Propylene Derivatives

5/26/2018 Propylene Derivatives

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Propylene Oxide

Propylene Glycol[CH3CHOH-CH2OH]Propylene Glycol Mono Methyl Ether[CH3CH2OCH2CHOHCH3]Isopropyl Alcohol [CH3-CH(OH)CH3]Acetone [CH3COCH3]Acrylonitrile[CH2=CHCN]

CumeneMethyl Methacrylate(MMA)-[CH2= C(CH3)COOCH3]Butyraldehydes and Butanols2-Ethyl hexanol [CH3CH2CH2CH2-CH(CH2CH3).CH2OH]Methyl Iso Butyl Ketone (MIBK)-[CH3COCH2CH(CH3)2]Diacetone Alcohol [CH3COCH2C(CH3)2OH]

IsophoronePropylene Carbonate [C3H6CO3]Allyl Chloride [CH2=CHCH2Cl]EpichlorohydrinAcrylic Acid [CH2= CHCOOH]Acrylamide [CH2=CHCONH2]


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Propylene OxidePropylene oxide is an organic compound with themolecular formula CH

3CHCH

2O. This

colourless volatile liquid is produced on a large scaleindustrially, its major application being its use for theproduction of polyether-polyols for use inmaking 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 intopropylene glycol, via a process which is

accelerated by acid or base catalysis.

Other major products are polypropylene

glycol, propylene glycol ethers,

and propylene carbonate.
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Propylene Oxide Process T echnology

Two major process

1. Propylene Chlorohydrin process

2. Epoxidation by peroxide


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Propylene Chlorohydrin process

In this process formation of Propylene Chlorohydrin from thereaction between Hypochlorous acid and Propylene (Fig)

The Propylene Chlorohydrin is epoxidized to Propylene oxide by a10% solution of milk of lime or NaOH


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Byproducts

1,2-dichloropropane and chlorinated diisopropylether

Disadvantages and Economic Drawbacks

Use of costly chlorineProduction of weak CaCl2 byproductCorrosion problem due to Chlorine handling


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Epoxidation by peroxide

In this process, Propylene and peracetic acid are reacted in a series of three speciallydesigned reactors at50-800 and 90-120MPa pressure.

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


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Propylene Glycol[CH3CHOH-CH2OH]

Propylene glycol, also called 1,2-propanediolor propane-1,2-diol, is an organic

compound(a diolor double alcohol) with formula C3H8O2or HO-CH2-CHOH-CH3. It is a

colorless, nearly odorless, clear, viscous liquid with a faintly sweet taste, hygroscopicandmisciblewith 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 racemicmixture. 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.
http://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Diolhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Hygroscopichttp://en.wikipedia.org/wiki/Hygroscopichttp://en.wikipedia.org/wiki/Misciblehttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Acetonehttp://en.wikipedia.org/wiki/Chloroformhttp://en.wikipedia.org/wiki/Stereoisomerhttp://en.wikipedia.org/wiki/Racemichttp://en.wikipedia.org/wiki/Propylene_oxidehttp://en.wikipedia.org/wiki/Ethylene_glycolhttp://en.wikipedia.org/wiki/Hydrogen_bondinghttp://en.wikipedia.org/wiki/Hydrogen_bondinghttp://en.wikipedia.org/wiki/Ethylene_glycolhttp://en.wikipedia.org/wiki/Propylene_oxidehttp://en.wikipedia.org/wiki/Racemichttp://en.wikipedia.org/wiki/Stereoisomerhttp://en.wikipedia.org/wiki/Chloroformhttp://en.wikipedia.org/wiki/Acetonehttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Misciblehttp://en.wikipedia.org/wiki/Hygroscopichttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Diolhttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Organic_compound


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Solvent in the flavor concentrate and fragrance industry, an excipientin elixirs and

pharmaceuticals, and a coupling agent in sunscreens, shampoos, shaving creams

and other personal care productsWetting 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 syntheticmarble 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
http://www.dow.com/productsafety/overview/glossary.htmhttp://www.dow.com/productsafety/overview/glossary.htmhttp://www.dow.com/productsafety/overview/glossary.htmhttp://www.dow.com/productsafety/overview/glossary.htm


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Process Technology

Process consists of three steps.Reaction of propylene oxide with waterConcentration of reaction product from hydration stageDistillation for separation of mono propylene glycol, dipropylene glycol

in a series of distillation columns


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Propylene Glycol Mono MethylEther[CH3CH2OCH2CHOHCH3]

It is produced by reaction of Propylene oxide with methanol

Uses:

Used as solvent for cellulose

AcrylicsDyesInksStains and for solvent sealing of cellophanes.


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Isopropyl Alcohol [CH3-CH(OH)CH3]

Isopropyl alcohol(also isopropanol, propan-2-ol, 2-propanol, rubbing alcoholor the

abbreviation IPA) is a common name for a chemical compoundwith the molecular

formulaC3H8O. It is a colorless, flammablechemical compoundwith a strong odor. It is thesimplest example of a secondary alcohol, where the alcoholcarbon is attached to two other

carbons sometimes shown as (CH3)2CHOH. It is a structural isomerof propanol.

Properties

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

insoluble in salt solutions.

Isopropyl alcohol forms an azeotrope with water, whichgives a boiling point of 80.37 oC and a composition of 87.7wt% (91 vol%) isopropyl alcohol. Water-isopropyl alcohol

mixtures have depressed melting points. It has a slightlybitter taste, and is not safe to drink.

Isopropyl alcohol becomes increasingly viscous withdecreasing temperature. At temperatures below -70 C

Isopropyl alcohol resembles maple syrup in viscosity.
http://en.wikipedia.org/wiki/Rubbing_alcoholhttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Molecular_formulahttp://en.wikipedia.org/wiki/Molecular_formulahttp://en.wikipedia.org/wiki/Transparency_and_translucencyhttp://en.wikipedia.org/wiki/Flammablehttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Odorhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Isomerhttp://en.wikipedia.org/wiki/Propan-1-olhttp://en.wikipedia.org/wiki/Propan-1-olhttp://en.wikipedia.org/wiki/Isomerhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Odorhttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Flammablehttp://en.wikipedia.org/wiki/Transparency_and_translucencyhttp://en.wikipedia.org/wiki/Molecular_formulahttp://en.wikipedia.org/wiki/Molecular_formulahttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Rubbing_alcohol


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Process Technology

Two industrial process can be used to manufacture isopropyl alcohol

1. Sulphation of propylene followed by hydrolysis of propylene sulphates2. Direct hydration of propylene to isopropyl alcohol

Sulphation of propylene followed by hydrolysis of propylene sulphates

It is reaction of H2SO4and Propylene in gas phase at ambient temp and 2-3 Mpapressure.

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


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Direct hydration of propylene to isopropyl alcohol


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Acetone [CH3COCH3]

Acetone(systematically named propanone) is the organic compoundwiththe formula(CH3)2CO. It is a colorless, mobile, flammable liquid, and isthe simplest ketone.

Acetone is misciblewith waterand serves as an important solventin itsown right, typically as the solvent of choice for cleaning purposes in the

laboratory. About 6.7 million tonneswere produced worldwide in 2010, mainly for

use as a solvent and production of methyl methacrylateand bisphenol.

Familiar household uses of acetone are as the active ingredient in nailpolish removerand as paint thinner.

Acetone is produced and disposed of in the human body through normalmetabolic processes. It is normally present in blood and urine. Peoplewith diabetesproduce it in larger amounts. Reproductive toxicity testsshow that it has low potential to cause reproductive problems. Due tothe higher energy requirements in pregnant women, nursing mothers andchildren, they have higher levels of acetone.
http://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Chemical_formulahttp://en.wikipedia.org/wiki/Ketonehttp://en.wikipedia.org/wiki/Ketonehttp://en.wikipedia.org/wiki/Ketonehttp://en.wikipedia.org/wiki/Miscibilityhttp://en.wikipedia.org/wiki/Properties_of_waterhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Tonnehttp://en.wikipedia.org/wiki/Methyl_methacrylatehttp://en.wikipedia.org/wiki/Bisphenol_Ahttp://en.wikipedia.org/wiki/Nail_polish_removerhttp://en.wikipedia.org/wiki/Nail_polish_removerhttp://en.wikipedia.org/wiki/Diabeteshttp://en.wikipedia.org/wiki/Diabeteshttp://en.wikipedia.org/wiki/Nail_polish_removerhttp://en.wikipedia.org/wiki/Nail_polish_removerhttp://en.wikipedia.org/wiki/Bisphenol_Ahttp://en.wikipedia.org/wiki/Methyl_methacrylatehttp://en.wikipedia.org/wiki/Methyl_methacrylatehttp://en.wikipedia.org/wiki/Tonnehttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Properties_of_waterhttp://en.wikipedia.org/wiki/Miscibilityhttp://en.wikipedia.org/wiki/Ketonehttp://en.wikipedia.org/wiki/Chemical_formulahttp://en.wikipedia.org/wiki/Organic_compound


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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 Taiwanand mainland China. The largest producer of acetone is INEOS

Phenol, owning 17% of the world's capacity, with also significant capacity (7

8%)

by Mitsui, Sunocoand Shellin 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 phenolproduction. In the cumene process, benzeneis alkylated with propylene to produce cumene,

which is oxidizedby air to produce phenoland acetone:

Other processes involve the direct oxidation of propylene (Wacker-Hoechst process), or

the hydrationof propylene to give 2-propanol, which is oxidized to acetone.
http://en.wikipedia.org/wiki/Taiwanhttp://en.wikipedia.org/wiki/Mainland_Chinahttp://en.wikipedia.org/wiki/INEOS_Phenolhttp://en.wikipedia.org/wiki/INEOS_Phenolhttp://en.wikipedia.org/wiki/Mitsuihttp://en.wikipedia.org/wiki/Sunocohttp://en.wikipedia.org/wiki/Royal_Dutch_Shellhttp://en.wikipedia.org/wiki/Beverenhttp://en.wikipedia.org/wiki/Propylenehttp://en.wikipedia.org/wiki/Cumene_processhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Cumenehttp://en.wikipedia.org/wiki/Oxidationhttp://en.wikipedia.org/wiki/Phenolhttp://en.wikipedia.org/wiki/Wacker-Hoechst_processhttp://en.wikipedia.org/wiki/Hydration_reactionhttp://en.wikipedia.org/wiki/2-propanolhttp://en.wikipedia.org/wiki/2-propanolhttp://en.wikipedia.org/wiki/2-propanolhttp://en.wikipedia.org/wiki/2-propanolhttp://en.wikipedia.org/wiki/Hydration_reactionhttp://en.wikipedia.org/wiki/Wacker-Hoechst_processhttp://en.wikipedia.org/wiki/Wacker-Hoechst_processhttp://en.wikipedia.org/wiki/Wacker-Hoechst_processhttp://en.wikipedia.org/wiki/Phenolhttp://en.wikipedia.org/wiki/Oxidationhttp://en.wikipedia.org/wiki/Cumenehttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Cumene_processhttp://en.wikipedia.org/wiki/Cumene_processhttp://en.wikipedia.org/wiki/Cumene_processhttp://en.wikipedia.org/wiki/Propylenehttp://en.wikipedia.org/wiki/Beverenhttp://en.wikipedia.org/wiki/Royal_Dutch_Shellhttp://en.wikipedia.org/wiki/Sunocohttp://en.wikipedia.org/wiki/Mitsuihttp://en.wikipedia.org/wiki/INEOS_Phenolhttp://en.wikipedia.org/wiki/INEOS_Phenolhttp://en.wikipedia.org/wiki/Mainland_Chinahttp://en.wikipedia.org/wiki/Taiwan


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Acetone by Catalytic Dehydrogenation of Isopropyl Alcohol


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Isopropyl Alcohol

By Liquid phase dehydration at 1500C in the presence of Raney nickel Catalystor

- By Vapor phase dehydration using copper-zinc Catalyst at 400-5000

or

- Over a ZnO Catalyst at about 3800C.

Isopropanol feed is preheated by heat exchanger

then it is dehydrogenated at 3800

Cand 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


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Acrylonitrile[CH2=CHCN]

Acrylonitrileis a chemical compoundwith the formula C3H3N. This colorless

liquid often appears yellow due to impurities. It is an important monomerforthe manufacture of useful plastics such as polyacrylonitrile. In terms ofits molecular structure, it consists of a vinyl group linked to a nitrile.Pathways of exposure include emissions, auto exhaust, and cigarette smokethat can expose the human subject directly if they inhale or smoke. Routesof 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 acrylonitrilebutadiene (NBR). Dimerizationof acrylonitrile affords adiponitrile, used inthe synthesis of certain polyamides. Small amounts are also used asa fumigant. Acrylonitrile and derivatives, such as 2-chloro-acrylonitrile,are dienophiles in Diels-Alder reactions. Acrylonitrile is also a precursor inthe industrial manufacture of acrylamideand acrylic acid.
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Production

Most industrial acrylonitrile is produced by catalyticammoxidationof propene:2CH3-CH=CH2+ 2NH3+ 3O22CH2=CH-CN + 6H2O
http://en.wikipedia.org/wiki/Catalysthttp://en.wikipedia.org/wiki/Ammoxidationhttp://en.wikipedia.org/wiki/Propenehttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Propenehttp://en.wikipedia.org/wiki/Ammoxidationhttp://en.wikipedia.org/wiki/Catalyst


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Documents

Propylene Derivatives