Lab 47c Polystyrene

Abstract In this lab a 2.62% yield of polystyrene monomer weighing 0.218 grams was synthesized from the free radical initiated polymerization of styrene. The distillate was heated under reflux

and then added to a solution of cold methanol in which the polymer then precipitated. The final product was vacuum filtered and allowed to dry.

Purpose The purpose of this experiment is to prepare a pure sample of polystyrene from the peroxide (free radical) initiated polymerization of styrene which was acquired via the acid catalyzed dehydration of 1-phenylethanol. Techniques of acid catalyzed dehydration proceeded via unimolecular elimination (E1) mechanism and was accomplished by reacting 1phenylethanol in the presence of a hydrogen sulfate ion and copper inhibitor. While performing this lab students gain experience and knowledge with the basic chemistry fundamentals involved in preparing modern day plastics which have very much revolutionized the world today. Polystyrene is better known by most as the common name Styrofoam. It is a branched addition polymer which is relatively inexpensive to produce and serves many function uses from disposable drinking cups to light weight aircraft molds. 1

Reactions
OH CH2
KHSO4 Cu

H3C

CH3

CH3

n
O O O

n CH2

+ H2O

Separation Scheme

10g 1-phenylethanol 1g KHSO4 ; .1gCu

Simple Distillation

Acidic Waste

Styrene + H2O Add 3 eq of Tolulene Separatory Funnel Discard Aqueous Waste Organic Layer Styrene + Tolulene Add .1g Benzoyl peroxide

Reflux And Cool Discard Filtrate Crude Polymer Add 200mL Methanol Vacuum Filter Precipitate Purified Polystyrene Waste Methanol

Procedure

The procedure was conducted in accordance with experimental handout Preparation of Polystyrene given in class.

Physical Constants1, REAGENT 1-phenylethanol Molecular Formula C8H10O Molecular Weight (g) 122.16 Density(g/ml) 1.01

Calculations 10.0 g 1-phenylethanol C8H10O (d=1.01 g/mL)(mw=122.16) (10.0g)/122.16 g/mole = .08 moles *Limiting Reagent due to the fact that it is the monomer 1.0 g KHSO4 /136.17 g/mol = .00734 moles KHSO4 0.1 g Cu /63.5g/mol = .00157 moles Cu

A. Limiting Reagent 10.0grams 1-phenylethanol C8H10O (d=1.01 g/mL)(mw=122.16) (10.0g)/122.16 g/mole = .08 moles *Limiting Reagent due to the fact that it is the monomer

B. Theoretical Yield (Limiting moles)(Ratio)(Molecular Weight of Product) (.08 moles 1-phenylethanol) (1:1) (104 g/mole of polystyrene monomer ) = 8.32 grams of C8H8 (polystyrene monomer)

C. Actual Yield and Percent Yield Crude Product Mass = 0.218 grams Percent Yield = (Actual/Theoretical) 100%
4

(0.218/8.32)100 = 2.62 % yield D. Analytical Data The low percent yield was most likely due to the high losses during phase transfers and leaks in the apparatus while distilling and refluxing. The short reflux period might have also contributed to the lower percent yield.

Spectra3 No IR spectra analysis was performed in this experiment.

Citations

1) D.L. Pavia, G. M. Lampman, G. S. Kriz, and R. G. Engel Introduction to Organic Laboratory Techniques: A Small Scale Approach, 3rd Ed., (2011) Brooks/Cole, pp.371-387

2) D.L. Pavia, G. M. Lampman, G. S. Kriz, and R. G. Engel Introduction to Organic Laboratory

Techniques: A Small Scale Approach, 3rd Ed., (2011) Brooks/Cole, pp.865-888

Questions 2.
6

Cl CH3 H3C Cl n

4.
CH3 CH3 H3C CH3 n

5.
F F

Cl n

8.

O HO S O OH OH

CH3
Cu

KHSO4

OH

CH3

CH

CH3

H2O

CH2

+
9. Addition polymer 10. a) aromatic C-H stretches b)alkyl C-H stretches c) C-C stretches of the aromatic ring d)C-H Out of plane bending

H3O

11.
F F CH3 H2C O F F O CH3

12.
H2C Cl n