聚氯乙烯(Polyvinyl chloride，PVC)作为全球第三大通用合成树脂，被广泛应用于国民经济的各个领域。塑化剂是柔性PVC中最主要的添加剂，邻苯二甲酸酯类(Phthalates, PAEs)塑化剂用量最多，其中邻苯二甲酸(2-乙基)己酯(Di-(2-ethylhexyl) Phthalate，DEHP)占50%。另外，PVC中还含有大量的氯。PVC废弃后不仅污染环境，还会威胁人类的健康，但由于氯和塑化剂含量较高，处理和资源化利用PVC废物面临巨大挑战。同时，高氮尿液废水、含镍电镀废水和油泥，这些废水、固体废弃物的无害化处理也被广泛关注。本论文分别将尿液废水、含油污泥与含镍电镀废水联合富DEHP柔性PVC废物共处理，构建了亚临界尿液废水(Subcritical urine wastewater，SUW)–PVC、亚临界水-含油污泥(Subcritical water - oily sludge，SW–OS)–PVC和亚临界含镍电镀废水(Subcritical nickel electroplating wastewater，SNEW)–PVC三个处理工艺，主要结果如下：

(1) 在SUW–PVC工艺中，通过富DEHP的PVC废物和尿液废水协同处理，可同步实现了PVC废物脱氯、DEHP分解和尿液废水脱氮的效果。①对于新鲜尿液废水，在最佳条件(300 ℃、15 min、1:5 g/mL)下，PVC废物脱氯率、尿液废水脱氮率和DEHP分解率分别可达98.4%、64.9%和99.2%。DEHP的分解主要包括水解、亲核取代和酰胺化。DEHP可在220 ℃转化为邻苯二甲酸晶体，产率为66.25%。羟基亲核取代是PVC的主要脱氯途径，脱除的氯全部从PVC基质转移到水相中。SUW中含氮物质与DEHP之间的反应有利于尿液废水的高效脱氮，氮元素被固定在固体残留物中或作为酰胺化合物转移到油相中。②对于水解尿液废水，温度以及固液比对脱氮作用影响不大，长停留时间有利于提高脱氮效果。在220 ℃(45 min、1:5 g/mL)时PVC废物的脱氯率为95.8%，尿液废水的脱氮率(50.7%)和DEHP的分解率(43.6%)较低。在300 ℃、15 min、1:5 g/mL条件下，PVC废物脱氯率、尿废水脱氮率及DEHP分解率分别是98.6%、59.7%和 100%。PVC废物的脱氯途径主要是羟基亲核取代和消去反应，羟基会进一步脱水羰基化，消去反应形成的不饱和键在氧介导作用下形成羰基或羧基，进一步被氨基取代，形成酰胺类物质。尿液废水中脱除的氮全部固定在固相残渣中，DEHP分解为苯甲酸、2-乙基-1-己醇、3-甲基-3-庚醇和苯酚。

(2) 在SW–OS–PVC工艺中，油泥与富DEHP塑化剂PVC废物在亚临界水中共反应，可同步实现PVC废物脱氯、DEHP分解及油泥分解。富DEHP塑化剂PVC废物与油泥的协同处理，在350 ℃(1 h、1:5 g/mL、油泥/PVC: 3/1)条件下，PVC废物可完全脱氯，同时促进油泥的分解，油泥将近69种的复杂化合物被降解为仅6种物质的高附加值油，含轻质油(31.74%)和3-乙基-己烯(34.44%)。反应时间过长会抑制PVC废物的脱氯及固体废物的减重效果，1小时为最佳时间。油泥与PVC废物的质量比对SW-OS处理效果影响较为显著，当油泥与PVC废物比值为1:3时，油泥产出轻质油的温度可降低到325℃，且可得到大量的苯甲酸（50.87%）。PVC废物的脱氯途径被认为是羟基亲核取代和消去反应分步进行的，300 ℃时主要以羟基亲核取代为主；325 ℃时羟基亲核取代和消去反应共存；随着温度升高，350 ℃时羟基亲核取代行为增强，消去反应逐渐减弱。

(3) 在SNEW–PVC工艺中，含镍电镀废水作为反应介质与富DEHP塑化剂PVC废物共反应，高温、短时间以及较大的固液比对PVC废物脱氯有利。SNEW工艺对含镍电镀废水中Ni²⁺ 的去除效果较好，温度及反应时间对PVC废物的碳化程度、团聚程度以及减重效果影响较大。含镍电镀废水中的Ni²⁺ 对PVC废物的脱氯有着促进作用，可促进PVC废物基质多孔结构的形成，有利于PVC废的传热与传质。在250 ℃、15 min、1:5 g/ml条件下，PVC脱氯率为83.93%，延长时间到30分钟对PVC废物脱氯有促进作用(90.21%)。过长的反应时间 (60 min)或固液比过小(1:15 g/mL)会导致PVC废物基质孔隙堵塞，降低脱氯效果。PVC废物的脱氯机制为羟基亲核取代和消去反应，羟基进一步羰基化，烯烃在氧介导作用下也会产生羰基。在含镍电镀废水中，Ni²⁺ 既发生氧化反应生成NiO₂，又发生还原反应生成Ni，并被PVC废物残渣吸附，高附加值化合物可通过分离提纯再利用。

Polyvinyl chloride (PVC), as the third largest universal synthetic resin in the world, is widely used in various economic fields. Plasticizer is the most important additive in flexible PVC, with phthalates (PAEs) having the highest dosage of plasticizers, with Di - (2-ethylhexyl) phthalate (DEHP) accounting for 50%. At the same time, PVC also contains a large amount of chlorine. The waste of PVC not only pollutes the environment but also poses a threat to human health. However, due to the high content of chlorine and plasticizers, the treatment and resource utilization of PVC waste face enormous challenges. At the same time, the harmless treatment of high nitrogen urine wastewater, nickel containing electroplating wastewater, and oil sludge, as well as solid waste, has also received widespread attention. This paper co treated urine wastewater, oily sludge, and nickel containing electroplating wastewater with rich DEHP flexible PVC waste, and constructed three treatment processes: subcritical urine wastewater (SUW)-PVC, subcritical water oily sludge (SW-OS)-PVC, and subcritical nickel electroplating wastewater (SNEW)-PVC. The main results are as follows:

(1) In the SUW-PVC process, the collaborative treatment of PVC waste rich in DEHP and urine wastewater simultaneously achieves dechlorination of PVC waste, decomposition of DEHP, and denitrification of urine wastewater.For fresh urine wastewater, under the optimal conditions (300 ℃, 15 min, 1:5 g/mL), the dechlorination rate of PVC waste, denitrification rate of urine wastewater, and DEHP decomposition rate can reach 98.4%, 64.9%, and 99.2%, respectively. The decomposition of DEHP mainly includes hydrolysis, nucleophilic substitution and amidation. DEHP can be converted into phthalic acid crystals at 220 ℃ with a yield of 66.25%. Hydroxyl nucleophilic substitution is the main dechlorination route of PVC, and all the chlorine removed is transferred from the PVC matrix to the aqueous phase. The reaction between nitrogen containing substances in SUW and DEHP is conducive to efficient denitrification of urine wastewater, and nitrogen elements are fixed in solid residues or transferred to the oil phase as amide compounds. For hydrolyzed urine wastewater, temperature and solid-liquid ratio have little effect on denitrification, and long residence time is beneficial for improving denitrification efficiency. At 220 ℃ (45 min, 1:5 g/mL), the dechlorination rate of PVC waste is 95.8%, while the denitrification rate of urine wastewater (50.7%) and the decomposition rate of DEHP (43.6%) are relatively low. Under the conditions of 300 ℃, 15 min, and 1:5 g/mL, the dechlorination rate of PVC waste, denitrification rate of urine wastewater, and DEHP decomposition rate are 98.6%, 59.7%, and 100%, respectively. The dechlorination path of PVC waste is mainly the hydroxyl nucleophilic substitution and elimination reaction. The hydroxyl will further dehydrate carbonylation, and the unsaturated bond formed by the elimination reaction will form carbonyl or carboxyl under the oxygen mediated action, which will be further replaced by amino to form amide substances. All nitrogen removed from urine wastewater is fixed in solid residue, and DEHP is decomposed into benzoic acid, 2-ethyl-1-hexanol, 3-methyl-3-heptanol and phenol.

(2) In the SW-OS-PVC process, oil sludge reacts with PVC waste rich in DEHP plasticizer in subcritical water, and the dechlorination, DEHP decomposition, and oil sludge decomposition of PVC waste can be achieved simultaneously. The synergistic treatment of PVC waste rich in DEHP plasticizer and oil sludge results in complete dechlorination of PVC waste at 350 ℃ (1 h, 1:5 g/mL, oil sludge/PVC: 3/1), while promoting the decomposition of oil sludge. The oil sludge is degraded from nearly 69 complex compounds to only 6 high value-added oils, containing light oil (31.74%) and 3-ethylhexene (34.44%). If the reaction time is too long, it will inhibit the dechlorination of PVC waste and the weight reduction effect of solid waste, with 1 hour being the best. The quality ratio of oil sludge to PVC waste has a significant impact on the SW-OS treatment effect. When the ratio of oil sludge to PVC waste is 1:3, the temperature of light oil produced by the oil sludge decreases to 325 ℃, and 50.87% benzoic acid can be obtained. The dechlorination of PVC waste is considered to be a step by step process of hydroxyl nucleophilic substitution and elimination reaction. At 300 ℃, hydroxyl nucleophilic substitution is the main way; At 325 ℃, hydroxyl nucleophilic substitution and elimination reactions coexist; With the increase of temperature, the nucleophilic substitution behavior of hydroxyl group increases and the elimination reaction weakens gradually at 350 ℃.

(3) In the SNEW-PVC process, nickel containing electroplating wastewater is used as a reaction medium to co react with PVC waste rich in DEHP plasticizer. High temperature, short time, and large solid-liquid ratio are beneficial for dechlorination of PVC waste. The SNEW process has a good removal effect on Ni²⁺ in nickel containing electroplating wastewater. Temperature and reaction time have a significant impact on the degree of carbonization, agglomeration, and weight reduction of PVC waste. The Ni²⁺ in nickel containing electroplating wastewater has a promoting effect on the dechlorination of PVC waste. Ni²⁺ can promote the formation of porous structures in the PVC waste matrix, which is beneficial for the heat and mass transfer of PVC waste. Under the conditions of 250 ℃, 15 minutes, and 1:5 g/ml, the dechlorination rate of PVC was 83.93%. Prolonged time (30 min) had a promoting effect on the dechlorination of PVC waste (90.21%). Long reaction time (60 min) or low solid-liquid ratio (1:15 g/mL) can lead to pore blockage in the PVC waste matrix, reducing the dechlorination effect. The dechlorination mechanism of PVC waste is hydroxyl nucleophilic substitution and elimination reaction. The hydroxyl is further carbonylation, and olefins will also produce carbonyl under the oxygen mediated action. The Ni²⁺ in nickel containing electroplating wastewater undergoes both oxidation reaction to generate NiO₂ and reduction reaction to generate Ni, which is adsorbed by PVC waste residue. High value-added compounds can be separated, purified, and reused.

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