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Pure Appl. Chem., 1986, Vol. 58, No. 6, pp. 857-868

http://dx.doi.org/10.1351/pac198658060857

Industrial applications of phase transfer catalysis (PTC): past, present and future

H. H. Freedman

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  • Purohit Meena K., Chakka Sai Kumar, Scovell Iain, Neschadim Anton, Bello Angelica M., Salum Noruê, Katsman Yulia, Bareau Madeleine C., Branch Donald R., Kotra Lakshmi P.: Structure–activity relationships of pyrazole derivatives as potential therapeutics for immune thrombocytopenias. Bioorganic & Medicinal Chemistry 2014. <http://dx.doi.org/10.1016/j.bmc.2014.03.016>
  • Sutter Marc, Dayoub Wissam, Métay Estelle, Raoul Yann, Lemaire Marc: 1,2,3-Trimethoxypropane and Glycerol Ethers as Bio-Sourced Solvents from Glycerol. Synthesis by Solvent-Free Phase-Transfer Catalysis and Utilization as an Alternative Solvent in Chemical Transformations. ChemCatChem 2013, 5, 2893. <http://dx.doi.org/10.1002/cctc.201300458>
  • Loganathan Subramanian, Rajendran Venugopal: Ultrasound assisted polymerization of N-vinyl imidazole under phase-transfer catalysis condition – A kinetic study. Ultrasonics Sonochemistry 2013, 20, 308. <http://dx.doi.org/10.1016/j.ultsonch.2012.07.004>
  • Kikkawa Nobuaki, Ishiyama Tatsuya, Morita Akihiro: Molecular dynamics study of phase transfer catalyst for ion transfer through water���chloroform interface. Chemical Physics Letters 2012. <http://dx.doi.org/10.1016/j.cplett.2012.03.027>
  • Vilar Márcio, Navarro Marcelo: β-cyclodextrin as inverse phase transfer catalyst on the electrocatalytic hydrogenation of organic compounds in water. Elctrochim Acta 2012, 59, 270. <http://dx.doi.org/10.1016/j.electacta.2011.10.094>
  • Naeimi Hossein, Rabiei Khadijeh: Sonocatalyzed facile and mild one pot synthesis of gem-dichloroaziridine derivatives under alkaline conditions. Ultrasonics Sonochem 2012, 19, 130. <http://dx.doi.org/10.1016/j.ultsonch.2011.06.012>
  • Wang Maw-Ling, Prasad Gandavaram Syam: Phase-transfer catalytic dichlorocyclopropanation of styrene under the influence of ultrasound conditions ��� A kinetic study. Ultrasonics Sonochemistry 2012. <http://dx.doi.org/10.1016/j.ultsonch.2012.02.010>
  • Wu Xiongyu, Öhrngren Per, Joshi Advait A., Trejos Alejandro, Persson Magnus, Arvela Riina K., Wallberg Hans, Vrang Lotta, Rosenquist Åsa, Samuelsson Bertil B.: Synthesis, X-ray Analysis, and Biological Evaluation of a New Class of Stereopure Lactam-Based HIV-1 Protease Inhibitors. J Med Chem 2012, 55, 2724. <http://dx.doi.org/10.1021/jm201620t>
  • Borovinskaya E. S., Reschetilowski W.: Perspectives of heterogeneous process intensification in microreactors. Russ J Gen Chem 2012, 82, 2108. <http://dx.doi.org/10.1134/S1070363212120316>
  • Gao Baojiao, Wang Lin, Du Ruikui, Li Yanbin: Synthesis of N-butylphthalimide catalyzed by quaternary phosphonium salt-type triphase catalysts based on cross-linked polystyrene microspheres. Inter J Chem Kinet 2011, 43, 677. <http://dx.doi.org/10.1002/kin.20579>
  • Wang Maw-Ling, Hsieh Yu-Ming, Chang Chih-Wu: A KINETIC STUDY OF PHASE TRANSFER CATALYZED BENZYLATION OF 2,4,6-TRIBROMOPHENOL IN LIQUID-LIQUID TWO-PHASE SOLUTION. Chem Eng Commun 2011, 198, 939. <http://dx.doi.org/10.1080/00986445.2011.545297>
  • Borovinskaya E. S., Reshetilovskii V. P.: Microreactors as the new way of intensification of heterogeneous processes. Russ J Appl Chem 2011, 84, 1094. <http://dx.doi.org/10.1134/S107042721106036X>
  • Naeimi Hossein, Rabiei Khadijeh: Ultrasonic-Assisted Synthesis of 1,3-Diaryl-2,2-dichloroaziridine Derivatives in the Presence of Phase-Transfer Catalyst under Low-Concentration Alkaline Conditions. J Chem Soc Japan 2011, 84, 1112. <http://dx.doi.org/10.1246/bcsj.20110106>
  • Kanjilal Pranab R., Malpani Yashwardhan, Rajan Ramya, Badgujar Sachin, Kaur Kamaljit: Practical and Chemoselective Reduction of Acyl Chloride to Alcohol by Borohydride in Aqueous Dichloromethane. Synth Comm 2010, 40, 2897. <http://dx.doi.org/10.1080/00397910903340645>
  • Wang Maw‐Ling, Liu Yen‐Chun, Lin Shan‐Je: Kinetic study of synthesizing (4‐methyl) methyl benzoatyltriphenyl phosphonium bromide in a two‐phase reaction. J Chin Inst Eng 2010, 33, 781. <http://dx.doi.org/10.1080/02533839.2010.9671668>
  • Wang Maw-Ling, Hsieh Yu-Ming: Kinetic Study of Synthesising 2,4,6-tribromophenyl Benzyl Ether by Phase Transfer Catalysis. Dev Chem Eng Mineral Process 2008, 1, 225. <http://dx.doi.org/10.1002/apj.5500010404>
  • Wang M.-L., Chang S.-W.: Kinetics of Synthesizing Dibutanoxymethane at Very High Alkaline Concentration by Phase Transfer Catalysis. Dev Chem Eng Mineral Process 2008, 2, 124. <http://dx.doi.org/10.1002/apj.5500020205>
  • Wang Maw-Ling, Chen Wei-Hung, Ming-Hsiung: Synthesis of dialkoxydiphenylmethane under phase transfer catalytic condition assisted by ultrasonic irradiation. React Kinet Catal Lett 2008, 95, 47. <http://dx.doi.org/10.1007/s11144-008-5279-5>
  • Rajendran Venugopal, Wang Maw-Ling: Dichlorocarbene addition to allyl phenyl ether under phase-transfer catalysis conditions—A kinetic study. Journal of Molecular Catalysis A 2008, 288, 23. <http://dx.doi.org/10.1016/j.molcata.2008.03.015>
  • Murugan Eagambaram, Gopinath Prakash: Catalytic activity of novel soluble multi-site phase transfer catalyst in dichlorocarbene addition to α-pinene. Journal of Molecular Catalysis A 2008, 294, 68. <http://dx.doi.org/10.1016/j.molcata.2008.08.004>
  • Wang Maw-Ling, Liu Biing-Lang, Lin Shan-Je: TWO-PHASE WITTIG REACTION OF SYNTHESIZING LIQUID CRYSTAL INTERMEDIATE BY ACTIVE QUATERNARY PHOSPHONIUM SALT. Chem Eng Commun 2008, 195, 770. <http://dx.doi.org/10.1080/00986440701690956>
  • Liu Yen-Chun, Wang Maw-Ling: KINETIC STUDY OF S-ALKYLATION OF 2-MERCAPTOBENZIMIDAZOLE CATALYZED BY TETRABUTYLAMMONIUM BROMIDE. Chem Eng Commun 2008, 196, 530. <http://dx.doi.org/10.1080/00986440802484515>
  • Wang Maw-Ling, Chen Chau-Je, Wang Feng-Sheng: KINETIC STUDY OF SYNTHESIZING 1-PHENYl-3-PROPYL ETHER UNDER LIQUID-LIQUID PHASE-TRANSFER CATALYTIC CONDITIONS. Chem Eng Commun 2008, 196, 573. <http://dx.doi.org/10.1080/00986440802484564>
  • Svobodová Eva, Cibulka Radek, Hampl František, Jurok Radek: Reactivity in Micelles - Are We Really Able to Design Micellar Catalysts?. Collect Czech Chem Commun 2008, 73, 127. <http://dx.doi.org/10.1135/cccc20080127>
  • Wang Maw-Ling, Rajendran Venugopal: Kinetics for dichlorocyclopropanation of 1,7-octadiene under the influence of ultrasound assisted phase-transfer catalysis conditions. Journal of Molecular Catalysis A 2007, 273, 5. <http://dx.doi.org/10.1016/j.molcata.2007.03.056>
  • Hamamoto Hiromi, Suzuki Yachiyo, Takahashi Hideyo, Ikegami Shiro: Direct transformation of benzilic amines to carbonyls using polyacrylamide-bound tungstate under phase-transfer catalysis conditions. Tetrahetron Lett 2007, 48, 4239. <http://dx.doi.org/10.1016/j.tetlet.2007.04.071>
  • Wang Maw-Ling, Huang Tsun-Hsuan: KINETIC STUDY OF BENZYL ALCOHOL OXIDATION UNDER PHASE TRANSFER CATALYSIS CONDITIONS. Chem Eng Commun 2007, 194, 618. <http://dx.doi.org/10.1080/00986440600992685>
  • Khalil Ali Kh.: Phase-Transfer Catalyzed Alkylation and Acylation of 2-Mercapto-5-Methyl-1H-Benzimidazole. Phosphorus Sulfur Silicon Relat Elem 2007, 182, 815. <http://dx.doi.org/10.1080/10426500601059433>
  • Koldobskii G. I.: Phase-transfer catalysis in the chemistry of heterocyclic compounds. Kinet Catal 2007, 48, 505. <http://dx.doi.org/10.1134/S0023158407040064>
  • Sharma Pratibha, Kumar Ashok, Sharma Manisha: Generation of 4,6-dimethyl-5-[2-(2-methylprop-1-enyl)-1H-benzimidazol-1-yl]pyrimidine-2(5H)-thiones under kinetically controlled phase transfer catalysis conditions. Journal of Molecular Catalysis A 2005, 237, 191. <http://dx.doi.org/10.1016/j.molcata.2005.05.003>
  • WANG MAW-LING, TSENG YAO-HSUAN: Analysis of Phase-Transfer-Catalyzed O-Alkylation Reaction Using Fractional Factorial Design Method. Chem Eng Com 2005, 192, 557. <http://dx.doi.org/10.1080/00986440590495052>
  • El-Sayed A. M., Khalil A. Kh., Hassan M. A., Mohamed M. M.: Phase-Transfer Catalyzed Alkylation and Cycloalkylation of 3-Substituted-1H-pyrazol-2-in-5-ones in the Absence or Presence of Carbon Disulphide. Phosphorus Sulfur Silicon Relat Elem 2005, 180, 479. <http://dx.doi.org/10.1080/104265090517208>
  • Mahdavi H., Tamami B.: Synthesis of β -Dihydroxysulfides by Cleavage of Epoxides Using Quaternized Amino-Functionalized Cross-Linked Polyacrylamide as a New Polymeric Phase Transfer Catalyst. Phosphorus Sulfur Silicon Relat Elem 2005, 180, 1929. <http://dx.doi.org/10.1080/104265090902651>
  • Khalil A. Kh.: Phase-Transfer Catalyzed Alkylation and Cycloalkylation of 2-Mercaptoquinazolin-4(3H)-One. Phosphorus Sulfur Silicon Relat Elem 2005, 180, 2533. <http://dx.doi.org/10.1080/104265090929940>
  • Tang Ruiren, Gou Cancheng: The Synthesis and Evalution of Novel Aryl-Substituted Dithioimidophosphonates as an Extrantant for Metals. Phosphorus Sulfur Silicon Relat Elem 2005, 180, 2725. <http://dx.doi.org/10.1080/104265090968064>
  • Wang Maw-Ling, Hsieh Yu-Ming: Kinetic study of dichlorocyclopropanation of 4-vinyl-1-cyclohexene by a novel multisite phase transfer catalyst. Journal of Molecular Catalysis A 2004, 210, 59. <http://dx.doi.org/10.1016/j.molcata.2003.09.025>
  • Wang Maw-Ling, Hsieh Yu-Ming, Chang Rong-Yeu: Kinetic study of dichlorocyclopropanation of 1,7-octadiene under two-phase phase-transfer catalysis at low alkaline concentration. Journal of Molecular Catalysis A 2003, 198, 111. <http://dx.doi.org/10.1016/S1381-1169(03)00005-0>
  • Wang Maw-Ling, Tseng Yao-Hsuan: Phase transfer catalytic reaction of n-bromobutane and sodium sulfide in a two-phase solution and its kinetics. Journal of Molecular Catalysis A 2003, 203, 79. <http://dx.doi.org/10.1016/S1381-1169(03)00374-1>
  • Jwo Jing-Jer: Phase Transfer Catalysis: Fundamentals and Selected Systems. Catal Rev —Sci Eng 2003, 45, 397. <http://dx.doi.org/10.1081/CR-120025539>
  • Wang Maw-Ling, Huang Tsuan-Hsuan: Epoxidation of Dicyclopentadiene under Phase Transfer Catalysis Conditions: Pseudo Steady State Hypothesis Approach. J Chem Eng Japan / JCEJ 2003, 36, 231. <http://dx.doi.org/10.1252/jcej.36.231>
  • Wang Maw-Ling, Tseng Yao-Hsuan: Phase-transfer catalytic reaction of dibromo-o-xylene and 1-butanol in two-phase solution. Journal of Molecular Catalysis A 2002, 179, 17. <http://dx.doi.org/10.1016/S1381-1169(01)00322-3>
  • Wang Maw-Ling, Tseng Yao-Hsuan: Kinetic model for synthesizing 4,4′-diethanoxy biphenyl by phase transfer catalysis. Journal of Molecular Catalysis A 2002, 188, 51. <http://dx.doi.org/10.1016/S1381-1169(02)00065-1>
  • Samant Ketan D., Singh Divya J., Ng Ka M.: Design of liquid-liquid phase transfer catalytic processes. AIChE 2001, 47, 1832. <http://dx.doi.org/10.1002/aic.690470814>
  • Hsiao Hsu-Chin, Weng Hung-Shan: Synthesis ofn-butyl phenyl ether by tri-liquid-phase catalysis using poly(ethylene glycol)-600 as a catalyst - analysis of factors affecting the reaction in a batch reactor. J Chem Technol Biotechnol 2001, 76, 959. <http://dx.doi.org/10.1002/jctb.470>
  • Armor J.N: Overcoming equilibrium limitations in chemical processes. CATAL A GENERAL 2001, 222, 91. <http://dx.doi.org/10.1016/S0926-860X(01)00833-X>
  • Lu Yen Liang, Jwo Jing-Jer: Inverse phase transfer catalysis: kinetics of the pyridine-1-oxide-catalyzed two-phase reactions of methyl-, methoxy-, iodo-, and nitro-benzoyl chlorides and benzoate ions. Journal of Molecular Catalysis A 2001, 170, 57. <http://dx.doi.org/10.1016/S1381-1169(01)00076-0>
  • Desikan Sridhar, Doraiswamy L.K: Enhanced activity of polymer-supported phase transfer catalysts. Chem Eng Set 2000, 55, 6119. <http://dx.doi.org/10.1016/S0009-2509(00)00221-9>
  • Chang Yung Sheng, Jwo Jing-Jer: Inverse phase transfer catalysis. Kinetics of the pyridine 1-oxide-catalyzed reactions of dichlorobenzoyl chlorides and benzoate ions. Journal of Molecular Catalysis A 2000, 160, 357. <http://dx.doi.org/10.1016/S1381-1169(00)00277-6>
  • Hung Shu-Mei, Jwo Jing-Jer: Inverse phase transfer catalysis: kinetics of the pyridine 1-oxide-catalyzed two-phase reactions of fluoro- and butyl-benzoyl chlorides and benzoate ions. Journal of Molecular Catalysis A 2000, 154, 55. <http://dx.doi.org/10.1016/S1381-1169(99)00377-5>
  • WANG MAW-LING, OU CHIN-CHOU, JWO JING-JER: STUDY OF THE REACTION OF GLYCINE AND BENZOYL CHLORIDE UNDER INVERSE PHASE TRANSFER CATALYSIS. Chem Eng Com 2000, 179, 233. <http://dx.doi.org/10.1080/00986440008912198>
  • Wang Maw‐Ling, Ou Chin‐Chou, Jwo Jing‐Jer: Kinetics of the reaction of benzoyl chloride and β‐methylalanine under inverse phase transfer catalysis. J Chin Inst Eng 2000, 23, 171. <http://dx.doi.org/10.1080/02533839.2000.9670535>
  • Wang Maw-Ling, Hsu Shun-Li: Phase-transfer catalytic reaction of 2,4,6-tribromophenol and dibromomethane: effect of potassium hydroxide. Journal of Molecular Catalysis A 1999, 150, 11. <http://dx.doi.org/10.1016/S1381-1169(99)00214-9>
  • MAO JINGCHENG, HU JIYE, SHANG SHUCHUAN, LIU HONGJING, HU LITIAN: 13G NMR and ESR studies on the association between sodium 3-dodecy I ether-2-hydroxypropy1-1-sulfonate and polyvinylpyrrolidone. JOURNAL OF DISPERSION SCIENCE ANDTECHNOLOGY 1999, 20, 1345. <http://dx.doi.org/10.1080/01932699908943857>
  • Naik Sanjeev D., Doraiswamy L. K.: Phase transfer catalysis: Chemistry and engineering. AIChE 1998, 44, 612. <http://dx.doi.org/10.1002/aic.690440312>
  • WANGast; MAW-LING, OU CHIN-CHOU, JWO JING-JER: EFFECT OF THE DISTRIBUTION OF PYRIDINE 1-OXIDE ON ITS CATALYZED TWO-PHASE REACTION OF BENZOYL CHLORIDE AND CARBOXYLATE ION. Chem Eng Com 1998, 165, 151. <http://dx.doi.org/10.1080/00986449808912373>
  • Liu Biing‐Lang, Wang Maw‐Ling: Reaction of carbon disulfide and o‐phenylene diamine catalyzed by quaternary ammonium salt in the presence of potassium hydroxide. J Chin Inst Eng 1998, 21, 171. <http://dx.doi.org/10.1080/02533839.1998.9670382>
  • Liu Biing‐Lang, Wang Maw‐Ling: Reaction of carbon disulfide and o‐phenylene diamine by tertiary amine in the presence of potassium hydroxide. J Chin Inst Eng 1998, 21, 317. <http://dx.doi.org/10.1080/02533839.1998.9670395>
  • Naik Sanjeev D., Doraiswamy L.K.: Mathematical modeling of solid-liquid phase-transfer catalysis. Chem Eng Set 1997, 52, 4533. <http://dx.doi.org/10.1016/S0009-2509(97)00297-2>
  • Wang Maw-Ling, Liu Biing-Lang: Catalyzed reaction of carbon disulfide and o-phenylene diamine by tertiary amine. Journal of Molecular Catalysis A 1996, 105, 49. <http://dx.doi.org/10.1016/1381-1169(95)00183-2>
  • Ou Jang-Shiann, Chen Rong-Huey, Jwo Jing-Jer: Inverse phase transfer catalysis. Kinetics of the pyridine 1-oxide-catalyzed reaction of chlorobenzoyl chloride and chlorobenzoate ion. Journal of Molecular Catalysis A 1996, 110, 95. <http://dx.doi.org/10.1016/1381-1169(96)00059-3>
  • Koldobskii G. I.: Phase transfer catalysis in the chemistry of five-membered nitrogen-containing heterocycles. Russ Chem Bull 1995, 44, 2019. <http://dx.doi.org/10.1007/BF00696700>
  • Wang Maw-Ling, Ou Chin-Chou, Jwo Jing-Jer: Kinetics of the reaction of benzoyl chloride and sodium carboxylate under inverse phase-transfer catalysis. Journal of Molecular Catalysis A 1995, 99, 153. <http://dx.doi.org/10.1016/1381-1169(95)00006-2>
  • Wang Maw‐Ling, Chang Shahng‐Wern: A kinetic study of synthesizing acetal compounds by phase transfer catalytic reaction. J Chin Inst Eng 1995, 18, 69. <http://dx.doi.org/10.1080/02533839.1995.9677667>
  • Wang Maw‐Ling, Hsieh Yu‐Ming: A simplified kinetic model for the alkylation of 2,4,6‐tribromophenol by phase transfer catalysis. J Chin Inst Eng 1995, 18, 615. <http://dx.doi.org/10.1080/02533839.1995.9677727>
  • Wang Maw-Ling, Ou Chin-Chou, Jwo Jing-Jer: Study of the Reaction of Benzoyl Chloride and Sodium Dicarboxylate under Inverse Phase Transfer Catalysis. Bull Chem Soc Jpn 1995, 68, 2165. <http://dx.doi.org/10.1246/bcsj.68.2165>
  • WANG MAW-LING, CHANG SHAHNG-WERN: A SIMPLIFIED KINETIC MODEL FOR SYNTHESIZING DIALKOXYMETHANE BY PHASE TRANSFER CATALYSIS. Chem Eng Com 1994, 127, 191. <http://dx.doi.org/10.1080/00986449408936232>
  • Wang Maw-Ling, Ou Chin-Chou, Jwo Jing-Jer: Study of the Pyridine 1-Oxide-Catalyzed Two-Phase Reversible Exchange Reaction of Benzoyl Chloride and Butanoate Ion. Bull Chem Soc Jpn 1994, 67, 2949. <http://dx.doi.org/10.1246/bcsj.67.2949>
  • Wang Maw-Ling, Chang Shahng-Wern: Mechanism and kinetics of synthesizing dibutoxymethane by phase transfer catalysis. React Kinet Catal Lett 1993, 49, 333. <http://dx.doi.org/10.1007/BF02067700>
  • Wang Maw‐Ling, Chang Kong‐Rong: Effects of solvents and molecular weights of polyethylene glycols on the allylation of phenoxide. J Chin Inst Eng 1993, 16, 675. <http://dx.doi.org/10.1080/02533839.1993.9677541>
  • Wang Maw-Ling, Hsieh Yu-Ming: Dynamics of the Reaction of 2,4,6-tribromophenol and Benzyl Bromide by Phase Transfer Catalysis. J Chem Eng Japan / JCEJ 1993, 26, 374. <http://dx.doi.org/10.1252/jcej.26.374>
  • Wang Maw-Ling, Chang Kong-Rong: Kinetics of the allylation of phenoxide by polyethylene glycol in a two-phase reaction. Can J Chem Eng 1991, 69, 340. <http://dx.doi.org/10.1002/cjce.5450690141>
  • Wang Maw-Ling, Yang Hung-Ming: Dynamics of phase transfer catalyzed reaction for the allylation of 2,4,6-tribromophenol. Chem Eng Set 1991, 46, 619. <http://dx.doi.org/10.1016/0009-2509(91)80021-P>
  • Armor John N.: Conventions and cartels. Applied Catalysis 1991, 78, N17. <http://dx.doi.org/10.1016/0166-9834(91)80103-4>
  • Wang Maw-Ling, Chang Kong-Rong: The effects of polyethylene glycol on synthesizing phenyl allyl ether in a two-phase reaction. Journal of Molecular Catalysis 1991, 67, 147. <http://dx.doi.org/10.1016/0304-5102(91)85042-Z>
  • Wang Maw-Ling, Yang Hung-Ming, Chauvin Remi, Kiricsi I., Tasi G.Y., Hannus I., Fejes P., F��ster H.: Kinetic study of the synthesis of 4-bromophenyl allyl ether by phase transfer catalysis. Journal of Molecular Catalysis 1990, 62, 135. <http://dx.doi.org/10.1016/0304-5102(90)85208-Y>
  • Goldberg Yuri, Ābele Edgars, Bremanis Gunārs, Trapenciers Pēteris, Gaukhman Alexander, Popelis Juris, Gomtsyan Artur, Kalviņš Ivars, Shymanska Mariya, Lukevics Edmunds: Betaines derived from amino and hydrazino acids as phase transfer catalysts. Tetrahedron 1990, 46, 1911. <http://dx.doi.org/10.1016/S0040-4020(01)89759-3>
  • Urata K., Yano S., Kawamata A., Takaishi N., Inamoto Y.: A convenient synthesis of long-chain 1-O-Alkyl glyceryl ethers. J Amer Oil Chem Soc 1988, 65, 1299. <http://dx.doi.org/10.1007/BF02542409>
  • Sharma M.M.: Multiphase reactions in the manufacture of fine chemicals. Chem Eng Set 1988, 43, 1749. <http://dx.doi.org/10.1016/0009-2509(88)87039-8>
  • Wang Der-Her, Weng Hung-Shan: Preliminary study on the role played by the third liquid phase in phase transfer catalysis. Chem Eng Set 1988, 43, 2019. <http://dx.doi.org/10.1016/0009-2509(88)87078-7>