540-10-3

Basic information

• Product Name: CETYL PALMITATE
• Synonyms: SPERMACETI;PALMATIC ACID N-HEXADECYL ESTER;SperMwax;Cetyl Palmitate (50 mg);n-Hexadecyl palMitate, 98% 25GR;n-Hexadecyl palMitate, 98% 5GR;Cetyl Palmitate Palmitic Acid Hexadecyl Ester;PalMityl palMitate, 95+%
• CAS NO: 540-10-3
• Molecular Formula: C₃₂H₆₄O₂
• Molecular Weight: 480.85
• EINECS: 208-736-6
• Product Categories: Aliphatics;Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 540-10-3.mol
• Article Data: 21

Chemical Properties

• Melting Point: 55-56 °C(lit.)
• Boiling Point: 360 °C
• Flash Point: 269.8 °C
• Appearance: White to almost white/Crystalline Powder
• Density: d20 0.989
• Refractive Index: 1.4429 (589.3 nm 60℃)
• Storage Temp.: 2-8°C
• Solubility: Soluble in hot acetone.
• Merck: 14,2031
• CAS DataBase Reference: CETYL PALMITATE(CAS DataBase Reference)
• NIST Chemistry Reference: CETYL PALMITATE(540-10-3)
• EPA Substance Registry System: CETYL PALMITATE(540-10-3)

Safety Data

• Safety Statements: 24/25
• RTECS: RT4750000
• TSCA: Yes
• Hazardous Substances Data: 540-10-3(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white crystalline powder

Uses

Different sources of media describe the Uses of 540-10-3 differently. You can refer to the following data:
1. Palmityl Palmitate is a wax ester of palmitic acid used in cosmetic and personal care products.
2. The chemical structure of cetyl palmitate (synthetic spermaceti) is the same as whale spermaceti. It may be used to thicken, produce viscose emulsions, give stability, and add texture to emulsions. It is similar to cetearyl palmitate.
3. It is used as emollients, masking agents and skin conditioning and a glosser and thickener for creams. It improves emulsion texture and stability and gives structure to cosmetic sticks. Used in skin and hair applications.

Definition

ChEBI: A palmitate ester resulting from the formal condensation of palmitic acid with palmityl alcohol. It is used as a thickener and emollient in cosmetics.

General Description

Cetyl Palmitate is an ester of palmitic acid, obtained via the reaction of cetyl alcohol and palmitic acid. It is an ingredient of many cosmetic preparations.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Flammability and Explosibility

Notclassified

InChI:InChI=1S/C32H64O2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-34-32(33)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-31H2,1-2H3

Synthetic route

1-Hexadecanol (36653-82-4) + 1-hexadecylcarboxylic acid (57-10-3) → cetyl palmitate (540-10-3)

Conditions	Yield
With zirconium(IV) oxychloride In 1,3,5-trimethyl-benzene at 162℃; for 24h;	99.5%
hafnium(IV) oxychloride In 1,3,5-trimethyl-benzene at 162℃; for 24h;	98.7%
With choline chloride; zinc(II) chloride at 110℃; for 10h;	97%

1-Hexadecanol (36653-82-4) → cetyl palmitate (540-10-3)

Conditions	Yield
With sodium bromate; sulfuric acid; sodium bromide In water at 20℃; for 24h;	99%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (2-((2-(diphenylphosphanyl)ethyl)(quinolin-2-ylmethyl)amino)ethyl)diphenylphosphine oxide; potassium tert-butylate In n-heptane at 100℃; for 16h;	86%

1-hexadecylcarboxylic acid (57-10-3) → 1-Hexadecanol (36653-82-4) + cetyl palmitate (540-10-3)

Conditions	Yield
With trimethylamine borane In xylene for 9h; Heating;	A 22% B 61%
With hydrogen; zirconium(IV) oxide In dodecane at 20 - 260℃; under 9000.9 Torr; Kinetics; Autoclave;

1-hexadecylcarboxylic acid (57-10-3) → cetyl palmitate (540-10-3)

Conditions	Yield
With hydrogen In neat (no solvent) at 20 - 200℃; under 6000.6 Torr; for 24h; Autoclave; High pressure;	55%
With copper chromite; hydrogen at 360℃;

1-iodohexadecane (544-77-4) + silver palmitate (3508-01-8) → cetyl palmitate (540-10-3)

1-Hexadecanol (36653-82-4) + n-hexadecanoyl chloride (112-67-4) → cetyl palmitate (540-10-3)

Conditions	Yield
With quinoline; chloroform anfangs unter Kuehlung, dann bei Zimmertemperatur;
With diethyl ether; magnesium
With pyridine
In pyridine; chloroform

n-hexadecanoyl chloride (112-67-4) + catyl alcohol → cetyl palmitate (540-10-3)

Conditions	Yield
at 180℃;

1-Hexadecanol (36653-82-4) + n-tetradecanoic acid (544-63-8) + 1-hexadecylcarboxylic acid (57-10-3) → tetradecanoic acid hexadecyl ester (2599-01-1) + cetyl palmitate (540-10-3)

Conditions	Yield
With phosphoric acid In hexane; water for 8.5h; Product distribution / selectivity; Heating / reflux;
With phosphoric acid In n-heptane; water for 18h; Product distribution / selectivity; Heating / reflux;
With phosphoric acid In water; toluene at 92℃; for 38.5h; Product distribution / selectivity; Heating / reflux;
With phosphoric acid In water; xylene at 105℃; for 1h; Product distribution / selectivity;
With phosphoric acid In water at 95℃; for 0.5h; Product distribution / selectivity;

1-hexadecylcarboxylic acid (57-10-3) → pentadecane (629-62-9) + Hexadecane (544-76-3) + 1-Hexadecanol (36653-82-4) + cetyl palmitate (540-10-3)

Conditions	Yield
With hydrogen In dodecane at 20 - 260℃; under 9000.9 Torr; Kinetics; Autoclave;

1-hexadecylcarboxylic acid (57-10-3) → pentadecane (629-62-9) + 1-Hexadecanol (36653-82-4) + cetyl palmitate (540-10-3)

Conditions	Yield
With hydrogen In dodecane at 20 - 260℃; under 9000.9 Torr; Kinetics; Autoclave;
With hydrogen In dodecane at 280℃; under 39003.9 Torr; for 6h; Catalytic behavior; Kinetics; Time;

hexadecanoic acid methyl ester (112-39-0) → 1-Hexadecanol (36653-82-4) + n-hexadecylaldehyde (629-80-1) + palmitone (502-73-8) + cetyl palmitate (540-10-3) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
With hydrogen; zirconium(IV) oxide at 700℃; under 60006 Torr; Kinetics; Reagent/catalyst; Temperature; Pressure; Calcination;

hexadecanoic acid methyl ester (112-39-0) → pentadecane (629-62-9) + methane (34557-54-5) + Hexadecane (544-76-3) + hexadecan-2-ol (14852-31-4) + 1-Hexadecanol (36653-82-4) + n-hexadecylaldehyde (629-80-1) + cetyl palmitate (540-10-3) + carbon dioxide (124-38-9) + carbon monoxide (201230-82-2) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
With hydrogen In dodecane at 290℃; under 22502.3 Torr;

...Expand

hexadecanoic acid methyl ester (112-39-0) → pentadecane (629-62-9) + methane (34557-54-5) + Hexadecane (544-76-3) + hexadecan-2-ol (14852-31-4) + 1-Hexadecanol (36653-82-4) + n-hexadecylaldehyde (629-80-1) + cetyl palmitate (540-10-3) + carbon monoxide (201230-82-2) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
With hydrogen In dodecane at 290℃; under 22502.3 Torr;

...Expand

1-hexadecylcarboxylic acid (57-10-3) → pentadecane (629-62-9) + Hexadecane (544-76-3) + 1-Hexadecanol (36653-82-4) + n-hexadecylaldehyde (629-80-1) + cetyl palmitate (540-10-3)

Conditions	Yield
With hydrogen In dodecane at 280℃; under 39003.9 Torr; for 6h; Kinetics;

1-hexadecylcarboxylic acid (57-10-3) → Hexadecane (544-76-3) + 1-Hexadecanol (36653-82-4) + n-hexadecylaldehyde (629-80-1) + cetyl palmitate (540-10-3)

Conditions	Yield
With hydrogen In dodecane at 280℃; under 39003.9 Torr; for 6h; Kinetics;

cetyl palmitate (540-10-3) → O-hexadecyl hexadecanethiono ester

Conditions	Yield
With Lawessons reagent In 5,5-dimethyl-1,3-cyclohexadiene Reflux;	58%

cetyl palmitate (540-10-3) → n-hexadecylaldehyde (629-80-1)

Conditions	Yield
With dimethylsulfide borane complex; pyridinium chlorochromate 1) THF, reflux, 1 h, 2.) CH2Cl2, reflux, 1 h; Yield given. Multistep reaction;

cetyl palmitate (540-10-3) → <1-14C>n-hexadecanol palmitate

Conditions	Yield
With 1-(14)C cetyl alcohol In acetone at 40℃; for 1h; transesterification with enzyme from Sinapis alba L.;

cetyl palmitate (540-10-3) → <4-14C>cholesteryl palmitate

Conditions	Yield
With [14C]-Cholesterol In acetone at 40℃; for 1h; transesterification with enzyme from Sinapis alba L.; influence of incubation time and <1-14C>n-hexadecanol concentration on ester formation; double pH optima: 6.4, 8.4;

cetyl palmitate (540-10-3) + α-particle/s → hydrogen + carbon oxides + hydrocarbons

Conditions	Yield
Irradiation;

monoglyceryl stearate + cetyl palmitate (540-10-3) → monocetylphosphoric ester potassium salt + acrylic acid (79-10-7)

Upstream product

• 544-77-4 1-iodohexadecane 
• 3508-01-8 silver palmitate 
• 36653-82-4 1-Hexadecanol 
• 544-63-8 n-tetradecanoic acid 
• 57-10-3 1-hexadecylcarboxylic acid 
• 112-39-0 hexadecanoic acid methyl ester 
• 112-67-4 n-hexadecanoyl chloride 

Downstream Products

• 79-10-7 acrylic acid 
• 629-80-1 n-hexadecylaldehyde 

Relevant articles and documents

Esterification of cetyl alcohol with palmitic acid over WO3/Zr-SBA-15 and Zr-SBA-15 catalysts

Tungsten loaded and Zr incorporated SBA-15 catalysts (WO3/Zr-SBA-15 and Zr-SBA-15) were developed for esterification of cetyl alcohol and palmitic acid. The influence of the Zr content, tungsten loading amount, calcination temperature, feed composition and catalyst amount has been studied. Higher tungsten loading decreased the acidity due to formation of WO3 crystals whereas calcination temperature enhanced the acidity by favoring the dispersion of WOx species. Activities of the catalyst changed depending on their amount of Br?nsted sites and total number of acid sites. Zr-SBA-15 catalyst which had the highest amount of Br?nsted acid sites gave maximum cetyl palmitate yield (63.1%). This catalyst retained its activity up to 3 reuse cycles without significant loss of activity.

PRODUCTION METHOD OF ESTER COMPOUND

PROBLEM TO BE SOLVED: To produce an ester compound at a high conversion even under mild reaction conditions. SOLUTION: A production method of an ester compound includes a reaction step for reacting a carboxylic acid of 8-22 carbons and an alcohol of 8-22 carbons at a temperature of 50-100°C in an ionic liquid composed of a phosphonium cation or an imidazolium cation and a trifluoromethanesulfonic acid anion or a bis (trifluoromethanesulfonyl) imide anion to obtain an ester compound in a liquid phase different from an ionic liquid phase. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Aldehyde effect and ligand discovery in Ru-catalyzed dehydrogenative cross-coupling of alcohols to esters

The presence of different aldehydes is found to have a significant influence on the catalytic performance when using PN(H)P type ligands for dehydrogenation of alcohols. Accordingly, hybrid multi-dentate ligands were discovered based on an oxygen-transfer alkylation of PNP ligands by aldehydes. The relevant Ru-PNN(PO) system provided the desired unsymmetrical esters in good yields via acceptorless dehydrogenation of alcohols. Hydrogen bonding interactions between the phosphine oxide moieties and alcohol substrates likely assisted the observed high chemoselectivity.