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# OAR Box 1877 Prepped by Keeia Richards



## Document

Number: 

# 25 ) ll-B-2 2 Docket Number: 

# A-90-1 9

Printed 12/2/2008J

0:36:48AM

Sheet 25of 46

## P. 2

% : 

# A-90-1 9 ll-B-2 2

MEMORANDU M
TO : Proces s Vent s Docke t A-90-1 9 FROM : Wand a Floy d DATE : Novembe r 199 0 SUBJECT : HO

NNESHAP : Industr

yCharacteristics/Bispheno l Attache d i s a product-proces s summar y(PPS ) fo r th

e productio n o f Bispheno l A vi a condensatio n o f Pheno l an d Aceton e category . Thi s PP S wa s develope d a s par t o f th e Industria l Profil e projec t i n suppor t o f the Hazardou s Organi c NESHA P (HON ) regulator

yeffort . Informatio n i n thi s PP S i s use d a s a basi s fo r emission s an

d cos t impac t estimate s fo r the HO Nprogram . Liste d belo w ar e th e keyreference s use d i n developing the attache d PPS . "Bispheno l A. " In : Mannsvill e Chemica l Products . Ne w York , February , 1988 . 198 9 Directoryo f Chemica l Producers . SR I International . California , p . 487 . Kent , Jame s A . Riegel' s Handboo k o f Industria l Chemistry . 7t h edition . Va n Nostran d Reinhol d Company , Ne w York , 1974 . pp . 814-815 . Chenier , Philip , Jr . Surveyo f Industria l Chemistry . Joh n Wile y& Sons , Ne w York , 1986 . pp . 182-183 . Weissermel , Klau s an d Arpe , Hans-Jurgen . Industria l Organi c Chemistry . Verla g Chemie , ne w York , 1978 . pp . 314-315 . "Bispheno l A. " In : Chemica l Marketing Reporter . Ne w York , Jul y27 , 1987 .

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### Date : S/A*/1* 

## Reviewer : _J_ V
ADMINISTRATIV

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### iA (Jiieno j ar e discusse d below : Phenolic

resins ar e th e majo r consumer

s o f pheno l an d shoul d maintai n thi s positio n in definitely . Th e majo r use s fo r phenoli c resin

s ar e a s plywoo d adhesive

s an d a s moldin g resins . Se e Chapte r 1 0 fo r detail s o n phenoli c resins . Bisphenol

A i s use

d i n th e productio n o f polycarbonate

s an d epox

y resins , whic h ar

e growin g plastics . Bispheno l A i s i n tur n obtained fro m pheno l by th e followin g reaction : 

# O O H o 

# I + CHjCCH 3 

### ^

CH 3 

# H O 

# O{-O H

CH , Bispheno l A 

### + H, 0 at 3 0 t o 40° C fo r 8-1* 2 hours . Th e p

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t ar e applie d t o th e re

p kettle , an d wate r an d pheno l ar e d r separatel y fro m th e mixture . Th e ba c finished b y blowin g th e molte n product stea m unde r vacuu m a t I50° C t o remov

odo r o f th e sulfur-containin g catalyst . Th e molte n bispheno l A produc t i s que. . i n a larg e volum e o f water , filtered, an d • I t i s a ligh t ta n powder , whic h ma y b e h % purifie d b

y recrystallizatio n fro m solverY ; Th e paten t literature indicates Iha ; exchang e resin s promote d wit h variou s » captan s o r amine

s ma y b e use d i n some c I newe r plants i n operatio n today . U.S . consumptio n o f bispheno l A d > 196 9 wa s 6 4 pe r cen t i n epox

y resins , 1 5



# y^« 

# r Fl» . 25.3 4 Manufact u ''ng Co. I u 

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## " 

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ctur e o f bisphe r 

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BaupMtp . 22_
. 

# CHEMICA L PROFIL E BISPHENOL-A **,.„• SUPPL Y PRODUCE R CAPACITY * Aristech , Haverhill , Ohi o 17 2 Dow , Freeport , Te x 22 5 Genera l Electric , M t Vernon , In d 37 0 Shell , Dee r Park , Te x .35 0 Tota l 1,11 7 'Million s o

f pounds pe r yea r o

f 4,4-isopropyildenediprieno l (BPA) . Aristec h was forme d fro m th e chemical s divisio n o f US X b y a December, 1966 , publi c offering . Aristec h ha

s expanded b

y 2 2 miHto

n pounds sinc

e 198 4 throug h a series o

f debottteneckings , an d wil l ad d anothe r 2 0 mHUo n pounds b

y Octobe r 1987 . Oow's capacit y ha s increased fro m 170 millio n pounds sinc e 1964 throug h incrementa l expansions . I n May , 1987 , Genera l Electri c complete d a secon d facilit

y at M L Vernon , wit h approximately 15 0 millio n pounds o f capacity . GE' s productio n i s entirel y captiv e fo r polycarbonat

e resins . Profil e last publishe d 7/16/84 ; thi s revision , 7/27/87 . 

### DEMAN D 1986 : 82 3 millio n pounds ; 1987 : 88 0 millio n pounds ; 1991 : 1,05 0 millio n pounds . (Includes exports) . 

### GROWT H Historica l (1977-1980) : 6. 6 percen t pe r yea n future : 4 t o 6 percen t pe r yea r throug h 1991 . 

### PRIC E Historica l (1956-1987) : High , 91c . pe r pound , polycarbonat e grade , hoope r cars , divd. ; tow, 22%c . pe r pound , epox y grade , bgs. , t.i. , fit . aid . Curren t 77c . t o 87c . pe r pound , epox y grade , hoppe r cars , divd. ; 81 c t o 91c . pe r pound , polycarbonat

e grade , sam e basis . 

### USE S Polycarbonat

e resins , 5 0 percent ; epox y resins , 3 2 percent ; miscellaneous , includin g unsaturate d polyeste r resins , poiysuifon e resins , poiyarylate resin s an d flam e retardants , 6 percent ; exports , 1 2 percent .



# I STRENGT H Polycarbonat

e resins have bee n growin g i n exces s o f 8 percen t pe r year , wit h compac t disc , automobil e an d thermoplasti c alloyin g application s th e mai n drivin g forces . Th e weakene d dolla r ha s create d a considerabl e upswin g i n epox y resi n exports . 

### WEAKNES S Th e epox

y resi n business i s mature , averagin g onl y 2 t o 3 percen t annua l growth ; domesti c epox

y resi n consumptio n wa s dow n 2 percen t i n 1986 . 

### OUTLOO K Newapplication s wil l continu e t o expan d polycarbonat e resin s we

U into th e 1990's . Othe r BPA-base d high-performance resins , suc h a s poiysulfones an d polyarylates , ar e als o expecte d t o take off v althoug h t o som e exten t a t th e expens e o

f polycarbonates . Whil e a U producer

s are basi c i n ra

wmateria l pheno l in d dedicate d t o BPA , tightenin g pheno l availabilit y ma y eventuall y affec t BP

A pricing . , 

# Toxic s Bil l Join s Administratio n o
Th e chemica l an d oi l industrie s joine d th e Reaga n Administratio n las twee k i n urgin g aSenat e subcommitte e t o rejec t propose d legislatio n intende d t o regu lat e an d reduc e th e releas e of toxi c sub stance s int o th e air . Substantia

l progress ha

s bee n mad e i n the reductio n o f ai rtoxic s withi

n the framewor

k o f the existin g Clea

n Ai rAc tan d propose d changes in the sectio n tha tregulates the

m "coul d reduc e publi c healt h protectio

n b y misdirectin g regulator y effort s an d re sources, " sai d Kare

n Shewbart

, environmental managerforDo

w Chemica

l Company' s Texas operations . Testifyin g fo rChemica

l Manufacturer

s Association befor

e the Senate' s environmenta l protection subcommittee , Ms . Shewbar t state d tha

tvolatil e hydrocarbo

n emissions hav e bee n dramaticall y reduced b y th e chemica l industr y durin g th e las ttw o • decades . i Sh e note d tha tatDow , thes e hydrocarbons, whic h include toxi c ai rpollutants , hav e bee n reduced by 50-75 percen tove rthe las t decade . Ms . Shewbar tals o commente

d o n tw o sec tion s o f th e propose

d amendmen

tt o the Clea n AirAc twhic h i s u p fo rreauthorizatio

n

—hazardou

s ai rpollutant

s an d extremely hazardou s ai rpollutants . BILL S SHOUL D PRIORITIZ

E EFFORT

S Sh e said tha tthe objective o

f ai rtoxics legislatio n mustb e t

o prioritize effort

s an d regulat e thos e compound

s whic h hav e the highestlikelihood o

f huma n hazard , an d tha t i s wher e Environmenta

l Protection Agency' s presen teffort s are aimed . "Because o

f the larg e lis to

f compound

s tha twoul d b e regulate

d unde rthis legisla tion , EPA' s effort

s o n prioritize

d compound

s coul d be diminishe

d an d the ne tresultcoul

d b e les s huma

n healt h protectio

n rathe rtha n more, " said Ms. Shewbar

t I n the areao

f extremely hazardou

s ai r pollutants , sh e note

d tha tpropose d change s "duplicat e existin g Federa

l program s whic h address thi s concern, an

d therefore, ar

e no t necessary. " Ms . Shewbar tals o pointe

d ou ttha t"attain in g clean ai rgoal s an

d protecting huma

n healt h depend s o n fine tunin

g an d supportin

g existin g programs , rathertha n th e radica

l restructuring as mandate

d i n thi s bill. " A spokesma

n forAmerica

n Petroleum In stitute said the ai rtoxic s portio n o f the propose d Clea n Ai rAc tamendment

s woul d cre ate bureaucratic confusion, duplication o f existin g programs , regulator y paralysis , liti gation an d delay , an

d coul d actuall y under

mine th e goal s o

f public health . "Th e zero ris k philosph

y embodie d i n thi s bil l will drive azero (air

) emissions polic

y whic h ultimately woul

d lead t o ashutdow

n o f man y industria

l facilitie s i

n this country,' ' said Ear l Arp, directo ro

f healt h an d safety fo rAshlan d Oi l Company

, Inc. , testifyin g for API. Th e proposa l fail s to differentiat

e be ba ; si o tiv
. no so u in r po t Mr . 

# MCCTIM** ^ * » * •***** n • » j =P.2 3



# ro! ST 

# '^ & 

# ? 0 

# c°T^ 

# j[98 9 DIRECTOR

Y O F CHEMICA L PRODUCER S UNITE D STATE S O F AMERICA

Informatio n i n thi s Director y i s fo r th e sol e an d privat e us

e o f sponsor

s o f th e Director y o f Chemica l Producers Program .



# RADIA N LIBRAR Y RESEARC H TRIANGL E PARK , NO33 3 RAVENSWOO D AVENU E

MENL O PARK , CALIFORNI A 9402 5 (415)859-362 7 FAX : (415)326-551 2 TWX : 910-373-204 6 TELEX : 33448 6



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PRODUCT S 198 9 DIRECTOR Y O F CHEMICA L PRODUCER S UNITE D STATE S 

## B
Bismut h oxynitrat e (See : Bismut h subnitrat e unde r Medicina l (Pharmaceutical ) Chemicals ) Bismut h potassiu m tartrat e (Potassiu m bismut h tartrate ) H S A Corporatio n Ardsley , NewYor k Bismut h salicylate , basi c (See : Bismut h subsalicylate unde r Medicinal (Pharmaceutical ) Chemicals ) Bismuth stannat e Ferr o Corporatio n Coatings , Colors , & Electroni c Material s Grou p Transelc o Divisio n Electroni c Cerami c Material s Departmen t M& T Chemical s Inc . Penn Yjn , NewYor k Carrollton , Kentuck

y Bismut h subcarbonat e (See : Medicina l (Pharmaceutical ) Chemicals ) Bismut h subgallat e (See : Medicina l (Pharmaceutical ) Chemicals ) Bismut h subnitrat e (See : Medicina l (Pharmaceutical ) Chemicals ) Bismut h subsalicylat e (See : Medicina l (Pharmaceutical ) Chemicals ) Bismut h titanat e Ferr o Corporatio n Coatings , Colors , & Electroni c Material s Grou p Transelco Divisio n Electroni c Cerami c Material s Departmen t TAM Ceramics , Inc . Pen n Yan , NewYor k Niagara Falls , NewYor k Bismut h trichlorid e (Bismut h chloride ) Th e Procte r & Gambl e Compan y Richardson-Vieks , Inc. , subsidiar y J . T . Bake r Inc. , subsidiar y Phillipsburg , Ne wJerse y Bismut h trihydrat e (See : Bismut h hydroxide ) Bismut h trihydroxid e (See : Bismut h hydroxide ) Bismut h trinitrat e (See : Bismut h nitrate ) Bismut h trioxid e (Bismut h oxide ) (Bismut h yellow ) Ferr o Corporatio n Coatings , Colors , & Electroni c Material s Grou p Transelc o Divisio n Electroni c Cerami c Material s Departmen t Mayfai r Pharmaceutica l Compan y Penic k Corporatio n Th e Procte r & Gambl e Compan y Richardson-Vicks , Inc. , subsidiar y J . T . Bake r Inc. , subsidiar y Th e Shepherd Chemica l Compan y Pen n Yan , Ne wYor k Newark , Ne wJersey Phillipsburg , Ne wJerse y Cincinnati , Ohi o Bismut h yello w(See : Bismut h trioxide ) Bismut h zirconat e Ferro Corporatio n Coatings , Colors , & Electroni c Material s Grou p Transelc o Divisio n Electroni c Cerami c Material s Departmen t TA M Ceramics , Inc . Pen n Yan , Ne wYor k Niagara Falls , Ne

wYor k Bis(neopentylglycol)-1,5-cyclohexanedimethylen e phosphit e Genera l Electri c Compan y G E Plastics Borg-Warne r Chemical s U.S A irg- i C h hemical s Morgantown , Wes t Virgini a Bis(2-octyrj phthalat e (See : Dicapry l phthalat e unde r Plasticizers) Bisfj>entachlero-2,4-cyclopentadien-1-yl ] (See : Dienochio r unde rPesticides) Bis[2,4-pentanedionato ] berylliu m (See : Berylliu m acetylacetonate ) Bis(2,4-pentanedionatO ] cadmiu m (See : Cadmiu m acetylacetonate ) Bis(2 > 4-pentanedionato ] calciu m (See : Calciu m acetylacetonate ) Bis(2,4-pentanedionato ] coppe r (See : Coppe r acetylacetonate (cupric) ) Bisf.2,4-pentanedionato ] lea d (See : Lea d acetylacetonate ) Bi*[2,4-pentaned.onato ] magnesiu m (See : Magnesiu m acetylacetonate ) Bit[2,4-pentanedionato ] manganes e (See : Manganes e acetylacetonate ) Bis(2,4-oentanedionsto]-0,0-nicke J (See : Nicke l acetylacetonate (nickelous H Bis(2,4-oentanedionato ] platinu m (See : Platinu m acetylacetonate ) Bisf2,4-pentanedionato ] potassiu m (See : Potassiu m acetylacetonate ) BisCpentanedionatoJvansdy l (See : Vanadiu m acetylacetonate ) Bis(2,4-pentanedionato ] zin c (See : Zin c acetylacetonate )

Bispheno l A (2.2-Bis(4-hydroxypheny) ] propane ) (p,p Dihydroxydiphenyldimethylmethane ) (0-Oi-p hydroxyphenylpropane ) (4,4'-lsopropylidenediphenol ) Aristec h Chemica l Corporatio n Haverhill , Ohio * Do wChemica l U.S A Freeport , Texa s Genera l Electri c Compan y G E Plastics Moun t Vernon , Indian a Shel l Oi l Compan y Shel l Chemica l Company , divisio n Dee r Park , Ten s
Source : SFt

l Internationa l estimate s a t o r Januar y 1,1989 . TOTA L Annua l Capacit y (Million s o

f Pounds) 19 2 22 S 37 0 35 0 1.13 7

SR I Internationa l 48 7 '*S*f$0W\

.

# KE- 151+ 

# Riegel' s 

# Handboo k o f Industria l Chemistr y SEVENT H EDITIO N

Edited b y 

# Jame s A . Ken t Colleg e o f Engineerin g Michiga n Technologica l Universit y Houghton , Michiga n



# VA N NOSTRAN D REINHOL D COMPAN Y NE W YOR KCINCINNAT I ATLANT A DALLA

S SA N FRANCISC O LONDO N TORONT

O MELBOURN E 

# RADIA N LIBRAR y DURHAM , N.C .Van Nostran d Reinhol d Compan y Regiona l Offices : Ne w Yor k Cincinnati Chicag o Millbrae Dalla s Va n Nostran d Reinhol d Compan y Internationa l Offices : Londo n Toront o Melbourn e Copyrigh t© 197 4 b y Litto n Educationa l Publishing , Inc . Librar y o f Congres s Catalo g Car

d Number : 73-1479 8 ISBN : 0-442-24347- 2 Al l right s reserved . Certai n portion s o f thi s wor k copyrigh t© 196 2 b y Litto n Educationa l Publishing , Inc . N o parto f thi s wor k covere d b y th e copyright s hereo n ma y b e reproduce d o ruse d i n an y for m o rb y an y means-graphic , electronic , o rmechanical , includin g photocopying , recording , taping , o rinformatio n storag e an d retrieval systems-withou twritte n permissio n o f th e publisher . Manufacture d i n th e Unite d State s o f Americ a Publishe d b y Va n Nostran d Reinhol d Compan y 13 5 Wes t50th Street, Ne w York , N.Y . 1002 0 Publishe d simultaneousl y i n Canad ab y Va n Nostran d Reinhol d Ltd . 1 5 1 4 1 3 1 2 1 1 1 0 9 8 7 6 5

Librar y o f Congres s Catalogin g i n Publicatio n Dat a Riegel , Emi l Raymond , 1882-196 3 Riegel' s handboo k o f

industria l chemistry . First-5t h ed . publishe d unde rtitle : Industria l chemistry ; 6t h ed . i n 196 2 unde rtitle : Riegel' s industria l chemistry . Include s bibliographica l references . 1 . Chemistry , Technical . I . Kent , Jame s A. , 1922 - ed . II . Title . III . Title : Handboo k o f industria l . chemistry . TP145.R5 4 197 4 66 0 73-1479 8 ISB N 0442-24347- 2

# I

81 4 RIEGEL' S HANDBOO KO F INDUSTRIA L CHEMISTR Y 

# 7*£ / SVNTHETI C ORGANI C CHEMICAL S 81 6 chlorobenzene , Raschig , an d benzoi c acid . Abou t 6 0 pe r cen t o f th e pheno l produce d i n 196 9 wa s b y th e cumen e process . Al l bu t lh e benzoi c aci d process requir e benzen e a s th e ra wmaterial . Th e benzoi c aci d proces s use s toluen e a

s th e startin g aromati c material . De tail s o f th e pheno l manufacturin g proces s ar e give n i n Chapte r 10 . Som e o f th e majo r use s fo r pheno l ar e dis cusse d below : Phenolic

resins are th e majo r consumers o f pheno l an d shoul d maintai n thi s positio n in definitely . Th e majo r use s fo r phenoli c resin s ar e a s plywoo d adhesive

s an d a

s moldin g resins . Se

e Chapte r 1 0 fo r detail s o n phenoli c resins . Bisphenol

A i s use

d i n th e productio n o f polycarbonate s an d epox y resins , whic h are growin g plastics . Bispheno l A i s i n tur n ob taine d fro m pheno l b y th e followin g reaction : O H 

# o O



### fl + CH3CCH 3

CH , 

### H O 

# O{-O O H

CH , Bisphenol A H 2 0 A flo wshee t fo r bispheno l A manufactur e i s show n i n Fig . 25.34 . Pheno l an d aceton e i n a mola r rati o o f 3: 1 o r 4: 1 are charge d t o a n acid-resistan t stirre d bispheno l A reactor . Glass-line d equipmen t i s use d ordinarily . A sulfur-containin g catalys t i s added,'the n dr y HC I ga s i s bubble d int o th e reactio n mass . Th e temperatur e i s maintaine d a l 3 0 t o 40° C fo r 8-1 2 hours . Th e produc t crystallize s fro m th e reactio n mixtur e t o for m a slurry . A t th e en d o f th e reaction , th e mixtur e i s washed wit h wate r an d treate d wit h jus t enoug h lim e t o neutraliz e th e fre e acid . Vacuu m an d hea

t are applie d t o th e reaction kettle , an d wate r an d pheno l are distille d separatel y fro m th e mixture . Th e batc h i s finishe d b y blowin g th e molte n produc t wit h stea m unde r vacuu m a t 150° C t o remov e th e odo r o f th e sulfur-containin g catalyst . Th e molte n bispheno l A produc t i s quenche d i n a larg e volum e o f water , filtered , an d dried . I t i s a ligh t ta n powder , whic h ma y be furthe r purifie d b y recrystallizatio n fro m solvents . Th e paten t literatur e indicate s tha t ion exchang e resin s promote d wit h variou s mer captan s o r amine s ma y be used i n som e o f th e newe r plant s i n operatio n today . U.S . consumptio n o f bispheno l A durin g 196 9 was 6 4 pe r cen t i n epox y resins , I S pe r cen t i n polycarbonat e resins , an d 2 1 pe r cen t i n othe r uses . Tota l consumptio n was ove r 18 2 millio n pounds . Other products

from phenol

includ e aspirin , alkylate d phenols , chlorinate d phenol s (t o 2,4-D) , an d caprolactam . Chemica l reaction s fo r som e o f thes e material s are show n below : O H ON a O H Importan t by-product s fro m th e chloro benzen e proces s whic h ar e no wsubstantia l volum e chemical s ar e phenylphenols , numer ou s chlorophenols , an d Dowtherm * A ( a eutecti c mixtur e o f dipheny l an d dipheny l oxid e sol d a

s a hea t transfe r medium) .

COON a

Pheno l O 

### I O H
....... . OC—CH , 

# QCOO H 

# -ftgs rrS co 

# ° " Salicyli c Aci d Aspiri n
O H O H O H 

# - o 

# • ~ * •a m 

# •o

>-Alky ! pheno l CH 2 CH 2 R

p-Alky l pheno l
tiMiti 

## 1 1

Lla » I

l l


# ns <v> 

# l i

Wotet r Quenc h Filtratio n ft. Oriin g

Fig
. 25.3 4 Manufactur e o f bispheno l A
. [Pot. Ref.. 38 , A'o
. // , 225 (1959). copyright

1959 by GuffPublishing Co. I O O H O H | [ 

# O*0 a 

# 0 o I OCH,CO H O H O H 9 OCH, C 

### ( ^ ) • ci , 9 

### -^Lr-^V 1 

### qcH.co H r^jc i C l C l

NII,O H C

(2.4-D )

H '

Beckman n rearrangemen t 

## /

s yf H 2 C C 

### \ N H 

### / H,C N ^CH , C H , Caprolaclu m

r o c o'" '



### \

1 I

\

i 

### i i 

# 1 

# I

1 .

i I f 

# i 

# • 1

V i 

# 1

i 

### \ X \\.

y
r v . 

# ! 

# *«m

i

i 

# Surve y o f

Industria l Chemistr y

Phili p J . Chenie r '• Professo r ! | Departmen t o f Chemistr y | University o f Wisconsin-Eau Clair e Ea u Claire , Wisconsi n

A Wiley-Interscienc e Publicatio n JOH N WILE

Y & SON S Ne w Yor k • Chicheste r• Brisban e • Toronto • Singapore P.2 9

BBBBBBBBBBBBBBBBBBBBBBBBBBBBm J aaaaaaaaaaaaaaaaaaaaaaaaaa V

^aaaaaaaaflaaaaa

VCopyrigh t © 198 6 by Joh n Wile

y & Sons , Inc
. All right s reserved
. Publishe dsimultaneousl y i n Canada
. Reproductio n o r

translatio n o i an

y par t o f thi s wor k beyon dtha t

permitte dby Sectio n 10 7 o r 10 8 ofth e 197 6 Unite dState s Copyrigh t Ac t withou t th e permissio n o f th e copyrigh t

owne r i s unlawful
. Request s for permissio n o r

furthe r informatio n shoul db e addresse dl o th e Permission s Department , Joh n Wile y & Sons , Inc
. Library o f

Congres s Catalogin g i n Publicatio n Data : Chenier , Phili p J
. Survey o f industria l chemistry
.
" A Wiley-Interscienc e publication. " Include s bibliographie s an dindex
. 1
. Chemistry , Technical
. I
. Title
. TPI45.C4 4 198 6 ISB N 0-471-01077- 4 66 0 86-781 3 Printe di n th e Unite dState s of

Americ a 1 0 9 8 7 6 :"

> 4 :• » '. ' 118 2 Chemicals trom Propylene and Butylene t o pol y (methy l methacrylate) , a n importan t plasti c know n fo r

it s clarit y an d use da s aglas s substitute
. Th e synthesi s i s outline da s follows
.



# o I I C H 3 -C-CH 3 +

CH , O 

### V I I C H 2 =C-C-OC H HCN—

-

H,< > i -* O H

1 CH.-C-CH , 1 C= N 

## 1 

## -H, 0
• A CH 3 1 C H 2 =C-C= N CH,O H methy l methacrylat e Th e firs t reactio n i s anucleophili c additio n o f HC N t o aketone , th e secon di s adehydratio n o f a n alcohol , an dth e thir di s hydrolysi s o f anitril e t o acarboxyli c aci dan desterificatio n o f th e aci db y methanol
. A n alternat e metho do f makin g methy l methacrylat e i s bein g develope d lha t woul dsynthesiz e i t

mor e directl y fro mpropylene
. Thi s synthesi s i s no t ye t commercial
. I t

involve s reactio n o f

propylen e with carbo n monoxid e an d methano l followe db y a n ai r oxidation
. If

successfu l i t

woul dmak e pol y (methy l methacrylate ) muc h cheaper
. C H 3 - C H = CH 2 + C O + CH 3 O H S*h+ CH S O CH , O \1 1 V 1 1 C H 3 -CH-C-OCH 3 _22_ ^ CH 2 =C-C-OCH 3 + H 2 0 A meta l oxide s Aldo l chemical s refe r

t o avariet y o f

substance s desire dfro maceton e involvin g a n aldo l condensatio n i n aportio n o f thei r synthesis
. Th e mos t importan t

o f thes e chemical s i s methy l isobuty l keton e (MIBK) , acommo n solven t fo r man y plastics , pesticides , adhesives , an dpharmaceuticals
. Approximatel y 0.1 5 billio n l b o f MIB Kwer e mad e i n 1984
. Th e synthesi s is outline dhere
. 

## C^L*<t~is" Acetone 18 3 O I I 2CH,-C-CH , o n O I I 

# -c CH , O I I

I C H 3 -CH-CH 2 -C-CH:»-.I i

MIB K CH : ,

I CH,-C-CH,-C-CH , I O H diaceion e alcoho l

, A C H , O I I I CH.-OCH-C-CH; , mesity l oxid e 

# J-H „

Diaceton e alcoho l i s asolven t use di n hydrauli c lluid s an dprintin g inks
. Recal l tha t

th e aldo l condensatio n i s a n exampl e o l avariet y o f carbanio n reaction s use dl o mak e larg e molecule s fro msmalle r ones . A n aldehyd e o r

a keton e wit h a t

leas t on e hydroge n o n th e curlxi n nex t t o th e carbony l will reac t t o giv e th e aldo l condensation
. Th e mechanis mi s give n a s follows
.



## e :O H 

## e

'- CH,

- 

## e n +/CH 2 -C-CH, , () :

I I C-CH ; , + HAY 

### :6- & 

### O I I

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

I I

I C H 3 -C-CH 2 -C-CH , + H 2 0 : I CH 3 CH 3 O H :( ) I I

I 'CH,-C-CH a -C-CH , I C H , 

## e

+ O H Finally , bispheno l A i s manufacture db y areactio n betwee n pheno l an d acetone , th e tw o product s fro mth e cumen e hydroperoxid e rearrangement . Bispheno l A i s a n importan t dio l monome r

use di n th e synthesi s o f Polycarbonate s an depox y resin s a s w e wil l se e later
. Ove r ahal f billio n Pound s pe r

yea r o f thi s chemica l i s made
. CH , 

# ! 

# »^0 > CH , I 3 * 0= C I CH , 

# '•HOH-C^"' 0 CH , bispheno l A

# Klau s Weissermel Hans-Jiirge n Arp e 

# Industria l Organi c Chemistry Importan t Ra w Material s an d Intermediate s Translate db

y Alexander Mulle n



# Verla g Chemi e • Weinhei

m• Ne w Yor k 197 8

*Prof

. Dr
. Klau s Weissermel Dr
. Hans-Jiirge n Arp e Hoechs t AG Postfac h 800 3 20 D-623 0 Frankfur

t 8 0 West Germany 

# Prefac e

Copy Editing : Dr
. Han s F
. Ebel
Thi s boo k

contain s 4 3 Table s
CIP-Kurztitelaufnahme de r Deutschen Bibliothek Weissermel , Klau s Industrial organi c chemistry : important ra w material s andintermediate s / Klau s Weissermel ; Hans-Jiirge n Arpe
. - l.Aufl
. - Weinheim , Ne w York : Verlag Chemie , 1978
. Dt
. Ausg
. u.d.T. : Weissermel
. Klaus : Industrielleorganisch e Chemie
. ISB N 3-527-25706- 3 (Weinheim) ISB N 0-89573-005- 7 (Ne

w York ) NE : Arpe , Hans-Jiirgen : © Verlag Chemi e GmbH , D-694 0 Weinheim , 197 8 Al l right s reserve d(includin g thos e o f translatio n into foreign languages)
. N o par t o f thi s book ma y b e reproduce di

n an y for m- b y photoprint , microfilm , o r an y othe r mean s - no r

transmitte dor

translate dinto amachine languag e without written permissio n fro

mth e publishers
. Registere dnames , trademarks , etc . usedi n thi s book , eve

n withou t specific indicatio n thereof , are not t o b e considere d unprotecte db

y law
. Printer : Passavi aDruckere i Gmb H Passa u Printe d i n Wes

t German y Industria l organi c c a s wel l as , t o a n i m presen t statu s o f ki Ther e wa s thu s ag r an dintermediate s an dt o presen t

i t i n development , whi c fro mthei r

industri a in g discussion s wit ! Thi s boo k

address e fro mi t th e chemis t manufacturin g pro i glea n informatio n ; an dfeedstock s aio

discipline s i

n th e c economist s - wil l 1 economi c interre d Thi s boo k

i s arran g thei r tightes t possi l unavoidable
. Th e i A s arule , th e ma m men t an dsignifie s application s o

f th e | product s ar e freq u existin g technologi c mor e economi c o r

i Th e author s endea ' informatio n ar e a t 1
. Th e mai n text . ' ! 2
. Th e synopsi s of ' 3
. Flo w diagram s i

l Thes e thre e type s o o r makin g brie f

n o note s whic h briefl y t o b e rapidl y infor t31 4 13. Benzene Derivatives

applicatio n o

f phenol : 1
. phenoli c resin s Wapolycondensatio n wit h HCHO , wit

h hydroxymethylphenol s a s precursor s O H CH

2 O H

productio n o

f phenoplast s (i n l,000t) : 197 4 197 5 197 6 US A 72 5 57 8 70 8 Japa n 23 9 19 6 25 4 W.German y 17 6 14 3 16 6

2
. E-caprolactamwit

h K A precursor s 

# (5° multi-stag e (CH 2)
.

3
. bisphenol-A , A = aceton e (bisphenol-B , B = butanon e bisphenol-F , F=

= formaldehyd e commerciall y les s important ) onc e again
. Th e Hock variant i s thu s multi-stag e but

free fro m co-product
. 13.2.1.3 . Phenol Applications an d Secondar

y Product s Th e pheno l consumptio n i n th e USA , Japan , andWester n Europ e ca

n b e summarize dwit

h regardt o applicatio n area s a s liste di n Tabl e 13-4 : Tabl e 13-4 . Pheno l Application s i n USA , Japan , an d Wester n Europ e (i n %)
.

US A 197 2 Pheno l resin s 5 0 e-Caprolacta

m2 0 Bisphenol- A 1 0 Adipi c aci d5 Alkylphenol s 5 Various' ) 1 0

' ) e.g. aniline , plasticizers , 197 6 4 6 1 4 1 4 3 J 2 3 Japan

197 2 5 4

- 2 4

- 5 1 7 antioxidants , etc. 197 6

5 0

- 2 6

- 4 2 0 W
. Europ e

197 2 3 3 3 0 1 3 1 3 1 1

Accordin g t o th e above , phenoli c resin s o r phenoplast s - th e polycondensatio n product s o f pheno l wit

h formaldehyde-pos

ses s th e greates t

importanc e i

n thes e countries
. They serv e in , fo r example , th e manufacture o f paints , adhesives , molding mate
rials , andfoa

mplastics
. Th e productio n figure s fo r phenoli c plastic s i n th e USA , Japan , an dW
. German y are summarize di n th e adjacent

table
. Th e manufacture o

f e-caprolacta

mrank s secondin th e US A andWestern Europe
. However in Japan , e-Caprolacta

mpro ductio n is base dsolely on cyclohexane
. For th e sam e reason , adipi c aci di s no t

manufacture dfro

mpheno l in Japan , becaus e e-caprolacta

mandadipi c aci dare produce di n othe r countrie s fro mpheno l via th e same intermediate , cyclohexanol
. 2,2-Bis-(4-hydroxyphenyl)-propane , th e thirdlarges t con sumer o f phenol , i s know n a s bisphenol- A o r dia n o n account

o f it s productio n fro

mpheno l andaceton e (eq
. 21)
. Th e availabl e productio n figure s fo

r bisphenol- A i

n th e US A andJapan are liste di n th e adjacent

table
. Th e presen t

productio n capacit

y i n W
. German y i s estimate dt o b e approx . 55,00 0 t/a
. Th e condensatio n o

f aceton e wit

h exces s pheno l ca

n b e con ducte deithe r

continuousl y o r

discontinuously i

n th e presenc e o

f H 2 S0 4 c

catalys t carrie do Accordi i systemc .

2 HO Y

Bisphen c resin s ar fro mth e Thes e e t bein g ha i nate s a r phosgen e Polysulf c dipheny l Th e add i tio n is g tbu t free from

•duct s an dWestern ition area s a s 13.2. Oxidation and Secondary Products of

Benzene 31 5
H 2 S0 4 or , accordin g t o th e Hooke r process , wit

h dr y HC I a s catalys t andmethylmercapta

n a s promoter . Th e reactio n i s carrie dout

a t approx . 5 0 °C , th e yieldbein g almos t quantitative
. Accordin g to th e UC C proces s als o aheterogeneou s catalys t syste mca n b e employed :

2 H O .CH ,

+ o= c [H* ] CH , C H
CH , + H 2 0 (21 ) productio n o f bisphenol- A (i n 1,0001) : 197 4 197 5 197 6 US A 16 8 13 3 19 1 Japa n 5 1 4 0 n.a . n.a . = no t

availabl e manufactur e o

f bisphenol-A : acetone-pheno l condensation , catalyst : H,S0 4

HC I (Hooker ) promoter : CH 3 S H

W
. Europ e 197 2 3 3 3 0 1 3 1 3 1 1
jplast s - th e ehyde-pos

yservein.fo r oldin g mate
fo r phenoli c immarize di

n i n th e US A olacta mpro lin e reason , pan , becaus e ie r countrie s inol
. larges t con j n account o f Tie availabl e n dJapa n ar e • n capacit y i n a . ca n b e con e presenc e o

f Bisphenol- A i s widel y use di n th e manufacture o

f syntheti c resin s an dthermoplastics
. Bisphenol-A-glycidy l ether s resul t fro mth e reactio n betwee n bisphenol- A andepichlorohydrin
. Thes e ether s are th e basi s o f epox y resin s whic

h are capabl e o

f being hardene d(cf. Sectio n 11.2.1)
. Thermoplasti c polycarbo

nate s are obtaine db

y condensatio n o

f bisphenol- A wit

h phosgen e or

b y transesterificatio n wit

h dipheny l carbonate
. Polysulfone s are obtaine db y reactin g wit

h 4,4'-dichloro

diphenylsulfone
. Th e additio n o

f olefin s t o pheno l yield s alkylphenols
. Th e reac tio n i s generally conducte din th e liqui dphas e a t 50° C wit h equimola r amount s o

f reactant s andBF 3 or

H Fa s catalyst
. Isooctyl , isononyl , andisododecyclphenol s posses s th e greates t importanc e sinc e they ca

n b e produce dfro

mth e chea

p olefins , diisobutene , tri

- an dtetrapropene . Thes e long-chai n phenol s are ethoxylate da t th e O H group s wit h ethylen e oxide (cf. Sectio n 7.2.2 ) fo r thei r applicatio n a s non-ioni c detergents , wettin g agents , an demulsifying agents . Furthermore , the y ar e als o use da s additive s fo r cuttin g oil an d as auxiliar y product s i

n rubbe r andplasti c processing
. Thei r surfactant propertie s ca

n b e reinforce db

y sulfonation
. How

ever , the y are markedl y decreasin g in importanc e du e t o thei r resistanc e t o biologica

l degradation
. Recently , o-creso l and2,6-xyleno l hav e foundgreate r applica

tion , wit h th e result

that th e deman dfo

r o-creso l couldn o longe r b e me t solel y fro mpetroleu man dta

r distillate sources . Manufacturin g processe s ha dt o b e develope dfo

r 2,6-xyleno l a s i t is not foun di n natural products
. Bot h product s are manufacture di n th e liqui dphas e b

y methyla

tio n o f pheno l wit

h methanol
. Thi s reactio n i s carrie dou t i n th e applicatio n o

f bisphenol- A i

n reactions : 3.1
. wit h epichlorohydri n formin g epox y re sin precursor s 3.2
. wit h COCl 2 t o polycarbonate s

t o polysulfone s -C l

4
. alkylphenol s 4.1
. highe r

alkylphenols : manufactur e via catalyti c pheno l alkyla

tio n wit h olefin s i

n liqui dphas e

Rgenerall y KO-C 8 H, 7

/'so-C s H 1 9 «o-C 12 H 2 5 application s o

f alkylphenols : after E O additio n (ethoxylation) : wettin g agent s emulsifyin g agent s (non-ionic ) detergent s wit

h limite dbiological degrad

ability additiona l sulfonatio n increase s surfactan t propertie s 4.2
. methyl

- an ddimethylphenol : manufactur e via: heterogeneousl y catalyze dliquid-phas e methylatio n o

f pheno l wit

h methano lP.3 6



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# - ' 

# ,.. s tfdfn/cii/ Ptffi/rtefd

Smm&$4<£ FEBRUAR Y 198

8 4 ^ Pievfo wRepor t —Octobe r 198 5 A Reportin g Servic e o f Mannsvill e Chemica l Product s Corp . Asbur y Perk , NJ 07712-027 1 

### BISPHENO L A FOCUS....Bispheno l A

(abbreviate dBPA ) i s a primary rat i materia l for th e productio no f polycarbonat e (PC) , epoxy , bispheno l A-formaldehyde , phenoxy , an d high-performanc e resin s including polyesters , polyacrylates , an dpolysulfones . Polycarbonate s hav e outpace depoxie s a s th e larges t derivativ e o f BPA . Althoughepox y resi nmarket s ar e relativel y mature , moa t engineerin g plastic s an d high-performanc e resin s continu e t o hav e highrate s o f consumptio ngrowt ha s meta l replacement s i n automotive , applianc e an d electroni c appli cations . B

y th e 1990' s P C ma

y becom e the larges t volum

e engineerin g plastic , excluding possibl y nylon . Wit ha highleve l o f exports , U S productio no f bispheno l A exceede don e billio npound s i n 1987 . AlthoughU.S . 196 7 BP A outpu t increase db

y abou t 5 % compare dt o 1986 , apparen t domesti c deman dremaine d relativel y

static , base do

n availabl e preliminary productio nreport s fro m th e U S Internationa l Trad e Com mission . Base do n historica l comparison s an d extrapolatio no f eatimate d BP A consumptio nincrease s for msjo r derivBtive s fo r 1987 , i t i s quit e possibl e ths t th e fina l repor t o f productio nfo r 198 7 wil l b e abou t 1 0 percen t highe r thanthe preliminary data . Base do

n variou s trad e report s sn d estimates , U S outpu t o f polycarbonat e resin s i n 198 7 increase db y 8-10% . Growt hfo r P C resin s ha s bee ni n establishe dmarket s a s wel l a s i n emergin g market s including medical , packaging , film , an d alloy s an

d blends . In additio nt o a hig hrat e o f growt hfor P C resins , epox y resi nproductio nreportedl y increase db

y abou t 8 % i n 1987 . I n additio nt o highe r domesti c consumptio no f epoxies , export s increased . OUTLOOK....Consumptio no f epox y resin s wil l hav e onl y limite dfutur e growt hi n en d use s suc ha s protectiv e coating s an

d adhesives . However , ther e wil l be growt hfo r electrical/electroni c application s fo r epoxie s i nfiber-reinforce dlaminate s fo r printe dcircui t board s an d encapsulation s fo

r electroni c devices . Demandfo

r polycarbonate s ros e dramaticall y durin g the 1970's , wit hestimate dU S consumptio nin th e rang e o f one-qusrte r billio npound s b y 1980 . Deman

dfo r polycarbonate s wa s relativel y stati c durin g th e earl y yeer a o f th e 1980's . B y 1987 , U S polycarbonat e deman dwa s almos t 40 0 millio npounds . Majo r deman d growt hfor P C ha s bee ni n automotiv e an d safet y glazing . Electronic s an d communication s als o contribute d t o strong growth , particularl y us e fo r busines s machin e houaing s an d compac t discs . Base dmsinl y o n a high" ! leve l o f growt hfor P C resins , overal l U S BP A consumptio nwil l probabl y increas e b

y abou t 6 % annuall y

ove r ] th e nex t five yea r period . PRICING....Captiv e consumptio nfo r epoxy , polycarbonate , an d specialt y

resi nmanufactur e account s fo r wel l ove r one-hal f o f U S biapheno l A demand . Therefore , i t i s difficul t t o determin e wha t BPA transfe r value s ar e assigne dfo

r interna l uae . Mos t merchan t marke t aale s ar e t o large-volum e resi nproducer s a t negoti ate dprices . Fo r thi s reason , publiahe dlis t price s generall y d o no t reflec t actua l selling prices . Lis t price s ar e subjec t t o variou s temporary voluntary

allowance s a s reflecte di n th e averag e sale s valu e a a reporte db

y th e USITC . Th e actua l selling pric e o f BP A wil l probabl y

increas e moderatel y

i n the future . AVERAG E PRIC E RANGE - BISPHENO L A Cent s Pe r Pound• TL/C L (Hopper ) - Freigh t Allowe d- Epox y Grad e Trsd e Lis t Avg . Sale s 196 0



### "29 J 2 7 196 5 2 1 197 0 

## ~Zo T 1 7 197 5 

### ~52 T 3 3 198 0 

## TT 4 8 198 4 

## ST 4 8 198 5 

## TT 4 8 198 6 

# sr 4 3 198 7 198 8



## ST 198 9 

### -9T T 199 1 

### "9T T Th e lis t pric e fo

r polycarbonat e grad e i s 4 cent s pe r poun dhigher . SUPPL YAN D DEMAND....Million s o f Pounds....Estimated....Domesti c U S Capacit y Productio n Merchan t Sale s Import s Export s Demand 196 0



### 5 1 196 5 

### -T5f f 9 7
9 7 197 0 ~27 D 

### 20 2
202 197 5 "52 5 

### 293 9 7 293 198 0 

### 840 530 130 4 0 49 0 198 4 

### ~BS 5 76 2 31 8 4 2 720 198 5 

### 895 94 9 330 6 2 887 198 6 

### 73 0 956 34 1 7 9 87 7 198 7 

### TT3 7 100 0 

### n/ a 2 11 2 89 0 198 8 

### TI3 7

95 0 198 9

100 0 199 1

115 0 Import s o f bispheno l A , separatel y reporte db

y the U S Burea uo f Census , wer e les s tha n1/ 2 millio n pound s pe r yea r befor e 1987 . Export s o f BP A wer e no t separatel y

reporte dbefor e 1984 . Export s for 198 0 ar e estimated . AVAILABILITY....Shortage s o f cumene-derive d pheno l ra w materia l coul ddevelop . However , i t i s no t antici pate dtha t bispheno l A suppl y wil l b e affected . fAl l U S producer s o f BP A als o manufactur e pheno l an d woul d probabl y giv e suppl y

preferenc e t o making ra w materia l availabl e t o manufactur e highe r valu e adde dderiva tive s suc ha s BPA. } Producer s o f BP A hav e generall y

mad e recen t increase s in pheno l capacit y o r hav e plan s fo r futur e expansion s sn d debottleneckin g whic hshoul deneur e supply . Fro m th e standpoin t o f nameplat e operatin g plan t siz e fo r bispheno l A , ther e appear s t o be adequat e U S capacit y fo r the nex t fe

w yeara . Wit hmoderate ddomesti c demandgrowt han d a n anticipate ddeclin e i n exports , U S producer s ma y no t hav e t o mak e an y majo r capacit y

addition s unti l th e 1990'a . However , G E i s studying th e constructio no f a new facilit y i n Alabama . [U S export s o f BPA ar e expecte dt o declin e a s mor e capacit y i s installe doverseee. j Genera l Electri c Co . en dMitsu i Petrochemica l formeda join t ventur e t o mak e BP A i n Japan . Genera l Elec tri c Plastic s Europ e als o ha s a BP A plan t unde r constructio ni n th e Netherlands . I n Brazil , Rhodia , th e subsidiary

o f France' 8 Rhone-Poulenc , i s expanding BPA capacit y t o 30,00 0 metri c ton s pe r year . 8/8 6P.3 8



### PRODUCER S AM ) CAPACITIE S - BlSHPtfctTM ^ -^LION S O F POUND S PRODUCE RLOCATIO N ''

i 198 8 CAPACIT Y Aristec hHaverhill , O H ' • 15 2 ~iz<£ i-,g~ , Do w Chemica l Freeport , TX22 5 Genera l Electri c Mt . Vernon , IN 37 0 Shel l Chemica l Dee r Parte , T X35 0 TOTA L 113 7 Base donannounce dcapacitie s an dtrad e estimates . Aristec hwa s forme dfro m th e chemica l divisio no f US Xandha s bee nexpandin g i nstage s t o abou t 19 2 m m lbs . Aristec hplan a a furthe r increas e i n198 9 t o abou t 22 8 millio npound s throug hdebottlenecking . Dow in crease dcapacit y

incrementall y

t o abou t 22 5 millio npound s i n1986 . Do w may mak e a furthe r majo r expansion . Wit hthe completio no f a secondfacilit y at Mt . Vernon , IN

i nearl y 1987 , GE' s capacit y

wa s increase db

y abou t 15 0 millio npounds . G E i s reportedl y considerin g th e constructio no f a

nentirel y

new BPA facilit y i nAlabama . G E use s al l materia l captively . EN D USES....Bispheno l A (BPA) , als o referre dt o a a 2,2-bis(p-hydroxyphenyl ) propan e an d4, 4 isopropyl idenediphenol , i s a monome r use dt o produc e epoxy , polycarbonate , BPA-formaldehyde , phenoxy , polyester , sn dothe r resins . I t als o function s a s a chemica l intermediat e sinc e i t ca nb e readil y halogenated , hydro gen s ted , andsulfonated . Application s fo r variou s resin s an dderivative s o f BP

A includ e th e construction , automotive , aircraft , appliance , an delectroni c industries . BPA is s crystalline , prilled , o r flak e materia l wit ha mil dphenoli c odor . Do w introduce da granu late dfor

m i n1987 . I t i s solubl e i nalcoho l an dacetone , slightl y

solubl e i ncarbo ntetrachloride , practicall y

insolubl e i nwster , bu t solubl e i naqueou s alkalin e solutions . Commercially , bispheno l A is availabl e i nbot hepox

y andhigher-purit y

polycarbonat e grades , sol dat a highe r price . Th e polycarbonat e grad e i s als o use dfo r polysulfon e resins . Fo r makin g epox y resins , andmos t othe r uses , th e epox y grad e i s usuBll y

suitable . Polycarbonat e resins , mad e b y reactin g bispheno l A

wit hphosgen e (carbony l chloride) , ar e water-white , impact-resistan t thermoplasti c polymer s use dfo r high-performanc e moldings , shatterproo f windo w glazing , anda vsriet y

o f specialties . Polycarbonate a ar e no w th e majo r derivativ e o f BPA . Epox y resins , previousl y

th e larges t outle t fo r BPA , ar e commonl y th e reactio nproduct s o f a polyhy dri c pheno l an

da chlorohydri nor simpl e epoxide . Th e majo r commercia l epox y i s obtaine dusin g bispheno l A sndepichlorohydri na s th e reactants . Epox y resin s provid e toughness , corrosio nresistance , adhesion , and electrica l insulation , amon g othe r properties . Epoxie s ar e widel y use di nprotectiv e coatings , adhesives , andplastics . Epox

y resin s ar e als o widel y

use di nlaminatin g printe dcircui t board s andfor encapsulatin g electrica l devicee . Phenoxy resin s ar e produce db

y th e copolymerizatio no f BP A sndepichlorohydri nbut , unlik e epoxies , d o no t requir e esterificatio nwit hlong-chai nunsaturate dacid s o r reactio nwit hamide e o r amine s t o produc e cure dresins . Coating s base donphenox y resin s ar e toughandhav e excellen t adhesion . Bispheno l A-formaldehyd e resin s ar e use di nspecialt y applications , includin g inks , coatings , var nishes , an

dabrasiv e binders . Polyester s ar e prepare dfro m BP A andanalkalen e oxid e suc ha s propylen e ox ide . The glyco l produce di nth e reactio nca nb e eaterifie dwit hmalei c or othe r dibasi c acids . Thes e poly ester s hav e excellen t chemica l resistanc e an dca nb e laminate dwit hglas s fibe r t o fabricat e corrosion resistan t chemica l proces s equipment . Tetrabromobiepheno l A , th e principa l halogenate dderivativ e o f BPA , ha s flame-retardan t applications . EN D US E PATTER N - 198 7 ESTIMAT E DERIVATIV E PERCEN T Polycarbonat e Resin s 5 3 Epox y Resin a 3 7 Tetrabromobiepheno l A

2 Miscellaneou s 5 MANUFACTURING....Abou t 0.8 8 poun do f pheno l i s require dt o produc e on e poundo f bispheno l A , wit habou t 0.2 8 poun do f aceton e needed . Bispheno l A i s produce db

y th e condensatio no f two mole s o f pheno l wit hon e mol e o f acetone . Exces s pheno l is reacte dwit haceton e i nth e presenc e o f anaci dcatalyst , usin g a smal l amoun t o f a catalyst - promote r suc ha s methy l mercaptan . Th e catalyst , dry hydroge nchlorid e gas , i s bubble dthroug hth e mixtur e fo r severa l hour s an dth e reactio ntemperatur e i s controlled . Afte r reaction , crud e produc t i s strippe do f HC I sn dwate r o f reaction . Recovere dHC I an dexces s pheno l ar e recycled . Crud e BP A is droppe da s a slurr y

int o still s fo r purification . Th e slurr y i s washe dwit hwater , neutral ize dwit hmil k o f lima , an ddistille dunde r vacuu m a t temperature s u

pt o 150°C . Th e molte nproduc t remain in g i nth e stil l i a sparge dwit hstea m a t 150° C t o remov e fina l trace s o f th e odorou s mercapta npromoter . Th e deodorize dmel t i s the nquenche di nwater , washed , filtered , snddried . Whil e bispheno l A

plant s ar e comparativel y simple , th e productio no f BP A i s s delicat e proces s sinc e a numbe r o f isomer s andtri - o r mono-hydroxy byproduct s ar e formed . Whil e a produc t containin g thes e im puritie s may

b e use dfo r th e manufactur e o f epox y resins , i t i s no t suitabl e fo r polycarbonates . Earl y batc hprocesse s eliminate dthes e impuritie s b y high-cos t crystallization . Newe r processe s employ distilla tio nandextractiv e crystallizatio nunde r pressur e t o purif y crud e bispheno l A

continuously . Thi s greatl y improve s th e economics . Distillatio no f BPA i s especiall y

difficul t becaus e numerou s elements , some i n minut e concentrations , decompos e th e produc t o r promot e th e formatio no f polymer s sndtar . ENVIRONMENTA L ASPECTS....Bispheno l A i s irritatin g t o ski nandeyes . Th e soli dmateria l i s a nirritatin g dua t an dca nirritat e uppe r respirator y passsges . Th e EP

A ha s propose dtest s o f pulmonar y effect s a s wel l as aquati c toxicity . The ingestio ntoxicit y o f BP A i s very low , bu t ingestio nshoul db e minimized . T o th e bes t o f ou r knowledge , th e informatio ncontaine dherei ni s accurate . However , we d o no t assume an

y liabilit y

whatsoeve r fo r th e completenes s or accurac y o f thi s report .