2-(4-tert-Butylbenzyl)propionaldehyd Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R38:Reizt die Haut.
R51/53:Giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
S-Sätze Betriebsanweisung:
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
Chemische Eigenschaften
Lily aldehyde is a homolog of
cyclamenaldehyde. The racemic compound is a colorless to slightly yellow liquid
with a mild-floral odor, reminiscent of cyclamen and lily of the valley.
The aldehyde is prepared by the same routes as cyclamenaldehyde.
Other routes start from -methylcinnamaldehyde. -Methylcinnamaldehyde
(from benzaldehyde and propionaldehyde) is hydrogenated to -methyldihydrocinnamic
alcohol.The alcohol is alkylated with tert-butyl chloride or isobutene to
4-tert-butyl--methyldihydrocinnamic alcohol, which is subsequently dehydrogenated to the desired aldehyde.
4-tert-Butyl--methyldihydrocinnamaldehyde is more stable than cyclamenaldehyde
and is a popular component of flower compositions, particularly lily of the
valley and linden types, because of its mild, pleasant, blossomfragrance. It is used
in a wide range of perfume types, but especially in soap and detergent perfumes.
Verwenden
In addition to its applications in the perfume and aroma industry, lilial is used mainly for the synthesis of substituted 3-(4-tert-butylphenyl)-2-methylpropylamines, a new class of substances with fungicidal properties. These compounds are effective against mildew in barley and wheat.
Vorbereitung Methode
Lily aldehyde is produced industrially almost solely by aldol condensation of 4-tert-butylbenzaldehyde and propionaldehyde to give 4-tert-butyl-α-methylcinnamaldehyde, which can be hydrogenated selectively on noble metal catalysts such as Pd, Rh, Pd – Pr2O3 on Al2O3, or on modified cobalt catalysts. The aldol condensation and the hydrogenation can be carried out in one step in the presence of a hydrogenation catalyst.
The Friedel – Crafts reaction of 4-tertbutylbenzene with methacrolein or methacrolein diacetate proceeds in an analogous manner to the preparation of cyclamenaldehyde.
Further possibilities are the Rh-catalyzed hydroformylation of 1-(4-tert-butylphenyl)-1- methoxypropene and subsequent partial hydrogenation, the palladium salt catalyzed reaction of 4-tert-butylphenylhalide with methallylalcohol, and the dehydrogenation of 3-(4-tert-butylphenyl)-2-methylpropanol on silver catalysts.
Allgemeine Beschreibung
2-(4-
tert-Butylbenzyl)propionaldehyde is categorized under the synthetic fragrance class of compounds widely utilized in consumer products such as perfumes, after shave lotions, cosmetics, etc.
Handelsname
Lilestralis Pure (Innospec), Lysmeral® Extra (BASF).
Kontakt-Allergie
Lilial is a synthetic compound listed as a fragrance
allergen. Its presence is indicated on cosmetics within
the EU.
2-(4-tert-Butylbenzyl)propionaldehyd Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
