34316-64-8

Basic information

• Product Name: hexyl laurate
• Synonyms: hexyl laurate;Hexyl dodecanoate;Dodecanoic acid, hexyl ester;Hexyllaurat;Lauric acid hexyl ester;Einecs 251-932-1;Hexyl dodecanoat;Laurinsaeurehexylester
• CAS NO: 34316-64-8
• Molecular Formula: C₁₈H₃₆O₂
• Molecular Weight: 284.47724
• EINECS: 251-932-1
• Mol File: 34316-64-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: -3.4 °C
• Boiling Point: 334.7 °C at 760 mmHg
• Flash Point: 158.5 °C
• Appearance: /
• Density: 0.864 g/cm³
• Vapor Pressure: 0.000126mmHg at 25°C
• Refractive Index: 1.442
• CAS DataBase Reference: hexyl laurate(CAS DataBase Reference)
• NIST Chemistry Reference: hexyl laurate(34316-64-8)
• EPA Substance Registry System: hexyl laurate(34316-64-8)

Safety Data

• Hazardous Substances Data: 34316-64-8(Hazardous Substances Data)

Usage

Uses

hexyl laurate is a mild emollient and a vehicle for lipid-soluble active ingredients. It is non-irritating and practically odorless. It enhances product spreadability and feel on skin.

Synthesis Reference(s)

Journal of the American Chemical Society, 98, p. 1629, 1976 DOI: 10.1021/ja00422a083

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C18H36O2/c1-3-5-7-9-10-11-12-13-14-16-18(19)20-17-15-8-6-4-2/h3-17H2,1-2H3

Synthetic route

vinyl laurate (2146-71-6) + hexan-1-ol (111-27-3) → lauric acid hexyl ester (34316-64-8)

Conditions	Yield
With carbon dioxide at 46.02℃; under 66081.6 Torr; for 3.5h; Reagent/catalyst; High pressure; Supercritical conditions; Green chemistry;	97%

lauric acid (143-07-7) + hexan-1-ol (111-27-3) → lauric acid hexyl ester (34316-64-8)

Conditions	Yield
With glucose-diphenylaminium tosylate-derived carbon solid acid (GDTCSA) In n-heptane at 80℃; for 4h;	93%
With 2,2,6,6-tetramethylpiperidinium triflate In neat liquid at 120℃; for 9h; Green chemistry;	93%
With toluene-4-sulfonic acid; 1-octyl-3-methylimidazolium tetrafluoroborate at 80℃; for 1h;	90%

methyl n-dodecanoate (111-82-0) + hexan-1-ol (111-27-3) → lauric acid hexyl ester (34316-64-8)

Conditions	Yield
With SO3H and NH2+ functional carbon-based solid acid at 80℃; for 8h;	93%

1-Decene (872-05-9) + 1-hexyl acetate (142-92-7) → lauric acid hexyl ester (34316-64-8)

Conditions	Yield
With di-tert-butyl peroxide at 158 - 160℃;

ethyl laurate (106-33-2) + hexan-1-ol (111-27-3) → ethanol (64-17-5) + lauric acid hexyl ester (34316-64-8)

Conditions	Yield
With Lipase enzyme preparation In benzene Ambient temperature; Lipases catalyzed transesterification;

ethyl laurate (106-33-2) + tributyl-(hexyloxy)-tin (62774-20-3) → lauric acid hexyl ester (34316-64-8) + EtOSnBu3

Conditions	Yield
With Lipase enzyme preparation In benzene Ambient temperature; Lipases catalyzed transesterification;

ethyl laurate (106-33-2) + tributyl-(hexyloxy)-tin (62774-20-3) → lauric acid hexyl ester (34316-64-8) + tributyltin ethoxide (682-00-8)

Conditions	Yield
With lipase catalyst In benzene refluxing (8 h, azeotropic removal of water); not isolated, IR spectroscopy;

p-Nitrophenyl laurate (1956-11-2) + hexan-1-ol (111-27-3) → lauric acid hexyl ester (34316-64-8)

Conditions	Yield
With induced mycelium-bound lipase from Aspergillus niger MYA 135 In hexane; acetone at 37℃; for 1h; Reagent/catalyst; Enzymatic reaction;

methyl n-dodecanoate (111-82-0) + hexan-1-ol (111-27-3) → methanol (67-56-1) + lauric acid hexyl ester (34316-64-8)

Conditions	Yield
With cerium(IV) oxide at 160℃; for 24h;	A n/a B 85 %Chromat.

Upstream product

• 143-07-7 lauric acid 
• 111-27-3 hexan-1-ol 
• 872-05-9 1-Decene 
• 142-92-7 1-hexyl acetate 
• 106-33-2 ethyl laurate 
• 62774-20-3 tributyl-(hexyloxy)-tin 
• 111-82-0 methyl n-dodecanoate 
• 2146-71-6 vinyl laurate 
• 1956-11-2 p-Nitrophenyl laurate 

Relevant articles and documents

2,2,6,6-Tetramethylpiperidinium triflate (TMPT): a highly selective and self-separated catalyst for esterification

An eco-friendly and readily accessible 2,2,6,6-tetramethylpiperidinium triflate was found as highly-selective and self-separated catalyst for esterification under solvent-free condition. The X-ray crystallography revealed that it formed a ‘hydrophobic wall’ which could effectively eliminate the generated water from the reactive sites. Moreover, it could precipitate from the reaction system with excellent recovery ratio (>99%) and be reused for ten times without any significant loss of activity.

Immobilization of lipase on biocompatible co-polymer of polyvinyl alcohol and chitosan for synthesis of laurate compounds in supercritical carbon dioxide using response surface methodology

Biocompatible co-polymer matrix has great importance for enzyme immobilization and subsequent biocatalytic applications to synthesize important organic moieties. Citronellyl laurate is a fatty-acid-ester having pleasant fruity aroma and widely used as/in emulsifier, lubricant in textile, paint or ink-additives, surfactants, perfumery and food-flavouring ingredient. In present study, Burkholderia cepacia lipase (BCL) was immobilized on biodegradable co-polymer of chitosan (CHI) and polyvinyl alcohol (PVA). The synthesized bio-catalyst {PVA:CHI:BCL (6:4:2.5)} was characterized by SEM, TGA, lipase assay and protein-content analysis. This biocatalyst was applied to synthesize citronellyl laurate in supercritical carbon-dioxide (SC-CO2) using response surface methodology with five-factor-three-level Box-Behnken-design to optimize reaction parameters (citronellol: 8.5 mmol; vinyl laurate: 19.87 mmol; biocatalyst: 175.6 mg; temperature: 46.02 °C; pressure: 8.81 MPa) which provided 94 ± 1.52% yield. The protocol is extended to synthesize various important 12 laurate compounds with excellent yield (90-98%) and noteworthy recyclability (upto studied 5 recycles). Interestingly, immobilized PVA/CHI/lipase biocatalyst showed 4-fold higher bio-catalytic activity than free lipase in SC-CO2. Moreover, the biocatalyst activity assessment study showed remarkable activity-stability of immobilized biocatalyst in SC-CO2 media as compared to free enzyme. Thus, present protocol demonstrated potential biocatalytic applications for synthesis of important laurate compounds with excellent recyclability in SC-CO2 as greener biocatalyst and reaction medium.

Biocatalysis in bio-derived solvents: An improved approach for medium optimisation

An improved multi-parameter approach to the correlation of enzymatic activity and solvent properties is proposed. The development of the correlation facilitated the introduction of renewable solvents in a CALB catalysed synthesis of fatty esters. the Partner Organisations 2014.