Stearinsure
Bezeichnung:Stearinsure
CAS-Nr57-11-4
Englisch Name:Stearic acid
CBNumberCB4853859
SummenformelC18H36O2
Molgewicht284.48
MOL-Datei57-11-4.mol
Synonyma
Stearinsure
Octadecans?ure
1-Heptadecancarbons?ure
Cetylessigs?ure
Stearinsure physikalisch-chemischer Eigenschaften
Schmelzpunkt | 67-72 °C (lit.) |
Siedepunkt | 361 °C (lit.) |
Dichte | 0.845 g/cm3 |
Dampfdruck | 1 mm Hg ( 173.7 °C) |
FEMA | 3035 | STEARIC ACID |
Brechungsindex | 1.4299 |
Flammpunkt | >230 °F |
storage temp. | Store below +30°C. |
Löslichkeit | Practically insoluble in water, soluble in ethanol (96 per cent) and in light petroleum (bp: 50-70 °C). |
Aggregatzustand | powder |
pka | pKa 5.75±0.00(H2O t = 35) (Uncertain) |
Wichte | 0.84 (80℃) |
Farbe | White |
Geruch (Odor) | odorless mild fatty |
Geruchsart | odorless |
Wasserlöslichkeit | 0.1-1 g/100 mL at 23 ºC |
JECFA Number | 116 |
Merck | 14,8804 |
BRN | 608585 |
Dielectric constant | 2.3(22℃) |
Expositionsgrenzwerte | ACGIH: TWA 10 mg/m3; TWA 3 mg/m3 |
InChIKey | QIQXTHQIDYTFRH-UHFFFAOYSA-N |
LogP | 8.22 |
CAS Datenbank | 57-11-4(CAS DataBase Reference) |
NIST chemische Informationen | Octadecanoic acid(57-11-4) |
EPA chemische Informationen | Stearic acid (57-11-4) |
Kennzeichnung gefährlicher | Xi,F |
R-Sätze: | 38-36/37/38-11 |
S-Sätze: | 37/39-26-16 |
WGK Germany | 3 |
RTECS-Nr. | WI2800000 |
Selbstentzündungstemperatur | 395 °C |
TSCA | Yes |
HS Code | 38231100 |
Giftige Stoffe Daten | 57-11-4(Hazardous Substances Data) |
Toxizität | LD50 i.v. in mice, rats: 23±0.7, 21.5±1.8 mg/kg, L. Or, A. Wretlind, Acta Pharmacol. Toxicol. 18, 141 (1961) |
Gefahreninformationscode (GHS)
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Bildanzeige (GHS)
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Alarmwort
Warnung
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Gefahrenhinweise
H315:Verursacht Hautreizungen.
H319:Verursacht schwere Augenreizung.
H335:Kann die Atemwege reizen.
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Sicherheit
P261:Einatmen von Staub vermeiden.
P304+P340:BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P305+P351+P338:BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P405:Unter Verschluss aufbewahren.
Stearic acid Chemische Eigenschaften,Einsatz,Produktion Methoden
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ERSCHEINUNGSBILD
WEISSE KRISTALLE ODER PULVER MIT CHARAKTERISTISCHEM GERUCH. -
PHYSIKALISCHE GEFAHREN
Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich. -
ARBEITSPLATZGRENZWERTE
TLV: (als Stearate) 10 mg/m?Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK: IIb (nicht festgelegt, aber Informationen vorhanden) (DFG 2006).
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AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation des Aerosols und durch Verschlucken. -
INHALATIONSGEFAHREN
Verdampfen bei 20°C vernachlässigbar; eine belästigende Partikelkonzentration in der Luft kann jedoch beim Dispergieren des Aerosols schnell erreicht werden. -
LECKAGE
Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. -
R-Sätze Betriebsanweisung:
R38:Reizt die Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R11:Leichtentzündlich. -
S-Sätze Betriebsanweisung:
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S16:Von Zündquellen fernhalten - Nicht rauchen. -
Beschreibung
Stearic acid (STAIR-ik or STEER-ik) is the saturated fatty acid with an 18 carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid, and its chemical formula is CH3(CH2)16CO2H. Its name comes from the Greek word στ?αρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. Stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. -
Beschreibung
Stearic acid is a long-chain saturated fatty acid. It is a major component of cocoa butter and has also been found in beef fat and vegetable oils. Unlike many long-chain saturated fatty acids, dietary stearic acid does not induce hypercholesterolemia or raise LDL-cholesterol. -
Chemische Eigenschaften
Stearic acid is a hard, white or faintly yellow-colored, somewhat glossy, crystalline solid or a white or yellowish white powder. It has a slight odor (with an odor threshold of 20 ppm) and taste suggesting tallow. -
Chemische Eigenschaften
Stearic acid has a characteristic odor and taste resembling tallow. It is a mixture of solid organic acids obtained from fats consisting chiefly of stearic acid (C18H36O2) and palmitic acid (C16H32O2). -
Chemische Eigenschaften
Stearic acid, CH3(CH2)16COOH, is a white or colorless, waxlike solid with a melting point of 70°C (158 OF), and a boiling point of 232°C (450 OF) at 2 kPa. It is soluble in alcohol, ether, and chloroform,and is insolublein water. Stearic acid, nature's most common fatty acid, is derived from natural animal and vegetable fats. Also known as n-octadecanoic acid, stearic acid is used in the preparation of metallic stearates, as a lubricant, and in pharmaceuticals, cosmetics, candles, and food packaging. -
Occurrence
Stearic acid is naturally present in the glycerides of animal fats and most vegetable oils. Reported found in fresh apple, banana, Vitis vinifera L., melon, tomato, ginger, blue cheeses, cheddar cheese, Swiss cheese, feta cheese, buttermilk, raw fatty fish, raw lean fish, raw shrimp, grapefruit juice, guava, papaya, cucumber, saffron, pork and lamb liver, pork fat, hop oil, beer, cognac, rum, whiskies, sherry, tea, peanut oil, soybean, roast coconut, coconut milk, avocado, passion fruit, rose apple, mushroom, starfruit, fenugreek, mango, cardamom, cooked rice, prickly pear, dill seed, buckwheat, malt, wort, cassava, loquat, shrimp, crab, cape gooseberry and Chinese quince. -
Verwenden
Stearic Acid is a fatty acid that is a mixture of solid organic acids obtained principally from stearic acid and palmitic acid. it is practi- cally insoluble in water. it functions as a lubricant, binder, and defoamer. it is used as a softener in chewing gum base. -
Verwenden
stearic acid is an emulsifier and thickening agent found in many vegetable fats. Stearic acid is the main ingredient used in making bar soaps and lubricants. It occurs naturally in butter acids, tallow, cascarilla bark, and in other animal fats and oils. Stearic acid may cause allergic reactions in people with sensitive skin and is considered somewhat comedogenic. -
Verwenden
Generally applications of stearic acid exploit its bifunctional character, with a polar head group that can be attached to metal cations and a nonpolar chain that confers solubility in organic solvents. The combination leads to uses as a surfactant and softening agent. Stearic acid undergoes the typical reactions of saturated carboxylic acids, notably reduction to stearyl alcohol, and esterification with a range of alcohols.
Soaps , cosmetics , detergents
Stearic acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products. Soaps are not made directly from stearic acid, but indirectly by saponification of triglycerides consisting of stearic acid esters. Esters of stearic acid with ethylene glycol; glycol stearate and glycol distearate, are used to produce a pearly effect in shampoos, soaps, and other cosmetic products. They are added to the product in molten form and allowed to crystallize under controlled conditions. Detergents are obtained from amides and quaternary alkylammonium derivatives of stearic acid.
Lubricants , softening and release agents
In view of the soft texture of the sodium salt, which is the main component of soap, other salts are also useful for their lubricating properties. Lithium stearate is an important component of grease. The stearate salts of zinc, calcium, cadmium, and lead are used to soften PVC. Stearic acid is used along with castor oil for preparing softeners in textile sizing. They are heated and mixed with caustic potash or caustic soda. Related salts are also commonly used as release agents, e.g. in the production of automobile tires.
Niche uses
Being inexpensively available and chemically benign, stearic acid finds many niche applications. When making plaster castings from a plaster piece mold or waste mold and when making the mold from a shellacked clay original. In this use, powdered stearic acid is mixed in water and the suspension is brushed onto the surface to be parted after casting. This reacts with the calcium in the plaster to form a thin layer of calcium stearate which functions as a release agent. When reacted with zinc it forms zinc stearate which is used a lubricant for playing cards (fanning powder) to ensure a smooth motion when fanning. In compressed confections, it is used as a lubricant to keep the tablet from sticking to the die.
Fatty acids are classic components of candle - making. Stearic acid is used along with simple sugar or corn syrup as a hardener in candies.
Stearic acid is used to produce dietary supplements.
In fire works, stearic acid is often used to coat metal powders such as aluminium and iron. This prevents oxidation, allowing compositions to be stored for a longer period of time. Stearic acid is a common lubricant during injection molding and pressing of ceramic powders. It is also used as a mold release for foam latex that is baked in stone molds. . -
Verwenden
Pharmaceutic aid (emulsion adjunct); pharmaceutic aid (tablet and/or capsule lubricant). -
Definition
A solid carboxylic acid present in fats and oils as the glyceride. -
Vorbereitung Methode
Stearic Acid occurs in many animal and vegetable fats and oils, but it is more abundant in animal fat (up to 30 %) than vegetable fat (typically < 5 % ) . The important exceptions are cocoa butter and shea butter where the stearic acid content (as a triglyceride) is 28 – 45 %.
Stearic acid is prepared by treating these fats and oils with water at a high pressure and temperature (above 200 °C), leading to the hydrolysis of triglycerides. The resulting mixture is then distilled. Commercial stearic acid is often a mixture of stearic and palmitic acids, although purified stearic acid is available.
In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery via acetyl-CoA . -
Definition
ChEBI: A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics. -
Vorbereitung Methode
Stearic acid is manufactured by hydrolysis of fat by continuous exposure to a countercurrent stream of high-temperature water and fat in a high-pressure chamber. The resultant mixture is purified by vacuum steam distillation and the distillates are then separated using selective solvents.
Stearic acid may also be manufactured by the hydrogenation of cottonseed and other vegetable oils; by the hydrogenation and subsequent saponification of olein followed by recrystallization from alcohol; and from edible fats and oils by boiling with sodium hydroxide, separating any glycerin, and decomposing the resulting soap with sulfuric or hydrochloric acid. The stearic acid is then subsequently separated from any oleic acid by cold expression.
Stearic acid is derived from edible fat sources unless it is intended for external use, in which case nonedible fat sources may be used. The USP32–NF27 states that stearic acid labeled solely for external use is exempt from the requirement that it be prepared from edible sources. Stearic acid may contain a suitable antioxidant such as 0.005% w/w butylated hydroxytoluene. -
synthetische
Commercially it is produced by the hydrogenation of the unsaturated 18-carbon fatty acids of soybean, cottonseed or other vegetable oils. When obtained from animal fats by hydrolysis and fractional crystallization, commercial stearic acid is a mixture of solid organic acids, chiefly palmitic and stearic acids. Commercial products containing about 90% stearic acid are produced by hydrolysis and crystallization of a completely hydrogenated vegetable oil or by fractional distillation of fatty acid mixtures obtained from tallow -
Trademarks
Hystrene 5016 (Witco). -
Aroma threshold values
Detection: 20 ppm -
Synthesis Reference(s)
Synthetic Communications, 15, p. 759, 1985 DOI: 10.1080/00397918508063869 -
Allgemeine Beschreibung
White solid with a mild odor. Floats on water. -
Air & Water Reaktionen
Slightly soluble in water. -
Reaktivität anzeigen
Stearic acid is incompatible with strong oxidizers and strong bases. Stearic acid is also incompatible with reducing agents. -
Health Hazard
Compound is generally considered nontoxic. Inhalation of dust irritates nose and throat. Dust causes mild irritation of eyes. -
Brandgefahr
Stearic acid is combustible. Stearic acid can heat spontaneously. -
Pharmazeutische Anwendungen
Stearic acid is widely used in oral and topical pharmaceutical formulations. It is mainly used in oral formulations as a tablet and capsule lubricant, although it may also be used as a binder or in combination with shellac as a tablet coating. It has also been suggested that stearic acid may be used in enteric tablet coatings and as a sustained-release drug carrier.
In topical formulations, stearic acid is used as an emulsifying and solubilizing agent. When partially neutralized with alkalis or triethanolamine, stearic acid is used in the preparation of creams. The partially neutralized stearic acid forms a creamy base when mixed with 5–15 times its own weight of aqueous liquid, the appearance and plasticity of the cream being determined by the proportion of alkali used.
Stearic acid is used as the hardening agent in glycerin suppositories.
Stearic acid is also widely used in cosmetics and food products. -
Biochem/physiol Actions
β-Oxidation of stearic acid yields eight FADH2 (flavin adenine dinucleotide) and NADH2 (nicotinamide adenine dinucleotide) molecules and nine acetyl-CoA molecules. -
Sicherheitsprofil
Poison by intravenous route. A human sktn irritant. Questionable carcinogen with experimental tumorigenic data by implantation route. Combustible when exposed to heat or flame. Heats spontaneously. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. -
Sicherheit(Safety)
Stearic acid is widely used in oral and topical pharmaceutical formulations; it is also used in cosmetics and food products. Stearic acid is generally regarded as a nontoxic and nonirritant material. However, consumption of excessive amounts may be harmful.
LD50 (mouse, IV): 23 mg/kg
LD50 (rat, IV): 21.5 mg/kg -
Carcinogenicity
Stearic acid was administered subcutaneously to several groups of Swiss–Webster mice at doses of 0.05 or 0.5mg once weekly for 25 weeks (total dose of 1.3–130 mg), 1.0 mg thrice a week for a total of 10 injections or 1.0 mg twice weekly for a total of 82 injections. No neoplasms were reported in these studies . In 3 groups of 10–15 BALB/c mice administered 0.05 mg or 0.5 mg stearic acid (twice weekly for 52 or 57 weeks), one pulmonary neoplasm was detected in each group after 19–21 months.Afewsubcutaneous sarcomas and one adrenal carcinoma were also reported.No injection site sarcomas or other carcinogenic effects were reported by the same authors in a later study of mice injected with 0.05–0.5 mg weekly for 26 weeks. Rats given subcutaneous injections of 0.05 or 0.5 mg stearic acid weekly for 26 weeks did not develop sarcomas at the site of injection. When rat fibroblast cells were transfected with an activated human c-H-ras oncogene and the cells subsequently grown in a medium supplemented with stearic acid (20–80 mM), there was a marked increase in the number of transformed foci. Stearic acid inhibited the colony-forming ability of four out of five rat and two human tumor continuous cell lines in vitro. Using rats pretreated with nitrosomethyl urea as a model for mammary carcinoma, Habib et al. demonstrated that subcutaneous injection of stearic acid at weekly intervals prevented tumor development. Increasing levels of stearate in the diet resulted in decreased mammary tumor incidence and increased time to tumor in mice. -
Stoffwechsel
An isotope labeling study in humans concluded that the fraction of dietary stearic acid oxidatively desaturated to oleic acid was 2.4 times higher than the fraction of palmitic acid analogously converted to palmitoleic acid. Also, stearic acid was less likely to be incorporated into cholesterol esters. In epidemiologic and clinical studies stearic acid was associated with lowered LDL cholesterol in comparison with other saturated fatty acids. These findings may indicate that stearic acid is healthier than other saturated fatty acids. -
Lager
Stearic acid is a stable material; an antioxidant may also be added to it. The bulk material should be stored in a wellclosed container in a cool, dry place. -
läuterung methode
Crystallise stearic acid from acetone, acetonitrile, EtOH (5 times), aqueous MeOH, ethyl methyl ketone or pet ether (b 60-90o), or by fractional precipitation by dissolving in hot 95% EtOH and pouring into distilled water, with stirring. The precipitate, after washing with distilled water, is dried under vacuum over P2O5. It has also been purified by zone melting and partial freezing. [Tamai et al. J Phys Chem 91 541 1987, Beilstein 2 IV 1206.] -
Inkompatibilitäten
Stearic acid is incompatible with most metal hydroxides and may be incompatible with bases, reducing agents, and oxidizing agents.
Ointment bases made with stearic acid may show evidence of drying out or lumpiness due to such a reaction when compounded with zinc or calcium salts.
A number of differential scanning calorimetry studies have investigated the compatibility of stearic acid with drugs. Although such laboratory studies have suggested incompatibilities, e.g. with naproxen, they may not necessarily be applicable to formulated products.
Stearic acid has been reported to cause pitting in the film coating of tablets applied using an aqueous film-coating technique; the pitting was found to be a function of the melting point of the stearic acid. -
Regulatory Status
GRAS listed. Accepted as a food additive in Europe (fatty acids). Included in the FDA Inactive Ingredients Database (sublingual tablets; oral capsules, solutions, suspensions, and tablets; topical and vaginal preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Stearic acid Upstream-Materialien And Downstream Produkte
Upstream-Materialien
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Downstream Produkte
- Poly(ethylene glycol) distearate
- N,N'-Ethylendi(stearamid)
- Cadmiumdistearat
- Calciumbis(2-(1-carboxylatoethoxy)-1-methyl-2-oxoethyl)distearat
- Drostanolon
- Lead stearate,dibasic
- Greasing agent,cationic
- softening agent SCI-A
- calcium stearyl lactate
- butyl rubber
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