on poly(vinyl chloride) dehydrochlorination - Environmental Expert

J Mater Cycles Waste Manag (2006) 8:116–121 © Springer 2006 

DOI 10.1007/s10163-006-0154-9 

SPECIAL FEATURE: ORIGINAL ARTICLE 

Krzysztof German · Kamil Kulesza · Miriam Florack 

3rd International Symposium on Feedstock Recycling of 

Plastics & Other Innovative Plastics Recycling Techniques 

(ISFR 2005) 

Influence of poly(bisphenol A carbonate) and poly(ethylene terephthalate) 

on poly(vinyl chloride) dehydrochlorination 

Received: December 29, 2005 / Accepted: May 22, 2006 

Abstract Recycling of poly(vinyl chloride) (PVC) waste is 

a serious problem because of its high chlorine content. 

Dehydrochlorination of PVC-containing polymer waste 

produces solid residue char, for which conversion to 

pyrolysis oil in a petrochemical plant seems to be an attractive 

way of recycling PVC waste. Unfortunately, some 

polymer admixtures react with HCl and cause formation of 

chloroorganic compounds in a char. This article describes 

the influence of polycarbonates and poly(ethylene terephthalate) 

on thermal feedstock recycling of PVC wastes using 

a two-stage method. It was found that the presence of 

polycarbonate causes the formation of small amounts of 

benzyl chloride and other chloroaryl or chloroalkylaryl 

compounds. Poly(ethylene terephthalate) interacts with 

HCl forming significant amounts of various chlorocompounds 

– mainly chloroethyl esters of terephthalic and 

benzoic acids, but derivatives possessing chlorine directly 

connected to the aromatic ring are also formed. 

Key words PVC · BPA-based PC · PET · Recycling · 

Pyrolysis 

Introduction 

K. German 1 (*) · M. Florack 

Department of Chemistry and Technology of Polymers, Cracow 

University of Technology, Kraków, Poland 

K. Kulesza 

Blachownia Institute of Heavy Organic Synthesis, Kędzierzyn-Koźle, 

Poland 

Present address: 

1 Politechnika Krakowska, Samodzielna Katedra Chemii i Technologii 

Tworzyw Sztucznych, ul. Warszawska 24, 31–155 Kraków, Poland 

Tel. +48-12-628-21-14; Fax +48-12-628-20-38 

e-mail: kfgerm@chemia.pk.edu.pl 

The disposal of plastic wastes will become an important part 

of the chemical industry because of the large quantities of 

plastics produced and their environmental impact.Chlorinecontaining 

polymers cause problems during material or 

energetic recycling because of their decomposition with the 

evolution of HCl. The most commonly used chlorinecontaining 

polymer is poly(vinyl chloride) (PVC), the 

decomposition of which considerably limits material 

recycling due to the deterioration of its properties: 

–CH 2 –CHCl– mers eliminate HCl under the influence of 

heat (or light) and the PVC becomes yellowish or even 

blackish and loses its plasticity. Such waste can be used as a 

raw material for pyrolysis or for gasification. The choice 

between these two methods depends on the amount of chlorine 

in the char residue derived from a mixture of plastics 

after HCl elimination from PVC. In this article we present 

gas chromatography (GC) results after the thermal treatment 

of pure PVC and of PVC mixtures with poly(ethylene 

terephthalate) (PET) and with polycarbonate (PC). 

Two main, mostly nonoverlapping, stages of mass loss are 

observed during the thermal analysis of PVC. 1,2 In one 

series of experiments 0.5g samples of pure PVC underwent 

a dehydrochlorination (DHC) reaction at temperatures of 

up to 400°C. DHC was dicontinued when the char was free 

of chlorine (to the accuracy of conductometric analysis of 

eliminated HCl). DHC was followed by pyrolysis, which 

mainly formed aromatic hydrocarbons – chloroorganic 

compounds were not found by gas chromatography coupled 

with mass detector (GC-MS) analysis. 2 In contrast, Tromp 

et al. 3 found chlorobenzene and methylchlorobenzene 

after pyrolysis; however, it is not clear whether formation 

of these compounds resulted from admixtures present in the 

sample. 

Segregation methods for plastic wastes that are acceptable 

from the economical point of view do not guarantee 

100% selectivity. If density difference is applied as the segregation 

factor, PET remains in the PVC plastic fraction 

(Table 1). Other polymers having a lower density will also 

be present in this fraction; such polymers are usually filled 

with inorganic additives (e.g., polycarbonates). Both the 

polymers PET and PC can react with HCl to form 

chloroderivatives, which then contaminate the pyrolysis 

products of the char residue. The aim of our investigations 

is the identification of such compounds.

117 

Over the past decade, considerable progress has been 

reported in the development of methods of dechlorination 

of pyrolysis oil, 4–13 but not all the problems have been 

solved as yet. Complete dechlorination is hard to realize if 

the dehydrochlorinated mixture also contains polyesters 

(e.g., PET). Some of the consecutive HCl reactions that 

occur during the heating of these mixtures are yet to be elucidated. 

The goal of this work is to make progress in this 

area. 

The thermal degradation of PVC has already been the 

subject of numerous investigations. Some attention has also 

been paid to the thermal degradation of PET 14–16 and 

PC, 17–22 but the behavior of PVC–PET mixtures and especially 

the interaction of PVC with PC have been less 

studied. The dehydrochlorination of PVC starts at temperatures 

of about 100°C lower than for PET and, if the polymers 

are degraded separately, PVC is almost completely 

degraded before the temperature is reached at which PET 

starts to degrade (Fig. 1); however, the presence of HCl 

accelerates PET degradation if the polymers are mixed. 

The influence of PVC (mainly HCl from PVC) on the 

composition of the products of PET pyrolysis was discussed 

Table 1. Density of selected polymers 

Polymer Abbreviation Density (g/cm 3 ) 

Polyolefines PE, PP 0.89–0.97 

Polystyrene PS 1.04–1.08 

Polyamide PA 1.03–1.15 

Polyurethane elastomers PU 1.10 

Poly(methyl methacrylate) PMMA 1.18 

Polycarbonate PC 1.20 

(filled with glass fibers) 1.42 

Poly(vinyl chloride) PVC 1.38–1.55 

(plastificated) 1.19–1.38 

Poly(ethylene terephthalate) PET 1.38–1.41 

Polytetrafluorethylene PTFE 2.20 

in one of our previous papers, 23 but our knowledge concerning 

this process has increased since that time.The interaction 

between PVC and PET was also taken into account 

in an article in which the pyrolysis of a selected mixture 

of plastics [intended to simulate municipal plastic waste 

(MPW)] was described 8 .The article describes the results of 

gas chromatography coupled with atomic emission detector 

(GC-AED) analysis, as well as showing C-NP grams based 

on gas chromatography coupled with flame ionization 

detecter (GC-FID) results and selected results of the GC- 

MS analysis, which agree with the results of our model 

experiments. In the above work, 8 Bhaskar, with coworkers 

from the Sakata group, also reported the presence of some 

chloroalkyl esters; however, identification of the particular 

halogen compounds was not the goal of that work and 

detailed results were not given. Complex plastic mixtures, 

which also contain other halogen-containing polymers, 

for example high impact polystyrene flame retarded with 

bromine compounds (HIPS-Br) or chlorinated PVC and 

poly(vinylidene dichloride) (PVDC) have been intensively 

investigated (e.g., by Bhaskar et al. 9 and Jakab et al. 24 ). In 

our opinion, apart from the very important general experiments 

as described above, there is still a requirement for 

basic studies that seek for an explanation of the formation 

pathways of halogen-containing compounds in more complex 

mixtures of plastic waste. 

Fast degradation of PET starts at temperatures around 

350°C. No volatile products of thermal degradation of 

bisphenol A-based polycarbonate (BPA–PC) in an inert 

atmosphere were obtained up to 400°C. 17,18 It was found 

that product composition depended on the reaction 

medium – alkali media catalyze rearrangement reactions, 

whereas acids and other substances with active hydrogen 

atoms induce depolymerization. 19 Investigations of the 

pyrolysis of PVC–PC mixtures have not so far been 

reported. It is expected that the thermochemical de- 

0 

-1.6 

0 

0 

Mass loss of PVC sample 

-1 

-2 

-3 

-4 

TG - curve 

DTG - curve 

-1.8 

-2.0 

-2.2 

-2.4 

1 st derivative [mg/min] 

Mass loss of PET sample [mg] 

-1 

-2 

-3 

-4 

-5 

-6 

-7 

-8 

TG - curve 

DTG - curve 

-1 

-2 

-3 

-4 

-5 

1 st derivative [mg/min] 

-5 

0 100 200 300 400 500 

Temperature [°C] 

-2.6 

-9 

0 100 200 300 400 500 

Temperature [°C] 

-6 

Fig. 1. Thermogravimetric (TG) and derivative thermogravimetric (DTG) curves of poly(vinyl chloride) (PVC) and poly(ethylene terephthalate) 

(PET) degradation in an inert atmosphere

118 

gradation of BPA–PC should be observed in the presence 

of HCl. 

Experimental 

Materials 

Poly(vinyl chloride) (PVC S-70) was acquired from Anwil 

(Wl′ocl′awek, Poland), the BPA-based polycarbonate 

LEXAN was provided as waste plastic by Telkom- 

Telos (Kraków, Poland), analytical grade carbon disulfide 

was from Riedel-de Haën (Seelze, Germany), HPLC-grade 

dichloromethane was from Aldrich (Steinheim, Germany), 

and active carbon samples from SKC (Dorset, UK). 

acid and biphenyl. Moreover, small amounts of other compounds 

were identified, as shown in Fig. 3. The retention 

time of acetaldehyde was less than 14min. 

The product composition of the pyrolysis of PET 

changed radically in the presence of PVC (HCl), which 

caused the formation of a great number of organic 

chloroderivatives. It is clear that the amount of these compounds 

produced depends on the proportion of PVC to 

PET in the dehydrochlorinated and then pyrolyzed samples. 

High chlorine content was the goal of our work because it 

makes for easier product identification, so we used 1:1 

(w/w) PVC–PET mixtures. In real-life waste mixtures there 

will be less PET than PVC. 

Table 2. Pyrolysis products of PVC char residue at 550°C 

Techniques 

Dehydrochlorination and pyrolysis were conducted in a 

purpose-built pyrolysis setup, as shown in Fig. 2. Samples 

weighed between 10 and 50g and the temperature was measured 

by a NiCr–NiAl thermocouple. Pyrolysis products 

were transported by nitrogen as a carrier gas into a glass 

condenser system (air and water cooler) with an active 

carbon adsorber and water scrubber located at the 

polypropylene off-gas pipe. Dehydrochlorination was performed 

at 350°C for 90min and was followed by pyrolysis 

at 500°C for 90min.The pyrolysis of PC and PET separately 

was performed for comparison under the same conditions 

(90min at 350°C followed by 90min at 500°C). Condensed 

pyrolysis products were dissolved in CH 2 Cl 2 ; products 

adsorbed on active carbon were extracted by 4cm 3 of CS 2 . 

The solutions were analyzed by gas chromatography 

coupled with a quadruple mass detector (GC-MS, HP 8590 

Series 2 equipped with 30m HP-1 column) using helium as 

the carrier gas. 

Results and discussion 

Our early work on PVC dehydrochlorination and pyrolysis 

gave us much information about contaminations of the 

derived oil (Table 2); however, when pure polymer was 

used, we detected no chloroorganic compounds. The oil 

fraction from the pyrolysis of PET contains mainly benzoic 

Pyrolysis product; R = H, alkyl Molar ratio C/H Peak area (%) 

R 

R 

R 

R 

R 

R 

R 

1 2 

1 3 

>1 1 

>1 to 1 11 

>1 2 

>1 4 

>1 2 

R 

R 

>1 2 

Unidentified 15 

Abundance 

TIC: MF6.D 

4000000 

3500000 

3000000 

COOH 

COOH 

O 

2500000 

2000000 

1500000 

1000000 

500000 

COOH 

Time--> 

0 

14.00 16.00 18.00 20.00 22.00 24.00 26.00 

O 

CH 

o-terphenyl 

C 18 H 14 

C 14 H 10 

C 18 H 14 

Fig. 2. Experimental setup for pyrolysis 

Fig. 3. Result of GC-MS analysis of liquid products formed during 

PET pyrolysis

119 

Table 3. Chloroorganic products of PVC–PET 1 : 1 (w/w) mixture pyrolyzed at 450°C 

Chloroorganic compounds Peak area share (%) 

Chlorine in an aliphatic moiety 

Methane, bis(2-chloroethoxy) 0.8 

Chlorine in an aliphatic moiety of benzoic acid esters 

Benzoic acid, 2-chloroethyl ester 11.2 

4-Methyl and 4-formyl benzoic acid, 2-chloroethyl esters 8.5 

Chlorine in an aliphatic moiety of 1,4-benzenedicarboxylic acid esters 

1,4-Benzenedicarboxylic acid, mono-2-chloroethyl esters 18.8 

1,4-Benzenedicarboxylic acid, bis-(2-chloroethyl ester) 30.6 

Chlorine in an aromatic ring 

3- and 4-Chlorobenzoic acid, ethyl ester 0.3 

Chlorine in an aromatic ring and in an aliphatic moiety 

4-Chlorobenzoic acid, 2-chloroethyl ester 0.4 

CH2CH2OOC 

COOCH2CH2OOC 

COOCH2CH2OH 

Abundance 

1.5e+07 

1.4e+07 

TIC: [BSB1]MF5.D 

1.3e+07 

1.2e+07 

HCl 

1.1e+07 

1e+07 

9000000 

8000000 

CH2CH2OOC COOH + ClCH2CH2OOC COOCH2CH2OH 

7000000 

6000000 

5000000 

4000000 

3000000 

HCl 

+HCl 

- H2O 

2000000 

1000000 

Time--> 

0 

5.00 10.00 15.00 20.00 25.00 30.00 

CH2CH2Cl + HOOC 

COOH 

ClCH2CH2OOC 

COOCH2CH2Cl 

Fig. 5. Chromatogram of the products of polycarbonate (PC) 

pyrolysis 

COOCH2CH2OOC 

COOCH2CH2Cl 

Abundance 

5500000 

5000000 

OH 

TIC: MF7.D 

OH 

HCl 

4500000 

4000000 

3500000 

O 

COOH 

+ 

ClCH2CH2OOC 

COOCH2CH2Cl 

3000000 

2500000 

2000000 

Fig. 4. Formation of chloroderivatives from PET in the presence of 

HCl 

1500000 

1000000 

500000 

0 

Time--> 

5.00 10.00 15.00 20.00 25.00 30.00 

Fig. 6. GC-MS result of analysis of pyrolysis products of dehydrochlorinated 

PVC-PC (1:1 w/w) mixture 

Some of the chlorine compounds derived are specified in 

Table 3. Identification of these compounds was described 

in an earlier paper. 23 A possible formation pathway of 

chloroderivatives from PET in reaction with HCl is 

presented in Fig. 4. HCl attacks the ester bond and a 

transesterification reaction leads to formation of the 

–COOC 2 H 4 Cl group. The atypical structure of 

–COOC 2 H 4 Cl and the relatively high probability of its formation 

are sources of the problems with dechlorination of 

pyrolysis oil derived from PVC-containing PET. It is noteworthy 

that chloroorganic derivatives (for example 3- 

chlorobenzoic acid and 4-chlorobenzoic acid) are formed 

not only in the transesterification reaction of polyester and 

HCl; compounds that include the formyl group, the alkyl 

group, or chlorine connected to an aromatic ring can be 

formed by consecutive reactions after decarboxylation of 

terephthalic acid mono-2-chloroethyl ester. 

A chromatogram of the oil fraction obtained during 

pyrolysis of PC is presented in Fig. 5. We did not find fluorenone 

or xanthone derivatives – in contrast to the results 

described in other works 19,21 – and this fact can be explained 

by the absence of basic catalysts in the reaction medium. 

A chromatogram of the oil fraction produced by pyrolysis 

of a 1:1 (w/w) PC–PVC mixture is shown in Fig. 6. 

The main products of pyrolysis of a dehydrochlorinated 

PVC–PC mixture are phenol, 4-isopropylphenol, and 1- 

isopropyl-4-phenoxybenzene. Our results confirm the findings 

regarding the influence of an acidic medium on the 

mechanism of thermal degradation of PC. 

Among the pyrolysis products condensed in oil fractions 

derived under the previously described DHC and pyrolysis 

conditions, we did not find the chlorine derivatives 

predicted by the reaction scheme shown in Fig. 7. We did 

find a number of these compounds among the products

120 

adsorbed on active carbon, but some of them were in 

isomerized form. A chromatogram of these products is presented 

in Fig. 8. The area of the peaks of all chlorocompounds 

that were identified by GC analysis is about 2%–3% 

H 

O 

O 

O 

C 

O 

HCl 

O 

O 

C 

+ 

C 

HCl 

Cl 

O 

C 

H Cl + 

C 

HCl 

H 

H 

HCl 

O 

O 

HCl 

-CO2 

HCl 

Cl 

O H + CO2 + 

Fig. 7. Potential pathways for chloroderivative formation during the 

interaction of PC and HCl 

Abundance 

1.5e+07 

1.4e+07 

1.3e+07 

1.2e+07 

1.1e+07 

1e+07 

9000000 

8000000 

7000000 

6000000 

5000000 

4000000 

3000000 

2000000 

1000000 

0 

Time--> 

Cl 

Cl 

Cl 

+ 

Cl 

CH 2 

Cl 

+A 

5.00 10.00 15.00 20.00 25.00 30.00 

+ 

TIC: MF9G1.D 

OH + 

Cl 

C 

Cl 

Cl 

+ 

(treaces) 

Fig. 8. Chromatogram of products formed during pyrolysis of PVC–PC 

(1 : 1 w/w mixture) adsorbed on active carbon 

Cl 

Cl 

Cl 

C 

C 

C 

HCl 

Cl 

+ 

HCl 

A 

of the total area, but based on this it is not possible to say 

whether the ratio of chlorine in the oil fraction from pyrolysis 

of PVC–PC mixtures exceeds the technological threshold 

of 10ppm, even though the amount of PC in waste 

mixtures is much lower than in our mixture. Identification 

of chlorine derivatives by means of GC-MS requires 

close attention because of the masking effect of Cl-isotopes 

by signals resulting from other fragmentation paths, 

especially when some compounds are not separated in the 

GC column. For example, it was not possible to detect 

the presence of 4-chlorophenol using only analytical standards 

because signals of this chloroderivative were masked 

by the signals of naphthalene. We did not separate 

these substances in our chromatograph column. Benzene 

dichloride and benzyl chloride were also not separated 

because of their similar vapor pressures, but they give 

characteristic signals at slightly different retention times 

(Fig. 9). 

Pyrolysis of PVC–PET–PC (1:1:1) mixtures did not 

reveal new chlorine-containing compounds, but the analysis 

has not yet been completed because of its complexity. 

Conclusions 

PET interacts with HCl forming large amounts of 

chloroderivatives, mainly chloroethyl esters of terephthalic 

acid and of benzoic acid but also compounds with chlorine 

in the benzene ring. Pyrolysis of BPA-based polycarbonate 

produced 4-methylphenol, 4-ethylphenol, 4-isopropylphenol, 

4-(1-methyl-1-phenylethyl) phenol, 1-isopropyl-4- 

phenoxybenzene, BPA, and small amounts of other 

compounds. HCl evolved during the dehydrochlorination of 

PVC–PC mixtures changes the composition of PC degradation 

products – mainly phenol, isopropylphenol, and 

1-isopropyl-4-phenoxy-benzene are produced. Polyesters 

Fig. 9. Profile of characteristic 

fragmentation signals of 

benzene dichloride and benzyl 

chloride 

Abundance 

100000 

50000 

0 

Time--> 

Ion 146.00 (145.70 to 146.70): MF9G1.D 

10.30 10.40 10.50 10.60 10.70 10.80 

Abundance 


100000 

50000 

0 

Time--> 

10.30 10.40 10.50 10.60 10.70 10.80 

Abundance 


100000 

50000 

0 

Time--> 

10.30 10.40 10.50 10.60 10.70 10.80 

Abundance 


100000 

50000 

0 

Time--> 

10.30 10.40 10.50 10.60 10.70 10.80

121 

show interaction with HCl at temperatures below 350°C. 

These secondary reactions during thermal degradation of 

PVC–PC mixtures produce small amounts of halogen derivatives 

such as chlorobenzene, 1,4-dichlorobenzene, benzyl 

chloride, 4-chlorophenol, and isopropylchlorobenzene. The 

diversity of these substances proves that a universal method 

is necessary to eliminate the chlorine content from char 

residue or from pyrolysis oil. 

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