Elaine T.

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THE PRODUCTION AND USES OF ALDEHYDES & KETONES

The Aldehydes

An aldehyde is either a functional group consisting of a terminal carbonyl group,

or a compound containing a terminal carbonyl group. An aldehyde is either a functional
group (additional info and facts about functional group) consisting of a terminal (Station
where transport vehicles load or unload passengers or goods) carbonyl group (The
bivalent radical CO), or a compound containing a terminal carbonyl group. Aldehydes
are named by IUPAC nomenclature (additional info and facts about IUPAC
nomenclature) by changing the suffix -e of the parent alkane (A non-aromatic saturated
hydrocarbon with the general formula CnH(2n+2)) to -al. Aldehydes can react with HCN
(additional info and facts about HCN) to form cyanohydrin (Any organic compound in
which the cyano radical -CN and the hydroxyl radical -OH are attached to the same
carbon atom) s, R-C(H)(OH)(CN) (wikipedia.org). Aldehydes are formed by partial
oxidation of primary alcohols and form carboxylic acids when they are further oxidized.
The common name for an aldehyde is often derived from the name of the acid it forms;
the IUPAC name is usually derived from the name of the alcohol from which it is formed.
Aldehydes are named by IUPAC nomenclature by changing the suffix -e of the parent
alkane to –al. Aldehyde condensation polumers are compounds produced by the
reaction of formaldehyde with phenol, urea or melanine. Only two aldehydes or ketones
are used to a significant degree in industry as determined by the number of tons of the
chemicals utilized. The simplest member of the aldehyde group of organic compounds,
formaldehyde, or methanal, is a colorless, sharp-smelling gas that dissolves easily in
water or alcohol. (The Columbia Encyclopedia, VI Edition. 2001-05).

Production, Effects & Uses of Aldehydes

Aldehydes are unpleasant-smelling liquids widely used in the chemical industry,

whereas aromatic aldehydes frequently have pleasant smells and are used widely as
flavourings and perfumes. Aldehydes are formed by oxidation of primary alcohols;
further oxidation yields carboxylic acids. Low molecular weight aldehydes, e.g.,
formaldehyde and acetaldehyde, have sharp, unpleasant odors; higher molecular
weight aldehydes, e.g., benzaldehyde and furfural, have pleasant, often flowery, odors
and are found in the essential oils of certain plants (chemicalland21.com)

Besides the use as an important raw material in the perfume sector, amyl
aldehyde can also be used in the production of diamyl phosphorodithioic salts in the
leather processing and lubricating oil additive sectors. The research of amyl aldehyde
application in pharmaceutical and pesticide sectors has been active in the recent years
and the market application fields are also expanding fast. The sales amount of amyl
aldehyde in the European and American markets was 40 000 - 50 000 tons a year in the
1980s (www.highbeam.com).

Deficiency, fatty aldehyde dehydrogenase: Also known as the Sjogren-Larsson

syndrome, this is a genetic (inherited) disease usually characterized by a triad of clinical
findings consisting of ichthyosis (thickened fish-like skin), spastic paraplegia (spasticity
of the legs) and mental retardation. The skin changes in the Sjogren-Larsson syndrome
are similar to those in congenital ichthyosiform erythroderma, a genetic disease that
results in fish-like, reddened skin. The Sjogren of the Sjorgren-Larsson syndrome was
Torsten Sjogren (1896-1974), professor of psychiatry at the celebrated Karolinska
Hospital in Stockholm and a pioneer in modern psychiatry and medical genetics
(medterms.com).

Treating aldehydes with oxidizing agents such as potassium permanganate, nitric

acid, or chromium oxide, will yield a carboxylic acid. Treating aldehydes with Tollens'
reagent (Ag O in aqueous ammonia) will convert aldehydes to carboxylic acids without
attacking carbon-carbon double bonds (encyclopedia.laborlawtalk.com). Excess
dichromate will further oxidise the aldehyde to form a carboxylic acid, so either the
aldehyde is distilled out as it forms (if volatile), or milder methods such as PCC
oxidation, IBX acid, Dess-Martin periodinane or Swern oxidation are used. Aldehydes
can react with water (under acidic or basic conditions) to form hydrates, R-
C(H)(OH)(OH), although these are only stable when strong electron withdrawing groups
are present, as in chloral hydrate. In old times, aldehydes were sometimes named after
the corresponding alcohols, for example "vinous aldehyde" for acetaldehyde
(wikipedia.org).

A mutation in the gene encoding for the liver mitochondrial aldehyde exists.
There is the role of alcohol dehydrogenase and aldehyde dehydrogenase isozymes in
alcohol. Aldehyde tanning is used principally in tanning white, washable leathers,
usually sheep or I am aware that aldehyde fixed tissues that are used in the confocal
are prone (ezlookfor.com).

Liver cytosolic aldehyde dehydrogenase (ALDH1) polymorphism and its

inheritance. The expression of the cytosolic aldehyde dehydrogenase 1 (Aldh1) gene in
lung tumors by northern blotting and immunocytochemical analysis. To investigate the
direct role of the human aldehyde dehydrogenase class 1 (ALDH-1) in the resistance to
one of these agents, 4-hydroperoxycyclophosphamide (4-HC), an active metabolite of
cyclophosphamide, neomycin-selectable plasmid or retroviral constructs harboring the
wild-type ALDH-1 complementary DNA in the sense orientation were transfected into
K562 leukemic cell lines.(ihop-net.org)
The Ketones

Ketone is either the functional group characterized by a carbonyl group linked to

two other carbon atoms or a compound that contains this functional group. Ketone is a
class of chemical compounds contain the carbonyl group in which the carbon atom is
covalently bonded to an oxygen atom Among the other oxygen-containing compounds,
the fact that ketones feature a carbonyl carbon bonded to two carbon atoms
distinguishes them from carboxylic acids, aldehydes, esters, and amides. Ketone bodies
are three chemicals that are produced as by-products when fatty acids are broken down
for energy. Ketone bodies are produced from acetyl-CoA (see ketogenesis) mainly in
the mitochondria of liver cells when carbohydrates are so scarce that energy must be
obtained from breaking down fatty acids. Ketones are named by appending -one to the
stem. There are 2 major kinds of ketones: diisobutyl (valerone) and methyl isobutyl
(hexone) (kidsseek.com).

Ketone has the general formula RCOR' where the groups R and R' may be the
same or different, or incorporated into a ring (R and R' are alkyl, aryl, or heterocyclic
radicals). Ketones may be prepared by several methods, including the oxidation of
secondary alcohols and the destructive distillation of certain salts of organic acids
(columbia.thefreedictionary.com)

Production, Effects & Uses of Ketones

Ketone bodies are transported from the liver to other tissues, where acetoacetate
and beta-hydroxybutyrate can be reconverted to acetyl-CoA to produce energy. Ketones
(sometimes called acetone) are chemicals which appear in the blood and urine when
body fat is being broken down for energy. Ketones also are formed when not enough
food has been eaten to provide the energy the body needs. Morning ketones can be a
sign of a low blood sugar during the night followed by rebounding or bouncing back to a
normal or high level by morning (med.umich.edu).

In the presence of an acid catalyst the ketone is subjected to so-called keto-enol

tautomerism. Acetone, acetoacetate and beta-hydroxybutyrate are ketones (or ketone
bodies) generated from carbohydrates, fatty acids and amino acids in humans and most
vertebrates. Ketones are elevated in blood after fasting including a night of sleep, and in
both blood and urine in starvation, hypoglycemia due to causes other than
hyperinsulinism, various inborn errors of metabolism, and ketoacidosis (wikipedia.org).
Ketones are elevated in blood and urine in starvation, hypoglycemia due to causes
other than hyperinsulinism, various inborn errors of metabolism and ketoacidosis
(usually due to diabetes mellitus) (reference.com).

Ketones are important intermediates in the syntheses of organic compounds

such as alkoxides, hydroxyalkynes, imines, alcohols (primary, secondary as well as
tertiary), acetals, thioacetals, phosphine oxides, geminal diols, hydrazones, organic
sulfite and cyanohydrins (chemicalland21.com).

Methyl isobutyl ketone is used as a solvent for gums, resins, paints, varnishes,
lacquers, and nitrocellulose. Methyl isobutyl ketone is used as a solvent for gums,
resins, paints, varnishes, lacquers, and nitrocellulose, as an alcohol denaturant, in the
extraction of rare metals, and as a synthetic flavoring adjuvant. Methyl isobutyl ketone
may be released to the environment in effluent and emissions from its manufacture and
use, in exhaust gas from vehicles, and from land disposal and ocean dumping of waste
that contains this compound (epa.gov). Partition coefficients for methyl isobutyl ketone:
water/air: 79; blood/air: 90; oil/air: 926 (frankmckinnon.com).

Methyl isobutyl ketone is primarily used as a solvent for gums, resins, paints,
varnishes, lacquers, and nitrocellulose, as an alcohol denaturant, in the extraction of
rare metals, and as a synthetic flavoring adjuvant (lakes-environmental.com). Methyl
isobutyl ketone may be released to the environment in effluent and emissions from its
manufacture and use, in exhaust gas from vehicles, and from land disposal and ocean
dumping of waste that contains this compound. Since methyl isobutyl ketone is a
solvent and denaturant with a wide variety of applications, a large number of industries
could potentially release this compound.

Gestational Diabetes: Testing for Ketones

The issue of ketones is particularly pertinent to large women since ketones can
be brought on by the use of low-calorie food plans, often prescribed to obese
gestational diabetics and even obese pregnant women without correct nutrition plan. As
long as these ketones are mild and are tested for and resolved, they are probably not a
huge health drain unless large levels are present and are unable to be resolved. The
consensus seems to be that small amounts on occasion are probably not a serious
problem but should be avoided if possible; larger amounts or consistent amounts are
more of a worry (plus-size-pregnancy.org).

Since ketones in the blood can be detected well before ketones in the urine,
there is the possibility to treat sooner than you would if you waited for urine testing to
show a positive result). Ketones will usually be present in the morning if you needed an
insulin shot the evening before (med.umich.edu).

Because of the importance of identifying ketones as soon as possible, everyone

with type 1 diabetes might want consider a Precision XTRA for blood ketone testing,
regardless of which blood glucose meter they use.
Ketones at the workplace

Containers of ethyl butyl ketone should be protected from physical damage and
ignition sources, and should be stored separately from acetaldehyde, perchloric acid,
and oxidizing agents such as, peroxides, chlorates, perchlorates, permanganates, and
nitrates (osha.gov)Before a worker is placed in a job with a potential for exposure to
ethyl butyl ketone, a licensed health care professional should evaluate and document
the worker's baseline health status with thorough medical, environmental, and
occupational histories, a physical examination, and physiologic and laboratory tests
appropriate for the anticipated occupational risks (epa.gov)

Ketosis: Mystery or Misconception?

Ketone bodies are precursors for the essential substance (acetyl-CoA) required
in the synthesis of lipid (myelin) in the neural cells. The concentration of ketone bodies
in the blood at any time represents a balance between the rate of their production by the
liver and the rate of their use by tissues. Acetone on the other hand is a ketone and is
present in blood and urine when the plasma concentration of acetoacetate is elevated
(bestlowcarbs.com). Ketones are a normal and efficient source of fuel and energy for
the human body. ketones are produced by the body to provide the fuel necessary for
life, since the cells can't use the sugar). Ketones will spill into the urine ONLY when
there is more in the blood than is being used as fuel by the body at that particular
moment (lowcarb.ca)

The ketone bodies have a distinctive smell, which can be detected in the breath.
Their ketone bodies levels in the blood would then be sky high; but what was making
them feel faint and dizzy were the low levels of glucose in the blood. Within minutes the
symptoms were gone, and when we tested the blood, ketone bodies could no longer be
found, and their blood sugars would be normal (academic.sun.ac.za).