글리옥살

1.29 at 68 °F (liquid,40% solution) (USCG, 1999) - Denser than water; will sink

1.14 g/cu cm at 20 °C

Relative density (water = 1): 1.27

1.29

1.29 @ 20°C

Yellow prisms or irregular pieces turning white on cooling; opaque at 10 °C; vapors are green

Yellow crystals or light yellow liquid

greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)

Sol in anhydrous solvents

In water, miscible at 20 °C

428 °F (NTP, 1992)

428 °F

>100 °C

428 °F

124 °F at 776 mmHg (NTP, 1992)

51 °C at 776 mm Hg

104 °C

124 °F

59 °F (NTP, 1992)

15 °C for pure glyoxal and approximately -10 °C for the 40% solution

15 °C

-14 °C

59 °F

15 °C

greater than 1.0 (NTP, 1992) (Relative to Air)

2.0 (Air = 1)

Relative vapor density (air = 1): 1.27

>1

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]；H317: May cause an allergic skin reaction [Warning Sensitization, Skin]；H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332: Harmful if inhaled [Warning Acute toxicity, inhalation]；H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]

P203, P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1432) of reports.

Chemical: Ethanedial

Ethanedial is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanedial are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

2007/442

Status: Active Update: 10-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/16112；Status: Active Update: 30-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24439

Glyoxal: Does not have an individual approval but may be used under an appropriate group standard

Behavior in Fire: Heat may cause polymerization to a combustible, viscous material. (USCG, 1999)

Combustible.

A skin and mucous membrane irritant, but less irritating than formaldehyde; Emergency treatment: Oxalic acid; [HSDB] Glyoxal, a disinfectant, may cause allergic contact dermatitis among healthcare workers. [Marks, p. 339] If left on clothing, can cause reddening of skin; [CHRIS] Dust mixtures with air may be explosive; Rapidly polymerized on standing, contact with water (violently), and mixing in solvents containing water; A moderate skin and mucous membrane irritant; [Merck Index] 40% solution: A skin and eye irritant; May cause skin sensitization; [ICSC] The anhydrous form in unstable and only produced in laboratories; A strong skin sensitizer in a study of 24 humans; [Reference #1] Produced as a human metabolite; Also found in many fermented foods and beverages; Animal studies have shown the pancreas and kidney as the target organs; [Reference #2] A mild skin and severe eye irritant; Causes other liver changes and acute tubular necrosis in dermal lethal-dose studies of rabbits; [RTECS]

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethanedial is included on this list.

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 [NFPA 1991].

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use carbon dioxide, foam, powder.

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.；SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.；INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.；INGESTION: DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Well closed.

During storage it may spontaneously polymerize and ignite.

Collect leaking and spilled liquid in sealable containers as far as possible. Use face shield. (Extra personal protection: filter respirator for organic gases and vapours.)

Waste glyoxal resins from textile treatment are biodegraded by pseudomonas using the aqueous resin solution as a substrate.

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.；STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at ambient temperatures. (NTP, 1992)

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

While extent of precautions needed under various types of industrial use is not known with certainty, it would appear reasonable to handle these dialdehydes with certain precautions as used for formaldehyde and other lower molecular weight monoaldehydes. /Dialdehydes/

/If ingested/: /Get/ fresh air, rest. /If contacted with eyes/: Remove contaminated clothes, rinse skin with plenty of water or shower. /If contacted with skin/: Remove contaminated clothes, rinse skin with plenty of water or shower. /If contacted with eyes/: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. /If ingested/: Rinse mouth, refer for medical attention.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:；IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.；SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.；FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

LC50 Leuciscus idus melanotus (Orfe) 460 mg/L/96 hr /Conditions of bioassay not specified in source examined/

LC50 Leuciscus idus melanotus (Orfe) >680 mg/L/48 hr /Conditions of bioassay not specified in source examined/

LC50 Brachydanio rerio (Zebra danio) 760 mg/L/48 hr /Conditions of bioassay not specified in source examined/

LC50 Brachydanio rerio (Zebra danio) 1200 mg/L/24 hr /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for GLYOXAL (11 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that glyoxal is expected to have very high mobility in soil(SRC). Volatilization from moist soil surfaces is not expected to be an important environmental fate process given a Henry's law constant of 3.33X10-9 atm-cu m/mol(3). The potential for volatilization of glyoxal from dry soil surfaces may exist(SRC) based upon an extrapolated vapor pressure of 255 mm Hg at 25 °C(4). Screening studies using sewage seed have indicated that glyoxal is readily biodegradable(5,6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that glyoxal is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important environmental fate process(3), based on a Henry's law constant of 3.33X10-9 atm cu m/mol(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -1.66(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Glyoxal undergoes direct photolysis with an estimated atmospheric lifetime of 5 hours(8), suggesting that photolysis in sunlit surface waters may be an important environmental fate process(SRC). Glyoxal is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups. Screening studies using sewage seed have indicated that glyoxal is readily biodegradable(9,10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), glyoxal, which has an extrapolated vapor pressure of 255 mm Hg at 25 °C(2), is expected to exist solely in the vapor phase in the ambient atmosphere. Vapor-phase glyoxal is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 34 hours(SRC), calculated from its rate constant of 1.14X10-11 cu cm/molecule-sec at 25 °C(3). Glyoxal also undergoes direct photolysis in the environment, with an estimated atmospheric lifetime of 5 hours(4). Glyoxal also reacts with ozone(4); however, the rate is significantly slower than the rate of direct photolysis and reaction with hydroxyl radicals and not considered an important atmospheric degradation mechanism(4).

Glyoxal was detected in auto-oxidized edible oils (sesame, safflower and sardine oils) at levels of <1 to 5 ug/g(1). Glyoxal was identified, not quantified, as a volatile component of roasted coffee beans(2). Glyoxal is frequently detected in fermented foods and beverages(3).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；Skin Sensitizer - An agent that can induce an allergic reaction in the skin.；ACGIH Carcinogen - Not Classifiable.

Based on the available data, the CIR Panel concludes that Glyoxal is safe for use in products intended to be applied to the nail at concentrations &#8804; 1.25%. The available data are insufficient to support the safety for other uses.

Safe for use in cosmetics, with qualifications

IDENTIFICATION: Glyoxal is generally available as an aqueous solution, typically containing 30-50% glyoxal in which hydrated oligomers are present. This chemical is used as a chemical intermediate in the production of pharmaceuticals and dyestuffs, as a cross-linking agent in the production of polymers, as a biocide, and as a disinfecting agent. Due to microbial activity as well as non-enzymatic autoxidation of oil or browning reactions of saccharides, glyoxal is frequently detected in fermented food and beverages. It is found in beer, wine and tea. HUMAN EXPOSURE: The main routes of occupational exposure to glyoxal during use as a disinfectant are via inhalation and dermal absorption. The general population is exposed mainly through ingestion of glyoxal containing food, but could be exposed through polluted air in urban areas and traces of glyoxal found in drinking water. Glyoxal is endogenously produced during normal cellular metabolism by a multitude of enzyme independent pathways. Glyoxal is found in human blood and individuals with diabetes or renal failure have higher concentrations. Glyoxal is irritating to mucous membranes and acts as a skin sensitizing agent. ANIMAL/PLANT STUDIES: The acute toxicity of glyoxal in experimental animals is low to moderate, depending upon the concentration of the chemical. After inhalation exposure, local irritations of the eyes and respiratory tract as well as hyperemia and foamy secretion in the lungs predominate. After oral exposure to glyoxal, macroscopic observations include irritations to the gastrointestinal tract and congestion in the gastrointestinal tract, lung, kidney and adrenal glands. In the prominent target organs, pancreas and kidney, the toxic action of glyoxal leads to severe degenerative changes resembling those induced during diabetes. A 28 day study at high dosages of glyoxal administered to rats effects included reduced water and food intake and retardation of body weight gain. A 90 day feeding study in do

/OTHER TERRESTRIAL SPECIES/ ... Glyoxal induced meiotic abnormalities on microsporocytes of corn (Zea mats). For topinambur (Helianthus tuberosus), approx. 100 mg glyoxal/L /caused/ toxic concerning the proliferation of the rhizome fragments in an in vitro tissue culture. The NOEC (no-observedeffect concentration) was 68 mg glyoxal/L, and the EC30 value (30 % inhibition of proliferation) was 136 mg glyoxal/L.

Redness.

Redness. Pain.

Abdominal pain. Nausea. Vomiting.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=107-22-2]

Glyoxal was detected in the Tuscarora Mountain Tunnel, PA at average levels of 0.3 ug/cu m (tunnel inlet) and 93 ug/cu m (tunnel outlet)(1). The average emission factor of glyoxal in the tunnel from vehicles was estimated as 0.184 mg/km(1). Glyoxal was emitted from the tailpipe of diesel operated trucks at a rate of 2,100 ug/km(2). Glyoxal was detected in the emissions of combusted wood at levels of 670, 439 and 616 mg/kg for pine, oak and eucalyptus, respectively(3). Glyoxal was emitted from the tailpipe of light duty gasoline powered vehicles at rates of 170 ug/km (vehicles equipped with catalytic converters) and 28,000 ug/km (vehicles not equipped with catalytic converters)(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for glyoxal can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that glyoxal is expected to have very high mobility in soil(SRC).

Chemical: Ethanedial

Ethanedial is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanedial are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

2007/442

Status: Active Update: 10-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/16112；Status: Active Update: 30-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24439

Glyoxal: Does not have an individual approval but may be used under an appropriate group standard

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethanedial is included on this list.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Glyoxal is produced, as an intermediate or a final product, by process units covered under this subpart.

Glyoxal attacks the amino groups of proteins, nucleotides, and lipids with its highly reactive carbonyl groups. A sequence of non-enzymatic reactions, called glycation, yields stable advanced glycation end-products (AGEs) with a background extent of 0.1-1% of lysine and arginine residues in proteins and 1 in 1.0 X 10-7 nucleotides in DNA. ... Glyoxal forms stable adducts with guanosine by reaction with the N-1 as well as with the exocyclic nitrogen of guanine. The rate of glyoxal-guanine adduct formation is rapid under physiological conditions. A stable tricyclic glyoxal-DNA adduct is formed by covalent binding to two nitrogens of guanine under physiological conditions in vitro. Besides 8-hydroxy-deoxyguanosine, the glyoxal-deoxyguanosine (dG) adduct is one of the major deoxyguanosine oxidation products, being formed by oxygen radicals, lipid peroxidation systems, various types of oxidative stress, and UV irradiation and after in vivo exposure to beta-hydroxy-substituted N-nitrosamines.

Glyoxal ... is considered an important intermediate in the formation of advanced glycation end-products (AGEs). AGE modification alters protein function and inactivates enzymes, resulting in disturbance of cellular metabolism, impaired proteolysis, and inhibition of cell proliferation and protein synthesis. The extent of AGE modification increases with the increasing life span of proteins. Consequently, AGEs are especially associated with long-lived proteins, such as collagens, lens crystallins, and neurofilaments, but also have been identified in shorter-lived proteins, including hemoglobin, plasma proteins, lipoproteins, and intracellular proteins.

Inhibition studies in bacterial mutagenicity tests demonstrated the production of the reactive oxygen species superoxide, hydrogen peroxide, and singlet oxygen from glyoxal. The mutagenic activity of glyoxal is related to singlet oxygen, as well as to the intracellular GSH level. The hydroxyl radical plays a prominent role in glyoxal-induced DNA cleavage.

... Isolated rat hepatocytes were incubated with different concentrations of glyoxal. Glyoxal by itself was cytotoxic at 5mM, depleted GSH, formed reactive oxygen species (ROS) and collapsed the mitochondrial membrane potential. Glyoxal also induced lipid peroxidation and formaldehyde formation. Glycolytic substrates, eg fructose, sorbitol and xylitol inhibited glyoxal-induced cytotoxicity and prevented the decrease in mitochondrial membrane potential suggesting that mitochondrial toxicity contributed to the cytotoxic mechanism. Glyoxal cytotoxicity was prevented by the glyoxal traps d-penicillamine or aminoguanidine or ROS scavengers were also cytoprotective even when added some time after glyoxal suggesting that oxidative stress contributed to the glyoxal cytotoxic mechanism.

/In lab animals/...urine contained oxalic acid the day following oral administration but disappeared during the two next weeks.

The cytosolic GSH-dependent glyoxalase system is the major pathway for the detoxification of glyoxal ... Glyoxal reacts non-enzymatically with GSH with formation of a hemithioacetal, which is subsequently converted to S-glycolylglutathione by glyoxalase I. Glyoxalase II catalyses the hydrolysis of S-glycolylglutathione to glycolate, re-forming the GSH from the first reaction. The activity of glyoxalase I in situ is approximately proportional to the cytosolic concentration of GSH. When GSH is severely depleted (eg, under conditions of oxidative stress), however, 2-oxoaldehyde dehydrogenase and aldose reductase may also metabolize glyoxal. Imbalances in intracellular redox systems may impair these detoxification mechanisms, resulting in higher levels of glyoxal. A further GSH-independent route of detoxification via glyoxalase III exists.

Glyoxal is metabolized in vitro by the rat liver to oxalic acid via glycolic acid and glyoxylic acid.

In biological materials, less than 10% of the glyoxal present is in unbound forms in aqueous solution (free glyoxal and hydrates), as most of the reactive carbonyl groups are reversibly bound to cysteinyl, lysyl, and arginyl residues of proteins.

The endogenous concentrations of glyoxal in human tissues and body fluids, as with other alpha-oxoaldehydes, are limited by the high catalytic efficiency of the glyoxalase system as well as by the rapid reaction of glyoxal with proteins.

After acute and chronic oral administration, there is evidence of systemic absorption, with distribution to erythrocytes, liver, lung, kidney, pancreas, and adrenal glands. There is some qualitative evidence that glyoxal is absorbed after dermal exposure. Granular and vacuole degeneration in liver, kidney, and pancreas have been observed along with a distinct increase in blood glucose levels following dermal application.

CIR ingredient: Glyoxal

Used in paper and textile production, leather tanning, textile dyeing, embalming, curing and cross-linking polymers; Also used as biocide and disinfectant and to make proteins and other materials insoluble; [HSDB] Used in organic synthesis and glues; [Merck Index] Used predominantly as a chemical intermediate; Also used as reducing agent in the photographic industry and to make silvered mirrors; [Reference #1]

Pulp and Paper Processing [Category: Industry]；Textiles (Fiber & Fabric Manufacturing) [Category: Industry]；Working with Glues and Adhesives [Category: Other]；Using Disinfectants or Biocides [Category: Clean]；Plastic Composites Manufacturing [Category: Industry]；Leather Tanning and Processing [Category: Industry]；Photographic Processing [Category: Other]；Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

Permanent-press fabrics; dimensional stabilization of rayon and other fibers; insolubilizing agent for compounds containing polyhydroxyl groups (polyvinyl alcohol, starch and cellulosic materials); insolubilizing of proteins (casein, gelatin and animal glue); embalming fluids; leather tanning; paper coatings with hydroxyethylcellulose; reducing agent in dyeing textiles.

In paper industry for sizing, washable wall paper, treating glue surface of envelopes; in textile industry for preventing shrinking and creasing; as substitute for formaldehyde in embalming fluids.

Glyoxal is used as a chemical intermediate in the production of pharmaceuticals and dyestuffs. It is also used in the industrial production of alpha-hydroxyalkylureas (the addition of glyoxal to urea) and is industrially employed as a cross-linking agent in the production of a range of different polymers, such as textiles (e.g., permanent press fabrics), paper, and proteins. It is used as a biocide and as a disinfecting agent and is present in many products, such as cleansers used for the disinfection of surfaces.

(1972) No Data

(1975) No Data

(1987) No Data

(1972) 7.20X10+9 GRAMS

(1975) 1.07X10+9 GRAMS

(1985) 7.16X10+9 g

2023: 10,000,000 - <25,000,000 lb；2022: 25,000,000 - <40,000,000 lb；2021: 10,000,000 - <25,000,000 lb；2020: 10,000,000 - <25,000,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1976) 1.6-1.8X10+10 G ACETALDEHYDE USED

(1987) No Data

For more U.S. Production (Complete) data for GLYOXAL (9 total), please visit the HSDB record page.

80% as a chemical intermediate for dihydroxydimethylol ethylene urea for post-curing of permanent-press fabrics, 12% as a cross-linking agent in the paper industry, 8% in the manufacture of homogenized tobacco to wrap cigars, & in numerous miscellaneous applications (1972)

Oxidation of acetaldehyde with nitric acid

By oxidation of acetaldehyde by nitric or selenious acid. Lubawin, Ber. 8, 768 (1875); Wyss Ber. 10, 1366 (1877); Kolln, Ann. 416, 230 (1918); Riley et al. J Am Chem Soc 1932; Ronzio, Waugh, Org Syn, Collection Volume 3 438 (1955); by hydrolysis of dichlorodioxane: Butler, Cretcher, J Am Chem Soc, 54, 2988 (1932).

Solution of monomer are obtained on heating polymer with anethole, phenetole, safrole, methyl nonyl ketone, or benzaldehyde.

By the vapor-phase oxidation of ethylene glycol

For more Methods of Manufacturing (Complete) data for GLYOXAL (6 total), please visit the HSDB record page.

Commercially available in anhydrous form as crystalline dihydrate, or as a 40% aqueous solution which may contain polymerization inhibitors. /Dihydrate/

GRADES: 40% solution; pure, solid; VP.

Glyoxal is a dialdehyde supplied commercially as 30% aqueous solution, consisting of mixture of monomeric & polymeric hydrates along with small amounts of impurities which render the solution acid.

Glyoxal can undertake rotational isomerization between the planar cis and trans conformations, with trans-glyoxal being the more stable isomer.

...It is generally employed as an aqueous solution... in which hydrated oligomers are present due to nucleophilic addition. ...Some of the most important hydrated derivatives of glyoxal formed by nucleophilic addition in aqueous solution... include the monomer ethane-1,1,2,2-tetraol (I), the dimer 2-dihydroxymethyl-(1,3)dioxolane-4,5-transdiol (II), and the trimer bis(dioxolane) (i.e., 2,2'-bi-1,3-dioxolanyl-4,4',5,5'-tetraol) (III) - both cis and trans configurations. However, the proportion of the different structures varies with concentration and pH.

Wholesale and Retail Trade；Petroleum Refineries；Synthetic Dye and Pigment Manufacturing；Paint and Coating Manufacturing；Not Known or Reasonably Ascertainable；Construction；All Other Chemical Product and Preparation Manufacturing；Paper Manufacturing；All Other Basic Organic Chemical Manufacturing；Other (requires additional information)

Ethanedial: ACTIVE