Chemical Engineering

Cooper Union for the Advancement of Science and Art

Summer Research Internship Program, Summer 2013

Professor Benjamin Davis

PEEKPMMA KEVLARPTFEPLAPCPOM

POLYETHER ETHER KETONE

Rabia Akhtar and Ozzy Khan

HISTORY MARKETS

Industrial: 39%Electronics: 24%Transport: 26%Medical: 11%

The percentage share of world consumption of Victrex PEEK by sector for the year 2012.

PROPERTIES AND USES

CHEMISTRY AND RAW MATERIALS

PEEK

Hydro-quinone

Arbutin

DFBP

DADM

Aniline

Nitrobenzene

Benzene

Petroleum

Nitric acid

Nitrogen Dioxide H2O

Formaldehyde

Methanol

CO2 H2

Sodium nitrate Hydrogen fluoride

SAFETY AND DISPOSAL

REACTOR DESIGN

Time: 41.7 days/batchBatch size: 3750 kg Spools per batch: 4,650 Spools per day: 100 Spool size: 250’ 1” PEEK electrical sleeving

Tank Size: 3,400 L Temperature: 90ºC

Polymethyl Methacrylate: PMMA

Saijah WilliamsMia Rodie

History and Markets• Discovered in 1877 by Fittig

and Paul

Uses and Properties

1972 Olympic Stadium- Munich, Germany

(pontiacgrandprix.net)

Edge-lighting.com

Headlights made of PMMA

Lighting Applications of PMMA LG LCD television

Polymer Chemistry• PMMA is made of methyl methacrylate. PMMA is most commonly polymerized

through free radical polymerization. • The application of PMMA traces back to the type of polymerization used.

Type of Polymerization Application

Bulk Plexiglas®

Solution Adhesives, paint resins

Suspension PMMA beads

Emulsion Paper coating agents, paper processing agents, textile binders

Raw Materials and Production Process

Hydrogen Cyanide

AcetoneMethyl formate

Methyl methacrylate

methyl a-hydroxyisobutyric

Methyl formate

a-hydroxyisobutyric

acid amide

Hydration of acetonecyanhydrin

Acetone

Prussic acid

Reactor Design

• Goal: 100 sheets of Plexiglas® per day• Amount of PMMA per year: 800 metric

tons• Amount of time per batch: 5.6 minutes

Equation 1

Variable Meaning

Ki, Kp, Kt Rate constants

p Polydispersity

[M] Concentration of monomer

[I] Concentration of initiator

Kevlar

By: Caroline Hunt & Isael Luperon

History and MarketCreated in 1964 by Stephanie KwolekProduced by DuPontFirst commercial use in 1971Mainly produced in USACosts : $12 - $27

Uses & PropertiesAdvantages:

Tensile strength Chemical resistanceStructural rigidityThermal resistanceLightweight

Disadvantages:Absorbs moisturePoor against

compression Poor against UV rays

4 5

6 7

32

Polymer Chemistry

1,4-phenylene-diamine(para-phenylenediamine)Terephthaloyl

Chloride HydrochloricAcid (byproduct)

Poly-para-phenyleneTerephtalamide (Kevlar)

Results of Reactor DesignGoal: 1,000 pairs of Kevlar gloves per dayTotal monomer: 835 molesTotal solvent: 278 molesTotal volume of tank: 150 Liters Time for one reaction: 9.7 seconds

By Sally Kramer

Properties, Uses, and Production of Polytetrafluoroethylene

Dr. Roy Plunkett

History, Discovery, Markets, Demand, Chemical Formula and PricesTeflonRoy Plunkett 1938 DuPont CompanyProduction rate of 900 tons per year in

1948 will grow to 240,000 tons per year by 2017

0123456789

10

2010

2011

PTFE Price as a Function of Time

Year

Pric

e pe

r po

und

($)

Figure 2

Uses and Properties

Polymer Chemistry, Raw Materials, and Production Process

CHCl3 + 2HF CHClF2 + 2HCl (1)

2CHClF2 F2C=CF2 + 2HCl (2)

Fluorspar, water, sulfur, air, natural gas

Ethics and SafetyCarcinogens and birth defects“Fracking” for natural gasDon’t leave an empty Teflon coated

pot or pan over an open flame!If your pan starts tolook like this, throw itaway!

Reactor Design for GasketsGoal: 10,000 Teflon gaskets per day, each

12.947gTen hours per batch, two batches per day24.399 kg

dimethylamine oxide dihydrate

8.714 kg glacial

acetic acid

87.14 kg TFE

26,142 kg water

64.725 kg PTFE

Producing Polylactic Acid By: Kevin Garcia and Janki Tailor

History/ Discovery/ Introduction

O Similar to petroleum based plastics but its biodegradable

O Lactic acid discovered in 1780 by Carl Wilhelm Scheele and PLA discovered in 1932 by Wallace Carothers.

O First official PLA production plant launched in Blaire, Nebraska.

Markets/ Demand/ PricesO Used in fibers, packaging,

and chemical products markets

O Archer Daniels Midland Company, Cargill Inc., and Ecochem

O 6.6 billion lbs. PLA produced annually$6 billion per year

O Global lactic acid production: 40,000 tons per year

Markets and Markets. http://www.marketsandmarkets.com/Market-Reports/polylacticacid-387.html (accessed July 9th, 2013), Global Lactic Acid & Polylactic Acid (PLA) Market by Raw Materials, Types, Applications, and Potential Opportunities (Forecast to 2016).

Uses/ Properties

RigidsThe Potential of Bio-Based Plastics. Steeman, A.

http://bestinpackaging.com/2009/11/30/the-potential-of-bio-based-plastics/ (accessed August 7, 2013).

Food ServicewareExcellent Packaging & Supply (EPS). http://www.packaging-

int.com/suppliers/excellent-packaging-supply-eps.html (accessed August 7, 2013).

Polymer ChemistryO Monomer: L-Lactide

(two lactic acids combined)

Lactic AcidIntech. Jamshidian et al.

http://www.intechopen.com/books/biodegradation-life-of-science/biodegradable-

polymers (accessed July 23, 2013).

L-LactideFuterro.

http://www.futerro.com/products_lactide.html(accessed August 7, 2013).

O Most methods for making PLA are not economically viable

O Methods to synthesis PLA:O Step Growth O Ring Open

Polymerization

Raw Materials/ Production/ Safety

O PLA is eco-friendly, and releases carbon dioxide and methane when it degrades

Corn Starch Fermentation

Lactic Acid PLA Step Growth

Lactide Ring-open Polymerization

Batch DesignO Task: To design a batch

reactor to make these cups

O Goal: Make 10,000 plastic cups/day

O Bulk Reaction

O Catalyst used for reaction: Tin Octoate

Fabri-Kal. http://www.fabri-kal.com/product/greenware-cold-drink-cups/ (accessed August 6, 2013)

Results for our Batch Reactor

OTime per batch: 200 hoursOBatches per year: 44 batches OCups produced per batch: 82,955 cupsOMass of monomer used per cup: 48.65 gOVolume of batch reactor: 3.16 cubic meters

Lactide

PLA

Polycarbonate (PC)

Paulina BabiakAnd

Fradah Gold

Uses and Properties

Polymer Chemistry

ABispheno

l-A

BPhosgen

e

CPolycarbonat

e

Phenyl Groups

Methyl Groups

 

Carbonate

and Safety

Raw MaterialsPolycarbonate (C16H14O3)

Bisphenol-A (C15H16O2 )

Phenol (C6H5O)

Coal Tar C14H18O4ClN5

Coal

Acetone (C3H6O)

Benzene (C6H6)

Petroleum (crude oil)

Propylene (C3H6)

Petroleum Coal Natural Gas

O2

Phosgene (COCl2)

CO

CO2 C

Cl2

$1.75/lb

$0.94/lb $0.74/lb

Phenol NaOH

Phosgene Acetone

Diphenylcarbonate

Bisphenol- A

NaCl

POLYCARBONATE

(Condenser)

Caustic soda

200 L 200ºC 153 min

Process Design for 10 Million CDs

Markets

Polycarbonate Life Cycle

BY O L I V I A KA Z I O R A N D R E E C A N J U A R E Z

POLYOXYMETHYLENE (POM)

INTRODUCTION

• General molecular structure:

H—(—O—CH2—)n—OH

• Discovered during the 1920’s by German chemist Staudinger

• Production began in the U.S. in 1959 when it was finally made thermally stable by chemical company DuPont

MARKETS

Table 2. Percentage share of world POM consumption by market sector, 1999-20025

 1999 2000 2001 2002

Automotive 31.8% 31.8% 32.0% 31.8%

Electrical & Electronics 23.1% 23.3% 23.0% 23.0%

Consumer Products 20.4% 20.3% 20.6% 20.9%

Industrial 17.1% 16.9% 16.4% 16.2%

Others 7.5% 7.6% 8.0% 8.3%

Table 1. POM consumption by region, 1999-2002

 1999 2000 2001 2002

Western Europe 28.8%

29.5%

29.6%

29.6%

North America 23.7%

23.5%

23.0%

23.0%

Japan 15.7%

13.8%

13.9%

13.1%

Remainder of Asia Pacific

31.8%

33.1%

33.5%

34.3%

Source: Platt, D. Engineering and High Performance Plastics Market Report; iSmithers Rapra Publishing, 2003; pp 43

PROPERTIES & USES

• Great mechanical strength, toughness, and resistance to impact electronic and engineering appliances Reduced wear and friction transfer device

• Resistance to moisture and shrink resistance paper

• Can modify toxicity of viruses medicines

Image Source: DuPont Chemical Company

POLYMER CHEMISTRY

formaldehyd

e

+ Distilled H2O

+ Heat Polymerizatio

n + Initiator

Filtration +

Finished Product

Source: Schweitzer, C. E., Macdonald, R. N. and Punderson, J. O. (1959), Thermally stable high molecular weight polyoxymethylenes. J. Appl. Polym. Sci., 1: 158–163.

SAFETY & PRODUCTION

• Injection molding is commonly used to produce POM plastic.

• Formaldehyde (toxic)

• Methanol (toxic)

• POM is generally non-toxic to living things.Sources: DuPont.

http://plastics.dupont.com/plastics/pdflit/americas/delrin/H76836.pdfCenters for Disease Control and Prevention. http://www.cdc.gov/niosh/docs/81-111/

REACTOR DESIGN

To make 1000 POM guitar picks per 15 seconds, you would need:

100 metric tons of POM per year

• Time to make one batch of POM: ~40 hours

• Volume of reactor: 532 liters • Moles of POM: 1445 moles per

literImage Source: Dunlop. http://www.jimdunlop.com/product/delrin

Acknowledgments