SULFOLANE (ANHYDROUS - AQUEOUS)

CAS Number    : 126-33-0 
EC Number    : 204-783-1
IUPAC name: 1λ6-Thiolane-1,1-dione

DESCRIPTION:

Sulfolane (also tetramethylene sulfone, systematic name: 1λ6-thiolane-1,1-dione) is an organosulfur compound, formally a cyclic sulfone, with the formula (CH2)4SO2. 
Sulfolane (Anhydrous - Aqueous) is a colorless liquid commonly used in the chemical industry as a solvent for extractive distillation and chemical reactions. 
Sulfolane was originally developed by the Shell Oil Company in the 1960s as a solvent to purify butadiene. 
Sulfolane is a polar aprotic solvent, and it is readily soluble in water.
Sulfolane is a colorless oily liquid with a weak oily odor. 
Solidifies (freezing point is 79° F) and sinks on first contact with water, then mixes with water. 
Sulfolane is a member of the class of tetrahydrothiophenes that is tetrahydrothiophene in which the sulfur has been oxidised to give the corresponding sulfone. 
A colourless, high-boiling (285℃) liquid that is miscible with both water and hydrocarbons, Sulfolane is used as an industrial solvent, particularly for the purification of hydrocarbon mixtures by liquid-vapour extraction. 
Sulfolane has a role as a polar aprotic solvent. 
Sulfolane is a sulfone and a member of tetrahydrothiophenes. 
Sulfolane derives from a hydride of a tetrahydrothiophene.
Sulfolane is a natural product found in Lissoclinum and Batzella with data available.

Sulfolane is classified as a sulfone, a group of organosulfur compounds containing a sulfonyl functional group. 
The sulfone group is a sulfur atom doubly bonded to two oxygen atoms and singly bonded to two carbon centers. 
The sulfur-oxygen double bond is polar, conferring good solubility in water, while the four carbon ring provides non-polar stability. 
These properties allow Sulfolane (Anhydrous - Aqueous) to be miscible in both water and hydrocarbons, resulting in its widespread use as a solvent for purifying hydrocarbon mixtures.
Sulfolane (Anhydrous - Aqueous) Is an organosulfur compound.  
Sulfolane (Anhydrous - Aqueous) is commonly used in the chemical industry as a dipolar aprotic solvent in many chemical reactions and chiefly utilized for extractive distillation. 
Its key applications are aromatics extraction also known as BTX extraction and in gas sweetening process called Sulfinol Gas Treatment Process. 
Because of its high thermal stability, sulfolane can be operated at wide range of temperatures.
Sulfolane is a solvent that can be used as a replacement for trifluoroacetic acid (TFA) in biological treatment.
Sulfolane has a similar chemical structure to TFA and can be used in the same model systems, such as hydrogen fluoride (HF), water vapor, and hydrochloric acid (HCl). 
Sulfolane is also an excellent alternative to TFA for sample preparation because it does not react with copper chloride. 
In addition, sulfolane has been shown to have anti-inflammatory properties.

CAS Number    : 126-33-0 
EC Number    : 204-783-1
IUPAC name: 1λ6-Thiolane-1,1-dione

SYNTHESIS OF SULFOLANE (ANHYDROUS - AQUEOUS):
The original method developed by the Shell Oil Company was to first allow butadiene to react with sulfur dioxide via a cheletropic reaction to give sulfolene. 
This was then hydrogenated using Raney nickel as a catalyst to give sulfolane.

Shortly thereafter, it was discovered that both the product yield and the lifetime of the catalyst could be improved by adding hydrogen peroxide and then neutralizing to a pH of roughly 5-8 before hydrogenation. 
Developments have continued over the years, including in the catalysts used. 
Recently, it was found that Ni-B/MgO showed superior catalytic activity to that of Raney nickel and other common catalysts that have been used in the hydrogenation of sulfolene.
Other syntheses have also been developed, such as oxidizing tetrahydrothiophene with hydrogen peroxide. 
This reaction produces tetramethylene sulfoxide, which can then be further oxidized. 
Because the first oxidation occurs at low temperature and the second at higher temperature, the reaction can be controlled at each stage.
This gives greater freedom for the manipulation of the reaction, which can potentially lead to higher yields and purity.
APPLICATIONS OF SULFOLANE:
Sulfolane is a polar aprotic solvent that may be used for the complete pyrolysis of cellulose without any polymerization or carbonization side reaction. 
Sulfolane, in combination with mesitylene, can be used as a solvent in the synthesis of poly(succinimide) (PSI) from L-aspartic acid.
Sulfolane can also be used as a solvent in the synthesis of chlorine-terminated polyethersulfone oligomer, a polymeric activator for nylon 6-polyethersulfone (PES)-nylon 6 block copolymer synthesis.
SULFOLANE is Used in Acid Gas Treatment: (Sulfinol Process / Gas sweetening Process)
SULFOLANE is Used in Aromatics Extraction: (Shell / UOP Sulfolane Process)
SULFOLANE is Used in Pharmaceuticals: (Synthesis of intermediates and as a process solvent)
SULFOLANE is Used in Agrochemicals/Fertilizers
SULFOLANE is Used in Polymer/Textile Processing
SULFOLANE is Used in Printing Inks: Jets
SULFOLANE is Used in Plastics: Engineering & Medical (Advanced Polymers)
SULFOLANE is Used in Electronics and Electrolysis
SULFOLANE is Used in Extractive Distillation
SULFOLANE is Used in Fractionation
SULFOLANE is Used in Reaction Solvent
SULFOLANE is Used in Dyestuffs

USES OF SULFOLANE (ANHYDROUS - AQUEOUS):
Sulfolane is widely used as an industrial solvent, especially in the extraction of aromatic hydrocarbons from hydrocarbon mixtures and to purify natural gas. 
The first large scale commercial use of sulfolane, the sulfinol process, was first implemented by Shell Oil Company in March 1964 at the Person gas plant near Karnes City, Texas. 
The sulfinol process purifies natural gas by removing H2S, CO2, COS and mercaptans from natural gas with a mixture of alkanolamine and sulfolane.

Shortly after the sulfinol process was implemented, sulfolane was found to be highly effective in separating high purity aromatic compounds from hydrocarbon mixtures using liquid-liquid extraction. This process is widely used in refineries and the petrochemical industry. 
Because sulfolane is one of the most efficient industrial solvents for purifying aromatics, the process operates at a relatively low solvent-to-feed ratio, making sulfolane relatively cost effective compared to similar-purpose solvents. 
In addition, it is selective in a range that complements distillation; where sulfolane cannot separate two compounds, distillation easily can and vice versa, keeping sulfolane units useful for a wide range of compounds with minimal additional cost.

Whereas sulfolane is highly stable and can therefore be reused many times, it does eventually degrade into acidic byproducts. 
A number of measures have been developed to remove these byproducts, allowing the sulfolane to be reused and increase the lifetime of a given supply. 
Some methods that have been developed to regenerate spent sulfolane include vacuum and steam distillation, back extraction, adsorption, and anion-cation exchange resin columns.

Sulfolane is also added to hydrofluoric acid as a vapor suppressant, commonly for use in a refinery's alkylation unit. 
This "modified" hydrofluoric acid is less prone to vaporization if released in its liquid form.

AS A POLLUTANT
Groundwater in parts of the city of North Pole, Alaska, has been contaminated with sulfolane due to pollution from a now-closed petroleum refinery.
Due to this contamination, affected residents have been supplied with alternative potable water sources. 
Animal studies on the toxicity of sulfolane are ongoing, funded through the US federal government's National Toxicology Program.
No long-term in vivio animal studies have been done, which prevents any firm conclusion as to whether sulfolane is a carcinogen, although in vitro studies have failed to demonstrate any cancerous changes in bacterial or animal cells. In animal studies, high doses of sulfolane have induced negative impacts on the central nervous system, including hyperactivity, convulsions and hypothermia; the impacts of lower doses, especially over the long-term, are still being studied.

USES:
•    Acid gas treatment
•    Aromatic extraction
•    Chemical syntheses especially in pharmaceutical sector
•    Formulation of printing inks
•    In textile processing
•    Electronics and Electrolysis
•    In Fractionatione operated at wide range of temperatures.

CAS Number    : 126-33-0 
EC Number    : 204-783-1
IUPAC name: 1λ6-Thiolane-1,1-dione

CHEMICAL AND PHYSICAL PROPERTIES OF SULFOLANE (ANHYDROUS - AQUEOUS):
Flash point:    165 °C (329 °F; 438 K)
Autoignition temperature:    528 °C (982 °F; 801 K)
Chemical formula:    C4H8O2S
Molar mass:    120.17 g•mol−1
Appearance:    Clear colorless liquid
Density    :1.261 g/cm3, liquid
Melting point:    27.5 °C (81.5 °F; 300.6 K)
Boiling point:    285 °C (545 °F; 558 K)
Solubility in water:    miscible
Viscosity:    0.01007 Pa•s at 25 °C
Structure: Dipole moment    4.35 D
Molecular Weight:    120.17    
XLogP3:    -0.8    
Hydrogen Bond Donor Count:    0    
Hydrogen Bond Acceptor Count:    2
Rotatable Bond Count:    0    
Exact Mass:    120.02450067    
Monoisotopic Mass:    120.02450067    
Topological Polar Surface Area:    42.5 Ų    
Heavy Atom Count:    7    
Formal Charge:    0    
Complexity:    128    
Isotope Atom Count:    0    
Defined Atom Stereocenter Count:    0    
Undefined Atom Stereocenter Count:    0    
Defined Bond Stereocenter Count:    0    
Undefined Bond Stereocenter Count:    0    
Covalently-Bonded Unit Count:    1    
Compound Is Canonicalized:    Yes
Color/Form:
White or creamy white, crystalline powder
Odor: Odorless
Taste:
Slightly bitter taste
Henry's Law constant = 4.8X10-6 atm-cu m/mole (est)
Decomposition
When heated to decomposition it emits toxic fumes of /sulfur oxide/.
Apperance: Colorless or pale yellow transparent liquid
Purity:                                               ≥99.5%
5% Distil off Temperature:              ≥282°C
95% Distil off Temperature:            ≤288°C
Moisture(m/m):                                  ≤ 0.1
Sulfur Content(m/m):                      26-27
2-Sulfolene(m/m):                            ≤0.2
ISO Propyl Sulfolance aether(m/m): ≤0.2
Ash Content:                                    ≤0.1
Thermal Stability(mgSO2/Kg):           ≤16
Uses: Solvent or intermediates.

CAS Number    : 126-33-0 
EC Number    : 204-783-1
IUPAC name: 1λ6-Thiolane-1,1-dione

SAFETY INFORMATION ABOUT SULFOLANE (ANHYDROUS - AQUEOUS):

First aid measures:
General advice : Move out of dangerous area.
If inhaled : If unconscious, place in recovery position and seek medical advice. If symptoms persist, call a physician.
In case of eye contact : Flush eyes with water as a precaution. 
Remove contact lenses. 
Protect unharmed eye. 
Keep eye wide open while rinsing. 
If eye irritation persists, consult a specialist.
If swallowed : Keep respiratory tract clear. 
Do not give milk or alcoholic beverages. 
Never give anything by mouth to an unconscious person. 
If symptoms persist, call a physician.
Take victim immediately to hospital.
Firefighting measures:
Flash point : 166°C (331°F)
Method: closed cup
Unsuitable extinguishing media : High volume water jet.
Specific hazards during fire fighting: Do not allow run-off from fire fighting to enter drains or water
courses.
Special protective equipment for fire-fighters: Wear self-contained breathing apparatus for firefighting if necessary.
Further information : Collect contaminated fire extinguishing water separately. 
This must not be discharged into drains. 
Fire residues and contaminated fire extinguishing water must be disposed of in accordance with local regulations.
Fire and explosion protection: Normal measures for preventive fire protection.
Hazardous decomposition products: Carbon oxides. 
Sulfur oxides.
Accidental release measures
Personal precautions : Use personal protective equipment.
Environmental precautions : Prevent product from entering drains. 
Prevent further leakage or spillage if safe to do so. 
If the product contaminates rivers
and lakes or drains inform respective authorities.
Methods for cleaning up : Soak up with inert absorbent material (e.g. sand, silica gel, acid
binder, universal binder, sawdust). Keep in suitable, closed containers for disposal.
Handling and storage
Handling:
Advice on safe handling : Do not breathe vapors/dust. 
Avoid exposure - obtain special instructions before use. 
Avoid contact with skin and eyes. 
Smoking, eating and drinking should be prohibited in the application area. 
Dispose of rinse water in accordance with local and national regulations.
Advice on protection against fire and explosion : Normal measures for preventive fire protection.
Storage:
Requirements for storage areas and containers: Keep container tightly closed in a dry and well-ventilated place.
Observe label precautions. 
Electrical installations / working materials must comply with the technological safety standards.
Use : Solvent
Exposure controls/personal protection
Chevron Phillips Chemical Company LP
Components Basis Value Control parameters Note
Sulfolane Manufacturer TWA 0.37 ppm,
Engineering measures:
Adequate ventilation to control airborned concentrations below the exposure guidelines/limits.
Consider the potential hazards of this material, applicable exposure limits, job
activities, and other substances in the work place when designing engineering controls and selecting
personal protective equipment. 
If engineering controls or work practices are not adequate to prevent exposure to harmful levels of this material, the personal protective equipment listed below is recommended. 
The user should read and understand all instructions and limitations supplied with the equipment since protection is usually provided for a limited time or under certain circumstances.
Personal protective equipment:
Respiratory protection : Wear a supplied-air NIOSH approved respirator unless ventilation or other engineering controls are adequate to maintain minimal oxygen content of 19.5% by volume under
normal atmospheric pressure. 
Wear a NIOSH approved respirator that provides protection when working with this material if exposure to harmful levels of airborne material may occur, such as:
Use a positive pressure, air-supplying respirator if there is potential for uncontrolled release, aerosolization, exposure levels are not known, or other circumstances where air-purifying respirators may not provide adequate protection.

Hand protection : The suitability for a specific workplace should be discussed
with the producers of the protective gloves. 
Please observe the instructions regarding permeability and breakthrough time which are provided by the supplier of the gloves. 
Also take into consideration the specific local conditions under which the
product is used, such as the danger of cuts, abrasion, and the contact time. 
Gloves should be discarded and replaced if there is any indication of degradation or chemical breakthrough.
Eye protection : Eye wash bottle with pure water.
Tightly fitting safety goggles.
Skin and body protection : Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place. 
Wear as appropriate:. Protective suit.
Safety shoes.
Hygiene measures : When using do not eat or drink.
When using do not smoke.
Wash hands before breaks and at the end of workday.
Stability and reactivity:
Reactivity : Stable under recommended storage conditions.
Chemical stability : This material is considered stable under normal ambient and anticipated storage and handling conditions of temperature and pressure.
Possibility of hazardous reactions:
Hazardous reactions : Hazardous reactions: Hazardous polymerization does not occur.
Materials to avoid : May react with oxygen and strong oxidizing agents, such as chlorates, nitrates, peroxides, etc.
Hazardous decomposition products: Carbon oxides
Sulfur oxides
Other data : No decomposition if stored and applied as directed. 
Disposal considerations:
The information in this SDS pertains only to the product as shipped.
Use material for its intended purpose or recycle if possible. 
This material, if it must be discarded,
may meet the criteria of a hazardous waste as defined by US EPA under RCRA (40 CFR 261) or
other State and local regulations. 
Measurement of certain physical properties and analysis for regulated components may be necessary to make a correct determination. 
If this material is classified as a hazardous waste, federal law requires disposal at a licensed hazardous waste disposal facility.
Product : Do not dispose of waste into sewer. 
Do not contaminate ponds, waterways or ditches with chemical or used container.
Send to a licensed waste management company.
Contaminated packaging : Empty remaining contents. 
Dispose of as unused product.
Do not re-use empty containers. 
Transport information:
The shipping descriptions shown here are for bulk shipments only, and may not apply to
shipments in non-bulk packages (see regulatory definition).
Consult the appropriate domestic or international mode-specific and quantity-specific Dangerous
Goods Regulations for additional shipping description requirements (e.g., technical name or names,
etc.) Therefore, the information shown here, may not always agree with the bill of lading shipping
description for the material. 
Flashpoints for the material may vary slightly between the SDS and the bill of lading.

CAS Number    : 126-33-0 
EC Number    : 204-783-1
IUPAC name: 1λ6-Thiolane-1,1-dione

Synonyms:
MeSH Entry Terms:
Sulfolane

Depositor-Supplied Synonyms:
SULFOLANE

126-33-0

Tetramethylene sulfone

Tetrahydrothiophene 1,1-dioxide

Sulfolan

1,1-Dioxothiolan

Sulpholane

Sulphoxaline

Sulfalone

thiolane 1,1-dioxide

Dioxothiolan

Thiophene, tetrahydro-, 1,1-dioxide

Thiophan sulfone

Bondelane A

Bondolane A

Thiophane dioxide

Thiacyclopentane dioxide

Cyclotetramethylene sulfone

Tetrahydrothiophene dioxide

Thiolane-1,1-dioxide

Dihydrobutadiene sulfone

Cyclic tetramethylene sulfone

1,1-Dioxidetetrahydrothiophene

Dihydrobutadiene sulphone

1,1-Dioxidetetrahydrothiofuran

Tetrahydrothiophene 1-dioxide

Thiocyclopentane-1,1-dioxide

2,3,4,5-Tetrahydrothiophene-1,1-dioxide

1-Thiolane-1,1-dione

UNII-Y5L06AH4G5

NSC 46443

Tetrahydrothiofen-1,1-dioxid

MFCD00005484

Y5L06AH4G5

DTXSID3027037

CHEBI:74794

Bondelane A; Bondolane A; Cyclic tetramethylene sulfone; Cyclotetramethylene sulfone; NSC 46443

CCRIS 2310

HSDB 122

EINECS 204-783-1

Tetrahydrothiofen-1,1-dioxid [Czech]

1??-thiolane-1,1-dione

BRN 0107765

sulpholan

AI3-09541

tetramethylene sufone

tetramethylenesulphone

Sulfolane, 99%

tetramethylene-sulfone

tetramethylene sulphone

tetramethylene-sulphone

TETRAHYDROTHIOPHENE-1,1-DIOXIDE

CYCLOBUTYLSULFONE

Acetylthiocholinechloride

Thiophane 1,1-dioxide

WLN: T5SWTJ

DSSTox_CID_7037

EC 204-783-1

DSSTox_RID_78286

DSSTox_GSID_27037

SCHEMBL14301

5-17-01-00039 (Beilstein Handbook Reference)

Sulfolane, analytical standard

tetrahydrothiophene1,1-dioxide

Tetrahydothiophene-1,1-dioxide

tetrahydrothiophen-1,1-dioxide

tetrahydrothiophene-S,S-dioxide

1,1-Dioxide tetrahydrothiofuran

CHEMBL3186899

(CH2)4SO2

Sulfolane, redistilled from glass

tetra-hydrothiophene-1,1-dioxide

tetrahydro-thiophene-1,1-dioxide

Tetrahydrothiophene, 1,1-dioxide

AMY33385

NSC46443

ZINC3860777

Thiophene, 1,1-dioxide-tetrahydro-

Tox21_200628

NSC-46443

STL268898

AKOS002676003

AKOS015955444

Residual Solvent Class 2 - Sulfolane

Sulfolane, purum, >=98.0% (GC)

MCULE-3506686856

2,4,5-Tetrahydrothiophene-1,1-dioxide

NCGC00248771-01

NCGC00258182-01

CAS-126-33-0

PS-11978

R591

DB-038059

CS-0020029

FT-0689267

T0115

EN300-18394

D78046

Q416239

W-108395

F1294-0027

QXB