I was tossing Water Soluble Chlorophyll Binding Protein on the table as the possible elusive water soluble substance binding the chlorophyll in the plants and allowing water washing to exhibit some of the properties it does.
They are proteins that are soluble in water, have some solubility in alcohol, and are insoluble in non polar solvents.
Broken loose, the chlorophyll could form micelle, by clumping with their polar ends out and their hydrophobic tails in, which would allow them to be transported by the water.
Freezing would make them less available to the water, and with them in place, the chlorophyll would be protected from the alcohol.
What that doesn't explain, is the light green hue BHO picks up without the presence of alcohol.
That brings us to the definition of insoluble, which gets lightly tossed about as an absolute, when in fact it is a relative term. The alkane butane, considered insoluble in water, is not totally and will hold up to 32ml/L water.
Since there are no simple oxygenated alkane alcohols present, what is responsible for extracting the green?
I submit that polar chlorophyll is also slightly miscible with polar water, because it has both polar hydrophilic surfaces and hydrophobic surfaces.
Unfortunately, these articles are not readily available to my understanding. My familiarity with the anatomy of the cell is limited only by -
I was interested in the location of the chlorophyll in the cell when suddenly got an emerald-green butane extract, washed from dry sepals peeled from fem seeds.
Green puzzled me, because the chlorophyll does not dissolve in nonpolar butane.
Then I decided that this strange behavior of chlorophyll depends on how the grains of chlorophyll are attached to the tissues of plants.
If they are held by some grease or wax, which are soluble in butane, after the dissolution of these compounds are released and the chlorophyll grains fill butane solution in a suspended state, but not dissolved.
With the naked eye, we cannot distinguish individual objects smaller than 50 microns and visually perceive suspension as a solution. Chl grains are 2-10 microns.
But even in these articles they write that the membranes are hydrophobic and water-soluble proteins are rare.
All chlorophyll (Chl)-binding proteins involved in photosynthesis of higher plants are hydrophobic membrane proteins integrated into the thylakoids. However, a different category of Chl-binding proteins, the so-called water-soluble Chl proteins (WSCPs), was found in members of the Brassicaceae, Polygonaceae, Chenopodiaceae, and Amaranthaceae families.
I used this polar->nonpolar gateway, transferring the desired resin from the green solution in ethanol to non-polar petroleum ether, it was the British lighter fluid "Newport."
The procedure was carried out in several stages.
I added small portions of petroleum ether, shaking vigorously, waiting for the separation of layers, took a yellowed layer of ether with a syringe and added a fresh portion instead of removed.
Of course, each successive portion was painted paler than the previous one.
Only in the last step I added water. Without water, the layers are separated much faster and a very inconvenient boundary layer of emulsion does not form.
Have you tried using saturated brine, instead of plain water?
Chlorophyll, as it is insoluble in a nonpolar solvent, always remains in alcohol and after adding water, chlorophyll remains in alcohol, diluted with water, but not in water.
In my opinion, this ancient technology from the era before the butane in no way indicates the solubility of chlorophyll in the water.
Unfortunately Water cannot wash away Chlorophyll.