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THE FORMATION Off DIHAPHTHYL SUIPHQHIC ACIDS ATO THEIR DERIVATIVES

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THE FORMATION Off DIHAPHTHYL SUIPHQHIC ACIDS ATO THEIR DERIVATIVES THE FORMATION Off DIHAPHTHYL SUIPHQHIC ACIDS ATO THEIR DERIVATIVES. by Geoffrey D, Muir, B.Sc*, A.I.C. A thesis submitted in fulfilment of the requirements for the degree of Doctor of Philosophy in the Faculty of Science of Glasgow University, May, 1957 * ProQuest Number: 13905254 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a com plete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest ProQuest 13905254 Published by ProQuest LLC(2019). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States C ode Microform Edition © ProQuest LLC. ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48106- 1346 The author wishes to record his sincere thanks to Professor W. M. Cumming whose advice and encouraging supervision of this research have proved invaluable. He is also much indebted to the Royal Technical College for the facilities provided; to Uobel Industries for a bursary held during the session 1932-33; and to Imperial Chemical Industries for gifts of materials. THE FQBMATTOW m? DIHAPHTHIL gPLPEOHIO ACIDS -AMD THE IB DERIVATIVES. C0H1EHTS. Page. IHTRQDUCTQRY REVIEW. 1 (1) Preparation of Halogeno-naphthalene Sulphonic Acids, 6 (2) Application of the XJllmaon Reaction to Salts and Derivatives of Halogeno-naphthalene Sulphonic Acids. 10 (3) fhe Reaction of Diazonaphthalene Sulphonic Acids with 11 .Ammoniacal Cuprous Oxide Solution** • 16 (a) Reduction by means of Sulphur Dioxide. 17 (b) Reduction by means of Hydroxyl amine. 21 (4) Other Attempts to Effect Direct Diaryl-Pormation. 24 (5) Reaction of Diazo-Compounds with Sodium Sulphite. 26 Rotes. 27 EXPERIICBNTAh SECTION. 28 Starting Materials. 28 Diazotization Technique. 28 Arrangement of Results. 29 I. 1-Haphthylamine-4-Sulphonic Acid. (Haphthionic Acid). 30 (1) Preparation of Sodium l-Naphthylamine-4-Sulphonate. 30 (2) Diazotization of Haphthionic Acid. 30 (3) Properties of the Diazo-Compound. 32 (4) Preparation of Copper, Sodium and Potassium 1:4- Chloronaphthalene Sulphonates. 33 (5) Derivatives of 1:4-Chloronaphthalene Sulphonic Acid. (Sulphonyl chloride, sulphonamide, sulphoanilide, sulpho-o-toluidide, sulpho-p-nitroanilide and sulpho- a-naphthylamide.) 33 (6) Attempts to Prepare 1:11-Dinaphthyl-4:41-Disulphonic Acid from Salts and Derivatives of 1:4-Chloronaphth- alene Sulphonic Acid. 37 (7) Preparation of Potassium 1:4-Iodonaphthalene Sulph- onate. 38 (8) Derivatives of 1: 4-Ioaonaphthalene Sulphonic Acid. (Sulphonyl chloride, sulphonamide, sulphoanilide and sulpho-o-toluidide.) 40 CONTENTS. - continued. -----------------------------------------------------------------------------------------------------------------------------------Page (9) Derivates of Naphthalene-a-Sulphonic Acid. (Sulphonyl chloride, sulphonamide, sulphoanilide, sulpho-o-toluidide and sulpho-p-nitroanilide 42 (10) Attempts to Prepare 1 :1*-Dinaphthyl-4:4*-Disulphonic Acid from Salts and Derivatives of 1:4-Iodonaphth- alene Sulphonic Acid. 44 (a) Employing Potassium 1;4-Iodonaphthalene Sulphon- ate. 44 (b) Employing 1:4-Iodonaphthalene Sulphonamide. 45 (c) Employing 1:4-Iodonaphthalene Sulphoanilide. 46 (11) Reaction of 1:4-Diazonaphthalene Sulphonic Acid with an Ammoniacal Solution of Tetrammino-Cupric Sulphate Reduced by means of Sulphur Dioxide. 46 Note on "Salting Out". 49 (12) Reaction of 1:4-Diazonaphthalene Sulphonic Acid with Sodium Sulphite Solution. 50 (15) Reaction of 1:4-Diazonaphthalene Sulphonic Acid with an Ammoniacal Solution of letrammino-Cuprous Sulphate. 56 (14) Reaction of 1:4-Diazonaphthalene Sulphonic Acid with Sulphurous Acid in the Presence of Pyridine. 57 (15) Various Experiments without Conclusive Results. 58 (16) Attempts to Prepare Sulpho-Derivatives of haphthionic Acid. (Formation of phenyl-a-naphthylamine, aniline naphthionate, p-naphthylamine naphthionate, pp— dinaphthylamine and a-naphthylamine naphthionate.) 59 II. 1—Naphthylamine-2-Sulphonic Acid. (o-Naphthionic Acid). 64 (1) Sodium l-Naphthylamine-2—Sulphonate. 64 (2) Diazotization of o-Naphthionic Acid. 64 (5) Preparation of Sodium and Potassium 1: 2-Iodonaphth­ alene Sulphonates. 65 (4) Derivatives of 1: 2-Iodonaphthalene Sulphonic Acid. (Sulphonyl chloride and sulphonamide). 66 (5) Reaction of Sodium and Potassium 1:2-Iodonaphthalene Sulphonates in Aqueous Solution with Copper Powder. 66 j[6) Preparation of Sodium 1; 2-Bromonaphthalene Sulphonate.70 (7) Derivatives of Is 2-Bromonaphthalene Sulphonic Acid. (Sulphonyl chloride and sulphonamide.) 71 (8) Attempt to Prepare 1:1 *-Dinaphthyl-2: R^Disulphonic Acid from Sodium 1: 2-Bromonaphthalene Sulphonate. 72 CQR1ERTS. - continued. Page (9) Reaction of 1:2-Diazonaphthalene Sulphonic Acid with an .Ammoniacal Solution of fetrammino-Cupric Sulphate Reduced by means of Sulphur Dioxide. 75 (10) Reaction of Is 2-Diazonaphthalene Sulphonic Acid with an Ammoniacal Solution of f etrammino-Cuprous Sulphate.74 III. 1-Daphthyl amine-5-Sulphonic Acid. (Laurent Acid). 76 (1) Preparation of Sodium l:Naphthylamine-5-Sulphonate. 76 (2) Diazotization of Laurent Acid. 76 (5) Preparation of potassium 1: 5-Iodonaphthalene Sulph- onate. (Also sulphonyl chloride and sulphonamide). 77 (4) Reaction of Potassium 1: 5-Iodonaphthalene Sulphonate in Aqueous Solution with Copper Powder and Zinc Dust. 77 (5) Reaction of 1: 5-Diazonaphthalene Sulphonic Acid with an Ammoniacal Solution of Tetramrnino-cupric Sulphate Reduced by means of Sulphur Dioxide. 76 (6) Reaction of 1: 5-Diazonaphthalene Sulphonic Acid with an iimmoniacal Solution of letrammino-Cuprous Sulphate.79 (7) Two Reactions of 1:5-Diazonaphthalene Sulphonic Acid without Definite Results. 81 IV. l-Haphthylamine-7-Sul phonic Acid. (Cleve Acid). 85 (1) Purification of Cleve Acid. 85 (2) Diazotization of Cleve Acid. 85 (5) Preparation of Sodium l:7-Iodonaphthalene Sulphonate. 84 (4) Derivatives of 1:7—Iodonaphthalene Sulphonic Acid. 85 (Sulphonyl chloride and sulphonamide.) (5) Attempt to Prepare 1:11-Dinaphthyl-7:7‘-Disulphonic Acid from Sodium 1:7-Iodonaphthalene Sulphonate. ' 86 (6) Reaction of l:7-Diazonaphthalene Sulphonic Acid with an Ammoniacal Solution of fetrammino-Cupric Sulphate Reduced by means of Sulphur Dioxide. 86 V. 1-Naphthylamine-S-Sulphonic Acid. (peri acid). 88 (1) Preparation of Sodium 1-haphthylamine—8-Sulphonate. 88 (2) Diazotization of Peri Acid. 88 (5) Properties of the Diazo-Compound. 89 (4) Preparation of Sodium 1:8-Iodonaphthalene Sulphonate. 91 CONTENTS. - continued. Page. (5) Derivatives of 1:8-Iodonaphthalene Sulphonic Acid. 95 (Sulphonyl chloride, sulphonamide, 1:8-naphthasultam, sulphoanilide, phenyl-1:8-naphthasult am.) (6) Reaction of Sodium 1:8-Iodonaphthalene Sulphonate in Aqueous Solution with Copper Powder. 97 (7) Reaction of l:8-Diazonaphthalene Sulphonic Acid with Cuprous Chloride under Varying Conditions. 99 (8) Preparation of 1:8—Bromonaphthalene Sulphonyl Chloride. 102 (9) Reaction of l:8-Diazonaphthalene Sulphonic Acid with an Ammoniacal Solution of Tatrammino-Cupric Sulphate Reduced by means of Sulphur Dioxide. 104 (10) Reaction of l:8-Diazonaphthalene Sulphonic Acid with an Ammoniacal Solution of Tetrammino-Cuprous Sulphate. 106 (11) Preparation of Naphthostyril and Its Conversion to 1:1* -Dinaphthyl-8:8 1-Die arboxylic Acid. 108 (a) Preparation of 1:8-Cyanonaphthalene Sulphonic Acid. (Also sulphonyl chloride and sulphonamide) 111 (b) Hydrolysis of 1:8-Cyanonaphthalene Sulphonic Acid (Acid and Alkaline). Naphthostyril and Derivatives. 113 (c) Diazotization of l:8-Aminonaphthoic Acid. Reaction of the Diazo-Coinpound with Ammoniacal Cuprous Oxide Solution. 116 (12) Reactions of l:8-Diazonaphthalene Sulphonic Acid Resulting in the Formation of Naphthalene-a-Sulphon­ ic Acid. 117 (13) Various Experiments without ConclusiveResults. 119 (14) Nitration of l:8-Naphthasultone. 120 VI. %-Nanhthvlamine-1-Sulphonic Acid. (Tobias Acid). 123 (1) Preparation of Sodium 2-Naphthylamine-1-Sulphonate. 123 (2) Diazotization of Tobias Acid. 123 (3) Preparation of Potassium 2:l-Iodonaphthalene Sulphonat e. 124 (4) Derivatives of 2:l-Iodonaphthalene Sulphonic Acid. (Sulphonyl chloride and sulphonamide.) 125 (5) Reaction of Potassium 2:1-Iodonaphthalene Sulphon­ ate in Aqueous Solution with Copper Powder. 126 CONTENTS. - continued. Page. (6) Derivatives of 2: 2*-Dinaphthyl-l:l,-Disulphonic Acid. (Disulphonyl chloride, diammonium salt, Bp- dinaphthyl and 1:1* -dihydroxy-2: 2 1-dinaphthyl.) 127 (7) Preparation of Potassium 2:l-Bromonaphthalene Sulphonate. 130 (8) Derivatives of 2:l-Bromonaphthalene Sulphonic Acid. (Sulphonyl chloride and sulphonamide.) 131 (9) Reaction of Potassium 2:l-Bromonaphthalene Sulphon­ ate in Aqueous Solution with Copper Powder. 131 (10) Reaction of 2:1-Diazonaphthalene Sulphonic Acid with an Ammoniacal Solution of Tetrammino-Cupric Sulphate Reduced by means of Sulphur Dioxide. 132 (i d Reaction of 2:1-Diazonaphthalene Sulphonic Acid with an Ammoniacal Solution of Tetrammino-Cuprous Sulphate. 133 (1 2) Reaction of 2:1-Diazonaphthalene Sulphonic Acid with Sodium Sulphite Solution. 135 VII. 2-Naphthylamine-6-Sulphonic Acid. (Brdnner Acid). 138 (1) Preparation of Sodium 2-Saphthylamine-6-Sulphonate. 138 (2) Diazotization of Brbnner Acid. 138 (3) Preparation of Potassium 2;6-Iodonaphthalene e). Sulphonate. (Also sulxjhonyl chloride and sulphonamid 139 (4) Attempt
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