Propylene Oxide

Propylene Glycol[CH
3
CHOH-CH
2
OH]
Propylene Glycol Mono Methyl Ether[CH
3
CH
2
OCH
2
CHOHCH
3
]
Isopropyl Alcohol [CH
3
-CH(OH)CH
3
]
Acetone [CH
3
COCH
3
]
Acrylonitrile[CH
2
=CHCN]
Cumene
Methyl Methacrylate(MMA)-[CH
2
= C(CH
3
)COOCH
3
]
Butyraldehydes and Butanols
2-Ethyl hexanol [CH
3
CH
2
CH
2
CH
2
-CH(CH
2
CH
3
).CH
2
OH]
Methyl Iso Butyl Ketone (MIBK)-[CH
3
COCH
2
CH(CH
3
)
2
]
Diacetone Alcohol [CH
3
COCH
2
C(CH
3
)
2
OH]
Isophorone
Propylene Carbonate [C
3
H
6
CO
3
]
Allyl Chloride [CH
2
=CHCH
2
Cl]
Epichlorohydrin
Acrylic Acid [CH
2
= CHCOOH]
Acrylamide [CH
2
=CHCONH
2
]
Propylene Oxide
Propylene oxide is an organic compound with the
molecular formula CH
3
CHCH
2
O. This
colourless volatile liquid is produced on a large scale
industrially, its major application being its use for the
production of polyether-polyols for use in
making polyurethane plastics. It is chiral epoxide,
although it commonly used as a racemic mixture.
Uses
Between 60 and 70% of all propylene
oxide is converted to polyether
polyols for the production
of polyurethane plastics.

About 20% of
propylene oxide is hydrolyzed into
propylene glycol, via a process which is
accelerated by acid or base catalysis.
Other major products are polypropylene
glycol, propylene glycol ethers,
and propylene carbonate.
Propylene Oxide Process T echnology
Two major process

1. Propylene Chlorohydrin process

2. Epoxidation by peroxide
Propylene Chlorohydrin process
In this process formation of Propylene Chlorohydrin from the
reaction between Hypochlorous acid and Propylene (Fig)

The Propylene Chlorohydrin is epoxidized to Propylene oxide by a
10% solution of milk of lime or NaOH
Byproducts

1,2-dichloropropane and chlorinated diisopropylether



Disadvantages and Economic Drawbacks

Use of costly chlorine
Production of weak CaCl
2

byproduct
Corrosion problem due to Chlorine handling


Epoxidation by peroxide

In this process, Propylene and peracetic acid are reacted in a series of three specially
designed reactors at 50-80
0
and 90-120MPa pressure.


The reaction products are fed to the stripper where a mixture propylene and Propylene
Oxide are obtained as top product while a mixture of ethyl acetate and acetic acid is
obtained as bottom product.

Both mixtures are fed to two separate columns where separation of propylene oxide,
Ethyl acetate, acetic acid and heavy end takes place.
Propylene Glycol[CH
3
CHOH-CH
2
OH]
Propylene glycol, also called 1,2-propanediol or propane-1,2-diol, is an organic
compound (a diol or double alcohol) with formula C
3
H
8
O
2
or HO-CH
2
-CHOH-CH
3
. It is a
colorless, nearly odorless, clear, viscous liquid with a faintly sweet taste, hygroscopic and
miscible with water, acetone, and chloroform.
Structure and properties

Propylene glycol is a clear, colorless and hygroscopic liquid. Propylene glycol contains
an asymmetrical carbon atom, so it exists in two stereoisomers. The commercial
product is a racemic mixture. Pure optical isomers can be obtained by hydration of
optically pure propylene oxide.

Propylene glycol is a component in newer automotive antifreezes and de-icers used at
airports. Like ethylene glycol, the freezing point of water is depressed when mixed with
propylene glycol due to increased opportunity for hydrogen bonding.


Solvent in the flavor concentrate and fragrance industry, an excipient in elixirs and
pharmaceuticals, and a coupling agent in sunscreens, shampoos, shaving creams
and other personal care products
Wetting agent for natural gums to simplify compounding
Humectant, preservative and stabilizer in diverse applications.

Industrial grade:
Raw material to produce high-performance unsaturated polyester resins (UPR)
used for marine construction, gel coats, sheet molding compounds and synthetic
marble castings
Chemical intermediate in the production of resins for paints and varnishes
Solutions with water to make antifreeze, heat-transfer fluids and aircraft and
runway deicing fluids
Solvent in printing inks
Solvent and enzyme stabilizer in laundry detergents
Stabilizer in hydraulic fluids
Plasticizer to improve the processability of plastics
Uses of Propylene glycol
Process Technology

Process consists of three steps.
Reaction of propylene oxide with water
Concentration of reaction product from hydration stage
Distillation for separation of mono propylene glycol, dipropylene glycol
in a series of distillation columns

Propylene Glycol Mono Methyl
Ether[CH
3
CH
2
OCH
2
CHOHCH
3
]
It is produced by reaction of Propylene oxide with methanol
Uses:

Used as solvent for cellulose
Acrylics
Dyes
Inks
Stains and for solvent sealing of cellophanes.
Isopropyl Alcohol [CH
3
-CH(OH)CH
3
]
Isopropyl alcohol (also isopropanol, propan-2-ol, 2-propanol, rubbing alcohol or the
abbreviation IPA) is a common name for a chemical compound with the molecular
formula C
3
H
8
O. It is a colorless, flammable chemical compound with a strong odor. It is the
simplest example of a secondary alcohol, where the alcohol carbon is attached to two other
carbons sometimes shown as (CH
3
)
2
CHOH. It is a structural isomer of propanol.
Properties

Isopropyl alcohol is miscible in water, alcohol, ether and
chloroform. It will dissolve ethyl cellulose, polyvinyl
butyral, many oils, alkaloids, gums and natural resins.

It is
insoluble in salt solutions.

Isopropyl alcohol forms an azeotrope with water, which
gives a boiling point of 80.37
o
C and a composition of 87.7
wt% (91 vol%) isopropyl alcohol. Water-isopropyl alcohol
mixtures have depressed melting points. It has a slightly
bitter taste, and is not safe to drink.

Isopropyl alcohol becomes increasingly viscous with
decreasing temperature. At temperatures below -70 C
Isopropyl alcohol resembles maple syrup in viscosity.
Process Technology
Two industrial process can be used to manufacture isopropyl alcohol
1. Sulphation of propylene followed by hydrolysis of propylene sulphates
2. Direct hydration of propylene to isopropyl alcohol
Sulphation of propylene followed by hydrolysis of propylene sulphates

It is reaction of H
2
SO
4
and Propylene in gas phase at ambient temp and 2-3 Mpa
pressure.

In the second step, isopropyl acid sulphate is hydrolyzed by reducing concentration
by addition of water or steam






Direct hydration of propylene to isopropyl alcohol
Acetone [CH
3
COCH
3
]
Acetone (systematically named propanone) is the organic compound with
the formula (CH
3
)
2
CO. It is a colorless, mobile, flammable liquid, and is
the simplest ketone.
Acetone is miscible with water and serves as an important solvent in its
own right, typically as the solvent of choice for cleaning purposes in the
laboratory.
About 6.7 million tonnes were produced worldwide in 2010, mainly for
use as a solvent and production of methyl methacrylate and bisphenol.
Familiar household uses of acetone are as the active ingredient in nail
polish remover and as paint thinner.
Acetone is produced and disposed of in the human body through normal
metabolic processes. It is normally present in blood and urine. People
with diabetes produce it in larger amounts. Reproductive toxicity tests
show that it has low potential to cause reproductive problems. Due to
the higher energy requirements in pregnant women, nursing mothers and
children, they have higher levels of acetone.
Production
In 2010, the worldwide production capacity for acetone was estimated at 6.7 million tonnes
per year. With 1.56 million tonnes per year, the United States had the highest production
capacity,

followed by Taiwan and mainland China. The largest producer of acetone is INEOS
Phenol, owning 17% of the world's capacity, with also significant capacity (78%)
by Mitsui, Sunoco and Shell in 2010.

INEOS Phenol also owns the world's largest production
site (420,000 tonnes/annum) in Beveren (Belgium). Spot price of acetone in summer 2011
was 11001250 USD/tonne in the United States.
Current method
Acetone is produced directly or indirectly from propylene. Approximately 83% of acetone is
produced via the cumene process,

as a result, acetone production is tied to phenol
production. In the cumene process, benzene is alkylated with propylene to produce cumene,
which is oxidized by air to produce phenol and acetone:
Other processes involve the direct oxidation of propylene (Wacker-Hoechst process), or
the hydration of propylene to give 2-propanol, which is oxidized to acetone.

Acetone by Catalytic Dehydrogenation of Isopropyl Alcohol
Isopropyl Alcohol

By Liquid phase dehydration at 150
0
C in the presence of Raney nickel Catalyst
or
- By Vapor phase dehydration using copper-zinc Catalyst at 400-500
0

or
- Over a ZnO Catalyst at about 380
0
C.



Isopropanol feed is preheated by heat exchanger then it is dehydrogenated at 380
0
C
and 0.2 Mpa in a Multitubular reactor containing ZnO catalyst promoted with Zirconium
oxide.

The reactor product from the reactor containing Acetone, isopropyl alcohol and hydrogen
is passed to an absorber and then fed to a series of distillation columns where seperation
of Acetone from isopropyl alcohol takes place

Acrylonitrile[CH
2
=CHCN]
Acrylonitrile is a chemical compound with the formula C
3
H
3
N. This colorless
liquid often appears yellow due to impurities. It is an important monomer for
the manufacture of useful plastics such as polyacrylonitrile. In terms of
its molecular structure, it consists of a vinyl group linked to a nitrile.
Pathways of exposure include emissions, auto exhaust, and cigarette smoke
that can expose the human subject directly if they inhale or smoke. Routes
of exposure include inhalation, oral, and occasional dermal routes from
volunteer humans and rat studies.
Uses
Acrylonitrile is used principally as a monomer to prepare polyacrylonitrile,
a homopolymer, or several important copolymers, such as styrene-
acrylonitrile (SAN), acrylonitrile butadiene styrene (ABS), acrylonitrile
styrene acrylate (ASA), and other synthetic rubbers such as acrylonitrile
butadiene (NBR). Dimerization of acrylonitrile affords adiponitrile, used in
the synthesis of certain polyamides. Small amounts are also used as
a fumigant. Acrylonitrile and derivatives, such as 2-chloro-acrylonitrile,
are dienophiles in Diels-Alder reactions. Acrylonitrile is also a precursor in
the industrial manufacture of acrylamide and acrylic acid.

Production

Most industrial acrylonitrile is produced by catalytic ammoxidation of propene:
2CH
3
-CH=CH
2
+ 2NH
3
+ 3O
2
2CH
2
=CH-CN + 6H
2
O