Mole Frac (AceticAcid)

Comp Mole Frac (BZol)

Comp Mole Frac (H2O)

Air

0.0000

0.7900

0.2100

0.0000

0.0000

0.0000

0.0000

0.0000

1

0.0000

0.7900

0.2100

0.0000

0.0000

0.0000

0.0000

0.0000

Make-up Toluene

1.0000

0.0000

0.0000

0.0000

0.0000

0.0000

0.0000

0.0000

Pressurised Toluene

0.9953

0.0005

0.0001

0.0001

0.0000

0.0000

0.0000

0.0041

2

0.0000

0.7900

0.2100

0.0000

0.0000

0.0000

0.0000

0.0000

3

0.0000

0.7900

0.2100

0.0000

0.0000

0.0000

0.0000

0.0000

4

0.0000

0.7900

0.2100

0.0000

0.0000

0.0000

0.0000

0.0000

55

0.0000

0.7900

0.2100

0.0000

0.0000

0.0000

0.0000

0.0000

Pressurised Air

0.0000

0.7900

0.2100

0.0000

0.0000

0.0000

0.0000

0.0000

Toluene to Reactor

0.9953

0.0005

0.0001

0.0001

0.0000

0.0000

0.0000

0.0041

Products

0.0208

0.7684

0.2043

0.0023

0.0005

0.0002

0.0002

0.0033

6

0.0208

0.7684

0.2043

0.0023

0.0005

0.0002

0.0002

0.0033










Air to atmosphere

0.0042

0.7841

0.2084

0.0000

0.0000

0.0000

0.0000

0.0032

7

0.8229

0.0114

0.0021

0.1122

0.0249

0.0121

0.0088

0.0058

Impurities

0.3302

0.3040

0.0963

0.0140

0.0007

0.0005

0.0009

0.2534

8

0.8229

0.0114

0.0021

0.1122

0.0249

0.0121

0.0088

0.0058

To Flash

0.0208

0.7684

0.2043

0.0023

0.0005

0.0002

0.0002

0.0033

9

0.8229

0.0114

0.0021

0.1122

0.0249

0.0121

0.0088

0.0058

to stack

0.0042

0.7841

0.2084

0.0000

0.0000

0.0000

0.0000

0.0032

Recyle toluene

0.9770

0.0135

0.0025

0.0001

0.0000

0.0000

0.0000

0.0068

recycle Toluene

0.9929

0.0007

0.0001

0.0001

0.0000

0.0000

0.0000

0.0063

To Stack too

0.0453

0.7702

0.1452

0.0000

0.0000

0.0000

0.0000

0.0394

To recycle

0.9928

0.0007

0.0001

0.0001

0.0000

0.0000

0.0000

0.0063

Toluene

0.9953

0.0005

0.0001

0.0001

0.0000

0.0000

0.0000

0.0041










10

0.8229

0.0114

0.0021

0.1122

0.0249

0.0121

0.0088

0.0058

Toluene and Air

0.9770

0.0135

0.0025

0.0001

0.0000

0.0000

0.0000

0.0068

Benzaldehyde

0.0019

0.0000

0.0000

0.9864

0.0000

0.0000

0.0117

0.0000

Bottoms

0.0014

0.0000

0.0000

0.7093

0.1573

0.0766

0.0554

0.0000

BZol and Bacetate

0.0000

0.0000

0.0000

0.0459

0.0006

0.5905

0.3630

0.0000

Benzoic acid

0.0000

0.0000

0.0000

0.0000

0.9999

0.0001

0.0001

0.0000

By Products

0.0000

0.0000

0.0000

0.0208

0.5482

0.2670

0.1641

0.0000


0.0019

0.0000

0.0000

0.9864

0.0000

0.0000

0.0117

0.0000

To Storage

0.0000

0.0000

0.0000

0.0459

0.0006

0.5905

0.3630

0.0000

BZoic and Catalyst

0.0000

0.0000

0.0000

0.0000

0.9999

0.0001

0.0001

0.0000

Catalyst Recovery

0.0000

0.0000

0.0000

0.0000

0.9999

0.0001

0.0001

0.0000

Benzoic Acid to storage

0.0000

0.0000

0.0000

0.0000

0.9999

0.0001

0.0001

0.0000

References

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Oxidation Incorporation of Mass Transfer Phenomena, Volume A2, p. 186.

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12) Johnston, J., 2010. 2011 Water Treatment Chemicals, s.l.: Des Moines Water Works.

13) Jongsma, C., 2008. Process for the purification of benzaldehyde . USA, Patent No. 4379026.

14) Kantam,M.L., et al.2002 An improved process for selective liquid-phase distillation of toluene,

81(3-4), pp. 223-232.

15) len1, 2008. Benzotrichloride, Benzoyl Chloride, and Phthalyl Chloride - Illustrated Practical Guide.

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Available at: http://www.lenntech.com/periodic/elements/cl.htm


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Toluene Entry, p. 7.

18) Mark Van, M., Stevens, L., Seese, M. D. & Basham, W., 1997. Environmental Contaminants

Encyclopedia. Toluene Entry, p. 7.

19) MATHESON TRI-GAS, INC., 2002. Material Safety Data Sheet, NEW JERSEY: MATHESON TRI-GAS,

INC..

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Available at: http://www.npi.gov.au/substances/hydrochloric-acid/environmental.html


21) Orica Chemicals, 2008. Material Safety Data Sheet, Melbourne: Orica Australia Pty Ltd .

22) Opgrande,J.W. 2004. Kirk-Othmer Encyclopedia of Chemcial Technology. Benzaldehyde

23) Pashkova, A. & Greine, L., 2011. Chemie Ingenieur Technik. Towards Small-Scale Continuous

Chemical Production: Technology Gaps and Challenges, 83(9), pp. 1337-1342.

24) Satrio, J. A. & Doraiswamy, L., 2000. Two Step Process. Production of Benzaldehyde: A Case

Study in a Possible Industrial, Issue 82, p. 48.

25) Sciencelab, 2010. Material Safety Data Sheet, Texas: Sciencelab.com, Inc.

26) Sciencelab, 2010. Material Safety Data Sheet Benzaldehyde MSDS, Texas: Sciencelab.com, Inc..

27) Sciencelab, 2010. Material Safety Data Sheet Hydrochloric Acid MSDS, Texas: Sciencelab.com,

Inc..

28) Sciencelab, 2010. Material Safety Data Sheet Toulene MSDS, Texas: Sciencelab.com, Inc..

29) SEPA, 2011. Sccottish Pollutant Release Inventory. [Online]

Available at: http://apps.sepa.org.uk/spripa/Pages/SubstanceInformation.aspx?pid=24


30) Seider,W.D. et al. 2010. Product and Process Design Principles. John Wiley & Sons. USA

31) Seper, K. W., 2001. Kirk-Othmer Encyclopedia of Chemcial Technology. Benzyl Chloride, Benzal

Chloride, and Benzotrichloride.

32) Ullmann, F. E. B. A. H., 2003. Ullmann's Encyclopedia of Industrial Chemistry. Volume 6th.

33) Vee Gee Scientific Inc., 2004. Toluene Material Safety Data. [Online]

Available at: http://www.ee.iitb.ac.in/~nanoe/msds/toluene.pdf.


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