Methenamin

Bezeichnung:Methenamin

CAS-Nr100-97-0

Englisch Name:Hexamethylenetetramine

CBNumberCB8852597

SummenformelC6H12N4

Molgewicht140.19

MOL-Datei100-97-0.mol

Synonyma

Methenamin

1,3,5,7-Tetraazaadamantan

Hexamin

Methenamin physikalisch-chemischer Eigenschaften

Schmelzpunkt	280 °C (subl.) (lit.)
Siedepunkt	246.7°C (rough estimate)
Dichte	1.33
Dampfdichte	4.9 (vs air)
Dampfdruck	<0.01 mm Hg ( 20 °C)
Brechungsindex	1.4260 (estimate)
Flammpunkt	482 °F
storage temp.	Store below +30°C.
Löslichkeit	H₂O: 1 M at 20 °C, clear, colorless
Aggregatzustand	Solid
pka	5.1(at 25℃)
Farbe	white
Geruch (Odor)	Odorless
PH	7-10 (100g/l, H2O, 20℃)
Wasserlöslichkeit	895 g/L (20 ºC)
Sensitive	Hygroscopic
Sublimation	263-295 ºC
Merck	14,5966
BRN	2018
Stabilität	Stable. Incompatible with strong acids, strong oxidizing agents.
LogP	-2.18--2 at 20℃
CAS Datenbank	100-97-0(CAS DataBase Reference)
NIST chemische Informationen	Hexamethylenetetramine(100-97-0)
EPA chemische Informationen	Hexamethylenetetramine (100-97-0)

Sicherheit

Kennzeichnung gefährlicher	F,Xn,Xi
R-Sätze:	11-42/43-43
S-Sätze:	16-22-24-37
RIDADR	UN 1328 4.1/PG 3
WGK Germany	1
RTECS-Nr.	MN4725000
F	9-23
Selbstentzündungstemperatur	770 °F
TSCA	Yes
HS Code	2933 69 40
HazardClass	4.1
PackingGroup	III
Giftige Stoffe Daten	100-97-0(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 9200 mg/kg

Gefahreninformationscode (GHS)

Hexamethylenetetramine Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
HYGROSKOPISCHE FARBLOSE KRISTALLEODER WEISSES KRISTALLINES PULVER.
PHYSIKALISCHE GEFAHREN
Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen oder Verbrennen unter Bildung giftiger und ätzender Gase mitFormaldehyd, Ammoniak, Cyanwasserstoffund Stickstoffoxiden. Schwache Base in wässriger Lösung. Reagiert mit starken Oxidationsmitteln und starken Säuren unter Bildung giftiger und ätzender Gase. Greift Aluminium und Zink an.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK: IIb (nicht festgelegt, aber Informationen vorhanden) Sensibilisierung der Haut; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation des Aerosols und durch Verschlucken.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch beim Dispergieren schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt leicht die Augenund die Haut.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann zu Hautsensibilisierung führen. Wiederholte oder andauernde Inhalation kann asthmatische Beschwerden hervorrufen.
LECKAGE
Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste mit viel Wasser wegspülen. Persönliche Schutzausrüstung: Atemschutzgerät, A/P2-Filter für organische Dämpfe und schädlichen Staub.
R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S22:Staub nicht einatmen.
S24:Berührung mit der Haut vermeiden.
S37:Geeignete Schutzhandschuhe tragen.
Aussehen Eigenschaften
C6H12N4; Methenamin, Formin, Urotropin. Farblose Kristalle mit aminartigem Geruch.
Gefahren für Mensch und Umwelt
Reizt die Haut und Schleimhäute, kann zu Blasen- und Nierenschäden führen.
Leichtentzündlich. Starke Erhitzung vermeiden. Nicht mit starken Oxidationsmittel, Peroxidverbindungen und Halogenkohlenwasserstoffen in Berührung bringen. Mögliche gefährliche Zersetzungsprodukte bei Brand oder Erhitzung sind Formaldehyd, Ammoniak, nitrose Gase und Cyanwasserstoff.
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Staubschutz.
Verhalten im Gefahrfall
Staubentwicklung vermeiden. Stäube nicht einatmen. Trocken aufnehmen. Der Entsorgung zuführen. Mit Wasser nachreinigen.
Kohlendioxid, Wasser im Sprühstrahl, Schaum, Pulver.
Im Brandfall Entstehung gefährlicher Dämpfe wie nitroser Gase, Blausäure und Ammoniak möglich. Mit Luft Bildung explosionsfähiger Gemische.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abspülen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen, Arzt hinzuziehen.
Nach Einatmen: Frischluft. Ggf. Atemspende oder Gerätebeatmung.
Nach Verschlucken: Viel Wasser trinken lassen, Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als Laborchemikalienrückstände fest.
Beschreibung
Hexamethylenetetramine is a hardener in epoxy resins of the bisphenol A type and can also be used as an anticorrosive agent. It is a sensitizing agent in ceramics workers.
Chemische Eigenschaften
White or almost white, crystalline powder or colourless crystals.
Verwenden
Used in the treatment of urinary track infection.
Verwenden
antibacterial, tuberculostatic
Verwenden
Hexamethylenetetramine is a versatile reagent in organic synthesis. It is used in the Duff reaction, the Sommelet reaction, and in the Delepine reaction.
Definition
A white crystalline organic compound made by condensing methanal with ammonia. It is used as a fuel for camping stoves, in vulcanizing rubber, and as a urinary disinfectant. Hexamine can be nitrated to make the high explosive cyclonite.
Definition
ChEBI: A polycyclic cage that is adamantane in which the carbon atoms at positions 1, 3, 5 and 7 are replaced by nitrogen atoms.
synthetische
Hexamethylenetetramine (also known as hexamine, hexa or HMT) is prepared from ammonia and formaldehyde:

Ammonia is passed into formalin at 20-30??C, with agitation. The resulting solution is evaporated under reduced pressure until most of the water is removed and the hexamethylenetetramine crystallizes. Yields of about 95% on both ammonia and formaldehyde can be achieved. Hexamethylenetetramine is a colourless crystalline solid which, on heating, sublimes with decomposition.
Trademarks
Uritone (Parke- Davis); Urotropin (Parke-Davis).
Allgemeine Beschreibung
Odorless white crystalline powder or colorless lustrous crystals. Sublimes in a vacuum at about 505° F with some decomposition. Solutions are strong bases (pH of 0.2 molar aqueous solution is 8.4).
Air & Water Reaktionen
Highly flammable. Burns readily on contact with a flame with a smokeless flame. Finely powdered dust is significant dust explosion hazard. Water soluble.
Reaktivität anzeigen
Hexamethylenetetramine is hygroscopic. Hexamethylenetetramine is sensitive to exposure to heat. Hexamethylenetetramine is incompatible with oxidizing agents. Hexamethylenetetramine is also incompatible with acids. Hexamethylenetetramine reacts violently with sodium peroxide. Hexamethylenetetramine reacts explosively with 1-bromopentaborane(9) at temperatures above 194° F. The complex with iodine deflagrates at 280° F. The 1:1 addition complex with iodoform has exploded at 352° F. Hexamethylenetetramine is corrosive to some metals, such as aluminum and zinc . Special Hazards of Combustion Products: Formaldehyde gas and ammonia may be given off when hot [USCG, 1999].
Hazard
Skin irritant. Flammable, dangerous fire risk.
Brandgefahr
Special Hazards of Combustion Products: Formaldehyde gas and ammonia may be given off when hot.
Flammability and Explosibility
Highly flammable
Pharmazeutische Anwendungen
Methenamine (hexamine, hexamethylenetetraamine), under the name Urotropin, was successfully used in cystitis by the German physician Nicolaier in 1895. It has no intrinsic antibacterial activity and owes its effect to decomposition in acid conditions to formaldehyde, which is non-specifically microbicidal, and ammonia. It is often used in the form of organic acid salts, methenamine hippurate and methenamine mandelate, which have been claimed (unconvincingly) to keep the urinary pH low. Mandelic acid has some antibacterial activity in its own right and is sometimes given alone as a urinary antiseptic, usually as the calcium or ammonium salt. Infection with urea-splitting organisms such as Proteus spp. causes the urine to become alkaline and methenamine is unsuitable for these infections.
Methenamine is absorbed from the gut and mainly excreted unchanged in the urine, achieving concentrations of around 2–60 mg/L, sufficient to inhibit most bacteria and yeasts. Higher concentrations are achieved by the hippurate salt. It is given in enteric-coated tablets to prevent the liberation of formaldehyde by gastric acid. There is little breakdown in the blood and no systemic effect or toxicity.
Some patients complain of gastrointestinal upset or frequent and burning micturition. Attempts to control these side effects with alkali will abolish the antibacterial effect of the drug. Contact dermatitis and anterior uveitis have occasionally been encountered. Prolonged administration or high dosage may produce proteinuria, hematuria and bladder changes. Methenamine should not be given to patients with acidosis, gout or hepatic insufficiency. There have been fears about the potential carcinogenicity of formaldehyde.
Methenamine and its salts are unsuitable for the treatment of acute urinary tract infection. Their main use, now largely supplanted by other agents, has been in the long-term prophylaxis of recurrent cystitis.
Kontakt-Allergie
Hexamethylenetetramine is used in the foundry, tire and rubber, and phenol formaldehyde resins industries and in other applications such as a hardener in epoxy resins Bisphenol A type and as an anticorrosive agent. It is an ammonia and formaldehyde releaser sometimes used in topical medicaments and cosmetics
Clinical Use
A venerable drug used for the disinfection of acidic urine, methenamine is a low-molecular-weight polymer of ammonia and formaldehyde that reverts to its components under mildly acidic conditions. Formaldehyde is the active antimicrobial component. Methenamine is used for recurrent urinary tract infections. The drug is available in various dosage forms as well as various salts, including the hippurate and mandelate.
Carcinogenicity
No significantly increased incidence of tumors was observed in rats or mice given HMTA for their lifetimes. Exposures in rats included 400 mg/day for 1 year, 10,000 ppm in drinking water for 2 years in each of three generations, 10,000 ppm in water for a lifetime (261), and up to 1000 ppm in the diet for 2 years. In mice, testing conditions included up to 10,000 ppm in drinking water for 60 weeks or 50,000 ppm for 30 weeks and a lifetime holding period, and up to 10,000 ppm in the diet for 2 years.
Injection of 25–30 g subcutaneously per mouse led to an increase in subcutaneous sarcomas in two experiments (418, 419) but not in two other studies. The relevance of this methodology to the workplace condition is questionable.
läuterung methode
It is soluble in H2O (67%), CHCl3 (10%), EtOH (8%) and Et2O (0.3%), and a 0.2M solution has a pH of 8.4. Dissolve it in hot absolute EtOH (reflux, Norit), filter using a heated funnel, cool at room temperature first, then in ice. Wash the crystals with cold Et2O, dry them in air or under a vacuum. A further crop can be obtained by adding Et2O to the filtrate. It sublimes above 260o without melting. The picrate has m 179o(dec). [pK2 0 4.85: Reilley & Schmid Anal Chem 30 947 1958, pK2 0 6.30: Pummerer & Hofmann Chem Ber 56 1255 1923.] [Beilstein 26 I 306, 26 II 200, 26 III/IV 1680.]

Hexamethylenetetramine Upstream-Materialien And Downstream Produkte

100-97-0, Hexamethylenetetramine Verwandte Suche:

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