limonene as np solvent?

[elfspice]

[sYnThOmAtIc]

Umm, forget about the search engine?

Post 174723 (missing)

(sYnThOmAtIc: "!d-Limonene!", Chemicals & Equipment)

[Rhodium]

Post 443189 (missing)

(Rhodium: "Limonene / Turpentine / Pinene", Stimulants)

Post 479893

(Rhodium: "Not good", Chemicals & Equipment)

The double bonds in limonene may react with acids/bases and your product, depending on the conditions used.

[elfspice]

I also noticed there's a commonly available (at least in the antipodes) plant oil, an ether, called eucalyptol the major component of eucalyptus oil (it's also called 1,8 cineole). This one caught my eye because of it's state transition temperatures, mp 1-2°C bp 90-91°C. It is also completely saturated.

I wish i'd spotted this one first before posting about limonene again... rats

I think my money is on this oil as a viable alternative natural solvent. It would even be servicable for evaporating freebases directly, some oiling out would occur but that's a small price to pay considering how safe this solvent is

Rhodium: the purposes i had in mind were mostly about extracting alkaloids from plants.


here's some interesting info:

Oil of Eucalyptus  80/85  Eucalyptus globulous China. High natural eucalyptol content. Used commercially in muscle rubs and decongetion aids. Repels insect pests. Antiseptic. Good solvent for removing adhesives.

(my emphasis)

eucalyptus oil can be had for around 20/L in quantities 1L or more and the oil is 80% eucalyptol, which boils at about 90-91 degrees.

I can't see any reason why it would fail as a substitute for xylene, naptha or toluene in acid/base extractions.


just a little, maybe silly idea - what about if one distilled limonene and hydrogenated it... then it would become p-methyl isopropyl cyclohexane (to be precise: cis-1-Methyl-4-isopropylcyclohexane  [6069-98-3]
Synonyms: CIS-1-ISOPROPYL-4-METHYLCYCLOHEXANE; cis-1-Methyl-4-isopropylcyclohexane; )

ooh it has a geometric isomer too...

I can't get any phase change data on it or anything much at all. One would assume it would be vaguely similar to a cyclohexane but heavier. Probably not economic, but might be a way to make use of limonene.


heh i bet one can turn limonene into cineole too considering the locatin of both of those unsaturated carbon bonds, if there's some way to oxidise it to the ether.

plant oils will yet replace synthetics dammit!

[elfspice]

just thinking while chatting to a friend in irc and he said 'what about substituting it for ether' and i thought 'well... it is an ether...' should be possible to use in place of ether in at least some reactions

[elfspice]

grrr

here's what i've found for phase change data of 1,8 cineole (CAS 470-82-6):

http://www.thegoodscentscompany.com/data/rw1056361.html

Melting Point :    1.00 - 2.00 °C. @ 760.00 mm
Boiling Point :   176.00 - 177.00 °C. @ 760.00 mm
Boiling Point :   90.00 - 91.00 °C. @ 760.00 mm

confusing?

chemfinder returns this info:

mp 35.6 (presumably at 760mm)
bp 351 at 0 mm

oh really?

let's see if we can find another different result

http://www.chemicalland21.com/arokorhi/specialtychem/perchem/OIL%20OF%20EUCALYPTUS.htm

MELTING POINT

BOILING POINT    175 C


AAAAAAAAAHHHH! eureka!

Here we are! this is the gold i've been prospecting for. This document shows that 1,8 cineole has great potential as a solvent, and some solid physical properties data  - liquid phase from 0 to 176, steam distillable, cineol is relatively unreactive and appears to be functionally similar to a most other aliphatic hydrocarbons (looking at it's polymer solvation activity).

I think we have a winner for a generally useful substitute for xylene that is also very benign biologically and environmentally.

http://www.oilmallee.com.au/docs/BARTON.doc

Industrial Uses of Eucalyptus Oil

A/Prof Allan Barton
Division of Science and Engineering - Chemistry, Murdoch University, Murdoch 6150.
Email barton@chem.murdoch.edu.au. Tel (08) 9360 2132 Fax (08) 9310 1711

Summary

The large-scale planting of Eucalyptus oil mallees to rehabilitate water-logged and salt-affected agricultural land will permit the use of high-cineole leaf oils to replace environmentally unacceptable industrial solvents such as the ozone-depleting trichloroethane.  At the same time this process will provide a renewable fuel biomass and a carbon sequestration mechanism.

....

space limitations prevent me putting more, but there it is.

[foxy2]

I can't see any reason why it would fail as a substitute for xylene, naptha or toluene in acid/base extractions.

Maybee for this reason --> 20/L

[elfspice]

Well, the cost is high, but I think there's probably good reason to suspect it will go down in price as it becomes more adopted, already blends of limonene and cineole are being sold as degreasers. Australia has plenty of land that is arable enough for oil mallee to be grown on it...

Also, if anybee has bought xylene in a 1L container they probably paid near or over $20 for it, certainly that's what they charge around here for it. so for small quantities, no big deal. And remember you aren't going to cause yourself brain damage or respiratory problems using it...