Beitrag zur Prüfung von Bedarfsgegenständen aus Plasten. Untersuchungen über die Auswanderung von Di‐n‐octyl‐(l‐<sup>14</sup>C)‐zinndithioglykolsäure‐2‐äthylhexylester aus Hart‐PVC in Speiseöl

Seidler, H.; Woggon, H.; Härtig, M.; Uhde, W.‐J.

doi:10.1002/food.19690130314

Cited by 12 publications

(3 citation statements)

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“…Unlike most asthma medications, the sodium salt of Montelukast can be taken orally in forms such as granulates, film, and chewing tablets . The foil commonly used as packaging for such tablets consists partially of PVC, which contains the thermal stabilizers dioctyltin bis(2-ethylhexyl thioglycolate) and monooctyltin tris(2-ethylhexyl thioglycolate). , These organotin compounds are introduced to prevent the thermal or light induced degradation of the PVC foil, during which polyenes are formed, and hydrochloric acid is released. , These stabilizers also play a role as traps for the released HCl, a process during which the tin compounds are chlorinated and 2-ethylhexyl thioglycolate is released (Figure ). , …”

Section: Introductionmentioning

confidence: 99%

“…4,5 These organotin compounds are introduced to prevent the thermal or light induced degradation of the PVC foil, during which polyenes are formed, and hydrochloric acid is released. 4,5 These stabilizers also play a role as traps for the released HCl, a process during which the tin compounds are chlorinated and 2-ethylhexyl thioglycolate is released (Figure 2). 5,6 During HPLC analysis of Montelukast chewing tablets, the presence of two formerly unknown impurities was detected.…”

Section: ■ Introductionmentioning

confidence: 99%

“…4,5 These stabilizers also play a role as traps for the released HCl, a process during which the tin compounds are chlorinated and 2-ethylhexyl thioglycolate is released (Figure 2). 5,6 During HPLC analysis of Montelukast chewing tablets, the presence of two formerly unknown impurities was detected. After isolation and NMR studies, these impurities were determined to be two stereoisomers formed by a Michaellike, thiol−ene addition of 2-ethylhexyl thioglycolate to the double bond present in Montelukast.…”

Section: ■ Introductionmentioning

confidence: 99%

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Formation of a Thiol–Ene Addition Product of Asthma Medication Montelukast Caused by a Widespread Tin-Based Thermal Stabilizer

Schmidt

Kolb

Reiser

et al. 2020

Chem. Res. Toxicol.

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We report the formation and characterization of two diastereomeric thiol–ene addition products of the asthma medication Montelukast within chewing tablets. Widespread tin-based thermal stabilizers dioctyltin bis(2-ethylhexyl thioglycolate) and monooctyltin tris(2-ethylhexyl thioglycolate), used in the manufacturing process of the medication’s forming foil, were identified as the source of the thiol reactant, showing that these stabilizers may play a part in the degradation of Montelukast and APIs with functionalities similar to those of Montelukast, which should be considered during development of medication. The isolation and analysis of these impurities was performed by HPLC and UV–vis spectroscopy. HRMS and NMR data were collected to characterize and determine the structures of these compounds.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Formation of a Thiol–Ene Addition Product of Asthma Medication Montelukast Caused by a Widespread Tin-Based Thermal Stabilizer

Schmidt

Kolb

Reiser

et al. 2020

Chem. Res. Toxicol.

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Untersuchungen zum Mechanismus der PVC‐Stabilisierung mit Organozinn‐Verbindungen

Figge¹,

Findeiss²

1975

Angew. Makromol. Chem.

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ZUSAMMENFASSUNG:Die derzeitigen Ansichten uber Startstellen, Mechanismen und Folgeprodukte der thermischen HCI-Abspaltung aus PVC werden kurz erortert.Die Kinetik der thermischen Dehydrochlorierung von unstabilisiertem und rnit 0,05 bis 2,O Gew.-% Di-n-octylzinn-di-thioglykolsaure-2-athylhexylester (I) stabilisiertem PVC The current views on starting positions, mechanisms and products resulting from thermal elimination of HCI from PVC, are briefly discussed.The kinetics of the thermal dehydrochlorination of unstabilized PVC as well as PVC stabilized with 0.05 to 2.0% by wt. of Di-n-octyl-tin-di-(2-ethylhexyl-thioglycolate) (I) have been investigated in detail. The rate of HCI-elimination from all PVC samples, as determined via conductivity measurements, was higher in air than under N2-atmosphere. After an initial period, which is characteristic for the stabilizer content of the respective sample, the rate of HCI elimination becomes constant, since no autocatalysis occurs via the eliminated HCI. In the beginning the velocity of HCI elimination decreases with increasing stabilizer content. The lowest value is reached at ca. 0.5% by wt. of the stabilizer, thereafter it remains constant. A similar tendency is shown in the case of the loss of weight of the samples as determined via thermogravimetry. The activation energy of PVC-degradation as well as the so-called 'maximum degradation temperature' reach their highest value (67 kcal/mol or 303°C respectively) at 0.5% by wt. of the stabilizer in PVC. Accordingly, there is an upper limit of the maximum effective stabilizer concentration in PVC. viz. about 0.5% by wt.Radio-tracer and ESCA-investigations show that the thioglycolic acid ester residues from I are incorporated into thermally stressed PVC, in form of sulfide-, sulfoxideand sulfonic structures, to the extent of 25X-independent of the stabilizer content of the samples. In the case of the n-octyl residue this is I 1 % by wt. of the stabilizer.Radio-GPC investigations show that the thioglycolic acid ester residues are preferentially linked to PVC molecules of shorter chain lengths. Since increasing amounts of stabilizer retard the discolouration of PVC, it is assumed that there is a direct relationship between the rate of incorporation of the ester residue and the PVC-discolouration.The stabilized, thermally stressed PVC absorbs a significantly larger amount of H 3 T 1 compared to pure or stabilized, untreated PVC respectively. Therefore, it can be assumed that HC1-polyen complexes or other complex structures having easily exchangable HCI or chloride ions, exist in stabilized, partially degraded polymers.

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Beitrag zur Prüfung von Bedarfsgegenständen aus Plasten. Zur Migration von PVC‐Stabilisatoren in Speiseöl

Woggon

Jehle

Uhde

1969

Nahrung

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Beitrag zur Prüfung von Bedarfsgegenständen aus Plasten. Untersuchungen über die Auswanderung von Di‐n‐octyl‐(l‐¹⁴C)‐zinndithioglykolsäure‐2‐äthylhexylester aus Hart‐PVC in Speiseöl

Abstract: In Fortfiihrung frfiherer Arbeiten wurde das Migrationsverhalten des fur die Verarbeitung von PVC eingesetzten Stabilisators Di-n-octyl-zinn-dithioglykolsiiure-z-athylhexylester gegenuber Speiseol mit Hilfe der Tracertechnik untersucht. Dazu wurde der

Cited by 12 publications

References 4 publications

Formation of a Thiol–Ene Addition Product of Asthma Medication Montelukast Caused by a Widespread Tin-Based Thermal Stabilizer

Formation of a Thiol–Ene Addition Product of Asthma Medication Montelukast Caused by a Widespread Tin-Based Thermal Stabilizer

Untersuchungen zum Mechanismus der PVC‐Stabilisierung mit Organozinn‐Verbindungen

Beitrag zur Prüfung von Bedarfsgegenständen aus Plasten. Zur Migration von PVC‐Stabilisatoren in Speiseöl

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Beitrag zur Prüfung von Bedarfsgegenständen aus Plasten. Untersuchungen über die Auswanderung von Di‐n‐octyl‐(l‐14C)‐zinndithioglykolsäure‐2‐äthylhexylester aus Hart‐PVC in Speiseöl

Abstract: In Fortfiihrung frfiherer Arbeiten wurde das Migrationsverhalten des fur die Verarbeitung von PVC eingesetzten Stabilisators Di-n-octyl-zinn-dithioglykolsiiure-z-athylhexylester gegenuber Speiseol mit Hilfe der Tracertechnik untersucht. Dazu wurde der

Cited by 12 publications

References 4 publications

Formation of a Thiol–Ene Addition Product of Asthma Medication Montelukast Caused by a Widespread Tin-Based Thermal Stabilizer

Formation of a Thiol–Ene Addition Product of Asthma Medication Montelukast Caused by a Widespread Tin-Based Thermal Stabilizer

Untersuchungen zum Mechanismus der PVC‐Stabilisierung mit Organozinn‐Verbindungen

Beitrag zur Prüfung von Bedarfsgegenständen aus Plasten. Zur Migration von PVC‐Stabilisatoren in Speiseöl

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Product

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Beitrag zur Prüfung von Bedarfsgegenständen aus Plasten. Untersuchungen über die Auswanderung von Di‐n‐octyl‐(l‐¹⁴C)‐zinndithioglykolsäure‐2‐äthylhexylester aus Hart‐PVC in Speiseöl