112-30-1 Usage
description
1-Decanol, also known as decyl alcohol or n-decyl alcohol, is a straight chain fatty alcohol with ten carbon atoms and the molecular formula CH3(CH2)9OH. It is a colorless viscous liquid that is insoluble in water. It is colorless and has a strong odor. It is a clear colorless liquid with a sweet fat-like odor. It has a flash point of 180°F. It is less dense than water and insoluble in water. Its vapors are heavier than air.
Applications
Decyl alcohol can be used for the production of plasticizers, lubricants, surfactants and solvents. It is also used to study the thermal properties of polymer-monolithic stationary phases. Furthermore, it can used to enhance homomeric glycine receptor function. In addition to this, it is used in daily flavor, food flavor and cosmetics. In addition, the 5HT2α receptors were inhibited by the presence of decyl alcohol. This action has many psychological repercussions on an individual. It can also be used as a plant growth regulator of tobacco.
Warning and Risk
Decyl alcohol causes a high irritability to skin and eyes, when splashed into the eyes it can cause permanent damage. Also inhalation and ingestion can be harmful, it can also function as a narcotic. It is also harmful in the environment.
Chemical Properties
1-Decanol is a clear colorless to slightly yellow liquid and has a floral odor resembling orange flowers and a slight, characteristic fatty taste. The threshold odor concentration in air for decyl alcohol (isomer not specified) was reportedly 6.3 ppb. soluble in glacial acetic acid, ethanol, benzene, petroleum ether, easily soluble in ether.
Occurrence
Reported in the essential oils of ambrette seeds and almond flowers; also in citrus oils, fermented beverages,
apple juice, bilberry, American cranberry, papaya, raspberry, cheeses, milk, butter, beef, pork, beer, cognac, whiskey, red, white and
sparkling wines, coriander seeds and cardamom.
Uses
1-Decanol is a long chain alcohol that has been seen to enhance homomeric glycine receptor function. In addition, the 5HT2α receptors were inhibited by the presence of 1-decanol. This action has many psychological repercussions on an individual. 1-Decanol is also used in the manufacture of plasticizers, synthetic lubricants, petroleum additives, herbicides, surface active agents, solvents. Has moderate antifoaming capacity.
Definition
ChEBI: 1-Decanol is a fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms. It has a role as a metabolite and a protic solvent. It is a primary alcohol and a fatty alcohol.
Production Methods
1-Decanol is prepared commercially by sodium reduction or
by the high-pressure catalytic reduction of coconut oil,
coconut fatty acids, or esters . It is also produced
by the Ziegler process, which involves oxidation of trialkylaluminum
compounds.
Preparation
By sodium reduction or high-pressure catalytic hydrogenation of the esters of naturally occurring capric acid, or by oligomerization of ethylene using aluminium alkyl technology.
Application
decyl alcohol can be used for any number of functions, including as an emollient, a foam-booster, a surfactant and a viscosity controller, as well to mask odor and as a fixative in perfumes. Decyl alcohol occurs naturally in sweet orange and ambrette seed. It is also derived commercially from liquid paraffin.
Aroma threshold values
Detection: 6 to 47 ppb
Synthesis Reference(s)
The Journal of Organic Chemistry, 38, p. 3223, 1973 DOI: 10.1021/jo00958a031Synthetic Communications, 12, p. 287, 1982 DOI: 10.1080/00397918209409235
General Description
A clear colorless liquid with a sweet fat-like odor. Flash point 180°F. Less dense than water and insoluble in water. Vapors are heavier than air.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Decyl alcohol attacks plastics. REF [Handling Chemicals Safely, 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water, [Merck 11th ed., 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid, [Chem. Eng. News 45(43):73(1967); J, Org. Chem. 28:1893(1963)]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites, [NFPA 491 M, 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].
Health Hazard
Direct contact can produce eye irritation; low general toxicity.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Safety Profile
Moderately toxic by
skin contact. Wdly toxic by ingestion and
inhalation. A severe human skin and eye
irritant. Experimental reproductive effects.
Questionable carcinogen with experimental
tumorigenic data. Combustible when
exposed to heat or flame; can react with
oxidzing materials. To fight fire, use foam,
CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ALCOHOLS.
Synthesis
Synthetically prepared from coconut oil derivatives; by reduction of some capric esters, such as methyl caprate.
Carcinogenicity
1-Decanol showed weak to
moderate tumor-promoting activity when applied three
times a week for 60 weeks to the skin of female Swiss
mice that previously received an initiating dose of dimethylbenz[
a]anthracene .
Metabolism
See alcohol C-8.
Purification Methods
Fractionally distil n-decanol in an all-glass unit at 10mm pressure (b 110o), then fractionally crystallise by partial freezing. Also purify by preparative GLC, and by passage through alumina before use. [Beilstein 1 IV 1815.]
Check Digit Verification of cas no
The CAS Registry Mumber 112-30-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 2 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 112-30:
(5*1)+(4*1)+(3*2)+(2*3)+(1*0)=21
21 % 10 = 1
So 112-30-1 is a valid CAS Registry Number.
InChI:InChI=1/C16H38N2.C2H6O.2BrH/c1-17(2,3)15-13-11-9-7-8-10-12-14-16-18(4,5)6;1-2-3;;/h7-16H2,1-6H3;3H,2H2,1H3;2*1H/q+2;;;/p-2
112-30-1Relevant articles and documents
Process Development for the Rhodium-Catalyzed Reductive Amination in a Thermomorphic Multiphase System
Künnemann, Kai U.,Bianga, Jonas,Scheel, Ricarda,Seidensticker, Thomas,Dreimann, Jens M.,Vogt, Dieter
, p. 41 - 49 (2020)
For the first time, the successful application of the homogeneously catalyzed reductive amination in a thermomorphic multiphase system (TMS) and the first reported scale-up of this reaction into a continuous process, which recovers and recycles the homogeneous catalyst in flow, is presented. Herein, the model substrate 1-decanal reacts with the secondary amine diethylamine to form the corresponding product N,N-diethyldecylamine. A thermomorphic multiphase system (TMS) is established as a recycling strategy to recover and reuse the catalyst for the continuous process. After screening different solvents for the TMS and optimizing the reaction conditions in batch mode, the recycling of the rhodium catalyst was realized in a fully automated miniplant. Parameters influencing the stability of the process were identified and optimized to develop the continuous process. The process was operated in a steady state over 90 h with yields >90% of the desired product and low catalyst leaching 1%/h.
Reduction of Carboxylic Acid with 2-Propanol over Zirconia-Titania
Takahashi, Kyoko,Shibagaki, Makoto,Kuno, Hideyuki,Matsushita, Hajime
, p. 839 - 840 (1993)
The reduction of long carbon chain carboxylic acids or the esters with 2-propanol proceeded efficiently over zirconia-titania at atmospheric pressure, and the corresponding alcohols were obtained.Methyl 9-octadecenoate was reduced to give 9-octadecen-1-ol in a 58percent yield.
Reduction of aldehydes using trialkylboranes in ionic liquids
Kabalka,Malladi
, p. 2191 - 2191 (2000)
Non-aqueous ionic liquids, molten salts, have been found to enhance organoboron mediated reductions of aldehydes.
Deprotection of mono and dimethoxy phenyl methyl ethers using catalytic amounts of DDQ
Chandrasekhar,Sumithra,Yadav
, p. 1645 - 1646 (1996)
4-Methoxy and 3,4 dimethoxy benzyl ethers have been deprotected with catalytic amounts of DDQ by oxidative recycling of the byproduct DDHQ with FeCl3 for the first time.
Selective Removal of the Methyldiphenylsilyl Protecting Group Using Azide Ion
Monger, Steven J.,Parry, David M.,Roberts, Stanley M.
, p. 381 - 382 (1989)
Sodium azide in dimethylformamide effects the cleavage of the methyldiphenylsilyl ether bond under conditions whereby t-butyldimethylsilyl ethers and t-butyldiphenylsilyl ethers are stable.
Hydrogen transfer hydrozirconation of alkenes with iBuZrCp2Cl catalyzed by Lewis-acidic metal compounds containing Al, Zn, Si, Ag, and Pd
Makabe, Hidefumi,Negishi, Ei-Ichi
, p. 969 - 971 (1999)
The hydrozirconation reaction of monosubstituted alkenes with iBuZrCp2Cl can be significantly accelerated by catalytic amounts of various Lewis acidic metal compounds, most notably AlCl3, Me3SiI, and Pd complexes, such as Li2PdCl4 and Cl2Pd(PPh3)2.
Structure sensitivity in the ruthenium nanoparticle catalyzed aqueous-phase Fischer-Tropsch reaction
Quek, Xian-Yang,Pestman, Robert,Van Santen, Rutger A.,Hensen, Emiel J. M.
, p. 3510 - 3523 (2014)
Low-temperature Fischer-Tropsch reaction data are reported for Ru nanoparticles suspended in the water phase. Their activity and selectivity strongly depends on particle size, when varied between 1 to 5 nm. Small particles display high oxygenates selectivity. The Anderson-Schulz-Flory (ASF) chain-growth probability for oxygenates is significantly lower than that observed for hydrocarbons. The chain growth parameter for hydrocarbon formation is independent of particle size. For oxygenates it is constant only for particles larger than 3 nm. Oxygenate and hydrocarbon formation occur on different sites. The ASF chain-growth probability for oxygenate formation increases with temperature. For very small 1.2 nm particles it shows a maximum as a function of temperature. This unusual temperature dependence is due to relatively slow CO dissociation compared to the rate of C-C bond formation. This journal is
Convenient method for the preparation of catecholborane and promotion of the formation of alkenyl catecholborane using BH3 complexes
Suseela, Y.,Periasamy, M.
, p. 47 - 52 (1993)
Catecholborane is prepared in benzene by passing B2H6, generated from I2/NaBH4, through a suspension of catechol at 25 deg C.The reagent prepared in this way is used for hydroboration-oxidation of representative alkenes and alkynes at 80 deg C.Hydroboration of 1-alkynes followed by iodination with I2/NaOH gives the corresponding trans-1-alkenyl iodides in 70-72percent yield.The alkenyl catecholboranes can be prepared at 25 deg C by performing the reaction in the presence of 10 molepercent of H3B:N(C2H5)2Ph or H3B:THF.The reaction is believed to go through hydroboration of thealkynes by borane followed by exchange with catecholborane.Studies of the preparation of dialkylphenoxyboranes and alkenyldiphenoxyboranes through hydroboration of 1-decene and 1-decyne by use of H3B:N(C2H5)2Ph and phenol are also reported.
Deprotection of benzyl ethers using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under photoirradiation
Rahim, Mohammad Abdur,Matsumura, Shuichi,Toshima, Kazunobu
, p. 7307 - 7309 (2005)
The deprotection of benzyl ethers was effectively realized in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in MeCN under photoirradiation using a long wavelength UV light.
Reactions of Amino Acid Decyl Esters with Nucleophiles Catalyzed by Polymer-Supported Amine-Metal Complexes
Ohtani, Noritaka,Inoue, Yukihiko,Inagaki, Yuichi,Fukuda, Kenji,Nishiyama, Taisuke
, p. 1669 - 1676 (1995)
The reactions of alanine decyl ester (AlaODc) with nucleophiles were catalyzed by a crosslinked polystyrene-supported ethylenediamine-copper(II) ion complex (Cu en-PS) under toluene/resin two-phase conditions or toluene/ aqueous buffer/resin three-phase conditions.In the two-phase reactions with octylamine, the rate was increased with a decreasing metal content of the resin.The catalytic efficiency was also dependent on other factors, that is, metal ion, ligand structure, and substrate structure.In the three-phase reactions with water, the hydrolysis was very fast when acetate ions were present in the aqueous phase.It has been suggested that the reactions proceed via a substrate-coordinated intermediate complex under both conditions.
