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In this study, the effect of hydrothermal liquefaction (HTL) of waste PVC was investigated in the presence of acidic hydrochar. The hydrochar was prepared by hydrothermal carbonization of pineapple waste at 250 °C and at 1 h in the presence of citric acid. Hydrochar was acidic, stable, and porous and contained acidic functional groups. Hydrochar was co-fed with PVC during HTL to enhance HTL conversion and quality of the plastic crude oil. HTL experiments were performed at 300–350 °C, 0.25–4 h of reaction times, and 0–20 wt% hydrochar-to-PVC ratio. The plastic crude oil was separated from the solid residue to evaluate HTL conversion and to analyze elemental compositions, boiling point distribution, alteration of chemical bonds, and chemical compositions. The results showed that acidic hydrochar enhances HTL conversion with a maximum value of 28.75 at 5 wt% hydrochar content at 350 °C and 0.5 h. Furthermore, plastic crude oils contained no chloride but contained significantly high carbon and hydrogen, resulting in a higher heating value of up to 36.43 MJ/kg. The major component of the plastic crude oil was 3, 5 dimethylphenol produced ranging from 61.4 to 86.4% (percentage of total identified area) according to gas chromatography mass spectroscopy (GCMS) data.