C3 Compounds

KRUSHIT PATEL (15BCH017)

NISHTHA DANGI (15BCH025)
 INTRODUCTION

C3 COMPOUNDS PLAY AND IMPORTANT ROLE IN

PETROLEUM AND PETROCHEMICAL INDUSTRIES.

FEW IMPORTANT C3 COMPOUNDS DISCUSSED ARE

AS FOLLOWS :
1) PROPENE (PROPYLENE) (IN DETAIL)
2) ISOPROPANOL
3) ACETONE
4) ACRYLONITRILE
5) PROPYLENE OXIDE
 PROPENE (PROPYLENE)

PROPENE IS A VERY IMPORTANT BUILDING BLOCK

FOR A LARGE NUMBER OF CHEMICALS, INCLUDING
THE ADDITION POLYMER, POLY(PROPENE).

HOWEVER, UNLIKE ETHENE, PROPENE READILY

UNDERGOES SUBSTITUTION REACTIONS, WHICH
LEAD TO A WIDE RANGE OF IMPORTANT CHEMICALS.
 USES OF PROPYLENE

THE PRINCIPAL USES OF PROPENE ARE TO

PRODUCE:
 POLY(PROPENE) (POLYPROPYLENE)
 PROPENAL (ACROLEIN)
 PROPENONITRILE (ACRYLONITRILE)
 CUMENE ((1-METHYLETHYL)BENZENE
 EPOXYPROPANE (PROPYLENE OXIDE)
 BUTANAL AND BUTANOL, USED AS A SOLVENT
FOR SURFACE COATINGS
USES OF PROPENE WORLDWIDE Reference [1]
ANNUAL PRODUCTION OF
PROPENE

REGION PRODUCTION

WORLDWIDE 94 million tonnes

ASIA PACIFIC 27 million tonnes

EUROPE 15 million tonnes

U.S 13 million tonnes

MIDDLE EAST 7.5 million tonnes

Reference [2]
CHARACTERISTICS OF PROPENE

Reference [3]
 MANUFACTURE OF
PROPENE

TWO MAIN PROCESSES FOR PROPENE

PRODUCTION ARE :

1) STEAM CRACKING OF NAPHTHA

2) CATALYTIC CRACKING OF GAS OIL
Catalytic Cracking of Propane

Increasingly, propane is being catalytically cracked

to form propene, using the same cat cracker as that
used to crack gas oil:

Propane is being obtained in increasingly large

amounts in the US from shale gas extracted
by fracking.
 The MTO (Methanol To
Olefins) Process
ANOTHER PROCESS THAT HAS BEEN DEVELOPED IS
VIA METHANOL, THE MTP (METHANOL TO PROPENE)
PROCESS.

METHANOL CAN BE CONVERTED INTO HIGH PURITY

ETHENE AND PROPENE VIA DIMETHYL
ETHER. METHANOL VAPOUR IS PASSED OVER
ALUMINA AT CA 600 K. AN EQUILIBRIUM MIXTURE OF
METHANOL, DIMETHYL ETHER AND STEAM IS
PRODUCED, CONTAINING ABOUT 25% METHANOL:
This mixture of gases is then passed over a bed of a zeolite in a
form that encourages high selectivity towards alkenes with
numbers of carbon atoms from 2 to 8.

However, by using a zeolite treated with acid, almost all the

alkene produced is propene.

The propene is purified by cooling it to a liquid and then

subjecting the liquid to fractional distillation.

This is a similar process to that used to make hydrocarbons

used in gasoline, the MTG (Methanol to Gasoline) process.
Production of Propene from
Ethenes and Butenes

BIO-BASED ETHENE CAN BE OBTAINED

BY DEHYDRATION OF BIOETHANOL
USING A SILICA/ALUMINA OR ALUMINA
CATALYST.
The dimerization of ethene to but-1-ene is carried out by passing
heated ethene over a zeolite impregnated with a transition metal
complex. A variety of complexes of rhodium, titanium and other
metals are used:

A mixture of ethene and butene is then heated and passed over a

solid catalyst based on organic compounds of molybdenum(IV) and
tungsten(IV) (the Schrock catalysts) and organo-ruthenium (II)
compounds (the Grubbs’ catalysts), in a fixed-bed reactor.
 ISOPROPANOL

REACTIONS INVOLVED

1. SULFATION: CH3CHCH2 + H2SO4  (CH3)2CH(OSO3H) (ISOPROPYL

ACID SULPHATE)
2. HYDROLYSIS: ISOPROPYL SULPHATE + H2O  ISOPROPANOL +
SULFURIC ACID
3. THUS SULPHURIC ACID IS REGENERATED IN THE PROCESS
4. SIDE REACTION: DISIOPROPYL SULPHATE + H2O  DI-ISOPROPYL
ETHER + SULPHURIC ACID
5. THEREFORE, THE PRIMARY REACTION IS A GAS LIQUID REACTION
IN WHICH PROPYLENE IS ABSORBED INTO A TRAY TOWER FED
WITH SULPHURIC ACID.
6. OPERATING CONDITIONS: ROOM TEMPERATURE BUT 20–25 ATMS
PRESSURE
7. REACTION IS HIGHLY EXOTHERMIC
 PFD for Isopropanol

*Process description
is in notes.
 USES OF ISOPROPANOL

THERE MAY BE MANY USES OF ISO-PROPANOL,

INDUSTRIAL AS WELL AS COMMON USES.

IT FINDS USE IN PHARMACEUTICAL APPLICATIONS

BECAUSE OF THE LOW TOXICITY OF ANY
RESIDUES.

ISOPROPANOL IS ALSO USED AS A CHEMICAL

INTERMEDIATE IN SOME INDUSTRIAL PROCESSES.
IT IS ALSO USED AS A GASOLINE ADDITIVE.
 ACETONE

REACTIONS INVOLVED

1. DEHYDROGENATION OF ISOPROPANOL
2. ISOPROPANOL À ACETONE + H2
3. REACTION PRESSURE: 3 – 4 ATMS
4. REACTION TEMPERATURE: 400 – 500 OC
5. COPPER CATALYST ON POROUS CARRIER IS
USED
6. VAPOR PHASE REACTION
*Process description
is in notes. PFD OF ACETONE
 USES OF ACETONE

ACEONE IS USED AS A POLAR, APROTIC SOLVENT IN A

VARIETY OF ORGANIC REACTIONS.

ONE IMPORTANT PROPERTY FOR WHICH IT IS USED

AS LABORATORY SOLVENT IS BECAUSE DOES NOT
FORM AN AZEOTROPE WITH WATER.

ACETONE IS ALSO USED IN VARIOUS MEDICAL AND

COSMETIC APPLICATIONS.

IT ALSO FORMS AN IMPORTANT COMPONENT IN FOOD

ADDITIVES AND FOOD PACKAGING.
 ACRYLONITRILE

REACTION INVOLVED

1. C3H6 + NH3 + O2 C3H3N + H2O -

2. THE REACTION IS EXOTHERMIC
3. STOICHIOMETRIC RATIO: C3H6 : NH3 : O2 = 1:1:1.5
4. OPERATING CONDITIONS: 1.5 – 3 ATMS PRESSURE
AND 400 – 500OC
5. BY PRODUCTS: ACETONITRILE AND HYDROGEN
CYANIDE FROM SIDE REACTIONS
6. CATALYST: MO-BI CATALYST
 PFD OF ACRYLONITRILE
*Process description
is in notes.
 EPOXYPROPENE
(PROPYLENE OXIDE)

THERE ARE MAINLY THREE METHODS OF PRODUCTION

OF PROPYLENE OXIDE.

1) BY REACTING PROPENE WITH A HYDROPEROXIDE

SUCH 1,1-DIMETHYLETHYL HYDROPEROXIDE
PROPENE IS PASSED INTO LIQUID 1,1-
DIMETHYLETHYL HYDROPEROXIDE UNDER
PRESSURE AT ABOUT 400 K WITH A SOLUBLE
MOLYBDENUM SALT AS CATALYST:
2) By reacting propene with an aqueous solution of chlorine to form a
mixture of 1-chloropropan-2-ol (90%) and 2-chloropropan-1-ol
(10%). Epoxypropane (propylene oxide) forms on addition of a
solution of either sodium hydroxide or calcium hydroxide

3) By reacting propene with hydrogen peroxide. New plants have been

built, adjacent to the plants producing propene, to manufacture large
quantities of hydrogen peroxide. The peroxide reacts directly with
propene:
 REFERENCES

[1] Data for 2015, J S Plotkin The Propylene Quandary, American Chemical Society, 2016

[2] Data from:

1. Data for 2015, J S Plotkin, The Propylene Quandary, American Chemical Society,
2016
2. Estimated data for 2014, Global Petrochemical Overview: Changing Olefins Markets,
Nexant and ChemVision, 2014
3. 2015 Guide to Business of Chemistry, American Chemical Council, 2016
4. Data for 2015, Petrochemicals Europe

[3]
http://www.inventec.dehon.com/documents/pdf/2dff4a2d19083524eab0cc65856a4896.pdf

[4] http://www.essentialchemicalindustry.org/chemicals/propene.html

[5] https://pubchem.ncbi.nlm.nih.gov/compound/Propene#section=Density

[6] NPTEL – Chemical – Chemical Technology II

 THANK YOU

Note :- MSDS of the Compounds discussed are attached with this ppt.