Abstract Camellia oleifera seed cake (COSC), a byproduct during oil production of C. oleifera seeds, has been extremely abundant. However, due to the lack of systematic and in-depth analysis about the chemical composition of COSC, it is difficult to develop high value-added products, resulting in low processing efficiency or even directly abandoned. In this paper, the VOCs (Volatile organic components) characteristics of COSC and the variation rule of COSC groups before/after extraction were revealed, and the thermal loss law of COSC and the pyrolyzates characteristics at different temperatures were also explained. The main VOCs of ethanol extractive of COSC are alcohols, those of petroleum ether extractive are alkanes and organic acids, and those of benzene/ethanol extractive are esters. It is first reported here that rich 1,6,10-Dodecatrien-3-ol,3,7,11-trimethyl-, (E)-, namely nerolidol with wide use in cosmetics and biomedicine, exists in COSC extractives. In addition, bioactive VOCs such as β-caryophyllene, humulene and (E)-Atlantone were observed in three COSC extractives. The total content trend from high to low is petroleum ether extractive, ethanol extractive, benzene/ethanol extractive, indicating that petroleum ether extractive has the best developing prospects. The analytic results of FTIR further confirm that: (1) the COSC contains components including Si compounds, ethers, organic acids, esters and alcohols, (2) the four kinds of organic silicon detected are naturally occurring components in COSC, and (3) organic solvent extraction does not make compound groups of COSC significantly changed. There are four obvious stages in thermogravimetry treatment of COSC: the first (30–100 °C), the second (180–240 °C), the third (240–400 °C), and the fourth (400–567 °C), and the order of the mass loss is the third, the second, the fourth and the first. During thermogravimetry treatment, three critical turning points of temperature (240 °C, 400 °C and 567 °C) were observed, accompanied by significantly chemical changes such as macromolecule pyrolyzed into small volatile molecules. The four COSC extractive pyrolyzates at 300 °C, 450 °C, 600 °C and 750 °C have different content variation in the components, such as heterocyclic type with a high-low-high-low change, hydrocarbons and acids shown by the high-low-low-high process, and ketone and the alcohol with a low-high-low-high change. The 450 °C pyrolyzates of COSC residue after extraction are heterocyclic, ketone, phenolic more than esters, hydrocarbons, phosphide, acids, aldehydes, alcohols and acyl; the 600 °C pyrolyzates are heterocyclic, ketone, phenolic more than esters, ammonium, phosphide, acid, aldehydes and alcohols. Here, a large number of new components are produced in the pyrolysis treatment for COSC extractive and residue, providing a new approach for the high-grade application of COSC.

中文翻译：

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油茶籽饼挥发性有机成分和热解物的系统表征用于开发高附加值产品

摘要 油茶籽饼 (COSC) 是油茶籽油生产过程中的副产品，其储量极为丰富。但是，由于对COSC的化学成分缺乏系统深入的分析，难以开发高附加值的产品，导致加工效率低下甚至直接废弃。本文揭示了COSC的VOCs(Volatile Organic Components)特性和提取前后COSC基团的变化规律，并解释了COSC的热损失规律和不同温度下的热解物特性。COSC乙醇提取物的主要VOCs为醇类，石油醚提取物的VOCs主要为烷烃和有机酸，苯/乙醇提取物的VOCs主要为酯类。这里首先报道了富含 1,6,10-Dodecatrien-3-ol，3,7,11-三甲基-，(E)-，即广泛用于化妆品和生物医学的橙花醇，存在于COSC提取物中。此外，在三种 COSC 提取物中观察到生物活性 VOC，如 β-石竹烯、葎草烯和 (E)-Atlantone。总含量从高到低的趋势是石油醚提取物、乙醇提取物、苯/乙醇提取物，表明石油醚提取物的发展前景最好。FTIR分析结果进一步证实：（1）COSC中含有Si化合物、醚类、有机酸、酯类和醇类等成分；（2）检测到的四种有机硅均为COSC中天然存在的成分；（3）有机溶剂萃取并未使COSC的化合物基团发生显着变化。COSC的热重处理有四个明显的阶段：第一个 (30–100 °C)、第二个 (180–240 °C)、第三个 (240–400 °C) 和第四个 (400–567 °C)，质量损失的顺序是第三，第二，第四和第一。在热重法处理过程中，观察到三个临界温度转折点（240°C、400°C和567°C），伴随着显着的化学变化，如大分子热解为挥发性小分子。300°C、450°C、600°C和750°C的四种COSC萃取热解物组分含量变化不同，如杂环型高-低-高-低变化，烃类和酸类如图所示。高-低-低-高过程，酮和醇有低-高-低-高变化。萃取后COSC渣450℃热解产物为杂环、酮、酚类多酯、烃类、磷化物、酸、醛、醇和酰基；600°C的热解产物是杂环、酮、酚多于酯、铵、磷化物、酸、醛和醇。在这里，COSC 提取物和残渣的热解处理产生了大量新组分，为COSC 的高档化应用提供了新途径。