Look to bmim series of ionic liquids

Thank you, Rui, but ILs are often toxic and non-biodegradable...not so "green" therefore. Any other sugestions?

Dear Juan Casado,

Amphophobic material my be one option.

It dependes on your scale! I would say [bmim]Ntf2 would be both water and oil insoluble, and as far as you can recycle and re-use it, the process is considered safe and green (please notice the properties of RTILs).

Of course, I may advice you fluorinated solvents, but it seems to me more problematic to handle.

Dear Amit,

Thank you. Any specific compound?

Dear Juan Casado,

Please check resent articles I have read one article in RSC journal on Amphophobic materials. Please go through the recent article you will definitely find the compound.

Dear Juan Casado,

This article may help you,Binary cooperative complementary nanoscale interfacial materials by L. Jiang, R. Wang, B. Yang, T. J. Li, D. A. Trigk, A. Fujishima, K.Hashimoto, D. B. Zhu, Pure Appl. Chem. 2000, 72, 73.

Regards,

Amit

[emim]NTf2, or 1-ethyl-3-methylimidazolium bistriflimide was pretty handy. Nice three-phase systems with water and pentane or ether (IIRC). It did dissolve in CH2Cl2, though. And, nonbiodegradability is highly likely for any compound that doesn't dissolve in anything. Toxicity is common for [Rmim]s, but not all cations are that toxic - you could try to invent a new one.

Also, mercury, gallium and molten phosphorus, but I don't think you're after these.

http://dx.doi.org/10.1039/C3RA41529E

Dear Amit, Thank you for your effort but the article you cited deals with solid materials, while I am looking for a liquid solvent...Could you please provide the reference for "one article in RSC journal on Amphophobic materials" that you mention?

Thank you Lauri, but (as you acknowledge) toxicity and nonbiodegradability of the compound you mention are problems that preclude its use.

Dear Juan,

During our search for solvents derived from glycerol, we found some fluorinated derivatives that are simultaneously immiscible with water and with hydrocarbons, much like some ionic liquids (Green Chem. 2010, 12, 426). I would not dare to claim that they are the greenest solvents in the World, but at least they are not heavily fluorinated (only two trifluoromethyl groups), they are barely soluble in water, and have a very low vapour pressure...

Hi Juan,

depending on the kind of oil, you can try e.g. EMIM Triflate. The compound is reach registered, so toxicity and persistency are not that bad as with the EMIM NTf2.

It also depends of course which toxicity you are concerned about, acute oral, or acute dermal, or aquatic. Please mind, that Aspirine is labeled as Toxic, and so in CetylPy Cl, which you have in your everyday cough drops,

Thank you, José. I'll read your reference with interest...

Thank you, Boyan. I am concerned with dermal toxicity, but I have the impression that Triflate would not be suitable even if its toxicity/persistency are relatively mild...

No problem, Juan, you can check the dermal toxicity of this and another 3 fully registered IL on the ECHA website. For all the others information is controversial. We have a NTf2-based IL which is proven non toxic.

Dear Juan Casado,

This review may help you.

Dear Amit, Thank you for your effort but the article you cited deals with solid materials, while I am looking for a liquid solvent...

C,N,O,H,P,S - environmentally friendly solvent should contain only this elements (organogenes). Liquid thiokol is exactly you looking for. Biodegradable, non-soluble in H2O and in oils, and contain only organogenes (C,H,S and some types - oxygen).

Thank you, Andrei, but a polysulfide does not seem very environmentally friendly, does it?

Yes, it is not food grade liquid :-)

Hazard Rating:

NFPA: Health: 0 Fire: 1 Reactivity: 0

HMIS: Health: 0 Fire: 1 Reactivity: 0

http://en.wikipedia.org/wiki/Hazardous_Materials_Identification_System

Hi Andrei, a good choice, actually, but what has to be kept in mind is, that for polymers no REACH registration is required, so no full tox tests are being performed. It is a general remark though, I do not know if full tox has been made on the thiokols.

Toxicological Properties of LP Polysulfide Polymers

Liquid polysulfide polymers are relatively non-toxic. The actual oral toxicity of LP-3 has been measured in rats as 3.5 g/kg body weight (equivalent to table salt), and other LP polymers were measured as being even less toxic orally. Eye irratationtest conducted on rabbits showed no corneal or iridialeffects, but slight conjunctivalinvolvement was found for LP-32 and LP-33. Skin irritation studied on human volunteers indicate that upon repeated 24-hour applications to the same area of skin, some individuals developed perceptible erythema evaluated as due to skin fatigue and not to sensitization. With these indivisuals, an application to another skin area, or to the same area after a rest of period, showed no reaction. It is therefore advised that prolonged or repeated contact with the skin be avoided, and protective gloves be worn as a precaution.

Please note, that this data collected for HS-terminated polymer. After appropriate end-cupping, essentially bionert polymer will formed.

Hi Andrei, as far as I know, anything above 2000mg/kg is considered acute toxic. As with all chemicals, protection and respect is required. Don´t get me wrong, I am not a fan of completely non toxic materials, if such exist at all. I have a box with Acetylsallicylic acid in the office for exactly such "all should be non toxic" fans. It has a T label and a skull. So far with non toxic. Eat 500g of NaCl at once and you will drop dead, no matter how non-toxic table salt is. It´s not the substance, but the dosage that´s toxic.

Anything "below" 2g/kg is considered acute toxic. Both dosage and toxicity are important. In some cases dosage is not critical: You can drink (not inhalate) as much water as you can and you would never die due to it...

Check perfluorinated solvents

if castor oil is yours , more options exist.

I was refering to vegetable oil, such as coconut or soybean oil

Juan, you can not drink as much water as you like. Water is toxic. The average fatal dose of pure water by drinking is 4 L for an adult human. Search the web for "water intoxication" to learn more about this problem. Fortunately, people are usually not thirsty enough to drink 4 L.

The problem with liquid thiokol is the disposal or recycling. It's incineration would cause SO2 emissions and destroy its chances of being considered green. Purifying and then reusing it would be the better option, but how much environmental impact would that cause? That's not known, but could be problematic.

For the original question, consider supercritical and liquid CO2. While CO2 will indeed dissolve in oil and, to a small extent, in water, it is extremely easy to remove. That may solve your need, depending on exactly what your application is.

Water is not toxic, since water is the basic solvent for life. The disease produced by drinking much too water, "hyponatremia" is caused by a defect of electrolytes instead of by water toxic or poisonous properties.

I was asking for a liquid solvent under standard conditions.

It is hard to discuss mix of real truth and speculation. Water is not toxic byself but desalting effect could be fatal - especially with distilled water. REHYDRON is used for compensation of intensive lost of electrolithes during diarrhea. Recommended minimal dose of water intake for my body weight is exactly FATAL 4L :-)

CO2 emission is regulated as enviroment pollutant ( it is stock-exchange ware). CO2 is solvent only by high pressure - it is immanent danger of explosion. Combustion of coal is accompanied with SO2 emission - but for some reason is not so strictly regulated.

We are not informed how Juan expect to use thiokol (it is sole suggested variant at moment). So speculation on thema of recycling is anticipatory. SO2 emission... - for what??? Many barbarian methods of disposal (in place of recycling) are known, combustion is 1st level. If you need obligatory to burn any thing that you can not reuse, note on catalytic H2O2 oxidation of wastes - it was awarded in USA long time ago by President's programm.