2-Furyl-methanal
Bezeichnung:2-Furyl-methanal
CAS-Nr98-01-1
Englisch Name:Furfural
CBNumberCB9182277
SummenformelC5H4O2
Molgewicht96.08
MOL-Datei98-01-1.mol
Synonyma
2-Furaldehyd
2-Furyl-methanal
2-Furancarboxaldehyd
2-Furylmethanal
2-Furyl-methanal physikalisch-chemischer Eigenschaften
Schmelzpunkt | -36 °C (lit.) |
Siedepunkt | 162 °C (lit.) |
Dichte | 1.16 g/mL at 25 °C (lit.) |
Dampfdichte | 3.31 (vs air) |
Dampfdruck | 13.5 mm Hg ( 55 °C) |
FEMA | 2489 | FURFURAL |
Brechungsindex | n |
Flammpunkt | 137 °F |
storage temp. | Store below +30°C. |
Löslichkeit | 95% ethanol: soluble1ML/mL, clear |
Aggregatzustand | Liquid |
Farbe | very deep brown |
Geruch (Odor) | at 1.00 % in dipropylene glycol. sweet woody almond fragrant baked bread |
PH | >=3.0 (50g/l, 25℃) |
Explosionsgrenze | 2.1-19.3%(V) |
Geruchsart | bready |
Wasserlöslichkeit | 8.3 g/100 mL |
FreezingPoint | -36.5℃ |
Sensitive | Air Sensitive |
Merck | 14,4304 |
JECFA Number | 450 |
BRN | 105755 |
Henry's Law Constant | 1.52(x 10-6 atm?m3/mol) at 20 °C (approximate - calculated from water solubility and vapor pressure) |
Expositionsgrenzwerte | NIOSH REL: IDLH 100 ppm; OSHA PEL: TWA 5 ppm (20 mg/m3); ACGIH TLV: TWA 2 ppm (adopted). |
Dielectric constant | 41.9(20℃) |
Stabilität | Stable. Substances to be avoided include strong bases, strong oxidizing agents and strong acids. Flammable. |
LogP | 0.41 |
CAS Datenbank | 98-01-1(CAS DataBase Reference) |
IARC | 3 (Vol. 63) 1995 |
NIST chemische Informationen | 2-Furancarboxaldehyde(98-01-1) |
EPA chemische Informationen | Furfural (98-01-1) |
Kennzeichnung gefährlicher | T,Xi |
R-Sätze: | 21-23/25-36/37-40-36/37/38 |
S-Sätze: | 26-36/37/39-45-1/2-36/37 |
RIDADR | UN 1199 6.1/PG 2 |
WGK Germany | 2 |
RTECS-Nr. | LT7000000 |
F | 1-8-10 |
Selbstentzündungstemperatur | 599 °F &_& 599 °F |
Hazard Note | Irritant |
TSCA | Yes |
HS Code | 2932 12 00 |
HazardClass | 6.1 |
PackingGroup | II |
Giftige Stoffe Daten | 98-01-1(Hazardous Substances Data) |
Toxizität | LD50 orally in rats: 127 mg/kg (Jenner) |
IDLA | 100 ppm |
Gefahreninformationscode (GHS)
-
Bildanzeige (GHS)
-
Alarmwort
Achtung
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Gefahrenhinweise
H226:Flüssigkeit und Dampf entzündbar.
H301:Giftig bei Verschlucken.
H312:Gesundheitsschädlich bei Hautkontakt.
H315:Verursacht Hautreizungen.
H319:Verursacht schwere Augenreizung.
H330:Lebensgefahr bei Einatmen.
H335:Kann die Atemwege reizen.
H351:Kann vermutlich Krebs verursachen.
H412:Schädlich für Wasserorganismen, mit langfristiger Wirkung.
-
Sicherheit
P210:Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P273:Freisetzung in die Umwelt vermeiden.
P280:Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P303+P361+P353:BEI BERÜHRUNG MIT DER HAUT (oder dem Haar): Alle kontaminierten Kleidungsstücke sofort ausziehen. Haut mit Wasser abwaschen oder duschen.
P305+P351+P338:BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
Furfural Chemische Eigenschaften,Einsatz,Produktion Methoden
-
ERSCHEINUNGSBILD
FARBLOSE BIS GELBE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH. VERFäRBT SICH ROTBRAUN BEI KONTAKT MIT LUFT UND LICHT. -
PHYSIKALISCHE GEFAHREN
Die Dämpfe sind schwerer als Luft. -
CHEMISCHE GEFAHREN
Polymerisiert unter Einfluss von Säuren oder Basen unter Feuer- und Explosionsgefahr. Reagiert sehr heftig mit Oxidationsmitteln. Greift viele Kunststoffe an. -
ARBEITSPLATZGRENZWERTE
TLV: 2 ppm (als TWA); Hautresorption; Krebskategorie A3 (bestätigte krebserzeugende Wirkung beim Tier mit unbekannter Bedeutung für den Menschen); BEI vorhanden (ACGIH 2005).
MAK: Hautresorption; Krebserzeugend Kategorie 3B; (DFG 2005).
-
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken. -
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt die Augen, die Haut und die Atemwege. -
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Die Flüssigkeit entfettet die Haut. Möglich sind Auswirkungen auf die Leber. -
LECKAGE
Persönliche Schutzausrüstung: Umgebungsluftunabhängiges Atemschutzgerät. Ausgelaufene Flüssigkeit in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Umwelt gelangen lassen. -
R-Sätze Betriebsanweisung:
R21:Gesundheitsschädlich bei Berührung mit der Haut.
R23/25:Giftig beim Einatmen und Verschlucken.
R36/37:Reizt die Augen und die Atmungsorgane.
R40:Verdacht auf krebserzeugende Wirkung. -
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S1/2:Unter Verschluss und für Kinder unzugänglich aufbewahren. -
Aussehen Eigenschaften
C5H4O2; Furfurol, 2-Furylmethanal, Furaldehyd, Furfuraldehyd. Fablose bis rötlich braune, nach Bittermandel riechende Flüssigkeit. Wenig wasserlöslich und schwerer als Wasser. -
Gefahren für Mensch und Umwelt
Giftig beim Einatmen und Verschlucken. Hautresorption möglich.
Reitz die Augen und Haut. Wirkt stark tränenreizend. Kann zu Lungenödem und Nervenschäden wie Krämpfe, Zittern und Lähmungen führen.
Zu vermeidende Stoffe sind starke Oxidationsmittel und Alkalihydroxide. Empfindlich gegen Reibung und Licht.
LD50 (oral, Ratte): 65 mg/kg. -
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Spritzschutz. -
Verhalten im Gefahrfall
Mit flüssigkeitsbindendem Material z. B. Rench Rapid aufnehmen, der Entsorgung zuführen.
Kohlendioxid, Wassernebel, Schaum, Pulver. -
Erste Hilfe
Nach Hautkontakt: Sofort mit viel Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser und geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Viel Wasser trinken lassen, möglichst mit Aktivkohlezusatz. Erbrechen auslösen. Sofort Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag -
Sachgerechte Entsorgung
Als halogenfreie, organische Lösemittelabfälle. -
Beschreibung
Furfural is a colourless to amber-like oily liquid with an almond-like odour. On exposure to light and air, it turns reddish brown. Furfural is used in making chemicals, as a solvent in petroleum refining, a fungicide, and a weed killer. It is incompatible with strong acids, oxidisers, and strong alkalis. It undergoes polymerisation on contact with strong acids or strong alkalis. Furfural is produced commercially by the acid hydrolysis of pentosan polysaccharides from non-food residues of food crops and wood wastes. It is used widely as a solvent in petroleum refining, in the production of phenolic resins, and in a variety of other applications. Human exposure to furfural occurs during its production and use, as a result of its natural occurrence in many foods and from the combustion of coal and wood. -
Chemische Eigenschaften
Furfural is a colorless to yellow aromatic het erocyclic aldehyde with an almond-like odor. Turns amber on exposure to light and air. -
Chemische Eigenschaften
Furfural has a characteristic penetrating odor typical of cyclic aldehydes. Furfural is prepared industrially from pentosans that are contained in cereal straws and brans; these materials are previously digested with diluted H2S04, and the formed furfural steam is distilled. -
Physikalische Eigenschaften
Colorless to yellow liquid with an almond-like odor. Turns reddish brown on exposure to light and air. Odor and taste thresholds are 0.4 and 4 ppm, respectively (quoted, Keith and Walters, 1992). Shaw et al. (1970) reported a taste threshold in water of 80 ppm. -
Occurrence
Reported found in several essential oils from plants of the Pinaceae family, in the essential oil from Cajenne linaloe, in the oil from leaves of Trifolium pratense and Trifolium incarnatum, in the distillation waters of several essential oils, such as ambrettee and angelica seeds, in Ceylon cinnamon essential oil, in petitgrain oil, ylang-ylang, lavender, lemongrass, calamus, eucalyptus, neroli, sandalwood, tobacco leaves and others Also reported found in many foods including apple, apricot, citrus peel oils and juices, berries, guava, grapes, pineapple, asparagus, kohlrabi, celery, onion, leek, potato, tomato, cinnamon, mustard, bread, cheeses, meats, fsh, cognac, rum, whiskies, cider, grape wine, cocoa, coffee, tea, barley, peanuts, popcorn, pecans, oats, honey, soybeans, passion fruit, plums, mushroom, mango, tamarind, fruit brandies, whiskey malt, white bread, rum, bourbon, cardamom, coriander seed, calamus, corn oil, malt, wort and other sources -
Verwenden
Commercially, furfural is produced through hydrolysis of pentosan in agricultural byproducts (e.g., crop wastes). It has a diverse applications which include as a solvent in various manufacturing industries (e.g., petroleum and automotive products), accelerant for vulcanization of rubber, raw material for manufacturing furan derivatives (e.g., tetrahydrofurfuryl alcohol) and synthetic resins, wetting agent, flavoring ingredient for foods (e.g., roasted coffee), fragrance in consumer and personal care products (e.g., fragrance cream, bath products, toiletries), and pesticides for controlling unwanted microorganisms, fungi, weeds, insects, and nematodes. The application methods for pesticidal use include drip irritation, spray boom, sprinkler, and low-pressure back-pack spray. -
Verwenden
Solvent refining of lubricating oils, resins, and other organic materials; as insecticide, fungicide, germicide; an intermediate for tetrahydrofuran, furfural alcohol, phenolic and furan polymers -
Verwenden
In the manufacture of furfural-phenol plastics such as Durite; in solvent refining of petroleum oils; in the preparation of pyromucic acid. As a solvent for nitrated cotton, cellulose acetate, and gums; in the manufacture of varnishes; for accelerating vulcanization; as insecticide, fungicide, germicide; as reagent in analytical chemistry. In the synthesis of furan derivatives. -
Definition
ChEBI: An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group. -
Vorbereitung Methode
Furfural is obtained commercially by treating pentosan-rich agricultural residues (corncobs, oat hulls, cottonseed hulls, bagasse, rice hulls) with a dilute acid and removing the furfural by steam distillation. Major industrial uses of furfuraldehyde include: (1) the production of furans and tetrahydrofurans where the compound is an intermediate; (2) the solvent refining of petroleum and rosin products; (3) the solvent binding of bonded phenolic products; and (4) the extractive distillation of butadiene from other C4 hydrocarbons.
When pentoses, e.g., arabinose, xylose, are heated with dilute HCl, furfuraldehyde is formed, recognizable by deep red coloration with phloroglucinol, or by the formation, with phenylhydrazine, of furfuraldehyde phenylhydrazone C4H3O·CH : NNHC6H5, solid, mp 97 °C. -
synthetische
Industrially prepared from pentosans that are contained in cereal straws and brans; these materials are previously digested with diluted H2SO4, and the formed furfural steam is distilled. -
Definition
furfural: A colourless liquid,C5H4O2, b.p. 162°C, which darkenson standing in air. It is the aldehydederivative of furan and occurs invarious essential oils and in fuseloil. It is used as a solvent for extractingmineral oils and natural resinsand itself forms resins with somearomatic compounds. -
Reaktionen
Aside from a darkening in color, furfural is relatively stable thermally and does not exhibit changes in physical properties after prolonged heating up to 230°C. The reactions of furfural are typical of those of the aromatic aldehydes, although some complex side reactions occur because of the reactive ring. Furfural yields acetals, condenses with active methylene compounds, reacts with Grignard reagents, and provides a bisulfite complex. Upon reduction, furfural yields furfural alcohol; upon oxidation, it yields furoic acid. It can be decarbonylated to furan. -
Taste threshold values
Taste characteristics at 30 ppm: brown, sweet, woody, bready, nutty, caramellic with a burnt astringent nuance. -
Synthesis Reference(s)
The Journal of Organic Chemistry, 45, p. 3449, 1980 DOI: 10.1021/jo01305a015 -
Allgemeine Beschreibung
Colorless or reddish-brown mobile liquids with a penetrating odor. Flash points 140°F. Denser than water and soluble in water. Vapors heavier than air. May be toxic by ingestion, skin absorption or inhalation. -
Air & Water Reaktionen
Flammable. Furfural is sensitive to light and air. Soluble in water, with mixing. -
Reaktivität anzeigen
Furfural reacts with sodium hydrogen carbonate. Furfural also can react with strong oxidizers. An exothermic resinification of almost explosive violence can occur upon contact with strong mineral acids or alkalis. Furfural forms condensation products with many types of compounds, including phenol, amines and urea. . -
Hazard
Absorbed by skin; irritant to eyes, skin, and mucous membranes. Toxic by skin absorption; questionable carcinogen. -
Health Hazard
Vapor may irritate eyes and respiratory system. Liquid irritates skin and may cause dermatitis. -
Brandgefahr
Special Hazards of Combustion Products: Irritating vapors are generated when heated -
Flammability and Explosibility
Non flammable -
Industrielle Verwendung
Also known as furfuraldehyde, furol, and pyromuclealdehyde,furfural is a yellowish liquidwith an aromatic odor, soluble in water and inalcohol, but not in petroleum hydrocarbons. Onexposure, it darkens and gradually decomposes.Furfural occurs in different forms in variousplant life and is obtained from complex carbohydratesknown as pentosans, which occur insuch agricultural wastes as cornstalks, corncobs,straw, oat husks, peanut shells, bagasse,and rice. Furfural is used for making syntheticplastics, as a plasticizer in other synthetic resins,as a preservative in weed killers, and as aselective solvent especially for removing aromaticand sulfur compounds from lubricatingoils. It is also used for the making of butadiene,adiponitrile, and other chemicals.
Various derivatives of furfural are not used,and these, known collectively as furans, are nowmade synthetically from formaldehyde andacetylene, which react to form butyl nedole. -
Sicherheitsprofil
Confirmed carcinogen. Poison by ingestion, intraperitoneal, subcutaneous, intravenous, and intramuscular routes. Moderately toxic by inhalation and sktn contact. Human mutation data reported. A skin and eye irritant. Mutation data reported. The liquid is dangerous to the eyes. The vapor is irritating to mucous membranes and is a central nervous system poison. However, its low volatility reduces its toxicity effect. Ingestion of furfural has produced cirrhosis of the liver in rats. In industry there is a tendency to minimize the danger of acute effects resulting from exposure to it. This is particularly true because of its low volathty. Flammable liquid when exposed to heat or flame; can react with oxidizing materials. Moderate explosion hazard when exposed to heat or flame or by chemical reaction. An exothermic polymerization of almost explosive violence can occur upon contact with strong mineral acids or alkalies. Keep away from heat and open flames. Mixture with sodium hydrogen carbonate ignites spontaneously. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. -
mögliche Exposition
Furfural is used for lube oil refining and butadiene extraction; as a solvent for wood resin, nitrated cotton, cellulose acetate, and gums; in the produc tion of phenolic plastics, thermosetting resins, refined petroleum oils, dyes, and varnishes; in the manufacture of pyromucic acid, vulcanized rubber, insecticides, fungicides, herbicides, germicides, furan derivatives, polymers, and other organic chemicals. -
Erste Hilfe
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit. -
Carcinogenicity
The IARC evaluated furfural and determined that there was inadequate evidence in humans for the carcinogenicity of furfural. There is limited evidence in experimental animals for the carcinogenicity of furfural. -
Source
Furfural occurs naturally in many plants including rice (90,000–100,000 ppm), lovage roots (2 to 20 ppm), caraway, strawberry leaves, cilantro, java cintronella, cassia, ylang-ylang, sweetflag, Japanese mint, oat husks (100,000 ppm), anise, broad-leaved lavender, myrtle flowers (0–1 ppm), lemon verbena, Karaya gum (123,000 ppm), nutmeg seeds (15,000 ppm), West Indian lemongrass, licorice roots (2 ppm), cinnamon bark (3 to 12 ppm), Hyssop shoots (1–2 ppm), periwinkle leaves, rockrose leaves, and garden dill (Duke, 1992).
Identified as one of 140 volatile constituents in used soybean oils collected from a processing plant that fried various beef, chicken, and veal products (Takeoka et al., 1996).
The gas-phase tailpipe emission rate from California Phase II reformulated gasoline-powered automobile without a catalytic converter was 1.70 mg/km (Schauer et al., 2002). -
Environmental Fate
Biological. Under nitrate-reducing and methanogenic conditions, furfural biodegraded to methane and carbon dioxide (Knight et al., 1990). In activated sludge inoculum, following a 20-d adaptation period, 96.3% COD removal was achieved. The average rate of biodegradation was 37.0 mg COD/g?h (Pitter, 1976).
Photolytic. Atkinson (1985) reported an estimated photooxidation half-life of 10.5 h for the reaction of furfural with OH radicals in the atmosphere.
Chemical/Physical. Slowly resinifies at room temperature (Windholz et al., 1983). May polymerize on contact with strong acids or strong alkalies (NIOSH, 1997). -
Lager
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Furfural must be stored to avoidcontact with oxidizing materials (such as perchlorates, peroxides, chlorates, nitrates, and permanganates) and strongacids because violent reactions occur. Store in tightly closedcontainers in a cool, well-ventilated area away from heat.Sources of ignition, such as smoking and open flames areprohibited where furfural is used, handled, or stored in amanner that could create a potential fire or explosion hazard. Before entering confined space where this chemicalmay be present, check to make sure that an explosive concentration does not exist. -
Versand/Shipping
UN1199 Furaldehyde, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid. -
läuterung methode
Furfural is unstable to air, light and acids. Impurities include formic acid, .-formylacrylic acid and furan-2-carboxylic acid. Distil it in an oil bath from 7% (w/w) Na2CO3 (added to neutralise acids, especially pyromucic acid). Redistil it from 2% (w/w) Na2CO3, and then, finally fractionally distil it under vacuum. It is stored in the dark. [Evans & Aylesworth Ind Eng Chem (Anal ed) 18 24 1926.] Impurities resulting from storage can be removed by passage through chromatographic grade alumina. Furfural can be separated from impurities other than carbonyl compounds by the bisulfite addition compound. The aldehyde is steam volatile. It has been purified by distillation (using a Claisen head) under reduced pressure. This is essential as is the use of an oil bath with temperatures of no higher than 130o which is highly recommended. When furfural is distilled at atmospheric pressure (in a stream of N2), or under reduced pressure with a free flame (caution: because the aldehyde is flammable), an almost colourless oil is obtained. After a few days and sometimes a few hours, the oil gradually darkens and finally becomes black. This change is accelerated by light and occurs more slowly when it is kept in a brown bottle. However, when the aldehyde is distilled under vacuum and the bath temperature kept below 130o during the distillation, the oil develops only a slight colour when exposed to direct sunlight during several days. The distillation of very impure material should NOT be attempted at atmospheric pressure; otherwise the product darkens very rapidly. After one distillation under vacuum, a distillation at atmospheric pressure can be carried out without too much decomposition and darkening. The liquid irritates mucous membranes. Store it in dark containers under N2, preferably in sealed ampoules. [Adams & Voorhees Org Synth Coll Vol I 280 1941, Beilstein 17/9 V 292.] -
Toxicity evaluation
The limited data in animals are insufficient for deriving a plausible mechanism of toxicity. Nevertheless, aldehyde functional group is intrinsically reactive and low molecular weight aldehydes such as formaldehyde are known to interact with biologically important macromolecules such as DNA, structural proteins, and enzymes. This supposition is consistent with the toxic effects observed at multiple sites, i.e., respiratory system, nervous system, liver, and kidneys. -
Inkompatibilitäten
May form explosive mixture with air. Acids and bases can cause polymerization, causing fire or explosion hazard. Reacts violently with oxidants. Incompatible with strong acids; caustics, ammonia, ali phatic amines; alkanolamines, alromatic amines; oxidizers. Attacks many plastics. -
Waste disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinera tor equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transpor tation, treatment, and waste disposal.
Furfural Upstream-Materialien And Downstream Produkte
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