106-18-3

Usage

Uses

Used in Organic Synthesis:
Dodecanoic acid, butyl ester is used as a key intermediate in the synthesis of various organic compounds, contributing to the development of new materials and chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, butyl laurate is utilized as a raw material for the production of drugs and medications, taking advantage of its chemical properties to enhance the efficacy and delivery of active pharmaceutical ingredients.
Used in Agrochemicals:
Dodecanoic acid, butyl ester is employed in the agrochemical sector as a component in the formulation of pesticides, herbicides, and other agricultural products, aiding in the improvement of crop protection and yield.
Used in Dyestuff Industry:
Butyl laurate is used as a crucial raw material in the dyestuff industry for the production of various dyes and pigments, leveraging its chemical properties to create vibrant and stable colorants for different applications.
Used in Flavor and Fragrance Industry:
Due to its characteristic fruity, peanut-like odor, Dodecanoic acid, butyl ester is also used in the flavor and fragrance industry to add unique scents and flavors to various products, such as food, beverages, and cosmetics.

Preparation

By esterification of lauric acid with n-butyl alcohol in the presence of H2SO4 or by conducting the esterification using gaseous HCl as a catalyst.

InChI:InChI=1/C16H32O2/c1-3-5-7-8-9-10-11-12-13-14-16(17)18-15-6-4-2/h3-15H2,1-2H3

Upstream product

• 112-41-4 1-dodecene 
• 1120-36-1 1-tetradecene 
• 872-05-9 1-Decene 
• 821-95-4 1-undecene 
• 2437-56-1 1-tridecene 
• 13360-61-7 1-pentadecene 
• 201230-82-2 carbon monoxide 
• 71-36-3 butan-1-ol 
• 1956-11-2 p-Nitrophenyl laurate 
• 111-82-0 methyl n-dodecanoate 
• 2146-71-6 vinyl laurate 
• 141-32-2 acrylic acid n-butyl ester 
• 7003-75-0 allyl dodecanoate 
• 143-07-7 lauric acid 

Downstream Products

• 102456-10-0 lauric acid-(2,4-dimethyl-benzyl ester) 
• 112-53-8 1-dodecyl alcohol 
• 112-42-5 undecyl alcohol 
• 629-76-5 pentadecanol 
• 112-70-9 tridecan-1-ol 
• 112-72-1 1-Tetradecanol 
• 36653-82-4 1-Hexadecanol 

Relevant academic research and scientific papers

Effect of polyvinylpyrrolidone on mesoporous silica morphology and esterification of lauric acid with 1-butanol catalyzed by immobilized enzyme

Mesoporous silica materials with a range of morphology evolution, i.e., from curved rod-shaped mesoporous silica to straight rod-shaped mesoporous silica, were successfully prepared using polyvinylpyrrolidone (PVP) and triblock copolymer as dual template. The effects of PVP molecular weight and concentration on mesoporous silica structure parameters were studied. Results showed that surface area and pore volume continuously decreased with increased PVP molecular weight. Mesoporous silica prepared with PVP K30 also possessed larger pore diameter, interplanar spacing (d100), and cell parameter (a0) than that prepared with PVP K15 and PVP K90. In addition, with increased PVP concentration, d100 and a0 continuously decreased. The mechanism of morphology evolution caused by the change in PVP concentration was investigated. The conversion rate of lauric acid with 1-butanol catalyzed by immobilized Porcine pancreatic lipase (PPL) was also evaluated. Results showed that PPL immobilized on amino-functionalized straight rod-shaped mesoporous silica maintained 50% of its esterification conversion rate even after five cycles of use with a maximum conversion rate was about 90.15%.

Solvent-free biocatalytic interesterification of acrylate derivatives

The ability of diverse commercial lipases and whole cells (fungal resting cells) to synthesise allyl and dichloropropyl acrylate from allyl dodecanoate through an interesterification process is presented. The process was carried out without solvent in a conventional batch system. The best biocatalyst among those studied was the commercial enzyme CALB (Candida antarctica lipase B immobilised onto a macroporous acrylic resin). The reaction was sensitive to water activity, and a decrease in the yield was observed at the highest activity studied. CALB could also be applied to diverse acrylic derivatives, although the yields decreased using either ethyl methacrylate or acrylic acid.

Effect of Ionic Liquids on the Chemical Equilibrium of Esterification of Carboxylic Acids with Alcohols

The esterification of carboxylic acids with alcohols catalyzed by paratoluene sulfonic acid (pTSA) was studied in different room temperature ionic liquids. The chemical equilibrium of esterification can be tuned by using ionic liquids as solvents.

Performance in synthetic applications of a yeast surface display-based biocatalyst

This work demonstrates the effectiveness of yeast surface display (YSD) as a scaffold for biocatalysts in hydrophobic, non-aqueous environments. Two lipases, Candida antarctica lipase B (CalB) and Photobacterium lipolyticum sp. M37 lipase (M37L), were immobilized independently by surface display on Saccharomyces cerevisiae. The two YSD biocatalysts were employed to synthesize esters of butanol and saturated fatty acids of varying length (8 to 16 carbons) in heptane. Effects of fatty acid chain length and temperature on the esterification reaction were examined. The YSD catalysts synthesized butyl decanoate in 10 repeated batches with little loss in activity. Compared to a commercial immobilized lipase (Novozym 435), the activity of both YSD lipases was lower on a mass loading basis, but higher when normalized on estimates of protein loading. Initial-rate kinetics of the butyl decanoate reaction were measured for the CalB-displaying yeast. Kinetics and apparent activity of M37L in the multi-batch experiments depend heavily on water concentration; kinetics for M37L could not be elucidated with initial-rate methods. The difference between CalB and M37L in water requirements illustrates a critical parameter for optimization of lipase activity in non-aqueous environments. The activity of both lipases in a completely hydrophobic environment is a step towards more economical biocatalysis of industrial esterification.

An improved greener esterification of fatty alcohols using a renewable acid-ionic liquid couple as catalyst-solvent

We have developed a simple and efficient method for the esterification of various organic acids with C4-C18 alcohols using the 1-octyl-3-methyl- imidazolium tetrafluoroborate-para-toluenesulphonic acid (OMIM/BF 4-PTSA) couple, without organic solvent, either by classic heating or by microwave irradiation. The utilisation of the OMIM/BF4-PTSA couple presents considerable advantages: high yield, low temperature, short reaction time, isolation of the ester by simple decantation, easy reuse of the catalyst couple.

A novel poly(p-styrenesulfonic acid) grafted carbon nanotube/graphene oxide architecture with enhanced catalytic performance for the synthesis of benzoate esters and fatty acid alkyl esters

Considering the issue of low yield in the synthesis of benzoate esters and fatty acid alkyl esters, designing a high catalytic activity composite catalyst is very significant and attractive. In this study, the rational design strategy was used to develop a novel poly(p-styrenesulfonate acid, namely PSSF) grafted multi-walled carbon nanotube composite with graphene oxide nanomaterial (PSSF-mCNTs-GO) using a simple two-step method. FT-IR and Raman spectroscopy, XRD, SEM, TEM, and NH3-TPD were used to characterize the inorganic-organic hybrid material. In particular, the addition of GO remarkably enhanced its catalytic performance in the production of fatty acid alkyl esters (92.16%) and benzoate esters (90.27%), in which the conversion was more than doubled as a result of its strong π-π interaction with the substrate. In addition, PSSF-mCNTs-GO can be separated from the substrate conveniently and still maintained a relatively high catalytic activity even after 6 times recycling, which indicates its rather good reusability. This novel catalyst is promising in the synthesis of biodiesel and benzoate esters.

Evaluation of deep eutectic solvents as new media for Candida antarctica B lipase catalyzed reactions

This study aimed at analyzing the advantages and limitations of several deep eutectic solvents (DESs) as 'green solvents' for biotransformation using immobilized Candida antarctica lipase B as catalyst. The transesterification of vinyl laurate was chosen

Novel SO3H-functionalized polyoxometalate-based ionic liquids as highly efficient catalysts for esterification reaction

Three novel heteropolyanion-based Br?nsted acidic ionic liquids (BAILs), butane mono sulfoacid-functionalized 1,10-phenanthrolinum, butane mono and bis sulfoacid-functionalized 1,4-dimethylpiperazinium salts of phosphortungstate catalyst (PhBs1-PW, [PipBs1]3-PW and [PipBs2]3-(PW)2) were synthesized and well characterized with FTIR, 1H and 13C NMR, Electro-Spray Ionization Mass Spectrometry (ESI-MS), Elemental analysis (CHNS), EDX and TG analysis techniques. The esterification reactions of monocarboxylic acids with monohydric alcohols were carried out using these catalysts. The introduced catalysts present a self-separation performance after reaction, which can be easily recovered and quite steadily reused as confirmed by six-run recycling test. Moreover, bis sulfoacid-functionalized 1,4-dimethylpiperazinium salt of phosphortungstate showed the best catalytic performance among the prepared catalysts for the esterification reaction.

A novel Bronsted acidic heteropolyanion-based polymeric hybrid catalyst for esterification

A new SO3H-functionalized HPA-based acidic polymeric hybrid was prepared by coupling task-specifically designed SO3H-functionalized polymeric ionic liquid with Keggin-structured heteropolyanion, and characterized by 1H NMR, FT-IR, TG, XRD, BET, Hammett indicator, melting point, and elemental analysis. Its catalytic performance for esterification of alcohols with carboxylic acids was studied under solvent-free conditions. The results demonstrate that the polymeric hybrid is a highly active and selective solid catalyst for various esterifications, and can be easily recovered and steadily reused.

Robust acidic pseudo-ionic liquid catalyst with self-separation ability for esterification and acetalization

The novel acidic pseudo-ionic liquid catalyst with self-separation ability has been synthesized through the quaternization of triphenylphosphine and the acidification with silicotungstic acid. The pseudo-IL showed high activities for the esterification with average conversions over 90%. The pseudo-IL showed even higher activities for acetalization than traditional sulfuric acid. The homogeneous catalytic process benefited the mass transfer efficiency. The pseudo-IL separated from the reaction mixture automatically after reactions, which was superior to other IL catalysts. The high catalytic activities, easy reusability and high stability were the key properties of the novel catalyst, which hold great potential for green chemical processes.