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Encyclopedia Britannica - Main :: PAS-PER |
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PERFUMERY (Lat. per, through, and fumare, to smoke) , the preparation of perfumes, or substances which are pleasing to the sense of smell. Perfumes may be divided into two classes, the first of which includes all primitive or simple odoriferous bodies derived from the animal or vegetable kingdom, as well as the definite chemical compounds specially manufactured, while the second comprises the various " bouquets " or " melanges " made by blending two or more of the foregoing in varying proportionstoilet powders, dentifrices, sachets, &c. To the former class belong (1) the animal products, ambergris, castor, civet, musk; (2) the essential oils (also called attars), mostly procured by the distillation of the stems, leaves, flowers
Natural Perfumes.The animal perfumes are extremely limited in number. Ambergris (q.v.), one of the most important, is secreted by the sperm whale; musk (q.v.), the best known scent of this class, is secreted by the male musk-deer and other animalsmusk-ox, musk-rat, &c.; civet (q.v.) is a musky scent named from the animal which secretes it; and castor or castoreum is a somewhat similar secretion of the beaver (q.v.). More important are the scents yielded by flowering plants. As a general rule fragrant flowers
rosemary
The natural sources of the attars or essential oils are the different parts of the plants which yield themthe wood (lign, aloe, santal, cedar
tuberose
The gum-resins and resins have been employed as perfumes from the earliest times. The more important are incense, frankincense and myrrh (q.v.). They are largely used in the manufacture of perfumes, both for burning as pastilles, ribbon of Bruges, incenses, &c., and in tinctures, to which they impart their characteristic odours, affording, at the same time, a certain fixity to other perfumes of a more fleeting nature when mixed with them. Synthetic Perfumes.Under this heading are included all perfumes in which artificial substances are odorous ingredients. Although the earliest perfumes of this class were introduced in about the middle of the 19th century, the important industry which now prevails is to be regarded as dating from the 'seventies and 'eighties. Three main lines of development may be distinguished: (1) the chance discovery of substances which have odours similar to natural perfumes; (2) the elucidation of the composition of the natural scents, and the chemical constitution of their ingredients, followed by the synthetic preparation of the substances so determined; and (3), which may be regarded as connected with (2), the extraction and separation of the essential oils yielded by less valuable plants, and their reblending to form marketable perfumes. The first synthetic perfume was the " essence of Mirbane " introduced by Collas in about 185o; this substance was the nitro-benzene discovered by E. Mitscherlich in 1834. Soon after-wards many esters of the fatty acids simulating the odours of fruits were introduced; and in 1888 Baur discovered the " artificial musks," which are derivatives of s-trinitrobenzene. The above are instances of the first line of progress. The second line has for early examples the cases of artificial oil of wintergreen, which followed Cahour's discovery that the natural oil owed its . odour, in the main, to methyl salicylate, and of artificial oil of bitter almonds which followed the preparation of benzaldehyde from benzal chloride in 1868. The synthesis of coumarin, the odorous principle of hay and woodruff, by Sir W. H. Perkin in 1868; of vanillin, the odorous principle of vanilla, by F. Tiemann and W. Haarman.n in 1875; and of ionone, almost identical with the natural irone, the odorous principle of violets, by Tiemann and P. Kruger in 1898, are to be regarded as of the highest importance. Equally important are the immense strides made in the elucidation of the constitution and syntheses of the terpenes (q.v.), a group of compounds which are exception-ally abundant as odorous principles in the essential oils. The present state of our knowledge does not permit a strict correlation of odour and chemical constitution. One theory regards odour as due to " osmophores," or odour-producing groups, in much the same way as colour is associated with chromophores. Such osmophores are hydroxyl (OH), aldehyde (CHO), ketone (CO), ether (O), nitrile (CN), nitro (NO2), &c.; we may also notice the isonitrile group (NG) associated with an unpleasant odour, and the iso-thiocyanate group (NCS) to which the mustard oils owe their characteristic smell. The same group, however, is not invariably associated with the same odour, or even any odour at all, as, for instance, in such closely related compounds as the members of a homologous series. For n-Octyl acetate, C8H,7.O2CCH3, has the odour of oranges. Isoamyl example, the lower fatty aldehydes have unpleasant odours, those with ten carbon atoms (and also double linkages, which in itself may affect odour) form some of the most delicate scents, while the higher members are odourless. The absence of odour in the higher members may be possibly associated with the low volatility exhibited by compounds of high molecular weight. Certain osmophores have practically equal effects; for example, benzaldehyde, nitrobenzene, benzonitrile, and phenyl azoimide have practically identical odours, and among the " artificial musks," a nitro group may be replaced by the azoimido group without the odour being modified. As a general rule, homologues have similar odours, but many exceptions are known. For example the methyl and ethyl ethers of [3-naphthol have the odour of neroli; on the other hand, of the esters of anthranilic acid, the methyl has the odour of orange blossoms, the ethyl has a slight odour, and the isobutyl is odourless. The introduction of a methyl group into the benzene ring generally involves little or no change in odour; but when it (and more especially higher alkyl radicals) is introduced into side chains the odour may be entirely changed. For example, benzene and its homologues have similar odours; phthalide is odourless, but the isopropyl and butyl phthalides, in which substitution occurs in the side chain, smell of celery. Especially characteristic are the derivatives of phenylacetylene. This hydrocarbon is distinctly unpleasant; on the other hand, para-ethyl and paramethyl phenylacetylene smell of anise. While the triply-linked carbon system is generally associated with strong and unpleasant odours, the doubly linked system gives pleasant ones. Thus the unpleasant phenylacetylene, C6H5C:CH, is contrasted with styrolene, C6H5.CH:CH2, which occurs in storax, and phenylpropiolic aldehyde with cinnamic aldehyde, C6H5CH:CHCHO, which occurs in cassia and cinnamon. The reduction of a double to a single linkage may not destroy odour. Thus hydrocinnamic aldehyde, the reduction product of cinnamic aldehyde, smells of jasmine and lilac
The concentration and even the solvent has considerable effect on the odour of a substance. Many of the artificial principlesvanillin, heliotropine, ionone, &c.have very different odours in strong and in dilute solution; phenyl acetic acid and /3-naphthylamine are odourless when solid, but have disagreeable odours when dissolved. Traces of impurities often have the effect of making odourless or pleasant- smelling compounds quite intolerable. Acetylene as generated from calcium carbide, and carbon disulphide prepared from its elements are quite intolerable, though when pure they are, at least, not unpleasant; artificial benzaldehyde must be very care-fully purified before it can be used in the preparation of the more delicate scents. In all cases the natural scents are complex mixtures of many ingredients, and a variation in the amount of any one may completely alter the scent. Such mixtures would be difficult to reproduce economically; the perfumer is content with a product having practically an identical odour, with or without the natural substance which it is designed to compete with. We now give an account of the artificial scents, principally arranged according to their chemical relations. The fatty esters are interesting as providing many of the fruit essences; in fact, by appropriate blending, any fruit odour can be reproduced. Their use, however, is inhibited by the fact that they irritate the respiratory organs, producing coughing and headaches. Isobutyl carbinol acetic ester (amyl acetate), %CH3)2CHCH2CH2.00CH3, forms when in dilute alcoholic solution the artificial pear oil; a similar odour is possessed by isoatnyl-n-butyrate, C3H,CO2C,Hn. propionate, C,Hu.O2CC2H5, and ethyl-n-butyrate, C3H,O2CC2H5, have the odour of pineapple, the latter constituting the artificial pineapple oil of commerce. Isoamyl isovalerate, C5H,1.O2CC4H9, is the artificial apple oil. Of the fatty ketones, methyl nonyl ketone, CH3COC,H19i which is the scent of oil of rue, and methyl-ethyl acetone
chief
acetone
chief
Name of Oil. Source. Constituents. Anise . . Pimpinella anisum Anethole, estragole. Bay . . . Pimenta acris Eugenol, methyl eugenol, Bergamot . Citrus bergamia chavicol, estragole,myrcene, Cajaput . . Melaleuca, sp. phellandrene. Cassia . . Cinnamonum cassia Linalol, linalyl acetate, d- Caraway . Carum carvi limonene, bergaptene. Camphor . Cinnamonum camphor Cineol. Chamomile . Anthemis nob ills Cinnamic aldehyde, cinnamyl Cinnamon . Cinnamonum Zeylani- acetate. Clove . cum Carvone, d-limonene. Coriander . Eugenia caryophyllata d-Pinene, phellandrene, terpi- Cumin . . Coriandum sativum neol, eugenol, safrole. Eucalyptus . Cuminum cymium Isobutyl and isoamyl esters Fennel . . Eucalyptus globulus of angelic and tiglic acids. Geranium . Foeniculum vulgare Cinnamic aldehyde. Jasmine . . Andropogon schoen- Eugenol. Lavender . ant has Linalol. Lemon . . Jasminum grandi- Cumic aldehyde, cymene. Lemon-grass forum Cineol, d-pinene, and fatty Neroli . . Lavendula vera aldehydes. Orange . . Citrus limonum Anethole, fenchone, d-pinene. Peppermint . Andropogon citratus Geraniol, citronellol. Pine-needle . Citrus bigardia Methyl anthranilate, indol, Rose . . . Citrus aurantium benzyl alcohol, benzyl ace- Rose. . Mentha piperita tate, linalol, linalyl acetate. Geranium . Finns sylvestris Linalol, 1-linalyl acetate. Rosemary
Sage . . . Pelargonium odoratis citronellal, geranyl acetate, Sassafras . semum linalol. Spearmint . Rosamarinus officina- Citral. Star anise . lis 1-Linalol, geraniol, limonene, Tansy . . Salvia offcinalis methyl anthranilate. Thyme . . Sassafras officinalis d-Limonene. Wormwood . Mentha viridis Menthol, menthyl acetate and Ylang-ylang Illicium anisatum valerate. Tanacetum vulgare d-Pinene, d-sylvestrene. Thymus vulgaris Geraniol, I-citronellol. Artemisia absinthum Geraniol, citronellol. Cananga odorata Pinene, camphene, camphor, cineol, borneol. Pinene,cineol,thujone,borneol. Safrole. 1-Linalol, 1-carvone. Anethole. Thujone. Thymol. } Thujone and thujyl esters. 1-Linalol, geraniol. ' See J. B. Cohen, Organic Chemistry, p. 532 ; or J. Parry, Chemistry of Perfumes (1908). The chief benzenoid compounds used as perfumes are aldehydes, oxyaldehydes, phenols and phenol ethers. Benzaldehyde has the odour of almonds, cinnamic aldehyde of cinnamon, and cumin aldehyde gives the odour to cumin oil. Of oxyaldehydes salicylaldehyde gives the odour to spiraea oil, and vanillin is the active ingredient of vanilla (q.v.). Anisaldehyde smells like hawthorn, and is extensively used under the name aubepine for scenting soaps and extracts. Carvacrol and thymol are isomeric methyl propyl phenols; both have the odour of thyme. Of phenol ethers eugenol (ally! guaiacol) has the odour of cloves, and anethole (allyl phenyl methyl ether) is the chief constituent of anise oil, being chiefly used in the manufacture of liqueurs. Several piperonyl compounds are of commercial importance. The aldehyde, CH2[O]2:C6H3CHO(1,2'4), piperonal, has the odour of heliotrope; an allyl derivative, safrole CH2[O]2:C6H3C3H6(I,2,4), occurs in sassafras, while apiole or dimethoxy saf role has the odour of parsley oil. Of other synthetic perfumes amyl salicylate is used under the names of orchidee or trefol as the basis of many perfumes, in particular of clover scents; methyl anthranilate occurs in the natural neroli and other oils, and has come into considerable use in the preparation of artificial bergamot, neroli, jasmine and other perfumes (the Trolene, Marceol and Amanthol of the Actien Gesellschaft fur Anilin Fabrikation have this substance as a base) ; the " artificial musks " are derivatives of s-trinitrobenzene; coumarin is the principle of wood-ruff ; and S-naphthol methyl ether is used for the preparation of artificial neroli. The Odophone.The most important element in the perfumer's art is the blending of the odorous principles to form a mixture which gratifies the sense of smell. Experience is the only guide. It is impossible to foretell the odour of a mixture from the odours of its components. Septimus Piesse endeavoured to show that a certain scale or gamut existed amongst odours as amongst sounds, taking the sharp
Other Branches of Perfumery.As a natural outcome of the development of the perfume industry, scented articles for toilet and other uses are now manufactured in large quantities. Soaps, toilet powders, tooth powders, hair-washes, cosmetics generally, and note-paper have provided material on which the perfumer works. For the preparation of scented soaps two methods are in use; both start with a basis either of fine yellow soap (which owes its odour and colour to the presence of resin), or of curd soap (which is hard, white and odourless, and is prepared without resin). In one process the soap is melted by superheated steam, and while still hot and semi-fluid mixed by means of a stirrer of wood with iron cross-bar, technically called a " crutch," with the attars and colouring matter. It is then removed from the melting pan to a rectangular iron mould or box, the sides of which can be removed by unscrewing the tie-rods which hold them in position; when cold the mass is cut irto slabs and bars with a thin brass wire. In the other or cold process the soap is first cut into chips or shavings by a plane or " chipping machine," then the colouring matters are added and thoroughly incorporated by passing the soap between rollers; the tinted soap emerges in a continuous sheet but little thicker than paper. The perfumes are then added, and after standing
Toilet Powders are of various sorts. They consist of rice- starch
starch
Tooth Powders consist for the most part of mixtures of powdered orris-root with precipitated chalk, and some other constituent destined to particularize it as to properties or flavour, such ascharcoal, finely pulverized pumice, quassia, sugar, camphor, &c. The perfume of the contained orris-root is modified, if required, by the addition of a little of some perfume. Tooth Pastes are formed of the same constituents as the powders, and are worked into a paste by the addition of a little honey or glucose syrup, which sub-stances are usually believed ultimately to have an injurious effect on the teeth. Perfume Sachets consist either of a powder composed of a mixture of vanilla, musk, Tonclua beans, &c., one or other predominating as required, contained in an ornamental silk sac; or of some of the foregoing substances spread upon card or chamois leather or flannel after being made into a paste with mucilage and a little glycerin. When dry the card so prepared is daintily covered with various parti-coloured silks for sale. Where the ingredients employed in their manufacture are of good quality these cards, known as " peau d'Espagne " sachets, retain their odour unimpaired for years. Adulterations.T here is, as might be expected, considerable scope for the adulteration of the " matieres premieres " employed in perfumery. Thus, in the case of musk, the " pods " are frequently found to be partially emptied of the grain, which has been replaced by hide or skin, while the weight has been increased by the introduction of lead, &c. In other instances the fraud consists in the admixture of refuse grain, from which the odour has been exhausted with spirit, with dried blood, and similar substances, whilst pungency is secured by the addition of ammonium carbonate. Attar of rose is diluted with attar of Palma rosa, a variety of geranium of only a quarter or a fifth of the value. The main adulterant of all the natural essential oils, however, is castor oil. This is a bland neutral body, practically odourless, and completely soluble in alcohol; it therefore presents all the requisites for the purpose. End of Article: PERFUMERY (Lat. per, through, and fumare, to smoke) If you wish, you can link directly to this article.
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