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593-45-3

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593-45-3 Usage

Description

Octadecane is an alkane hydrocarbon that has the molecular formula CH3(CH2)16CH3. It is a straight-chain alkane that carries 18 carbon atoms. Octadecane has a role as a plant metabolite and a bacterial metabolite. It is found in alcoholic beverages, hop oil, aband other plant resources. Octadecane is a colorless liquid that has a fuel-like smell. It is soluble in water, slightly soluble in ethanol and soluble. It is also soluble in acetone, ethyl ether, chloroform, petroleum, ether, and coal tar hydrocarbons.

Chemical Properties

white crystals or powder

Uses

n-octadecane is used as a solvent, a lubricant, transformer oil and an anti-corrosion agent. It is also used in paraffin and as a chemical intermediate in organic synthesis. It plays an important role in pheromones as a chemical messenger. N-Octadecane/ molecular sieve 5A composites find application as thermal storage material.

Definition

ChEBI: A straight-chain alkane carrying 18 carbon atoms.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 472, 1987 DOI: 10.1021/jo00379a037Tetrahedron Letters, 31, p. 5093, 1990 DOI: 10.1016/S0040-4039(00)97814-6

General Description

Colorless liquid.

Reactivity Profile

Saturated aliphatic hydrocarbons, such as Octadecane, may be incompatible with strong oxidizing agents like nitric acid. Charring of the hydrocarbon may occur followed by ignition of unreacted hydrocarbon and other nearby combustibles. In other settings, aliphatic saturated hydrocarbons are mostly unreactive. They are not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents. When heated sufficiently or when ignited in the presence of air, oxygen or strong oxidizing agents, they burn exothermically to produce carbon dioxide and water.

Fire Hazard

Combustible.

Purification Methods

Crystallise it from acetone and distil it from sodium in a vacuum. [Beilstein 1 IV 553.]

Check Digit Verification of cas no

The CAS Registry Mumber 593-45-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 3 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 593-45:
(5*5)+(4*9)+(3*3)+(2*4)+(1*5)=83
83 % 10 = 3
So 593-45-3 is a valid CAS Registry Number.
InChI:InChI=1/C18H38/c1-3-5-7-9-11-13-15-17-18-16-14-12-10-8-6-4-2/h3-18H2,1-2H3

593-45-3 Well-known Company Product Price

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  • Alfa Aesar

  • (31954)  n-Octadecane, 99%   

  • 593-45-3

  • 100g

  • 342.0CNY

  • Detail
  • Alfa Aesar

  • (31954)  n-Octadecane, 99%   

  • 593-45-3

  • 500g

  • 1055.0CNY

  • Detail
  • Alfa Aesar

  • (31954)  n-Octadecane, 99%   

  • 593-45-3

  • 2kg

  • 3220.0CNY

  • Detail
  • Alfa Aesar

  • (44512)  n-Octadecane, 99.5+%   

  • 593-45-3

  • 1g

  • 124.0CNY

  • Detail
  • Alfa Aesar

  • (44512)  n-Octadecane, 99.5+%   

  • 593-45-3

  • 5g

  • 408.0CNY

  • Detail
  • Alfa Aesar

  • (44512)  n-Octadecane, 99.5+%   

  • 593-45-3

  • 25g

  • 1596.0CNY

  • Detail
  • Alfa Aesar

  • (44301)  n-Octadecane, tech., 90%   

  • 593-45-3

  • 1kg

  • 550.0CNY

  • Detail
  • Alfa Aesar

  • (44301)  n-Octadecane, tech., 90%   

  • 593-45-3

  • 5kg

  • 2558.0CNY

  • Detail
  • Sigma-Aldrich

  • (74691)  Octadecane  analytical standard

  • 593-45-3

  • 74691-1G

  • 208.26CNY

  • Detail
  • Sigma-Aldrich

  • (74691)  Octadecane  analytical standard

  • 593-45-3

  • 74691-5G

  • 590.85CNY

  • Detail
  • Aldrich

  • (O652)  Octadecane  99%

  • 593-45-3

  • O652-25G

  • 533.52CNY

  • Detail
  • Aldrich

  • (O652)  Octadecane  99%

  • 593-45-3

  • O652-100G

  • 848.25CNY

  • Detail

593-45-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name octadecane

1.2 Other means of identification

Product number -
Other names Octadecane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Adsorbents and absorbents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:593-45-3 SDS

593-45-3Synthetic route

octadec-1-ene
112-88-9

octadec-1-ene

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With fac-[Mn(1,2-bis(di-isopropylphosphino)ethane)(CO)3(CH2CH2CH3)]; hydrogen In diethyl ether at 25℃; under 37503.8 Torr; for 18h;99%
With platinum(IV) oxide under 2206.5 Torr; Hydrogenation;
With triethylsilane; palladium dichloride In ethanol at 20℃; for 24h;96 % Chromat.
n-octadecyl isocyanide
76695-50-6

n-octadecyl isocyanide

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With perhydrodibenzo-18-crown-6; potassium; toluene Ambient temperature;99%
With perhydrodibenzo-18-crown-6; potassium; toluene Product distribution; Ambient temperature;99%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In xylene Heating;81%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In xylene Product distribution; Heating; other isocyanides and isothiocyanates, various reduction reagents under different reaction conditions;81%
1-decanoic acid
334-48-5

1-decanoic acid

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With piperidine; silica gel In methanol; acetonitrile Kolbe electrolytic synthesis; Electrolysis; cooling;99%
With potassium hydroxide In methanol at 20℃; for 0.166667h; pH=6; Kolbe Electrolysis;
Elaidic Acid
112-79-8

Elaidic Acid

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With hydrogen In neat (no solvent) at 250℃; under 6000.6 Torr; for 24h; Catalytic behavior; Autoclave; High pressure;99%
stearic acid
57-11-4

stearic acid

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With hydrogen In hexane at 160℃; under 22502.3 Torr; for 18h; Molecular sieve; chemoselective reaction;98%
With hydrogen In neat (no solvent) at 250℃; under 6000.6 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Autoclave; High pressure;96%
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃;94%
Methyl stearate
112-61-8

Methyl stearate

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃;98%
Stage #1: Methyl stearate With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 20h;
Stage #2: In ethanol for 7h; Heating; Further stages.;
96%
With tris(pentafluorophenyl)borate In cyclohexane at 20℃; for 6h; Schlenk technique; Inert atmosphere; Green chemistry;81%
With hydrogen In hexane at 260℃; under 18751.9 Torr; Autoclave;
With hydrogen In cyclohexane at 179.84℃; under 15001.5 Torr; for 3h; Sealed tube;
1-Bromooctadecane
112-89-0

1-Bromooctadecane

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); sodium cyanoborohydride In acetonitrile; tert-butyl alcohol for 3h; Heating;97%
With triethylsilane; dilauryl peroxide; 2,3,3,4,4,5-hexamethyl-2-hexanethiol In cyclohexane for 1h; Heating;89%
With sodium tetrahydroborate; 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; tributyltin chloride In toluene at 110℃; for 36h; Product distribution; Rate constant; other alkyl and aryl halides; other catalysts; also without cocatalyst or phase-transfer catalysts;80%
With sodium tetrahydroborate; 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; tributyltin chloride In toluene at 110℃; for 36h;80%
With sodium tetrahydroborate; 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; tributyltin chloride In toluene at 110℃; Rate constant;
N-nonadecyl nitrile
28623-46-3

N-nonadecyl nitrile

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With potassium; toluene; perhydrodibenzo-18-crown-6 Ambient temperature;95.7%
glycerol tristearate
555-43-1

glycerol tristearate

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With hydrogen In neat (no solvent) at 250℃; under 6000.6 Torr; for 24h; Catalytic behavior; Autoclave; High pressure;93%
With tris(pentafluorophenyl)borate In cyclohexane at 20℃; for 6h; Catalytic behavior; Time; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; Green chemistry;91%
With hydrogen In cyclohexane at 170℃; under 18751.9 Torr; for 24h; Autoclave; Sealed tube;
With hydrogen In neat (no solvent) at 250℃; under 37503.8 Torr; for 48h; Catalytic behavior; Autoclave;89 %Chromat.
Multi-step reaction with 2 steps
1: sodium hydroxide / ethanol / 1 h / Reflux
2: hydrogen / neat (no solvent) / 48 h / 230 °C / 37503.8 Torr / Autoclave
View Scheme
9-hexyl-9-borabicyclo[3.3.1]nonane
42371-64-2

9-hexyl-9-borabicyclo[3.3.1]nonane

1-dodecylbromide
143-15-7

1-dodecylbromide

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With potassium phosphate; tricyclohexylphosphine; palladium diacetate In tetrahydrofuran at 20℃; for 24h; Suzuki cross-coupling;92%
With palladium diacetate; potassium phosphate; 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane In tetrahydrofuran at 20℃; for 24h; Suzuki coupling;236 mg
octadecyl adamantane-1-carboxylate

octadecyl adamantane-1-carboxylate

A

1-octadecanol
112-92-5

1-octadecanol

B

octadecane
593-45-3

octadecane

C

1-Adamantanecarboxylic acid
828-51-3

1-Adamantanecarboxylic acid

Conditions
ConditionsYield
With 18-crown-6 ether; tert-butylamine In diethyl etherA 53%
B 40%
C 90%
1-octadecanol
112-92-5

1-octadecanol

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With hydrogen In decane at 180℃; under 30003 Torr; for 2.5h; Autoclave;88.26%
With n-butylsilane; tris(pentafluorophenyl)borate In dichloromethane91 % Chromat.
Multi-step reaction with 2 steps
1: 88.8 percent / pyridine / N-hydroxysuccinimide / benzene / 2 h / Ambient temperature
2: 87 percent Chromat. / diphenylsilane, benzoyl peroxide / toluene / 0.5 h / Heating
View Scheme
octadecyl (4-fluorophenyl)thionocarbonate
130534-86-0

octadecyl (4-fluorophenyl)thionocarbonate

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With diphenylsilane; triethyl borane; oxygen In benzene at 80℃; for 0.5h;87%
With triethyl borane; diphenylsilane; oxygen In hexane; benzene at 80℃; for 0.5h;87%
With 2,2'-azobis(isobutyronitrile); phenylsilane In toluene for 1.66667h;100 % Spectr.
1-(NN-diethylaminothiocarbonyloxy)octadecane
73532-45-3

1-(NN-diethylaminothiocarbonyloxy)octadecane

A

1-octadecanol
112-92-5

1-octadecanol

B

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With 18-crown-6 ether; tert-butylamine In tetrahydrofuranA 12%
B 87%
With 18-crown-6 ether; tert-butylamine In tetrahydrofuran Ambient temperature;A 12%
B 87%
Octadecanethiol
2885-00-9

Octadecanethiol

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With molybdenum hexacarbonyl In acetone at 120℃; for 6h; Inert atmosphere;85%
O-Octadecyl thiobenzoate
57701-11-8

O-Octadecyl thiobenzoate

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With tri-n-butyl-tin hydride In xylene at 130℃; for 9h;84%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

A

hepatdecane
629-78-7

hepatdecane

B

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With hydrogen In hexane at 290℃; under 22502.3 Torr; for 6h; Temperature;A 12%
B 83%
With 1 wt percent Pt/cobalt-based zeolitic imidazolate framework-67/zeolite 5A at 320℃; under 15001.5 Torr; for 2h; Reagent/catalyst; Temperature; Pressure;
With 1 wt percent Pt/cobalt-based zeolitic imidazolate framework-8/zeolite 5A at 320℃; under 15001.5 Torr; for 2h;
With hydrogen In dodecane at 280℃; under 30003 Torr; for 8h; Autoclave;A 71.8 %Chromat.
B 21.9%Chromat.
1-(n-octadecyloxythiocarbonyl)imidazole
57700-99-9

1-(n-octadecyloxythiocarbonyl)imidazole

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With tri-n-butyl-tin hydride In xylene at 130℃; for 9h;81%
1-isothiocyanatooctadecane
2877-26-1

1-isothiocyanatooctadecane

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In xylene Heating;80%
O-(octadecyl)-S-methyl dithiocarbonate
62008-63-3

O-(octadecyl)-S-methyl dithiocarbonate

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With triethylsilane; bis(1-methyl-1-phenylethyl)peroxide; 2,3,3,4,4,5-hexamethyl-2-hexanethiol In octane for 4h; Heating; also with Prn3SiH; other solvents;80%
With triethylsilane; 2,3,3,4,4,5-hexamethyl-2-hexanethiol; bis(1-methyl-1-phenylethyl)peroxide In octane for 4h; Mechanism; Product distribution; Heating;80%
With tri-n-butyl-tin hydride In various solvent(s) at 150℃; for 9h;71%
With tri-n-butyl-tin hydride In various solvent(s) at 150℃; for 9h; Mechanism; other reaction partner, temperature, solvent and time;71%
1,3-dioxoisoindolin-2-yl stearate
68792-54-1

1,3-dioxoisoindolin-2-yl stearate

trimethylaluminum
75-24-1

trimethylaluminum

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With 1,6-bis(diphenylphosphino)hexane; cobalt(II) bromide In hexane; N,N-dimethyl-formamide at 20℃; for 12h; Schlenk technique; Inert atmosphere;79%
octadecyl adamantane-1-carboxylate

octadecyl adamantane-1-carboxylate

A

1-octadecanol
112-92-5

1-octadecanol

B

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With sodium-potassium alloy; 18-crown-6 ether; tert-butylamine further reagent;A 24%
B 74%
stearic acid
57-11-4

stearic acid

A

1-octadecanol
112-92-5

1-octadecanol

B

hepatdecane
629-78-7

hepatdecane

C

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With hydrogen In decane at 160℃; under 30003 Torr; for 4h; Temperature; Autoclave;A n/a
B n/a
C 68.39%
With hydrogen In dodecane at 289.84℃; under 6000.6 Torr; for 4h; Autoclave;
With hydrogen In cyclohexane at 179.84℃; under 15001.5 Torr; for 1h; Reagent/catalyst; Pressure; Sealed tube;
6-Nitro-7-octadecanone (p-tolylsulfonyl)hydrazone
128802-33-5

6-Nitro-7-octadecanone (p-tolylsulfonyl)hydrazone

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; for 10h;68%
Thiocarbonic acid O-octadecyl ester O-phenyl ester

Thiocarbonic acid O-octadecyl ester O-phenyl ester

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); TMSO-(SiHMeO)n-TMS; bis(tri-n-butyltin)oxide; butan-1-ol In toluene Heating;66%
hexylboronic acid
16343-08-1

hexylboronic acid

1-dodecylbromide
143-15-7

1-dodecylbromide

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With palladium diacetate; methyldi-t-butylphosphine; potassium tert-butylate In tert-Amyl alcohol at 20℃; for 24h; Suzuki cross-coupling;66%
stearic acid
57-11-4

stearic acid

A

hepatdecane
629-78-7

hepatdecane

B

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With hydrogen In dodecane at 260℃; under 30003 Torr; for 1h; Catalytic behavior; Reagent/catalyst;A 9%
B 65%
With hydrogen In decane at 200℃; under 30003 Torr; for 4h; Autoclave;A 13.72%
B n/a
With hydrogen In dodecane at 260℃; under 30003 Torr; Reagent/catalyst; Inert atmosphere; Autoclave;
Indole-3-propionic acid
830-96-6

Indole-3-propionic acid

1-decanoic acid
334-48-5

1-decanoic acid

A

octadecane
593-45-3

octadecane

B

3-undecyl-1H-indole

3-undecyl-1H-indole

C

C20H20N2

C20H20N2

Conditions
ConditionsYield
With sodium methylate In methanol at 0℃; anodic oxidation at Pt/C electrode;A 19%
B 56%
C 14%
1-dodecylbromide
143-15-7

1-dodecylbromide

(1s,5s)-9-hexyl-9-borabicyclo[3.3.1]nonane

(1s,5s)-9-hexyl-9-borabicyclo[3.3.1]nonane

octadecane
593-45-3

octadecane

Conditions
ConditionsYield
With potassium tert-butylate; silver trifluoromethanesulfonate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 40℃; for 24h; Suzuki-Miyaura cross-coupling reaction;56%

593-45-3Relevant articles and documents

Importance of size and distribution of Ni nanoparticles for the hydrodeoxygenation of microalgae oil

Song, Wenji,Zhao, Chen,Lercher, Johannes A.

, p. 9833 - 9842 (2013)

Improved synthetic approaches for preparing small-sized Ni nanoparticles (d=3 nm) supported on HBEA zeolite have been explored and compared with the traditional impregnation method. The formation of surface nickel silicate/aluminate involved in the two pr

One-pot synthesized hierarchical zeolite supported metal nanoparticles for highly efficient biomass conversion

Wang, Darui,Ma, Bing,Wang, Bo,Zhao, Chen,Wu, Peng

, p. 15102 - 15105 (2015)

Hierarchically porous zeolite supported metal nanoparticles are successfully prepared through a base-assisted chemoselective interaction between the silicon species on the zeolite crystal surface and metal salts, in which in situ construction of mesopores and high dispersion of metal species are realized simultaneously.

Nanocomposite Hydrogel of Pd@ZIF-8 and Laponite: Size-Selective Hydrogenation Catalyst under Mild Conditions

Sutar, Papri,Bakuru, Vasudeva Rao,Yadav, Pooja,Laha, Subhajit,Kalidindi, Suresh Babu,Maji, Tapas Kumar

supporting information, p. 3268 - 3272 (2021/01/21)

The composite hydrogel of a nanoscale metal–organic framework (NMOF) and nanoclay has emerged as a new soft-material with advanced properties and applications. Herein, we report a facile synthesis of a hydrogel nanocomposite by charge-assisted self-assembly of Pd@ZIF-8 nanoparticles with Laponite nanoclay which coat the surface of Pd@ZIF-8 nanoparticles. Such surface coating significantly enhanced the thermal stability of the ZIF-8 compared to the pristine framework. Further, the Pd@ZIF-8+LP hydrogel nanocomposite shows better size-selective catalytic hydrogenation of olefins than Pd@ZIF-8 nanoparticles based on selective diffusion of the substrate.

Light-Driven Enzymatic Decarboxylation of Dicarboxylic Acids

Chen, Bi-Shuang,Liu, Lan,Zeng, Yong-Yi,Zhang, Wuyuan

, p. 553 - 559 (2021/06/25)

Photodecarboxylase from Chlorella variabillis (CvFAP) is one of the three known light-activated enzymes that catalyzes the decarboxylation of fatty acids into the corresponding C1-shortened alkanes. Although the substrate scope of CvFAP has been altered by protein engineering and decoy molecules, it is still limited to mono-fatty acids. Our studies demonstrate for the first time that long chain dicarboxylic acids can be converted by CvFAP. Notably, the conversion of dicarboxylic acids to alkanes still represents a chemically very challenging reaction. Herein, the light-driven enzymatic decarboxylation of dicarboxylic acids to the corresponding (C2-shortened) alkanes using CvFAP is described. A series of dicarboxylic acids is decarboxylated into alkanes in good yields by means of this approach, even for the preparative scales. Reaction pathway studies show that mono-fatty acids are formed as the intermediate products before the final release of C2-shortened alkanes. In addition, the thermostability, storage stability, and recyclability of CvFAP for decarboxylation of dicarboxylic acids are well evaluated. These results represent an advancement over the current state-of-the-art.

An unconventional DCOx favored Co/N-C catalyst for efficient conversion of fatty acids and esters to liquid alkanes

Li, Jiang,Liu, Jiaxing,Zhang, Junjie,Wan, Tong,Huang, Lei,Wang, Xintian,Pan, Runze,An, Zhidong,Vlachos, Dionisios G.

, (2019/12/26)

Cobalt (Co) catalysis has recently attracted significant attention in the field of biomass conversion. However, the fabrication of highly dispersive Co nanoparticles at high metal loading with selective facet exposure to achieve specific selectivity is still questionable. In this work, a nitrogen-doped carbon-supported Co catalyst is fabricated for efficient conversion of fatty acids and esters to liquid alkanes. Nitrogen-doping facilitates a highly uniform dispersion of Co nanoparticles even at a high Co loading of 10 wt% and after recycling for 5 runs. The Co/N-C catalyst affords an unconventional decarbonylation/decarboxylation (DCOx) dominant selectivity probably due to partial reduction of cobalt oxides to α-Co0 with only exposure of the (111) facet. Co-existence of Co and N-C leads to strong Lewis acidity and basicity, facilitating the interaction between catalyst and –COOH group, and some important acid-catalyzed step-reactions. The versatility of the Co/N-C catalyst is demonstrated through conversion of various fatty acids and esters.

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