# D-limonene



## bombbudpuffa (Oct 9, 2008)

What is d-Limonene? 

*d-Limonene: A Cleaner from Nature 

                    d-Limonene is the major component of the oil extracted from citrus rind. When citrus fruits are juiced, the oil is pressed out of the rind. This oil is separated from the juice, and distilled to recover certain flavor and fragrance compounds. The bulk of the oil is left behind and collected. This is food grade d-Limonene. After the juicing process, the peels are conveyed to a steam extractor. This extracts more of the oil from the peel. When the steam is condensed, a layer of oil floats on the surface of the condensed water. This is technical grade d-Limonene.

*In the past decade, the use of d-Limonene has expanded tremendously. Much of the product goes into making paint solids, used to impart an orange fragrance to products, and used as a secondary cooling fluid. But the largest growth segment has been the use of d-Limonene in cleaning products. This has occurred in both industrial uses and in household/institutional products. d-Limonene can be used either as a straight solvent, or as a water dilutable product.

As a straight solvent, d-Limonene can replace a wide variety of products, including mineral spirits, methyl ethyl ketone, acetone, toluene, glycol ethers, and of course fluorinated and chlorinated organic solvents. As with most organic solvents, d-Limonene is not water soluble, so it can be used in the typical water separation units. With a KB value of 67, d-Limonene has solubility properties close to that of CFCs, indicating that it is a much better solvent than a typical mineral spirit. Straight d-Limonene can be used as a wipe cleaner, in a dip bath, or in spray systems as a direct substitute for most other organic solvents.

By combining d-Limonene with a surfactant package, a water diluting and rinsible solution can be made. In most cases these products are used in the institutional and household settings in place of caustic and other water based cleaners. A concentrated solution of a d-Limonene/surfactant solution can be made to be diluted before use, or pre-diluted solutions can be formed. The use concentrations of d-Limonene in these situations are usually 5-15%. In general these solutions are used as spray and wipe cleaners. The water dilutable solutions can also be used in industrial settings where a water rinse of the parts is desired to remove any residue which may remain.

d-Limonene is a very versatile chemical which can be used in a wide variety of applications. It is extremely safe and more effective than typical cleaning solutions.



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                    How do we get d-Limonene and Orange Oil?

        d-Limonene is the major component of the oil extracted from the citrus rind during the citrus juicing process. When the fruit is juiced, the oil is pressed out of the rind, then separated from the juice and distilled to recover certain flavor and fragrance compounds.

After the juicing process, the peels are conveyed to a steam extractor. When the steam is condensed, a layer of oil floats on the surface of the condensed water. This removes the bulk of the oil from the peel.

Food grade d-Limonene is extracted through the juicing process and Technical grade d-Limonene is removed through the peel steam extraction process. The chart below shows the citrus oil manufacturing process and the specific oils that come from each part of the process.

hxxp://www.floridachemical.com/whatisd-limonene.htm





My question is can this be used or applied in a way that would benefit taste and smell of mj(food grade, of course)?


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## bombbudpuffa (Oct 9, 2008)

*Limonene* is a hydrocarbon, classified as a cyclic terpene. It is a colourless liquid at room temperatures with an extremely strong smell of oranges. It takes its name from the lemon, as the rind of the lemon, like other citrus fruits, contains considerable amounts of this chemical compound, which is responsible for much of their smell. Limonene is a chiral molecule, and as is common with such forms, biological sources produce one enantiomer: the principal industrial source, citrus fruit, contains D-limonene ((+)-limonene), which is the (_R_)-enantiomer (CAS number 5989-27-5, EINECS number 227-813-5). Racemic limonene is known as dipentene.[1]

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*[edit] Biosynthesis*

 Limonene is formed from geranyl pyrophosphate, via cyclisation of a neryl carbocation or its equivalent as shown.[2] The final step involves loss of a proton from the cation to form the alkene.





*[edit] Uses*

 The major use of D-limonene is as a precursor to carvone.[3]
 Limonene is common in cosmetic products. As the main odor constituent of citrus (plant family Rutaceae), D-limonene is used in food manufacturing and some medicines, e.g., bitter alkaloids, as a flavoring; it is also used as botanical insecticide[4]. It is added to cleaning products such as hand cleansers to give a lemon-orange fragrance. See: orange oil. In contrast, L-limonene has a piney, turpentine-like odor.
 Limonene is increasingly being used as a solvent for cleaning purposes, such as the removal of oil from machine parts, as it is produced from a renewable source (citrus oil, as a byproduct of orange juice manufacture). It also serves as a paint stripper when applied to painted wood.
 As it is combustible, limonene has also been considered as a biofuel.[5]

*[edit] Chemistry*

 Limonene is a relatively stable terpene, which can be distilled without decomposition, although at elevated temperatures it cracks to form isoprene.[6] It oxidises easily in moist air to carveol and carvone.[7] Dehydration with sulfur gives to _p_-cymene, hydrogen sulfide, as well as some sulfides.
 Limonene occurs naturally as the (_R_)-enantiomer, but racemises to dipentene at 300 °C. When warmed with mineral acid, limonene isomerizes to the conjugated diene &#945;-terpinene, which can itself easily be oxidised to _p_-cymene, an aromatic hydrocarbon. Evidence for this isomerization includes the formation of Diels-Alder &#945;-terpinene adducts when limonene is heated with maleic anhydride.
 It is possible to effect reaction at one of the double bonds selectively. Anhydrous hydrogen chloride reacts preferentially at the disubstituted alkene, whereas epoxidation with MCPBA occurs at the trisubstituted alkene. In both cases the second C=C double bond can be made to react if desired.
 In another synthetic method Markovnikov addition of trifluoroacetic acid followed by hydrolysis of the acetate gives terpineol.
 The most widely practiced conversion of limonene is to carvone. The three step reaction begins with the regioselective addition of nitrosyl chloride across the trisubstituted double bond. This species is then converted to the oxime with base, and the hydroxylamine is removed to give the ketone-containing carvone.[3]

*[edit] Safety*

 Limonene and its oxidation products are skin and respiratory irritants, and limonene-1,2-oxide (formed by aerial oxidation) is a known skin sensitizer. Most reported cases of irritation have involved long-term industrial exposure to the pure compound, _e.g._ during degreasing or the preparation of paints. However a study of patients presenting dermatitis showed that 3% were sensitized to limonene.[8]
 Although once thought to cause renal cancer in rats, limonene now is considered by some researchers to be a significant chemopreventive agent[9] with potential value as a dietary anti-cancer tool in humans.[10] There is no evidence for carcinogenicity or genotoxicity in humans. The IARC classifies D-limonene under Class 3: _not classifiable as to its carcinogenicity to humans_.[8]
 No information is available on the health effects of inhalation exposure to d-limonene in humans, and no long-term inhalation studies have been conducted in laboratory animals.


hxxp://en.wikipedia.org/wiki/D-limonene


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## born2killspam (Nov 12, 2008)

One thing to consider if you mean you want to add it to bud directly is the fact that it is obviously a non polar solvent..  Your cannabinoids would dissolve, and would be pretty much forever locked up with the limonene..  Personally I can't think of a worse flavor addition, and most compound's flavor/odour can change drastically by varying the concentration.. (Apologies if that doesn't apply here, I didn't look into it)  For instance, the compound indole is responsible for the odour of feces, and also the smell of roses..  (After I learned that I really started to wonder about the origin of the expression "Your S#!t don't smell like roses"..) 
If its such a common compound in nature then its probably already present in soil..  Whether or not the plant or mychorhizae can actually uptake it and put it to good use I don't have a clue, but I highly doubt it would wind up in the finished product any more than normal..


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## papabeach1 (Nov 13, 2008)

is that related to orange?  maybe iso on the dried orange peels? 

this is getting interesting.. man  did you go to school?    its like orange oil. hmm?


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