Synthesis of myrcene by pyrolysis of β-pinene: Analysis of decomposition reactions

Kolicheski, Mônica Beatriz; Côcco, Lílian Cristina; Mitchell, David A.; Kaminski, Moacir

doi:10.1016/j.jaap.2007.01.005

Cited by 48 publications

(38 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[19][20][21] is rather not expected at T max1 . The formation of these decomposition products was observed at relatively higher temperatures according to literature data [22,23].…”

Section: Tg/dsc/ftir Characterization Of Linear Geranyl Diestersmentioning

confidence: 62%

TG/DSC/FTIR characterization of linear geranyl diesters

Worzakowska

Ścigalski

2012

J Therm Anal Calorim

View full text Add to dashboard Cite

The synthesis, thermal behavior, and characterization of the decomposition products of linear geranyl diesters: digeranyl succinate, digeranyl glutarate, digeranyl adipinate, and digeranyl sebacinate were presented. The linear geranyl diesters were prepared in direct esterification process of a molar stoichiometric ratio of geraniol and suitable acidic reagent in solvent-free medium at 130°C using butylstannoic acid as a catalyst. Their structure was confirmed based on FTIR, 1 H-and 13 C-NMR spectra. It was proved that the use of tin catalyst allowed decreasing the reaction time and increasing the final conversion of substrates when compared to non-catalyzed process. It considerably simplifies the processing by reduction of the preparation cost and thus this new method of synthesis of aroma diesters may be attractive for practical applications. The thermal behavior of prepared compounds was studied by TG/DSC/FTIR coupled method. TG analysis showed that diesters are thermally stable up to temperatures above 200°C. The DTG curves confirmed that these decomposition run as a single-stage process. The T max1 were in the range of 294.5-313.8°C depending on the aliphatic chain length (-CH 2 -) n in the structure of aroma diesters, which was in accordance with DSC data. The analysis of the gases evolved during heating of diesters in inert atmosphere indicated on the asymmetrical disrupt of their bonds. The cleavage of ester bond and O-geranyl bond was expected. It resulted in production of the mixture of derivatives of geraniol (acyclic and alicyclic monoterpene hydrocarbons) like myrcene, ocimene, or limonene as main decomposition products. In addition, the formation of anhydride, lactone, or ketone functionalities among the degradation products clearly confirmed the proposed degradation path of studied diesters.

show abstract

“…[19][20][21] is rather not expected at T max1 . The formation of these decomposition products was observed at relatively higher temperatures according to literature data [22,23].…”

Section: Tg/dsc/ftir Characterization Of Linear Geranyl Diestersmentioning

confidence: 62%

TG/DSC/FTIR characterization of linear geranyl diesters

Worzakowska

Ścigalski

2012

J Therm Anal Calorim

View full text Add to dashboard Cite

show abstract

“…The most commonly used method for production of 2 is the thermally induced rearrangement of 1 in a temperature range of 450-600 8C [7,[11][12][13][14][20][21][22][23][24][25][26]. Under these conditions, different side-reactions occur leading to the formation of limonene (3) and c-limonene (D-1(7),8-p-menthadiene; 4), as shown in Scheme 1 [9,11,[21][22][23].…”

Section: Introductionmentioning

confidence: 99%

“…Under these conditions, different side-reactions occur leading to the formation of limonene (3) and c-limonene (D-1(7),8-p-menthadiene; 4), as shown in Scheme 1 [9,11,[21][22][23]. Consecutive reactions of the target compound 2 lead to the formation of further isomerization products (5, 6; Scheme 1) [11][12][13][14]23] and coke [24] resulting in a decreased selectivity for 2. Another possible synthetic route to 2 is based on the reaction of ethyl acetoacetate with isoprene bromide yielding b-keto esters which can be converted into 2 via Wittig reaction [18,19,27].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Kinetic and mechanistic aspects of myrcene production via thermal-induced β-pinene rearrangement

Stolle

Bonrath

Ondruschka

2008

Journal of Analytical and Applied Pyrolysis

View full text Add to dashboard Cite

“…Myrcene is an oily liquid extracted from the essential oils of many plants. In industry it is mainly obtained from the pyrolysis of β-pinene (Kolicheskia et al 2007), which is produced from the distillation of pine tree oil and is already used in many industrial processes. The chemical structure of myrcene (Fig.…”

Section: Introductionmentioning

confidence: 99%

Renewable Myrcene-based UV-curable Monomer and its Copolymers with Acrylated Epoxidized Soybean Oil: Design, Preparation, and Characterization

Yang¹,

Li²,

Xia³

et al. 2015

BioResources

View full text Add to dashboard Cite

An innovative myrcene-based ultraviolet curable vinyl ester monomer was synthesized, and its molecular structure was analyzed with Fourier transform infrared spectroscopy and nuclear magnetic resonance ( 1 HNMR and 13 CNMR) analysis. A series of copolymers were also prepared by mixing the myrcene-derived monomer with another vinyl ester monomer, acrylated epoxidized soybean oil, under ultraviolet light. The curing process was monitored using Fourier transform infrared spectroscopy. Ultraviolet curing analysis showed that all the mixed systems had high curing rates and were fully cured within the first 30 seconds. When the weight ratio of myrcene-derived monomer to acrylated epoxidized soybean oil was 50/50, the ultimate double bond conversion reached 94.08%. Dynamic mechanical analysis showed that the storage modulus and glass transition temperature of the cured resins both increased with increasing content of myrcene vinyl ester monomer because the molecular structure of myrcene-derived vinyl ester monomer was more rigid and stronger than that of acrylated epoxidized soybean oil. Thermogravimetric analysis indicated that the main thermal initial decomposition temperatures were all above 360 °C, demonstrating that the copolymers had modest thermal stability.

show abstract

Synthesis of myrcene by pyrolysis of β-pinene: Analysis of decomposition reactions

Cited by 48 publications

References 10 publications

TG/DSC/FTIR characterization of linear geranyl diesters

TG/DSC/FTIR characterization of linear geranyl diesters

Kinetic and mechanistic aspects of myrcene production via thermal-induced β-pinene rearrangement

Renewable Myrcene-based UV-curable Monomer and its Copolymers with Acrylated Epoxidized Soybean Oil: Design, Preparation, and Characterization

Contact Info

Product

Resources

About