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Glyoxal is an organic compound with the chemical formula OCHCHO. Glyoxal is the smallest dialdehyde (a compound with two aldehyde groups). Glyoxal is a white crystalline solid at low temperatures and close to its melting point (15 ° C). The liquid is yellow and the steam is green.
CAS NO: 107-22-2
IUPAC NAME:
Ethanedial; Glyoxal; Oxaldehyde; oxaldehyde; Oxalaldehyde; etanedial; GLYOXAL; glyoxal
TRADE NAME:
1,2-Ethanedial (chemical name); 1,2-Ethanedion; Biformal; Biformyl; Daicel GY 60; Diformil; Ethanedial (9CI); Ethanedione; Glyfix CS 50; Glyoxsal (8CI); Glyoxal (common name); Glyoxal 40 liquid; Glyoxal aldehyde; Glyoxylaldehyde; Gohsezal P; Oksal; Oxalaldehyde; Permafresh 114; Protectol GL; Protectol GL 40; Glyoxal
OTHER NAME:
1,2-Ethanedion; 107-22-2; 1732463; 203-474-9 ; 50NP6JJ975; Diformal moral; Ethanedial ; Ethanedione; Glyphosphine; Glyoxal; MFCD00006957; Oksalaldehyde; Oxalaldehyde ; Oxalaldéhyde ; 203-474-9MFCD00006957; 40% aqueous solution; 4-01-00-03625; Acetal; Biformal; Biformyl; DIFORMIL; EDO; ethane-1,2-dial; ethane-1,2-dione; Gelifundol; Glyoxal (40 percent by weight in H2O); glyoxal aldehyde; Glyoxal, 40% in water; Glyoxal, 40% solution in water; Glyoxylaldehyde; GXT; ODIX; oxal; Oxaldehyde
SYNONYM:
Ethane-1,2-dione; Ethanedial; Oxalaldehyde; 1,2-Ethanedione; Glyoxylaldehyde; Biformal; Biformyl; Diformyl; Ethanedione; Glyoxal aldehyde; Glyoxylaldehyde; Oxal; Diformal; Ethane-1,2-dione; Ethandial; Glioxal (Spanish); Glyoxal; ethane-1,2-dione; ethanedial; oxalaldehyde 1,2-ethanedione; glyoxylaldehyde; biformal; biformyl; diformyl; ethanedione; glyoxal aldehyde; glyoxylaldehyde; oxal; diformal; ethandial; glioxal (Spanish) Glyoxal; Ethane-1,2-dione; Ethanedial; Oxalaldehyde; 1,2-Ethanedione; Glyoxylaldehyde; Biformal; Biformyl; Diformyl; Ethanedione; Glyoxal aldehyde; Glyoxylaldehyde; Oxal; Diformal; Ethane-1,2-dione; Ethandial; Glioxal cas no: 107-22-2
Pure glyoxal is not commonly encountered as Glyoxal forms hydrates that oligomerize. For many purposes, these hydrated oligomers behave equally with glyoxal. Glyoxal is produced industrially as its primary precursor. Anhydrous glyoxal is a liquid at ambient temperature; It crystallizes in the form of yellow prismatic crystals at 15 ° C. Glyoxal Anhydrous can only be made in a laboratory and is not available in a stable form. Glyoxal is commonly supplied in the form of a 40% (w / w) (expressed as CHOCHO) aqueous solution. Less concentrated forms were previously commercialized (essentially 30% w / w). Glyoxal is produced in very small quantities of 80% powder (less than 0.1% of marketed quantities).
Hydrated monomer (ethane bis-gemdiol) is the main form of glyoxal in aqueous solution. However, this gemdiol tends to polymerize into acetals and semi-acetals. Polymerization depends on both the pH and the concentration of the solution. The main oligomeric forms are dioxolane dimer and bis (dioxolane) trimer. Glyoxal is mainly marketed as a 40% aqueous solution. Glyoxal is used as the starting point for the production of a number of other compounds. Dual functionality and the ability of glyoxal to form heterocyclic compounds are used in resin manufacture and crosslinking functionalized macromolecules such as cellulose, polyacrylamides, polyvinyl alcohol, keratin, and other polycondensates.
With cellulose, unstable hemiacetals are obtained which irreversibly form acetal when heated in the cold in the presence of acid catalysts. Annex I of the Cosmetic Directive lists a variety of cosmetic products using hydroxyl-ethyl cellulose R-types (e.g. creams, emulsions, lotions, gels and oils for the skin, face masks, colored bases, different powders (make-up, after bathing), hygienic) , hair care products (colorants, bleaches, cleaning and care products), shaving products, sunbathing, tanning, etc.). The maximum glyoxal level in the cosmetic product is 100 ppm. In finished cosmetic products, glyoxal is only found as leftovers from polymerization reactions. Glyoxal exhibits a wide variety of activities, eg. as a versatile crosslinker, as an intermediate for organic synthesis, as a biocide and as a scavenger for various nucleophiles.
Glyoxal is an organic compound with a complex structure. In liquid state it is yellow in color and turns into a green colored gas when Glyoxal evaporates. Compound is generally the preferred choice for use in many different types of manufacturing. The substance can be purchased for those who use glyoxal in the manufacture of their products. Glyoxal's chemical formula is OCHCHO or C2H2O2. It is the smallest dialdehyde with a more complex structure. The compound is usually prepared using the Laporte process or through the liquid phase ox. Glyoxal is used for crosslinking starch-based formulas on textile substrates and coated papers. Glyoxal is also used in textile production, leather tanning, cosmetics, epoxy, oil and gas industries and disinfection. Glyoxylic acid has industrial uses, including hardening wood and hardening wood. Glyoxal is also used as a fixative in the method of protecting cells to be examined under a microscope. Various concentrations are used for different types of use.
There are many specific uses in the production of various products. For example, Glyoxal is used both in the health sector and in disinfectants used for veterinary hygiene. Glyoxal increases the viscosity of products when used in cosmetics. Helps maintain leather quality in leather production. Glyoxal is often used to provide greater stability and better performance in epoxy. It is also accredited for use in food packaging production. Glyoxal is important to note that it is readily biodegradable when used according to OECD guidelines. Glyoxal reacts vigorously with strong oxidizing agents such as nitric acid. If glyoxal is anhydrous, Glyoxal polymerizes rapidly even at low temperatures. Aqueous solutions are more stable but also polymerize when stored. Reacts with itself to give gluconates in the presence of base.
Glyoxal undergoes addition and condensation reactions, which can be exothermic with amines, amides, aldehydes and materials containing hydroxides. Glyoxal is a skin and eye irritant; the effect can be mild to severe. Its vapors irritate the skin and respiratory tract. An amount of 1.8mg caused severe irritation to the eyes of the rabbits. Glyoxal demonstrated low toxicity in test subjects. Swallowing can cause somnolence and gastrointestinal pain. Glyoxal is dialdehyde, which is the smallest possible and consists of ethane with oxo groups at both carbons. It acts as a pesticide, pesticide and allergen. Glyoxal appears as yellow crystals that melt at 15 ° C. For this reason, it is often encountered as a light yellow liquid with a slightly sour odor. The steam has a green color and burns with a purple flame.
Glyoxal was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid. Commercial glyoxal is prepared either by gas phase oxidation of ethylene glycol in the presence of a silver or copper catalyst (Laporte process) or liquid phase oxidation of acetaldehyde with nitric acid. Glyoxal can be synthesized in the laboratory by oxidation of acetaldehyde with selenous acid. Anhydrous glyoxal is prepared by heating solid glyoxal hydrate (s) with phosphorus pentoxide and condensing the vapors in a cold trap. Glyoxal is used as a solubilizer and crosslinking agent in polymer chemistry.
Glyoxal is a valuable building block in organic synthesis, especially in the synthesis of heterocycles such as imidazoles. A suitable reagent form for use in the laboratory is bis (hemiacetal) with ethylene glycol, 1,4-dioxane-2,3-diol. This compound is commercially available. Glyoxal solutions can also be used as a fixative for histology, i.e. as a method to examine cells under a microscope. Since glyoxal and its derivatives react with free guanines in RNAs, they are also used in chemical examination of RNA structure.
Glyoxal is typically provided as a 40% aqueous solution. Like other small aldehydes, glyoxal forms hydrates. In addition, hydrates condense to give a series of oligomers, some of which have an indeterminate structure. For most applications, the exact nature of the types in the solution is unimportant. Glyoxal has been observed as a trace gas in the atmosphere, eg. as the oxidation product of hydrocarbons. Tropospheric concentrations of 0–200 ppt by volume up to 1 ppb by volume have been reported in polluted areas. Glyoxal is used in the production of textilesand glues and in organic synthesis. Glyoxal reacts vigorously with strong oxidizing agents such as nitric acid. Polymerizes rapidly even at low temperature if anhydrous [Noller]. Aqueous solutions are more stable but also polymerize on standing. Reacts with itself in the presence of base to give glyconates. Undergoes addition and condensation reactions that may be exothermic with amines, amides, aldehydes, and hydroxide-containing materials.
Mixing in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, oleum, ethyleneimine, nitric acid, sodium hydroxide. Glyoxal is a skin and eye irritant; the effectmay be mild to severe. Its vapors are irritatingto the skin and respiratory tract. Anamount of 1.8 mg caused severe irritation inrabbits’ eyes. Glyoxal exhibited low toxicityin test subjects. Ingestion may cause somnolenceand gastrointestinal pain. Glyoxal is mixed with a combustible solventand burned in a chemical incineratorequipped with an afterburner and scrubber. Inhalation causes some irritation of nose and,40% solution throat. Contact with liquid,40% solution irritates eyes and causes mild irritation of skin; stains skin yellow.
Glyoxal was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid. Commercial glyoxal is prepared either by the gas-phase oxidation of ethylene glycol in the presence of a silver or copper catalyst (the Laporte process) or by the liquid-phase oxidation of acetaldehyde with nitric acid.
The first commercial glyoxal source was in Lamotte, France, started in 1960. The single largest commercial source is BASF in Ludwigshafen, Germany, at around 60,000 tons per year. Other production sites exist also in the US and China. Commercial bulk glyoxal is made and reported as a 40%-strength solution in water. Glyoxal may be synthesized in the laboratory by oxidation of acetaldehyde with selenious acid. Glyoxal is supplied typically as a 40% aqueous solution. Like other small aldehydes, glyoxal forms hydrates. Furthermore, the hydrates condense to give a series of oligomers, some of which remain of uncertain structure. For most applications, the exact nature of the species in solution is inconsequential. At least one hydrate of glyoxal is sold commercially, glyoxal trimer dihydrate: [(CHO)2]3(H2O)2 (CAS 4405-13-4). Other glyoxal equivalents are available, such as the ethylene glycol hemiacetal 1,4-dioxane-trans-2,3-diol (CAS 4845-50-5, m.p. 91–95 °C).
Glyoxal is estimated that, at concentrations less than 1 M, glyoxal exists predominantly as the monomer or hydrates thereof, i.e., OCHCHO, OCHCH(OH)2, or (HO)2CHCH(OH)2. At concentrations above 1 M, dimers predominate. These dimers are probably dioxolanes, with the formula [(HO)CH]2O2CHCHO. Dimer and trimers precipitate as solids from cold solutions. Glyoxal has been observed as a trace gas in the atmosphere, e.g. as an oxidation product of hydrocarbons. Tropospheric concentrations of 0–200 ppt by volume have been reported, in polluted regions up to 1 ppb by volume. Glyoxal appears as yellow crystals melting at15°C. Hence often encountered as a light yellow liquid with a weak sour odor. Vapor has a green color and burns with a violet flame. Glyoxal is the dialdehyde that is the smallest possible and which consists of ethane having oxo groups on both carbons. Glyoxal has a role as a pesticide, an agrochemical and an allergen.
Glyoxal is used to produce glycoluril based amino crosslinking resins for powder coatings, liquid can and coil coatings. Glyoxal emits less formaldehyde and produce more flexible films compared to other amino crosslinkers. Glyoxal is a building block for the glycidated phenol compound (tetraglycidyl ether of tetrakis(4-hydroxyphenyl) ethane). This increases stability in epoxy laminates and molding compounds. The sulfur scavenging property of Glyoxal to act as a H2S scavenger and glyoxal-crosslinked polymers (hydrocolloids) can be used to improve viscosity in oil-drilling fluids. Polymers crosslinked with Glyoxal are used to enhance the wet/dry strength and enable the efficient coating of paper. In cosmetics, Glyoxal-crosslinked polymers (hydrocolloids) improves the viscosity.
As a crosslinker, Glyoxal is used in antiwrinkle and softening polymer. Glyoxal is also used as a crosslinker in leather tanning processes. The biocidal effect of glyoxal is used in water treatment.
Glyoxal is used to crosslink a wide range of other polymers, including starch, cellulose, proteinaceous material, polyacrylamide and polyvinyl alcohols. In disinfection applications, Glyoxal is a biocidal active ingredient. Finally, Glyoxal can be used in wood hardening application for improved moisture resistance.Glyoxal (OHC–CHO) is a dialdehyde that can be obtained from several natural sources, such as from the oxidation of lipids or as a by-product of biological processes. The low vapor tension of the glyoxal solution and its low toxicity are some of the advantages of using glyoxal instead of formaldehyde. The two adjacent carbonyl groups make glyoxal highly reactive. Glyoxal is already used as a formaldehyde substitute in wood adhesive applications.
Glyoxal is an organic compound with a complex structure. In its liquid state it is yellow in color and when it evaporates it turns to a green colored gas. The compound is often a preferred choice for use in many different types of manufacturing. Glyoxal is available for purchase to those who use it in the manufacturing of their products. The chemical formula for Glyoxal is OCHCHO or C2H2O2. It’s the smallest dialdehyde which is a more complex structure. Glyoxal is commonly prepared using the Laporte process or through the liquid-phase oxidation of acetaldehyde with nitric acid. It was first produced commercially in France in 1960. Since then, there have been many uses found for this compound. Glyoxal is used in a great many instances as a solubilizer, an agent that increases the solubility of a substance. For this reason Glyoxal is used commonly as an additive to many commercial formulas where increased solubility is desired. Glyoxal is also known as ethanedial or ethane 1,2-dione. Another common name is Glyoxyladehyde. It is provided as SDS Glyoxal40; it has 40% strength. Glyoxal is a colorless, transparent liquid with a content of 40% plus or minus .5%.
Glyoxal is used to crosslink starch-based formulas in textile finishes and in coated paper. It’s also used in textile production, leather tanning, cosmetics, epoxy, oil and gas industries and disinfection. Glyoxylic acid has industrial uses including the curing of wood and wood hardening. Glyoxal is also used as a fixative in a method of preserving cells for examination under a microscope. Various concentrations are used in different types of uses. There are many specific uses in the manufacturing of various products. For example, Glyoxal is used in disinfectants that are used both in the health industry and for veterinary hygiene. When used in cosmetics it improves the viscosity of the products. In leather production, Glyoxal helps preserve the leather quality. Glyoxal is often used in epoxy to give it more stability and better performance. Glyoxal is also accredited for use in the manufacture of food packaging. Glyoxal is important to note that it is readily biodegradable when used according to OECD guidelines. Industrial chemicals such as Glyoxal can be ordered in quantities with a minimum of a 55 gallon drum. Both small and large manufacturers may order the compound. Glyoxal is available in bulk through tank trucks, drums, and totes.
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