Lecture Topic 3: Industrial Organic Chemistry
Ref: “Organic Building Blocks of the Chemical Industry”, by H.H. Szmant
“Industrial Organic Chemistry”, by K. Weissermel and H.-J. Arpe
Premise:
Classification of organic chemicals by:
• COST
• PRODUCTION VOLUME
• STARTING MATERIAL
Goal:
Ability to
1. identify bulk, fine and specialty chemicals
2. give examples of primary building blocks and
of C1, C2, C3, C4 and higher acyclic and
cyclic organic building blocks
3. the manufacture of a common chemical from
souces to final products
Cost - Volume
>100
Medicinals and other specialties
Flavours, fragrances
Dyes
10
Specialties
Fine
Chemicals
1
Common plastics
Resins, Elastomers
Pseudo-commodities
Organic intermediates
Commodities
Primary organic
building blocks
0.1
Inorganic heavy
chemicals
0.01
105
106
107
108
109
Demand (lb/y)
1010
1011
1012
US Chemical production 2003-2006 (Import-Export)
Source: C&E News Jan 8 2007
Special position of inorganics: Metal and energy prices rose
Why should we care ? => inflation => Fed hike => filters down to mortgages, credit cards …
Canada produces anything:
•Metals
•Coal
•Gas
•Oil
Why the deficit ?
Many reasons.
•Not enough value addition
(manpower, R&D)
•Economy of scales
(~size of population + others)
The Top Ten
Ammonia
Sulfuric acid
Urea
Polyethylene
Ammoniumnitrate, NH4NO3
Sodiumchlorate NaClO3
Nitric acid
Sodium hydroxide
Chlorine
Benzene
0
500
1000
1500
2000
2500
3000
Take home message: Inorganics Dominate, PE top organic
3500
4000
4500
5000
Cost/Volume: Implications
INDUSTRY CHARACTERISTICS
Product life cycle
# of products
Product volumes
Product prices
Product differentiation
Value added
Capital intensity
R&D focus
BULK CHEMICALS
FINE CHEMICALS
SPECIALTY CHEMICALS
Long
> 100
Moderate
>1,000
Short/moderate
>50,000
>10,000t/y
<10,000t/y
highly variable
<5 $/kg
>5 $/kg
>10 $/kg
none
very low
high
low
high
high
high
process
moderate
process
moderate/low
application
KEY SUCCESS FACTORS



• technical service
–


• links with customer
–
• cost


The History of Industrial Chemistry is linked to Building Blocks
1850-
Plants, Animals
1850+
1920+
Coal Tar (side product of “coal gasification”)
Acetylene (from CaC2, Reppe Chemistry)
1950+
Ethylene (from oil)
1973+
CH4, CO/H2 (syngas)
Future:
CO/H2 from Coal
(exothermic)
CO2 fixation via:
Plants, Animals
CO2 fixation
(endothermic)
(endothermic)
What is a Building Block
A building block is any (organic) chemical that can be
used to synthesize other (organic) chemicals.
There are very few truly primary, large-volume organic
building blocks.
These are all currently obtained from:
• petroleum refining
• natural gas
• coal
• ammonia
• carbon dioxide
• renewable resources
The first Building Block: The Age of Acetylene
Walter Julius Reppe
Reppe Chemistry: Make everything from acetylene.
BASF Ludwigshafen
Examples
R
Co(I)
R C
N
N
Ni(CN)2
PPh3
Ni(CN)2
HC
CH
O
CH2O
HO
CH2 C
C
CH2
OH
• Tricky technology, acetylene explodes under pressure (~ 5 atm).
• Acetylene forms explosive salts with heavy metals (no copper tubes & valves !).
• Largely replaced by ethylene & C1 Chemistry.
•“Inorganic” entry (CaC2) into organic chemistry.
• Still very valuable for fine chemicals
•Could make a comeback with cheap energy.
Building Blocks: Primary, Secondary…
1º BB
2º BBs
Ethylene
ethylene dichloride
ethylene oxide
ethyl benzene
Propylene
propylene oxide
acrylonitrile
isopropyl alcohol
cumene
n-butyl alcohol
3º BB
vinyl chloride
ethylene glycol
vinyl acetate
acetone
Benzene
ethyl benzene
cumene
styrene
phenol
acetone
bisphenol A
Methanol
acetic acid
formaldehyde
MTBE
vinyl acetate
terephthalic acid
Polyester
Toluene
Xylenes
C1-Chemistry
C1 Chemistry in a nutshell:
C1-Chemistry and the Power of Syngas
Advanced C1-Chemistry: Natural Products
C1-Chemistry Database
http://www.aist.go.jp/RIODB/c1db/index.html
Syngas: A Second Look
(+)
From:
Natural Gas (CH4)
Crude Oil
Coal
1976
1982
2000
3%
12 %
16 %
50 % of it SASOL, South Africa
(–)
Energy intensive
(+++)
More than 500 years of coal reserves
(+++)
Anything can be made from Syngas (as long as it contains carbon or hydrogen)
• NH3 (Haber-Bosch process)
• Oxo-products (Hydroformylation
• Gas, Diesel, Lubricants, waxes….. (Fischer-Tropsch process)
(–)
Syngas is dirty (CO, CO2, H2, H2S, COS) but easy to clean
(+)
Very clean Diesel (low sulfur) fuel from syngas (SASOL)
A Brief History of Syngas (H2/CO)
Haber Bosch Process
• Hydrogen for ammonia synthesis obtained as syngas, CO removed
Fischer-Tropsch: Hydrocarbons from Syngas
•“Synthetic fuel” crucial for German war machine
• Leuna plant alone 900,000 t/year, bombed in June 1944
• Technology of the future if oil runs out, center of SASOL company
Hydroformylation: Aldehydes, Alcohols, Amine … from Syngas
• Largest homogeneously catalyzed process
• Origin of modern transition metal catalysis
Organometallics in Industry
Production of Organometallics Verbindungen
-
Silicones
Al-Alkyles
Sn-Alkyles
900.000 t/a
90.000 t/a
35.000 t/a
Products obtained with organometallic catalysts
-
Polypropylene
Polyethylene
„Oxo“-Products
Acetaldehyd
Acetic Acid
17.000.000 t/a
36.000.000 t/a
5.000.000 t/a
2.200.000 t/a
1.000.000 t/a
History of Catalytic Industrial Processes
Very small number of crucial discoveries
Very small number of players
+ Minute amount of “right” catalyst
= Massive production (and $),
= High number of processes & products
The golden path:
1. Understand the first processes
2. Understand which are expanding and why
Petrochemistry & Catalysis: Wacker, Monsanto etc.
The Start of C1 Chemistry: Hydroformylation (Oxo Process)
O. Roelen, Ger. Pat., 949 548, 1938.
•Discovered by Otto Roelen who tried to find out the
cobalt catalyzed FT process produces alcohols
•Largest homogenously catalyzed process in the world
(~ 10 billion Kg of aldehydes)
•1968: Introduction of phosphines to stabilize cat.
•Use of watersoluble Rh-phosphine complexes
•1970: Rh (better n/iso ratio, but EXPENSIVE)
•2004: 75 % use Rh;
•Major process propene to butanol
Hydroformylation (Oxo Process): Instant Recognition
Max Planck is so impressed that he drops his breakfast sandwich permanently (->
sandwich complexes) and Quantum Mechanics temporarily…
… to rush to the scene of the accident and inspect a good bottle of n-butanol.
Good for Otto, because Max controls funding.
Mechanism of the Hydroformylation: From Hieber to Heck
Walter Hieber (right) the pioneer or metal
carbonyl chemistry (left:Behrens, his
lecture assistant).
Heck-Breslow meachnism (1960/61)
Nothing is more practical than a good theory (L. Boltzmann)
Mechanism MUST be comply with rate law
Sounds boring, but…
For ratio of H2/CO = 1:1 reaction rate is
pressure independent due to the opposing
orders of H2 and CO.
Increasing the H2/CO ratio is of limited use
for increasing the overall reaction rate
because HCo(CO)4 is only stable under
certain minimum CO partial pressures at a
given temperature.
Catalysts are Survivors
Stability of HCo(CO)4/Co2(CO)8 species with respect to
precipitation of cobalt metal (cobalt concentration is 0.4
wt. %).
Industrial Catalyst Design (Cheat sheet)
Catalyst: Optimized combination of:
•mechanical properties
•catalytic properties
•physical properties
Three Types of Catalysts:
•Heterogeneous (insoluble)used for high p, high T
•Homogeneous (soluble) used for low T, high/low p
•Enzymes low T, low p
Selectivity increase Heterogen. < homogen. < Enzyme
Heterogeneous Catalyst Design
Mechanical
St abilit y
Catalyst
Design
Act ivit y
Select ivit y
St abilit y
Surface area
porosit y
acidit y
densit y
composit ion
Emile Kuntz (Rhone-Poulenc) has a very good idea
TPPTS
Using TPPTS instead of PPh3 gives a highly water
soluble catalyst:
SO 3 Na
P
Na
O3 S
HRh(CO)[TPPTS Na3]3.
In aqueous solution the catalyst essentially has a 9
charge, making it totally insoluble in all but the most polar
solvents
Na
O3S
Alkenes (C2-C4) are water soluble enough that migration into the aqueous catalyst phase
occurs.
Remigration of the aldehyde product back into the more soluble organic phase allows easy
separation of product from catalyst.
n/iso 18:1 (propene) via water soluble catalyst.
Rates are slower than with conventional Rh/PPh3 catalysts due to lower alkene
concentrations in the water phase and higher amounts of the inactive tris-phosphine Rh
complex.
The process is limited to the shorter chain alkenes that have some appreciable water
solubility.
Alkenes higher than pentene are not soluble enough in water.
Fischer Tropsch Chemistry: 1925 +
Franz Joseph Emil
Fischer
Kaiser-Wilhelm Institut
Mülheim
1913 Director of the newly founded Kaiser-WilhelmInstitute for Coal Research (Mülheim / Ruhr
1925 Discovers formation of hydrocarbons from
Syngas with Hans Tropsch
CO
+ H2
Ni/Co
(CH2)n
1.
2.
3.
Carbide-methylene
Hydroxycarbene
CO insertion
Oil Producing Countries
Mio t
Oil Production/Consumption by Countries
Mio t
Comsumption
Production
US
China
JP
Russia
Germany India
Brasil
Reality Check I: Are We Becoming More Oil Dependent ?
Importance of oil for GDP of G7 countries is dropping
Tons of Crude / Million Euro of GDP
(Germany)
QuickTime™ and a
TIFF (Uncompressed) decompressor
are needed to see this picture.
Coal - Oil - Coal ?
Plus:
500+ years of proven reserves at current consumption levels
Can substitute Oil & Gas:
directly (generation of electricity)
indirectly (Coal gasification - > Syngas -> Chemicals)
Large reserves in countries that do not have oil & gas:
USE
China
Minus:
Can’t be pumpe (no pipeline)
transport expensive unless close to water
High in sulfur
Use of Coal
Electricity From Coal
Energy and the CO2 Footprint
Types of Coal
Geology and Origin of Coal
Coal Players: Peabody, BHP, Teck-Cominco
Major Coal Producers: USA, China
Major Coal Reserves: Australia
CHM 4010
Building Blocks from Coal
Coal
Only 11 % of Benzene Arom at ics
95 % of Condensed Arom at ics
Carbon Black, Graphit e
"Long Term , Coal is t he only plausible alt ernat ive t o
Oil as raw m at erial for t he chem ical indust ry"
CHM 4010
The Coal Tree
S
CCl 4
MeOH, AcOH, Ac2O
Rayon
R2N
S
O
NH3 (6%)
CH4, H2S, CO, H2 (14%)
Cl
CS 2
Cl
SiC
CO H2
calcium
cyanamide CaN C NH
Oxo chemicals
Coal
CaC 2
Coke
acetylene
HC CH
Water gas: H2 (51%), CO (42%), CO2 (6%), N2 (1%)
Metallurgy
Fuel & exports
n
Producer gas: N2 (75%), CO2 (14%), CO (10%), Ar (1%)
Road Tar
Coal Tar
Tar
O
Electrodes
and C fibers
Pitch
Naphtha BTX
Indene
Coumarone
(benzene, toluene, xylenes)
Tar bases
CH 3
Anthracene
Phenanthrene
Light Oil
CH 3
H2C
CH 2
CH 3
N
N
N
Tar acids
OH
Cresols
Creosote
Phenol
Xylenols
CH 3
Acenaphthene
N
H
Carbazole
CH 3
CH 3
C
H2
Fluorene
CHM 4010
Top Three Condensed Aromatics
O
O
600,000 tons
Xylenes
O
100,000 tons
Naphtalene
Phtalic Anhydride
Indene
Thermoplastic resins
Inks
Rubber
O
Coumarone
O
Dyes
H2O2
40,000 tons
O
Anthracen
e
Anthraquinone
Building Block Analysis: Aspirin®
O
OH
O
O
CH 3
OH
OH
O
+
T < 90C
O
Acetyl Salicylic Acid
A.S.A.
90% yield
H3C
liquid phase
50C, 3-4 bar
1. CO2
2. H2SO4
O
OH NaOH
Shawinigan
(Canada)
Cu(acetate) 2
ONa
H3C
+
O2
H
Acetaldehyde
2. H2SO4
Phenol
Kellogg/Monsanto
H2SO4
liquid phase
T & P > STP
+
catalytic
processes
CH 3
Acetic anhydride
Kolbe-Schmitt
reaction
1. O2
Benzene
O
Salicylic Acid
Hock
process
Cumene
O
FOSSIL FUELS:
LPG, Coal, Petroleum, etc.
thermal
cracking
H2C CH 2
Ethylene
Propylene
thermal
cracking
PdCl2 / CuCl2
+
0.5 O2
Wacker-Hoechst
Process
Origin of other Reagents
Cu
Mined as an ore and refined
Pd
Mined and refined (Sudbury, Ontario: “anode slime”)
H2SO4
H2O + 0.5 O2 + SO2
O2
Fractional distillation of liquid air
Acetic acid
Methanol + CO (Monsanto process)
NaOH
Electrolysis of brine (NaCl + H2O) “chloralkali cell”
pyrometallurgical byproduct
Science is naming….
Oil: From Crude Oil to Distillates
Classified by b.p.
Classified by Use
1.
2.
3.
4.
5.
6.
7.
8.
9.
1.
Natural gas:
C1
2.
Propane:
C3
3.
Gasoline:
C7 - C9
4.
Naphta
C6-C11
5.
Kerosene (Paraffin):
C11-C18
5.
Diesel oil
C13-C15
6.
Lubricating Oil
C18-C25
7.
Fuel oil
C20-C27
Gases
Petrol
Naphta
Kerosene
Diesel oil
Lubricating Oil
Fuel oil
Greases & Waxes
Bitumen
Good source of information: http://tonto.eia.doe.gov/dnav/pet/pet_pnp_top.asp
Distillates - A second look
Name
Number of
Carbon Atoms
Boiling Point
(C)
Refinery Gas
3 or 4
below 30
Petrol
7 to 9
100 to 150
Naphtha
6 to 11
70 to 200
Kerosene
(paraffin)
11 to 18
200 to 300
Diesel Oil
11 to 18
200 to 300
Lubricating Oil
18 to 25
300 to 400
Fuel Oil
20 to 27
350 to 450
Greases and
Wax
25 to 30
400 to 500
Bitumen
above 35
above 500
Uses
Bottled Gas
(propane or
butane).
Fuel for car
engin es.
Solvents
and used in
petrol.
Fuel for aircraft
and stoves.
Fuel for road
vehicles
and trains.
Lubricant for
engin es
and machines.
Fuel for ship s
and heating.
Lubricants
and candles.
Road surface
and roofing.
Higher boiling fractions
distilled under vacuum
Fuel: Gasoline vs. Diesel
Petrol and Diesel engines operate differently
•
A high tendency to autoignite is undesirable in a gasoline engine but
desirable in a diesel engine.
•
We need two rating systems
Octane Number
Developed by the chemist Russel Marker
 Isooctane (2,2,4-trimethylpentane) = 100
 n-heptanee =0.
 87-octane equivalent to a mixture of 87 vol-% isooctane and 13 vol-% n-heptane.
 n-Heptane ?
high purity n-heptane originally obtained by distillation of pine resin. Heptane from
crude oil is a mixture of isomers and would not give a precise zero point.
Different Octane numbers, depending on test protocol:
RON = Research Octane Number (used in Europe)
MON = Motor Octane Number
PON = Pump Octane Number = (RON + MON)/2 (US, CAN)
Isooctane is not the most knock-resistant substance available.
Ethanol has RON of 129
Liquified petroleum gass (LPG) > 110.
Octane Boosters
Peak Deficits of high octane fuels:
1940 + WW II (aircrafts)
1960 + Polyesters (Terephatic acid) deplete aromatics
Quick Fix (Kettering & Midgley, GM, Dupont, 1924+)
Tetraethyllead PbEt4 (“Leaded gasoline”) as octane booster (1:1200)
Easily decomposed to its component radicals, scavenges radicals that would start
the
combustion prematurely, thereby delaying ignition.
Production (EtCl + Na-Pb alloy) peaks at 600.000 t/a (insae, MKD)
Phased out (except for Yemen, Afghanistan, North Korea and some African countries)
Highly toxic (“Chernobyl of the ‘20ies)
Incompatible with car catalysts (1975 California) which contain Pt, Pd
New chemistry allows upgrading of fuel at refinery
But:
Still used in aviation fuels !
PbEt4’s early competitor: Ethanol
QuickTime™ and a
TIFF (Uncompressed) decompressor
are needed to see this picture.
This photo, taken in April 1933, shows a Lincoln Nebraska gas station of the Earl Coryell Co. selling "Corn
Alcohol Gasoline." The test marketing of ethanol blends was common in the Midwest at this time, but it did
not succeed due to the market dominance of the major oil companies. Coryell was subsequently among
complainants to the Justice Dept. in the US v. Ethyl antitrust lawsuit of 1936, which Ethyl lost in a Supreme
Court decision in 1940. (Nebraska Historical Society)
QuickTime™ and a
TIFF (Uncompressed) decompressor
are needed to see this picture.
QuickTime™ and a
TIFF (Uncompressed) decompressor
are needed to see this picture.
•colourless to yellow liquid
•Melting point: -136 C
•Boiling point: 84 C at 15 mm Hg, (decomposes near 200 C)
Toxicology
•Highly toxic - may be fatal if inhaled or ingested. Possible mutagen. Experimental carcinogen.
Accumulative poison. Danger of reproductive effects. Note low LD50s below. Irritant.
Toxicity data
RL-RAT LD50 12.3 mg kg-1
C1 Chemistry
C1 building block
Source
Use
CH4 (methane)
Natural gas
energy, H2, CO, CH(4-x)Clx
CO (carbon monoxide)
Coal (as Syngas)
CH3OH, HCOOH, esters,
amides, Oxo acids, etc.
CH3OH (methanol)
CO + 2H2
Cracking of C3H8, C4H10
H2CO, MTBE, CH(4-x)Clx,
CH3COOH
H2CO (formaldehyde)
CH3OH, Cracking of LPG Polymers (UF, PF, POM)
HCOOH (formic acid)
CO + H2O
Fine chemicals
CO2 (carbon dioxide)
Water-gas-shift rxn.
Supercritical fluids (SCFs)
CS2 (carbon disulfide)
S8 + Coke or CH4
Cellulosics, M+SCN–, thiourea
Cl2CO (phosgene)
polyurethanes
CO + Cl2
R-C=N=O
(H2N)2CO (urea)
NH3 + CO2
Fertilizer, Resins (UF)
HCN (hydrogen cyanide)
HCONH2 - H2O
byproduct (acrylonitrile)
Methacrylonitrile, ClCN
The Monsanto Process
First large scale process based on methanol = milestone in the history of
building blocks. Long development due to corrosion problems
O
[Rh, I-]
CH3OH + CO
H3C
60 atm
250 oC
corrosion problems
C
OH
Has largely replaced the two step Wacker process:
O
H2C
CH2 + H2O
[PdCl2]
H3C
O
O2
C
H
H3C
C
OH
Acetic acid is one of the most important secondary C2-building blocks and used
to make vinylacetetate (foils), cellulose acetate…
C2 Chemistry
C2 building block
Source
Use
CH2=CH2 (ethylene)
thermal cracking of natural
gas, refinery gas, crude oil
Feedstock for ~30% of all
petrochemicals!!
Polymers (Polyethylenes etc.)
Alphaolefins (LDPE), PVC
Polystyrene, Polyvinyl acetate
Polyethylene oxide
CH3CH2OH (ethanol)
fermentation,
hydration of ethylene
Gasoline additive (USA),
Ethylene by dehydration
(Brazil, India, Peru, Pakistan),
Solvent, Esters (ethyl chloride,
ethyl acetate)
CH3CH=O (acetaldehyde)
Wacker-Hoechst (ethylene)
Monsanto process (MeOH)
CH3COOH, Acetic anhydride,
Peracetic acid CH3C(=O)OOH,
Aldol condensation products
CH3COOH (acetic acid)&
CH3COOCOCH3 (acetic
anhydride)
Monsanto process (MeOH)
Oxidation of C4-C8 hydrocarbons or acetaldehyde
Vinyl acetate (PVA), Cellulose
acetate, Solvent, Acetate salts,
Chloroacetic acids
HCCH (acetylene)
Coal via CaC2 or
from hydrocarbons
1,4-Butanediol, vinyl acetate
C3 Chemistry
C3 building block
Source
Use
CH3CH2CH3 (propane)
LPG
Propylene, energy
CH3CHCH2 (propene)
Thermal cracking of LPG,
natural and refinery gas
Polypropylene, Acrylonitrile,
Oxo products (butyraldehyde,
butanol, etc.),Propylene oxide
Isopropanol, Cumene,
Oligomers (nonene, dodecene,
heptene)
CH3COCH3
(acetone)
Hock process (coproduct)
Isopropanol (dehydrogen’n)
Wacker-Hoechst (propene)
Methyl methacrylate, Methyl
isobutyl ketone, Bisphenol A,
Aldol condensation products,
Solvent
CH3CH2COOH
(propionic acid)
CH2CH2 (hydroformylation)
Food preservative, Amyl and
Vinyl propionate, Herbicides
C4 Chemistry
C4 building block
Source
Use
C4H10 (butanes)
LPG
1-Butene, Maleic anhydride,
MTBE, thiophene
C4H8 (butenes, isobutene)
Cracking of Cn4
Polymer/alkylate gasoline,
Polymers/copolymers, alcohols
C4H9OH (butyl alcohols)
Propene, acetaldehyde
MEK, Solvent, Fuel additive
CH3(CH2)2CHO
(butyraldehydes)
Propene, acetaldehyde
2-Ethylhexanol, Trimethylolpropane
Maleic anhydride
Oxidation of C4-feedstocks
Benzene (V2O5 catalyst)
Unsaturated polyester resins,
Fumaric acid, Pesticides
HO(CH2)4OH
(1,4-butanediol)
Acetylene
1,3-butadiene
poly(1,4-butylene terphthalate)
THF, H2N(C4H8)NH2
H2C=CH-CH=CH2
(1,3-butadiene)
Cracking of Cn4
Elastomers (i.e., synthetic
rubbers), Chloroprene, THF
O
O
O
C4 Chemistry: Rubber
C5 And higher (acyclic)
Primary Building Blocks
Source(s)
Use
Petroleum: CnHn+2 (n5)
(pentanes, hexanes, heptanes, etc.,
and other n-paraffins)
Fossil fuels
Solvent, Fuel, Lubricant,
Alkylbenzenes, Alcohols,
Chlorinated paraffins,
Lower m.w. alkanes/olefins
Mineral waxes: Ozocerite,
Montan wax
Fossil fuels
(lignite)
Coatings
Fatty Acids: Lard, Tallow, Palm
oil, Corn oil, Castor oil, etc.
Renewable
(animal/plant)
PVC stabilizer, Surfactant,
Glycerine, Methyl laurate,
Fatty amines (antistatic agents)
Tall-Oil Fatty Acids (TOFA)
Renewable
(pulp byproduct)
Fuel in pulping operations,
Dimer/trimer acids for coatings
Terpenes
Renewable
(plant)
Fragrance/flavour “essential”
oils, Turpentine
Fermentation Products:
•Amyl alcohols
• Carboxylic acids,
• Monosodium glutamate (MSG)
Renewable
(plant)
H2S removal from refinery gas,
Food industry, Pharmaceuticals,
Laundry products, etc.
Cyclic Building Block & Aromatics
Building blocks
Source
Use
Benzene
C6H6
Coal, Oil, Petroleum
(thermal/catalytic process)
Ethylbenzene (for styrene),
Cumene (for phenol/acetone),
Cyclohexane, Nitroenzene
Toluene
C6H5CH3
Coal, Oil, Petroleum
(thermal/catalytic process)
Solvent, Benzoic acid, Phenol,
Nitrotoluenes, aminotoluenes
Xylenes
C6H4(CH3)2
Coal, Oil, Petroleum
(thermal/catalytic process)
Phthalic acids and anhydrides
(plasticizers, synthetic fibers)
Cumene C6H5CH(CH3)2
Benzene
Hock process (phenol/acetone)
Phenol C6H5OH
Cumene (Hock process)
Benzene, Toluene,
Phenol resins, Bisphenol A,
ε-Caprolactam
Cyclopentadiene
C5 cracking fractions,
Coal tar
Polymers (for resins, contact
adhesives, printing ink resin)
Cyclohexane
Crude gasoline,
Benzene (hydrogenation)
Cyclohexanone (feedstock for
nylon precursors)
• Structural adhesives
• Structural sealants
Cl2
Allyl chloride
Epichlorohydrin
• Primer paints
Epoxy resin
• Electrical insulation
Propylene
• Dashboards
• Electrical insulation
• Vinyl tops
• Floor mats
• Upholstery
• Modular window
frame units
BTX
• Fiber reinforced plastic
composites
Bisphenol A or
Brominated Bisphenol A
Ethylene
Vinyl
Vinyl chloride
monomer
Cl2
• Body side moldings
• Molded armrests
• Exterior & interior trim
• Tires
• Rubber hoses
• Foam for seats
• Caulks & sealants
• Bumpers & fenders
CO2
Polyurethanes
Polyisocyanates
Phosgene
Cl2