Download - A Green Chemistry Module
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A Green Chemistry Module
Petretec – Dupont’s Technology for Polyester Regeneration
Presidential Green Chemistry Challenge Award
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World Proven Reserves of Crude Oil
63.7
89.5
20.6
74.9
65.4
44.0675.7
thousand million barrels
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World Proven Crude Oil Reserves
as percent of 1296 thousand million barrel total
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Composition of Crude Oil
CRUDE OIL
HYDROCARBONS NON-HYDROCARBONS
ALIPHATICS AROMATICS NAPHTHENES SULFURS NITROGENS OXYGENS METALLICS
25% 17% 50% <8% <1% <3% <100PPM
C1 - C60 (C6H5)n CYCLOALKANESSH
S
NH
O
COOH
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Crude Oil Classification
PETROLEUMSaturates
Aromatics
Asphalticsn-alkanes C5 - C44
branched alkanescycloalkanes (napthenes) single ring
condensed ring
nitrogenoxygensulfur
containing compounds
API Gravity = 35o
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The Uses of Crude Oil
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The Xylenes
Boiling Point 144oC 139.3oC 137-138oC Melting Point -25oC -47.4oC 13-14oC
ortho meta para
CH3
CH3
CH3
CH3
CH3
CH3
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CRUDE
DESALTING
REFINING
REFORMING
BLENDING
Distillation to separate by boiling point ranges
Water washing to remove impurities
Conversion reactions to alter molecular structures
Mixing to obtain maximum commercial characteristics
Petroleum delivered from well field
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Petroleum Refining
GAS
LIGHT NAPHTHA
HEAVY NAPHTHA
KEROSENE
ATM. GAS OIL
RESIDUUM
CRUDE DESALTER FURNACE
C1-C4
bp < 50 oF
C5 - C?
bp 50-200oF
C? - C12
bp 200-400oF
C12 - C16
bp 400-500oF
C15 - C18
bp 500-650oC
> C20
bp >650oF
TOWER
Distillation – separation by boiling point
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Petroleum ReformingGAS
LIGHT NAPHTHA
HEAVY NAPHTHA
KEROSENE
ATM. GAS OIL
RESIDUUM
TOWER
FUEL GAS
TREATER
HYDROTREATER
HYDROTREATER
HYDROTREATER
REFORMER AROMATIC EXTRACTION
CATALYTICCRACKER
JET FUELS/KEROSENE
DIESEL & FUEL OILS
GASOLINE
AROMATICS
VacuumDistillation
VACUUM GAS OIL
LUBRICATING OIL
COKER COKE
ASPHALT
CATALYTICCRACKER
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Conversion Reactions
gasoline gasoline additive recycle
C7H15.C15H30.C7H15 C7H16 + C7H14 + C15H30CRACK
COMBINE
REARRANGE
THERMAL
CATALYTIC
ALKYLATION
POLYMERIZATION
REFORMIING
ISOMERIZATION
CH3CH2CH3 CH2 CH CH2 CH3CH3CH2CH2 CH2CH2CH2CH3
C H3C
CH3
CH2C H3C
CH3
CH2C H3C
CH3
CH3
C CH2
CH3
H
CH2C CHCH3
CH3CH3
CH3
H3CC
82% 18%
Dehydrogenation
Dehydroisomerization
Isomerization
Dehydrocyclization
Hydrocracking
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Catalytic Reforming – Conversion ReactionsDehydrogenation of cycloalkanes to aromatics
Dehydroisomerization of cyclopentanes to aromatics
Isomerization of alkanes
Dehdrocyclization of alkanes
Hydrocracking of alkanes
CH3 CH3
3H2
CH3
3H2
CH3CH2CH2CH2CH3 CHH3C
CH3
CH2 CH3
CH3CH2CH2CH2CH2CH2CH3
CH3
4 H2
CH3CH2CH2CH2CH2CH2CH3 CH3CH2CH3 CH3CH2CH2CH3
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Preparation of PET monomers
CH2H2CO2
Ag
OCHH3C
OH
CH
OH
CH3
C H 3
C H 3
[ O 2 ]
C
C
O
O O H
O H
T A
C H 3 OH C H 3 OH / C o O 2
C
C
O
O
O C H 3
O C H 3
D MT
Formation of ethylene glycol
Formation of TA and DMT
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PET Polymerization Reactions
C
O
CH3O C
O
OCH3 2n CH2HO CH2 OH
low Temp - 2n CH3OH
C
O
C
O
CH2HO CH2 O CH2O CH2 OH
C
O
C
O
CH2O CH2 O
n
n
CO
HOC
O
OHCH2HO CH2 OH
n
n CH2O CH2 Ohigh Temp
-H2OC
O
C
O
n
Step Growth Polymerization - Condensation
Ester Interchange - Transesterification
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The Dupont
Petretec
Process
For
Polyester
Regeneration
SCRAP PET
Contaminated PET PET for Recycling
Landfill/Incinerate Mechanical Recycling PET / DMT
solution
DMTTemp > 220oC
METHANOLYSIS REACTORCH3OH, 260-300
oC, 340-650kPa
DMT + Ethylene Glycol excess CH3OH
Methanol removal column
CH3OH DMT / Ethylene Glycol azeotrope
MPTdistillation
MPT / Ethylene Glycol
Ethylene Glycol / MPT
DMT
Pure DMTdistillation
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Petretec Polyester Regeneration
C
O
C
O
CH2O CH2 O n
n
CH2HO CH2 OHCO
COCH3OH
n
CH3O OCH3
Methanolysis Reactor
260-300oC 340-650 kPa