764-71-6

Basic information

• Product Name: POTASSIUM OCTOATE
• Synonyms: OCTANOIC ACID POTASSIUM SALT;POTASSIUM CAPRYLATE;POTASSIUM OCTOATE;POTASSIUM N-OCTANOATE;potassium octanoate;Caprylic acid potassium salt;Octanoic acid,potassiuM salt (1:1)
• CAS NO: 764-71-6
• Molecular Formula: C₈H₁₅O₂*K
• Molecular Weight: 182.3
• EINECS: 212-130-7
• Mol File: 764-71-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 239.3 °C at 760 mmHg
• Flash Point: 107.4 °C
• Appearance: /
• Vapor Pressure: 0.022mmHg at 25°C
• CAS DataBase Reference: POTASSIUM OCTOATE(CAS DataBase Reference)
• NIST Chemistry Reference: POTASSIUM OCTOATE(764-71-6)
• EPA Substance Registry System: POTASSIUM OCTOATE(764-71-6)

Safety Data

• Hazardous Substances Data: 764-71-6(Hazardous Substances Data)

Usage

General Description

POTASSIUM OCTOATE is a chemical compound with the formula K[CH(CH3)COO] and is known as a potassium salt of octanoic acid. It is a colorless to pale yellow liquid with a pungent odor, and is commonly used as a curing agent in the production of coatings, adhesives, and sealants. It is also used as a catalyst in various chemical reactions, particularly in the production of polyurethane foams and coatings. POTASSIUM OCTOATE is a highly reactive compound and must be handled with care, as it can cause irritation to the skin, eyes, and respiratory tract if not used properly.

InChI:InChI=1/C8H16O2.K/c1-2-3-4-5-6-7-8(9)10;/h2-7H2,1H3,(H,9,10);/q;+1/p-1

Synthetic route

octanol (111-87-5) → potassium octanoate (764-71-6)

Conditions	Yield
With C18H23IrN3(1+)*CF3O3S(1-); potassium hydroxide In toluene at 120℃; for 40h;	90%
With C27H29BrFIrN2O; potassium hydroxide In toluene for 15h; Inert atmosphere; Reflux;	75%

octanol (111-87-5) → 2-hexyldecan-1-ol (2425-77-6) + potassium octanoate (764-71-6)

Conditions	Yield
With C22H36IrNP(1+)*CF3O3S(1-); potassium hydroxide In toluene at 120℃; for 37h;	A 5 %Spectr. B 95 %Spectr.

Octanoic acid (124-07-2) → potassium octanoate (764-71-6)

Conditions	Yield
With potassium hydroxide at 80℃; pH=10.4;

sodium molybdate dihydrate (7631-95-0) + potassium octanoate (764-71-6) → di-μ-sulphido oxomolybdenum(V) n-heptyl carboxylate

Conditions	Yield
With sodium hydroxide; hydrogen sulfide; acetic acid In water pH=8-9; potassium salt was added to soln. of Na2MoO4*2H2O; H2S was bubbled slowly through soln. for 40 min; dropwise addn. of glacial acetic acid; filtered; washed (cold water); dried over P4O10 in N2; elem.anal.;	45%

tetrachloromethane (56-23-5) + bromine (7726-95-6) + potassium octanoate (764-71-6) → 1-Bromoheptane (629-04-9)

bromine (7726-95-6) + potassium octanoate (764-71-6) + CS2 → 1-Bromoheptane (629-04-9)

chloroformic acid ethyl ester (541-41-3) + potassium octanoate (764-71-6) → (ethoxycarbonyl)octanoate (71478-41-6)

Conditions	Yield
In dichloromethane at 20℃;

potassium octanoate (764-71-6) → octanoyl-phosphoramidic acid diethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1.1: CH2Cl2 / 20 °C 2.1: BuLi 2.2: CH2Cl2 / -78 - 18 °C View Scheme

uranyl(VI) nitrate + potassium octanoate (764-71-6) → uranyl octanoate

Conditions	Yield
In water direct metathesis of potassium soap with aq. soln. of U-compd. with constant stirring; filtered, washed (H2O, EtOH), dried in air-oven at 50°C, then under reduced pressure at room temp.;

potassium octanoate (764-71-6) + copper(II) sulfate (7758-99-8) → copper(II) octanoate (3890-89-9, 20543-04-8, 104790-45-6, 148056-56-8)

Conditions	Yield
In not given 50-55°C; product was washed with water and alcohol, dried at 100-105°C under reduced pressure, and recrystd. from hot benzene; elem. anal.;

samarium(III) nitrate hexahydrate + potassium octanoate (764-71-6) → samarium caprylate

Conditions	Yield
In water vigorous stirring of the potassiuum soap with a slight excess of an aq. soln. of samarium nitrate at 50-55°C, pptn.; filtration, washing (distd. water, alcohol), recrystn. (benzene/methanol), drying (reduced pressure); elem. anal.;

samarium(III) ion + potassium octanoate (764-71-6) → samarium caprylate

Conditions	Yield
In not given slight excess of lanthanide salt, vigorous stirring (50 - 60°C, pptn.); digestion, filtration, washing (H2O, ether), drying, recrystn. (benzene/MeOH);

sodium molybdate dihydrate (7631-95-0) + potassium octanoate (764-71-6) → di-μ-oxo(oxomolybdenum(V))2((n-heptyl)COO)2

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium dithionite In water Na2MoO4 in H2O is depolymerized mit concd. NaOH until pH=9, mixt. is added to carboxylate soln., sodium dithionite is added and the pH adjusted to pH=2-3 by addn. of dilute HCl, mixt. was maintained for 48 h in the dark; brown ppt. is separated by filtration, washed (cold water), dried over P4O10 in N2 atmosphere, elem. anal.;	40-50

zinc diacetate (557-34-6) + potassium octanoate (764-71-6) → zinc(II) octanoate (557-09-5)

Conditions	Yield
In water metathesis of potassium caprylate with zinc acetate at 50-55 °C; the ppt. was digested, filtered and washed with hot dest. water, then with acetone, dried first in an air oven at 60-65 °C, then in vac. and recrystn. twice from benzene, dried again in vac. for 48 h; elem. anal.;;

cis-diaquabis(ethane-1,2-diamine)cobalt(III) perchlorate + potassium octanoate (764-71-6) → cis-{Co(n-C7H15CO2)2en2}ClO4

Conditions	Yield
In water evaporation of the soln.-mixture of (Coaq2en2)(ClO4)3 and KC7H15CO2 in vac. at room temperature; extraction of the residue with alcohol; crystallization from the filtrated alc. soln.;;

cerium(III) ion + potassium octanoate (764-71-6) → cerium(III) octanoate

Conditions	Yield
In not given slight excess of lanthanide salt, vigorous stirring (50 - 60°C, pptn.); digestion, filtration, washing (H2O, ether), drying, recrystn. (benzene/MeOH);

neodymium(III) + potassium octanoate (764-71-6) → neodymium(III) heptanoate (79321-04-3)

Conditions	Yield
In not given slight excess of lanthanide salt, vigorous stirring (50 - 60°C, pptn.); digestion, filtration, washing (H2O, ether), drying, recrystn. (benzene/MeOH);

zirconium(IV) oxychloride + potassium octanoate (764-71-6) → zirconyl dioctanoate

Conditions	Yield
In water direct metathesis; recrystn. (benzene-methanol); m. p. (146°C), elem. anal., IR;

potassium octanoate (764-71-6) + cadmium(II) nitrate → cadmium(II) caprylate

Conditions	Yield
In methanol; water prepn. by adding satd. aq. soln. of metal nitrate to soln. of potassium caprylate in MeOH; crystd. several times from hot toluene; dried at 50°C for 1 d;

potassium octanoate (764-71-6) + cobalt(II) nitrate → cobalt octanoate (1588-79-0, 2114-47-8, 6700-85-2, 25447-72-7)

Conditions	Yield
In methanol; water prepn. by adding satd. aq. soln. of metal nitrate to soln. of potassium caprylate in MeOH; washed repeatedly with hot H2O; dried at 50°C for 1 d;

zinc(II) nitrate (10196-18-6) + potassium octanoate (764-71-6) → zinc(II) octanoate (557-09-5)

Conditions	Yield
In methanol; water prepn. by adding satd. aq. soln. of metal nitrate to soln. of potassium caprylate in MeOH; crystd. several times from hot toluene; dried at 50°C for 1 d;

lead(II) nitrate + potassium octanoate (764-71-6) → lead 2-ethylhexoate (7319-86-0, 15696-43-2, 105833-70-3)

Conditions	Yield
In methanol; water prepn. by adding satd. aq. soln. of metal nitrate to soln. of potassium caprylate in MeOH; crystd. several times from hot toluene; dried at 50°C for 1 d;

C20H23BrN2O4 + potassium octanoate (764-71-6) → C28H38N2O6 + C28H38N2O6

Conditions	Yield
With 18-crown-6 ether In acetonitrile at 75℃; for 24h; Overall yield = 64 %;

Upstream product

• 124-07-2 Octanoic acid 
• 111-87-5 octanol 

Downstream Products

• 629-04-9 1-Bromoheptane 
• 3890-89-9 copper(II) octanoate 
• 557-09-5 zinc(II) octanoate 
• 79321-04-3 neodymium(III) heptanoate 
• 1588-79-0 cobalt octanoate 
• 7319-86-0 lead 2-ethylhexoate 

Relevant articles and documents

A cyclometalated Ir(iii)-NHC complex as a recyclable catalyst for acceptorless dehydrogenation of alcohols to carboxylic acids

In this work, we have synthesized two new [C, C] cyclometalated Ir(iii)-NHC complexes, [IrCp?(C∧C:NHC)Br](1a,b), [Cp? = pentamethylcyclopentadienyl; NHC = (2-flurobenzyl)-1-(4-methoxyphenyl)-1H-imidazoline-2-ylidene (a); (2-flurobenzyl)-1-(4-formylphenyl)-1H-imidazoline-2-ylidene (b)] via intramolecular C-H bond activation. The molecular structure of complex 1a was determined by X-ray single crystal analysis. The catalytic potentials of the complexes were explored for acceptorless dehydrogenation of alcohols to carboxylic acids with concomitant hydrogen gas evolution. Under similar experimental conditions, complex 1a was found to be slightly more efficient than complex 1b. Using 0.1 mol% of complex 1a, good-to-excellent yields of carboxylic acids/carboxylates have been obtained for a wide range of alcohols, both aliphatic and aromatic, including those involving heterocycles, in a short reaction time with a low loading of catalyst. Remarkably, our method can produce benzoic acid from benzyl alcohol on a gram scale with a catalyst-to-substrate ratio as low as 1?:?5000 and exhibit a TON of 4550. Furthermore, the catalyst could be recycled at least three times without losing its activity. A mechanism has been proposed based on controlled experiments and in situ NMR study.

Iridium catalysts for acceptorless dehydrogenation of alcohols to carboxylic acids: Scope and mechanism

We introduce iridium-based conditions for the conversion of primary alcohols to potassium carboxylates (or carboxylic acids) in the presence of potassium hydroxide and either [Ir(2-PyCH2(C4H5N2))(COD)]OTf (1) or [Ir(2-PyCH2PBu2t)(COD)]OTf (2). The method provides both aliphatic and benzylic carboxylates in high yield and with outstanding functional group tolerance. We illustrate the application of this method to a diverse variety of primary alcohols, including those involving heterocycles and even free amines. Complex 2 reacts with alcohols to form the crystallographically characterized catalytic intermediates [IrH(η1,η3-C8H12)(2-PyCH2PtBu2)] (2a) and [Ir2H3(CO)(2-PyCH2PtBu2){μ-(C5H3N)CH2PtBu2}] (2c). The unexpected similarities in reactivities of 1 and 2 in this reaction, along with synthetic studies on several of our iridium intermediates, enable us to form a general proposal of the mechanisms of catalyst activation that govern the disparate reactivities of 1 and 2, respectively, in glycerol and formic acid dehydrogenation. Moreover, careful analysis of the organic intermediates in the oxidation sequence enable new insights into the role of Tishchenko and Cannizzaro reactions in the overall oxidation.