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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2023 · IF 2.6

Isothermal Vapor–Liquid Equilibrium Data for a Binary System of (−)-α-Pinene + (−)-Limonene and a Quaternary System of (−)-α-Pinene + (−)-Limonene + Water + Ethephon at 313.2, 323.2, and 333.2 K

Xuejuan Wei,Xiaopeng Chen,Linlin Wang,Xiaojie Wei,Jiaqi Liang,Zehui Xiong,Jiezhen Liang

For the isolation and purification of (−)-α-pinene and (−)-limonene from pine resin tapping by spraying ethephon solution on the cutting surface of pine tree, vapor–liquid equilibrium data for (−)-α-pinene and (−)-limonene with ethephon are indispensable. In this work, the isothermal vapor–liquid equilibria of binary system (−)-α-pinene + (−)-limonene and quaternary system (−)-α-pinene + (−)-limonene + water + ethephon were determined using headspace gas chromatography. The thermodynamic consistency of the experimental data was tested by the Van Ness point test and Redlich-Kister area test. The universal quasi-chemical (UNIQUAC) and nonrandom two-liquid (NRTL) models were applied to correlate the experimental data, and the absolute mean deviation of the vapor phase mole fraction and the relative mean deviation of the total system pressure were calculated. The results showed that the UNIQUAC model correlated the system more accurately than the NRTL model. The relative volatility of (−)-α-pinene to (−)-limonene was promoted by adding ethephon solution. In addition, the binding energies of (−)-α-pinene + water + ethephon and (−)-limonene + water + ethephon were calculated by DFT. The results showed that the intermolecular interaction between ethephon solutions with (−)-limonene was greater than that with (−)-α-pinene.

CAS / MDL: 7785-26-4
研究领域: 化学工程 · 植物化学 · 热力学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2023 · IF 8.6

Refinement of limonene epoxides from the light distillate of tire pyrolysis oil via catalytic epoxidation

Yulin Zhang,Shuo Cheng,Guozhao Ji,Aimin Li

The light fractions of tire pyrolysis oil (TPO) are rich in valuable chemicals, such as limonene, but the utilization of TPO-derived limonene or limonene derivatives was limited by the difficulties to separate limonene from the rest compounds, especially p -cymene which has a similar molecular structure and physical properties (molecular size, melting point and boiling point) as limonene. In order to utilize limonene and separate p -cymene, this study took advantage of the difference in oxidizability between limonene and p -cymene, and proposed a method of epoxidizing TPO before the separation. After epoxidation, limonene was successfully converted into limonene epoxides, while aromatic compounds in TPO such as p -cymene were inert and non-oxidizable. Limonene epoxides have a higher boiling point than p -cymene, so the limonene epoxides can be easily refined by distillation. In order to accelerate the oxidation of limonene, a peroxophosphotungstate catalyst was used as a sustainable solvent-free process. The fraction of TPO between 160 and 190 °C which has 298 g/L limonene was tested in this study. The epoxidation of the TPO 160-190 could reach complete conversion to limonene 1,2-oxides and diepoxide limonene. The resulting oil could be divided into p -cymene enriched fraction and limonene epoxides enriched fraction by simple distillation, and the limonene epoxides enriched fraction contained more than 80% of limonene epoxides. The catalytic mechanism was proposed with the assistance of FT-IR, GC–MS, and 31 P NMR analysis. This work presents a novel strategy of epoxidizing limonene for limonene epoxide and p -cymene separation, which could bring a breakthrough for limonene epoxide and p -cymene production from waste-derived oils.

CAS / MDL: 107-64-2 12501-23-4
研究领域: 化学工程 · 环境科学
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ADVANCED FUNCTIONAL MATERIALS · 2015 ·Vol. 25 ·期 18 ·2754-2762 · IF 11.805

Sunlight-Induced Cross-Linked Luminescent Films Based on Polysiloxanes and d-Limonene via Thiol–ene “Click” Chemistry

Yujing Zuo,Jinfeng Cao,Shengyu Feng

The increasing pursuit of biocontained elastic materials led the investigation of the potential use of the monoterpene limonene in film synthesis via thiol–ene reaction. Poly[(mercaptopropyl)methylsiloxane] (PMMS) is first synthesized. By controlling the molar ratio of PMMS and functional monomers, such as polyethylene glycol allyl methyl ether or rhodamine-B, PMMS is partially functionalized while leaving spare mercapto groups that could be further used as cross-linking sites. On the basis of the functionalized PMMS, novel transparent silicone luminescent films with hydrophilic tunable properties are prepared by natural-sunlight-triggered thiol–ene “click” chemistry by using d -limonene as a cross-linker. Their structures and properties are thoroughly characterized. Transparent luminescent films are coated on commercially available UV-light emitting diode (LED) cell from solution medium followed by an in situ cross-linking step; a colorful LED cell is obtained through this facile and efficient method. The UV-LED coated by films show very intense photoluminescence under normal visible light or the light is on, and has very high coloric purity.

研究领域: 材料科学 · 化学工程
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2023 · IF 4.2

Terpene-Based Sustainable Elastomer for Low-Temperature-Resistant Applications: Synthesis, Preparation, and Properties of Poly(isoprene-co-myrcene)

Shuainan Zhao,Haijun Ji,Jie Yu,Rui Wang,Liqun Zhang,Runguo Wang

A series of green poly(isoprene-co-myrcene) (PIMy) elastomers were designed and prepared by coordination polymerization to solve the fossil shortage and achieve an excellent low-temperature resistance property. The properties of PIMy could be tailored upon varying the comonomer feed ratios. The structure and thermal stability were investigated by NMR, differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA) analyses. The cis-1,4 structure content of PIMy exceeded 95%, and the Tg of PIMy was below −60 °C without crystallization at low temperatures. With the increase of myrcene content, the tensile strength of PIMy/silica nanocomposites decreased, the wet skid resistance was improved, and PIMy with myrcene content of 5–20 mol % had better comprehensive properties. The introduction of PIMy in solution-polymerized styrene–butadiene rubber (SSBR) increased the tan δ value at −20 °C and improved the ice skid resistance performance. The Laboratory Abrasion Tester (LAT-100) test results showed that the addition of PIMy significantly improved the friction of SSBR on the ice surface with a maximum improvement of 161%. The PIMy prepared in this study is expected to be used in low-temperature-resistant rubber products such as seals and winter tires.

CAS / MDL: 123-35-3
研究领域: 材料科学 · 高分子化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2018 · IF 3.412

Tunable d-Limonene Permeability in Starch-Based Nanocomposite Films Reinforced by Cellulose Nanocrystals

Siyuan Liu,Xiaoxi Li,Ling Chen,Lin Li,Bing Li,Jie Zhu

In order to control d-limonene permeability, cellulose nanocrystals (CNC) were used to regulate starch-based film multiscale structures. The effect of sphere-like cellulose nanocrystal (CS) and rod-like cellulose nanocrystal (CR) on starch molecular interaction, short-range molecular conformation, crystalline structure, and micro-ordered aggregated region structure were systematically discussed. CNC aspect ratio and content were proved to be independent variables to control d-limonene permeability via film-structure regulation. New hydrogen bonding formation and increased hydroxypropyl starch (HPS) relative crystallinity could be the reason for the lower d-limonene permeability compared with tortuous path model approximation. More hydrogen bonding formation, higher HPS relative crystallinity and larger size of micro-ordered aggregated region in CS0.5 and CR2 could explain the lower d-limonene permeability than CS2 and CR0.5, respectively. This study provided new insight for the control of the flavor release from starch-based films, which favored its application in biodegradable food packaging and flavor encapsulation.

CAS / MDL: 56-81-5
研究领域: 材料科学 · 食品科学
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