cis-1,2,3,6-Tetrahydrophthalsureanhydrid

Bezeichnung:cis-1,2,3,6-Tetrahydrophthalsureanhydrid

CAS-Nr935-79-5

Englisch Name:cis-1,2,3,6-Tetrahydrophthalic anhydride

CBNumberCB5728570

SummenformelC8H8O3

Molgewicht152.15

MOL-Datei935-79-5.mol

Synonyma

cis-1,2,3,6-Tetrahydrophthalsureanhydrid

cis-1,2,3,6-Tetrahydrophthalsureanhydrid physikalisch-chemischer Eigenschaften

Schmelzpunkt	98 °C
Siedepunkt	234.6°C (rough estimate)
Dichte	1.2143 (rough estimate)
Dampfdichte	5.2 (vs air)
Dampfdruck	<0.01 mm Hg ( 20 °C)
Brechungsindex	1.4447 (estimate)
Flammpunkt	156 °C
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit	soluble in Toluene,Benzene
Aggregatzustand	powder to crystal
Farbe	White to Almost white
Wasserlöslichkeit	REACTS
Sensitive	Moisture Sensitive
BRN	82341
Expositionsgrenzwerte	ACGIH: TWA 0.01 mg/m3 OSHA: TWA 0.25 ppm(1 mg/m3) NIOSH: IDLH 10 mg/m3; TWA 0.25 ppm(1 mg/m3)
CAS Datenbank	935-79-5(CAS DataBase Reference)
NIST chemische Informationen	cis-1,2,3,6-Tetrahydrophthalic anhydride(935-79-5)
EPA chemische Informationen	1,3-Isobenzofurandione, 3a,4,7,7a-tetrahydro-, (3aR,7aS)-rel- (935-79-5)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	41-42/43-52/53
S-Sätze:	22-24-26-37/39-61-52/53-42/43-41
RIDADR	UN 2698 8/PG 3
WGK Germany	3
RTECS-Nr.	GW5775000
TSCA	Yes
HazardClass	8
PackingGroup	III
HS Code	29173990

Gefahreninformationscode (GHS)

cis-1,2,3,6-Tetrahydrophthalic anhydride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R41:Gefahr ernster Augenschäden.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24:Berührung mit der Haut vermeiden.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
Beschreibung
Tetrahydrophthalic anhydride is an organic compound with the formula C6H8C2O3. The compound exists as two isomers, this article being focused on the more common cis isomer. It is a precursor to other compounds including the dicarboxylic acid tetrahydrophthalic acid as well the tetrahydrophthalimide, which is a precursor to the fungicide Captan. It is a white solid that is soluble in organic solvents.
Tetrahydrophthalic anhydride, the cis isomer, is prepared by the Diels-Alder reaction of butadiene and maleic anhydride.
Chemische Eigenschaften
Tetrahydrophthalic Anhydride (THPA) is a white crystalline powder or FLAKES. It is slightly soluble in benzene and acetone and it is also sensitive to moisture.
Verwenden
cis-1,2,3,6-Tetrahydrophthalic anhydride (THPA) can be used as:
- A curing agent for epoxides.
- A chemical modifier in the modification of polystyrene via Friedel-Crafts acylation for enhancing the thermal stability of the polymer.
- A reactant for the synthesis of cis-tetrahydroisoindole-1,3-dione derivatives and cyclic diimides.
Verwenden
Tetrahydrophthalic Anhydride is an anhydride hardener mainly used in the fields of coatings, epoxy resin curing agents, polyester resins, adhesives, plasticizers, pesticides, etc. It is also used as a chemical intermediate for light colored alkyds.
Tetrahydrophthalic Anhydride is an organic compound obtained from the reaction of Maleic Anhydride and Butadiene.
synthetische
A flask containing 500 ml of dry benzene and 196 gm (2 moles) of maleic anhydride is heated with a pan of hot water while butadiene is introduced rapidly (0.6-0.8 liter/min) from a commercial cylinder. The solution is stirred rapidly and the heating is stopped after 3-5 min when the temperature reaches 50°C. In 15-25 min the reaction causes the temperature of the solution to reach 70-75°C. The absorption of the rapid stream of butadiene is nearly complete in 30-40 min. The addition of butadiene is continued at a slower rate for a total of 2\ hr. The solution is poured into a 1-liter beaker which is covered and kept at 0-5°C overnight. The product is collected on a large Buchner funnel and washed with 250 ml of b.p. 35-60°C petroleum ether. A second crop is obtained by diluting the filtrate with an additional 250 ml of petroleum ether. Both crops are dried to constant weight in an oven at 70-80°C to yield 281.5-294.5 gm (96- 97%, m.p. 99-102°C). Recrystallization from ligroin or ether raises the melting point to 103-104°C.
Synthesis Reference(s)
Journal of the American Chemical Society, 64, p. 802, 1942 DOI: 10.1021/ja01256a018

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