502-73-8

Basic information

• Product Name: 16-HENTRIACONTANONE
• Synonyms: DI-N-PENTADECYL KETONE;16-HENTRIACONTANONE;PALMITONE;Dipentadecyl ketone;hentriacontan-16-one;Pentadecyl ketone;hentricontan-16-one;16-HENTRIACONTANONE 90+%
• CAS NO: 502-73-8
• Molecular Formula: C₃₁H₆₂O
• Molecular Weight: 450.82
• EINECS: 207-952-8
• Mol File: 502-73-8.mol
• Article Data: 19

Chemical Properties

• Melting Point: 84 °C
• Boiling Point: 483.81°C (rough estimate)
• Flash Point: 35.6°C
• Appearance: /
• Density: 0.8674 (rough estimate)
• Vapor Pressure: 4.14E-10mmHg at 25°C
• Refractive Index: 1.4901 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly)
• CAS DataBase Reference: 16-HENTRIACONTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 16-HENTRIACONTANONE(502-73-8)
• EPA Substance Registry System: 16-HENTRIACONTANONE(502-73-8)

Safety Data

• Hazardous Substances Data: 502-73-8(Hazardous Substances Data)

Usage

Definition

ChEBI: A dialkyl ketone that is hentriacontane in which the hydrogens at position 16 are replaced by an oxo group.

InChI:InChI=1/C31H62O/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31(32)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-30H2,1-2H3

Synthetic route

methyl α-palmitoyl palmitate (60715-65-3) → palmitone (502-73-8)

Conditions	Yield
With sodio-propane-1,2-diol in anhydrous propane-1,2-diol at 80 - 85℃; for 0.5h;	96%

TREHALOSE (99-20-7) + methyl α-palmitoyl palmitate (60715-65-3) → palmitone (502-73-8) + 6-O-(palmitoyl)-α,α-D-trehalose (42939-93-5)

Conditions	Yield
potassium carbonate In N,N-dimethyl-formamide at 80℃; under 80 Torr; for 6h;	A 5% B 95%

α-Tetradecyl-β-keto-stearinsaeureethylester (119119-53-8) → palmitone (502-73-8)

Conditions	Yield
With potassium hydroxide; ethanol for 15h; Reflux; Inert atmosphere;	83%

1-hexadecylcarboxylic acid (57-10-3) → palmitone (502-73-8)

Conditions	Yield
manganese(IV) oxide at 300℃; for 4h; Product distribution / selectivity; Sealed tube; Inert atmosphere;	44.5%
With iron at 295℃;
With iron

TREHALOSE (99-20-7) + methyl α-palmitoyl palmitate (60715-65-3) → palmitone (502-73-8) + 3-Oxo-2-tetradecyl-octadecanoic acid (2R,3S,4R,5R,6R)-4,5-dihydroxy-2-hydroxymethyl-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxymethyl ester + 6-O-(palmitoyl)-α,α-D-trehalose (42939-93-5)

Conditions	Yield
sodium carbonate for 96h;	A n/a B 40% C n/a

β,β-trehalose (499-23-0) + methyl α-palmitoyl palmitate (60715-65-3) → palmitone (502-73-8) + 3-Oxo-2-tetradecyl-octadecanoic acid (2R,3S,4R,5R,6S)-4,5-dihydroxy-2-hydroxymethyl-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxymethyl ester + Hexadecanoic acid (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (76054-91-6)

Conditions	Yield
potassium carbonate In N,N-dimethyl-formamide at 80℃; under 80 Torr;	A 16% B 37% C 2%
sodium carbonate In N,N-dimethyl-formamide at 80℃; under 80 Torr; for 6h;	A 16% B 37% C 2%
potassium carbonate In N,N-dimethyl-formamide at 80℃; under 80 Torr; for 6h;	A 16% B 37% C 2%

1-hexadecylcarboxylic acid (57-10-3) → pentadecane (629-62-9) + palmitone (502-73-8)

Conditions	Yield
5% rhenium on carbon at 300℃; for 4h; Product distribution / selectivity; Sealed vial; Inert atmosphere;	A 26.7% B 5.2%

hexadecanoic acid methyl ester (112-39-0) → palmitone (502-73-8)

Conditions	Yield
With tert-butylmagnesium chloride; xylene at 110 - 120℃;
With tert-butylmagnesium chloride; toluene at 110 - 120℃;
With titanium(IV) oxide at 360℃; under 15001.5 Torr; for 4h;

sodium palmitate (408-35-5) → palmitone (502-73-8)

Conditions	Yield
at 400 - 450℃; bei der Destillation;

1-hexadecylcarboxylic acid (57-10-3) → hentriacontane (630-04-6) + palmitone (502-73-8)

Conditions	Yield
With nickel-copper-hydroxide at 300 - 400℃; mit japanischen saurem Ton;

hexadecanoic acid ethyl ester (628-97-7) + tert-butylmagnesium chloride (677-22-5) + toluene (108-88-3) → palmitone (502-73-8)

Conditions	Yield
at 110 - 120℃;

TREHALOSE (99-20-7) + methyl α-palmitoyl palmitate (60715-65-3) → palmitone (502-73-8)

Conditions	Yield
With dicyclohexyl-18-crown-5; potassium carbonate
caesium carbonate

nickel palmitate → palmitone (502-73-8)

Conditions	Yield
Heating;

manganese palmitate → palmitone (502-73-8)

Conditions	Yield
Heating;

1-hexadecylcarboxylic acid (57-10-3) + iron → palmitone (502-73-8)

Conditions	Yield
at 295℃;

1-hexadecylcarboxylic acid (57-10-3) + phosphoric acid anhydride → palmitone (502-73-8)

Conditions	Yield
at 200 - 210℃;

1-hexadecylcarboxylic acid (57-10-3) + thorium oxide → palmitone (502-73-8)

Conditions	Yield
at 400 - 430℃;

1-hexadecylcarboxylic acid (57-10-3) → palmitone (502-73-8) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + carbon monoxide

Conditions	Yield
at 380 - 540℃; Reaktion des Natriumsalzes; bei der Destillation aus einem Aluminiumgefaess;

1-hexadecylcarboxylic acid (57-10-3) + nickel-copper-hydroxide + fired clay → palmitone (502-73-8) + hentriacontane (?)

Conditions	Yield
at 300 - 400℃;

2-palmitoyl-palmitic acid ethyl ester → palmitone (502-73-8)

Conditions	Yield
With potassium hydroxide Hydrolysis;
With potassium hydroxide Hydrolysis;

calcium palmitate → palmitone (502-73-8)

Conditions	Yield
Pyrolysis;

1-Hexadecanol (36653-82-4) + sodium → 2-tetradecyl-octadecanol (32582-32-4) + palmitone (502-73-8) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
at 300℃;

calcium Palmitate (542-42-7) → palmitone (502-73-8) + CO2, CaCO3

Conditions	Yield
Thermodynamic data; thermogravimetric analysis; constant rate of heating (20 degC/min);

magnesium Palmitate (2601-98-1) → palmitone (502-73-8)

Conditions	Yield
Heating; Inert atmosphere;

S-palmitoyl-coenzyme A (1763-10-6) → palmitone (502-73-8) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
With OleA from Xanthomonas campestris spv. campestris str. ATCC 33913 at 20℃; for 0.0833333h; pH=7.4; Claisen condensation; aq. buffer; Enzymatic reaction;

S-palmitoyl-coenzyme A (1763-10-6) + decanoyl coenzyme A (1264-57-9) → 1-decanoic acid (334-48-5) + 10-Nonadecanon (504-57-4) + palmitone (502-73-8) + Nonyl-pentadecyl-keton (31469-37-1) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
With OleA from Xanthomonas campestris spv. campestris str. ATCC 33913 at 20℃; for 0.0833333h; pH=7.4; Claisen condensation; aq. buffer; Enzymatic reaction;

S-palmitoyl-coenzyme A (1763-10-6) + lauroyl coenzyme A → lauric acid (143-07-7) + laurone (540-09-0) + palmitone (502-73-8) + Undecyl-pentadecyl-keton (31534-85-7) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
With OleA from Xanthomonas campestris spv. campestris str. ATCC 33913 at 20℃; for 0.0833333h; pH=7.4; Claisen condensation; aq. buffer; Enzymatic reaction;

S-palmitoyl-coenzyme A (1763-10-6) + myristoyl-coenzyme A → heptacosan-14-one (542-50-7) + nonacosan-14-one (34394-11-1) + palmitone (502-73-8) + n-tetradecanoic acid (544-63-8) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
With OleA from Xanthomonas campestris spv. campestris str. ATCC 33913 at 20℃; for 0.0833333h; pH=7.4; Claisen condensation; aq. buffer; Enzymatic reaction;

1-hexadecylcarboxylic acid (57-10-3) → heptadecan-2-one (2922-51-2) + palmitone (502-73-8)

Conditions	Yield
With K0.8Zn0.4Ti1.6O4 In para-xylene at 375℃; under 760.051 Torr; for 6h; Reagent/catalyst; Flow reactor; Inert atmosphere; Gas phase;

palmitone (502-73-8) → 16-hentriacontanol (1070-54-8)

Conditions	Yield
With 5% active carbon-supported ruthenium; hydrogen In water; toluene at 100 - 150℃; under 15001.5 Torr; for 6h; Autoclave; Inert atmosphere;	90%
With kieselguhr; nickel at 100℃; Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether

palmitone (502-73-8) → palmitic acid pentadecyl ester (18299-77-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In water at 80℃; for 0.5h;	85%

palmitone (502-73-8) + salicylamide (65-45-2) → 2,3-dihydro-2,2-dipentadecanyl-4H-1,3-benzoxazin-4-one (158299-37-7)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 8h; Heating;	85%

palmitone (502-73-8) + malonic acid dimethyl ester (108-59-8) → C36H68O4

Conditions	Yield
Stage #1: malonic acid dimethyl ester With tetrahydrofuran; titanium tetrachloride In chloroform at 5 - 20℃; for 1h; Knoevenagel Condensation; Inert atmosphere; Stage #2: With pyridine In chloroform at 0 - 20℃; for 0.333333h; Inert atmosphere; Stage #3: palmitone In chloroform at 20 - 35℃; Knoevenagel Condensation; Inert atmosphere;	79%

palmitone (502-73-8) + 5-Methyluridine (1463-10-1) → 1-[(3aR,4R,6R,6aR)-tetrahydro-6-(hydroxymethyl)-2,2-dipentadecylfuro[3,4-d] [1,3]dioxol-4-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (1440632-45-0)

Conditions	Yield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran at 75℃; for 24h;	74%
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran at 75℃; for 24h;	74%
Stage #1: palmitone; 5-Methyluridine With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran at 75℃; for 24h; Stage #2: With sodium hydrogencarbonate; triethylamine In tetrahydrofuran; water at 20℃; for 0.25h; Cooling with ice;	74%

palmitone (502-73-8) + uridine (58-96-8) → 1-[(3aR,4R,6R,6aR)-tetrahydro-6-(hydroxymethyl)-2,2-dipentadecylfuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4(1H,3H)-dione (1078143-02-8)

Conditions	Yield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran for 24h; Reflux;	62%
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran at 75℃; for 24h;	53.7%
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran at 75℃; for 24h;	53.7%

methanol (67-56-1) + palmitone (502-73-8) → 16,16-dimethoxy-hentriacontane (1078143-04-0)

Conditions	Yield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran for 2h; Reflux; Inert atmosphere;	49%

palmitone (502-73-8) + 5-fluorouridine (316-46-1) → 5-fluoro-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dipentadecanyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)dione (1581758-38-4)

Conditions	Yield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran for 25h; Reflux;	49%
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran for 24h; Reflux;	49%

palmitone (502-73-8) + uridine (58-96-8) → 2',3'-O-16-hentriacontanyliden-uridine

Conditions	Yield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In tetrahydrofuran for 24h; Reflux;	49%

3-Amino-1,2-propanediol (616-30-8, 13552-31-3) + palmitone (502-73-8) → C34H71NO2

Conditions	Yield
Stage #1: 3-Amino-1,2-propanediol; palmitone With titanium(IV) tetraethanolate In methanol; chloroform at 65℃; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol; chloroform at 40℃; for 3h; Inert atmosphere;	49%

palmitone (502-73-8) + dimethyl amine (124-40-3) → C33H69N

Conditions	Yield
Stage #1: palmitone; dimethyl amine With titanium(IV) tetraethanolate In tetrahydrofuran at 20℃; for 20h; Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at 20℃; for 4h; Stage #3: With methanol; 3% Pd/C In tetrahydrofuran at 20℃;	44%

palmitone (502-73-8) + N,N-bis-(3-dimethylaminopropyl)amine (6711-48-4) → C41H87N3

Conditions	Yield
Stage #1: palmitone; N,N-bis-(3-dimethylaminopropyl)amine With titanium(IV) isopropylate In tetrahydrofuran at 65℃; for 72h; Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at 20℃; for 4h;	32%

n-butyl magnesium bromide (693-03-8) + diethyl ether (60-29-7) + palmitone (502-73-8) → hentriacontane (630-04-6) + 16-hentriacontanol (1070-54-8) + 16-butyl-hentriacontan-16-ol (124115-30-6)

n-butyl magnesium bromide (693-03-8) + palmitone (502-73-8) → 16-butyl-hentriacontan-16-ol (124115-30-6)

Conditions	Yield
With diethyl ether

palmitone (502-73-8) + methylmagnesium bromide (75-16-1) → 16-methyl-hentriacontan-16-ol (122338-07-2)

Conditions	Yield
With diethyl ether

palmitone (502-73-8) + ethylmagnesium bromide (925-90-6) → 3-pentadecyl-octadec-2-ene

Conditions	Yield
With diethyl ether anschliessend Destillieren des Reaktionsprodukts unter vermindertem Druck;

palmitone (502-73-8) + ethylmagnesium bromide (925-90-6) → 16-ethyl-hentriacontan-16-ol

Conditions	Yield
With diethyl ether

palmitone (502-73-8) + n-propylmagnesium bromide (927-77-5) → 16-propyl-hentriacontan-16-ol (120831-04-1)

Conditions	Yield
With diethyl ether

palmitone (502-73-8) + n-pentylmagnesium bromide (693-25-4) → 16-pentyl-hentriacontan-16-ol (121498-77-9)

Conditions	Yield
With diethyl ether

palmitone (502-73-8) + sodium acetylide (1066-26-8) → 3-pentadecyl-octadec-1-yn-3-ol (121143-90-6)

Conditions	Yield
With diethyl ether; ammonia

palmitone (502-73-8) → hentriacontane (630-04-6)

Conditions	Yield
With hydrazine hydrate; diethylene glycol
With hydrazine hydrate; ethylene glycol
With amalgamated zinc in wss.-aethanol. HCl;

Upstream product

• 57-10-3 1-hexadecylcarboxylic acid 
• 499-23-0 β,β-trehalose 
• 60715-65-3 methyl α-palmitoyl palmitate 
• 36653-82-4 1-Hexadecanol 
• 142-62-1 hexanoic acid 
• 628-97-7 hexadecanoic acid ethyl ester 
• 65-85-0 benzoic acid 
• 112-39-0 hexadecanoic acid methyl ester 
• 1763-10-6 S-palmitoyl-coenzyme A 
• 1264-57-9 decanoyl coenzyme A 
• 2601-98-1 magnesium Palmitate 
• 119119-53-8 α-Tetradecyl-β-keto-stearinsaeureethylester 
• 542-42-7 calcium Palmitate 
• 99-20-7 TREHALOSE 

Downstream Products

• 630-04-6 hentriacontane 
• 1070-54-8 16-hentriacontanol 
• 124115-30-6 16-butyl-hentriacontan-16-ol 
• 112-41-4 1-dodecene 
• 2922-51-2 heptadecan-2-one 
• 1120-36-1 1-tetradecene 
• 112-39-0 hexadecanoic acid methyl ester 
• 64-19-7 acetic acid 
• 107-92-6 butyric acid 
• 1070-06-0 hentriacontan-16-one oxime 

Relevant articles and documents

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Physico-chemical studies on calcium soaps

Calcium soaps were prepared by the metathesis of the corresponding potassium soap with an aqueous solution of calcium acetate.The IR results showed that the fatty acids exist in a dimeric structure as a result of hydrogen bonding between the carbonyl groups of two acid molecules, whereas calcium palmitate has an ionic character.The X-ray analysis indicated that the zig-zag chains of the fatty acid radical constituent of the soap molecules extend straigthforward on both sides of each basal plane and that the molecular axes of the soaps are slightly inclined to the basal plane.The thermal decomposition of calcium palmitate was found to be kinetically of zero order and the energy of activation for the decomposition was in the region of 3 KJ/mole.

METHOD FOR PRODUCING HIGHER LINEAR FATTY ACIDS OR ESTERS

The present invention relates to a method of producing linear fatty acids comprising 7 to 28 carbon atoms or esters thereof using a combined biotechnological and chemical method. In particular, the present invention relates to a method of producing dodecanoic acid (i.e. lauric acid), via higher alkanones, preferably 6-undecanone.

PROCESS FOR PRODUCING RENEWABLE PRODUCTS

The present invention relates to a method for producing renewable ketones, paraffin waxes, base oil components and alkenes from a feedstock of biological origin, wherein the method includes ketonisation of esters of fatty acids and monohydric alcohols wherein the alcohols have carbon chain length of two or more.