PRODUCTS

SODIUM 2-HYDROXYETHYL SULFONATE (SODIUM ISETHIONATE)

DESCRIPTION:

Sodium 2-hydroxyethyl sulfonate (also: sodium isethionate) is the sodium salt of 2-hydroxyethane sulfonic acid (isethionic acid), it is used as a hydrophilic head group in washing-active surfactants, known as isethionates (acyloxyethanesulfonates) due to its strong polarity and resistance to multivalent ions.
It is being studied as a high production volume chemical in the "High Production Volume (HPV) Chemical Challenge Program" of the US Environmental Protection Ministry EPA.[1]

CAS Number 1562-00-1
EC Index Number: 216-343-6
Molecular Formula C2H6NaO4S+

SYNONYMS OF SODIUM 2-HYDROXYETHYL SULFONATE (SODIUM ISETHIONATE):
Sodium 2-hydroxyethyl sulfonate,sodium;2-hydroxyethanesulfonic acid,Sodium .beta.-hydroxyethanesulfonate,NSC124283,1562-00-1[RN],2-Hydroxyéthanesulfonate de sodium[French][ACD/IUPAC Name],2-Hydroxyethanesulfonic acid sodium salt,2-Hydroxyethanesulfonic acid, sodium salt,2-Hydroxyethanesulphonic acid, sodium salt,216-343-6[EINECS],3R36J71C17[UNII],Ethanesulfonic acid, 2-hydroxy-, monosodium salt,Ethanesulfonic acid, 2-hydroxy-, sodium salt,Ethanesulfonic acid, 2-hydroxy-, sodium salt (1:1)[ACD/Index Name],Isethionic acid sodium salt,MFCD00007534[MDL number],Natrium-2-hydroxyethansulfonat[German][ACD/IUPAC Name],Sodium 2-hydroxy-1-ethanesulfonate,SODIUM 2-HYDROXYETHANE-1-SULFONATE,Sodium 2-hydroxyethanesulfonate[ACD/IUPAC Name],Sodium 2-hydroxyethanesulphonate,Sodium 2-hydroxyethyl sulfonate[Wiki] ,Sodium isethionate,Sodium β-hydroxyethanesulfonate,WSQ2Q &&Na salt[WLN],SODIUM ISETHIONATE,1562-00-1,Sodium 2-hydroxyethanesulfonate,Isethionic acid sodium salt,2-Hydroxyethanesulfonic acid sodium salt,Sodium hydroxyethylsulfonate,Ethanesulfonic acid, 2-hydroxy-, monosodium salt,Sodium 2-hydroxyethylsulfonate,HSDB 5838,Sodium beta-hydroxyethanesulfonate,Sodium 1-hydroxy-2-ethanesulfonate,Sodium 2-hydroxy-1-ethanesulfonate,EINECS 216-343-6,MFCD00007534,NSC 124283,2-Hydroxyethanesulfonic acid, sodium salt,DTXSID7027413,UNII-3R36J71C17,Ethanesulfonic acid, 2-hydroxy-, sodium salt,3R36J71C17,Ethanesulfonic acid, 2-hydroxy-, sodium salt (1:1),DTXCID007413,ISETHIONATE, SODIUM SALT,SODIUM ISETHIONATE [HSDB],EC 216-343-6,NSC-124283,SODIUM 2-HYDROXYETHANESULFONIC ACID,Sodium 1-hydroxy-2-ethanesulfonate; Sodium 2-hydroxy-1-ethanesulfonate; Sodium 2-hydroxyethanesulfonate,sodium;2-hydroxyethanesulfonate,Sodium 2-hydroxyethanesulphonate,C2H5NaO4S,Isethionic acid, sodium salt,Isethionate, Sodium,2-Hydroxyethanesulfonic acid sodium salt (SHES),sodium hydroxyethyl sulfonate,Sodium 2hydroxyethylsulfonate,Sodium 2hydroxyethanesulfonate,SCHEMBL125497,Sodium 2hydroxyethyl sulfonate,Sodium 1hydroxy2ethanesulfonate,Sodium 2hydroxy1ethanesulfonate,CHEMBL172191,Sodium betahydroxyethanesulfonate,Sodium 2-Hydroxy-Ethanesulfonate,SODIUM ISETHIONATE [INCI],Isethionic acid sodium salt, 98%,HY-Y1173,Tox21_200227,AKOS015912506,2Hydroxyethanesulfonic acid sodium salt,NCGC00257781-01,CAS-1562-00-1,Ethanesulfonic acid, 2hydroxy, sodium salt,CS-0017163,H0241,NS00078178,Ethanesulfonic acid, 2hydroxy, monosodium salt,G74509,J-009283,Q1969744,F1905-7166

Isethionic acid (C2H6O4S) is a short chain alkane sulfonate containing hydroxy group, is a water soluble liquid used in the manufacture of mild, biodegradable and high foaming anionic surfactants which provides gentle cleansing and soft skin feel.; A colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid.

The Pseudomonas aeruginosa ssuEADCB gene cluster is required for the utilization of alkanesulfonates (such as isethionic acid) as sulfur sources, and is expressed under conditions of sulfate or cysteine starvation.

Isethionic acid sodium salt is an amphoteric detergent used in detergent bar soaps.
Sodium 2-hydroxyethyl Sulfonate (Sodium Isethionate) makes a dense lather in addition to the lather made by the soap.
Sodium 2-hydroxyethyl Sulfonate (Sodium Isethionate) is mild on the skin, and non-drying.

Sodium 2-hydroxyethyl Sulfonate (Sodium Isethionate) works equally well in soft or hard water.
Sodium 2-hydroxyethyl Sulfonate (Sodium Isethionate) is also an anti-static agent in shampoos.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio.
Some documentation and label information may refer to the legacy brand.

The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications of Sodium 2-hydroxyethyl Sulfonate (Sodium Isethionate):

Sodium 2-hydroxyethyl Sulfonate (Sodium Isethionate) works equally well in soft or hard water.
Sodium 2-hydroxyethyl Sulfonate (Sodium Isethionate) is also an anti-static agent in shampoos.

Solubility:
Soluble in water.

Sodium hydroxyethyl sulfonate is an organic salt and an important intermediate of pharmaceuticals, cosmetics and daily chemicals.
Its synthesis principle is the condensation reaction between sodium bisulfite and ethylene oxide to produce sodium hydroxyethyl sulfonate.

Production
Sodium 2-hydroxyethyl sulfonate is formed by the reaction of ethylene oxide with sodium hydrogen sulfite in aqueous solution:

To avoid contamination and suppress the formation of by-products (which are difficult to remove) the reaction must be performed under careful control of mass ratios and process conditions.[2]

Excess sulfite (SO32−) or bisulfite (HSO3−) lead to an unpleasant odor of the downstream product, higher levels of ethylene glycol or glycol ethers (formed by the hydrolysis and ethoxylation of ethylene oxide) give hygroscopic and greasy surfactants.

Concentrated ethylene glycol-containing sodium 2-hydroxyethyl sulfonate solutions can subsequently mostly be freed from ethylene glycol by continuous extraction with e.g. isopropanol (<0.5%).[3]

Therefore, in the continuous industrial process an aqueous sodium hydrogen sulfite solution is prepared in a first reactor by mixing a sodium hydroxide solution and sulfur dioxide.
In a second reactor the sodium hydrogen sulfite solution is mixed with a slight excess of ethylene oxide to obtain sodium 2-hydroxyethyl sulfonate in almost quantitative yields at elevated temperature and pressure with a precise control of pH.
The reaction has to take place under the exclusion of oxygen and under precise control of the stoichiometry of the reactants, the temperature, the pH and the throughput.

PROPERTIES OF SODIUM 2-HYDROXYETHYL SULFONATE (SODIUM ISETHIONATE):
Solid sodium 2-hydroxyethyl sulfonate is a colorless, free-flowing, non-hygroscopic solid, which dissolves readily in water and has good biodegradability.
Due to the method of synthesis samples often contain traces of sodium sulfite or sodium hydrogen sulfite causing aqueous solution to possesses a mildly alkaline pH of about 10.[4]

USES OF SODIUM 2-HYDROXYETHYL SULFONATE (SODIUM ISETHIONATE) :

The main use of sodium 2-hydroxyethyl sulfonate is the production of the isethionate class of surfactants.
These are readily foaming and particularly mild, making them suitable for cleaning sensitive skin and are therefore mainly used in baby soaps and shampoos.[5]

Because of its pronounced skin compatibility sodium 2-hydroxyethyl sulfonate is added to soaps and liquid skin cleansers with up to 15 parts by weight.
From sodium 2-hydroxyethyl sulfonate the so-called biological buffers such as HEPES, MES, PIPES etc. are easily accessible.[6]

The addition of 2-hydroxyethyl sulfonate to electroplating baths allows higher current densities and lower concentrations than the much more expensive methane sulphonic acid with improved appearance

CHEMICAL AND PHYSICAL PROPERTIES OF SODIUM 2-HYDROXYETHYL SULFONATE (SODIUM ISETHIONATE):

Molecular Weight
149.12 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Hydrogen Bond Donor Count
2
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count
4
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count
2
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass
148.98844912 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Monoisotopic Mass
148.98844912 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Topological Polar Surface Area
83Å²
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count
8
Computed by PubChem
Formal Charge
1
Computed by PubChem
Complexity
117
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count
0
Computed by PubChem
Defined Atom Stereocenter Count
0
Computed by PubChem
Undefined Atom Stereocenter Count
0
Computed by PubChem
Defined Bond Stereocenter Count
0
Computed by PubChem
Undefined Bond Stereocenter Count
0
Computed by PubChem
Covalently-Bonded Unit Count
2
Computed by PubChem
Compound Is Canonicalized
Yes
Molecular formula:C2H5NaO4S
Average mass:   148.108
Monoisotopic mass:   147.980624
ChemSpider ID:   14540
Formula: C₂H₅NaO₄S
MW: 148.11 g/mol
Melting Pt: 192…194 °C
Storage Temperature: Ambient
Quality Level
200
form
powder
potency
>2500 mg/kg LD50, oral (Rat)
pH
7.0-11.0 (20 °C, 20 g/L in H2O)
mp
192-194 °C
bulk density
800 kg/m3
storage temp.
2-30°C
InChI
1S/C2H6O4S.Na/c3-1-2-7(4,5)6;/h3H,1-2H2,(H,4,5,6);/q;+1/p-1
InChI key
LADXKQRVAFSPTR-UHFFFAOYSA-M
Melting Point 191°C to 194°C
Quantity 1000 g
Beilstein 3633992
Solubility Information Soluble in water.
Formula Weight 148.11
Percent Purity 98%
Chemical Name or Material Isethionic acid sodium salt
CAS 1562-00-1
Molecular Formula C2H5NaO4S
Molecular Weight (g/mol) 148.108
MDL Number MFCD00007534
InChI Key LADXKQRVAFSPTR-UHFFFAOYSA-MShow More
Synonym sodium 2-hydroxyethanesulfonate, sodium isethionate, isethionic acid sodium salt, 2-hydroxyethanesulfonic acid sodium salt, sodium hydroxyethylsulfonate, ethanesulfonic acid, 2-hydroxy-, monosodium salt, sodium 2-hydroxyethylsulfonate, sodium 2-hydroxyethanesulphonate, sodium beta-hydroxyethanesulfonate, sodium 1-hydroxy-2-ethanesulfonateShow More
PubChem CID 517063
IUPAC Name sodium;2-hydroxyethanesulfonate
SMILES C(CS(=O)(=O)[O-])O.[Na+]

SAFETY INFORMATION ABOUT SODIUM 2-HYDROXYETHYL SULFONATE (SODIUM ISETHIONATE):

First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:

If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.

In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.

If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.

Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas

Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.

Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.

Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.

Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.

Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.

Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials

Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.

Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.

Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.

Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.

If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.

Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.

Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product.