Quinoline: Iso-Quinoline ( 95% Pure) Can Be Isolated by Treating A Crude Fraction

Speight_Part II_Q & R 11/8/01 3:11 PM Page 2.
442
QUINOLINE
Replacing one carbon atom of naphthalene with a nitrogen atom creates the
isomeric quinoline (melting point: –15.6oC, boiling point: 238oC, density:
1.0929) and iso-quinoline (melting point: 26.5oC, boiling point: 243oC,
density: 1.0986).
Quinoline is isolated from coal-tar distillates in a process in which the
tar acids are removed by caustic extraction, and the oil is distilled to pro-
duce the methylnaphthalene fraction (230 to 280oC). Washing with dilute
sulfuric acid produces sulfate salts, from which the tar bases are liberated
by treatment with caustic followed by distillation. The composition of this
product is typically 92% quinoline and 5% iso-quinoline by weight with
smaller amounts of all monomethylquinolines, 2,8-dimethylquinoline, and
some homologues of iso-quinoline.
Iso-quinoline (>95% pure) can be isolated by treating a crude fraction
with hydrochloric acid followed by addition of an alcoholic solution of
cupric chloride in a mole ratio of 1:2 CuCl2/iso-quinoline.
See Naphthalene.
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Speight_Part II_Q & R 11/8/01 3:11 PM Page 2.443
ISO-QUINOLINE
See Quinoline.
2.443
RARE GASES
Oxygen (approximately 20% by volume) and nitrogen (approximately 80%

by volume) are the primary components of the atmosphere, but air also con-
tains argon, neon, krypton, and xenon (approximately 1% by volume).
Argon, neon, krypton, and xenon are all produced commercially as by-
products from large cryogenic air separation plants. The distillation of liq-
uid air is normally performed in the double-column arrangement (Fig. 1).
The rare gases are produced in side columns operated in conjunction with
the standard double-column plant.
Cold nitrogen vapor
Upper or
low-
Cold waste nitrogen
pressure
Cold air
column
Condenser
Liquid feed to upper column
Air (vapor)
Accumulated
Condenser
Liquid oxygen
liquid oxygen
Lower or
high-
pressure
column
FIGURE 1 A double-column distillation unit for production of rare gases.
2.444
RARE GASES 2.445
Since argon boils at a temperature just below oxygen, its concentra-

tion level builds up in the upper column at a point above the oxygen prod-
uct level. The argon-rich vapor is withdrawn from the upper column and
is fed to a side argon column. The liquid reflux from the argon column is
returned to the upper column at the same point as the vapor withdrawal.
The crude argon product is withdrawn from the top of the argon column.
The crude argon, which contains oxygen and nitrogen, is processed fur-
ther to remove oxygen (by the addition of hydrogen and subsequent cat-
alytic combustion and gas drying to recover the water) and nitrogen (by
another distillation step) that produces argon having a purity of 99.999%.
Neon boils at a considerably lower temperature than nitrogen and usu-
ally collects in the dome of the main condenser as a noncondensable gas.
It can be recovered by the addition of a side column.
Krypton and xenon have high boiling points relative to oxygen and
tend to accumulate in the liquid oxygen sump of the upper column of the
main plant.
Helium can be produced from natural gas. A typical plant removes the
2% helium from natural gas of up to 95 percent. The pipeline gas (at 3 to
4.5 MPa) is scrubbed, to remove water and condensable hydrocarbons
and is then passed through a gas cleaner, which removes pipeline dust.
From the cleaner, the gas goes to absorption towers to remove carbon
dioxide (using monoethanolamine) and finally passes through a bauxite
dryer. To obtain the helium, the purified gas enters coolers where the gas
is chilled to –156oC and then expanded into a separator-rectifier column.
The natural gas is liquefied and separated and the crude-helium (75%
helium, 25% nitrogen), passes through a heat exchanger counter to the
incoming gas.
The crude helium is purified by removing any trace amounts of hydro-
gen (using a reactor with a small amount of air, where the hydrogen is oxi-
dized to water over a platinum catalyst) and the hydrogen-free gas is
further purified utilizing a pressure-swing adsorption (PSA) process that
removes all contaminants to a very low level, usually less than 10 ppm.
The pressure-swing adsorption process does not remove neon but for most
helium uses it is not considered a contaminant.
RDX
See Explosives.
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RED LEAD
Red lead (Pb3O4) has a brilliant red-orange color, is quite resistant to light,
and finds extensive use as a priming coat for structural steel because it pos-
sesses corrosion-inhibiting properties.
Red lead, or minium, is manufactured by oxidizing lead to litharge
(PbO) in air and further oxidizing the litharge to red lead. In the fumed
process, which produces smaller particles, molten lead is atomized by
compressed air and then forced through the center of a gas flame, which in
turn converts it into litharge as a fume collected in filter bags. The litharge
is then oxidized to red lead by roasting in air.
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RESERPINE
Reserpine, an indole alkaloid that is obtained from the Rauwolfia plant,

was the first successful drug to treat high blood pressure.
Reserpine is isolated from its plant producers by using a nonaqueous
solvent process, using, for example, boiling methanol extraction of the
African root Rauwolfia vomitoria. Naturally, these extractions are carried
out under countercurrent methods. The methanol extract is concentrated
and acidified with 15% acetic acid and then treated with petroleum naph-
tha to remove impurities. Extraction is made using ethylene dichloride.
The solvent is neutralized with dilute sodium carbonate, evaporated to
drive off the ethylene dichloride, and further evaporated to crystallize the
crude reserpine crystals that are then crystallized.
In common with other indole derivatives, reserpine is susceptible to
decomposition by light and oxidation, so it must be stabilized. Modifying
the trimethoxyphenyl portion of the molecule gives other antihypertensive
drugs with various potency and rapidity of action.
Reserpine is used for its tranquilizing effect on the cardiovascular and
central nervous systems and as an adjunct in psychotherapy.
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ROTENONE
Rotenone is the toxic principle of several tropical and subtropical plants,

the chief of which is derris. It is a complex organic heterocyclic compound
and rotenone derivatives are stomach and contact poisons.
Ground derris roots are extracted with chloroform or carbon tetrachlo-
ride and the solvent evaporated, leaving a mixture of rotenone and some
other less toxic substances, which are not separated.
2.449
RUBBER (NATURAL)
Rubber is a natural polymer that is obtained from the rubber tree and has
the all cis-1 ,4-polyisoprene structure. This structure has been duplicated
in the laboratory and is called synthetic rubber, made with the use of
Ziegler-Natta catalysis.
Natural rubber may contain less than 10% of nonrubber chemicals and
has an outstanding heat-buildup resistance.
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RUBBER (SYNTHETIC)
Synthetic rubbers are manufactured from a variety of starting materials

that have been classified into vulcanizable and nonvulcanizable and also
by the chemical composition of the polymer chain.
The most widely used synthetic rubber is styrene-butadiene rubber (SBR)
(Fig. 1). Other commonly used elastomers are polybutadiene, polyethylene-
propylene, butyl rubber, neoprene, nitrile rubbers, and polyisoprene.
2.451
Manufacture of styrene-butadiene rubber.
FIGURE 1
2.452

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Speight_Part II_Q & R 11/8/01 3:11 PM Page 2.

Oxygen (approximately 20% by volume) and nitrogen (approximately 80%

Cold nitrogen vapor

Liquid feed to upper column

FIGURE 1 A double-column distillation unit for production of rare gases.

RARE GASES 2.445

Since argon boils at a temperature just below oxygen, its concentra-

Reserpine, an indole alkaloid that is obtained from the Rauwolfia plant,

Rotenone is the toxic principle of several tropical and subtropical plants,

Synthetic rubbers are manufactured from a variety of starting materials

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