so having issues with an extraction at the moment on some acacia longifolia flowers:

.I soaked an unknown amount of flowers (didn't measure sorry) in methylated spirits for a few days until the flowers had lost all their yellow colour. the metho ended up a lime green colour.

. the metho was strained until completely transperant

. 20g NaOH was added to 100ml warm water. the solution was left until it went clear and then added to the metho solution. instantly the solution clouded with brilliant orange precipitation. the precipitates sat on top until the solution was agitated and then dissolved. the whole solution ended up a light orange colour

so the issue lies in the next step as I am unsure what is going on - I added about 80ml toluene to the solution. there was no distinct layer seen, even before being mixed... like adding water to water. it just seemed to become one solution. now I assume this had something to do with using a dominantly ethanol solution, but I've mixed non polar with ethanol solutions fine in the past.
the wierd thing is there is a very dark red layer of about 50ml sitting at the bottom of the flask. I thought that this may have been the toluene reacting strangely, so I separated it.. I was a bit naughty and put my finger in to see whether it felt like non polar solution or whether it was a soapy liquid (as would be with lye)... seemed the latter... and i just added some toluene again just then and no layer formed at the top. the solution cloudded up with beads of liquid suspended in the solution which eventually dissolved after agitation.. exact same thing happened with water... this has me completely stumped i've never seen anything like it. both non polar and polar area the same solution... and theres a wierd dark red solution at the bottom and i dont know what that is

Any input would be appreciated here. by the way... after adding the lye to the metho solution, the floral smell became really dominant. smells beautiful!

toluene smells beautiful.

that being said, you may want to add more lye.

oh yea...and for those who think toluene is miscible with methanol...wrong.
it is not. DCM and chloroform are.

look at a solvent miscibility chart, and look at toluene's structure. there are no hydrogens which participate in hydrogen-bonding interactions, because the structure is completely VDW interacting. polarity in toluene is only due to pi-bond conjugation, and it is intramolecular.

you may have an emulsion. increase the polarity of the aqueous phase by adding more lye or salt; also consider heating the solution in a hot water bath, ~ 80C.

Benzyme,

In our local version of English here in Australia "metho" refers to methylated or denatured ethanol and not methanol.

if methanol was added to the ethanol, the chemistry still applies.
if pyridine was added, that may be the problem.

i'm fairly certain its not an emulsion... there are absolutely no globules of liquid suspended in the solution... it is completely clear liquid so if it was emulsified I'd think you'd be able to see it... when agitated now, it looks almost like gas or something.. similar to when HCL is added to water. if it was an emulsion you'd at least see some sort of layer/separation.. there is no distinction between either the toluene or the methylated spirits. it is like adding water to water.. I am stumped as to what the deep red layer at the bottom may be too... its not toluene as I've added more to the solution to see if it increases the volume of the red layer.. nothing

my guess is there is something in the methylated spirits that makes it miscible with toluene
pic below..

that bottom layer looks like a basified aqueous layer.
separate it, and check the pH.

^..does look like a separation..

make sure that any methanol/ethanol is mixed with a portion (say 10%) of highly basic water to make it separate from the NP solvent..

Definitely looks like you have separation in that flask.

You could try and evap the top layer under a fan and see what it gives up.

as I said I added 100mls of water with 20g NaOH to the solution... and I have added another 30g dissolved in water since then.. still no non polar layer at the top. I think benz is right in saying that the bottom layer could be basic aqeous solution... but why would that not be miscible with the methylated spirits? I also tried adding shellite in and it is miscible too

and yeah VitalStatistix... there is separation, but it is between two polar liquids strangely enough. the lighter coloured solution ontop of the small amount of red basic liquid is both metho and toluene..

there was a small portion of metho at the bottom of the bottle I bought so I added an equal volume of toluene to it to see if it would behave differently to the extraction.. definitely miscible. this is "diggers methylated spirits" by the way so looks like that is one to avoid.

adding an equivalent volume of H2O to your solution should knock the toluene out of solution.