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Chlorosulfuric acid

May 08, 2024

Chlorosulfuric acid (IUPAC name: sulfurochloridic acid) is the inorganic compound with the formula HSO3Cl. It is also known as chlorosulfonic acid, being the sulfonic acid of chlorine. It is a distillable, colorless liquid which is hygroscopic and a powerful lachrymator. Commercial samples usually are pale brown or straw colored.[2]

Chlorosulfuric acid
Names
IUPAC name
Sulfurochloridic acid
Other names
Chlorosulfuric acid,
Chlorosulfonic acid,
Chlorosulphonic acid,
Chlorinesulfonic acid,
Chlorinesulphonic acid,
Chloridosulfonic acid,
Chloridosulphonic acid,
Sulfuric chlorohydrin
Identifiers
  • 7790-94-5 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 23040 Y
ECHA InfoCard 100.029.304
EC Number
  • 232-234-6
  • 24638
RTECS number
  • FX5730000
UNII
  • 2O9AXL1TJ4 Y
UN number 1754
  • DTXSID1029706
  • InChI=1S/ClHO3S/c1-5(2,3)4/h(H,2,3,4) Y
    Key: XTHPWXDJESJLNJ-UHFFFAOYSA-N Y
  • InChI=1/ClHO3S/c1-5(2,3)4/h(H,2,3,4)
    Key: XTHPWXDJESJLNJ-UHFFFAOYAO
  • ClS(=O)(=O)O
Properties
HSO3Cl
Molar mass 116.52 g mol−1
Appearance colorless liquid, but commercial samples usually are pale brown
Density 1.753 g cm−3
Melting point −80 °C (−112 °F; 193 K)
Boiling point 151 to 152 °C (304 to 306 °F; 424 to 425 K) (755 mmHg or 100.7 kPa)
hydrolysis
Solubility in other solvents reacts with alcohols
soluble in chlorocarbons
1.433
Structure
tetrahedral
Hazards
GHS labelling:
Danger
H314, H335
P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W+OX: Reacts with water in an unusual or dangerous manner AND is oxidizer
3
0
2
W
OX
Safety data sheet (SDS) ICSC 1039
Related compounds
Related compounds
 Sulfuryl chloride
Sulfuric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Salts and esters of chlorosulfuric acid are known as chlorosulfates.

Structure and properties edit

Chlorosulfuric acid is a tetrahedral molecule. The formula is more descriptively written SO2(OH)Cl, but HSO3Cl is traditional. It is an intermediate, chemically and conceptually, between sulfuryl chloride (SO2Cl2) and sulfuric acid (H2SO4).[3] The compound is rarely obtained pure. Upon standing with excess sulfur trioxide, it decomposes to pyrosulfuryl chlorides:[4]

2 ClSO3H + SO3 → H2SO4 + S2O5Cl2

Synthesis edit

The industrial synthesis entails the reaction of hydrogen chloride with a solution of sulfur trioxide in sulfuric acid:[4]

HCl + SO3 → ClSO3H

It can also be prepared by chlorination of sulfuric acid, written here for pedagogical purposes as HSO3(OH), vs. the usual format H2SO4:

PCl5 + HSO3(OH) → HSO3Cl + POCl3 + HCl

The latter method is more suited for laboratory-scale operations.

Applications edit

ClSO2OH is used to prepare alkyl sulfates, which are useful as detergents and as chemical intermediates:

ROH + ClSO3H → ROSO3H + HCl

An early synthesis of saccharin begins with the reaction of toluene with ClSO2OH to give the ortho- and para-toluenesulfonyl chloride derivatives:

CH3C6H5 + 2 ClSO2OH → CH3C6H4SO2Cl + H2SO4 + HCl

Oxidation of the ortho isomer gives the benzoic acid derivative that then is cyclized with ammonia and neutralized with base to afford saccharin.

Reaction with hydrogen peroxide is used to produce peroxydisulfuric acid ("persulfuric acid") and peroxydisulfates. These are used as oxidizing agents and for initiating free radical polymerization, for example to produce polytetrafluoroethylene (Teflon).

Chlorosulfonic acid has been used as an anti-contrail agent in Ryan Model 147 reconnaissance drones,[5] and to produce smoke screens.[6][7]

Safety edit

ClSO3H reacts violently with water to yield sulfuric acid and hydrogen chloride, commonly seen as vapors fuming from the liquid:

ClSO3H + H2O → H2SO4 + HCl

Precautions should be taken, such as proper ventilation associated with HCl.

Related halosulfuric acids edit

References edit

  1. ^ "New Environment Inc. - NFPA Chemicals".
  2. ^ Cremlyn, R. J. (2002). Chlorosulfonic Acid. Royal Society of Chemistry. ISBN 978-0-85404-498-6.
  3. ^ Holleman, A. F.; Wiberg, E. (2001). Inorganic Chemistry. San Diego: Academic Press. pp. 549–550.
  4. ^ a b Maas, J.; Baunack, F. (2002). "Chlorosulfuric Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_017. ISBN 3527306730.
  5. ^ Method and apparatus for suppressing contrails (PDF). United States Patent and Trademark Office. 1970.
  6. ^ The Royal Navy at War (DVD). London: Imperial War Museum. 2005.
  7. ^ Amos, Jonathan (2018-04-11). "Nazi legacy found in Norwegian trees". BBC News Online. Retrieved 2018-04-17.

May 08, 2024
chlorosulfuric, acid, iupac, name, sulfurochloridic, acid, inorganic, compound, with, formula, hso3cl, also, known, chlorosulfonic, acid, being, sulfonic, acid, chlorine, distillable, colorless, liquid, which, hygroscopic, powerful, lachrymator, commercial, sa. Chlorosulfuric acid IUPAC name sulfurochloridic acid is the inorganic compound with the formula HSO3Cl It is also known as chlorosulfonic acid being the sulfonic acid of chlorine It is a distillable colorless liquid which is hygroscopic and a powerful lachrymator Commercial samples usually are pale brown or straw colored 2 Chlorosulfuric acid Names IUPAC name Sulfurochloridic acid Other names Chlorosulfuric acid Chlorosulfonic acid Chlorosulphonic acid Chlorinesulfonic acid Chlorinesulphonic acid Chloridosulfonic acid Chloridosulphonic acid Sulfuric chlorohydrin Identifiers CAS Number 7790 94 5 Y 3D model JSmol Interactive image ChemSpider 23040 Y ECHA InfoCard 100 029 304 EC Number 232 234 6 PubChem CID 24638 RTECS number FX5730000 UNII 2O9AXL1TJ4 Y UN number 1754 CompTox Dashboard EPA DTXSID1029706 InChI InChI 1S ClHO3S c1 5 2 3 4 h H 2 3 4 YKey XTHPWXDJESJLNJ UHFFFAOYSA N YInChI 1 ClHO3S c1 5 2 3 4 h H 2 3 4 Key XTHPWXDJESJLNJ UHFFFAOYAO SMILES ClS O O O Properties Chemical formula HSO3Cl Molar mass 116 52 g mol 1 Appearance colorless liquid but commercial samples usually are pale brown Density 1 753 g cm 3 Melting point 80 C 112 F 193 K Boiling point 151 to 152 C 304 to 306 F 424 to 425 K 755 mmHg or 100 7 kPa Solubility in water hydrolysis Solubility in other solvents reacts with alcoholssoluble in chlorocarbons Refractive index nD 1 433 Structure Molecular shape tetrahedral Hazards GHS labelling Pictograms Signal word Danger Hazard statements H314 H335 Precautionary statements P260 P261 P264 P271 P280 P301 P330 P331 P303 P361 P353 P304 P340 P305 P351 P338 P310 P312 P321 P363 P403 P233 P405 P501 NFPA 704 fire diamond 302W OX Safety data sheet SDS ICSC 1039 Related compounds Related compounds Sulfuryl chlorideSulfuric acid Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Salts and esters of chlorosulfuric acid are known as chlorosulfates Contents 1 Structure and properties 2 Synthesis 3 Applications 4 Safety 5 Related halosulfuric acids 6 ReferencesStructure and properties editChlorosulfuric acid is a tetrahedral molecule The formula is more descriptively written SO2 OH Cl but HSO3Cl is traditional It is an intermediate chemically and conceptually between sulfuryl chloride SO2Cl2 and sulfuric acid H2SO4 3 The compound is rarely obtained pure Upon standing with excess sulfur trioxide it decomposes to pyrosulfuryl chlorides 4 2 ClSO3H SO3 H2SO4 S2O5Cl2Synthesis editThe industrial synthesis entails the reaction of hydrogen chloride with a solution of sulfur trioxide in sulfuric acid 4 HCl SO3 ClSO3H It can also be prepared by chlorination of sulfuric acid written here for pedagogical purposes as HSO3 OH vs the usual format H2SO4 PCl5 HSO3 OH HSO3Cl POCl3 HCl The latter method is more suited for laboratory scale operations Applications editClSO2OH is used to prepare alkyl sulfates which are useful as detergents and as chemical intermediates ROH ClSO3H ROSO3H HCl An early synthesis of saccharin begins with the reaction of toluene with ClSO2OH to give the ortho and para toluenesulfonyl chloride derivatives CH3C6H5 2 ClSO2OH CH3C6H4SO2Cl H2SO4 HCl Oxidation of the ortho isomer gives the benzoic acid derivative that then is cyclized with ammonia and neutralized with base to afford saccharin Reaction with hydrogen peroxide is used to produce peroxydisulfuric acid persulfuric acid and peroxydisulfates These are used as oxidizing agents and for initiating free radical polymerization for example to produce polytetrafluoroethylene Teflon Chlorosulfonic acid has been used as an anti contrail agent in Ryan Model 147 reconnaissance drones 5 and to produce smoke screens 6 7 Safety editClSO3H reacts violently with water to yield sulfuric acid and hydrogen chloride commonly seen as vapors fuming from the liquid ClSO3H H2O H2SO4 HCl Precautions should be taken such as proper ventilation associated with HCl Related halosulfuric acids editFluorosulfonic acid FSO2OH is a related strong acid with a diminished tendency to evolve hydrogen fluoride Bromosulfonic acid BrSO2OH is unstable decomposing at its melting point of 8 C to give bromine sulfur dioxide and sulfuric acid Iodosulfonic acid is not known to occur References edit New Environment Inc NFPA Chemicals Cremlyn R J 2002 Chlorosulfonic Acid Royal Society of Chemistry ISBN 978 0 85404 498 6 Holleman A F Wiberg E 2001 Inorganic Chemistry San Diego Academic Press pp 549 550 a b Maas J Baunack F 2002 Chlorosulfuric Acid Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a07 017 ISBN 3527306730 Method and apparatus for suppressing contrails PDF United States Patent and Trademark Office 1970 The Royal Navy at War DVD London Imperial War Museum 2005 Amos Jonathan 2018 04 11 Nazi legacy found in Norwegian trees BBC News Online Retrieved 2018 04 17 Retrieved from https en wikipedia org w index php title Chlorosulfuric acid amp oldid 1219013345, wikipedia, wiki, book, books, library,

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