The Global Petrochemical Industry:
Understanding the Complex Interactions Between Technology, Economics and Markets
Online Training
Manuel Asali
Vice President
Copyright © by Nexant Inc. 2019
All rights reserved
Propylene and derivatives
Section 3
Cumene, phenol and acetone
Section 3 Module 6
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The cumene value chain
BENZENE
AND
PROPYLENE
CUMENE
PHENOL
ACETONE
CYCLOHEXANONE(1)
CAPROLACTAM
NYLON 6
SOLVENTS
METHYL METHACRYLATE
BISPHENOL A
PHENOLIC RESINS
EPOXY RESINS
POLYCARBONATES
(1) Most cyclohexanone is made from benzene
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Cumene and phenol top producers, 2018
The top 10 represents 52 percent of cumene and 60 percent of phenol
capacity
0
200
400
600
800
1000
1200
1400
1600
1800
2000IN
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Tho
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Cumene Phenol
Source: Nexant
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Cross-linked phenol–formaldehyde resin (bakelite)
GPO 300 Series – Bakelite Black
Leo Baekeland
Phenol-Formaldehyde Resin
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Bakelite (phenol-formaldehyde resin)
“The material for a thousand uses”
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Bisphenol A formation
+ 3 3 HO +
OH
2 CH -C-CH C OH HO C
OH
CH
CH CH
CH
3
3 3
3
O
PHENOL ACETONE p,p' - BISPHENOL A o,p' - BISPHENOL A
The mixture is useful for most epoxy resin grades. The p, p' - isomer is
necessary for polycarbonates and the lesser volume engineering resins such
as polysulfones, polyarylates, and poly(ether imides).
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BPA under pressure for toxicity reasons
Feb 27, 2007 11:37 am US/Pacific
Report: Plastic Baby Bottles Leach Toxic Chemical
Chemical Used To Make Plastic Released Into Liquid
Polycarbonate Baby Bottles
Critics claim BPA mimics the female hormone estrogen, is linked to:
birth defects in boys, heart disease in adults, lower sperm counts, diabetes,
hyperactivity, miscarriage and breast cancer in animals
Many Industry sponsored studies dispute these findings.
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BPA free photo
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Epoxy resins - a value chain
PROPYLENE
ALLYL
CHLORIDE EPICHLOROHYDRIN
CUMENE
BENZENE
PHENOL
ACETONE
BISPHENOL A
EPOXY
RESINS
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Epoxy – two-part formulation
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Global epoxy resin demand, 2018
Coatings 54%
Electrical/ Electronics
18%
Composites 10%
Construction 8%
Adhesives/ Sealants
7%
Others 3%
Source: Nexant
Asia Pacific 62%
Western Europe
18%
North America
15%
ROW 5%
Global Demand = 2.6 Million Tons
Demand by End-Use Demand by Region
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Epoxy coatings
Powder coating UV inks Marine coatings
Coil and can coatings Automotive coatings Seamless Flooring
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Epoxy resin applications
Composites Electrical Encapsulation Electronic Laminations
Civil engineering Carbon Fiber / Epoxy Composite Adhesives
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New Boeing 787 constructed of 50% carbon/epoxy composite
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The Big 3 have been evolving
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Polycarbonate formation
n NaO C
CH3
CH3
ONa + nCOCI2
Bisphenol A
(Water)
Phosgene
O C
CH3
CH3
O C
O
+ 2n NaCl
Polycarbonate
Phase Transfer
Catalyst
n
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Polycarbonate properties
Advantages Disadvantages
Impact resistance Poor solvent resistance
Ductility Poor abrasion resistance
Clarity Limited UV resistance
Dimensional stability Notch sensitivity
Creep resistance Limited hydrolytic stability
Rigidity
High temperature resistance
Electrical properties
Inherent fire resistance
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Polycarbonate innovation timeline
1953: Dr. Daniel Fox invents PC 1962: Astronaut helmet 1968: PC sheets
1978: Auto light lenses 1980: Auto instrument panels 1984: Compact discs (CDs)
1990: eye lenses 1994: Flip phones 1996: DVDs 1998: Consumer electronics
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Polycarbonate end-use products
SABIC website Kartell chair
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The polymer industry evolves with music
Phenolic resins PVC (Vinyl) PS case, PET tape
1980s: CD (Polycarbonate) From 2001… Multiple polymers (PMMA, PC/ABS, etc.)
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Global polycarbonate producers 2018
0
200
400
600
800
1000
1200
1400
1600
Tho
usan
d to
ns
Top 10 Represents 85 percent of Global Capacity
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Electrical & Electronics
28%
Construction 12% Automotive
15%
Optical media 11%
Others 27%
Global polycarbonate demand, 2018
AP 59%
NA 14%
WE 16%
CE/EE 7%
ME 2%
SA 2%
Africa 0.5%
Global Demand = 4.4 Million Tons
Demand by End-Use Demand by Region
AP: Asia Pacific
WE: Western Europe
ME: Middle East
NA: North America
SA: South America
CE/EE: Central/Eastern Europe
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Many routes to MMA
H3CC
CH3
O
H2CC
COCH3
CH3
O
H C N, C H3OH,
H2SO4
-NH4H SO4
H3C
C CH2
H3CO2, C H3OH
H3C C
CH3
CH3
OH
O2, CH3OH
H3C
C CH2
H3C
N H3, O2, C H3OH,
H2SO4-N H4H SO4
H3CC
CH3
O
C O, C H3OH
H2C CH2
CO/H2, CH2CO,
O2, CH3OH
HC CCH3
C O, CH3OH
HC
CH3
CH3H3C
O2
C H3OH
Conventional
Route
Japanese
Route
Japanese
Route
Japanese
Route
BASF, Lucite
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One of the first uses for PMMA (PLEXIGLAS)
In 1943 alone, the U.S. produced 86 000 warplanes and
R&H sold 22 million dollars of Plexiglas
Otto Rohm Otto Haas
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PMMA in the Battle of Britain!
MESSERSCHMITT
(Plexiglas)
SPITFIRE
(Perspex)
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Polymethylmethacrylate (PMMA)
Automotive Flat-screen TVs
Medical
Signs
Glazing
Lighting Altuglas
website
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