110-41-8 Usage
Description
2-Methylundecanal has a characteristic fatty odor assuming a floral
note on dilution. It has an acrid, fatty unpleasant flavor at high
levels. At low levels, the flavor is honey- and nut-like. It may be
prepared by cracking the corresponding glycidic acid; from
α-nonyl acrolein; from methyl nonyl ketone and ethyl monochloroacetate
in the presence of sodium ethylate.
Chemical Properties
Different sources of media describe the Chemical Properties of 110-41-8 differently. You can refer to the following data:
1. 2-Methylundecanal has a characteristic fatty odor assuming a floral note on dilution. At high levels, it has an acrid, fatty,
unpleasant flavor. At low levels, the flavor is honey and nut-like.
2. clear colourless to yellowish liquid
Occurrence
Reported found in kumquat peel oil.
Uses
Perfumery, flavoring.
Preparation
2-Methylundecanal is reported as being
found in nature. It is a colorless liquid, with an odor markedly different from that
of the isomeric dodecanal. It has a fatty odor with incense and ambergris notes.
2-Methylundecanal is produced by two routes:
1) 2-Undecanone is converted into its glycidate by reaction with an alkyl
chloroacetate. Saponification of the glycidate, followed by decarboxylation,
yields 2-methylundecanal.
2) The second synthesis is based on the conversion of undecanal into 2-
methyleneundecanal by reaction with formaldehyde in the presence of
catalytic amounts of amines. Hydrogenation of 2-methyleneundecanal
yields methylnonylacetaldehyde (MNA). A convenient process starts
from 1-decene: hydroformylation gives a mixture consisting mainly of
undecanal and 2-methyldecanal. Reaction of the crude product with
formaldehyde in the presence of dibutylamine yields a mixture containing
over 50% 2-methyleneundecanal. After hydrogenation of the double bond,
pure 2-methylundecanal is separated from the by-products by fractional
distillation.
In comparison with other fatty aldehydes, 2-methylundecanal is used in perfumery
in rather large amounts to impart conifer notes, particularly fir impressions,
but frequently also in fantasy compositions.
Taste threshold values
Taste characteristics at 2 ppm: waxy, fatty, metallic with a citrus nuance.
Flammability and Explosibility
Nonflammable
Safety Profile
Low toxicity by
ingestion and skin contact. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Synthesis
By cracking the corresponding glycidic acid; from α-nonyl acrolein; from methyl nonyl ketone and ethyl monochloroacetate in the presence of sodium ethylate
Metabolism
See monograph on aldehyde C-8*.
Check Digit Verification of cas no
The CAS Registry Mumber 110-41-8 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 0 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 110-41:
(5*1)+(4*1)+(3*0)+(2*4)+(1*1)=18
18 % 10 = 8
So 110-41-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H22O/c1-3-4-5-6-7-8-9-10-12(2)11-13/h10-11H,3-9H2,1-2H3
110-41-8Relevant articles and documents
CATALYTIC α-ALKYLATION OF ALDEHYDES WITH OLEFINS
Vinogradov, M. G.,Kovalev, I. P.,Nikishin, G. I.
, p. 1265 - 1271 (1981)
-
Synthesis method of methyl nonyl acetaldehyde
-
Paragraph 0014; 0018; 0019; 0023, (2018/09/08)
The invention provides a synthesis method of methyl nonyl acetaldehyde. The synthesis method comprises the following steps: (a) taking n-undecylic aldehyde and formaldehyde as raw materials and morpholine/acetic acid as a catalyst in a solvent; adding n-undecylic aldehyde into a reaction system in a dropwise adding manner; reacting at 70 to 80 DEG C to generate methylene undecylic aldehyde; (b) taking methylene undecylic aldehyde as a raw material and palladium/carbon as a catalyst, and carrying out hydrogenation reaction to generate methyl nonyl acetaldehyde. The synthesis method of methyl nonyl acetaldehyde has the advantages of moderate reaction conditions, high reaction selectivity and high yield.
Rhodium-catalyzed tandem isomerization/hydroformylation of the bio-sourced 10-undecenenitrile: Selective and productive catalysts for production of polyamide-12 precursor
Ternel, Jeremy,Couturier, Jean-Luc,Dubois, Jean-Luc,Carpentier, Jean-Francois
, p. 3191 - 3204 (2013/12/04)
The hydroformylation of 10-undecenenitrile (1) - a substrate readily prepared from renewable castor oil - in the presence of rhodium-phosphane catalysts systems is reported. The corresponding linear aldehyde (2) can be prepared in high yields and regioselectivities with a (dicarbonyl)rhodium acetoacetonate-biphephos [Rh(acac)(CO)2-biphephos] catalyst. The hydroformylation process is accompanied by isomerization of 1 into internal isomers of undecenenitrile (1-int); yet, it is shown that the Rh-biphephos catalyst effectively isomerizes back 1-int into 1, eventually allowing high conversions of 1/1-int into 2. Recycling of the catalyst by vacuum distillation under a controlled atmosphere was demonstrated over 4-5 runs, leading to high productivities up to 230,000 mol (2)×mol (Rh)-1 and 5,750 mol (2)×mol (biphephos)-1. Attempted recycling of the catalyst using a thermomorphic multicomponent solvent (TMS) phase-separation procedure proved ineffective because the final product 2 and the Rh-biphephos catalyst were always found in the same polar phase. Auto-oxidation of the linear aldehyde 2 into the fatty 10-cyano-2-methyldecanoic acid (5) proceeds readily upon exposure to air at room temperature, opening a new effective entry toward polyamide-12. Copyright
Synthesis of aliphatic aldehydes
Bratulescu, George
experimental part, p. 2233 - 2234 (2012/02/17)
An easy procedure for synthesis of aliphatic aldehydes has been realized in heterogeneous medium from dimethyl sulfoxide, halides and bicarbonate anions. The mixture was irradiated with microwave for a short time and lead to desired products. A number of aliphatic aldehydes were obtained in mild conditions with a good yield.
