Allyl Orthoborate --> Allylbenzene

[Bwiti]

Check-out this example I found in GB787615(

http://l2.espacenet.com/espacenet/viewer?PN=GB787615&CY=gb&LG=en&DB=EPD

):

"EXAMPLE I
Into a stirred mixture of 2340 parts of anhydrous benzene and 162 parts of pulverised anhydrous ferric chloride are introduced, in 40 minutes and while the temperature is maintained between 25 and 35"C.

303 parts of allyl orthoborate. The mixture is then heated for one hour at 70or. The mass is cooled and filtered and the hydrocarbon layer is washed with 2,000 parts of water. It is decanted and thereafter dried over sodium sulphate. On distillation, 209 parts of allyl benzene are obtained, boiling point 155 - 156 C./740 mm. Hg. refractive index (n20) 1.5105."

Love my country, fear my government.

[alchemy_bee]

What does this Allyl Orthoborate look like? i cannot find it on chemfinder.
A nut for a jar of tuna.
-The drive by palindromer

[Rhodium]

B-O-CH2-CH2=CH2

Like this but with two more allyloxy on the boron atom.

[Aurelius]

does anybody have a synthesis for allylorthoborate?  getting ready to do some searching.

[alchemy_bee]

is this an industrial material or somthing that could be purchased? does it have a cas number?
A nut for a jar of tuna.
-The drive by palindromer

[Rhodium]

If I'm not mistaken, BR3 is prepared from B(OR)3 + RMgBr

[Aurelius]

allylbenzene patent thread now started, so here's aurelius' contributions.

gb787615
us3678122  (benzene, CuCl2, allylhalide)

[alchemy_bee]

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000329237-file_pn0w.gif" title="View this image">

Boron allyloxide/ triallyl borate, CAS 1693-71-6
A nut for a jar of tuna.
-The drive by palindromer

[Aurelius]

aurelius read the us patent, higher pressures (30-150atm) needed for the rxn.  however, they didn't state (in what aurelius had time to read) that the pressure was necessary, however, if a person were to attempt the reaction at 1atm, at least a inert atmosphere would be in order.

[Bwiti]

"does anybody have a synthesis for allylorthoborate?"

  How about this?

http://l2.espacenet.com/espacenet/viewer?PN=US3853941&CY=gb&LG=en&DB=EPD

 
Love my country, fear my government.

[Osmium]

B(OR)3 can be made from boric acid/borates and ROH with H2SO4 catalysis.

Here's a nice little party trick for you:
add some Boric acid or Na borate to MeOH, squirt in some H2SO4 and light it. It will burn with a green flame, very impressive when done in the dark.
I'm not fat just horizontally disproportionate.

[Aurelius]

What is it that's causing the coloration?  (excitation of boron?)

[Osmium]

Volatile boron compounds burn with a green flame.

Someone once asked me how to produce such colored flames since he paid lots of money for ready-made stuff and that's how I found it. First I tried barium salts and strontium for red flames until I found out that boron esters produce green and red is best made with Li salts.
I'm not fat just horizontally disproportionate.

[hest]

Yes, Li metal disolved in methanol gives a great pink collor (and the smoke take's the depresion   ).
But how do you split the azeotrop of boron ester and methanol (30% boron acid methyl ester)

[Osmium]

You don't. It only takes a little volatile boron compound to colour a flame.
The triethylester is commercially available and not very expensive, so I guess EtOH doesn't form an azeotrope.
I'm not fat just horizontally disproportionate.

[Aurelius]

http://www.callery.com/pdf/bulletin/amine_borane_bulletin_4-24-02.pdf

pg 7-8 show the formation of trialkylborates from amine boranes and alcohols (such as allyl alcohol)

pg 17 shows the reduction of carbonyls to alkanes