Organic chemistry principles and industrial practice:
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|---|---|
| Format: | Buch |
| Sprache: | English |
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Weinheim
Wiley-VCH
2003
|
| Schlagworte: | |
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| Beschreibung: | XX, 321 S. graph. Darst. |
| ISBN: | 3527302891 |
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| 100 | 1 | |a Green, Mark M. |d 1956- |e Verfasser |0 (DE-588)124887813 |4 aut | |
| 245 | 1 | 0 | |a Organic chemistry principles and industrial practice |c M. M. Green ; H. A. Wittcoff |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2003 | |
| 300 | |a XX, 321 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Technische organische Chemie - Lehrbuch | |
| 650 | 4 | |a Chemical engineering | |
| 650 | 4 | |a Chemistry, Organic | |
| 650 | 0 | 7 | |a Technische organische Chemie |0 (DE-588)4184575-4 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4123623-3 |a Lehrbuch |2 gnd-content | |
| 689 | 0 | 0 | |a Technische organische Chemie |0 (DE-588)4184575-4 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Wittcoff, Harold A. |e Verfasser |4 aut | |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009937039&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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Datensatz im Suchindex
| _version_ | 1808135556013490176 |
|---|---|
| adam_text |
VII
CONTENTS
PREFACE
XV
WHAT
THE
EXPERTS
SAY
ABOUT
THIS
BOOK
XIX
1
HOW
PETROLEUM
IS
CONVERTED
INTO
USEFUL
MATERIALS:
CARBOCATIONS
AND
FREE
RADICALS
ARE
THE
KEYS
1
1.1
THE
CONFLICTING
USES
FOR
PETROLEUM:
THE
CHEMICAL
INDUSTRY
AND
THE
INTERNAL
COMBUSTION
ENGINE
1
1.2
HOW
DO
WE
ACHIEVE
THESE
TWO
OBJECTIVES?
BY
USING
TWO
DIFFERENT
KINDS
OF
CRACKING:
ONE
DEPENDS
ON
FREE
RADICALS
AND
THE
OTHER
ON
CARBOCATIONS
2
1.3
WHAT
IS
IN
PETROLEUM?
3
1.4
THE
HISTORICAL
DEVELOPMENT
OF
STEAM
CRACKING
4
1.5
WHAT
WAS
AVAILABLE
BEFORE
THERMAL
AND
STEAM
CRACKING?
6
1.6
ACETYLENE
WAS
WIDELY
AVAILABLE
BEFORE
STEAM
CRACKING
AND
EXCEPTIONALLY
USEFUL
BUT
EVERYONE
WANTED
TO
REPLACE
THIS
DANGEROUS
INDUSTRIAL
INTERMEDIATE.
HAPPILY,
DOUBLE
BONDS
REPLACED
TRIPLE
BONDS
6
1.7
PETROLEUM
YIELDS
ETHYLENE
AND
LAYS
THE
GROUNDWORK
FOR
A
NEW
KIND
OF
CHEMICAL
INDUSTRY
8
1.8
BUT
WHAT
ABOUT
THAT
THIRSTY
INTERNAL
COMBUSTION
ENGINE?
THE
DEVELOPMENT
OF
CATALYTIC
CRACKING
8
1.9
DISCOVERY
OF
THE
PROPER
CATALYST
FOR
CATALYTIC
CRACKING:
FROM
NATURAL
SYNTHETIC
ZEOLITES
10
1.10
LETS
COMPARE
THE
MECHANISMS
OF
STEAM
AND
CATALYTIC
CRACKING:
FREE
RADICALS
VERSUS
CARBOCATIONS
12
1.11
HOW
ARE
FREE
RADICALS
FORMED
IN
STEAM
CRACKERS,
AND
WHAT
DO
THEY
DO?
12
1.12
NOW
LETS
LOOK
AT
CATALYTIC
CRACKING
AND
THE
ESSENTIAL
ROLE
OF
CARBOCATIONS
AND
THEIR
ABILITY
TO
REARRANGE
THE
STRUCTURE
OF
ORGANIC
MOLECULES
15
1.13
WHAFS
GOING
ON
INSIDE
THOSE
ZEOLITE
PORES?
16
1.14
WHY
DO
STEAM
CRACKING
AND
CATALYTIC
CRACKING
PRODUCE
SUCH
DIFFERENT
RESULTS.
OR,
IN
OTHER
WORDS,
WHY
DO
CARBOCATIONS
AND
FREE
RADICALS
BEHAVE
SO
DIFFERENTLY?
19
1.15
SUMMARY
20
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
1
21
VIII
I
CONTENTS
2
POLYETHYLENE,
POLYPROPYLENE
AND
THE
PRINCIPLES
OF
STEREOCHEMISTRY
23
2.1
THE
THERMODYNAMICS
OF
ADDITION
POLYMERIZATION:
THE
COMPETITION
BETWEEN
ENTHALPY
AND
ENTROPY
23
2.2
POLYETHYLENE
IS
FORMED
VIA
A
FREE
RADICAL
POLYMERIZATION
THAT
INVOLVES
THE
CLASSIC
STEPS
OF
ALL
CHAIN
REACTIONS:
INITIATION,
PROPAGATION,
AND
TERMINATION
24
2.3
ATTEMPTED
FREE
RADICAL
POLYMERIZATION
OF
PROPYLENE.
IT
FAILS
BECAUSE
OF
RESONANCE
STABILIZATION
OF
ALLYLIC
RADICALS
27
2.4
SO
HOW
IS
POLYPROPYLENE
MADE?
ORGANOMETALLIC
CHEMISTRY
CAN
DO
WHAT
FREE
RADICAL
CHEMISTRY
CANNOT.
AND
THE
BIG
SURPRISE
IS
THE
ROLE
OF
STEREOCHEMISTRY
AND
SPECIFICALLY
CHIRALITY.
THIS
IS
SOMETHING
NO
ONE
SUSPECTED
29
2.5
THERE
ARE
MORE
KINDS
OF
POLYETHYLENE
THAN
THE
ONE
PRODUCED
BY
THE
FREE
RADICAL
CHAIN
MECHANISM
29
2.6
WHAT
HAVE
WE
LEARNED
FROM
THE
ORGANOMETALLIC
METHOD
FOR
POLYMERIZING
ETHYLENE
THAT
LEADS
TO
THE
POSSIBILITY
OF
POLYMERIZING
PROPYLENE?
32
2.7
DO
THE
METHYL
GROUPS
ON
EVERY
THIRD
CARBON
ON
EACH
INDIVIDUAL
POLYPROPYLENE
CHAIN
ALL
HAVE
TO
BE
ON
THE
SAME
SIDE
OF
THE
CHAIN?
34
2.8
WHAT
DO
THE
OPPOSITE
"
FACES
"
OF
PROPYLENE
HAVE
TO
DO
WITH
THE
FORMATION
OF
ISOTACTIC
POLYPROPYLENE
BY
THE
ZIEGLER-NATTA
CATALYST?
35
2.9
FROM
THE
ZIEGLER-NATTA
CATALYST
TO
SINGLE-SITE
CATALYSTS:
CREATING
A
CATALYST
WITH
A
PRECISELY
KNOWN
STRUCTURE
THAT
CAN
POLYMERIZE
PROPYLENE
TO
AN
ISOTACTIC
POLYPROPYLENE
36
2.10
HOW
DOES
THIS
SMALL
MOLECULE
ANALOG
OF
THE
ZIEGLER-NATTA
CATALYST
POLYMERIZE
POPYLENE?
38
2.11
AN
INTERESTING
STORY
CONCERNING
INDUSTRIAL
CONFLICT
40
2.12
SUMMARY
41
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
2
42
3
THE
CENTRAL
ROLE
OF
ELECTROPHILIC
AROMATIC
SUBSTITUTION
45
3.1
MATERIALS
DERIVED
FROM
ETHYLENE,
PROPYLENE
AND
BENZENE
ARE
ALL
AROUND
US
45
3.2
THE
CARBON
ATOMS
IN
ETHYLENE,
PROPYLENE
AND
BENZENE
FIND
THEIR
WAY
INTO
POLYSTYRENE,
POLYCARBONATE,
AND
EPOXY
RESIN
46
3.3
INDUSTRIAL
SYNTHESIS
OF
THE
BUILDING
BLOCKS
OF
POLYSTYRENE,
POLYCARBONATE,
AND
EPOXY
RESIN
47
3.4
HOW
ISOPROPYLBENZENE
IS
INDUSTRIALLY
PRODUCED
AND
THE
STRUGGLE
TO
REDUCE
THE
DI
AND
TRIISOPROPYLBENZENE
BYPRODUCTS
49
3.5
HOW
ETHYLBENZENE
IS
PRODUCED
INDUSTRIALLY
52
3.6
ZEOLITES
AND
ETHYLBENZENE
52
3.7
HOW
DOES
THE
ZEOLITE
CATALYST
REPRESS
THE
FORMATION
OF
DI
AND
TRIETHYLBENZENE?
54
3.8
SO
WHY
ARE
ZEOLITES
NOT
USED
FOR
THE
FORMATION
OF
CUMENE?
54
3.9
WHAT
ROLE
DOES
CUMENE
PLAY
IN
THE
PRODUCTION
OF
EPOXY
RESIN
AND
POLYCARBONATE?
56
CONTENTS
I
IX
3.10
HOW
PHENOL
AND
ACETONE
REACT
TOGETHER
TO
FORM
AN
ISOMERIC
MIXTURE
OF
THE
INTERMEDIATE
HOC
6
H
4
C(CH
3
)2OH,
WHICH
THEN
GOES
ON
TO
FORM
ISOMERS
OF
BISPHENOL
A
56
3.11
WE
CONTINUE
OUR
BACKWARD
PATH.
HOW
ARE
PHENOL
AND
ACETONE
FORMED
FROM
CUMENE?
59
3.12
A
REMARKABLE
REARRANGEMENT
60
3.13
SUMMARY
62
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
3
64
4
FROM
NUCLEOPHILIC
CHEMISTRY
TO
CROSSLINKING,
WITH
A
SIDE
TRIP
TO
GLYCEROL,
IN
THE
SYNTHESIS
OF
COMMERCIALLY
IMPORTANT
PLASTICS
67
4.1
THE
STRUCTURE
AND
USE
OF
EPOXY
RESINS
67
4.2
EPOXY
COATINGS
AND
THEIR
CURING
(CROSSLINKING)
AND
POT
LIFE
68
4.3
THE
MOLECULAR
SOURCE
OF
THE
TOUGHNESS
OF
EPOXY
RESIN
71
4.4
WITH
EPICHLOROHYDRIN
AND
BISPHENOL
A
WE
ARE
ONLY
ONE
STEP,
A
NUCLEOPHILIC
STEP,
FROM
EPOXY
RESIN.
IT
ALL
DEPENDS
ON
THE
REACTIVITY
OF
THE
EPOXIDE
RING
71
4.5
JUST
AS
FOR
FORMATION
OF
EPOXY
RESIN,
CURING
OF
EPOXY
RESIN
ALSO
INVOLVES
NUCLEOPHILIC
CHEMISTRY
AND
THE
REACTIVITY
OF
THE
EPOXIDE
RING
74
4.6
HOW
EPICHLOROHYDRIN
IS
SYNTHESIZED
FROM
ALLYL
CHLORIDE
BY
A
CLASSIC
DOUBLE
BOND
ADDITION
REACTION
FOLLOWED
BY
FORMATION
OF
AN
EPOXIDE
76
4.7
HOW
IS
ALLYL
CHLORIDE
PRODUCED
INDUSTRIALLY
FROM
PROPYLENE?
77
4.8
A
LESS
TEMPERATURE-DEPENDENT
WAY
TO
MAKE
EPICHLOROHYDRIN
79
4.9
A
FINAL
NOTE
ABOUT
EPOXY
RESINS
80
4.10
WHAT
DID
THE
ORIGINAL
SHELL
METHOD
FOR
PRODUCING
EPICHLOROHYDRIN
HAVE
TO
DO
WITH
GLYCEROL?
THE
ANSWER
IS
ALKYD
RESINS
AND
THIS
WILL
TEACH
US
MORE
ABOUT
CROSSLINKING
AND
ALSO
INTRODUCE
NUCLEOPHILIC
ACYL
CHEMISTRY
80
4.11
THE
EARLIEST
PRODUCTION
OF
GLYCEROL
AROSE
FROM
PRODUCTION
OF
SOAP
86
4.12
WHAT
COMMERCIAL
USES
EXIST
FOR
GLYCEROL?
87
4.13
THE
ROLE
OF
GLYCEROL
IN
DYNAMITE,
AND
THE
NOBEL
PRIZE
88
4.14
GLYCEROL
PLAYS
A
ROLE
IN
THE
PRODUCTION
OF
POLYURETHANES:
NUCLEOPHILIC
CHEMISTRY
AND
CROSSLINKING
89
4.15
POLYURETHANES
ARE
A
PRODUCT
OF
THE
CHEMICAL
REACTIVITY
OF
ISOCYANATES
90
4.16
A
ROUTE
TO
CHEMICALLY
CROSSLINKED
POLYURETHANES
92
4.17
POLYETHER
POLYOLS
ARE
WIDELY
USED
FOR
FORMING
CROSSLINKED
POLYURETHANES.
THERE
ARE
MANY
VARIATIONS
ON
THIS
THEME
93
4.18
WHAT
ABOUT
THE
FOAMED
STRUCTURE
OF
THE
POLYURETHANE?
ADDITION
OF
A
SMALL
AMOUNT
OF
WATER
IS
A
COMMON
ANSWER
94
4.19
LETS
RETURN
AGAIN
TO
BISPHENOL
A
AND
LEARN
ABOUT
AN
ENTIRELY
DIFFERENT
KIND
OF
PLASTIC,
POLYCARBONATE,
WHICH
IS
VERY
DIFFERENT
FROM
EPOXY,
ALKYD
RESINS
AND
POLYURETHANES
95
4.20
HOW
POLYCARBONATES
ARE
SYNTHESIZED
AND
THE
UNWELCOME
ROLE
OF
PHOSGENE
96
4.21
IS
THERE
A
FUTURE
IN
THE
CHEMICAL
INDUSTRY
FOR
A
CHEMICAL
AS
DANGEROUS
AS
PHOSGENE?
99
4.22
A
FEW
REMARKS
ABOUT
THE
DOUBLE
MEANING
OF
CHLORIDE
AS
A
LEAVING
GROUP
99
X
I
CONTENTS
4.23
SUMMARY
101
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
4
103
5
5.1
5.2
5.3
THE
NYLON
STORY
107
WHAT
WAS
THE
WORLD
OF
POLYMERS
LIKE
WHEN
CAROTHERS
ENTERED
THE
PICTURE?
107
WHAT
DID
CAROTHERS
DO
AT
DUPONT?
109
CAROTHERS
'
WORK
AT
DUPONT
HAD
ENORMOUS
CONSEQUENCES
FOR
BOTH
DUPONT
AND
THE
CHEMICAL
INDUSTRY?
ILL
5.4
THE
SIMILARITIES
AND
DISTINCTIONS
OF
THE
VARIOUS
POLYAMIDES
THAT
MAKE
UP
THE
FAMILY
OF
NYLONS
112
5.5
THE
INDUSTRIAL
ROUTE
TO
ADIPIC
ACID
AND
HEXAMETHYLENE
DIAMINE:
THE
PRECURSORS
OF
NYLON
6,6.
BENZENE
IS
THE
SOURCE
116
5.6
HEXAMETHYLENE
DIAMINE
FROM
1,3-BUTADIENE.
IMPROVING
A
ROUTE
TO
A
NEW
KIND
OF
RUBBER
LED
TO
A
BETTER
WAY
TO
SYNTHESIZE
HEXAMETHYLENE
DIAMINE:
INDUSTRY
AND
THE
PRINCIPLE
OF
THERMODYNAMIC
VERSUS
KINETIC
CONTROL
OF
REACTION
PRODUCTS
119
5.7
5.8
5.9
5.10
5.11
THE
ROLE
OF
ACRYLONITRILE
IN
THE
PRODUCTION
OF
NYLONS
122
FROM
THE
DICARBOXYLIC
ACID
AND
THE
DIAMINE
TO
NYLON?
125
NYLONS
MADE
FROM
A
SINGLE
MONOMER
NYLON
6
127
ANOTHER
NYLON
MADE
FROM
A
SINGLE
MONOMER
NYLON
11
129
SUMMARY
132
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
5
134
6
6.1
COMPETITION
FOR
THE
BEST
INDUSTRIAL
SYNTHESIS
OF
METHYL
METHACRYLATE
137
ECONOMIC
AND
ENVIRONMENTAL
FACTORS
ARE
DRIVIING
FORCES
FOR
INDUSTRIAL
INNOVATION
137
6.2
6.3
PLEXIGLASYY
137
THE
CLASSICAL
ROUTE
TO
METHYL
METHACRYLATE
INVOLVES
THE
ESSENTIAL
ROLE
OF
CYANOHYDRINS,
WHICH
CAN
BE
EASILY
CONVERTED
TO
UNSATURATED
CARBOXYLIC
ACIDS
139
6.4
6.5
PROBLEMS
IN
THE
CLASSICAL
APPROACH
TO
SYNTHESIS
OF
METHYL
METHACRYLATE
142
WHAT
NEW
POSSIBILITIES
EXIST
FOR
REPLACING
THE
OLD
PROCESS?
CAN
THE
AMMONIUM
BISULFATE
DISPOSAL
PROBLEM
BE
SOLVED?
143
6.6
THE
MITSUBISHI
GAS
CHEMICAL
COMPANY
APPROACH
TO
IMPROVING
THE
SYNTHESIS
OF
METHYL
METHACRYLATE
144
6.7
THE
DOUBLE
BOND
STILL
HAS
TO
BE
INTRODUCED
TO
FORM
THE
FINAL
METHYL
METHACRYLATE
PRODUCT
146
6.8
6.9
6.10
CAN
THINGS
STILL
BE
IMPROVED
FURTHER?
146
FROM
ISOBUTENE
TO
METHYL
METHACRYLATE:
MITSUBISHI
RAYON
VERSUS
ASAHI
147
HOW
ENVIRONMENTAL
REASONS
STOPPED
THE
USE
OF
TETRAETHYLLEAD
AS
AN
OCTANE
IMPROVER
IN
GASOLINE
LEADING
TO
ITS
REPLACEMENT
WITH
METHYL
TERTIARY
BUTYL
ETHER
(MTBE).
BUT
MTBE
IS
SYNTHESIZED
FROM
ISOBUTENE,
WHICH
COULD
HAVE
BLOCKED
THE
SUPPLY
OF
ISOBUTENE
FOR
PRODUCTION
OF
METHYL
METHACRYLATE.
BUT
ENVIRONMENTAL
CONCERNS
ABOUT
MTBE
HAVE
CAUSED
IT
TO
LOSE
FAVOR
AS
AN
OCTANE
IMPROVER
IN
GASOLINE
THEREFORE
RELEASING
ISOBUTENE
FOR
PRODUCTION
CONTENTS
I
XI
OF
METHYL
METHACRYLATE.
A
STORY
OF
THE
UPS
AND
DOWNS
OF
THE
CHEMICAL
INDUSTRY
-
WHAT
A
RIDE!
148
6.11
A
COMPETITIVE
PROCESS
FOR
THE
SYNTHESIS
OF
METHYL
METHACRYLATE
BASED
ON
ETHYLENE
150
6.12
A
COMPETITIVE
PROCESS
FOR
SYNTHESIS
OF
METHYL
METHACRYLATE
BASED
ON
PROPYLENE
151
6.13
A
POSSIBLE
COMMERCIAL
SYNTHESIS
OF
METHYL
METHACRYLATE
STARTING
FROM
METHYL
ACETYLENE
152
6.14
SUMMARY
153
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
6
155
7
7.1
7.2
7.3
7.4
NATURAL
RUBBER
AND
OTHER
ELASTOMERS
157
INTRODUCTION
TO
RUBBER
157
WHY
ARE
SOME
MATERIALS
RUBBERY?
158
THE
CONFORMATIONAL
BASIS
OF
ELASTICITY
158
HOW
DOES
THE
STRUCTURE
OF
NATURAL
RUBBER
FIT
INTO
THE
THEORETICAL
PICTURE
OF
ELASTICITY
DRAWN
ABOVE?
160
7.5
7.6
LETS
TAKE
A
SHORT
DIVERSION
FROM
ELASTOMERS
162
ELASTOMERS
REQUIRE
ESSENTIALLY
COMPLETE
RECOVERABILITY
FROM
THE
STRETCHED
STATE.
THE
STORY
OF
VULCANIZATION
AND
HOW
SULFUR
SUPPLIES
THIS
CHARACTERISTIC
TO
HEVEA
RUBBER
163
7.7
7.8
WHAT
HAPPENS
WHEN
SULFUR
AND
NATURAL
RUBBER
ARE
MIXED
AND
HEATED?
164
HYPALON:
AN
ELASTOMER
THAT
CAN
BE
CROSSLINKED
WITHOUT
THE
PRESENCE
OF
DOUBLE
BONDS
167
7.9
MANY
SYNTHETIC
ELASTOMERS
ARE
PRODUCED
BY
THE
CHEMICAL
INDUSTRY.
IN
EVERY
CASE
THE
PHYSICAL
PRINCIPLES
ARE
IDENTICAL
TO
THOSE
AT
WORK
IN
NATURAL
RUBBER
AND
THE
ESSENTIAL
CHARACTERISTIC
OF
AN
ELASTOMER
MUST
BE
PRESENT,
THAT
IS,
A
CROSSLINKED
FLEXIBLE
POLYMER
CHAIN
170
7.10
WHAT
KINDS
OF
POLYMER
PROPERTIES
WILL
PRECLUDE
ELASTOMERIC
BEHAVIOR?
WHAT
KINDS
OF
POLYMERS
COULD
BE
CALLED
ANTI-ELASTIC?
177
7.11
PHYSICAL
INTERACTIONS
AMONG
POLYMER
CHAINS
CAN
BE
USED
TO
FORM
ELASTOMERS
WITH
UNIQUE
PROPERTIES.
HOW
THE
POLYMERIC
GLASSY
STATE
CAN
ACT
AS
A
PHYSICAL
CROSSLIN
177
7.12
VARIATIONS
ON
THE
BLOCK
THEME
PRODUCE
THERMOPLASTIC
POLYURETHANE
ELASTOMERS
INCLUDING
SPANDEX
(LYCRAYY),
THE
ELASTIC
FIBER.
HERE,
THE
CROSSLINKS
INVOLVE
A
KIND
OF
PHYSICAL
INTERACTION,
WHICH
IS
DIFFERENT
FROM
GLASS
FORMATION
183
7.13
7.14
7.15
SPANDEX:
A
POSSIBLE
SYNTHESIS
185
IONOMERS:
YET
ANOTHER
APPROACH
TO
REVERSIBLE
COSSLINKING
188
SUMMARY
190
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
7
191
8
8.1
8.2
ETHYLENE
AND
PROPYLENE:
TWO
VERY
DIFFERENT
KINDS
OF
CHEMISTRY
195
ETHYLENE
AND
PROPYLENE
195
THE
INDUSTRIAL
IMPORTANCE
OF
ETHYLENE
AND
PROPYLENE
195
XII
CONTENTS
8.3
ETHYLENE
OXIDE
AND
PROPYLENE
OXIDE
ARE
VERY
LARGE
VOLUME
INDUSTRIAL
INTERMEDIATES
DERIVED
FROM
ETHYLENE
AND
PROPYLENE
BUT
MUST
BE
INDUSTRIALLY
SYNTHESIZED
IN
ENTIRELY
DIFFERENT
WAYS
197
8.4
THE
PRODUCTION
OF
PROPYLENE
OXIDE
WITHOUT
USING
CHLORINE
198
8.5
WHY
DID
DOW
MAINTAIN
THE
HYPOCHLOROUS
ROUTE
TO
PROPYLENE
OXIDE?
201
8.6
BEFORE
WE
CONTINUE
TO
INVESTIGATE
THE
DIFFERENCE
IN
THE
INDUSTRIAL
CHEMISTRY
OF
ETHYLENE
AND
PROPYLENE,
LEFS
TAKE
A
DIVERSION
FROM
THE
MAIN
THEME
OF
THE
CHAPTER.
WHY
ARE
ETHYLENE
OXIDE
AND
PROPYLENE
OXIDE
SO
IMPORTANT
TO
THE
CHEMICAL
INDUSTRY?
WE
FIND
OUT
BY
ADDING
WATER
201
8.7
ANY
PROCESS
THAT
COULD
PRODUCE
ETHYLENE
GLYCOL
WITHOUT
OLIGOMERIC
PRODUCTS
WOULD
BE
HIGHLY
DESIRABLE
204
8.8
WE
'
VE
SEEN
THE
PROBLEMS
ARISING
FROM
THE
ALLYLIC
HYDROGENS
IN
PROPYLENE.
DOES
THE
REACTIVITY
OF
THESE
HYDROGENS
BESTOW
ANY
ADVANTAGES?
204
8.9
THE
IMPORTANCE
OF
POLYACRYLIC
ACID
AND
ITS
ESTERS
204
8.10
THE
IMPORTANCE
OF
ACRYLONITRILE
AND
POLYACRYLONITRILE
206
8.11
HOW
WAS
ARYLONITRILE
PRODUCED
IN
THE
"
OLD
DAYS
"
BEFORE
THE
"
PROPYLENE
APPROACH
"
TOOK
OVER?
209
8.12
HOW
WAS
ACRYLIC
ACID
PRODUCED
IN
THE
"
OLD
DAYS
"
BEFORE
THE
"
PROPYLENE
APPROACH
"
TOOK
OVER?
209
8.13
AN
EARLY
EXAMPLE
OF
TRANSITION
METAL
CATALYSIS
LED
TO
A
DIRECT
ROUTE
FROM
ACETYLENE
TO
ACRYLIC
ACID
211
8.14
THE
OXIDATION
OF
PROPYLENE
TO
ACRYLIC
ACID
AND
TO
ACRYLONITRILE
SHUTS
DOWN
ALL
PREVIOUS
PROCESSES.
THE
CATALYST
IS
THE
KEY,
BUT
THE
ALLYLIC
HYDROGENS
ARE
ESSENTIAL
212
8.15
SUMMARY
217
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
8
218
9
THE
DEMISE
OF
ACETALDEHYDE:
A
STORY
OF
HOW
THE
CHEMICAL
INDUSTRY
EVOLVES
221
9.1
AN
INTERESTING
EXAMPLE
OF
SHUTDOWN
ECONOMICS
221
9.2
AN
ASPECT
OF
THE
EVOLUTION
OF
THE
CHEMICAL
INDUSTRY
THAT
BEGINS
WITH
WORLD
WAR
I
223
9.3
THE
ALDOL
CONDENSATION
LEADS
TO
N-BUTANOL
224
9.4
REACTIVITY
PRINCIPLES
ASSOCIATED
WITH
THE
ALDOL
CONDENSATION
226
9.5
PENTAERYTHRITOL
AND
OTHER
POLYHYDRIC
ALCOHOLS
SYNTHESIZED
VIA
ALDOL
CONDENSATIONS
229
9.6
A
PROMINENT
"
PLASTICIZER
"
IS
SYNTHESIZED
VIA
AN
ALDOL
CONDENSATION
232
9.7
THE
GRANDFATHER
MOLECULE
OF
THE
ALDOL
CONDENSATION
IS
ACETALDEHYDE.
HOW
WAS
AND
IS
ACETALDEHYDE
PRODUCED?
234
9.8
A
PALLADIUM-BASED
PROCESS,
THE
WACKER
REACTION,
SHUTS
DOWN
ALL
OLDER
INDUSTRIAL
METHODS
TO
ACETALDEHYDE
236
9.9
HYDROFORMYLATION
-
ANOTHER
TRIUMPH
FOR
TRANSITION
METALS
238
9.10
HOW
IS
THE
OTHER
PRODUCT,
ACETIC
ACID,
WHICH
FORMERLY
WAS
MADE
FROM
ACETALDEHYDE,
NOW
PRODUCED?
243
9.11
SUMMARY
244
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
9
246
CONTENTS
I
XIII
10
DOING
WELL
BY
DOING
GOOD
249
10.1
MANY
COMPANIES
IN
THE
CHEMICAL
INDUSTRY
HAVE
BEEN
AMAZED
TO
LEARN
THAT
REPLACEMENT
OF
DANGEROUS
AND/OR
TOXIC
CHEMICALS
LEADS
NOT
ONLY
TO
SAFETY,
BUT
ALSO
TO
GREATER
PROFIT
249
10.2
WHAT
'
S
THE
PROBLEM
WITH
ACETYLENE?
FIRST,
IT
IS
EXPLOSIVE
249
10.3
WHAT
ELSE
IS
WRONG
WITH
ACETYLENE?
251
10.4
WHAT
IS
THE
PRECISE
CHEMICAL
NATURE
OF
THESE
CARBIDE
SALTS?
252
10.5
IS
ACETYLENE
DERIVED
FROM
CALCIUM
CARBIDE
OF
COMMERCIAL
IMPORTANCE?
254
10.6
LARGE-SCALE
PRODUCTION
OF
ACETYLENE
255
10.7
HOW
WAS
ACETYLENE
USED
TO
PRODUCE
INDUSTRIAL
INTERMEDIATES?
258
10.8
REPLACING
ACETYLENE
WITH
ETHYLENE
AND
ZINC
WITH
PALLADIUM
FOR
THE
PRODUCTION
OF
VINYL
ACETATE
260
10.9
WHAT
IS
VALUABLE
ABOUT
VINYL
ACETATE?
262
10.10
REPLACING
ACETYLENE
WITH
ETHYLENE
FOR
THE
PRODUCTION
OF
VINYL
CHLORIDE
265
10.11
THE
PRODUCTION
OF
1,4-BUTYNEDIOL
SHOWS
AN
ENTIRELY
DIFFERENT
FACE
OF
ACETYLENE
REACTIVITY
268
10.12
PHOSGENE
AND
CHLORINE
-
THE
POISON
GASES
OF
WORLD
WAR
I.
CAN
THEIR
REPLACEMENT
FOR
INDUSTRIAL
PROCESSES
BY
SAFER
CHEMICALS
ALSO
BE
AN
EXAMPLE
OF
"
DOING
WELL
BY
DOING
GOOD?
"
273
10.13
IS
THERE
A
WAY
TO
ELIMINATE
PHOSGENE
IN
THE
INDUSTRIAL
SYNTHESIS
OF
POLYCARBONATE?
274
10.14
LET'S
LOOK
AT
ANOTHER
COMPETITION,
THE
PRODUCTION
OF
METHYL
METHACRYLATE,
IN
TERMS
OF
CASH
AND
FINANCE
COSTS
281
10.15
REDUCING
THE
USE
OF
CHLORINE
IN
INDUSTRIAL
PROCESSES
282
10.16
HCN
IS
A
DANGEROUS
CHEMICAL
HASTENING
ITS
REPLACEMENT
IN
THE
SYNTHESIS
OF
METHYL
METHACRYLATE,
AS
WE
HAVE
SEEN.
BUT
ITS
EXQUISITE
REACTIVITY
HAS
FOSTERED
ITS
USE
IN
OTHER
PROCESSES
AND
PARTICULARLY
IN
A
POTENTIAL
PROCESS
FOR
GETTING
RID
OF
AMMONIUM
SULFATE
AS
A
BYPRODUCT
IN
THE
SYNTHESIS
OF
NYLON
6
283
10.17
ROUTES
TO
CAPROLACTAM
THAT
AVOID
PRODUCTION
OF
AMMONIUM
SULFATE
284
10.18
SUMMARY
287
STUDY
GUIDE
PROBLEMS
FOR
CHAPTER
10
289
AN
EPILOGUE
-
THE
FUTURE
293
INDEX
297 |
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| author | Green, Mark M. 1956- Wittcoff, Harold A. |
| author_GND | (DE-588)124887813 |
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| classification_tum | CIT 700f CIT 450f |
| ctrlnum | (OCoLC)249028588 (DE-599)BVBBV014620649 |
| dewey-full | 547 661.8 |
| dewey-hundreds | 500 - Natural sciences and mathematics 600 - Technology (Applied sciences) |
| dewey-ones | 547 - Organic chemistry 661 - Technology of industrial chemicals |
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| dewey-search | 547 661.8 |
| dewey-sort | 3547 |
| dewey-tens | 540 - Chemistry and allied sciences 660 - Chemical engineering |
| discipline | Chemie / Pharmazie Werkstoffwissenschaften Chemie-Ingenieurwesen |
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| genre | (DE-588)4123623-3 Lehrbuch gnd-content |
| genre_facet | Lehrbuch |
| id | DE-604.BV014620649 |
| illustrated | Illustrated |
| indexdate | 2024-08-23T00:20:39Z |
| institution | BVB |
| isbn | 3527302891 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-009937039 |
| oclc_num | 249028588 |
| open_access_boolean | |
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| physical | XX, 321 S. graph. Darst. |
| publishDate | 2003 |
| publishDateSearch | 2003 |
| publishDateSort | 2003 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Green, Mark M. 1956- Verfasser (DE-588)124887813 aut Organic chemistry principles and industrial practice M. M. Green ; H. A. Wittcoff Weinheim Wiley-VCH 2003 XX, 321 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Technische organische Chemie - Lehrbuch Chemical engineering Chemistry, Organic Technische organische Chemie (DE-588)4184575-4 gnd rswk-swf (DE-588)4123623-3 Lehrbuch gnd-content Technische organische Chemie (DE-588)4184575-4 s DE-604 Wittcoff, Harold A. Verfasser aut DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009937039&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Green, Mark M. 1956- Wittcoff, Harold A. Organic chemistry principles and industrial practice Technische organische Chemie - Lehrbuch Chemical engineering Chemistry, Organic Technische organische Chemie (DE-588)4184575-4 gnd |
| subject_GND | (DE-588)4184575-4 (DE-588)4123623-3 |
| title | Organic chemistry principles and industrial practice |
| title_auth | Organic chemistry principles and industrial practice |
| title_exact_search | Organic chemistry principles and industrial practice |
| title_full | Organic chemistry principles and industrial practice M. M. Green ; H. A. Wittcoff |
| title_fullStr | Organic chemistry principles and industrial practice M. M. Green ; H. A. Wittcoff |
| title_full_unstemmed | Organic chemistry principles and industrial practice M. M. Green ; H. A. Wittcoff |
| title_short | Organic chemistry principles and industrial practice |
| title_sort | organic chemistry principles and industrial practice |
| topic | Technische organische Chemie - Lehrbuch Chemical engineering Chemistry, Organic Technische organische Chemie (DE-588)4184575-4 gnd |
| topic_facet | Technische organische Chemie - Lehrbuch Chemical engineering Chemistry, Organic Technische organische Chemie Lehrbuch |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009937039&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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