Amination process

173 Pages·2007·4.99 MB·English

by  Elbert C. Herrick

“tn; industria! serena Process oe ure |

) Fvaiuation Series +
AZ

mo

Toxic Pollutant
identification:
AMINATION PROCESSES

a =U
J

U.S. ENVIRONMENTAL PROTECTION AGENCY
ela

Wa ~ DEUCE Series

‘TORIC POULUEAME IDENTTEICATTON:
SAUFATION ?ROCESSES

be
ELBERT C. RERRICE

JO a. Ke

‘The MITRE Coxporation
METRE Dtvéston

Metesn, Virsinia 22101

Grant Wo. 205629

Technical advisor: Psul E, desRosiers

Project Officer: Davia a,

seeing, {83L-cr

1.8. ENVIZONARTEAL PROTECTION AGRNCT
TODUSTREAL aRD EXTRACTIVE PROCESSES DIVISION
OFFICE OF ERGY, MINERALS AD EIDUSTRE
OFFLCS OF RESEAAGL a TEVSLORENE
‘WASHINGTON, D.C. 20480
soSTRACE
Tuis study provides a anvivonmeatal evaluation of autnatton Sy
amconolyaie, a very #ideiy used unit preeaea in te chemicsl industry,

42 representative exanples of this unit pracess ve have considered

4 depth the fommatton of nethylanines fron wethanol, of sthylamines
from ethanol, of aniline from phenol, of echanolamines fzoc athylene

peide, and echylenedisaine from ettyiana d¢chloride and

soe ethan
clamine, Process descriptions with flay diagrams ara presented and

compared for the six pracssses. The constituents of che waste dte=

charges have been Lfenttfied and cabuloted az te type, with the p

seutces located on the Flow diagram of each process. The treatoent
aed disposal of the waste discharges from the aix aninscion arosseses

are pragenced 4a teens of chs

gegregated sofet source dischazzes.

Shove on

2 ara shova co have severa? commen chemical pal:

ta emissions sad ather vaste discharges. Anisartoa Ly mucnctyste
processes, in genera?, are considerad to fal into three groupe,

ubich have chevasteriatic types of stemteal

charges

E
UGLE CF contents

Gist oF FTGcRES
LIST oF CABLES
ERICUTUTE SUCRE

Lo

GENERAL TESCRIPTTON CP THE "ROCESS CP antTNaTTON
Be aMWOHOLESIS

Led Types of amenclytic Geactton

IE Greuplag Cased on Behavicr of Ammoria
1.21 Dovble decomosiczen

112.2 desperation

1202 Simple adaitdon

LDA Meletste aetivsty

Sichertem of che Ammosolysie of A2cohois

Tysieal Examples of amtretton by Amouo:

E41 Uetkylamiaes fon Methane)

1lQ.2 Meqefacesve of Zthylamines

L413 Mancfagtare of Anitine by Amconolysia

ef Phenok

L.44 Nemfacture cf Zthenslsataes by

amorelysis of Bchytene Oxfee

1.3 GlfGecerces Betuess amination 2f vdeeay— and
Chierevaliznatice
1.3.1 staylesacianise faq Gehylene Dichioelde
TIE2 Ethylececionise fon fchanolaciee

1.6 Amine Syrtkesis Sy ycregersetun of Vitea
Compounds

sata

PROCESS 2ESCRIETIONE

2. Mathylamines

zig ceenare
Erocess
2.ld Methylamices
of Defers
Ziidul bealyeteet Dace ox Yesceetes
Discherges at che Belle Plant
2.1.4 Yethylenizes Process et che DuPent
Rouscon Zant
Eld1 dnsiytic Dave or Yasteveter
Dischtegad ze the Eeusson
past

‘roeeas se the Selle Plant

a0
coNTERTS (Continued)

2 Rthylamines from Ethanol

3 aniline tamufacture 97 Anmozo1ysie 0 Paenol

4 onufaccure of Ethanolamizes by Amonolysts

of Ethylene Oxide

2.5 Yacufacture of Eehtlenadianine by
Samorolysta of Brhylene bichlorzde

2.6 Wanufacture of Etksleaedismine be Amoaolyeis
of Rttacolenine

EVALUATION CP STA PROCESSES USING ANTUATLON OF
SMMOWLYSTS BOR DISCHARGE $DUARITIES

3.1 Comparison of Flowstivets
3.2 Conpactzcn of Gougtitueacs of sir. Mater, and

Selid Diveliargas from 3elaced Discharge Peins3

in the Siz Acinetiun by Amonoifsis Processes

3.2.1 Discharges from tae Yethy-artnes

3.2.2 Discharges from the Ethy-an‘uee 2recsss

Discharges from the Manufacture
aniline by amonolysis af Phenol
Discharges from che Manutseture of
Echeno lemines Sy the anenno sis
Echylane oxide
Discharges tom the Uanufacture
Hehylenatiamine by the scnenclysis of
Erhylene Dichloride
gee fran the Manufacture o:

etiemine 3y the dcmenolyats of
realgation af Sinllavittes ang 0°¥s imilariz
of Lischerges fren $1x Nelecead Acinations by
dunans:yeis

3.2.3

STatE-OFLTUE-ANT DISCHARGE TREATIENT £30
FOR S2X SELECTED ANIMATIONS 3Y AMOK

2 Ade Potlutica Controls
2 ater Fallctton Controls
3 Solid Waste Treetzont and Disposal

rs
rs
TABLE OF (ONTENTY (Consus

5.0 cOvCLUSLONS

Sonmonality of Waste D1echarges
Extent of the Procese of amination by
senoaolyata fn the C.8. Organ‘ Chantel
industry Pa
5.3 Tae of DMesiaiarities in aate Elacharges

asa Basis for Divielen cf asinasten

Procesaea into Belated Groups Bt
BIBLIOGRAPHY ”
ASPEREUCES _

J2PEIDZE ~ CORRESPONDENCE
LAST OF cones

Rae

Leenard Pracess for Methylamines
Methylamines Wanufacture, Belle Plant
Metbylemines Manufacture,

Houston Plant

Lwonard Process for the Manufacture
of Ethylanines

Scientific Destgn Praces:
of aniline from Phen?
Sedentiiie Design Process Zor Menufscture
af Ethanolamines from Sthyleae Oxide
Process Zor Manufacture of Bthylenedianiae
from Ethylene Dichloride sné Amouia
Apperatua for the Seperation of

uthylene Diettoride and amonia

Leonard Process for Yenezaccure of
Ethylenediazine from Wance*hanolamize

Manufacture

Methylanines damyfacture, Belle Plane
Ueonard Process for the asufacture
of Hthylamises

Process Sve tenubactore

Phenol

fe Design Procest ‘or Yerutactar=

plane @xids

Process for Wamufactura of Echylanaciznine

ftom Ethyluae Ofshloride and Amonta

Apparatus for the Sezaration cf

Etnylenadlacine from Crvda Peodict

Leonatd Proeaes for saeeZaczure of
wlenaiianine from Hoscethanolanize

Selected iminstions 3 anmone:
Nethylamines Menufacture, Be:
Geonard Procese Zot che Menufctace
of ehylastnes

Scientific Design Process for Maxafacture
of aniline from Phenol,

Beleactfte Design Process For Mensfscture
of Ethanolentnes ftom Ethylene Dnide

Appsratss for the Sepa
Ethylened ‘ante ivoz Cvude 2cocae2
Leonard Pisces for Mamufactsra 3¢

Uehyloved‘enine fron Monoethaae“amine

vit
LIST OF tamLes

‘able tumber

ut Phystea? Properties of Mechylacines
an enysiced of ediylseines az
13 Eraperties of satltae a
ne Properties of tlaaaiarines Le
us Phyateat Properties of Echyleneltarine
snd Hegher sth teneectoee 128
at Methylaxines Zeoceaa, Jeacewater, Selle
Plaot fo. £ Oeiydrator Socters, 4/29/75
of2/35 cars
2.2 Nethylenfacs Pracecs, Kastewater, Belle
Plate to, 2 Debydrstor Yoetons, 4/29/73
2s
23 wines Preesse, Wastewater, eile
Plant a. 1 Yethenel Recovers Celuna
Botsous, £/29/75=6/2/75 218
ba AMethylanines Process, Kastoxnter, Selle
Plane So. 2 Metaecel Secovery Coluan
Jortoms, $/12/75-4/2/75
2s Yethylanines Peoesse, Kasteunter,
fest Deiyerecce 2attona, 4/25/)
26 wastenater, Balle
Pian Discharge fren Five 200 sen
Cuspared to Déscherge
SYA T538)275
he Hethyieines Procace
e Unetowater Teoctment ewer, 4/28.
si2e78 220
28 sec. Wactexater, Hevetae
Bectome, 2/2/7502) 10/7
28 nylazines Process, Wsstewater, 3

ken,

ator 2cttona, 2/2/7

=soH
Methylamines Pracees, Uaseavecer, Zouatan
Plast Methanol Zesevsey Golvany 3/5/75
BATTS & 4/20/75-2)26/ 75
Metiylamines Procass, estevecer, Zoustyn
Plant Tume Scrubber Tenk, 2/3/75-2/23/73

& 3/20/7504 18/75 28
Methvlomines Process, Yasteweter, Houston
Plant Cooling Teter Blovéown, 3 Seaples

Between 2/5/75-2/26/
LAST OF TABLES (Concluded)

Yethylanines Process, Wastewater, fous732
Plant, Steam Purp Condensate, 8 Secpies
Between 2/5/75-4/16/75

Comarigon cf Resul=2, Houston Pleat

ys. Belle Plant, wast Loads Teduletec

as Zounds per Y Pounds of Autaee Produces
Houston Plart, Historical TOD Teta

Comparison ¢f Acumnsiyais Processes
Pollutant Otscharges from the Hetiylantnes
Process

Pollutant Discharges from the fthylamines
Process

Pollutant Discharges fron the Matufae 2
of aniline by Amonelysis of Phenol
Pollutaat dtacharges from tne Manufa
of Eehanclacines by Amanolysis of
Zthylene Oxtde

Pollutant Discherges fron the Manufa
of Sthylenectanire hy Ammonalyaia ©
Behylene Dichloride

Poliucant Discharges frou che Manufacture
of Zehylenedlanine >y dmmusclys
Eehanolaniae

U3. Produstion of Syathette Orgaale
Chemicals Jeing Acination $y Armonalysta

Base

a
BXECUTIVE SROURY

The U.S. Env:

oamental Protectan Agency nas been authorized

der cevencly en:

ad laws to regulete tox

harardous chemicals

sa both products and waste discharges from sanafaeturing operstlons.

esa Laws inotade th

Togle Substances Contevl det af 1975, TL 94-

468; Clean alr Act as amended in 1977, @L, 95-95; Clean WaLez Act oF

250

ty and the devaozee Coasnrvation end Zecovery Act

1976, FL s4-sao.

Regulation of the orgamte chanioal industzy ie extrenely complet

Fevent orgeate corpeunde In comercial proiverton ohds

zo total 289 béliton pounds.

e, che 0.8. Eavdescwoutal Pratae—ioe Agoney said thi

tesves asacetaced with

say ocear tn Fesdscocks, products and anats dischurges

vhant cals

weed 3y che xe 6!

d end £2 typteal toxic discharges and procuet

the unit process are ‘ndlcated, the regulacory
process vould be eieplified.
Ta the “Cetalug of Orgemic Chemical Ladustry Unit Proceaces"”

(0TR-7823), we have ident:

ed 32 major

processes and 19 winse