593-29-3

Basic information

• Product Name: Potassium stearate
• Synonyms: STEARIC ACID, POTASSIUM SALT;OCTADECONOIC ACID, POTASSIUM SALT;OCTADECANOIC ACID, POTASSIUM SALT;POTASSIUM STEARATE;POTASSIUM OCTADECANOATE;Potassium stearate,95%;potassiumn-octadecanoate;potassiumstearate,pure
• CAS NO: 593-29-3
• Molecular Formula: C₁₈H₃₅O₂*K
• Molecular Weight: 322.57
• EINECS: 209-786-1
• Product Categories: emulsifier;Food additives
• Mol File: 593-29-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 359.4 °C at 760 mmHg
• Flash Point: 162.4 °C
• Appearance: white powder
• Density: 1.12 g/cm3
• Vapor Pressure: 8.58E-06mmHg at 25°C
• Water Solubility: insoluble
• CAS DataBase Reference: Potassium stearate(CAS DataBase Reference)
• NIST Chemistry Reference: Potassium stearate(593-29-3)
• EPA Substance Registry System: Potassium stearate(593-29-3)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 593-29-3(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 593-29-3 differently. You can refer to the following data:
1. In the manufacture of textile softeners.
2. potassium stearate is a cleansing and emulsifying agent.
3. Potassium Stearate is the potassium salt of stearic acid. it is used as a binder, emulsifier, anticaking agent, and as a plasticizer in chewing gum base.

Safety Profile

When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C18H36O2.K/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;/h2-17H2,1H3,(H,19,20);/q;+1/p-1

Synthetic route

Methyl stearate (112-61-8) + aqueous KOH → potassium stearate (593-29-3)

Conditions	Yield
Trennung von Stearinsaeure durch Behandeln des Saeure-Ester-Gemisches in Aethylenchlorid;

cis-Octadecenoic acid (112-80-1) + hydrazine hydrate (7803-57-8) → stearic acid hydrazide (4130-54-5) + potassium stearate (593-29-3)

Conditions	Yield
das Kaliumsalz;

methanesulfonic acid (75-75-2) + n-butyl methanesulfonate (1912-32-9) + n-butyl stearate (123-95-5) + stearic acid (57-11-4) → potassium mesylate (2386-56-3) + potassium stearate (593-29-3)

Conditions	Yield
With potassium hydroxide; water In butan-1-ol at 50 - 175℃; for 0.666667 - 1h; Conversion of starting material;

stearic acid (57-11-4) → potassium stearate (593-29-3)

Conditions	Yield
With potassium hydroxide In water at 20℃; for 0.5h;
With potassium hydroxide at 80℃; pH=10.4;

Methyl stearate (112-61-8) → potassium stearate (593-29-3)

Conditions	Yield
With potassium hydroxide In methanol at 60 - 100℃; under 30.003 Torr; for 0.166667h; Microwave irradiation;

potassium stearate (593-29-3) + 1-Bromooctadecane (112-89-0) → octadecanoic acid, octadecyl ester (2778-96-3)

Conditions	Yield
With Aliquat 336 for 0.0166667h; Irradiation;	98%

potassium stearate (593-29-3) + stearic acid (57-11-4) → stearic anhydride (638-08-4)

Conditions	Yield
Stage #1: stearic acid With trichloroisocyanuric acid; triphenylphosphine In dichloromethane at 0 - 20℃; Stage #2: potassium stearate In dichloromethane at 20℃; for 1.25h;	95%

potassium stearate (593-29-3) + 4-chloromethyl-2-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-[1,3,2]dioxaphospholane 2-oxide (340732-61-8) → C27H51ClO8P(1-)*K(1+)

Conditions	Yield
at 130℃; for 4h;	88%

europium(III) nitrate hexahydrate + water (7732-18-5) + potassium stearate (593-29-3) → europium(III)(n-C17H35CO2)3*H2O

Conditions	Yield
In ethanol; water potassium n-alkanoate dissolved in a mixture of deionized water and ethanol (1:1 v/v) and added dropwise to a stirred soln. of Eu(NO3)3*6H2O in water; white precipitate formed; stirred at room temp. for 3 h; precipitate filtered, and washed repeatedly with aq. ethanol (1:1 v/v) and hot acetone; dried at room temp. for 24 h; elem. anal.;	85%

2-morpholino-2-oxo-1,3,2λ5-dioxaphosphorinane (53179-86-5) + potassium stearate (593-29-3) → potassium 2-stearoyloxypropyl morpholidophosphate

Conditions	Yield
at 130℃; for 3.5h;	77%

potassium stearate (593-29-3) + 2-oxo-2-(1,2-distearoyl-3-rac-glycero)-5-benzyloxy-1,3,2-dioxaphosphorinane (79635-18-0) → potassium (1-stearoyl-2-O-benzyl-rac-glycero-3)-(1,2-distearoyl-rac-glycero-3)phosphate (79635-19-1)

Conditions	Yield
at 125℃; for 3h;	76.1%

potassium stearate (593-29-3) + 2-morpholino-2-oxo-1,3,2λ5-dioxaphospholane (7114-70-7) → potassium 2-stearoyloxyethyl morpholidophosphate

Conditions	Yield
at 125℃; for 1.5h;	75%

2-oxo-2-(2,2,2-trichloroethoxy)-1,3,2λ5-dioxaphosphorinane (53236-59-2) + potassium stearate (593-29-3) → potassium 2-stearoyloxypropyl (2,2,2-trichloroethyl) phosphate

Conditions	Yield
at 120℃; for 2h;	72%

potassium stearate (593-29-3) + 2-oxo-2-(1,2-distearoyl-rac-glycero)-1,3,2-oxathiaphosphorinane (120489-88-5) → 1,2-distearoyl-rac-glycero-3-thio-γ-stearoylpropyl phosphate, potassium salt

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 3h;	71%

dichlorobis(acetylacetonato-O,O')titanium(IV) + potassium stearate (593-29-3) → bis(acetylacetonato)distearato titanate(IV)

Conditions	Yield
In methanol byproducts: KCl; Ti(acac)2Cl2 soln. added to K-stearate soln., stirred, refluxed (3h); cooled to room temp., KCl removed by filtration, mother liquor concentrated, cooled, ppt. filtered, washed with dry ether, dried (in vac.); elem. anal.;	70%

potassium stearate (593-29-3) + allyl bromide (106-95-6) → allyl stearate (6289-31-2)

Conditions	Yield
tetrabutylammomium bromide In dichloromethane at 20 - 22℃; for 50h;	66%

potassium stearate (593-29-3) + 4-chloromethyl-2-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-[1,3,2]dioxaphospholane 2-sulfide → C27H51ClO7PS(1-)*K(1+)

Conditions	Yield
at 90℃; for 12h;	62%

potassium stearate (593-29-3) + 2,2-di(2-thioxo-1,3,2λ5-dioxaphosphorinan-2-yloxymethyl)trimethylene distearate (152015-83-3) → dipotassium O,O'-bis(3-stearoyloxypropyl)-O,O'-(2,2-distearoyloxymethyltrimethylene) bisthiophosphate

Conditions	Yield
at 120℃; for 12h;	60%

potassium stearate (593-29-3) + 2-oxo-2-(1,2-distearoyl-rac-glycero)-1,3,2-oxaselenaphosphorinane (120489-87-4) → 1,2-distearoyl-rac-glycero-3-seleno-γ-stearoylpropyl phosphate, potassium salt

Conditions	Yield
In dimethyl sulfoxide at 85℃; for 3h;	55%

2-[2,2-bis(stearoyloxymethyl)pentyloxy]-1,3,2λ5-dioxaphosphinane 2-selenide (888227-05-2) + potassium stearate (593-29-3) → potassium O-[2,2-bis(stearoyloxymethyl)pentyl]-O-[3-(stearoyloxy)propyl] selenophosphate

Conditions	Yield
at 120℃; for 12h;	52%

2-[2,2-bis(stearoyloxymethyl)pentyloxy]-1,3,2λ5-dioxaphosphinane 2-sulfide (888227-04-1) + potassium stearate (593-29-3) → potassium O-[2,2-bis(stearoyloxymethyl)pentyl]-O-[3-(stearoyloxy)propyl] thiophosphate

Conditions	Yield
at 120℃; for 12h;	51.6%

rasagiline-N-chloromethyl formate + potassium stearate (593-29-3) → methyl ((rasagiline-N-formyl)oxy)stearate

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 65℃; Inert atmosphere;	51.55%

2-thio-2-[2,2-di(stearoyloxymethyl)hexyl-1-oxy]-1,3,2-dioxaphospholane (883149-10-8) + potassium stearate (593-29-3) → C64H124O9PS(1-)*K(1+)

Conditions	Yield
at 120℃; for 12h;	46%

sucrose (27641-21-0) + potassium stearate (593-29-3) → sucrose stearate

Conditions	Yield
With potassium hydroxide In water at 130℃; under 30.003 Torr; for 3h; Temperature; Time; Microwave irradiation;	45.1%

2-seleno-2-[2,2-di(stearoyloxymethyl)hexyl-1-oxy]-1,3,2-dioxaphospholane (883149-11-9) + potassium stearate (593-29-3) → C64H124O9PSe(1-)*K(1+)

Conditions	Yield
at 120℃; for 12h;	43%

1,3,2-dioxaphosphinan-2-oxide (16352-21-9) + potassium stearate (593-29-3) → potassium 3-stearoyloxypropyl phosphonate

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 4h;	27%

1-bromo-2-propanol (19686-73-8) + potassium stearate (593-29-3) → stearic acid-(2-hydroxy-propyl ester) (142-75-6, 20325-59-1) + propylene glycol distearate (6182-11-2, 20243-23-6)

Conditions	Yield
at 130℃;

butyl chloroacetate (590-02-3) + potassium stearate (593-29-3) → stearoyloxy-acetic acid butyl ester

Conditions	Yield
With xylene at 170℃;

ethanol (64-17-5) + potassium stearate (593-29-3) → stearic acid ethyl ester (111-61-5)

Conditions	Yield
With acid Electrolysis;

Methyl 2-bromopropionate (5445-17-0) + potassium stearate (593-29-3) → 2-stearoyloxy-propionic acid methyl ester

Conditions	Yield
With xylene at 170℃;

2-bromopropanol (598-18-5) + potassium stearate (593-29-3) → 1,2-propylene glycol stearate (3539-36-4)

Conditions	Yield
at 130℃;

3-iodo-propane-1,2-diol (554-10-9) + potassium stearate (593-29-3) → bis-(2-hydroxy-3-stearoyloxy-propyl)-ether (107208-72-0)

Conditions	Yield
at 100℃;

1,3-Dichloro-2-propanol (96-23-1) + potassium stearate (593-29-3) → 1,3-distearoylglycerol (504-40-5)

n-butyl α-chloropropionate (54819-86-2) + potassium stearate (593-29-3) → 2-stearoyloxy-propionic acid butyl ester

Conditions	Yield
With xylene at 170℃;

1-bromo-3-palmitoyloxy-acetone (412019-89-7) + potassium stearate (593-29-3) → 1-palmitoyloxy-3-stearoyloxy-acetone (860712-34-1)

Conditions	Yield
With ethanol

Upstream product

• 112-61-8 Methyl stearate 
• 112-80-1 cis-Octadecenoic acid 
• 7803-57-8 hydrazine hydrate 
• 57-11-4 stearic acid 
• 75-75-2 methanesulfonic acid 
• 1912-32-9 n-butyl methanesulfonate 
• 123-95-5 n-butyl stearate 

Downstream Products

• 142-75-6 stearic acid-(2-hydroxy-propyl ester) 
• 6182-11-2 propylene glycol distearate 
• 504-40-5 1,3-distearoylglycerol 
• 22610-63-5 octadecanoic acid 2,3-dihydroxypropyl ester 
• 111-60-4 ethylene glycol monostearate 
• 10108-23-3 octadecanoic acid, 3-hydroxypropyl ester 
• 17367-44-1 1,3-propanediol distearate 
• 111-61-5 stearic acid ethyl ester 
• 51063-97-9 DL-α,β-distearin 
• 30557-01-8 3-bromo-2-hydroxypropyl stearate 
• 7460-84-6 glycidyl octadecanoyl ether 
• 33418-10-9 1-bromomethyl-2-hydroxyethyl stearate 
• 2778-96-3 octadecanoic acid, octadecyl ester 
• 56554-26-8 2-myristoyloxy-1-palmitoyloxy-3-stearoyloxy-propane 

Relevant articles and documents

Fatty acid potassium had beneficial bactericidal effects and removed Staphylococcus aureus biofilms while exhibiting reduced cytotoxicity towards mouse fibroblasts and human keratinocytes

Wounds frequently become infected or contaminated with bacteria. Potassium oleate (C18:1K), a type of fatty acid potassium, caused >4 log colony-forming unit (CFU)/mL reductions in the numbers of Staphylococcus aureus and Escherichia coli within 10 min and a >2 log CFU/mL reduction in the number of Clostridium difficile within 1 min. C18:1K (proportion removed: 90.3%) was significantly more effective at removing Staphylococcus aureus biofilms than the synthetic surfactant detergents sodium lauryl ether sulfate (SLES) (74.8%, p 0.01) and sodium lauryl sulfate (SLS) (78.0%, p 0.05). In the WST (water-soluble tetrazolium) assay, mouse fibroblasts (BALB/3T3 clone A31) in C18:1K (relative viability vs. control: 102.8%) demonstrated a significantly higher viability than those in SLES (30.1%) or SLS (18.1%, p 0.05). In a lactate dehydrogenase (LDH) leakage assay, C18:1K (relative leakage vs. control: 108.9%) was found to be associated with a significantly lower LDH leakage from mouse fibroblasts than SLES or SLS (720.6% and 523.4%, respectively; p 0.05). Potassium oleate demonstrated bactericidal effects against various species including Staphylococcus aureus, Escherichia coli, Bacillus cereus, and Clostridium difficile; removed significantly greater amounts of Staphylococcus aureus biofilm material than SLES and SLS; and maintained fibroblast viability; therefore, it might be useful for wound cleaning and peri-wound skin.

Facile and direct synthesis of symmetrical acid anhydrides using a newly prepared powerful and efficient mixed reagent

An efficient mixed reagent for direct synthesis of symmetrical carboxylic anhydrides from carboxylic acids has been prepared. Carboxylic acids are converted to anhydrides using triphenylphosphine/ trichloroisocyanuric acid under mild reaction conditions at room temperature. Short reaction time, excellent yields of products, low cost, availability of reagents, simple experimental procedure, and easy work-up of the products are the main advantages of the presented method.