The Production ofThe Production of

Propylene Oxide Propylene Oxide Using Using Cell Liquor Cell Liquor

Meshal Al-RumaidhiMeshal Al-Rumaidhi

Hassan Ghanim Ali Al-Hassan Ghanim Ali Al-Haddad Haddad

Abdulrahman HabibAbdulrahman Habib

Supervised by:

Prof. : Mohammed Fahim Prof. : Mohammed Fahim Eng. : Yousif AliEng. : Yousif Ali

AgendaAgenda IntroductionIntroduction Production RoutesProduction Routes ReactionsReactions Feed Stocks (Raw Material)Feed Stocks (Raw Material) Final ProductFinal Product ThermodynamicsThermodynamics Yield CalculationYield Calculation Process Technology and FlowsheetsProcess Technology and Flowsheets Process Alternatives (Licensors)Process Alternatives (Licensors) Health and Safety IssuesHealth and Safety Issues Uses of Propylene OxideUses of Propylene Oxide World ProductionWorld Production Comparison of PO Production RoutesComparison of PO Production Routes ConclusionConclusion

IntroductionIntroduction

What is What is

Propylene Oxide?Propylene Oxide? Propylene oxide (also known as

PO, methyloxirane, 1.2-epoxypropane) is a significant organic chemical used primary as a reaction intermediate for production of polyether polyols, propylene glycol, alkanolamines (qv), glycol ethers, and many other useful products. It is an important propylene-derived chemical. In the united state, it is estimated that PO is the third largest derivative of propylene.

Cont. IntroductionCont. IntroductionHistory of Propylene Oxide:

The first preparation of PO was reported in wurz’s laboratory in 1860 union carbide started development in 1925, and PO became a leading industrial chemical after World War II when its importance in polyurethanes was recognized.

Production RoutesProduction RoutesThe selection of production routes is

decisively influenced by the application and market potential of co-products, as well as by availability of raw materials and possibilities for byproduct management.

Technologies developed up to this point can be divided into:◦ Chlorohydrin Processes◦ Indirect Oxidation Processes ◦ Direct Oxidation Processes

Cont. Production RoutesCont. Production Routes

ReactionReactionChlorohydrin Reaction:Chlorohydrin Reaction:

Saponification Reaction:Saponification Reaction:

Feed Stocks (Raw Feed Stocks (Raw Materials)Materials)

Raw Materials:Raw Materials:

1) Propylene

2) Chlorine

3) Water

4) Sodium Hydroxide

Final ProductFinal ProductPhysical and Chemical properties for Physical and Chemical properties for

Propylene Oxide (PO):Propylene Oxide (PO):

Propylene oxide is a colorless, highly volatile, very soluble in water, and flammable liquid at room temperature and normal atmospheric pressure.

Physical State LiquidOdor EtherealMolecular Weight 58.08 g/molBoiling Point 34.23 °CMelting Point -111.93 °CFlash Point -37 °C

ThermodynamicsThermodynamics The PO production is consisting of three exothermic

reactions:

Chlorohydrin ReactionChlorohydrin Reaction

Saponification ReactionSaponification Reaction

Yield CalculationYield Calculation

Conversion of Propylene = 97%Selectivity of propylene = 95%Yield = Selectivity * Conversion = 0.97*0.95 = 92.15%

Real yield PO = 89.4%

The calculation yield is approximate to real yield.

Process Technology and Process Technology and FlowsheetsFlowsheets

Design Bases & Assumption

ChlorohydrinationType of reactor Packed columnTemperature & Pressure 40 °C & 60 psiaConversion of Propylene 97%Selectivity to PCH 95 mol%Selectivity to PDC 3.7 mol%Selectivity to DCIPE and other 1.3 mol%

SaponificationType of reactor Tray columnTemperature & Pressure 85 °C & 65

psiaAmount of cell liquor added 1% excess alkaliConversion of PCH 99.9%Selectivity to PO 95 mol%Selectivity to propylene glycol 5 mol%

Process ConditionsProcess Conditions

Chlorohydrination:Chlorohydrination:Type of reactor Packed ColumnsTemperature 40 oCPressure 60 psia

Saponification: Saponification: Type of reactor Tray ColumnTemperature 85 oCPressure 65 psia

Health and Safety IssuesHealth and Safety IssuesFlammability HazardsReactivity HazardsExplosibilityToxicology and Occupational Health

Hazards

Uses of Propylene OxideUses of Propylene Oxide

PO is an important basic chemical intermediate. Virtually all the PO produced is converted into derivatives, often for applications similar to those of ethylene oxide (EO) derivatives.

PO is used primarily to produce polyether polyols, propylene glycols, propylene glycol ethers and, and many other useful products.

Cont.Cont. UsesUses

Cont. UsesCont. Uses

World ProductionWorld Production

Process Alternatives Process Alternatives (Licensors) (Licensors)

PO Using Chlorohydrine Process by Lime.

PO Using Indirect Oxidation Process by Isobutane.

PO Using Indirect Oxidation Process by Ethyl Benzene.

PO by Direct Oxidation.

Reaction Reaction (Chlorohydrine (Chlorohydrine Process by Lime)Process by Lime)

Chlorohydrin Reaction:Chlorohydrin Reaction:

Saponification Reaction:Saponification Reaction:

Process ConditionsProcess Conditions

Chlorohydrination:Chlorohydrination:Type of reactor Packed ColumnsTemperature 49 oCPressure 17 psia

Saponification: Saponification: Type of reactor Tray ColumnTemperature 92 oCPressure 22 psia

Typical arrangement for PO using chlorohydrins process by LimePropylene chlorohydrin reactor; b) Separator; c) Vent gas scrubber; d) Saponifier; e) Partial condenser; f) Cross exchanger; g) Compressor; h) Propylene oxide purification train; i)Drums

Reaction Reaction (Indirect Oxidation (Indirect Oxidation Process by Isobutane)Process by Isobutane)

The main reaction of this processThe main reaction of this process

Process ConditionsProcess Conditions (Indirect Oxidation Process (Indirect Oxidation Process by Isobutane)by Isobutane)

Type of reactor Peroxidation reactorTemperature 120 – 140 oCPressure 25 – 35 barCatalyst not needed

Type of reactor Epoxidation reactorTemperature 110 oCPressure 40 barCatalyst Molybdnum

Flow scheme for PO-tert butyl alcohola) Vent column; b) Lights scrubber; c) PO column; d) tert-butyl alcohol lights column; e) tert-butyl alcohol column

Reaction Reaction (Indirect Oxidation (Indirect Oxidation Process by Ethyl Benzene)Process by Ethyl Benzene)

The main reaction of this processThe main reaction of this process

Process Conditions Process Conditions (Indirect Oxidation Process by (Indirect Oxidation Process by Ethyl Benzene)Ethyl Benzene)

Type of reactor Peroxidation reactor

Temperature 146 oC

Pressure 2 bar

Type of reactor Epoxidation reactor

Temperature 100 oC

Pressure 35 bar

Catalyst Molybdnum

Type of reactor Dehydration reactor

Temperature 270 oC

Pressure 0.35 bar

Catalyst Alumina

Flow scheme for PO-styrene processa) Separator; b) Recycle column; c) Crude PO column; d) Ethylbenzene recycle column

PO by Direct OxidationPO by Direct Oxidation

The Disadvantage of Direct The Disadvantage of Direct Oxidation:Oxidation:

1) Difficult in Controlling Temperature.

2) Several of by-Products.

Comparison of PO Comparison of PO Production Routes:Production Routes:

PO Production 1986 1991 1996

Chlorohydrin process, % 58 55 49

PO/styrene process, % 18 19 24

PO/tert-butyl alcohol process, % 24 26 24

Direct oxidation, % 0 0 2

World PO capacity, 1000 t/a 3300 3900 4900

World PO consumption, 1000t/a 2600 3250 3900

ConclusionConclusionPropylene oxide via Chlorohydrin Processes

Using Cell Liquor is useful technique and has many advantages that our country needed.

We cannot decide if it’s the best method before we studying the costs.