Department of Chemical and Environmental Engineering University of Nottingham

BENZALDEHYDE PRODUCTION
GROUP 12
1) Adamu AbuBakar Rasheed - 010096 2) Cobham Emmanuel Itam 3) Nasir Muzaffar Kotriwala 4) Teh Yong Chuan
- 009390

Group Members:

- 005831 - 006379

Lecturers:

1) Prof. Dominic Foo 2) Dr. Denny Ng 3) Dr. Lam Hon Loong

0 5.3 Chlorination of Toluene coupled with Hydrolysis of Benzal Chloride Liquid Phase Oxidation of Toluene Oxidation of Benzyl Alcohol 1 1 1 2 4 5 6 7 8 9 3.0 7.0 6.2 2.0 Introduction Overview of Reaction Pathways 2.0 4.Table of Content 1.0 Reaction Path Selection Process Synthesis Process Flow Diagram (Liquid Phase Oxidation of Toluene) Hysys Simulation Diagram Mass Balance References 10 .1 2.0 2.

0 Introduction Benzaldehyde. (len1. along with the discontinued industrial process of Oxidation of Benzyl Alcohol to manufacture Benzaldehyde have been evaluated to manufacture 50.38 x 0. et al. 2008) Economical Potential C6H5CH3 + Cl2 + H 2O  C6H5CHO + Kg mole 1 1 1 1 Mole Weight 92. (Opgrande. The recommended operating conditions for hydrolysis are 100-200oC at atmospheric pressure. benzalchloride and benzylchloride are produced.M.91 18.46 72. perfume and flavouring chemicals.60/tonne of benzaldehyde 2HCL 2 36.00 $/Kg 1. Consequently.38 0 3. the most valuable industrial aromatic aldehyde. enables exchanging a hydrogen atom with the methyl molecule.11 1|Page . dyes.12 Kg 92.87) .(0.69)] x 1000 = $ 2466.1 Chlorination of Toluene coupled with Hydrolysis of Benzal Chloride Overall Reaction Reactivity of Chlorine molecule.81 Table 1: Economic Potential of Chlorination of Toluene coupled with Hydrolysis.J.02 106.1. Benzalchloride. 2008).(Ullmann.. is used as a flavouring agent for food and an intermediate for pharmaceuticals.91 18. 2010) Gross Profit = [(3.33 0.33 x 0.L.2002). 2. (len1. which are principally used by current industry to manufacture Benzaldehyde. 2011) and (Creators.69) – (1.92 0.14 70. Price adapted from (ICIS.11 x 0. the intermediate for hydrolysis in presence of presence of concentrated sulphuric acid. 2003) 2.0 Overview of Reaction Pathways Liquid-Phase Air Oxidation of Toluene and Acid Hydrolysis of Benzalchloride.14 70.81 x 1) + (0.02 106. (len1.12 Kg/Kg C6H5CHO 0.87 0. 2008) The undesirable formation of benzylchloride can be minimized by the maintaining the chlorination temperature between 195-197oC at 1 atm.000 MTA of Benzaldehyde.W 2004) (Kantam. needs to be free from benzylchloride.69 0.69 0.17 1. facilitated by means of activation via light or heat.

.(Opgrande. which isn’t permitted to be flushed into water at large scale. (Matheson Tri-Gas. hydrochloric acid will accelerate the dissolution of mineral like carbonates and all aluminosilicates. skin burn or eyes burn if contacted.2 Liquid Phase Oxidation of Toluene Overall Reaction Adapted from (Hoorn. 2002) Dilute sulphuric acid. the dominant 2|Page . et al.W 2004) Vapour-phase oxidation of Toleuene.. may cause tracts burn.(Vee Gee Scientific Inc. Furthermore. Toluene is flammable and combustible.. 2011) Chlorine is extremely harmful to humans. Inc. is formed as a waste product in substantial quantities.2003)(Cartwright. 1997).(Ullman. et al. Thus it contributes to the decay of buildings and structure (National Pollutant Inventory. toluene is dangerous to aquatic life in high concentration and fouling shoreline (Mark Van. Especially.2003) 2. 2004) Environmental Impact All the raw materials and product found in this process are long-term biodegradable.J.. 2005) Air oxidation of Toluene in liquid-phase is currently the world’s largest source of synthetic Benzaledyhde. Chlorine gas is easily vaporised due to its low boiling point.Safety The chemicals involved are stable in terms of reactivity.

liquid-phase oxidation offers higher yields of Benzaldehyde and lower undesirable by-products of Carbon Monoxide and Carbon Dioxide relatively.25 12. (Chaudhari.954 kg/kg 1. 2008) Economic Potential Since the side-reactions are not negligible selectivity of each product has been accounted for ascertaining the economic potential. Price adapted from (ICIS. However. Safety Toluene must be prevented from undergoing exothermic polymerisation as it can lead to fire/explosion hazard. 1997).81 x 1) + (1.9 x 0.06 1. isn’t industrially important anymore.15) + (3. 2008).24 3.94 x 0. acetic acid solvent and Lewis Acid [stannous(II) chloride].5 x 0..25) + (3. Instead. (Chaudhari. 2004) Environmental Impact Minor emissions of Carbon monoxide and Carbon Monoxide occur..47 0.86 0. 2011) Gross Profit = [(3. 3|Page . when taking 100 kg Toluene as basis.process to manufacture Benzaldehyde in 1950-60s. amongst various possible catalysts.94 3.12 150. 18% Single-pass Toluene conversion and 68% Benzaldehyde selectivity have been used in our analysis.9 3. milder operating conditions [1200C.33 0 3. which increases selectivity of Benzaldehyde.12 122. (Opgrande. Manganese Acetate can be reused for the oxidation process instead of harmful disposal by recovering it via solvent extraction or distillation.. et al. et al.078) – (1.25 0.81 1.W 2004) Manganese(II) acetate.14 16 106.51 1 0. 2008) Leakage of Toluene and Manganese(II) Acetate may harm aquatic life (Mark Van.5 Table 2: Economy Potential for Liquid Phase Oxidation of Toluene. C6H5CH3 + O2  C6H5CHO + C6H5COOH + C6H5CH2OCOCH3 + C6H5CH2OH Mole (kmol) 1 1 1 1 1 1 Mole Weight 92. (Orica Chemicals. et al. has been selected to oxidize Toluene in liquid-phase.33 x 1.30 Weight (kg) 18 6.J. Bromide promoter.15 0.20 5. 2006) (Vee Gee Scientific Inc.18 108. 70-400 psig] and cheaper catalyst costs in comparison to other catalysts respectively.90/tonne of benzaldehyde.47) .(Chaudhari..078 benzaldehyde $/kg 1.0] x 1000 = $ 3197. (Emerald. as single-pass conversion is 18% . 2008) 18kg of Toluene would be consumed. in the composite catalyst system facilitate higher Benzaldehyde yields.14 (kg/kmol) Selectivity 68 17 10.. et al.

50 Mole (kmol) Mole Weight (kg/kmol) Selectivity Weight (kg) kg/kg benzaldehyde $/kg 1. is hydrolysed to benzyl alcohol followed by further oxidation of the product.12 45.14 54.3% respectively.00 5.1% single-pass conversion of benzyl chloride occurs 18.64 1.44 10. 2000) Single-pass conversion and selectivity. 2001).21 NaOH 1 40. 2000) Benzylchloride.91 1.21 x 1.65 x 0.97) + (0.2.24 3.00 + C6H5CH2OH 1 108.2)] x 1000 = $ 2889. C6H5CH2Cl + 1 126. Since 18.72 0.(3. (ICIS. benzyl alcohol to benzaldehyde in the same reactor using sodium hypochlorite. in presence of sodium hydroxide. (Satrio & Doraiswamy. (Satrio & Doraiswamy.1 2.20 1.7 9.65 0.1% and 45.58 18.5 x 1.70 + NaOCl 1 74. 2011) and (Johnston.81 Table 3: Economic Potential for Oxidation of Benzyl Alcohol Price adapted from (Seper. are limited to 18.7) + (0.1kg of toluene are assumed to be consumed taking 100kg of benzyl chloride as basis.3 8.3) .20 3.81 x 1)-(3.3 Oxidation of Benzyl Alcohol Overall Reaction Adapted from (Satrio & Doraiswamy.30  C6H5CHO 1 106. 2000) Economic Potential Since the side-reactions are not negligible selectivity of each product has been accounted for ascertaining the economic potential.30/tonne of benzaldehyde 4|Page .24 x 1. under the recommended operating conditions are 90oC and 10 bars. 2010) Gross Profit = [(2.97 0.

benzyl chloride is corrosive and inhalation of air containing benzyl chloride may cause lung burn (SEPA.30 Table 4: Economy Potential Comparison between Various Processes. hydrochloric acid in chlorination of toluene may cause decay of building and structure. 2008) Furthermore. thereby reducing the flexibility of demand for our benzaldehyde product. Considering the aforementioned factors.60 3) Oxidation of Benzyl Alcohol 2899. Firstly. Furthermore. (Horizon. 2011). which is harmful to aquatic life if leaked. Sodium hydroxide is very hazardous in case of skin contact (Sciencelab. it’s relatively the most environmental friendly process.Safety All chemicals involved in the reaction are combustible. oxidation of alcohol employs Sodium Hydroxide. Benzaldehyde produced from chlorination process doesn’t conform to food grade quality. the by-product of the Chlorination process. by virtue of raising the pH of aquatic environment. 5|Page . Secondly. Environmental Impact Sodium hydroxide. 2010). which may potentially lead to emission of poisonous chlorine. et al.0 Reaction Path Selection Reaction Path Gross Profit ($/tonne) 1) Liquid Phase Oxidation of Toluene 3197. Liquid phase oxidation of toluene. Furthermore. et al. liquid phase oxidation of toluene is deemed to be the most appropriate reaction pathway for large-scale benzaldehyde manufacture. by producing only minor emissions of Carbon Monoxide and Carbon Dioxide. is very toxic to aquatic life. liquid phase oxidation of toluene exhibits highest economy potential as shown in Table 4. 2004) 3. the 68 % selectivity of benzaldehyde significantly exceeds that achieved in oxidation of benzyl alcohol whilst roughly maintaining the same single-pass conversion[18%]. Hence. (Chaudhari. Conversely. Hydrochloric Acid may potentially sell at depressed prices if there’s abundant supply of Hydrochloric acid in our petrochemical complex..90 2) Chlorination of Toluene coupled with Hydrolysis of Benzal Chloride 2466. Moreover. Lastly. 2010) Higher capital and maintenance cost are required by the chlorination process in order to combat corrosiveness. avoids substantial emissions of pollutant residues.(Seider.

2008) A direct distillation sequence was used to recover the products as it’s generally considered to be the most desirable sequence. 179°C and 249°C) are widely spread at atmospheric pressure..The Benzaldehyde recovered is 98. 2008) Since the reactor effluent is distributed between liquid and vapour phases.2003) These impurities have been removed by treating the impure benzaldehyde simultaneously with water and zinc powder followed by distillation. The vapours of unconverted Oxygen and inert Nitrogen.6% pure. (Ullmann. the Arrhenius graph couldn’t be used to ascertain the favourable operating temperature range. C.W. used in this study. et al. the substantial amount of inert Nitrogen absorbs the heat generated by the exothermic oxidation reaction. aren’t recycled as recycle costs aren’t economically viable considering that air is free of charge.(Opgrande. Catalyst is recovered for recycle by means of solvent extraction of the bottoms product of the last distillation tower (Chaudhari. 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. relied upon in this study. Owing to unavailability of published kinetics data for the catalyst. it wasn’t selected since the single-pass conversion was limited to only 10% (Chaudhari. collected by vapour recovery system. However. Benzaldehyde produced from liquid oxidation of Toluene often contains minor odiferous impurities that discolour the product and are difficult to remove by distillation. Instead. 2004) 6|Page . 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..4°C and 212°C . Slightly higher than atmospheric pressures. 2008) Moreover. 76% Benzaledhyde selectivity was also reported.. (Chaudhari.J. The difficult separation of separating the relatively low output of Benzyl Alcohol and Benzyl acetate. Air has been provided in excess in order to facilitate recycled Toluene to be completely consumed. 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. Air is selected as all industrial processes employing liquid-phase oxidation of Toluene use Air. in order to avoid vacuum operation. partial condensation has been used after the reactor as liquid is easier to separate than vapour. which have boiling points of 205. wasn’t pursued owing to the capital-intensive nature. et al..0 Process Synthesis The oxidation agent can theoretically be either pure Oxygen or Air. 2008).8°C. which exceeds the industrial specification of 98. were used in distillation columns as the boiling points of Toluene.4. et al. (Jongsma. thereby maintaining the reactor effluent temperature at a mild temperature of 135. Since the patent.0%. Benzaldehyde and Benzoic Acid(110°C.

300C 735000Kg/h V-02 C-02 44.8 C 2170Kpa 0 To Stack E-01 E-02 E-03 101Kpa C-01 C-03 1200C 2170Kpa 44.970C 2158Kpa E-05 135.60C 122Kpa 9388kg/h CCompressors HE.30C 118Kpa 40440kg/h D-01 Heat in R-03 300C 6336kg/h E-09 Heat in 256.970C 120Kpa E-12 Benzoic Acid Heated Storage Tank CATALYST RECOVERY BY LLE D-03 Benzaldehyde Storage Under Nitrogen Blanket E-08 30 C 40440kg/h F-02 0 E-07 Heat in 184.90C 118Kpa 1608kg/h P-07 E-11 Toluene Storage 30 C 2172Kpa 61260kg/h 0 44.BENZALDEHYDE: LIQUID PHASE OXIDATION OF TOLUENE Air 101.970C 2158Kpa 101.Heater RReboiler ECooler PPump DDistillation Column FFlash Drum VValve D-01 Toluene Column D-02 Benzaldehyde Column D-03 Benzoic Acid Column .3Kpa.8 C 118Kpa 6336kg/h P-02 0 115.970C 2158Kpa 25660kg/h V-01 Impurities 300C 3051kg/h By Products Storage 1200C 2172Kpa 61260kg/h HE-01 Reactor at 1200C and 2170Kpa F-01 209.3Kpa 21200kg/h 49830kg/h To Stack 300 C 40440kg/h E-06 P-01 Treatment to remove impurities causing discoloration before distillation V-03 44.60C 120Kpa 49830kg/h HE-02 LEGEND Heat out 300C 1608kg/h E-10 R-01 Heat out P-06 P-03 193.60C 120Kpa 1608kg/h P-04 Heat out 228.40C 120Kpa 3051kg/h P-05 R-02 D-02 110.

To Stack too QCool1 Air 1 Inter Cooler Compressor 2 QCool2 4 Inter Cooler 2 Qcomp3 QComp2 K-100 55 Inter Cooler 3 QCool3 3 Air to atmosphere Pressurised Air Catalyst Recovery Reactor Products Cooler 1 6 To Valve 1 Flash Flash Drum Q Cooler VLV-102 to stack Qcond V-100 Comp QComp-1 2 Toluene and Air Condenser Recyle toluene To recycle Impurities E-01 10 7 Treatment of impurities causing discoloration before distillation Toluene Column Bottoms Benzaldehyde HE-01 HE-02 Benzaldehyde to storage Cooler 2 Heat in E-02 BZol and Bacetate Heat in 2 Benzaldehyde Column By Products HE-03 E-102 To Storage Cooler 3 Make-up Toluene Pump 1 QHeat 1 8 Toluene MIX-100 QP-1 Pressurised Toluene Heater 1 Toluene to Reactor gdfgd Valve 2 9 E-103 Benzoic Acid Column Heat in 3 Benzoic acid BZoic and Catalyst Cooler 4 Liquid Liquid Separation Benzoic Acid to storage recycle Toluene R RCY-1 Mon Oct 24 21:18:11 2011 Case: H:\PSD\PSD CW\PSD COMPLETED SIMULATION GROUP 12.HSC Flowsheet: Case (Main) .

0 530.120e+004 24.9 8.8 2170 2.0 24.126e+004 70.71 6336 6.20 5.619e+004 7.0000 135.0000 115.126e+004 70.566e+004 7.385e+005 Bottoms 0.2703 -5.0000 30.0 446.00 101.101e+007 9 0.548e+004 7.279e+004 BZoic and Catalyst 0.701e+006 6 0.69 101.92 2172 667.048e+006 3 1.9 2.40 1.0 2.9798 44.046 -9.548e+004 7.17 1608 1.0000 228.9 118.0 10.350e+005 849.0 2.37 3.571e+007 1 1.7 120.2 6.0 446.37 9.0000 0.0000 0.239e+006 Toluene and Air 1.8 4.0000 204.00 120.0 13.0000 30.350e+005 849.00 120.350e+005 849.0000 30.00 108.00 108.983e+004 55.272e+006 55 1.7 1.0000 Toluene 0.0000 120.5 -2.00 101.0 59.0000 120.6 122.0000 120.HSC Flowsheet: Case (Main) .9 2.350e+005 849.0 83.0000 30.00 2168 2.083e+006 Toluene to Reactor 0.00 118.044e+004 46.86 1443 1.7 6.372 -3.963e+005 917.963e+005 917.9 -9.0000 30.86 1443 1.2 4.0 530.963e+005 917.0 2170 2.0 10.101e+006 Impurities 1.6 2158 530.0 0.5 -2.00 118.37 2.00 108.0167 30.834e+007 To Stack too 1.548e+004 7.701e+006 Products 1.0000 184.6 2158 0.0 276.350e+005 849.350e+005 849.9 -9.0000 306.1 2.126e+004 70.74 9388 8.082e+006 Catalyst Recovery 0.3 230.0000 209.71 6336 6.0 4.00 120.7 2.03 3051 2.97 2158 2.7 7.7 1.029e+006 Benzaldehyde to storage 0.7 3.9798 45.0698 110.548e+004 7.547e+006 Air to atmosphere Vapour Fraction Temperature Pressure Molar Flow Mass Flow Liquid Volume Flow Heat Flow C kPa kgmole/h kg/h m3/h kJ/h 10 Vapour Fraction Temperature Pressure Molar Flow Mass Flow Liquid Volume Flow Heat Flow C kPa kgmole/h kg/h m3/h kJ/h 0.006e+004 46.899 -1.936e+007 recycle Toluene 0.021e+004 46.0000 30.438 231.0 438.039e+008 Make-up Toluene 0.481 -4.0 13.481 -4.066e+006 To Storage 0.3 667.0 2170 667.0 4.0000 120.0 7.0000 256.0000 30.025e+006 2 1.0000 30.5 120.924e+008 Pressurised Air 1.0000 Benzaldehyde 1.47 2.481 -4.0000 31.3 118.0000 0.0 835.051e+007 to stack 1.2 4.548e+004 7.0000 40.40 8.044e+004 46.2 837.372 -2.2 6.37 9.3 2.731e+006 BZol and Bacetate 1.167e+006 Benzoic Acid to storage 0.0000 193.619e+004 7.0000 163.853 -6.17 1608 1.983e+004 55.364e+006 To Flash 0.640e+006 Recyle toluene 0.00 108.566e+004 7.0 13.983e+004 55.935e+006 By Products 0.0000 30.00 101.37 9.6 120.40 8.6 2158 530.983e+004 55.0 4.0000 30.0000 0.0000 44.0 437.47 5.4 120.8 118.0 4.239e+006 Benzoic acid 0.0000 204.0000 30.2 6.731e+006 Mon Oct 24 21:22:19 2011 Case: H:\PSD\PSD CW\PSD COMPLETED SIMULATION GROUP 12.0000 204.3 2.Material Streams Air Vapour Fraction Temperature Pressure Molar Flow Mass Flow Liquid Volume Flow Heat Flow C kPa kgmole/h kg/h m3/h kJ/h 1.021e+007 8 0.5127 123.548e+004 7.239e+006 Pressurised Toluene 0.769e+007 To recycle 0.1 2172 2.548e+004 7.204e+005 1.935e+006 7 0.2 278.03 5.3 0.7 7.0000 278.0000 0.97 2158 2.0000 0.2 4.0 59.046 -5.464e+005 862.149e+008 4 1.619e+004 7.464e+005 862.17 1608 1.350e+005 849.

0000 0.0058 0.0001 0.0000 0.0249 0.5905 0.7841 0.0000 1 0.2100 0.0001 0.0001 0.0006 0.0249 0.2100 0.0000 0.0001 0.0041 Benzoic Acid to storage 0.0000 7 0.0249 0.0021 0.9999 0.0058 0.0001 0.0019 0.0000 2 0.0000 0.0000 0.0001 0.0000 0.0000 0.0002 0.3040 0.0021 0.0005 0.2043 0.0000 0.0000 Toluene to Reactor 0.1452 0.7093 0.0208 0.7900 0.0000 0.9770 0.0000 0.0000 0.3302 0.0000 Air to atmosphere 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) 10 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) 0.0000 0.0000 0.0058 Benzoic acid 0.0114 0.0033 BZol and Bacetate 0.7900 0.7702 0.0032 0.0000 Products 0.0000 0.0000 0.0005 0.0000 0.2043 0.HSC Flowsheet: Case (Main) .0042 0.0000 0.0000 0.0000 0.0121 0.0000 0.0000 0.0000 0.0000 0.0001 0.0000 Pressurised Air 0.0000 0.7684 0.0000 0.2100 0.7900 0.0000 0.0000 0.0000 0.2043 0.9953 0.9928 0.0088 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0005 0.2100 0.0000 0.0006 0.0000 0.0033 0.0000 0.0000 Pressurised Toluene 0.0249 0.0000 0.7900 0.0000 0.0000 55 0.0000 0.0000 Impurities 0.0001 0.0117 0.9999 0.8229 0.2534 Benzaldehyde 0.9770 0.0000 0.0000 0.0007 0.0208 0.0000 0.7684 0.0000 To Storage 0.0208 0.0000 0.0000 0.0121 0.0000 0.0021 0.0001 0.0041 To recycle 0.0005 0.0000 0.0088 0.0000 0.0000 0.0000 recycle Toluene 0.0002 Mon Oct 24 21:23:56 2011 Case: H:\PSD\PSD CW\PSD COMPLETED SIMULATION GROUP 12.0001 0.0453 0.0000 0.0001 0.0000 0.0000 0.0001 0.0000 0.0000 0.0001 0.0000 0.5482 0.0000 0.0000 0.0114 0.0000 0.0000 0.0000 0.0000 0.9953 0.7900 0.2084 0.0000 0.0000 0.0000 0.0000 0.0005 0.0000 4 0.1573 0.0000 0.0001 0.0121 0.9999 0.0001 0.0000 0.0394 BZoic and Catalyst 0.7900 0.0005 0.0000 0.0002 0.9864 0.0042 0.0000 0.0114 0.0019 0.0000 0.0140 0.0000 0.Compositions Air 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) 0.2670 0.0459 0.0000 Make-up Toluene 1.8229 0.1122 0.0000 0.7900 0.0000 0.0058 Toluene and Air 0.0001 0.0021 0.0014 0.0000 Bottoms 0.0002 6 0.0063 0.1641 0.9864 0.0000 0.2100 0.0023 0.0032 By Products 0.0063 Catalyst Recovery 0.0000 0.0088 0.0002 0.0000 0.3630 0.0000 0.1122 0.0000 0.0000 0.0000 Recyle toluene 0.0000 to stack 0.0000 0.0000 8 0.0000 0.0000 0.0000 0.0005 0.0000 0.0135 0.9953 0.0000 0.0000 0.0000 0.0000 0.8229 0.0208 0.0554 0.0068 Benzaldehyde to storage 0.0001 0.0001 0.2100 0.0025 0.0766 0.0023 0.1122 0.0121 0.0114 0.0000 0.0000 0.0000 0.0117 0.0000 0.0025 0.0007 0.0000 0.0002 0.0000 0.0000 To Stack too 0.0000 0.0000 0.0000 0.0033 Toluene 0.0000 0.2100 0.0068 0.1122 0.0000 0.0001 0.5905 0.0041 To Flash 0.0001 0.0000 0.7841 0.0000 0.0000 9 0.0000 3 0.0135 0.0023 0.9929 0.8229 0.0009 0.0000 0.7684 0.0088 0.3630 0.0000 0.0000 0.2084 0.0000 0.0000 0.0000 0.0459 0.0007 0.9999 0.0963 0.

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