US Pat 3806548 1-Phenyl-1-Propanol From Styrene , Hive Chemistry Discourse
2
20/1/2014 US pat 3806548 1-phenyl-1-propanol from styrene , Hive Chemistry Discourse http://chemistry.mdma.ch/hiveboard/chemistrydiscourse/000481881.html#Post481881 1/2 Aurelius (Active Asperger Archivist) 01- 11- 04 22:34 No 481881 US pat 3806548 1-phenyl-1-propanol from styrene (Rated as: good read) 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. Act quickly or not at all. wareami How interesting?
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Transcript of US Pat 3806548 1-Phenyl-1-Propanol From Styrene , Hive Chemistry Discourse
20/1/2014 US pat 3806548 1-phenyl-1-propanol from styrene , Hive Chemistry Discourse
http://chemistry.mdma.ch/hiveboard/chemistrydiscourse/000481881.html#Post481881 1/2
Aurelius(Active
AspergerArchivist)01-11-04
22:34No
481881
US pat 3806548 1-phenyl-1-propanol from styrene(Rated as: good read)
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 UnsaturatedCompounds
Abstract: Certain aromatic compounds having an unsaturated chain, such asstyrene or derivatives thereof, are reacted with peracetic acid or mixtures containingperacetic acid to add the elements of a methyl radical and a hydroxyl radical to theunsaturated chain. For example, styrene can be converted to 1-phenyl-1-propanoland propiophenone.
Example 1:
A 500ml flask was equipped with a reflux condensor, thermometer, magnetic stirringbar and two addition funnels. There were added to the flask 300ml of benzene and10.2g of acetic anhydride and the solution was heated to the reflux temperature of83*C while stirring and continuously purging with nitrogen. Simultaneously, 125g of a24.2% solution of 10.4g of styrene in 40 ml of benzene were added to the flask overa 65minutes period at the reflux temperature of the contents. The reaction mix wasstirred for an additional hour at reflux and cooled. GLC showed the pale yellowsolution with tridecane as the internal standard was styrene converted to 30% 1-phenyl-1-propanol, 12.3% propiophenone and 28% styrene oxide. The compoundsare separable by conventional separation procedures after destroying unreactedperacids with an acetaldehyde.
Example 3:
A quartz reaction vessel containing a 450 watt Hanovia Hg ultraviolet lamp in a wellsurrounded by a cold water jacket was charged with 300ml of ethyl acetate. Whilebubbling 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*Cover a 40-minute period while irradiating the mixture with ultraviolet light. Theirradiating was continued for another 1.5 hours after the addition was complete andthe reaction mixture of these three products, the 1-phenyl-1-propanol was presentas 48.7% thereof, the propiophenone as 27% thereof and the styrene oxide as only24.3% thereof.
It was also found that the use of a solution of acetyl peroxide and acetic acid inethyl acetate does not convert styrene to 1-phenyl-1-propanol or propiophenone atreaction conditions of 100*C for about one hour; this indicates that the presence ofperacetic acid is necessary.
Only the most relevant information was included in this post.
Act quickly or not at all.
wareami How interesting?
20/1/2014 US pat 3806548 1-phenyl-1-propanol from styrene , Hive Chemistry Discourse
http://chemistry.mdma.ch/hiveboard/chemistrydiscourse/000481881.html#Post481881 2/2
(HiveAddict)
01-11-0422:52
No481884
Aurelius: Ibee's been researching the newest gaaks on the market, Orange I and IIgaaks and thinks that they may be of the Star polymer family.Star-shaped PolymersThe star-shaped structure of such macromolecules is responsible for theirextraordinary physical properties. Their unusual topology gave rise to therecent interest of polymer research workers. Star-shaped polymers areavailable with three arms consisting of styrene or isoprene. More arms orother monomers are possible but need much more effort to yield well definedstructures and high product purity.
The most interesting notes that were compared early on when doing physicalresearch on the OTC's in question was the strange similarity in crystal structure ofthe Gaak with that of Meth.I think we are narrowing down our search for this gaaks identity....Glad you posted this!Thanx
Peace of the RXN
Have FUN-Bee SAFE
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