Sage Journals: Discover world-class research

Abstract

Previous investigations reported the formation of a neurotoxicant, tri methylolpropane phosphate (TMP-P) during pyrolysis of synthetic, aircraft engine lubricating oils. Employing both sealed-tube and open-to-air methods of pyrolysis, we confirmed the formation of TMP-P during lubricant pyrolysis. Rodent bioassay and GC/MS analysis were performed for detection and quanti tation of neurotoxicant production. Maximal production of TMP-P for sealed- tube pyrolysis occured after 20 min at 500°C. A comparable amount of TMP-P was formed after 5 min at 650°C in open-to-air pyrolysis of lubricants. Our examination of TMP-P production was limited to L-23699 lubricants composed primarily of a trimethylolpropane (TMP) ester base stock. The formation of TMP-P was only dependent upon the presence of an organic phosphorous addi tive and TMP. Pyrolysed lubricants composed of a pentaerythritol base did not cause neurotoxicity in mice or rats following intraperitoneal (i.p.) injection. Other toxic bicyclophosphorous ester homologues were not detected in any pyrolyzed lubricants following GC/MS analysis. L-23699 lubricants which had been operationally employed in aircraft engines under rigorous test conditions, produced no neurotoxicity when intraperitoneally administered to rats.

Get full access to this article

View all access options for this article.

References

Petajan, J.H. , K.J. Vorhees , S.C. Packham , R.C. Baldwin , I.N. Einhorn , M.L. Grunnet , G.B. Dinger and M.M. Birky.

"Extreme Toxicity from Combustion Products of a Fire-Retarded Polyurethane Foam,"

Science , 187:742-744 (1975).

Grunnet, M.L.

"Ultrastructural Changes Produced by the Bicyclophosphate Ester,"

J. Neuropathol. Exper. Neurol. , 34:351 (1976).

Voorhees, K.J. , I.N. Einhorn , F.D. Hileman and L.H. Wojcik.

"The Identification of a Highly Toxic Bicyclophosphate in the Combustion Products of a Fire-Retarded Urethane Foam,"

Polymer Lett., 13:293-297 (1975).

Kalman, D.A. , K.J. Voorhees , D. Osborne and I.N. Einhorn.

"Production of a Bicyclophosphate Neurotoxic Agent During Pyrolysis of Synthetic Lubricant Oil,"

J. Fire Sci., 3:322-329 (1985).

Bellet, E.M. and J.E. Casida.

"Bicyclic Phosphorous Esters: High Toxicity Without Cholinesterase Inhibition,"

Science , 182:1135-1136 (1973).

Casida, J.E. , M. Eto , A.D. Moscioni , J.L. Engel , D.W. Milbrath and J.G. Verkade.

"Structure-Toxicity Relationships of 2, 6, 7-Trioxabicyclo [2.2.2] Octanes and Related Compounds,"

Toxicol. Appl. Pharmacol., 36:261-279 (1976).

Kimmerle, G. , A. Eben , P. Groning and J. Thyssen.

"Acute Toxicity of Bicyclic Phosphorous Esters,"

Arch. Toxicol., 35:149-152 (1976).

Eto, M. , Y. Ozoe , T. Fujita and J.E. Casida.

"Significance of Branched Bridge-Head Substitutent in Toxicity of Bicyclic Phosphate Esters,"

Agr. Biol. Chem., 40:2113-2115 (1976).

Milbrath, D.S. , J.L. Engel , J.G. Verkade and J.E. Casida.

"Structure-Toxicity Relationships of 1-Substituted-4-Alkyl-2, 6, 7-Trioxabicyclo [2.2.2] Octanes,"

Toxicol. Appl. Pharmacol., 47:287-293 (1973).

10.

Bowery, N.G. , J.F. Collins , R.G. Hill and S. Pearson.

"GABA Antagonism as a Possible Basis for the Convulsant Action of a Series of Bicyclic Phosphorous Esters,"

Br. J. Pharmaco., 57:435-436 (1976).

11.

Bowery, N.G. , J.F. Collins , R.G. Hill and S. Pearson.

"t-Butyl Bicyclophosphate : A Convulsant and GABA Antagonist More Potent Than Bicuculline,"

Br. J. Pharmacol., 60:275-276 (1977).

12.

Matsson, H.

"Bicyclic Phosphates Increase the Cyclic GMP Level in Rat Cerebellum, Presumably Due to Reduced GABA Inhibition,"

Brain Research, 181:175-184 (1980).

13.

Simmonds, M.A.

"Classification of Some GABA Antagonists With Regard to Site of Action and Potency in Slices of Rat Cuneate Nucleus,"

Eur. J. Pharmacol., 18:347-358 (1982).

14.

Ticku, M.K. and R. Ramanjaneyulu.

"Differential Interactions of GABA Agonists, Depressant and Convulsant Drugs with [35S]-t-Butylbicyclophorothionate Binding Sites in Cortex and Cerebellum,"

Pharmacol. Biochem. Behav., 21:151-158 (1984).

15.

Seifert, J. and J.E. Casida.

"Solubilization and Detergent Effects on Interactions of Some Drugs and Insecticides with the t-Butylbicyclophosphoronthionate Binding Site Within the ?-Aminobutyric Acid Receptor-Ionophore Complex,"

J. Neurochem., 44:110-116 (1985).

16.

Verkade, J.G. and L.T. Reynolds.

"The Synthesis of a Novel Ester of Phosphorous and Arsenic,"

J Org. Chem. , 25:663-664 (1960).

17.

Wadsworth, W.S., Jr. and W.D. Emmons.

"Bicyclic Phosphites,"

J. Amer. Chem. Soc., 84:610-617 (1962).

18.

Kenttamaa, H. and J. Enquist.

"Electron Impact Induced Fragmentation of 4-Alkyl Derivatives of 2, 6, 7-Trioxa-1-Phosphabicyclo [2.2.2] Octane and the Corresponding 1-Oxides, 1-Sulfides, and 1-Selenides,"

Org. Mass. Spect., 15:520-525 (1980).

19.

Mathias, A. "Trimethylolpropane Phosphate (TMP-P)," Obtained from: Research Department, Organics Division, Imperial Chemical Industries Limited (1975).

20.

"Depot Maintenance Work Requirement for Engine Assembly, Models T63-A-54 and T63-A-700," USAAVSCOM DMWR-55-2840-231, U.S. Army Aviation Systems Command, St. Louis, MO.

High Temperature Decomposition of Military Specification L-23699 Synthetic Aircraft Lubricants

Abstract

Get full access to this article

References