1562-00-1

Basic information

• Product Name: Sodium isethionate
• Synonyms: sodium2-hydroxyethylsulfonate;sodiumbeta-hydroxyethanesulfonate;Sodiumhydroxyethylsulfonate;ISETHIONIC ACID SODIUM SALT;HYDROXYETHYLSULFONIC ACID SODIUM SALT;2-HYDROXYETHANESULFONIC ACID;2-HYDROXYETHANESULFONIC ACID SODIUM SALT;SODIUM 2-HYDROXYETHANESULFONATE
• CAS NO: 1562-00-1
• Molecular Formula: C₂H₅O₄S*Na
• Molecular Weight: 148.11
• EINECS: 216-343-6
• Mol File: 1562-00-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 191-194 °C(lit.)
• Appearance: White/Fine Powder
• Density: 1.625 g/cm³
• Storage Temp.: Store below +30°C.
• Solubility: H2O: 0.1 g/mL, clear, colorless
• Water Solubility: SOLUBLE
• Stability: Stable. Hygroscopic. Incompatible with strong oxidizing agents, strong acids.
• BRN: 3633992
• CAS DataBase Reference: Sodium isethionate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium isethionate(1562-00-1)
• EPA Substance Registry System: Sodium isethionate(1562-00-1)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 24/25-36-22
• WGK Germany: 1
• RTECS: KI7700000
• TSCA: Yes
• Hazardous Substances Data: 1562-00-1(Hazardous Substances Data)

Usage

Chemical Properties

Sodium isethionate is a colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid. It is an organic salt and an important intermediate for pharmaceuticals, cosmetics and daily chemicals.

Uses

Isethionic acid sodium salt is an amphoteric detergent used in detergent bar soaps. It makes a dense lather in addition to the lather made by the soap. It is mild on the skin, and non-drying. It works equally well in soft or hard water. It is also an anti-static agent in shampoos.

Preparation

Sodium isethionate is synthesized by the condensation reaction of sodium bisulfite and ethylene oxide.

Application

Sodium Isethionate works as an amphoteric detergent and can also be used as an intermediate in preparing surfactants derived from fatty acid sulfoalkyl esters (acyloxy ethane sulfonate). Sodium Isethionate increases the formulation's stability, improves the detergency in hard water, and is smooth to the skin. It is used in cleaning/washing agents, disinfectants, cosmetics, surface-active agents, shampoos, and bubble baths.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)/p-1

Synthetic route

oxirane (75-21-8) → sodium 2-hydroxyethanesulfonate (1562-00-1)

Conditions	Yield
With sodium hydrogen sulfate at 40℃; for 0.25h; Temperature; Large scale;	99.5%
With water; sodium hydrogensulfite
With sodium metabisulfite

2-chloro-ethanol (107-07-3) → sodium 2-hydroxyethanesulfonate (1562-00-1)

Conditions	Yield
With copper; sodium sulfite In ethanol; water for 22h; Reflux;	77.4%

2-hydroxyethane-1-sulfonyl chloride (78303-70-5) → sodium 2-hydroxyethanesulfinate (43166-41-2) + sodium 2-hydroxyethanesulfonate (1562-00-1)

Conditions	Yield
With sodium hydrogencarbonate; sodium sulfite In water at 25℃; for 2.5h;	A 51% B 20%

pyridine (110-86-1) + 2-hydroxyethane-1-sulfonyl chloride (78303-70-5) → pyridinebetaine B (24020-66-4) + sodium 2-hydroxyethanesulfonate (1562-00-1) + Na-salt of 2-chloroethane-1-sulfonic acid (15484-44-3) + C2H4(2)HO4S(1-)*Na(1+) (87323-96-4)

Conditions	Yield
With deuteriated sodium hydroxide In water-d2 at 25℃; for 0.5h; apparent pH 6; Further byproducts given. Yields of byproduct given;	A 57 % Spectr. B n/a C 7 % Spectr. D n/a

sodium thiocyanide (540-72-7) + 2-hydroxyethane-1-sulfonyl chloride (78303-70-5) → sodium 2-hydroxyethanesulfonate (1562-00-1) + sodium thiocyanatoethanesulfonate (124739-85-1)

Conditions	Yield
With sodium perchlorate In acetonitrile at 25℃; Rate constant; Mechanism; Product distribution; pH 3.0;

2-hydroxyethane-1-sulfonyl chloride (78303-70-5) → sodium 2-hydroxyethanesulfonate (1562-00-1) + sodium vinylsulfonate (3039-83-6) + Na-salt of 2-chloroethane-1-sulfonic acid (15484-44-3)

Conditions	Yield
With sodium hydroxide; potassium chloride at 25℃; pH 4;	A 52 % Spectr. B n/a C 48 % Spectr.

2-hydroxyethane-1-sulfonyl chloride (78303-70-5) → sodium 2-hydroxyethanesulfonate (1562-00-1) + Na-salt of 2-chloroethane-1-sulfonic acid (15484-44-3)

Conditions	Yield
With sodium hydroxide; potassium chloride In 1,2-dimethoxyethane at 25℃; for 1.5h; Product distribution; var. pH; KCl added in var. conc.;	A 90 % Spectr. B 3 % Spectr.
With perchloric acid; sodium chloride In acetonitrile at 25℃; Rate constant; Mechanism; Product distribution; var. pH, added salts, time; deuterium labelling experiments;
With sodium hydroxide In 1,2-dimethoxyethane at 25℃; for 1.5h; pH 4;	A 90 % Spectr. B 3 % Spectr.

oxirane (75-21-8) + sodium hydrogensulfite → sodium 2-hydroxyethanesulfonate (1562-00-1)

Conditions	Yield
In not given in tube autoclave, below 50°C;
In not given for a while, 100°C, in closed tube;

Tau (107-35-7) → sodium 2-hydroxyethanesulfonate (1562-00-1)

Conditions	Yield
With oxirane at 78℃; Temperature;

2-sulfooxy-ethanesulfonic acid (461-42-7) → sodium 2-hydroxyethanesulfonate (1562-00-1)

Conditions	Yield
Stage #1: 2-sulfooxy-ethanesulfonic acid With water for 3h; Reflux; Stage #2: With sodium sulfate; calcium hydroxide In water pH=8 - 9;

2-hydroxyethanesulfonic acid (107-36-8) → sodium 2-hydroxyethanesulfonate (1562-00-1)

Conditions	Yield
With sulfuric acid; sodium sulfate; calcium hydroxide pH=8-9;

2-hydroxyethanesulfonic acid (107-36-8) + sodium taurinate (7347-25-3) → Tau (107-35-7) + sodium 2-hydroxyethanesulfonate (1562-00-1)

Conditions	Yield
In water at 20℃; pH=5.5; pH-value;

sodium 2-hydroxyethanesulfonate (1562-00-1) + 3,5-dinitrobenoyl chloride (99-33-2) → sodium 2-(3,5-dinitrobenzoyloxy)ethanesulfonate (117264-60-5)

Conditions	Yield
In neat (no solvent) for 0.0833333h; Heating;	97%

Octanoic acid (124-07-2) + sodium 2-hydroxyethanesulfonate (1562-00-1) + methylamine (74-89-5) → N-octanoyl-N-methyl taurine sodium

Conditions	Yield
at 150℃; for 4h;	95.6%

sodium 2-hydroxyethanesulfonate (1562-00-1) → Tau (107-35-7)

Conditions	Yield
With C22H24OP(1+)*CH3O3S(1-); ammonia; copper(l) chloride at 160℃; under 73507.4 Torr; for 0.5h; Reagent/catalyst; Temperature; Pressure;	95%
Stage #1: sodium 2-hydroxyethanesulfonate pH=12.5; Stage #2: With ammonia In water at 250℃; under 135014 Torr; for 2h; Autoclave;	91%
With ammonium hydroxide; sodium hydroxide at 250℃; for 2h; Reagent/catalyst; Temperature; Autoclave;	78.4%

sodium 2-hydroxyethanesulfonate (1562-00-1) → sodium taurinate (7347-25-3)

Conditions	Yield
With lithium bismuthate; ammonia; copper(l) chloride In water at 120℃; under 38253.8 Torr; for 0.5h; Reagent/catalyst; Temperature; Pressure;	95%
With ammonium hydroxide at 255℃; under 31128.1 Torr; for 1.5h; Pressure; Temperature;	39.16%
With ammonia at 250℃; for 2h; Autoclave;

1-(2-hydroxyethyl)piperazine (103-76-4) + sodium 2-hydroxyethanesulfonate (1562-00-1) → 4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid sodium salt (75277-39-3)

Conditions	Yield
sodium hydroxide at 204℃; under 4793.91 Torr; for 2.25h; Product distribution / selectivity; Autoclave;	94.6%
sodium hydroxide In water at 140 - 200℃; under 1587.51 - 5414.51 Torr; for 2 - 72h; Product distribution / selectivity; Autoclave;	6%

lauric acid (143-07-7) + sodium 2-hydroxyethanesulfonate (1562-00-1) + methylamine (74-89-5) → sodium N-lauroyl N-methyl taurate (4337-75-1)

Conditions	Yield
at 260℃; for 2h;	92%

sodium 2-hydroxyethanesulfonate (1562-00-1) → 2-hydroxyethanesulfonic acid (107-36-8)

Conditions	Yield
With hydrogenchloride In isopropyl alcohol at 20 - 50℃;	91.1%
With hydrogenchloride In isopropyl alcohol at 20 - 50℃;	91.1%
With resin In water at 20℃; for 96h;

sodium 2-hydroxyethanesulfonate (1562-00-1) → sodium 2-(acetyloxy)ethanesulfonate (52663-46-4)

Conditions	Yield
In acetic anhydride	91%

sodium 2-hydroxyethanesulfonate (1562-00-1) + acetic anhydride (108-24-7) → sodium 2-(acetyloxy)ethanesulfonate (52663-46-4)

Conditions	Yield
for 5h; Reflux;	91%

C24H22ClO3P + sodium 2-hydroxyethanesulfonate (1562-00-1) → C26H26O7PS(1-)*Na(1+)

Conditions	Yield
In dimethyl sulfoxide at 90℃; for 24h;	91%

cocinic acid + sodium 2-hydroxyethanesulfonate (1562-00-1) + methylamine (74-89-5) → C22H27N2O7S(1-)*Na(1+)

Conditions	Yield
at 210℃; for 4h; Temperature;	90.5%

sodium 2-hydroxyethanesulfonate (1562-00-1) → 2-Chloroethanesulfonyl chloride (1622-32-8)

Conditions	Yield
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20 - 60℃;	90%
With thionyl chloride In N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux;	64%
With phosphorus pentachloride

sodium 2-hydroxyethanesulfonate (1562-00-1) + (+/-)-2-(4-isobutylphenyl)propanoyl chloride (71381-91-4, 114978-05-1, 115588-20-0, 34715-60-1) → 2-[2-(4-isobutylphenyl)propionoyloxy]ethanesulfonic acid sodium salt (126962-22-9)

Conditions	Yield
With pyridine at 130℃; for 4h; Inert atmosphere;	86.7%

1-(2-hydroxyethyl)piperazine (103-76-4) + sodium 2-hydroxyethanesulfonate (1562-00-1) → N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid (7365-45-9)

Conditions	Yield
Stage #1: 1-(2-hydroxyethyl)piperazine; sodium 2-hydroxyethanesulfonate In methanol at 50℃; for 5.5h; Stage #2: With 5percent by weight of raffinate In water Solvent; Temperature;	85.6%

sodium 2-hydroxyethanesulfonate (1562-00-1) + benzyl alcohol (100-51-6) → sodium 2-benzylether ethanesulfonate

Conditions	Yield
With sodium hydroxide at 180 - 200℃; for 3h; Temperature;	78.6%

sodium 2-hydroxyethanesulfonate (1562-00-1) + n-tetradecanoic acid (544-63-8) + methylamine (74-89-5) → sodium 2-[methyl(1-oxotetradecyl)amino]ethanesulfonate (18469-44-8)

Conditions	Yield
at 280℃; for 6h;	78%

sodium 2-hydroxyethanesulfonate (1562-00-1) + (S)-naproxenoyl chloride (51091-84-0) → (S)-2-[2-(6-Methoxynaphthyl-2-yl)propionoyloxy]ethanesulfonic acid sodium salt (1268343-92-5)

Conditions	Yield
With pyridine at 130℃; for 4h; Inert atmosphere;	72.2%

sodium 2-hydroxyethanesulfonate (1562-00-1) → disodium 2-oxidoethane-1-sulfonate (1562-00-1, 115077-18-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 120h; Heating;	58.3%

sodium 2-hydroxyethanesulfonate (1562-00-1) + phenylacetyl chloride (103-80-0) → 2-(phenylacetyloxy)ethanesulfonic acid sodium salt

Conditions	Yield
With pyridine at 130℃; for 4h; Inert atmosphere;	54.6%
at 130 - 140℃;

Hexanoic acid (Z)-8-chlorocarbonyl-1,7-dimethyl-oct-7-enyl ester + sodium 2-hydroxyethanesulfonate (1562-00-1) → Sodium; 2-((Z)-9-hexanoyloxy-3-methyl-dec-2-enoyloxy)-ethanesulfonate

Conditions	Yield
In toluene Heating;	49%

Tricosanoic acid (Z)-8-chlorocarbonyl-1,7-dimethyl-oct-7-enyl ester + sodium 2-hydroxyethanesulfonate (1562-00-1) → Sodium; 2-((Z)-3-methyl-9-tricosanoyloxy-dec-2-enoyloxy)-ethanesulfonate

Conditions	Yield
In toluene Heating;	47%

morpholine (110-91-8) + sodium 2-hydroxyethanesulfonate (1562-00-1) → 2-(N-morpholino)ethanesulfonic acid sodium salt (71119-23-8)

Conditions	Yield
sodium hydroxide In water at 200℃; under 3345.86 - 8517.48 Torr; for 2 - 4h; Product distribution / selectivity; Autoclave;	44.2%

(5Z,9Z)-Tetracosa-5,9-dienoic acid (Z)-8-chlorocarbonyl-1,7-dimethyl-oct-7-enyl ester + sodium 2-hydroxyethanesulfonate (1562-00-1) → Sodium; 2-[(Z)-3-methyl-9-((5Z,9Z)-tetracosa-5,9-dienoyloxy)-dec-2-enoyloxy]-ethanesulfonate

Conditions	Yield
In toluene Heating;	43%

(Z)-Docos-15-enoic acid (Z)-8-chlorocarbonyl-1,7-dimethyl-oct-7-enyl ester + sodium 2-hydroxyethanesulfonate (1562-00-1) → Sodium; 2-[(Z)-9-((Z)-docos-15-enoyloxy)-3-methyl-dec-2-enoyloxy]-ethanesulfonate

Conditions	Yield
In toluene Heating;	29%

sodium 2-hydroxyethanesulfonate (1562-00-1) + 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride (20357-37-3) → 2-{2-[1-((4-chlorobenzoyl)-2-methyl-5-methoxyl-1H-indoyl-3-yl)]acetoxy}ethanesulfonic acid sodium salt

Conditions	Yield
With pyridine at 50 - 60℃; for 24h; Inert atmosphere;	22.1%

Cholesteryl chloroformate (7144-08-3) + sodium 2-hydroxyethanesulfonate (1562-00-1) → Sodium; 2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-ethanesulfonate

Conditions	Yield
With pyridine for 20h; Ambient temperature;	21%

sodium 2-hydroxyethanesulfonate (1562-00-1) + benzyl chloride (100-44-7) → C9H11O4S(1-)*K(1+)

Conditions	Yield
Stage #1: sodium 2-hydroxyethanesulfonate; benzyl chloride With triethylamine at 70 - 130℃; for 1h; Stage #2: With potassium chloride at 35 - 40℃;	19%

Upstream product

• 107-35-7 Tau 
• 7757-83-7 sodium sulfite 
• 107-07-3 2-chloro-ethanol 
• 107-36-8 2-hydroxyethanesulfonic acid 
• 7347-25-3 sodium taurinate 
• 461-42-7 2-sulfooxy-ethanesulfonic acid 
• 75-21-8 oxirane 
• 78303-70-5 2-hydroxyethane-1-sulfonyl chloride 
• 540-72-7 sodium thiocyanide 
• 110-86-1 pyridine 

Downstream Products

• 116956-59-3 4-oxo-4-phenyl-butane-1-sulfonic acid ; sodium-salt 
• 56022-49-2 2-sulfoethyl laurate 
• 1562-00-1 disodium 2-oxidoethane-1-sulfonate 
• 71119-23-8 2-(N-morpholino)ethanesulfonic acid sodium salt 
• 70523-58-9 Sodium sulfoethyl 4-(hexadecylamino)benzoate 
• 114959-93-2 2-chloroacetoxy-ethanesulfonic acid ; sodium-salt 
• 107-35-7 Tau 
• 1184-84-5 ethenesulfonic acid 
• 7347-25-3 sodium taurinate 
• 7365-45-9 N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid 

Relevant articles and documents

Method for preparing taurine

The invention provides a method for preparing taurine. The method comprises the following steps: carrying out an addition reaction on ethylene oxide and sodium hydrogen sulfite in the presence of a heterogeneous catalyst so as to obtain sodium hydroxyethyl sulfonate at high selectivity; carrying out an ammonolysis reaction on the synthesized sodium hydroxyethyl sulfonate under catalysis of a homogeneous catalyst; and neutralizing, crystallizing, separating and the like, thereby obtaining the finished taurine. Compared with the traditional production process, the process disclosed by the invention has the advantages that by-products in the addition reaction process can be obviously reduced, the temperature and pressure of the ammonolysis reaction are reduced, the reaction time is shortened,and industrial production is easily realized.

High-yield circular production method of taurine

The high-yield circular production method of taurine includes the following steps: S1, ethylene oxide reacts with sodium bisulfite solution to generate sodium hydroxyethyl sulfonate; S2, sodium hydroxyethyl sulfonate obtained in S1 is subjected to ammonolysis reaction in ammonia, and ammonia gas is recycled through flash evaporation upon completion of the reaction; S3, a reaction solution obtained after flash evaporation in S2 is sent to pass through an acidic cation exchange resin column, a material liquid containing taurine is collected, the inactivated resin column is subjected to regeneration with sulfur dioxide or carbon dioxide aqueous solution, and an eluent acquired during regeneration can be recycled directly or recycled after treated by sulfur dioxide; S4, the material liquid collected in S3 is subjected to post treatment to acquire taurine.

Process for the production of taurine from ethanol

The present invention discloses a process for the preparation of taurine from ethionic acid and ethanol by way of ethanol-derived ethionic acid by the ammonolysis of ethionic acid and by the ammonolysis of sodium isethionate and sodium vinyl sulfonate, key intermediates prepared from ethionic acid.