Elaine T. Valeza

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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).