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106-32-1

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106-32-1 Usage

Description

Ethyl caprylate (ethyl octanoate) is a kind of fatty acid ester formed from caprylic acid and ethanol. It is a kind of natural fruit flavoring agent. It is usually included in the alcohol beverage. Among the main flavoring components of None-flavor liquor, the absolute content of ethyl caprylate is not high but its flavoring contributions is higher than ethyl acetate, ethyl lactate, and ethyl butyrate, only lower than ethyl caproate. Only small amount of ethyl caprylate could produce obvious fruit aroma in Nong-flavor liquor. However, excessive content of ethyl caprylate would inhibit the performance of other flavoring components.

Chemical Properties

Different sources of media describe the Chemical Properties of 106-32-1 differently. You can refer to the following data:
1. CLEAR COLOURLESS LIQUID
2. Ethyl Octanoate is a liquid with a fruity, floral odor. It occurs in many fruits and alcoholic beverages and is used in fruit flavors.
3. Ethyl octanoate has a pleasant, fruity, floral odor (wine–apricot note)

Occurrence

Reported found in apple, apricot, orange juice, grapefruit juice, guava, pineapple, cheddar cheese, other cheeses, butter, beer, cognac, rum, whiskey, cider, grape wines, cocoa, coconut meat, passion fruit, mango, pawpaw and mastic gum leaf oil.

Uses

Different sources of media describe the Uses of 106-32-1 differently. You can refer to the following data:
1. manufacture of fruit ethers; constituent of enanthic, cocoic, and cognac ethers.
2. Ethyl caprylate is a flavoring and fragrance agent.
3. Ethyl octanoate, found in Burgundy wine, was used to study its partition co-efficient in water in model wine using the headspace method.

Preparation

Usually prepared by esterification of caprylic acid with ethyl alcohol and sulfuric acid as catalyst; also by alcoholysis of coconut oil in the presence of HCl.

Definition

ChEBI: A fatty acid ethyl ester resulting from the formal condensation of octanoic acid with ethanol.

Aroma threshold values

Detection: 5 to 92 ppb

Taste threshold values

Taste characteristics at 5 ppm: waxy, fatty, aldehydic, coconut, creamy and dairy-like.

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 6804, 1967 DOI: 10.1021/ja01001a097The Journal of Organic Chemistry, 42, p. 3209, 1977 DOI: 10.1021/jo00439a026

General Description

Ethyl octanoate is a powerful odourant found in mead (a traditional drink that contains alcohol).

Flammability and Explosibility

Notclassified

Safety Profile

Mddly toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

Carcinogenicity

Not listed by ACGIH, California Proposition 65, IARC, NTP, or OSHA.

Metabolism

Aliphatic esters including ethyl caprylate are thought to be readily hydrolysed to the corresponding alcohol and acid, which are then further metabolized (Fassett, 1963). Oral adminis tration of ethyl caprylate to rats produced a ketonuria twice as great as that from acetoacetate, indicating the formation of two fragments for the production of ketone bodies, and it was suggested that caprylic acid was probably broken down by a process involving multiple alternate oxidation (Deuel, Hallman, Butts & Murray, 1936).

References

Powers, John J. "HETEROGENEITY AND TEMPERATURE EFFECTS ON FLAVOR SENSING OF ETHYL CAPRYLATE." Journal of Food Science 42.1(2010):275-276. Zhibin, L. I., and L. I. Jin. "Analysis of the Content of Ethyl Caprylate in Nong-flavor Liquor and Its Flavoring Contributions." Liquor-Making Science & Technology (2013).

Check Digit Verification of cas no

The CAS Registry Mumber 106-32-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 106-32:
(5*1)+(4*0)+(3*6)+(2*3)+(1*2)=31
31 % 10 = 1
So 106-32-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H20O2/c1-3-5-6-7-8-9-10(11)12-4-2/h3-9H2,1-2H3

106-32-1 Well-known Company Product Price

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  • Alfa Aesar

  • (B23450)  Ethyl octanoate, 99%   

  • 106-32-1

  • 100g

  • 262.0CNY

  • Detail
  • Alfa Aesar

  • (B23450)  Ethyl octanoate, 99%   

  • 106-32-1

  • 500g

  • 613.0CNY

  • Detail

106-32-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl octanoate

1.2 Other means of identification

Product number -
Other names n-Octanoic Acid Ethyl Ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-32-1 SDS

106-32-1Synthetic route

ethyl (2E)-oct-2-enoate
2351-90-8, 7367-82-0, 42778-93-8

ethyl (2E)-oct-2-enoate

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With diisobutylaluminium hydride; cobalt acetylacetonate In tetrahydrofuran; hexane at -78 - 0℃; for 2h;99.5%
ethanol
64-17-5

ethanol

methyl octanate
111-11-5

methyl octanate

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) for 8h; Heating;97%
ethyl 3-octenoate
1117-65-3

ethyl 3-octenoate

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With ethanol; (BQ‑NCOP)IrHCl; sodium t-butanolate at 60℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;97%
ethanol
64-17-5

ethanol

Octanoic acid
124-07-2

Octanoic acid

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With mesoporous MCM silicas at 60℃; for 6h;95%
With sulfuric acid at 25℃; for 0.5h; ultrasonic irradiation;95%
With TiO2-doped zirconia for 6h; Reflux;95.1%
Octanoic acid
124-07-2

Octanoic acid

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane at 0℃; for 0.5h;95%
With pentabutyl propyl guanidinium chloride; silica gel at 120℃; for 4h;95%
With dmap; triethylamine 1.) CH2Cl2, 0 deg C, 5 min, 2.) 0 deg C, 0.5 h; Yield given. Multistep reaction;
C14H27O6P

C14H27O6P

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With 10% palladium on activated carbon; hydrogen In ethanol at 20℃; for 3h;95%
1-bromo-butane
109-65-9

1-bromo-butane

(4-ethoxy-4-oxobutyl)zinc(II) bromide
151073-69-7

(4-ethoxy-4-oxobutyl)zinc(II) bromide

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Negishi cross-coupling;92%
With n-butylzinc bromide; tris(dibenzylideneacetone)dipalladium (0); 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Negishi cross-coupling;92%
With tris(dibenzylideneacetone)dipalladium (0); n-butylzinc bromide; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Negishi cross-coupling;92%
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

n-butylzinc bromide
92273-73-9

n-butylzinc bromide

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran at 20℃; for 24h; Negishi cross-coupling;92%
tris(dibenzylideneacetone)dipalladium (0); 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Negishi cross-coupling;92%
Stage #1: n-butylzinc bromide With tris(dibenzylideneacetone)dipalladium (0); 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 1h;
Stage #2: Ethyl 4-bromobutyrate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Negishi cross-coupling;
92%
(ethoxycarbonyl)octanoate
71478-41-6

(ethoxycarbonyl)octanoate

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane for 0.25h; Ambient temperature;91%
ethyl 2-(pyrimidin-2-ylsulfonyl)octanoate
288400-58-8

ethyl 2-(pyrimidin-2-ylsulfonyl)octanoate

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 1h; desulfonylation; Heating;91%
Octanoic acid
124-07-2

Octanoic acid

ethylene glycol
107-21-1

ethylene glycol

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
at 120℃; for 2h;90%
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

butyl magnesium bromide
693-04-9

butyl magnesium bromide

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
dilithium tetrachlorocuprate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; Alkylation;86%
With [((Me)NN2)NiCl] In tetrahydrofuran; ISOPROPYLAMIDE at -35 - 20℃; Inert atmosphere;85%
With N,N,N,N,-tetramethylethylenediamine; C34H46Cl4N10Ni2O2 In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;81%
ethanol
64-17-5

ethanol

(E)-2-Nonenal
18829-56-6

(E)-2-Nonenal

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With 2-mesityl-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazol-4-ium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃; for 24h;86%
ethanol
64-17-5

ethanol

Octanal
124-13-0

Octanal

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: Octanal With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃; for 0.5h;
Stage #2: ethanol With sulfuric acid In dimethyl sulfoxide at 130℃; for 2.5h;
85%
With Mo(Oxo)/C at 90℃; for 2h; Catalytic behavior;50%
With manganese(IV) oxide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 24h; Inert atmosphere;30%
(i) MeLi, THF, (ii) /BRN= 1744086/, (iii) O3; Multistep reaction;
With oxygen at 100℃; under 3750.38 Torr; for 5h; Reagent/catalyst; Pressure; Autoclave;74 %Chromat.
ethanol
64-17-5

ethanol

octanal oxime
929-55-5

octanal oxime

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With 2-nitrobenzeneseleninic acid; dihydrogen peroxide at 20℃; for 24h;85%
1-hexene
592-41-6

1-hexene

ethyl bromoacetate
105-36-2

ethyl bromoacetate

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
In hexane; water for 6h; Solvent; Irradiation;77%
ethyl 3-iodopropanoate
6414-69-3

ethyl 3-iodopropanoate

dipentylzinc
14402-93-8

dipentylzinc

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With 3-(trifluoromethyl)styrene; bis(acetylacetonate)nickel(II) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at -35℃; for 4h; Substitution;72%
1-hexene
592-41-6

1-hexene

methylthioacetic acid ethyl ester
4455-13-4

methylthioacetic acid ethyl ester

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
In acetonitrile at 18 - 20℃; for 2.5h;70%
ethyl 4-iodobutyrate
7425-53-8

ethyl 4-iodobutyrate

lithium di-tert-butylphosphido(n-butyl)cuprate

lithium di-tert-butylphosphido(n-butyl)cuprate

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
In diethyl ether react. of Cu complex with organic electrophile at 0°C, 2 h;67%
In diethyl ether at 0℃; for 2h;67 % Chromat.
ethanol
64-17-5

ethanol

1,3-propanediol dicaprylate
56519-71-2

1,3-propanediol dicaprylate

A

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

B

propyl octanoate
624-13-5

propyl octanoate

Conditions
ConditionsYield
With Mo(Oxo)/C at 90℃; under 10343.2 Torr; for 2h; Catalytic behavior; Inert atmosphere;A 66%
B 17%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

nHeptMg halide/TDA-1

nHeptMg halide/TDA-1

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
In diethyl ether at 0℃; for 3h;45%
ethyl octyl ether
929-61-3

ethyl octyl ether

A

Octanoic acid
124-07-2

Octanoic acid

B

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

C

nonanoic acid methyl ester
1731-84-6

nonanoic acid methyl ester

D

octyl octylate
2306-88-9

octyl octylate

Conditions
ConditionsYield
With sodium bromate; sodium hydrogensulfite In water at 20℃; for 16.25h; Oxidation;A 31%
B 7%
C 13%
D 44%
ethanol
64-17-5

ethanol

octyl octylate
2306-88-9

octyl octylate

A

octanol
111-87-5

octanol

B

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With Mo(Oxo)/C at 90℃; under 10343.2 Torr; for 16h; Catalytic behavior; Inert atmosphere;A 43%
B 40%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

hexane
110-54-3

hexane

A

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

B

3-ethyl-hexanoic acid, ethyl ester
84612-77-1

3-ethyl-hexanoic acid, ethyl ester

C

3-methyl-heptanoic acid ethyl ester
37492-08-3

3-methyl-heptanoic acid ethyl ester

D

octanoyloxy-acetic acid ethyl ester

octanoyloxy-acetic acid ethyl ester

E

C12H22O4

C12H22O4

Conditions
ConditionsYield
With C15HBBr3F18N6(1-)*Ag(1+)*C4H8O In water at 20℃; regioselective reaction;A 23%
B 10%
C 30%
D 7%
E 9%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Trihexylboran; Tri-n-hexylbor
1188-92-7

Trihexylboran; Tri-n-hexylbor

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With water In tetrahydrofuran
1-hexene
592-41-6

1-hexene

(ethoxycarbonylmethyl)dimethylsulfonium bromide
5187-82-6

(ethoxycarbonylmethyl)dimethylsulfonium bromide

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
(i) BH3, (ii) /BRN= 4161472/, NaH, (iii) aq. H2O2, NaOH; Multistep reaction;
n-heptylmagnesium bromide
13125-66-1

n-heptylmagnesium bromide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
(i) MnI2, Et2O, (ii) /BRN= 385653/; Multistep reaction;
tripentylborane
1883-38-1

tripentylborane

ethyl acrylate
140-88-5

ethyl acrylate

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
(i) I, (electrolysis), (ii) aq. NaOH, H2O2; Multistep reaction;
ethanol
64-17-5

ethanol

2,2,2-trifluoroethyl octanoate
2264-29-1

2,2,2-trifluoroethyl octanoate

A

2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

B

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
In di-isopropyl ether at 25.5℃; Kinetics; immobilized lipase; various inhibitors and buffers;
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

hexane
110-54-3

hexane

A

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

B

3-ethyl-hexanoic acid, ethyl ester
84612-77-1

3-ethyl-hexanoic acid, ethyl ester

C

3-methyl-heptanoic acid ethyl ester
37492-08-3

3-methyl-heptanoic acid ethyl ester

Conditions
ConditionsYield
RhTMPI at 60℃; Yield given. Yields of byproduct given;
Rhpiv at 60℃; for 0.5h; Yield given. Yields of byproduct given;
RhTPPI at 60℃; for 0.5h; Yield given. Yields of byproduct given;
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

phenylacetylene
536-74-3

phenylacetylene

1-phenyldec-1-yn-3-one
100905-25-7

1-phenyldec-1-yn-3-one

Conditions
ConditionsYield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: octanoic acid ethyl ester With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃;
100%
With potassium tert-butylate In tetrahydrofuran for 0.0833333h;
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

<1-2H2>-1-octanol
78510-02-8

<1-2H2>-1-octanol

Conditions
ConditionsYield
With lithium aluminium deuteride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 5h;99%
With lithium aluminium deuteride In diethyl ether 1.) room temperature, 30 min 2.) reflux, 2 h;98%
With lithium aluminium deuteride
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With aluminum oxide; potassium hydroxide In toluene for 18h; Product distribution; Ambient temperature;98%
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h;95%
With Rhodococcus sp. LKE-028 esterase at 70℃; pH=11; aq. buffer; Enzymatic reaction;
methanol
67-56-1

methanol

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

methyl octanate
111-11-5

methyl octanate

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) at 64℃; for 8h;98%
With bromobenzene; hydrogen at 40℃; under 1500.15 Torr; for 3h; Autoclave;95%
With Dowex DR2030 ion exchange resin at 59.84℃; under 760.051 Torr; for 3h;
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

octanol
111-87-5

octanol

Conditions
ConditionsYield
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Reagent/catalyst; Temperature; Pressure; Glovebox; Autoclave;96%
Stage #1: octanoic acid ethyl ester With C33H58FeN3PSi2; phenylsilane In toluene at 20℃; for 4h; Inert atmosphere; Glovebox; Green chemistry;
Stage #2: With sodium hydroxide In toluene for 1h; Green chemistry;
80%
With methanol; sodium tetrahydroborate; sodium ethanolate at 40℃;80%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

cyclohexylamine
108-91-8

cyclohexylamine

N-(cyclohexyl)-n-octanoylamide
42577-04-8

N-(cyclohexyl)-n-octanoylamide

Conditions
ConditionsYield
With potassium tert-butylate for 0.0583333h; microwave irradiation;96%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

caprylohydroxamic acid
7377-03-9

caprylohydroxamic acid

Conditions
ConditionsYield
Stage #1: octanoic acid ethyl ester With sodium ethanolate; sodium carbonate In ethanol at 40℃; for 2.5h;
Stage #2: With hydroxylamine In ethanol; water
95.7%
With sodium sulfide; hydroxylamine hydrochloride; sodium hydroxide In ethanol at 20 - 45℃; for 3h; Temperature; Concentration;93.1%
With hydroxylamine hydrochloride; potassium hydroxide In ethanol; water at 5 - 55℃; for 3h; Concentration; Temperature;91.1%
3-sulfanylpropanol
19721-22-3

3-sulfanylpropanol

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Octanoic acid 3-mercapto-propyl ester

Octanoic acid 3-mercapto-propyl ester

Conditions
ConditionsYield
at 31℃; for 168h; porcine pancreatic lipase;95.5%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

n-octanamide
629-01-6

n-octanamide

Conditions
ConditionsYield
With ammonia at 40℃; for 24h; Temperature; Concentration; Enzymatic reaction;95%
With ammonia; water
Multi-step reaction with 2 steps
1: Candida antarctica lipase B (Novozym 435); 1-butyl-3-methylimidazolium tetrafluoroborate; NH3 / 24 h / 40 °C
2: Candida antarctica lipase B (Novozym 435); 1-butyl-3-methylimidazolium tetrafluoroborate; NH3 / 96 h / 40 °C
View Scheme
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

[bis(phenylthio)methyl]lithium
13307-76-1

[bis(phenylthio)methyl]lithium

1,1-Bis-phenylsulfanyl-nonan-2-one
75456-51-8

1,1-Bis-phenylsulfanyl-nonan-2-one

Conditions
ConditionsYield
95%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

aniline
62-53-3

aniline

N-phenylhexanamide
6998-10-3

N-phenylhexanamide

Conditions
ConditionsYield
With potassium tert-butylate for 0.05h; microwave irradiation;95%
1-iodo-butane
542-69-8

1-iodo-butane

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

5-butyl-dodecan-5-ol
93314-38-6

5-butyl-dodecan-5-ol

Conditions
ConditionsYield
With nickel(II) iodide; samarium diiodide In various solvent(s) at 20℃; for 0.5h;94%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

N-butylamine
109-73-9

N-butylamine

N-butyloctanamide
24928-30-1

N-butyloctanamide

Conditions
ConditionsYield
With potassium tert-butylate for 0.116667h; microwave irradiation;92%
methanol
67-56-1

methanol

1-bromo-butane
109-65-9

1-bromo-butane

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

2-butyloctanoic acid
27610-92-0

2-butyloctanoic acid

Conditions
ConditionsYield
Stage #1: methanol; 1-bromo-butane; octanoic acid ethyl ester With sodium hydroxide at 20 - 55℃; for 7h; Large scale;
Stage #2: With water; sodium carbonate at 70℃; for 6h; Large scale;
91.43%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

isopropyl alcohol
67-63-0

isopropyl alcohol

1-methylethyl octanoate
5458-59-3

1-methylethyl octanoate

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) for 132h; Heating;90%
4-Mercapto-1-butanol
14970-83-3

4-Mercapto-1-butanol

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Octanoic acid 4-mercapto-butyl ester

Octanoic acid 4-mercapto-butyl ester

Conditions
ConditionsYield
at 30℃; for 48h; lipase from the yeast Candida cylindracea;88.4%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

1-(phenoxymethyl)-1H-benzo[d][1,2,3]triazole
111198-02-8

1-(phenoxymethyl)-1H-benzo[d][1,2,3]triazole

1-Benzotriazol-1-yl-1-phenoxy-nonan-2-one
189343-54-2

1-Benzotriazol-1-yl-1-phenoxy-nonan-2-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h;88%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

tris(phenylthio)methane
4832-52-4

tris(phenylthio)methane

((Z)-2-Ethoxy-non-1-enylsulfanyl)-benzene

((Z)-2-Ethoxy-non-1-enylsulfanyl)-benzene

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; 4 A molecular sieve; magnesium; triethyl phosphite In tetrahydrofuran for 3h; Heating;88%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

n-heptyl n-perfluorobutyl ketone
1262844-05-2

n-heptyl n-perfluorobutyl ketone

Conditions
ConditionsYield
Stage #1: 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane With ethylmagnesium bromide In diethyl ether at -70℃; for 1.5h;
Stage #2: octanoic acid ethyl ester In diethyl ether at -70 - -60℃; for 16.5h;
87%

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106-32-1Relevant articles and documents

The first Negishi cross-coupling reaction of two alkyl centers utilizing a Pd-N-heterocyclic carbene (NHC) catalyst

Hadei, Niloufar,Kantchev, Eric Assen B.,O'Brien, Christopher J.,Organ, Michael G.

, p. 3805 - 3807 (2005)

(Chemical Equation Presented) The development of an NHC-based system capable of cross-coupling sp3-sp3 centers in high yield has been a long-standing challenge. This communication describes the use of a Pd-NHC catalytic system that achieves room-temperature Negishi cross-couplings of unactivated, primary bromides and alkyl organozinc reagents with a variety of functionality.

-

Collman et al.

, p. 249 (1973)

-

Ultrasound-assisted synthesis of aliphatic acid esters at room temperature

Hobuss, Cristiane B.,Venzke, Dalila,Pacheco, Bruna S.,Souza, Alexander O.,Santos, Marco A.Z.,Moura, Sidnei,Quina, Frank H.,Fiametti, Karina G.,Vladimir Oliveira,Pereira, Claudio M.P.

, p. 387 - 389 (2012)

This work describes the ultrasound-assisted synthesis of saturated aliphatic esters from synthetic aliphatic acids and either methanol or ethanol. The products were isolated in good yields after short reaction times under mild conditions.

Oxidative esterification of aliphatic aldehydes and alcohols with ethanol over gold nanoparticle catalysts in batch and continuous flow reactors

Taketoshi,Ishida,Murayama, Toru,Honma, Tetsuo,Haruta, Masatake

, (2019)

Selective esterification of aliphatic aldehydes and alcohols with ethanol in the absence of a base is a more difficult reaction than that with methanol. Gold nanoparticles on ZnO were found to catalyze the oxidative esterification of octanal to ethyl octanoate with high selectivity. In addition, it was found that Au/ZnO was the most effective catalyst for yielding the desired ethyl ester without a base by direct esterification of 1-octanol with ethanol. As far as we know, this is the first report on oxidative esterification to give aliphatic ethyl esters from less reactive aliphatic alcohols and aldehydes without a base. The optimal size of gold NPs ranged from 2 to 6 nm and the presence of Au(0) was indispensable for this reaction. Au/ZnO exhibited the highest catalytic activity in both batch and flow reactors. The conversion was maintained for more than 20 h with 95% selectivity to the desired ethyl ester in the flow system.

Tandem one-pot conversion of aldehydes into ethyl esters

Siler, Patrick J.,Chill, Samuel T.,Mebane, Robert C.

, p. 1247 - 1250 (2011)

A facile one-pot synthesis of ethyl esters from aldehydes has been developed. This tandem process involves the formation of a nitrile intermediate obtained from the reaction of an aldehyde with hydroxylamine hydrochloride in dimethylsulfoxide (DMSO) at 100°C and the subsequent reaction of the nitrile with ethanol and sulfuric acid at 130°C. The resulting ethyl ester products were produced in good yields (65-90%) and high purity (>95%).

Towards the rational design of palladium-N-heterocyclic carbene catalysts by a combined experimental and computational approach

O'Brien, Christopher J.,Kantchev, Eric Assen B.,Chass, Gregory A.,Hadei, Niloufar,Hopkinson, Alan C.,Organ, Michael G.,Setiadi, David H.,Tang, Ting-Hua,Fang, De-Cai

, p. 9723 - 9735 (2005)

A combined experimental and computational approach towards the development of Pd-NHC catalysts is described. A range of benzimidazolylidinium ligands incorporating electron-rich and electron-poor substituents were prepared and evaluated in the Suzuki reaction. The most electron-rich ligand showed the highest catalytic activity. Based on this information, the first alkyl-alkyl Negishi cross-coupling reaction protocol was developed. Evaluation of N,N′-diaryl-(4,5-dihydro)imidazolylilidinium ligands showed a strong dependence on the steric topography around the metal centre. A computational study of the most active ligand in the Negishi reaction, its Pd(0) and PdCl 2-complexes and related structures were modelled at the B3LYP/DZVP and HF/3-21G levels of theory. The potential energy hypersurfaces flattened with increase in ligand size. Binding energies were computed for carbene/Pd(0) adducts (in the range ~31-40 kcal mol-1), roughly double that for PH3 (~16 kcal mol-1). Weak intramolecular interactions were found using AIM analyses.

Selective esterification reaction involving hexaalkyl guanidinium chloride catalyst

Gros,Le Perchec,Gauthier,Senet

, p. 1835 - 1842 (1993)

A new efficient and selective esterification reaction of carboxylic acids with chloroformates is described using silica-supported catalyst (PBGSiCl). The chemioselectivity of the reaction was high particularly for sterically hindered carboxylic acids supported by a single pathway reaction.

"Nafion"-functionalized mesoporous MCM-41 silica shows high activity and selectivity for carboxylic acid esterification and Friedel-Crafts acylation reactions

Alvaro, Mercedes,Corma, Avelino,Das, Debasish,Fornes, Vicente,Garcia, Hermenegildo

, p. 48 - 55 (2005)

Hybrid organic-inorganic MCM-41 silicas functionalized with perfluoroalkylsulfonic acid groups analogous to that of Nafion were prepared in a simple single step by a condensation reaction between surface silanol groups of the mesoporous silicas and 1,2,2-trifluoro-2-hydroxy-1-trifluoromethyl-ethane sulfonic acid Beta-sultone. The catalysts showed very high activity for the esterification of long-chain fatty acids with ethanol and high-molecular-weight alcohols with essentially complete selectivity at high conversion (>95%). Acylation of anisole was also possible, with high selectivity for 4-methoxyacetophenone. The catalysts showed more activity conversion than commercial Nafion-silica composite catalysts.

Tin-free reductive photochemical carboxymethylation of olefins with α- alkylthioacetates

Deng, Lisa X.,Kutateladze, Andrei G.

, p. 7829 - 7832 (1997)

An efficient tin-free reductive photochemical carboxymethylation of olefins with α-alkylthioacetates is developed, which (a) is an experimentally simple technique furnishing substituted derivatives of fatty acids in moderate to good yields, (b) is compatible with polar/protic functional groups and solvents, (c) does not require a special reducing reagent, (d) is fairly insensitive to the presence of dissolved oxygen and, generally, does not require degassing prior to irradiation. The critical feature of the mechanism is the 'reluctance' of short-lived MeS' to group- transfer, resulting in hydrogen abstraction from the media.

Stability of sulfated zirconia and the nature of the catalytically active species in the transesterification of triglycerides

Suwannakarn, Kaewta,Lotero, Edgar,Goodwin Jr., James G.,Lu, Changqing

, p. 279 - 286 (2008)

Sulfated zirconia (SZ) exhibits remarkable activity for various hydrocarbon reactions under mild conditions and is of interest for biodiesel synthesis. Nevertheless, to date no detailed study has addressed its activity and stability in liquid polar media such as alcohols, although a number of papers have suggested the possibility for some sulfur leaching. This paper presents an investigation into the activity and stability of a commercial SZ catalyst for the liquid-phase transesterification of triglycerides at 120 °C. The kinetics of tricaprylin (TCP) transesterification with a series of aliphatic alcohols (methanol, ethanol, and n-butanol) were investigated at 120 °C and 6.8 atm in a Parr batch reactor. It was found that the catalytic activity for TCP conversion decreased as the number of carbons in the alkyl chain of alcohol increased, most likely as a result of increased steric hindrance. The SZ catalyst exhibited significant activity loss with subsequent reaction cycles. The characterization of used catalysts after their exposure to various alcohols at 120 °C showed that the SO2-4 moieties in SZ were permanently removed. The SO2-4 species were leached out, most likely as sulfuric acid, which further reacted with alcohols to form monoalkyl and dialkyl sulfate species, as demonstrated by 1H NMR studies. This was in essence the main route for catalyst deactivation. Our findings conclusively demonstrate for the first time that in alcoholic-liquid media at higher temperatures, SZ deactivates by leaching of its active sites, most likely leading to significant homogeneous rather than heterogeneous catalysis.

Copper catalyzed C(sp3)-H bond alkylation via photoinduced ligand-to-metal charge transfer

Treacy, Sean M.,Rovis, Tomislav

supporting information, p. 2729 - 2735 (2021/03/01)

Utilizing catalytic CuCl2 we report the functionalization of numerous feedstock chemicals via the coupling of unactivated C(sp3)-H bonds with electron-deficient olefins. The active cuprate catalyst undergoes Ligand-to-Metal Charge Transfer (LMCT) to enable the generation of a chlorine radical which acts as a powerful hydrogen atom transfer reagent capable of abstracting strong electron-rich C(sp3)-H bonds. Of note is that the chlorocuprate catalyst is an exceedingly mild oxidant (0.5 V vs SCE) and that a proposed protodemetalation mechanism offers a broad scope of electron-deficient olefins, offering high diastereoselectivity in the case of endocyclic alkenes. The coupling of chlorine radical generation with Cu reduction through LMCT enables the generation of a highly active HAT reagent in an operationally simple and atom economical protocol.

Fully recyclable Br?nsted acid catalyst systems

Watson, Christopher B.,Kuechle, Adrianna,Bergbreiter, David E.

, p. 1266 - 1273 (2021/02/26)

Homogeneous and heterogeneous sulfonic acid catalysts are some of the most common catalysts used in organic chemistry. This work explores an alternative scheme using a fully recyclable polymeric solvent (a poly-α-olefin (PAO)) and soluble PAO-anchored polyisobutylene (PIB)-bound sulfonic acid catalysts. This PAO solvent is nonvolatile and helps to exclude water by its nonpolar nature which in turn drives reactions without the need for distillation of water, avoiding the need for excess reagents. This highly nonpolar solvent system uses polyisobutylene (PIB) bound sulfonic acid catalysts that are phase-anchored in solvents like PAO. The effectivenes of these catalysts was demonstrated by their use in esterifications, acetalizations, and multicomponent condensations. These catalysts and the PAO solvent phase show excellent recyclability in schemes where products are efficiently separated. For example, this non-volatile polymeric solvent and the PIB-bound catalyst can be recycled quantitatively when volatile products are separated and purified by distillation. In other cases, product purification can be effected by product self-separation or by extraction.

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