Abstract
Polyfunctional compounds were prepared by alkylation, acylation, and nitration of hydroxyl and amine functions of the following alkanolamine ether structures: (di)alkylamino alkyloxy propanol, hydroxy alkyloxy (di)alkylamino propanol, and their dimer compounds. The resulting compounds were characterized by conventional spectroscopic methods, and complete nuclear magnetic resonance data are given. These reactions extented the application of these propanic compounds to use as multipurpose fuel additives. In particular, they enhance phase stability and improve the cetane number in ethanol-diesel fuel blends.
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Macchia, B., A. Balsamo, A. Lapucci, F. Macchia, A. Martinelli, H.L. Ammon, S.M. Prasad, M.C. Breschi, M. Ducci, and E. Martinotti, Role of the (Acyloxy) Methyl Moiety in Eliciting the Adrenergic β-blocking Activity of 3-(Acyloxy) propanolamines, J. Med. Chem. 30(4):616–622 (1987).
Mauléon, D., M. Dolors-Pujol, and G. Rosell, β-Andrenergic Antagonists: N-alkyl and N-amidoethyl (arylalkoxy)propanolamines Related to Propanolol, Eur. J. Med. Chem. 23:421–426 (1988).
Manoury, P.M., J.L. Binet, J. Rousseau, F.M. Lefevre-Borg, and I.G. Cavero, Synthesis of a Series of Compounds Related to Betaxolol, A New β1-Adrenoceptor Antagonist with a Pharmacological and Pharmacokinetic Profile Optimized for the Treatment of Chronic Cardiovascular Diseases, J. Med. Chem. 30:1003–1011 (1987).
Guivisdalsky, P.N., and R. Bittman, Glycidyl Derivatives, J. Org. Chem. 54:4637–4642 (1989).
Satgé de Caro, P., Z. Mouloungui, and A. Gaset, Synthesis of Alkyloxy (di)Alkylamino Propanols, Hydroxy Alkylamino Propanols and the Dimer Compounds for Use as Fuel Additives, J. Am. Oil Chem. Soc. 74:235–240 (1997).
Davilov, A.M., Improvement of the Ecological Characteristics of Fuels by Using Additives, Chem. Technol. Fuels Oils, translated from Khimiya Tekhnologiya Topliv i Masel 6:31–33 (1990).
Gasoline and Diesel Fuel Additives, Critical Reports on Applied Chemistry, Vol. 25, edited by K. Owen, John Wiley & Sons, New York, 1990.
Satgé de Caro, P., Synthesis of Polyfunctional Oxygenated Additives for Ethanol-Diesel Fuel Blends, Thèse INP Toulouse No. 1001, Chap IV: Direct Injection Engine Tests, March 1995.
Berge, J. Ch., and J. Andrzejewski, Comparative Tests of Ethanol-Diesel Blends with Additives, Providing an Indirect Injection Engine, Laboratoire de Mécanique et d’Energétique de l’ESEM (Université d’Orléans) in collaboration with the G.I.E. de Recherche et d’Etudes PSA — Renault; Report of March 1996.
Recueil des Normes Françaises AFNOR Produits pétroliers (Oil products) — Combustibles liquides (Liquid fuels), Association Française pour la Normalisation, Paris, Tome 1, 1988, pp. 351–361, pp. 427–443.
Pretsch, Clerc, Seibl, Simmons, Tables of Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag, New York, 1985.
Greenhill, J.V., A Series of Amino-Alcohols Related to Benzhexol (1-Cyclohexyl-1-Phenyl-3-Piperidinopropan-1-ol), J. Chem. Soc. C9:1298 (1970).
Mamedov, S., and F.A. Sharifora, Ethers of Glycols and Their Derivatives: Synthesis of Alkoxymethyl Ethers from 1,3-Dialkoxy-2-Propanol, Otd. Obshch. Tekh. Khim.:29–33 (1967).
Trostmann, U., C. Schächtele, and K. Mannhardt, DE Patent No. 3625738 A1 (1988).
Olah, G.A., and C. Narang, Synthetic Methods and Reactions: Convenient and Safe Preparation of Alkyl Nitrates (Polynitrates) via Transfer Nitration of Alcohols (Polyols) with N-Nitrocollidinium Tetrafluoroborate, Synthesis: 452–453 (1978).
Cupas, C.A., and R.L. Pearson, Transfer Nitration via N-Nitropyridinium Salts, J. Am. Chem. Soc. 90:4742 (1968).
Emmons, W.D., and J.P. Freeman, Alkaline Nitration: The Nitration of Amines with Cyanohydrin Nitrates, Ibid.:4387–4390 (1955).
Bottaro, J.C., R.J. Schmitt, and C.D. Bedford, Nonacidic Nitration of Secondary Amines, J. Org. Chem. 52:2292–2294 (1987).
Chute, W.J., G.E. Dunn, and J.C. MacKenzie, Catalyzed Nitration of Amine; III Ease of Nitration Among Aliphatic Secondary Amines, Can. J. Res. 26B:114–137 (1948).
Chute, W.J., K.G. Herring, L.E. Thoombs, and G.F. Wright. Catalyzed Nitration of Amines: I Dinitroxydiethylnitramine, Ibid.:89–103 (1948).
Mouloungui, Z., and P. Satgé de Caro, French Patents (Renault) FR 95-02186 and FR 95-02187 (1995).
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de Caro, P.S., Mouloungui, Z. & Gaset, A. Synthesis of derivatives of alkylamino alkyloxy propanol structures by N-alkylation, acylation, and nitration. Application as fuel additives. J Amer Oil Chem Soc 74, 241–247 (1997). https://doi.org/10.1007/s11746-997-0130-0
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DOI: https://doi.org/10.1007/s11746-997-0130-0