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CH0204 Organic Chemical Technology

Lecture  7    

Chapter  2  Synthe1c  Organic  Chemicals  

Balasubramanian  S    Assistant  Professor  (OG)  Department  of  Chemical  Engineering      

1  Balasubramanian  S  

Chapter  2  SYNTHETIC  ORGANIC  CHEMICALS    

       Methane  and  Synthesis  gas    

       Ethylene  and  acetylene  

       Propylene  

       Benzene,  Toluene  and  Xylene  

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2

Overview of topics

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Balasubramanian  S  

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•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

3  Balasubramanian  S  

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Organic  Chemicals  

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Organic  Chemical  is  a  compound  containing  carbon,  oxygen  and  hydrogen  as  principal  cons1tuent  elements.  These  compounds  are  classified  based  on  their  occurrence  as  given  below:      

Organic  Chemicals    

Natural    

Higher  molecular  weight  

e.g.  Hydrolysis  of  fat  or  oil  to  produce  glycerin  of  higher  molecular  weight  

Synthe1c    

Derived  from  naturally  occurring  organic  chemicals  usually  have  low  

molecular  weight    

e.g.  Produc1on  of  formaldehyde  by  oxida1on  of  methane      

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Organic  Chemicals  Classifica1ons  

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Organic  chemicals  based  on  the  presence  of  cyclic  (ring)  compounds  are  classified  as  follows:    

Organic  Compounds    

Alipha1c    Or  Open  Chain  

Open  Chain  or  Acyclic  compounds  

Alicyclic    

Carboxylic  or  ring  compounds  

Aroma1c  

Ring  compounds  containing  atleast  one  

benzene  ring    

Heterocyclic    

Cyclic  (ring)  compounds  containing  other  elements  besides  carbon    

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Organic  Chemicals  Classifica1ons    

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Carbon  forms  large  number  of  compounds  with  hydrogen  and  they  are  collec1vely  known  as  hydrocarbons.  

Hydrocarbons    

Saturated  hydrocarbons     Alkanes  or  Paraffins    

Unsaturated    Hydrocarbons    

Alkenes  or  Olefins  

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Organic  Chemicals,  sources,  process  and  end  product  

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Natural  gas    

Petroleum    

Coal  

Carbon  black    

Acetylene  

Methane    

Ethylene  

Propylene    

Butylene  

Benzene    

Toluene  

Xylene    

Naphthalene    

Coke    

Vinyl  chloride    

Acrylonitrile  

Acetaldehyde  

Methyl  alcohol  

Ethyl  alcohol  

Ethylene  oxide  

Isopropyl  alcohol  

Ethyl  benzene  

Polypropylene  

Butadiene  

Malic  anhydride    

Phenol    

Benzaldehyde  

Benzoic  acid    

Pthalic  anhydride    

Organic  Chemicals,  sources,  process  and  end  product  

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Organic  Chemicals,  sources,  process  and  end  product  

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Synthe1c  Organic  Chemicals  

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•  Derived  from  naturally  occurring  organic  chemicals  such  as  natural  gas,  crude  oil  and  coal.  

•  Have  low  molecular  weight  and  are  categorized  as  follows:  

Synthe1c  organic    chemicals    

Primary  Chemicals     Isolated  first  and  reasonably  pure    

Intermediate    Chemicals    

Derived  from  primary  chemicals;  can  be  u1lized  as  product  but  undergoes  further  chemical  reac1on  to  produce  variety  of  other  chemicals    

End  Chemicals     Undergoes  no  further  chemical  change    

Synthe1c  Organic  Chemicals  

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Synthe1c  Organic  Chemicals  

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Synthe1c  Organic  Chemicals  

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Synthe1c  Organic  Chemicals  

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Synthe1c  Organic  Chemicals-­‐Processes  

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Cracking    Break  down  of  large  hydrocarbon  molecules  into  smaller  molecules  by  heat  or  cataly1c  ac1on.    Thermal  decomposi1on  of  organic  compounds  is  known  as  pyrolysis;  pyrolysis  when  applied  to  alkanes  is  known  as  cracking      Reforming      The  process  whereby  straight-­‐run  gasoline  is  cracked  in  order  to  raise  the  octane  number.          

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Methane  and  Synthesis  gas  

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Methane      Methane  occurs  in  “natural  gas”  and  the  gases  from  oil  wells.    Methane   is   the   principal   product   of   organic   decay   in   swamps   and  marshes.      Sewage   sludge   which   has   been   fermented   by   bacteria   yields   a   gas  containing  about  70%  methane  and  this  is  used  as  liquid  fuel.      Uses      Methane  can  be  used  to  prepare      1.   carbon  black  2.   make  paints  and  printers  ink  3.   rubber  for  motor  tyres  4.   synthesis  gas    

Methane  and  Synthesis  gas  

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Synthesis  gas  (CO,  H2)      Synthesis  gas  is  generally  considered  to  be  a  variable  mixture  of  CO  and  H2  for  synthesis  of  organic  compounds.      Uses      

H2  obtained  from  the  synthesis  gas  has  many  uses  in  hydrogena1on  

The  mixture  (Co  and  H2)  is  used  in  methanol  synthesis    

Used  in  the  synthesis  of  hydrocarbons  by  Fisher-­‐Tropsch  process  

Used  in  the  ammonia  produc1on  

Used  to  produce  ace1c  acid.  

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Produc1on  of  synthesis  gas    

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Synthesis  gas  (CO,  H2)      Synthesis  gas  is  generally  considered  to  be  a  variable  mixture  of  CO  and  H2  for  synthesis  of  organic  compounds.      Methods  of  produc?on    1.  From  petroleum  hydrocarbon  –  Reforming  and  Par1al  Combus1on    2.  From  coal  –  Cracking      Chemical  reac?ons  (Reforming  process)    

CnH2n+1  +  n  H2O        n  CO  +  (2n+1)  H2    n  =  1,  ΔHo  =  +52  kcal;  n  =  2,  ΔHo      =  +238  kcal  (Endothermic)  

Ni  

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Produc1on  of  synthesis  gas    

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Steam  Reforming  of  Petroleum  Hydrocarbons    

Process    

Process  

Desulfurized  hydrocarbon  Fuel  gas  +  Air  

Ni  Catalyst  

Water  

Steam  

CO  +  H2  syngas  

Produc1on  of  synthesis  gas  –  General  Process    

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Catalyst  packed:  Ni  Ver1cal  tube  length:  20  –  25  k  Space  Velocity:  500  –  600/h  Reac1on  :  Endothermic    

Steam  Reforming  of  Hydrocarbons    

Produc1on  of  synthesis  gas  

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Process  Descrip1on  

Produc1on  of  synthesis  gas  

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Process  Descrip1on  

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Produc1on  of  CH4,  C2H2,  C2H4,  C2H6,  C3H6,  C4H8  AND  BTX    

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Steam C

racking of Hydrocarbons

C2H2  C4H8  

C3H6  

Summary  

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Compound     Methane     Ethylene     Acetylene     Propylene  

Formula     CH4    C2H4   C2H2   C3H6  

Structure      

Proper1es   colorless,  odorless  gas,  flammable    

odorless,  colorless  gas  

colorless  gas,  flammable  dis1nc1ve  odor  

Colorless  gas  with    dis1nc1ve  odor  

Uses   In  the  manufacture  of        •  Fuel  •  Chloromethane  •  Dichloromethane          

In  the  manufacture  of        •  Ethylene  

dichloride  •  Vinyl  chloride  •  Ethylene  

dioxide    

In  the  manufacture  of        •  Oxyacetylene  

gas  welding  and  cunng  

•  Polyacetylene  •  Acetaldehyde    

In  the  manufacture  of        •  Propanol  •  Acrylonitrile    •  Acetone      

•  Organic  Chemicals  and  their  classifica1on  based  on  origin  •  Classifica1on  of  Organic  Chemicals  based  on  rings  or  chains  •  Classifica1on  based  on  hydrocarbons  •  Organic  chemicals  sources,  process  and  products  •  Classifica1on  of  synthe1c  organic  chemicals    •  Methane  and  Synthesis  Gas  •  Produc1on  of  synthesis  Gas  •  Produc1on  of  Ethylene,  Acetylene,  Propylene,  Benzene,  

Toluene  and  Xylene  •  Loca1on  of  petrochemical  industries  in  India    

Overview of topics

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Locations – India

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Kochi  Refineries  

Hindustan  Petroleum  Corpora?on,  Vizag    

Mathura  Refinery    

Mangalore  Refinery  

CPCL,  Chennai  

Reliance  Industries  

Essar  Oils  

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References    

1.   Dryden  C.  E,  Outlines  of  Chemical  technoloy  –  for  the  21st    Century,  3rd  edi1on,  East-­‐West  Press  (2004)  

2.     Aus1n  G.  T,  Shreve’s  Chemical  Process  Industries,  5th    edi1on,  Mc  Graw  Hill  Interna1onal  edi1ons  (1984)  

3.   Finar  IL,  Organic  Chemistry  Vol.  1  6th  Edi1on  Pearson                Educa1on  2009  pp.116-­‐117  

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Thank  You