Detailed investigation of fluoromethyl 1,1,1,3,3,3-hexafluoro-2-propyl ether (sevoflurane) and its degradation products. Part I: Synthesis of fluorinated, soda lime induced degradation products

Huang, Chialang; Venturella, Vincent S.; Cholli, Ashok L.; Venutolo, Felicia M.; Silbermann, Adrea T.; Vernice, Gerald G.

doi:10.1016/s0022-1139(00)84149-4

Cited by 23 publications

(5 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Gas chromatography combined with mass spectroscopy (Hewlett Packard 5890 with MSD 5971A) was used for identification of gas components and purity check of compound A (CH 2 F-O-C(ϭCF 2 ) (CF 3 )). Compound A was synthesized by one of the investigators (M. G. 9 ) and characterized by 1 H-NMR, 13 C-NMR, CH analysis and IR spectroscopy. Measurement of CH 3 OH and compound A was achieved by GC-FID detection using a Fisons 8000 equipped with a 50-µl heated (70°C) injection loop, a 2 m/0.53 mm id deactivated fused silica transfer line (Alltech, Munich, Germany), a Supel-Q Plot 30 m/0.53 mm id capillary column (Supelco, Bellafonte, USA) and a carrier pressure of 100 kPa (helium).…”

Section: Analysesmentioning

confidence: 99%

Dry soda lime markedly degrades sevoflurane during simulated inhalation induction

Funk

Gruber

Wild

et al. 1999

British Journal of Anaesthesia

View full text Add to dashboard Cite

We have investigated gas composition during simulated inhalation induction with sevoflurane to elucidate possible mechanisms of incidental prolonged induction times and airway irritation. Using a circle system, 8% sevoflurane in oxygen 6 litre min-1 was washed into an absorbing canister filled with fresh soda lime containing 2.9% KOH (Draegersorb, 'D') or no KOH (< 0.01%, Sofnolime, 'S'). The absorbent was dried by oxygen 20,000 litre before every second experiment. Maximum soda lime temperatures attained after 4-6 min were 107 degrees C using dry D and 62 degrees C (61 degrees C) with dry S. Temperature did not increase with fresh soda lime. With dry soda lime, sevoflurane was not detected at the T-piece for 3 min and reached 6-7% within 6-10 min. After 1 min, we detected methanol and compound A (CH2F-O-C(= CF2) (CF3)). Total amounts over 20 min were: methanol 1125 mg (D dry), 334 mg (S dry) and < 5 mg (fresh soda lime); compound A 148 mg (D dry), 13 mg (S dry) and 3-8 mg (fresh); and fluoride 8.5 mg (D dry), 3.3 mg (S dry) and 1 mg (fresh). Formaldehyde was detected only with dry lime (D > 2.5 mg, S > 0.6 mg). In summary, the use of moist soda lime is of crucial importance during inhalation induction. With dry soda lime, the patient may inhale potentially toxic degradation products in significant amounts. Sevoflurane degradation is aggravated by a high KOH content of the lime. The observed airway irritation may be caused by formic acid, which is generated in isomolar concentrations with methanol (Cannizzaro reaction). The amount of compound A found with dry KOH-containing lime is unlikely to be noxious.

show abstract

Section: Analysesmentioning

confidence: 99%

Dry soda lime markedly degrades sevoflurane during simulated inhalation induction

Funk

Gruber

Wild

et al. 1999

British Journal of Anaesthesia

View full text Add to dashboard Cite

show abstract

“…The refractive index at 30 °C was determined to n D ) 1.29. The racemic mixture of halodiether B was prepared according to a modified method 18 described by Huang et al 33 The refractive index at 30 °C was determined to n D ) 1.325. The polysiloxane PS255 (polydimethyl-(0.5-1%)-methylvinylsiloxane copolymer) was obtained from ABCR (Karlsruhe, Germany).…”

Section: Methodsmentioning

confidence: 99%

Use of a Modified Cyclodextrin Host for the Enantioselective Detection of a Halogenated Diether as Chiral Guest via Optical and Electrical Transducers

et al. 2002

View full text Add to dashboard Cite

In an alkaline rebreathing circuit, the inhalation anesthetic sevoflurane degrades into at least two products, one of them being the chiral halodiether 1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane (halodiether B). Using octakis(3-O-butanoyl-2,6-di-O-n-pentyl)-y-cyclodextrin (Lipodex E) as chiral host diluted in the polysiloxane PS255, an exceptional large chiral separation factor alpha of 9.7 at 30 degrees C was found for halodiether B by capillary gas chromatography (cGC). Hence, the interaction of the single enantiomers and the racemic mixture of the halodiether B with Lipodex E was selected as a model system to study the enantioselective recognition by thickness shear mode resonators (TSMR), surface acoustic wave sensors, surface plasmon resonance (SPR), and reflectometric interference spectroscopy. Further investigations of the recognition process by using chemical sensors confirmed the preferential enrichment of the S-enantiomer resulting in 9-fold higher signals. Based on the distinction between enantioselective and nonenantioselective sorption, thermodynamic complexation constants of the single enantiomers with Lipodex E could be determined. The difference in Gibbs free energy -deltaE2,E1(deltaG) of the complexation of the enantiomers of halodiether B with pure Lipodex E was determined at 30 degrees C by TSMR and SPR to be 5.7 or 5.9 kJ/mol, respectively, agreeing well with that determined by cGC, i.e., 5.7 kJ/mol at 30 degrees C.

show abstract

“…The very high GC enantioseparation factors α for "compound B" on modified CDs have been found by mere chance as the target (Fig. 25, left) [130]. Since volatile anesthetics are recycled during anesthesia in re-breathing units, the exhaled carbon dioxide is trapped with soda lime.…”

Section: An Extraordinary Enantiomeric Differentiationmentioning

confidence: 96%

Salient Features of Enantioselective Gas Chromatography: The Enantiomeric Differentiation of Chiral Inhalation Anesthetics as a Representative Methodological Case in Point

Schurig

2013

Topics in Current Chemistry

View full text Add to dashboard Cite

The enantiomeric differentiation of the volatile chiral inhalation anesthetics enflurane, isoflurane, and desflurane by analytical and preparative gas chromatography on various modified cyclodextrins is described. Very large enantioseparation factors α are obtained on the chiral selector octakis(3-O-butanoyl-2,6-di-O-pentyl)-γ-cyclodextrin (Lipodex E). The gas-chromatographically observed enantioselectivities are corroborated by NMR-spectroscopy using Lipodex E as chiral solvating agent and by various sensor devices using Lipodex E as sensitive chiral coating layer. The assignment of the absolute configuration of desflurane is clarified. Methods are described for the determination of the enantiomeric distribution of chiral inhalation anesthetics during narcosis in clinical trials. The quantitation of enantiomers in a sample by the method of enantiomeric labeling is outlined. Reliable thermodynamic parameters of enantioselectivity are determined by using the retention-increment R' approach for the enantiomeric differentiation of various chiral halocarbon selectands on diluted cyclodextrin selectors.

show abstract

Detailed investigation of fluoromethyl 1,1,1,3,3,3-hexafluoro-2-propyl ether (sevoflurane) and its degradation products. Part I: Synthesis of fluorinated, soda lime induced degradation products

Cited by 23 publications

References 10 publications

Dry soda lime markedly degrades sevoflurane during simulated inhalation induction

Dry soda lime markedly degrades sevoflurane during simulated inhalation induction

Use of a Modified Cyclodextrin Host for the Enantioselective Detection of a Halogenated Diether as Chiral Guest via Optical and Electrical Transducers

Salient Features of Enantioselective Gas Chromatography: The Enantiomeric Differentiation of Chiral Inhalation Anesthetics as a Representative Methodological Case in Point

Contact Info

Product

Resources

About