Eugenols

How then would you make eugenol (TM 320), a constituent of oil of cloves ... 

Strike wrote the above paragraph relying on the few accounts of sassafras oil content that Strike had at the time. Since then. Strike has come across more substantial data showing that Brazilian sassafras has NO eugenol in it. This agrees with the claims of many bees who have stated that no appreciable recovery of... 

If one is absolutely serious about ultra pure safrole then it can be separated from the eugenol-free sassafras oil by treatment with mercuric acetate [1,2,3,4] which likes that terminal double bond that only safrole has. The Hg(AcO)2 latches on to safrole at that double bond bringing it into solution as a solid sort of like the way that eugenol was. The safrole can then be separated from its still oily buddies by vacuum filtration. Safrole is then regenerated to its normal oily form by treatment with hydrochloric acid (HCI) which flicks the Hg(AcO)2 off the safrole and the safrole double bond reforms. As it so happens, the mercuric acetate also reforms intact so that it can be reused again such as in one of those... 

Using 28% acetic acid allows the eugenol, d-camphor and pinene to form its own top layer. There ivas no separation using 99.5% acetic acid. 

Added 112 grams sassafras oil. Shake for a couple of minutes. You get an orangish emulsion. Clears within 15 minutes forming two layers, bottom layer oil, top layer acetic acid, eugenol + the other solubles. Separated the oil from the others, washed the oil layer 2x with fresh C//-/2O. Weight after acetic acid water washes 101.5 (-10.5 grams). 

Added 100 grams denatured alcohol, no layer formed as the oily product is miscible in ethanol. Added 20 grams of C//-/2O. This pulled the ethanol and other product into the top layer, bottom layer containing some ethanol and safrole. Separated layers, placed the oily bottom layer into a 2-liter breaker. Took the temp right to 234 C. The ethanol and water came off <=100 C... The safrole started to boil 232C, then came to a full boll and maintained 234 C. Product ui/as yellow orange in color, suitable for whatever purpose one has in mind BTW, after the safrole cooled, she checked it with a 5% NaOH solution to see if any eugenol ivas left behind, no participate formed. 

GENERAL PROCEDURE The Alcoholic alkaline solution is prepared by prolonged stirring of 8.8g (or 4.4g) of KOH pellets in 30mL of alcohol. The alkaline solution is placed in a round-bottom flask provided with a reflux condenser (microwave or conventional systems). Then 4.0g of Safrole (or eugenol) is added and the solution heated."... 

EUGENOL In very large amounts in bay, cinnamon, clove and pimento oils. In goodly amounts in basil, eucalyptus and tejpat. Lots of trace amounts in many other oils. 

A much more forgiving yet limited extraction method can be used to isolate phenol species such as eugenol and chavicol. You see farther back in this chapter where one can use dilute NaOH to remove eugenol from sassafras oil Well, why not use it to isolate the damn things for further research. It works like a charm ... 

Zinc oxide beds Zinc oxide eugenol Zinc oxides Zinc-oxygen cell... 

Zeylanicum. The second type of cinnamon is the dried inner bark of the shoots of the tree Cinnamonium lanicum Nees, a moderately sized coppiced evergreen bush of the laurel family cultivated in Sri Lanka. The bark is stripped, roUed into quills, dried, and then shipped in large bundles. The aroma and flavor of the lanicum type, which contains eugenol as well as cinnamic aldehyde, is much milder than the cassia type. 

Antioxidants. Widely used antioxidants are eugenol, ionol, and the like. They retard premature oxidation of inks on the press rollers when used at low concentrations. 

A number of other valuable aroma chemicals can be isolated from essential oils, eg, eugenol from clove leaf oil, which can also, on treatment with strong caustic, be isomerked to isoeugenol, which on further chemical treatment can be converted to vanillin (qv). Sometimes the naturally occurring component does not requke prior isolation or concentration, as in the case of cinnamaldehyde in cassia oil which, on dkect treatment of the oil by a retro-aldol reaction, yields natural ben2aldehyde (qv). This product is purified by physical means. 

Other commonly occurring chemical groups ia essential oils iaclude aromatics such as P-phenethyl alcohol, eugenol, vanillin, ben2aldehyde, cinnamaldehyde, etc heterocycHcs such as iadole (qv), pyra2iaes, thia2oles, etc hydrocarbons (Liaear, branched, saturated, or unsaturated) oxygenated compounds such as alcohols, acids, aldehydes, ketones, ethers and macrocyclic compounds such as the macrocyclic musks, which can be both saturated and unsaturated. 

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