1,18-octadecanediol Chemical Properties

Melting point:

91°C

Boiling point:

323.59°C (rough estimate)

Density 

0.8738 (rough estimate)

refractive index 

1.4827 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

14.90±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C18H38O2/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20/h19-20H,1-18H2

InChIKey

LUUFSCNUZAYHAT-UHFFFAOYSA-N

SMILES

C(O)CCCCCCCCCCCCCCCCCO

Safety Information

HS Code 

2905.39.9000

1,18-octadecanediol Usage And Synthesis

Uses

Octadecane-1,18-diol is a useful research chemical compound.

Uses

1,18-Octadecanediol (Octadecane-1,18-diol) is a copolymer of long-chain diol monomers that has properties similar to polyethylene while being easily chemically recyclable and biodegradable[1].

Synthesis

The general procedure for the synthesis of 1,18-octadecanediol from dimethyl octadecanedioate was as follows: in a 1000 mL three-necked flask, dimethyl octadecanedioate (14.8 g, 43.1 mmol, 1.0 eq.) was dissolved in 700 mL of anhydrous tetrahydrofuran (THF) and the reaction system cooled down to 0 °C. Subsequently, lithium aluminum hydride (LiAlH4, 4.1 g, 107.8 mmol, 2.5 eq.) was slowly added. The resulting reaction mixture was stirred at room temperature for 1 hour and subsequently heated to reflux for 6 hours. Upon completion of the reaction, the mixture was cooled again to 0 °C and the reaction was quenched by slow addition of a pre-cooled aqueous sulfuric acid solution (4 equivalents of sulfuric acid versus 12 equivalents of LiAlH4 in water) in THF. The precipitate was removed by filtration and the solid was washed with THF (3 x 400 mL). The filtrate was concentrated under reduced pressure to give the white solid product 1,18-octadecanediol (12.3 g, 98% yield). 1H NMR (400 MHz, THF-d8, TMS): δ (ppm) = 3.45 (dd, J = 11.35, 6.15 Hz, 4H, HO-CH2-CH2-), 2.49 (s, 2H, HO-CH2-), 1.46 (m, 4H, HO-CH2-CH2-), 1.39-1.25 (m, 24H, - CH2-(CH2)12-CH2-). 13C NMR (100 MHz, THF-d8, TMS): δ (ppm) = 62.7 (HO-CH2-), 34.3 (HO-CH2-CH2-), 30.9-30.7 (-CH2-(CH2)12-CH2-), 27.1 (HO-(CH2)2-CH2-). IR (cm-1): 3414, 3355, 2917, 2846, 1468, 1352, 1334, 1059, 1046, 1015, 979, 723. MS (EI): m/z (%) Calculated C18H38O2Na: 309.2770; measured: 309.2770.

References

[1] Schwab S T, et al. Correlation of Enzymatic Depolymerization Rates with the Structure of Polyethylene-Like Long-Chain Aliphatic Polyesters[J]. ACS Macro Letters, 2024, 13: 1245-1250. DOI:10.1021/acsmacrolett.4c00463

1,18-octadecanediol (3155-43-9)Related Product Information

• 2-Butyne-1,4-diol
• 2-Methyl-2,4-pentanediol
• alpha-Cyperone
• beta-Eudesmol
• MOSLOFLAVONE
• Hydroxyecdysone
• Artemether
• beta-Sitosterol
• alpha-Terpineol
• 2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one
• hydroxygenkwanin
• (4E,6E)-1,7-Diphenyl-4,6-heptadien-3-one
• 1,3-Adamantanediol
• Octadecanediol