Sulfuryl Chloride
Organic Syntheses with Sulfuryl Chloride
Binkley,W;Degering,Ed
J. Am. Chem. Soc.
Vol.61(12) 1939 pp.3250-
DOI: 10.1021/ja01267a004
http://pubs.acs.org/doi/abs/10.1021/ja01267a004
Abstract
The present investigation is a study of sulfuryl chloride in condensation reactions with the lower aliphatic alcohols and the lower dialkylamines.
A New, Mild Preparation of Sulfonyl Chlorides
Blotny,Grzegorz
Tetrahedron Letters
Vol.44(7) 2003 pp.1499-1501
DOI: 10.1016/S0040-4039(02)02853-8
http://tinyurl.com/283u83k
Abstract
A new method was developed for the preparation of sulfonyl chlorides from sulfonic acids under neutral conditions using 2,4,6-trichloro-1,3,5-triazine as chlorinating agent.
Chlorinations with Sulfuryl Chloride. I. The Peroxide-Catalyzed Chlorination of Hydrocarbons
Kharasch,M;Brown,Herbert
J. Am. Chem. Soc.
Vol.61(8.) 1939 pp.2142–2150
DOI: 10.1021/ja01877a048
http://pubs.acs.org/doi/abs/10.1021/ja01877a048
Abstract
In the past the use of sulfuryl chloride as a chlorinating agent has depended upon the dissociation of the compound, under the experimental conditions, into its components - sulfur dioxide and chlorine. That is, the sulfuryl chloride served as a source of molecular chlorine, and it has been used almost exclusively for the chlorination of aromatic nuclei in the presence of halogen carriers.
Chlorinations with Sulfuryl Chloride. II. The Peroxide-Catalyzed Reaction of Sulfuryl Chloride with Ethylenic Compounds
Kharasch,M;Brown,Herbert
J. Am. Chem. Soc
Vol.61(12) 1939 pp.3432–3434
DOI: 10.1021/ja01267a058
http://pubs.acs.org/doi/abs/10.1021/ja01267a058
Abstract
Sulfuryl chloride reacts readily with most ethylenic compounds to yield the saturated dichloro derivatives and sulfur dioxide. Although this reaction has been used for synthetic purposes, no thorough study has been made of the factors which control these additions.
Chlorinations with Sulfuryl Chloride. III. (a) The Peroxide-Catalyzed Chlorination of Aliphatic Acids and Acid Chlorides. (b) The Photochemical Sulfonation of Aliphatic Acids
Kharasch,M;Brown,Herbert
J. Am. Chem. Soc.
Vol.62(4) 1940 pp.925–929
DOI: 10.1021/ja01861a061
http://pubs.acs.org/doi/abs/10.1021/ja01861a061
Abstract
In an earlier paper it was shown that various types of hydrocarbons can be chlorinated rapidly and conveniently by sulfuryl chloride in the presence of a small quantity of an organic peroxide. It was suggested that the reaction depends upon the initiation by the peroxide of a chain reaction involving chlorine atoms.
Solvent Effects in the Reactions of Free Radicals and Atoms. IV. Effect of Aromatic Solvents in Sulfuryl Chloride Chlorinations
Russell,Glen
J. Am. Chem. Soc.
Vol.80(18) 1958 pp.5002–5003
DOI: 10.1021/ja01551a058
http://pubs.acs.org/doi/abs/10.1021/ja01551a058
Abstract
Photochemical chlorination and sulfuryl chloride chlorination give different products in the chlorination of branched chain hydrocarbons. This has been interpreted as being due to equilibrium (1) and to the lower reactivity of the SO2Cl radical relative to the chlorine atom. In aromatic solvents little difference is noted between the products of photochlorination and sulfuryl chloride chlorination, possibly because in both types of chlorination most of the chlorine atoms are complexed with the solvent, equations 2 and 3.
Sulfuryl Chloride in Organic Chemistry
Brown,Herbert
Ind. Eng. Chem.
Vol.36(9) 1944 pp.785–791
DOI: 10.1021/ie50417a003
http://pubs.acs.org/doi/abs/10.1021/ie50417a003
Abstract
Sulfuryl chloride is a versatile reagent with great potentialities in organic synthesis. Under appropriate conditions it may be used for the chlorination and sulfonation of both aliphatic and aromatic derivatives. It may also be applied as an acylating and condensing agent. The simplicity of these reactions, their ease of control, and their high yields promise ot make the reagent particularly useful in many applications which require simple adn unspecialized equipment.
Sulfuryl Chloride: I. Principles of Manufacture from Liquid Sulfur Dioxide
McKee,Ralph;Salls,Carroll
Ind. Eng. Chem.
Vol.16(3) 1924 pp.279–282
DOI: 10.1021/ie50171a025
http://pubs.acs.org/doi/abs/10.1021/ie50171a025
Abstract
Sulfuryl chloride has been one of the medium priced chemicals, but one which, if the cost were cheap enough, would have a much more extensive use.
Basing their work on the modern theories of contact catalysis, the authors have worked out a new method for the manufacture of sulfuryl chloride which promises to place this chemical industrially in the "heavy chemical market" class. Over 99 per cent yield of 98 per cent purity sulfuryl chloride is obtained by direct combination at room temperature in iron apparatus of pure sulfur dioxide and chlorine, and removal of the catalyst by filtration.
Sulfuryl Chloride: II. Principles of Manufacture from Sulfur Burner Gas
McKee,Ralph;Salls,Carroll
Abstract
Ind. Eng. Chem.
Vol.16(4) 1924 pp.351–353
DOI: 10.1021/ie50172a008
http://pubs.acs.org/doi/abs/10.1021/ie50172a008
Abstract
In this method cheap, dilute gases are dried and brought into contact with active carbon of the proper type, and by cooling and use of absorbents the sulfuryl chloride is recovered for shipment. This is believed to be the first method that has been proposed which permits the use of dilute gases - eg. 14 per cent sulfur dioxide - in the making of sulfuryl chloride.
Sulfuryl Chloride: III. Hydrolysis to Sulfuric and Hydrochloric Acids
Ind. Eng. Chem.
Vol.16(8.) 1924 pp.833–836
DOI: 10.1021/ie50176a027
http://pubs.acs.org/doi/abs/10.1021/ie50176a027
Abstract
if all the hydrochloric acid used in the United States were made from chlorine, 150 tonnes of chlorine per day would be required. In 1918 the liquid chlorine-producing capacity of the United States was 22 tons per day. The writers propose combining chlorine with sulfur dioxide and shipping the anhydrous liquid sulfuryl chloride in iron drums to the place where the hydrochloric acid is wanted and there adding steam to produce pure hydrogen chloride gas and 60 to 70 per cent sulfuric acid. The writers do not claim that this new process can compete in all localities with present processes, but there are some local conditions and special uses for which this process is especially adapted. The production of dry hydrogen chloride gas and dilute mixtures of sulfuric acid and hydrochloric acid are two special uses.
Organic Syntheses with Sulfuryl Chloride
Binkley,W;Degering,Ed
J. Am. Chem. Soc.
Vol.61(12) 1939 pp.3250-
DOI: 10.1021/ja01267a004
http://pubs.acs.org/doi/abs/10.1021/ja01267a004
Abstract
The present investigation is a study of sulfuryl chloride in condensation reactions with the lower aliphatic alcohols and the lower dialkylamines.
A New, Mild Preparation of Sulfonyl Chlorides
Blotny,Grzegorz
Tetrahedron Letters
Vol.44(7) 2003 pp.1499-1501
DOI: 10.1016/S0040-4039(02)02853-8
http://tinyurl.com/283u83k
Abstract
A new method was developed for the preparation of sulfonyl chlorides from sulfonic acids under neutral conditions using 2,4,6-trichloro-1,3,5-triazine as chlorinating agent.
Chlorinations with Sulfuryl Chloride. I. The Peroxide-Catalyzed Chlorination of Hydrocarbons
Kharasch,M;Brown,Herbert
J. Am. Chem. Soc.
Vol.61(8.) 1939 pp.2142–2150
DOI: 10.1021/ja01877a048
http://pubs.acs.org/doi/abs/10.1021/ja01877a048
Abstract
In the past the use of sulfuryl chloride as a chlorinating agent has depended upon the dissociation of the compound, under the experimental conditions, into its components - sulfur dioxide and chlorine. That is, the sulfuryl chloride served as a source of molecular chlorine, and it has been used almost exclusively for the chlorination of aromatic nuclei in the presence of halogen carriers.
Chlorinations with Sulfuryl Chloride. II. The Peroxide-Catalyzed Reaction of Sulfuryl Chloride with Ethylenic Compounds
Kharasch,M;Brown,Herbert
J. Am. Chem. Soc
Vol.61(12) 1939 pp.3432–3434
DOI: 10.1021/ja01267a058
http://pubs.acs.org/doi/abs/10.1021/ja01267a058
Abstract
Sulfuryl chloride reacts readily with most ethylenic compounds to yield the saturated dichloro derivatives and sulfur dioxide. Although this reaction has been used for synthetic purposes, no thorough study has been made of the factors which control these additions.
Chlorinations with Sulfuryl Chloride. III. (a) The Peroxide-Catalyzed Chlorination of Aliphatic Acids and Acid Chlorides. (b) The Photochemical Sulfonation of Aliphatic Acids
Kharasch,M;Brown,Herbert
J. Am. Chem. Soc.
Vol.62(4) 1940 pp.925–929
DOI: 10.1021/ja01861a061
http://pubs.acs.org/doi/abs/10.1021/ja01861a061
Abstract
In an earlier paper it was shown that various types of hydrocarbons can be chlorinated rapidly and conveniently by sulfuryl chloride in the presence of a small quantity of an organic peroxide. It was suggested that the reaction depends upon the initiation by the peroxide of a chain reaction involving chlorine atoms.
Solvent Effects in the Reactions of Free Radicals and Atoms. IV. Effect of Aromatic Solvents in Sulfuryl Chloride Chlorinations
Russell,Glen
J. Am. Chem. Soc.
Vol.80(18) 1958 pp.5002–5003
DOI: 10.1021/ja01551a058
http://pubs.acs.org/doi/abs/10.1021/ja01551a058
Abstract
Photochemical chlorination and sulfuryl chloride chlorination give different products in the chlorination of branched chain hydrocarbons. This has been interpreted as being due to equilibrium (1) and to the lower reactivity of the SO2Cl radical relative to the chlorine atom. In aromatic solvents little difference is noted between the products of photochlorination and sulfuryl chloride chlorination, possibly because in both types of chlorination most of the chlorine atoms are complexed with the solvent, equations 2 and 3.
Sulfuryl Chloride in Organic Chemistry
Brown,Herbert
Ind. Eng. Chem.
Vol.36(9) 1944 pp.785–791
DOI: 10.1021/ie50417a003
http://pubs.acs.org/doi/abs/10.1021/ie50417a003
Abstract
Sulfuryl chloride is a versatile reagent with great potentialities in organic synthesis. Under appropriate conditions it may be used for the chlorination and sulfonation of both aliphatic and aromatic derivatives. It may also be applied as an acylating and condensing agent. The simplicity of these reactions, their ease of control, and their high yields promise ot make the reagent particularly useful in many applications which require simple adn unspecialized equipment.
Sulfuryl Chloride: I. Principles of Manufacture from Liquid Sulfur Dioxide
McKee,Ralph;Salls,Carroll
Ind. Eng. Chem.
Vol.16(3) 1924 pp.279–282
DOI: 10.1021/ie50171a025
http://pubs.acs.org/doi/abs/10.1021/ie50171a025
Abstract
Sulfuryl chloride has been one of the medium priced chemicals, but one which, if the cost were cheap enough, would have a much more extensive use.
Basing their work on the modern theories of contact catalysis, the authors have worked out a new method for the manufacture of sulfuryl chloride which promises to place this chemical industrially in the "heavy chemical market" class. Over 99 per cent yield of 98 per cent purity sulfuryl chloride is obtained by direct combination at room temperature in iron apparatus of pure sulfur dioxide and chlorine, and removal of the catalyst by filtration.
Sulfuryl Chloride: II. Principles of Manufacture from Sulfur Burner Gas
McKee,Ralph;Salls,Carroll
Abstract
Ind. Eng. Chem.
Vol.16(4) 1924 pp.351–353
DOI: 10.1021/ie50172a008
http://pubs.acs.org/doi/abs/10.1021/ie50172a008
Abstract
In this method cheap, dilute gases are dried and brought into contact with active carbon of the proper type, and by cooling and use of absorbents the sulfuryl chloride is recovered for shipment. This is believed to be the first method that has been proposed which permits the use of dilute gases - eg. 14 per cent sulfur dioxide - in the making of sulfuryl chloride.
Sulfuryl Chloride: III. Hydrolysis to Sulfuric and Hydrochloric Acids
Ind. Eng. Chem.
Vol.16(8.) 1924 pp.833–836
DOI: 10.1021/ie50176a027
http://pubs.acs.org/doi/abs/10.1021/ie50176a027
Abstract
if all the hydrochloric acid used in the United States were made from chlorine, 150 tonnes of chlorine per day would be required. In 1918 the liquid chlorine-producing capacity of the United States was 22 tons per day. The writers propose combining chlorine with sulfur dioxide and shipping the anhydrous liquid sulfuryl chloride in iron drums to the place where the hydrochloric acid is wanted and there adding steam to produce pure hydrogen chloride gas and 60 to 70 per cent sulfuric acid. The writers do not claim that this new process can compete in all localities with present processes, but there are some local conditions and special uses for which this process is especially adapted. The production of dry hydrogen chloride gas and dilute mixtures of sulfuric acid and hydrochloric acid are two special uses.
Binkley.Degering.Organic.Syntheses.with.Sulfuryl.Chloride.pdf