US pat 3806548 1-phenyl-1-propanol from styrene

[Aurelius]

This patent was referenced in this post:

Post 295011

(foxy2: "1-phenyl-1-propanol synthesis", Chemistry Discourse)

US Patent 3806548

Method for the Methylation-Hydroxylation of Certain Aromatic Unsaturated Compounds

Abstract:  Certain aromatic compounds having an unsaturated chain, such as styrene or derivatives thereof, are reacted with peracetic acid or mixtures containing peracetic acid to add the elements of a methyl radical and a hydroxyl radical to the unsaturated chain.  For example, styrene can be converted to 1-phenyl-1-propanol and propiophenone.

Example 1:

A 500ml flask was equipped with a reflux condensor, thermometer, magnetic stirring bar and two addition funnels.  There were added to the flask 300ml of benzene and 10.2g of acetic anhydride and the solution was heated to the reflux temperature of 83*C while stirring and continuously purging with nitrogen.  Simultaneously, 125g of a 24.2% solution of 10.4g of styrene in 40 ml of benzene were added to the flask over a 65minutes period at the reflux temperature of the contents.  The reaction mix was stirred for an additional hour at reflux and cooled.  GLC showed the pale yellow solution with tridecane as the internal standard was styrene converted to 30% 1-phenyl-1-propanol, 12.3% propiophenone and 28% styrene oxide.  The compounds are separable by conventional separation procedures after destroying unreacted peracids with an acetaldehyde.

Example 3:

A quartz reaction vessel containing a 450 watt Hanovia Hg ultraviolet lamp in a well surrounded by a cold water jacket was charged with 300ml of ethyl acetate.  While bubbling nitrogen through the ethyl acetate, 10.4g of styrene and 100g of a 25% solution of peracetic acid in ethyl acetate were simultaneously added at about 20*C over a 40-minute period while irradiating the mixture with ultraviolet light.  The irradiating was continued for another 1.5 hours after the addition was complete and the reaction mixture of these three products, the 1-phenyl-1-propanol was present as 48.7% thereof, the propiophenone as 27% thereof and the styrene oxide as only 24.3% thereof.

It was also found that the use of a solution of acetyl peroxide and acetic acid in ethyl acetate does not convert styrene to 1-phenyl-1-propanol or propiophenone at reaction conditions of 100*C for about one hour; this indicates that the presence of peracetic acid is necessary.

Only the most relevant information was included in this post.

[wareami]

Aurelius: Ibee's been researching the newest gaaks on the market, Orange I and II gaaks and thinks that they may be of the Star polymer family.
Star-shaped Polymers
The star-shaped structure of such macromolecules is responsible for their extraordinary physical properties. Their unusual topology gave rise to the recent interest of polymer research workers. Star-shaped polymers are available with three arms consisting of styrene or isoprene. More arms or other monomers are possible but need much more effort to yield well defined structures and high product purity.

The most interesting notes that were compared early on when doing physical research on the OTC's in question was the strange similarity in crystal structure of the Gaak with that of Meth.
I think we are narrowing down our search for this gaaks identity....
Glad you posted this!
Thanx