Heptane from a plant source, for the extraction of natural products

Abstract

A heptane composition obtained from a plant source is described, wherein the plant source comprises Commiphora wildii and wherein the heptane composition is obtained by a process of extraction comprising hydrodistilling or steam distilling a resin of Commiphora wildii to obtain an essential oil. A method of using the heptane composition as a solvent for extracting one or more natural products is also described.

Claims

1. A heptane composition obtained from a plant source, wherein the plant source comprises Commiphora wildii, wherein the heptane composition is prepared by a process of extraction comprising hydrodistilling or steam distilling a resin of Commiphora wildii to obtain an essential oil, wherein the process further comprises physically purifying the heptane composition by fractional distillation or by molecular distillation; and wherein the purified heptane composition comprises at least 99.3% heptane, 0.3% alpha-pinene, and 0.1% beta-pinene.

2. The heptane composition as claimed in claim 1, wherein a content of linear isomer n-heptane is above 99.0%.

3. The heptane composition as claimed in claim 1, wherein the essential oil is obtained in an amount of about 5.5% based on a fresh weight of resin.

4. The heptane composition as claimed in claim 1, wherein the process further comprises collecting resin from plants of a cultivated type or wild type.

5. The heptane composition as claimed in claim 1, wherein the process further comprises collecting resin from a whole plant.

6. A method of using the heptane composition as claimed in claim 1, the method comprising extracting one or more natural products from a second plant source with the heptane composition of claim 1 as a solvent.

7. The method as claimed in claim 6, wherein the natural product comprises rose, jasmine, lily, violet, mimosa, tuberose or any other plant useful in perfumery, cosmetics and food flavoring.

Description

DETAILED DESCRIPTION

(1) In the following detailed description of the embodiments of the present disclosure, many specific details are disclosed in order to provide a deeper understanding of the present description. However, it will be apparent to a person skilled in the art that the present description can be implemented without these specific details. In other cases, well-known features have not been described in detail, to avoid needlessly complicating the description.

(2) Hereinafter, the term “comprise” is a synonym of (means the same thing as) “include”, “contain”, and is inclusive or open and does not exclude other elements that have not been described or represented. Furthermore, in the present description, the term “substantially” is a synonym of (means the same thing as) a lower and/or upper margin of 0.05% of the respective value. The following description gives two examples of process of extraction of heptane as defined by one or more of the embodiments presented above, as well as examples of a method of using of the heptane, such as for the extraction of natural products.

Example 1 of the Process of Extraction of Heptane

(3) The process of manufacture according to Example 1 comprises hydrodistilling the resin of Commiphora wildii to obtain an essential oil, and distilling by fractional distillation of this essential oil.

(4) The resin of Commiphora wildii is a natural exudate from the tree. As the bark of this tree is very thin and the resin-secreting channels are located just underneath, it is possible to recover this resin by incision on the lower part of the trunk. When the resin flows, it is of a milky white color, and it turns red on drying. The exudate used in the example of process of manufacture detailed below was collected after some weeks, so that the resin is dry.

(5) The resin extracted from Commiphora wildii is hard and brittle, but becomes ductile and malleable when heated. The extraction technique used makes it possible to obtain a volatile extract from this resin.

(6) According to one embodiment, hydrodistilling comprises: adding water to the resin of Commiphora wildii in the form of powder or small pieces/particles in a round-bottomed vessel fixed to apparatus of the Clevenger type, heating the suspension thus obtained to boiling point and condensing the vapors to recover the essential oil/water mixture. To separate the essential oil from the water, it is sufficient to decant the mixture. The apparatus of the “Clevenger” type allows reinjecting the aromatic water, namely the aqueous phase of the distillate, in the flask to avoid water depletion of the initial mixture. This technique is called hydrodistillation with cohobation. The same type of process may be carried out with a conventional still.

(7) In the context of Example 1, the manipulation is carried out with a 20 L flask containing 2.00 kg of resin of Commiphora wildii immersed in five times its volume of water, or 10 L.

(8) A kinetic study was conducted in these conditions, in order to determine the hydrodistillation time for controlling the yield of essential oil and the proportion of heptane. Table 1 presents the yields of essential oil obtained as a function of the hydrodistillation time. Similar results are obtained using a still.

(9) TABLE-US-00001 TABLE 1 Hydrodistillation time (h) Yield of essential oil (%) 4 5.68 6 6.99 12 7.77 18 8.22

(10) The composition (in relative percentages obtained by integration of the chromatographic profile) of the essential oil obtained after 4 h of hydrodistillation was analyzed by GC/MS. The essential oil comprises: 43.4% of alpha-pinene, 29.5% of heptane, 11.0% of beta-pinene, 3.7% of alpha-thujene, and 2.3% of ortho-cymene. This new essential oil isolated by the inventors has, among others, a high heptane content.

(11) The process of manufacture in Example 1 further comprises extractive distillation of the essential oil obtained after 4 h of hydrodistillation. Starting from this essential oil, it is possible to separate a fraction at 37.8 wt %, containing predominantly heptane, at least 99.3% pure. It contains not only heptane, but also alpha-pinene and beta-pinene in minor amounts, 0.3% and 0.1% respectively.

Example 2 of the Process of Extraction of Heptane

(12) The process of manufacture according to Example 2 comprises hydrodistilling the resin of Commiphora wildii to obtain an essential oil, and fractional distilling this essential oil.

(13) The essential oil obtained after 24 h of hydrodistillation comprises alpha-pinene, heptane, beta-pinene, para-cymene, and terpinen-4-ol.

(14) The process of manufacture from Example 2 further comprises distilling by extractive distillation of the essential oil obtained after 24 h of hydrodistillation. Starting from this essential oil, it is possible to separate a fraction containing predominantly heptane, at least 90.0% pure. It contains not only heptane, but also alpha-pinene and beta-pinene.

Examples of Methods of Using the Heptane for the Extraction of Natural Products

(15) The heptane produced as indicated above in Examples 1 and 2 was used as a solvent for extracting natural products, such as for example flowers of jasmine, lily, rose, violet, mimosa, and tuberose with a view to obtaining a concrete and then an absolute, marketable in the field of perfumery, cosmetics or food flavorings.

(16) These extractions were carried out in the same conditions from one plant to another. The extracts obtained were compared with the extracts obtained from fossil heptane, derived from a petrochemical source.

(17) The concretes obtained with the heptane derived from the species Commiphora wildii as solvent make it possible to conclude that the olfactory result is different from that obtained with fossil heptane. Without wishing to be bound by any theory, this may be explained by the quality of the heptane extracted and optionally by the presence of other odorous compounds in small amounts in the heptane extracted according to one or more embodiments of the present description.

(18) A comparison of the sensory results obtained for volatile solvent extraction of three natural products, with fossil heptane versus the heptane derived from Commiphora wildii produced as indicated in Example 1, is presented in Table 2. The table shows, depending on the type of heptane used (heptane produced according to an embodiment of the present description or fossil heptane) and for each natural product extracted, the yield of concrete and the olfactory description of the absolute obtained from the concrete.

(19) TABLE-US-00002 TABLE 2 Heptane produced according to Example 1 Fossil heptane Olfactory Olfactory Yield of description of Yield of description of concrete the absolute concrete the absolute Rose 0.47% Fruity facets (banana), 0.22% Green odor, floral, (Rosa centifolia L.) floral, rose, honey. sticky and tenacious. Lily (Lilium spp) 0.41% Floral odor, stifling, 0.36% Strong odor of lily, honey, less fatty. fatty, green, watery and iodized. Jasmine 2.60% Fatty odor, flowery, 0.67% Flowery odor, (Jasminum grandiflorum L.) jasmine and menthol. sticky, fatty, animal and heady.

(20) Another comparison of the sensory results obtained for volatile solvent extraction of four natural products, with fossil heptane versus heptane derived from Commiphora wildii produced as indicated in Example 2, is presented in Table 3. The table shows, depending on the type of heptane used (heptane produced according to an embodiment of the present description or fossil heptane) and for each natural product extracted, the yield of concrete and the olfactory description of the absolute obtained from the concrete.

(21) TABLE-US-00003 TABLE 3 Heptane produced according to Example 2 Fossil heptane Olfactory Olfactory Yield of description of Yield of description of concrete the absolute concrete the absolute Violet 1.93% Aromatic infusion of herbs, 0.18% Absolute of violet leaf green tea, verbena. Light more hay than usual. camphoraceous note, earthy. Mimosa 3.32% Green, classic cucumber note 1.16% Less green, singular in the absolutes from mimosa. balsamic notes, hay, dried herbs. Does not denature the absolute note of mimosa. Tuberose 1.80% Very different from a 0.23% Classic tuberose absolute. classic tuberose absolute, Very spicy with a floral there is a dominant fruity fatty side note. Note of note but we also find a papyrus, jasmine, heady flowery and amber-scented flowers. note. Tuberose is less distinct but the odor is reminiscent of aromatic water from Roman chamomile. Rose de Mai 2.61% The rose is recognizable 0.29% Odor very close to the fresh (May Rose) initially and then there flower with a fatty side note. is an aromatic, camphor, This is a beautiful fruity, incense aspect. Presence aldehyde flower with a light of a blackcurrant note. green note supplying freshness.

(22) Chemical analyses (GC/MS) of the concretes extracted with the heptane according to the two embodiments of the description described in Examples 1 and 2 and of the concretes extracted with the fossil heptane show similar chemical compositions. The analyses reveal a larger amount of hydrocarbons present in the concretes extracted with the fossil solvents. In contrast, the concretes extracted with the heptane according to an embodiment of the description have a larger number of volatile organic compounds with a characteristic odor, thus contributing to the supply of new olfactory facets for the concretes of the extracted natural products.

(23) Furthermore, the heptane produced as indicated in Example 2, and used for producing the concretes and absolutes of first quality, for which the yields and olfactory results, respectively, are presented in Table 3, was recycled for a second extraction, as well as the fossil heptane, in order to produce, for the same four natural products given in Table 3, a concrete and an absolute of second quality. For each natural product extracted and depending on the heptane used, the yield of concrete and the olfactory description of the absolute of second quality obtained from the concrete are presented in Table 4.

(24) TABLE-US-00004 TABLE 4 Heptane produced according to Example 2, recycled Fossil heptane, recycled Olfactory Olfactory Yield of description of Yield of description of concrete the absolute concrete the absolute Violet 0.17% Aromatic, fruity, the violet 0.13% Green, mown lawn under leaf is indistinct. rain. Mimosa 3.99% Very different from the 1.18% Seems to be a diluted absolute of first quality. version of the absolute Aldehydes, fatty. of first quality. Tuberose 0.47% Floral, honey, leathery, 0.37% Floral, a bit sweet, of animal, like a trip to the grenadine type. the souk with notes of mutton fat. Interesting new material as base note or middle note. Rose de Mai 0.48% Firstly a fresh side note, 0.49% Rosy but loss of the camphoraceous, blackcurrant, fruity side note. and then a light rose note.
Analysis Conditions:

(25) In the parts described above, the essential oils obtained from Commiphora wildii or the concretes from natural products extracted with heptane are identified by gas chromatography coupled to mass spectrometry (GC/MS). The analysis conditions are as follows: nonpolar column (Ref: Supelco SLB—5MS—380° C. max)—30 m×0.25 mm×0.30 mm—df=0.25 mm—Temperature gradient: 2° C./min from 40° C. to 220° C. then 20° C./min up to 270° C.—Analysis time: 112.5 min—Gas: He—Split 1:100—Flow rate: 1 mL/min—Quantity injected: 0.1 μL.

(26) Thus, the methods of using the heptane according to one or more embodiments of the present description, including the method of using the heptane as a solvent for extracting natural products, constitute an innovative alternative that may be useful for several applications, for example in the fields of perfumery, cosmetics or food flavorings.

(27) The heptane according to one or more embodiments of the present description makes it possible to offer a larger range of raw materials to the perfumer, thus broadening the horizons of modern perfumery, as well as cosmetics and flavorings.