Intensification of ball milling on the synthesis of dimer acid catalyzed by activated clay

doi:10.16085/j.issn.1000-6613.2017-1425

Abstract

Abstract: In this work,ball milling method was utilized to intensify the preparation process of dimer acid. The effects of reaction temperature,amount of catalyst,amount of co-catalyst,stirring blade type,stirring speed and amount of milling medium on the yield of dimer acid were investigated in the ball mill reactor. The results showed that the ball milling method can enhance the synthesis of dimer acid catalyzed by activated clay. A crude product with dimer acid content of 79%,acid value of 196mgKOH/g and viscosity of 1640mPa·s was prepared with water vapor when reaction temperature was 260℃,catalyst and cocatalyst amount was 24% and 0.5% respectively,a double propeller blade was used at the stirring speed of 173r/min,1500g zirconia was used as the milling medium,and the yield of dimer acid was 58.7%. Compared to the stirred tank,the content of dimer acid in the crude product was increased by 75% in the intensification of ball milling. The products were characterized by infrared spectroscopy (FTIR)and HPLC-Mass,the obtained dimer acid product is mainly composed of bicyclic dimer acid and acyclic dimer acid. The ratio of bicyclic dimer acid and acyclic dimer acid was 1.07:1.

Key words: polymerization, catalysis, ball milling, preparation, dimer acid

摘要： 采用球磨法强化白土催化制备二聚酸过程。以二聚酸的产率为评价指标，在球磨反应釜中考察了反应温度、催化剂用量、助催化剂用量、搅拌桨叶型式、搅拌速度、球磨介质用量对二聚酸合成的影响，并与搅拌釜的结果比较。结果表明：球磨法可以强化活性白土催化二聚酸合成过程，水蒸气氛围下，在反应温度260℃、催化剂质量分数24%、助催化剂质量分数0.5%，采用双螺旋带型桨叶、搅拌速度173r/min，球磨介质为氧化锆、球磨介质用量1500g（为原料质量的6倍）的反应条件下，制备得到二聚酸含量为79%、酸值为196mgKOH/g、黏度为1640mPa·s的二聚酸粗品，二聚酸产率为58.7%。相比于搅拌釜，球磨反应釜中二聚酸含量提高了75%。采用红外光谱（FTIR）、高效液相色谱-质谱（HPLC-Mass）等方法对产物进行表征，实验制得的二聚酸主要由双环二聚酸和无环二聚酸组成，双环二聚酸和无环二聚酸的比例为1.07∶1。

关键词: 聚合, 催化, 球磨, 制备, 二聚酸

CLC Number:

TQ644

HU Dongdong, QIAN Xing, JI Jianbing, LU Xianghong. Intensification of ball milling on the synthesis of dimer acid catalyzed by activated clay[J]. Chemical Industry and Engineering Progress, 2018, 37(05): 1902-1907.

胡冬冬, 钱行, 计建炳, 陆向红. 球磨法强化活性白土催化二聚酸合成[J]. 化工进展, 2018, 37(05): 1902-1907.

References

[1] 张树林.二聚酸的合成及工业应用[J].精细石油化工,1995(6):71-75. ZHANG S L. Synthesis and industrial application of dimer acid[J]. Speciality Petrochemicals,1995(6):71-75.
[2] 朱雷,陈坤雄,赵素英,等.CO₂环境下油酸聚合制二聚酸的工艺[J].化工进展,2013,32(9):2216-2220. ZHU L,CHEN K X,ZHAO S Y,et al.Process of oleic acid polymerization to dimer acid in CO₂ environment[J].Chemical Industry and Engineering Progress,2013,32(9):2216-2220.
[3] 高晓薇,韦藤幼,潘远凤,等.活性白土的化学改性及其作用机理研究[J].广西大学学报(自然科学版),2010,3(3):410-415. GAO X W,WEI T Y,PAN Y F,et al.Study on chemical modification of activated clay and its mechanism[J].Journal of Guangxi University(Natural Science Edition),2010,3(3):410-415.
[4] 陈坤雄.油酸聚合动力学及催化剂性能研究[D].福州:福州大学,2014. CHEN K X.Study on kinetics of oleic acid polymerization and catalytic performance[D].Fuzhou:Fuzhou University,2014.
[5] MJAMD O.The dimerization of oleic acid with a montmorillonite catalyst Ⅱ:GLC analysis of the monomer;the structure of the dimer;a reaction model[J].European Journal of Lipid Science & Technology,2010,72(10):875-883.
[6] 陈振华,陈鼎.机械合金化与固液反应球磨[M].北京:化学工业出版社,2006. CHEN Z H,CHEN D.Mechanical alloying and solid - liquid reaction milling[M].Bejing:Chemical Industry Press,2006.
[7] 陈渊,杨家添,黄祖强,等.机械活化固相化学反应制备木薯醋酸酯淀粉[J].食品与发酵工业,2013,39(7):135-141. CHEN Y,YANG J T,HUANG Z Q,et al.Preparation of cassava acetate starch by mechanical activation of solid - phase chemical reaction[J].Food and Fermentation Industries,2013,39(7):135-141.
[8] 陈鼎.固液反应球磨工艺及其原理研究[D].长沙:中南大学,2003. CHEN D.Study on the technology and principle of solid - liquid reaction[D].Changsha:Central South University,2003.
[9] LI H,WANG X,LIU C,et al.An efficient pretreatment for the selectively hydrothermal conversion of corncob into furfural:the combined mixed ball milling and ultrasonic pretreatments[J]. Industrial Crops & Products,2016,94:721-728.
[10] DELOGU F,GORRASI G,SORRENTINO A.Fabrication of polymer nanocomposites via ball milling:present status and future perspectives[J].Progress in Materials Science,2017,86:75-126.
[11] COCCO G,MULAS G,SCHIFFINI L.Mechanical alloying processes and reactive milling (Overview)[J]. Materials Transactions,1995,36(2):150-160.
[12] CHEN Z,CHEN D,CHEN G,et al.Preparation of elevated-temperature intermetallic powders via a novel reaction ball milling technique[J].Journal of Alloys & Compounds,2004,370(1/2):43-46.
[13] 冯光炷,崔英德,卢奎,等.自生压条件下三种催化剂对红花油脂肪酸二聚作用的影响[J].粮油加工与食品机械,2005(12):56-59. FENG G Z,CUI Y D,LU K,et al.Effect of three kinds of catalysts on the dimerization of fatty acid in safflower oil under self- pressurized condition[J].Machinery for Cereals Oil and Food Processing,2005(12):56-59.

[1]	ZHENG Qian, GUAN Xiushuai, JIN Shanbiao, ZHANG Changming, ZHANG Xiaochao. Photothermal catalysis synthesis of DMC from CO₂ and methanol over Ce_0.25Zr_0.75O₂ solid solution [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 319-327.
[2]	WANG Zhengkun, LI Sifang. Green synthesis of gemini surfactant decyne diol [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 400-410.
[3]	DENG Liping, SHI Haoyu, LIU Xiaolong, CHEN Yaoji, YAN Jingying. Non-noble metal modified vanadium titanium-based catalyst for NH₃-SCR denitrification simultaneous control VOCs [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 542-548.
[4]	GENG Yuanze, ZHOU Junhu, ZHANG Tianyou, ZHU Xiaoyu, YANG Weijuan. Homogeneous/heterogeneous coupled combustion of heptane in a partially packed bed burner [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4514-4521.
[5]	GAO Yanjing. Analysis of international research trend of single-atom catalysis technology [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4667-4676.
[6]	QIAN Sitian, PENG Wenjun, ZHANG Xianming. Comparative analysis of forming cyclic oligomers via PET melt polycondensation and cyclodepolymerization [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4808-4816.
[7]	LI Dongze, ZHANG Xiang, TIAN Jian, HU Pan, YAO Jie, ZHU Lin, BU Changsheng, WANG Xinye. Research progress of NO _x reduction by carbonaceous substances for denitration in cement kiln [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4882-4893.
[8]	WANG Chen, BAI Haoliang, KANG Xue. Performance study of high power UV-LED heat dissipation and nano-TiO₂ photocatalytic acid red 26 coupling system [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4905-4916.
[9]	CHEN Junjun, FEI Chang’en, DUAN Jintang, GU Xueping, FENG Lianfang, ZHANG Cailiang. Research progress on chemical modification of polyether ether ketone for the high bioactivity [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4015-4028.
[10]	HUANG Yufei, LI Ziyi, HUANG Yangqiang, JIN Bo, LUO Xiao, LIANG Zhiwu. Research progress on catalysts for photocatalytic CO₂ and CH₄ reforming [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4247-4263.
[11]	LI Runlei, WANG Ziyan, WANG Zhimiao, LI Fang, XUE Wei, ZHAO Xinqiang, WANG Yanji. Efficient catalytic performance of CuO-CeO₂/TiO₂ for CO oxidation at low-temperature [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4264-4274.
[12]	WU Haibo, WANG Xilun, FANG Yanxiong, JI Hongbing. Progress of the development and application of 3D printing catalyst [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 3956-3964.
[13]	GUO Lixing, PANG Weiying, MA Keyao, YANG Jiahan, SUN Zehui, ZHANG Pan, FU Dong, ZHAO Kun. Hierarchically multilayered TiO₂ with spatial pore-structure for efficient photocatalytic CO₂ reduction [J]. Chemical Industry and Engineering Progress, 2023, 42(7): 3643-3651.
[14]	CHU Tiantian, LIU Runzhu, DU Gaohua, MA Jiahao, ZHANG Xiao’a, WANG Chengzhong, ZHANG Junying. Preparation and chemical degradability of organoguanidine-catalyzed dehydrogenation type RTV silicone rubbers [J]. Chemical Industry and Engineering Progress, 2023, 42(7): 3664-3673.
[15]	LI Yanling, ZHUO Zhen, CHI Liang, CHEN Xi, SUN Tanglei, LIU Peng, LEI Tingzhou. Research progress on preparation and application of nitrogen-doped biochar [J]. Chemical Industry and Engineering Progress, 2023, 42(7): 3720-3735.