P.1 

OAR Box 1877 

Prepped by Keeia Richards 

Document Number: 

25) ll-B-22 

Docket Number: 

A-90-19 

Printed 12/2/2008 J 0:36:48 AM Sheet 25 of 46 
P.2 

% : 

A-90-19 

ll-B-22 

MEMORANDU M 

TO: Process Vents Docket A-90-19 

FROM: Wanda Floyd 

DATE: November 1990 

SUBJECT: HON NESHAP: Industry Characteristics/Bisphenol 

Attached is a product-process summary (PPS) for the production of Bisphenol A 

via condensation of Phenol and Acetone category. This PPS was developed as part 

of the Industrial Profile project in support of the Hazardous Organic NESHAP 

(HON) regulatory effort. Information in this PPS is used as a basis for 

emissions and cost impact estimates for the HON program. 

Listed below are the key references used in developing the attached PPS. 

"Bisphenol A." In: Mannsville Chemical Products. New York, February, 1988. 

1989 Directory of Chemical Producers. SRI International. California, 

p. 487. 

Kent, James A. Riegel's Handbook of Industrial Chemistry. 7th edition. Van 

Nostrand Reinhold Company, New York, 1974. pp. 814-815. 

Chenier, Philip, Jr. Survey of Industrial Chemistry. John Wiley & Sons, New 

York, 1986. pp. 182-183. 

Weissermel, Klaus and Arpe, Hans-Jurgen. Industrial Organic Chemistry. Verlag 

Chemie, new York, 1978. pp. 314-315. 

"Bisphenol A." In: Chemical Marketing Reporter. New York, July 27, 1987. 

m 

~ 7 ;------- teases 

N wmmt is Dectet (tea „ 

A-90-19 

H-B-252 

— t ^ 

vch/067 

Bispheno 
P.3 

h> 

Preparer: _fj^JloJ^0.L 

n Date: S/A*/1* 

Reviewer: _J_ V 

ADMINISTRATIVE NOTES 

Product-Process Code $0057 A 

Hours spent on this PPS ^-S" 

P-P Name bi'spt^flol k \no* Cer^AtM^akiirt^ of VLIAK^I ^W/^& W 

Incomplete Items (parts of 

form you cannot complete) 

nine # and description) Date Cleared Initials 

_ ftoy\£s— 

siz^ho jjj 

Chemicals missing CAS numbers 

Plant with dt y but; ng County (plant name, dty , state) 

• • S*M. p/^t^ob Usre J Us$t t l 3.2 , 
ypAPreparer: 1rjejL<jeJoe,b. 

Date: £/*A/fa 

Reviewer: ' 

PROOUCT-PROCESS SUMMARY (PPS) 

Chemical Name kispl&Kel A 

Alternate* Chemical Kan* *o Aohx, 

CAS I 70QS1 

Karen FV#^^^^HH H "° ^ ^ • 

CHEMICAL SPECIPIC INFORMATION 

1.0 U.S. Production Ref # J_ , Pg # , Ref Year fe&Jffi 

(Indicate the same reference information for any answers below from a 

different reference) 

.1.1 Unffs of production (circle onelfnjnilons of ~toJ or millions of gallons 

1.2 «* SV Capacity 5/6 

1.3 tj, srUftclty Utilization >U **** ' &* i^ 

1.5 mporti *^fl 

J»6 Exports £ 1 

1.7 Product Price 

* -Mr * TT" * W 

e^**^C 

1.7.1 Average Prica 

1.7.2 OMtf of>rHt T^Mf.**>ffiff y i/qallon " "* 

1.7.3 C^ntOn prtii ~ 

1.8 Comments ^ ^ / r Q 

+U LAY**- <JU~* 5U^*^ fJijAc ,J+~f+&r *.<^< 
P.5 

2.0 Chemical End-Use Ref # ± , Pg # § Re f Yfia r ^ 

Use Percent. 

Wise . ^ 

/i&*c*i-4-' &\fflAMje~- "fvusib&t*-/ <~<yyu&C0?^ /^ttC&oSr-CZ'j 0Lclh44Ctrh~} 
3.0 U.S. Producers Ref I 5 Pg # , Ref Year ±j <°l&Z 

Billions Of Kg or roilHons of gallons 

3.2 Naae, Location, and Capacity 

location, 

Process Used 

(use P-P I) 

102 

IG g 

fV^pertrt" , | )c 

Veer R^rkl, TyL 

P-P 1 

P-P 1 

P-P l 

P-p l 

Total Capacity 5 lo 

^£t? t/-af. proeUccesS og (i+cffLt^A 4 *£*<> /u^o^wJe^cil^ijz, ^hjl^AC 

TJ 

0> 
P.7 

PRODUCT-PROCESS SPECIFIC INFORMATION 

4.0 Potential Product-Processes (P-P) Ref # 5 Pg # ^bJl^ S 

Commercially % Nat'l 

Njig Viable (v/n. Capacity 

P-P 1 biSpktW A ytA, fVtt/W^gcrrm. o£ jk&*#l <**dacelflit: L_ 100 

P-P 2 ; 

P-P 3 

P-P 4 

P-P 5 ; 

P-P 6 

4.1 Documentation of P-Ps Excluded 

P-P not 

Commercially Viable Reasons 

V\er*£, 

4.2 Process described ( , r , 

in tM$ PPS bisptiAA^I A VIA, c^Kgle^SATityrx. or J>UM\ O«*A »<^ W 
P.8 

Air Oxidation Reaction 

Oxidation Reaction 

Alkylation Reaction 

Carbonylation Reaction 

Halogenation Reaction 

Condensation Reaction 

Dehydrogenation Reaction 

Dehydrohalogenation Reaction 

Esterification Reaction 

Hydrogenation Reaction 

Hydrohalogenation Reaction 

Hydroformylation Reaction 

Hydrolysis Reaction 

Nitration Reaction 

Oxyacetylation Reaction 

Oxyhalogenation Reaction 

Sulfonation Reaction 

Catalytic Reformation 

Hydrodimerization Reaction 

Ref I PQ » a/ n « 

Generic Reaction 

4.4 Explain how you selected the reaction type in line 4.3. 

- + ev*t»v t^seri i'n rv$&r<M£*- desc^npfwH' 
P.9 

4.5 Written Description l&r±S+5— ,

 p%* U£SLH& 

d;scHPUofn

t

.

mar9ln' 1nd1Cat e r6ferenCe s an d

 TM* "TMb«" throughout written 

/^^Hk^J. sh-eAc^pi-*^. OASQ NCI 2*4. . S^. /^O/^J S^he y&A_ 

j<A- 2-/2 h>^A4- • -fU prive t c^fhMt^.^ fi^ +i^_ y^cJi ^ 

A**>faus i r fit**. «. yU^-y - *'^ ) fl^te^ Aju^CfTo^-) CJU^U 

+ $ ^^di^f ^ ^f^ { c£ HCI W USV&AS • R^ccn^s.^. (SCI a~^. 

juices? .Ju**{ VJL Aa.e^d^ef. dt^JL 'b^pU^J 4 M JU*pp&? 

A+^MJA, (sa.^uyysh>^ &f iu^ceA^StS^J^ LL* 4> I So T ('*•"**"//& > 
P.10 

5.0 Process Flow Diagram (attach at end of package) 

5.1 Flow Diagram Reference: Ref I __£ , Pg # ft/4 

5.2 Comments on Flow Diagram 

v*.o&e\ pl^^M" d\o<A 

f P ^ 3L5.34) 

5,3 Process 

Component Types 

Distillation Columns 

Absorbers 

Strippers 

Reactors 

Condensers 

Vaporizers 

Others 

Total Nuaber 

Ref # <o 

ifflfciE (patzer 

shown) 

i 

0 

i 

i 

o 

0 

1 1 

5 

. Pg * MlEf^M 
P.11 

6.4 Stoichiometry Ref # _£_ , Pg # (*•/&) 

Show calculations and assumptions and then summarize In table on next 

Pa9eY-*r

£ u«J. cafes ~.??tlo PU^ | jr v.Ifll i <L^rvA — * /. 0 |lo loSspk+KC/l A ) 

&-C- +Ue*jJ-i'c*{ t^UIff-l cS SL H^ Ws/oU^a/A, ^ ^ 

CJP\AJ (CU3 ) Z C(C(> rV4 c?// ^ . *" ^ • 3 ' fee, 

bis pL.e-h.ol A 

he. k^. C4^:>//» i.3f*»o/es bispU^t A < /W e bispU^/A y .0*4 -£^7A / 

mo. ^ . ut3coajz - i-38 Wi s ^S/DU^IA K /*»*(,/« bispAettotA x -05i T£J/* &cefa&~ 
P.12 

6.4 Stolchlonetry Conversion Factors 

1.0 

b) mmmiorSfmar for Cd>Product fl 

c) &$fcr$iocfactor for Co-9tmtt n 

d) Conversion Factor for ra-Product 13 

e) COR¥»rsfon factor for Co-Product 14 

f) Conversion Factor Comments 
P.13 

6.0 Chemical Data 

6.1 Balanced Chemical Reactions Ref # & pn § %\4 

6.2 Chemical Tree Ref # j, ^ Rg # ^ 
P.14 

„ , l* | 

(kg/kg product) 

6,4. 1 Product 

bispU^jl A 

6.4.2 Raw Materials. 

#1 . 

#2 . 

#3 

#4 

#5 . 

-oh^Gi 

r 

§,4,3 Co-Product* 

#i 

*2 . 

#3 . 

#4 

#5 . 

# i . 

#2 . 

#3 

#4 

#5 

U*0 

*it » 

$.4.$ Intermediates 

#i 

#2 

-

9oo57 

\OZ15X 

fso'desh^ 

>%x 

•XS 

.0% 
P.15 

7.0 Process Vent Emission Sources 

T,Z Wmm**"** «if$Sion$? Aj (Y/N) Ref # 

7.3 Comments g.r * 

., Pg # 

., Pg # 

7.4 MT*B* t «*fssfo«s? ^_ _ (Y/N) Ref # _£ Pg # J ^ ^ ; 

7

-

5 Com*nU Ref # Pg | 
P.16 

r

'^^^03SEBSS^y^^^^ JL . (Y/N) Ref # £ . Pg * * H 

7.9 - -Mgtyniy~u&d6Fv|aiua _J 

7.9 Comments R<* ' - 1 , Pg # ifc t 

- £xc£^ S pk* J Wry* \*u.US[ c/1S^,'ILft ^ V*A ^ ^ re^oUM . 
P.17 

8.0 Transfer Emission Sources 

8.2 What iltirials are transferred? 

Ref # Js. 

_^ (Y/N) 

., Pg * li ± 

Kyww f 

?ooS7 

8,2,2 CQ-ProdMCts 

8.3 Comments Ref # ., Pg # 
P.18 

9.0 Storage Emission Sources Ref # & Pg # 6*H fe ^5.34 

r .r Ar**igpftl% stored? / (Y/N) 

$.2 What materials are stored? 

Storage Service 

$H§ CA$ i ' Type 

9t2Tl Product cruA^yrolidty^OuucufU. 

bispki^f A £006 7 -ri^a-l p-r^e/tc^'f' 

9.2.2 Co-Products 

9.2.3 Raw Materials 

* 

•Vf-tfl 

tV^g^fyyygx 

W ^ /»<*/ hcff; 

6"764( v w *tW' 

9.2.4 Intermediates 

9.4 Comments 

CA«S# 7647010 
10.0. Wastewater Emission Sources 

V 

10.2 Describe wastewater 

P.19 

(Y/N) 

Ref # ± , Pg I HA fc* &M) 

Stream Equipment Component 

Number Producing Wastewater 

#1 

n 

#3 

Comments on flow 

.2fci!L 

•Pi'lfY*furK,+ cktj**4 

iHcluJa 5frippe r +o r^couar U d -*• U^O fe#urt*Jj 

i^»M 

-£m»v r^^. 

10.3 Stream Composition 

(provide only 1f readily available) 

Stream #1 

Ref I 

Steam #2 

., Pg # 

Organics Organics 

HAPs HAPs 

Water 

Other 

Water 

Other 
Stream #3 

Organics _ 

HAPs 

Water 

Other 

10.4 Comments 0tkf M _ M 

R«f * , Pg # 
m # * 

kjw. s^W iA (Jiienoj are discussed below: 

Phenolic resins are the major consumers of 

phenol and should maintain this position indefinitely. The major uses for phenolic resins 

are as plywood adhesives and as molding 

resins. See Chapter 10 for details on phenolic 

resins. 

Bisphenol A is used in the production of 

polycarbonates and epoxy resins, which are 

growing plastics. Bisphenol A is in turn obtained from phenol by the following reaction: 

O 

OH o 

I 

+ CHjCCH3 ^ 

CH3 

H O O{-OH 

CH, 

Bisphenol A 

+ H,0 

at 30 to 40°C for 8-1*2 hours. The pcrystallizes from the reaction mixture V 

a slurry. 

At the end of the reaction, the mix' 

washed with water and treated will' 

enough lime to neutralize the free 

Vacuum and heat are applied to the rep 

kettle, and water and phenol are dr 

separately from the mixture. The bac 

finished by blowing the molten product 

steam under vacuum at I50°C to removodor of the sulfur-containing catalyst. 

The molten bisphenol A product is que.. 

in a large volume of water, filtered, and • 

It is a light tan powder, which may be h % 

purified by recrystallization from solverY; 

The patent literature indicates Iha; 

exchange resins promoted with various » 

captans or amines may be used in some c I 

newer plants in operation today. 

U.S. consumption of bisphenol A d> 

1969 was 64 per cent in epoxy resins, 15 

y^« 

r Fl». 25.34 Manufactu 

''ng Co. I 

u

*

r

" ^Jh^\ 

7-

•Wwnol A 

cture of bisphe bin*.TM, r 

. A. (fl.,. „.,.. » . Wo. ,,. 22s llgsg, tmm i ^ ^ BaupMt 
p. 22_. 

CHEMICAL PROFILE 

BISPHENOL-A **,.„• 

SUPPLY 

PRODUCER CAPACITY* 

Aristech, Haverhill, Ohio 172 

Dow, Freeport, Tex 225 

General Electric, Mt Vernon, Ind 370 

Shell, Deer Park, Tex .350 

Total 1,117 

'Millions of pounds per year of 4,4-isopropyildenediprienol (BPA). Aristech was 

formed from the chemicals division of USX by a December, 1966, public offering. 

Aristech has expanded by 22 miHton pounds since 1984 through a series of debottteneckings, and will add another 20 mHUon pounds by October 1987. Oow's capacity 

has increased from 170 million pounds since 1964 through incremental expansions. 

In May, 1987, General Electric completed a second facility at ML Vernon, with 

approximately 150 million pounds of capacity. GE's production is entirely captive for 

polycarbonate resins. Profile last published 7/16/84; this revision, 7/27/87. 

DEMAND 

1986: 823 million pounds; 1987: 880 million pounds; 1991: 1,050 million 

pounds. (Includes exports). 

GROWTH 

Historical (1977-1980): 6.6 percent per yean future: 4 to 6 percent per year 

through 1991. 

PRICE 

Historical (1956-1987): High, 91c. per pound, polycarbonate grade, hooper 

cars, divd.; tow, 22%c. per pound, epoxy grade, bgs., t.i., fit. aid. Current 77c. 

to 87c. per pound, epoxy grade, hopper cars, divd.; 81c to 91c. per pound, 

polycarbonate grade, same basis. 

USES 

Polycarbonate resins, 50 percent; epoxy resins, 32 percent; miscellaneous, 

including unsaturated polyester resins, poiysuifone resins, poiyarylate resins 

and flame retardants, 6 percent; exports, 12 percent. 

I 

STRENGTH 

Polycarbonate resins have been growing in excess of 8 percent per year, with 

compact disc, automobile and thermoplastic alloying applications the main driving forces. The weakened dollar has created a considerable upswing in epoxy 

resin exports. 

WEAKNESS 

The epoxy resin business is mature, averaging only 2 to 3 percent annual 

growth; domestic epoxy resin consumption was down 2 percent in 1986. 

OUTLOOK 

New applications will continue to expand polycarbonate resins weU into the 

1990's. Other BPA-based high-performance resins, such as poiysulfones and 

polyarylates, are also expected to take offv although to some extent at the 

expense of polycarbonates. While aU producers are basic in raw material phenol 

ind dedicated to BPA, tightening phenol availability may eventually affect BPA 

pricing. , 

Toxics Bill Joins 

Administration o 

The chemical and oil industries joined 

the Reagan Administration last week in 

urging a Senate subcommittee to reject 

proposed legislation intended to regulate and reduce the release of toxic substances into the air. 

Substantial progress has been made in the 

reduction of air toxics within the framework 

of the existing Clean Air Act and proposed 

changes in the section that regulates them 

"could reduce public health protection by 

misdirecting regulatory efforts and resources," said Karen Shewbart, environmental manager for Dow Chemical Company's 

Texas operations. 

Testifying for Chemical Manufacturers 

Association before the Senate's environmental protection subcommittee, Ms. Shewbart 

stated that volatile hydrocarbon emissions 

have been dramatically reduced by the 

chemical industry during the last two • 

decades. i 

She noted that at Dow, these hydrocarbons, 

which include toxic air pollutants, have been 

reduced by 50-75 percent over the last 

decade. 

Ms. Shewbart also commented on two sections of the proposed amendment to the 

Clean Air Act which is up for reauthorization 

— hazardous air pollutants and extremely 

hazardous air pollutants. 

BILLS SHOULD PRIORITIZE EFFORTS 

She said that the objective of air toxics 

legislation must be to prioritize efforts and 

regulate those compounds which have the 

highest likelihood of human hazard, and that 

is where Environmental Protection Agency's 

present efforts are aimed. 

"Because of the large list of compounds 

that would be regulated under this legislation, EPA's efforts on prioritized compounds 

could be diminished and the net result could 

be less human health protection rather than 

more," said Ms. Shewbart 

In the area of extremely hazardous air 

pollutants, she noted that proposed changes 

"duplicate existing Federal programs which 

address this concern, and therefore, are not 

necessary." 

Ms. Shewbart also pointed out that "attaining clean air goals and protecting human 

health depends on fine tuning and supporting 

existing programs, rather than the radical 

restructuring as mandated in this bill." 

A spokesman for American Petroleum Institute said the air toxics portion of the proposed Clean Air Act amendments would create bureaucratic confusion, duplication of 

existing programs, regulatory paralysis, litigation and delay, and could actually undermine the goals of public health. 

"The zero risk philosphy embodied in this 

bill will drive a zero (air) emissions policy 

which ultimately would lead to a shutdown of 

many industrial facilities in this country,'' 

said Earl Arp, director of health and safety 

for Ashland Oil Company, Inc., testifying for 

API. The proposal fails to differentiate beba; 

sio 

tiv. 

no 

sou 

inr 

pot 

Mr. 

MCCTIM** ^ *» * • ***** n •» j= 
P.23 

ro! 

ST'^&?0

c°T^ 

j[98 9 DIRECTORY OF 

CHEMICAL PRODUCERS 

UNITED STATES OF AMERICA 

Information in this Directory is for the sole 

and private use of sponsors of the 

Directory of Chemical Producers Program. 

RADIAN LIBRARY 

RESEARCH TRIANGLE PARK, NO 
333 RAVENSWOOD AVENUE 

MENLO PARK, CALIFORNIA 94025 

(415)859-3627 

FAX: (415)326-5512 

TWX: 910-373-2046 

TELEX: 334486 

222.^ST"' 0" *-

 u~*",

"

d

 TM - "°r°<u°

ta

 - - - -»««- «• *—. i» 
P.25 

PRODUCTS 

1989 DIRECTORY OF CHEMICAL PRODUCERS 

UNITED STATES B 

Bismuth oxynitrate (See: Bismuth subnitrate under Medicinal 

(Pharmaceutical) Chemicals) 

Bismuth potassium tartrate (Potassium bismuth tartrate) 

H SA Corporation Ardsley, New York 

Bismuth salicylate, basic (See: Bismuth subsalicylate under 

Medicinal (Pharmaceutical) Chemicals) 

Bismuth stannate 

Ferro Corporation 

Coatings, Colors, & Electronic 

Materials Group 

Transelco Division 

Electronic Ceramic Materials 

Department 

M&T Chemicals Inc. 

Penn Yjn, New York 

Carrollton, Kentucky 

Bismuth subcarbonate (See: Medicinal (Pharmaceutical) 

Chemicals) 

Bismuth subgallate (See: Medicinal (Pharmaceutical) Chemicals) 

Bismuth subnitrate (See: Medicinal (Pharmaceutical) Chemicals) 

Bismuth subsalicylate (See: Medicinal (Pharmaceutical) 

Chemicals) 

Bismuth titanate 

Ferro Corporation 

Coatings, Colors, & Electronic 

Materials Group 

Transelco Division 

Electronic Ceramic Materials 

Department 

TAM Ceramics, Inc. 

Penn Yan, New York 

Niagara Falls, New York 

Bismuth trichloride (Bismuth chloride) 

The Procter & Gamble Company 

Richardson-Vieks, Inc., subsidiary 

J. T. Baker Inc., subsidiary Phillipsburg, New Jersey 

Bismuth trihydrate (See: Bismuth hydroxide) 

Bismuth trihydroxide (See: Bismuth hydroxide) 

Bismuth trinitrate (See: Bismuth nitrate) 

Bismuth trioxide (Bismuth oxide) (Bismuth yellow) 

Ferro Corporation 

Coatings, Colors, & Electronic 

Materials Group 

Transelco Division 

Electronic Ceramic Materials 

Department 

Mayfair Pharmaceutical Company 

Penick Corporation 

The Procter & Gamble Company 

Richardson-Vicks, Inc., subsidiary 

J. T. Baker Inc., subsidiary 

The Shepherd Chemical Company 

Penn Yan, New York 

Newark, New Jersey 

Phillipsburg, New Jersey 

Cincinnati, Ohio 

Bismuth yellow (See: Bismuth trioxide) 

Bismuth zirconate 

Ferro Corporation 

Coatings, Colors, & Electronic 

Materials Group 

Transelco Division 

Electronic Ceramic Materials 

Department 

TAM Ceramics, Inc. 

Penn Yan, New York 

Niagara Falls, New York 

Bis(neopentylglycol)-1,5-cyclohexanedimethylene 

phosphite 

General Electric Company 

GE Plastics 

Borg-Warne irg-i r Chemicals U.SA 

Ch hemicals Morgantown, West Virginia 

Bis(2-octyrj phthalate (See: Dicapryl phthalate under 

Plasticizers) 

Bisfj>entachlero-2,4-cyclopentadien-1-yl] (See: Dienochior 

under Pesticides) 

Bis[2,4-pentanedionato] beryllium (See: Beryllium 

acetylacetonate) 

Bis(2,4-pentanedionatO] cadmium (See: Cadmium 

acetylacetonate) 

Bis(2>4-pentanedionato] calcium (See: Calcium 

acetylacetonate) 

Bis(2,4-pentanedionato] copper (See: Copper 

acetylacetonate (cupric)) 

Bisf.2,4-pentanedionato] lead (See: Lead acetylacetonate) 

Bi*[2,4-pentaned.onato] magnesium (See: Magnesium 

acetylacetonate) 

Bit[2,4-pentanedionato] manganese (See: Manganese 

acetylacetonate) 

Bis(2,4-oentanedionsto]-0,0-nickeJ (See: Nickel 

acetylacetonate (nickelousH 

Bis(2,4-oentanedionato] platinum (See: Platinum 

acetylacetonate) 

Bisf2,4-pentanedionato] potassium (See: Potassium 

acetylacetonate) 

BisCpentanedionatoJvansdyl (See: Vanadium acetylacetonate) 

Bis(2,4-pentanedionato] zinc (See: Zinc acetylacetonate) 

Bisphenol A (2.2-Bis(4-hydroxypheny)] propane) (p,pDihydroxydiphenyldimethylmethane) (0-Oi-phydroxyphenylpropane) (4,4'-lsopropylidenediphenol) 

Aristech Chemical Corporation Haverhill, Ohio* 

Dow Chemical U.SA Freeport, Texas 

General Electric Company 

GE Plastics Mount Vernon, Indiana 

Shell Oil Company 

Shell Chemical Company, division Deer Park, Tens 

Source: SFtl International estimates at or January 1,1989. 

TOTAL 

Annual Capacity 

(Millions of Pounds) 

192 

22S 

370 

350 

1.137 

SRI International 487 

'*S*f$0W\. 
KE- 151+ 

Riegel's 

Handbook of 

Industrial Chemistry 

SEVENTH EDITION 

Edited by 

James A. Kent 

College of Engineering 

Michigan Technological University 

Houghton, Michigan 

VAN NOSTRAND REINHOLD COMPANY 

NEW YORK CINCINNATI ATLANTA DALLAS SAN FRANCISCO 

LONDON TORONTO MELBOURNE 

RADIAN LIBRARy 

DURHAM, N.C. 
Van Nostrand Reinhold Company Regional Offices: 

New York Cincinnati Chicago Millbrae Dallas 

Van Nostrand Reinhold Company International Offices: 

London Toronto Melbourne 

Copyright © 1974 by Litton Educational Publishing, Inc. 

Library of Congress Catalog Card Number: 73-14798 

ISBN: 0-442-24347-2 

All rights reserved. Certain portions of this work copyright © 1962 

by Litton Educational Publishing, Inc. No part of this work 

covered by the copyrights hereon may be reproduced or used in any 

form or by any means-graphic, electronic, or mechanical, including 

photocopying, recording, taping, or information storage and retrieval 

systems-without written permission of the publisher. 

Manufactured in the United States of America 

Published by Van Nostrand Reinhold Company 

135 West 50th Street, New York, N.Y. 10020 

Published simultaneously in Canada by Van Nostrand Reinhold Ltd. 

15 14 13 12 11 10 9 8 7 6 5 

Library of Congress Cataloging in Publication Data 

Riegel, Emil Raymond, 1882-1963 

Riegel's handbook of industrial chemistry. 

First-5th ed. published under title: Industrial 

chemistry; 6th ed. in 1962 under title: Riegel's 

industrial chemistry. 

Includes bibliographical references. 

1. Chemistry, Technical. I. Kent, James A., 1922-

ed. II. Title. III. Title: Handbook of industrial . 

chemistry. 

TP145.R54 1974 660 73-14798 

ISBN 0442-24347-2 
I 

814 RIEGEL'S HANDBOOK OF INDUSTRIAL CHEMISTRY 7*£/ SVNTHETIC ORGANIC CHEMICALS 816 

chlorobenzene, Raschig, and benzoic acid. 

About 60 per cent of the phenol produced in 

1969 was by the cumene process. All but lhe 

benzoic acid process require benzene as the 

raw material. The benzoic acid process uses 

toluene as the starting aromatic material. Details of the phenol manufacturing process are 

given in Chapter 10. 

Some of the major uses for phenol are discussed below: 

Phenolic resins are the major consumers of 

phenol and should maintain this position indefinitely. The major uses for phenolic resins 

are as plywood adhesives and as molding 

resins. See Chapter 10 for details on phenolic 

resins. 

Bisphenol A is used in the production of 

polycarbonates and epoxy resins, which are 

growing plastics. Bisphenol A is in turn obtained from phenol by the following reaction: 

OH 

o 

O 

fl 

+ CH3CCH3 

CH, 

H O O{-OO H 

CH, 

Bisphenol A 

H 2 0 

A flow sheet for bisphenol A manufacture is 

shown in Fig. 25.34. 

Phenol and acetone in a molar ratio of 3:1 

or 4:1 are charged to an acid-resistant stirred 

bisphenol A reactor. Glass-lined equipment is 

used ordinarily. A sulfur-containing catalyst is 

added,'then dry HCI gas is bubbled into the 

reaction mass. The temperature is maintained 

al 30 to 40°C for 8-12 hours. The product 

crystallizes from the reaction mixture to form 

a slurry. 

At the end of the reaction, the mixture is 

washed with water and treated with just 

enough lime to neutralize the free acid. 

Vacuum and heat are applied to the reactionkettle, and water and phenol are distilled 

separately from the mixture. The batch is 

finished by blowing the molten product with 

steam under vacuum at 150°C to remove the 

odor of the sulfur-containing catalyst. 

The molten bisphenol A product is quenched 

in a large volume of water, filtered, and dried. 

It is a light tan powder, which may be further 

purified by recrystallization from solvents. 

The patent literature indicates that ionexchange resins promoted with various mercaptans or amines may be used in some of the 

newer plants in operation today. 

U.S. consumption of bisphenol A during 

1969 was 64 per cent in epoxy resins, IS per 

cent in polycarbonate resins, and 21 per cent 

in other uses. Total consumption was over 

182 million pounds. 

Other products from phenol include aspirin, 

alkylated phenols, chlorinated phenols (to 

2,4-D), and caprolactam. Chemical reactions 

for some of these materials are shown below: 

OH ONa OH 

Important by-products from the chlorobenzene process which are now substantial 

volume chemicals are phenylphenols, numerous chlorophenols, and Dowtherm* A (a 

eutectic mixture of diphenyl and diphenyl 

oxide sold as a heat transfer medium). 

COONa 

Phenol 

O 

I 

O H

 ....... . OC—CH, 

QCOOH -ftgsr rSco°" 

Salicylic Acid Aspirin 

OH OH OH 

- o •~ *• am • o 

>-Alky! phenol 

CH2CH2R 

p-Alkyl phenol 

tiMiti 11 

Lla» I 

l l 

ns 

<v> 

li 

Wotetr 

Quench 

Filtration ft. 

Oriing 

Fig. 25.34 Manufacture of bisphenol A. [Pot. Ref.. 38, A'o. // , 225 (1959). copyright 1959 by Guff Publishing Co. I 

O 

OH OH |[ O*0a

0 

o I 

OH OCH,COH OH 9 OCH,C 

( ^ ) • ci,

 9-^L r-^V1

 qcH.coH r^jc i 

Cl Cl 

NII,OH 

C

(2.4-D) 

H ' 

Beckmann 

rearrangement 

/ s yf 

H2C C \ 

NH / 

H,C N ^CH , 

C H , 

Caprolaclum 

ro 

co 
'"' 

\ 

1 

I 

\ 

i 

i 

i 

1 

I 

1. 

i 

If 

i 

• 1 

V 

i 

1 

i \ 

X 

\\. 

y 

r 

v. 

! *«m 

i 

i 

Survey of 

Industrial Chemistry 

Philip J. Chenier 

'• Professor 

!| Department of Chemistry 

| University of Wisconsin-Eau Claire 

Eau Claire, Wisconsin 

A Wiley-Interscience Publication 

JOHN WILEY & SONS 

New York • Chichester • Brisbane • Toronto • Singapore 

P.29 

BBBBBBBBBBBBBBBBBBBBBBBBBBBBmJ 

aaaaaaaaaaaaaaaaaaaaaaaaaaV 

^aaaaaaaaflaaaaaV 
Copyright © 1986 by John Wiley & Sons, Inc. 

All rights reserved. Published simultaneously in Canada. 

Reproduction or translation oi any part of this work 

beyond that permitted by Section 107 or 108 ofthe 

1976 United States Copyright Act without the permission 

of the copyright owner is unlawful. Requests for 

permission or further information should be addressed lo 

the Permissions Department, John Wiley & Sons, Inc. 

Library of Congress Cataloging in Publication Data: 

Chenier, Philip J. 

Survey of industrial chemistry. 

"A Wiley-Interscience publication." 

Includes bibliographies and index. 

1. Chemistry, Technical. I. Title. 

TPI45.C44 1986 

ISBN 0-471-01077-4 

660 86-7813 

Printed in the United States of America 

10 9 8 7 6 :"> 4 :•» '.' 1 
182 Chemicals trom Propylene and Butylene 

to poly (methyl methacrylate), an important plastic known for its clarity and 

used as a glass substitute. The synthesis is outlined as follows. 

o 

II 

C H 3 -C-CH 3 + 

CH, O 

V II 

C H 2 =C-C-OC H 

HCN— -

H,<> 

i -* 

OH 

1 

CH.-C-CH , 

1 

C=N 

1 -H,0 

• A 

CH3 

1 

C H2=C-C=N 

CH,OH 

methyl methacrylate 

The first reaction is a nucleophilic addition of HCN to a ketone, the 

second is a dehydration of an alcohol, and the third is hydrolysis of a nitrile 

to a carboxylic acid and esterification of the acid by methanol. 

An alternate method of making methyl methacrylate is being developed 

lhat would synthesize it more directly from propylene. This synthesis is not 

yet commercial. It involves reaction of propylene with carbon monoxide and 

methanol followed by an air oxidation. If successful it would make poly 

(methyl methacrylate) much cheaper. 

C H3 - CH = CH2 + CO + CH3OH S*h+ 

CHS O CH, O 

\ 11 V 11 

C H 3 -CH-C-OCH 3 _22_ ^ CH 2 =C-C-OCH 3 + H 2 0 

A 

metal 

oxides 

Aldol chemicals refer to a variety of substances desired from acetone 

involving an aldol condensation in a portion of their synthesis. The most 

important of these chemicals is methyl isobutyl ketone (MIBK), a common 

solvent for many plastics, pesticides, adhesives, and pharmaceuticals. 

Approximately 0.15 billion lb of MIBK were made in 1984. The synthesis is 

outlined here. 

C^L*<t~is" 

Acetone 183 

O 

II 

2CH,-C-CH , on 

O 

II 

-cCH, O 

I II 

C H3 -CH-CH2 -C-CH:»-.Ii 

MIBK 

CH:, 

I 

CH,-C-CH,-C-CH , 

I 

OH 

diaceione alcohol 

, A 

C H, O 

I II 

CH.-OCH-C-CH; , 

mesityl oxide 

J-H„ 

Diacetone alcohol is a solvent used in hydraulic lluids and printing inks. 

Recall that the aldol condensation is an example ol a variety of carbanion 

reactions used lo make large molecules from smaller ones. An aldehyde or a 

ketone with at least one hydrogen on the curlxin next to the carbonyl will 

react to give the aldol condensation. The mechanism is given as follows. 

e 

:OH 

e 

'- CH,-

e n 

+/CH 2 -C-CH, , 

(): 

II 

C-CH;, + HAY 

:6-& O 

I II 

==i CH 3 -C-CH 2 -C-CH 3 

I II 

C H 3 -C-CH 2 -C-CH , + H2 0: 

I 

CH3 

CH3 

OH :() 

I II 

'CH,-C-CH a -C-CH , 

I 

C H, 

e 

+ OH 

Finally, bisphenol A is manufactured by a reaction between phenol and 

acetone, the two products from the cumene hydroperoxide rearrangement. 

Bisphenol A is an important diol monomer used in the synthesis of 

Polycarbonates and epoxy resins as we will see later. Over a half billion 

Pounds per year of this chemical is made. 

CH, 

!»^0> 

CH, 

I

 3 

* 0=C 

I 

CH, '•HOH-C^"'0 

CH, 

bisphenol A 
Klaus Weissermel 

Hans-Jiirgen Arpe 

Industrial 

Organic Chemistry 

Important 

Raw Materials and 

Intermediates 

Translated by 

Alexander Mullen 

Verlag Chemie • Weinheim • New York 

1978 

* 
Prof. Dr. Klaus Weissermel 

Dr. Hans-Jiirgen Arpe 

Hoechst AG 

Postfach 8003 20 

D-6230 Frankfurt 80 

West Germany 

Preface 

Copy Editing: Dr. Hans F. Ebel 

This book contains 43 Tables 

CIP-Kurztitelaufnahme der Deutschen Bibliothek 

Weissermel, Klaus 

Industrial organic chemistry: important raw 

materials and intermediates / Klaus Weissermel; 

Hans-Jiirgen Arpe. - l.Aufl. - Weinheim, New York: Verlag Chemie, 1978. 

Dt. Ausg. u.d.T.: Weissermel. Klaus: Industrielleorganische Chemie. 

ISBN 3-527-25706-3 (Weinheim) 

ISBN 0-89573-005-7 (New York) 

NE: Arpe, Hans-Jiirgen: 

© Verlag Chemie GmbH, D-6940 Weinheim, 1978 

All rights reserved (including those of translation into foreign languages). No part of this book may be reproduced in 

any form - by photoprint, microfilm, or any other means - nor transmitted or translated into a machine language 

without written permission from the publishers. 

Registered names, trademarks, etc. used in this book, even without specific indication thereof, are not to be considered 

unprotected by law. 

Printer: Passavia Druckerei GmbH Passau 

Printed in West Germany 

Industrial organic c 

as well as, to an im 

present status of ki 

There was thus a gr 

and intermediates 

and to present it in 

development, whic 

from their industria 

ing discussions wit! 

This book addresse 

from it the chemist 

manufacturing proi 

glean information ; 

and feedstocks aiodisciplines in the c 

economists - will 1 

economic interred 

This book is arrang 

their tightest possil 

unavoidable. The i 

As a rule, the mam 

ment and signifies 

applications of the | 

products are frequ 

existing technologic 

more economic or i 

The authors endea' 

information are at 

1. The main text. '! 

2. The synopsis of' 

3. Flow diagrams il 

These three types o 

or making brief no 

notes which briefly 

to be rapidly infort 
314 13. Benzene Derivatives 

application of phenol: 

1. phenolic resins Wapolycondensation with 

HCHO, with hydroxymethylphenols as 

precursors 

OH 

CH2OH 

production of phenoplasts (in l,000t): 

1974 1975 1976 

USA 725 578 708 

Japan 239 196 254 

W.Germany 176 143 166 

2. E-caprolactam with KA precursors 

(5° multi-stage 

(CH2). 

3. bisphenol-A, A = acetone 

(bisphenol-B, B = butanone 

bisphenol-F, F== formaldehyde 

commercially less important) 

once again. The Hock variant is thus multi-stage but free from 

co-product. 

13.2.1.3. Phenol Applications and Secondary Products 

The phenol consumption in the USA, Japan, and Western 

Europe can be summarized with regard to application areas as 

listed in Table 13-4: 

Table 13-4. Phenol Applications in USA, Japan, and 

Western Europe (in %). 

USA 

1972 

Phenol resins 50 

e-Caprolactam 20 

Bisphenol-A 10 

Adipic acid 5 

Alkylphenols 5 

Various') 10 

') e.g. aniline, plasticizers, 

1976 

46 

14 

14 

3 

J 23 

Japan 

1972 

54 

-

24 

-

5 

17 

antioxidants, etc. 

1976 

50 

-

26 

-

4 

20 

W. Europe 

1972 

33 

30 

13 

13 

11 

According to the above, phenolic resins or phenoplasts - the 

polycondensation products of phenol with formaldehyde-possess the greatest importance in these countries. They serve in, for 

example, the manufacture of paints, adhesives, molding materials, and foam plastics. The production figures for phenolic 

plastics in the USA, Japan, and W. Germany are summarized in 

the adjacent table. 

The manufacture of e-caprolactam ranks second in the USA 

and Western Europe. However in Japan, e-Caprolactam production is based solely on cyclohexane. For the same reason, 

adipic acid is not manufactured from phenol in Japan, because 

e-caprolactam and adipic acid are produced in other countries 

from phenol via the same intermediate, cyclohexanol. 

2,2-Bis-(4-hydroxyphenyl)-propane, the third largest consumer of phenol, is known as bisphenol-A or dian on account of 

its production from phenol and acetone (eq. 21). The available 

production figures for bisphenol-A in the USA and Japan are 

listed in the adjacent table. The present production capacity in 

W. Germany is estimated to be approx. 55,000 t/a. 

The condensation of acetone with excess phenol can be conducted either continuously or discontinuously in the presence of 

H2S04 c 

catalyst 

carried o 

Accordii 

system c. 

2 HOY 

Bisphenc 

resins ar 

from the 

These et 

being hai 

nates ar 

phosgene 

Polysulfc 

diphenyl 

The addi 

tion is gt 
but free from 

•ducts 

and Western 

ition areas as 

13.2. Oxidation and Secondary Products of Benzene 315 

H2S04 or, according to the Hooker process, with dry HCI as 

catalyst and methylmercaptan as promoter. The reaction is 

carried out at approx. 50 °C, the yield being almost quantitative. 

According to the UCC process also a heterogeneous catalyst 

system can be employed: 

2 HO 

.CH, 

+ o=c 

[H*] 

CH, 

CH 

CH, 

+ H2 0 (21) 

production of bisphenol-A (in 1,0001): 

1974 1975 1976 

USA 168 133 191 

Japan 51 40 n.a. 

n.a. = not available 

manufacture of bisphenol-A: 

acetone-phenol condensation, 

catalyst: H,S04 

HCI (Hooker) 

promoter: CH3SH 

W. Europe 

1972 

33 

30 

13 

13 

11 

jplasts - the 

ehyde-posyservein.for 

olding matefor phenolic 

immarized in 

in the USA 

olactam proline reason, 

pan, because 

ier countries 

inol. 

largest conjn account of 

Tie available 

nd Japan are 

•n capacity in 

a. 

can be cone presence of 

Bisphenol-A is widely used in the manufacture of synthetic 

resins and thermoplastics. Bisphenol-A-glycidyl ethers result 

from the reaction between bisphenol-A and epichlorohydrin. 

These ethers are the basis of epoxy resins which are capable of 

being hardened (cf. Section 11.2.1). Thermoplastic polycarbonates are obtained by condensation of bisphenol-A with 

phosgene or by transesterification with diphenyl carbonate. 

Polysulfones are obtained by reacting with 4,4'-dichlorodiphenylsulfone. 

The addition of olefins to phenol yields alkylphenols. The reaction is generally conducted in the liquid phase at 50°C with 

equimolar amounts of reactants and BF3 or HF as catalyst. 

Isooctyl, isononyl, and isododecyclphenols possess the greatest 

importance since they can be produced from the cheap olefins, 

diisobutene, tri- and tetrapropene. 

These long-chain phenols are ethoxylated at the OH groups 

with ethylene oxide (cf. Section 7.2.2) for their application as 

non-ionic detergents, wetting agents, and emulsifying agents. 

Furthermore, they are also used as additives for cutting oil and 

as auxiliary products in rubber and plastic processing. Their 

surfactant properties can be reinforced by sulfonation. However, they are markedly decreasing in importance due to their 

resistance to biological degradation. 

Recently, o-cresol and 2,6-xylenol have found greater application, with the result that the demand for o-cresol could no 

longer be met solely from petroleum and tar distillate sources. 

Manufacturing processes had to be developed for 2,6-xylenol as 

it is not found in natural products. 

Both products are manufactured in the liquid phase by methylation of phenol with methanol. This reaction is carried out in the 

application of bisphenol-A in reactions: 

3.1. with epichlorohydrin forming epoxy resin precursors 

3.2. with COCl2 to polycarbonates 

to polysulfones 

-Cl 

4. alkylphenols 

4.1. higher alkylphenols: 

manufacture via catalytic phenol alkylation with olefins in liquid phase 

R generally KO-C8H, 7 

/'so-CsH19 

«o-C12H25 

applications of alkylphenols: 

after EO addition (ethoxylation): 

wetting agents 

emulsifying agents (non-ionic) 

detergents with limited biological degradability 

additional sulfonation increases surfactant 

properties 

4.2. methyl- and dimethylphenol: 

manufacture via: 

heterogeneously catalyzed liquid-phase 

methylation of phenol with methanol 
P.36 

C&toUcal P%oditcta$y*xfau 

Subscription for: 

Radian Corporation 

7K***4<UtU Chemical Products 

Box 232 • Cortland, New York 13045 • (607)753-8700 
P.37 

- ' ,..s 

tfdfn/cii/ Ptffi/rtefd Smm&$4<£ 

FEBRUARY 1988 4 ^ 

Pievfow Report — October 1985 

A Reporting Service of 

Mannsville Chemical Products Corp. 

Asbury Perk, NJ 07712-0271 

BISPHENOL A 

FOCUS....Bisphenol A (abbreviated BPA) is a primary rati material for the production of polycarbonate (PC), 

epoxy, bisphenol A-formaldehyde, phenoxy, and high-performance resins including polyesters, polyacrylates, 

and polysulfones. Polycarbonates have outpaced epoxies as the largest derivative of BPA. Although epoxy 

resin markets are relatively mature, moat engineering plastics and high-performance resins continue to 

have high rates of consumption growth as metal replacements in automotive, appliance and electronic applications. By the 1990's PC may become the largest volume engineering plastic, excluding possibly nylon. 

With a high level of exports, US production of bisphenol A exceeded one billion pounds in 1987. 

Although U.S. 1967 BPA output increased by about 5% compared to 1986, apparent domestic demand remained 

relatively static, based on available preliminary production reports from the US International Trade Commission. Based on historical comparisons and extrapolation of eatimated BPA consumption increases for 

msjor derivBtives for 1987, it is quite possible thst the final report of production for 1987 will be 

about 10 percent higher than the preliminary data. Based on various trade reports snd estimates, US output 

of polycarbonate resins in 1987 increased by 8-10%. Growth for PC resins has been in established markets 

as well as in emerging markets including medical, packaging, film, and alloys and blends. In addition to a 

high rate of growth for PC resins, epoxy resin production reportedly increased by about 8% in 1987. In 

addition to higher domestic consumption of epoxies, exports increased. 

OUTLOOK....Consumption of epoxy resins will have only limited future growth in end uses such as protective 

coatings and adhesives. However, there will be growth for electrical/electronic applications for epoxies 

in fiber-reinforced laminates for printed circuit boards and encapsulations for electronic devices. 

Demand for polycarbonates rose dramatically during the 1970's, with estimated US consumption in the 

range of one-qusrter billion pounds by 1980. Demand for polycarbonates was relatively static during the 

early yeera of the 1980's. By 1987, US polycarbonate demand was almost 400 million pounds. Major demand 

growth for PC has been in automotive and safety glazing. Electronics and communications also contributed 

to strong growth, particularly use for business machine houaings and compact discs. Based msinly on a high"! 

level of growth for PC resins, overall US BPA consumption will probably increase by about 6% annually over ] 

the next five year period. 

PRICING....Captive consumption for epoxy, polycarbonate, and specialty resin manufacture accounts for well 

over one-half of US biaphenol A demand. Therefore, it is difficult to determine what BPA transfer values 

are assigned for internal uae. Most merchant market aales are to large-volume resin producers at negotiated prices. For this reason, publiahed list prices generally do not reflect actual selling prices. List 

prices are subject to various temporary voluntary allowances as reflected in the average sales value aa 

reported by the USITC. The actual selling price of BPA will probably increase moderately in the future. 

AVERAGE PRICE RANGE - BISPHENOL A 

Cents Per Pound • TL/CL (Hopper) - Freight Allowed - Epoxy Grade 

Trsde List 

Avg. Sales 

1960 

"29J 

27 

1965 

21 

1970 

~ZoT 

17 

1975 

~52T 

33 

1980 TT 

48 

1984 ST 

48 

1985 TT 

48 

1986 sr 

43 

1987 1988 ST 1989 

-9TT 

1991 

"9TT 

The list price for polycarbonate grade is 4 cents per pound higher. 

SUPPLY AND DEMAND....Millions of Pounds....Estimated....Domestic US 

Capacity 

Production 

Merchant Sales 

Imports 

Exports 

Demand 

1960 

51 

1965 

-T5ff 

97 

97 

1970 

~27D 

202 

202 

1975 

"525 

293 

97 

293 

1980 

840 

530 

130 

40 

490 

1984 

~BS5 

762 

318 

42 

720 

1985 

895 

949 

330 

62 

887 

1986 

730 

956 

341 

79 

877 

1987 

TT37 

1000 

n/a 

2 

112 

890 

1988 

TI37 

950 

1989 

1000 

1991 

1150 

Imports of bisphenol A, separately reported by the US Bureau of Census, were less than 1/2 million 

pounds per year before 1987. Exports of BPA were not separately reported before 1984. Exports for 

1980 are estimated. 

AVAILABILITY....Shortages of cumene-derived phenol raw material could develop. However, it is not anticipated that bisphenol A supply will be affected. fAll US producers of BPA also manufacture phenol and would 

probably give supply preference to making raw material available to manufacture higher value added derivatives such as BPA.} Producers of BPA have generally made recent increases in phenol capacity or have plans 

for future expansions snd debottlenecking which should eneure supply. From the standpoint of nameplate 

operating plant size for bisphenol A, there appears to be adequate US capacity for the next few yeara. 

With moderated domestic demand growth and an anticipated decline in exports, US producers may not have to 

make any major capacity additions until the 1990'a. However, GE is studying the construction of a new 

facility in Alabama. [US exports of BPA are expected to decline as more capacity is installed overseee.j 

General Electric Co. end Mitsui Petrochemical formed a joint venture to make BPA in Japan. General Electric Plastics Europe also has a BPA plant under construction in the Netherlands. In Brazil, Rhodia, the 

subsidiary of France'8 Rhone-Poulenc, is expanding BPA capacity to 30,000 metric tons per year. 

8/86 
P.38 

PRODUCERS AM) CAPACITIES - BlSHPtfctTM^ -^LION S OF POUNDS 

PRODUCER LOCATION '' i 1988 CAPACITY 

Aristech Haverhill, OH '• 152 ~ iz<£ i-,g~, 

Dow Chemical Freeport, TX 225 

General Electric Mt. Vernon, IN 370 

Shell Chemical Deer Parte, TX 350 

TOTAL 1137 

Based on announced capacities and trade estimates. Aristech was formed from the chemical 

division of USX and has been expanding in stages to about 192 mm lbs. Aristech plana a 

further increase in 1989 to about 228 million pounds through debottlenecking. Dow increased capacity incrementally to about 225 million pounds in 1986. Dow may make a further 

major expansion. With the completion of a second facility at Mt. Vernon, IN in early 1987, 

GE's capacity was increased by about 150 million pounds. GE is reportedly considering the 

construction of an entirely new BPA facility in Alabama. GE uses all material captively. 

END USES....Bisphenol A (BPA), also referred to aa 2,2-bis(p-hydroxyphenyl) propane and 4,4 isopropylidenediphenol, is a monomer used to produce epoxy, polycarbonate, BPA-formaldehyde, phenoxy, polyester, 

snd other resins. It also functions as a chemical intermediate since it can be readily halogenated, hydrogens ted, and sulfonated. Applications for various resins and derivatives of BPA include the construction, 

automotive, aircraft, appliance, and electronic industries. 

BPA is s crystalline, prilled, or flake material with a mild phenolic odor. Dow introduced a granulated form in 1987. It is soluble in alcohol and acetone, slightly soluble in carbon tetrachloride, 

practically insoluble in wster, but soluble in aqueous alkaline solutions. Commercially, bisphenol A is 

available in both epoxy and higher-purity polycarbonate grades, sold at a higher price. The polycarbonate 

grade is also used for polysulfone resins. For making epoxy resins, and most other uses, the epoxy grade 

is usuBlly suitable. 

Polycarbonate resins, made by reacting bisphenol A with phosgene (carbonyl chloride), are water-white, 

impact-resistant thermoplastic polymers used for high-performance moldings, shatterproof window glazing, 

and a vsriety of specialties. Polycarbonatea are now the major derivative of BPA. 

Epoxy resins, previously the largest outlet for BPA, are commonly the reaction products of a polyhydric phenol and a chlorohydrin or simple epoxide. The major commercial epoxy is obtained using bisphenol A 

snd epichlorohydrin as the reactants. Epoxy resins provide toughness, corrosion resistance, adhesion, and 

electrical insulation, among other properties. Epoxies are widely used in protective coatings, adhesives, 

and plastics. Epoxy resins are also widely used in laminating printed circuit boards and for encapsulating 

electrical devicee. Phenoxy resins are produced by the copolymerization of BPA snd epichlorohydrin but, 

unlike epoxies, do not require esterification with long-chain unsaturated acids or reaction with amidee or 

amines to produce cured resins. Coatings based on phenoxy resins are tough and have excellent adhesion. 

Bisphenol A-formaldehyde resins are used in specialty applications, including inks, coatings, varnishes, and abrasive binders. Polyesters are prepared from BPA and an alkalene oxide such as propylene oxide. The glycol produced in the reaction can be eaterified with maleic or other dibasic acids. These polyesters have excellent chemical resistance and can be laminated with glass fiber to fabricate corrosionresistant chemical process equipment. Tetrabromobiephenol A, the principal halogenated derivative of BPA, 

has flame-retardant applications. 

END USE PATTERN - 1987 ESTIMATE 

DERIVATIVE PERCENT 

Polycarbonate Resins 53 

Epoxy Resina 37 

Tetrabromobiephenol A 2 

Miscellaneous 5 

MANUFACTURING....About 0.88 pound of phenol is required to produce one pound of bisphenol A, with about 

0.28 pound of acetone needed. Bisphenol A is produced by the condensation of two moles of phenol with one 

mole of acetone. Excess phenol is reacted with acetone in the presence of an acid catalyst, using a small 

amount of a catalyst- promoter such as methyl mercaptan. The catalyst, dry hydrogen chloride gas, is 

bubbled through the mixture for several hours and the reaction temperature is controlled. After reaction, 

crude product is stripped of HCI snd water of reaction. Recovered HCI and excess phenol are recycled. 

Crude BPA is dropped as a slurry into stills for purification. The slurry is washed with water, neutralized with milk of lima, and distilled under vacuum at temperatures up to 150°C. The molten product remaining in the still ia sparged with steam at 150°C to remove final traces of the odorous mercaptan promoter. 

The deodorized melt is then quenched in water, washed, filtered, snd dried. 

While bisphenol A plants are comparatively simple, the production of BPA is s delicate process since a 

number of isomers and tri- or mono-hydroxy byproducts are formed. While a product containing these impurities may be used for the manufacture of epoxy resins, it is not suitable for polycarbonates. Early 

batch processes eliminated these impurities by high-cost crystallization. Newer processes employ distillation and extractive crystallization under pressure to purify crude bisphenol A continuously. This greatly 

improves the economics. Distillation of BPA is especially difficult because numerous elements, some in 

minute concentrations, decompose the product or promote the formation of polymers snd tar. 

ENVIRONMENTAL ASPECTS....Bisphenol A is irritating to skin and eyes. The solid material is an irritating 

duat and can irritate upper respiratory passsges. The EPA has proposed tests of pulmonary effects as well 

as aquatic toxicity. The ingestion toxicity of BPA is very low, but ingestion should be minimized. 

To the best of our knowledge, the information contained herein is accurate. However, we 

do not assume any liability whatsoever for the completeness or accuracy of this report.