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109-21-7

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109-21-7 Usage

Description

Butyl butyrate is a kind of ester formed through the condensation of butyric acid and n-butanol. It has a pleasant flavor, and thus being used in the flavor industry to generate a sweet fruity flavor of pineapple-like. It occurs naturally in many kinds of fruits including apple, banana, berries, pear, plum, and strawberry. It is also found in alcoholic beverages. However, it should be noted that it is a marine pollutant, posing a threat to the marine environment. It may also penetrate into soil, contaminating groundwater and other nearby waterways.

References

https://pubchem.ncbi.nlm.nih.gov/compound/Butyl_butyrate#section=Top https://en.wikipedia.org/wiki/Butyl_butyrate

Chemical Properties

Different sources of media describe the Chemical Properties of 109-21-7 differently. You can refer to the following data:
1. CLEAR COLORLESS TO PALE YELLOWISH LIQUID
2. Butyl Butyrate is a liquid with a sweet, fruity odor. It is a volatile constituent of many fruits and honey and is used in fruit flavor compositions.
3. Butyl butyrate has a fruity (pear–pineapple-like) odor.

Occurrence

Reported found in fresh apple, apple juice, banana, orange juice, orange peel oil, melon, strawberry, Passiflora mollisima, soybean, honey and blue cheese.

Uses

Different sources of media describe the Uses of 109-21-7 differently. You can refer to the following data:
1. It is very important for the food and beverages industries and used as perfuming agents. It is a applied as a solvent for resins.
2. Butyl butyrate can be used as a reactant to synthesize: N-(Phenylmethyl)butanamide by reacting with benzylamine via ester-amide exchange reaction in the presence of supported graphene oxide catalyst.Cyclohexyl butyrate by acylation reaction with cyclohexanol using a ruthenium pincer PNN complex catalyst.Butyl ether by triiron dodecacarbonyl catalyzed hydrosilylation reaction.
3. Flavoring.

Definition

ChEBI: A butanoate ester of butan-1-ol.

Preparation

By passing vapors of n-butyl alcohol over MnO2 or ZnO at 400°C, also by passing vapors of n-butyl alcohol over CuO-VO at 180 to 200°C.

Aroma threshold values

Detection: 87 to 1000 ppb

Taste threshold values

Taste characteristics at 40 ppm: sweet, fresh, fruity, slightly fatty.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2605, 1947 DOI: 10.1021/ja01203a011Organic Syntheses, Coll. Vol. 1, p. 138, 1941Tetrahedron Letters, 22, p. 5327, 1981 DOI: 10.1016/S0040-4039(01)92493-1

General Description

A colorless liquid. Insoluble in water. A marine pollutant. Poses a threat to the aquatic environment. Immediate steps should be taken to prevent spread to the environment. May penetrate soils and contaminate groundwater and nearby waterways. Mildly irritates the eyes and skin.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Butyl butyrate reacts with acids to liberate heat along with butyl alcohol and butyric acid. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by interaction with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides. May attack some forms of plastics [USCG, 1999].

Hazard

Irritant and narcotic. Moderate fire risk.

Fire Hazard

Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot.

Flammability and Explosibility

Flammable

Safety Profile

Moderately toxic via intraperitoneal route. Mildly toxic by ingestion. Moderately irritating to eyes, sh, and mucous membranes by inhalation. Narcotic in hgh concentrations. Flammable liquid. To fight fire, use alcohol foam, foam, CO2, dry chemical. Incompatible with oxidizing materials. When heated to decomposition it emits acrid and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 109-21-7 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 9 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 109-21:
(5*1)+(4*0)+(3*9)+(2*2)+(1*1)=37
37 % 10 = 7
So 109-21-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)/p-1

109-21-7 Well-known Company Product Price

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  • Alfa Aesar

  • (B24390)  n-Butyl butyrate, 99%   

  • 109-21-7

  • 250ml

  • 216.0CNY

  • Detail
  • Alfa Aesar

  • (B24390)  n-Butyl butyrate, 99%   

  • 109-21-7

  • 1000ml

  • 725.0CNY

  • Detail
  • Sigma-Aldrich

  • (67367)  Butylbutyrate  analytical standard

  • 109-21-7

  • 67367-1ML

  • 238.68CNY

  • Detail

109-21-7SDS

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 butyl butanoate

1.2 Other means of identification

Product number -
Other names Butyric Acid Butyl 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:109-21-7 SDS

109-21-7Synthetic route

butyric acid
107-92-6

butyric acid

butan-1-ol
71-36-3

butan-1-ol

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With [Al(H2O)6][MS]3 In cyclohexane for 1h; Reagent/catalyst; Dean-Stark; Reflux;100%
With Candida antarctica B lipase In 2,2,4-trimethylpentane at 40℃; for 3h; Enzymatic reaction;98%
With DOOl-AlCl3 superacid resin for 1.5h; Heating;97%
butan-1-ol
71-36-3

butan-1-ol

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With C29H44Cl2N2Ru; potassium tert-butylate In toluene for 15h; Reagent/catalyst; Time; Reflux;100%
Ru complex at 118℃; for 12h; Inert atmosphere;99%
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 2h;99%
butyraldehyde
123-72-8

butyraldehyde

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With trimethylaluminum; benzene-1,2-diol; isopropyl alcohol In dichloromethane at 20℃; for 2h;99%
With tris(bis(trimethylsilyl)amido)lanthanum(III) In hexane; pentane at -78 - 20℃;45%
With aluminum ethoxide
butanoic acid anhydride
106-31-0

butanoic acid anhydride

butan-1-ol
71-36-3

butan-1-ol

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With ruthenium(III) 2,4-pentanedionate at 25℃; for 1h;98%
CoCl2 In acetonitrile for 2h; Ambient temperature;89%
With dmap; triethylamine In dichloromethane
In p-cymene at 50℃; Kinetics; Solvent;
1-Chloropropane
540-54-5

1-Chloropropane

propoxycarbonyl chloride
109-61-5

propoxycarbonyl chloride

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
Stage #1: 1-Chloropropane With magnesium; 1,2-dibromomethane In toluene at 60℃; for 3h; Inert atmosphere;
Stage #2: propoxycarbonyl chloride With aluminum (III) chloride; manganese(ll) chloride In toluene at 0 - 20℃; for 2.25h; Inert atmosphere;
95%
triethylsilane
617-86-7

triethylsilane

A

triethylsilyl iodide
1112-49-8

triethylsilyl iodide

B

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With butyryl iodide; bis(acetylacetonate)nickel(II) at 20℃; for 2h;A 90%
B 81%
butyryl iodide
78209-72-0

butyryl iodide

A

triethylsilyl iodide
1112-49-8

triethylsilyl iodide

B

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With triethylsilane; bis(acetylacetonate)nickel(II) at 20℃; for 2h;A 90%
B 81%
1-bromo-butane
109-65-9

1-bromo-butane

sodium butyrate
156-54-7

sodium butyrate

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With polyethylene glycol 400 at 65 - 70℃; for 3.5h;90%
(PPh3)3CoH(N2)
21373-88-6, 16920-54-0

(PPh3)3CoH(N2)

phenyl butanoate
4346-18-3

phenyl butanoate

A

HCo(CO)(P(C6H5)3)3
53729-69-4, 21329-67-9

HCo(CO)(P(C6H5)3)3

B

phenoxotris(triphenylphosphine)cobalt(I)
91583-66-3

phenoxotris(triphenylphosphine)cobalt(I)

C

propane
74-98-6

propane

D

butyl butyrate
109-21-7

butyl butyrate

E

nitrogen
7727-37-9

nitrogen

Conditions
ConditionsYield
In toluene byproducts: H2; n-PrCO2Ph added to CoH(N2)(PPh3)3 in toluene in vac., reacted for 1 day at room temp.; liquid phase analysed by GLC; hexane added, ppt. filtered, washed with hexane, dried in vac., recrystd. from C6H6-hexane;A n/a
B 60%
C 12%
D 38%
E 89%
butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

butan-1-ol
71-36-3

butan-1-ol

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With rape seed lipase In hexane at 40℃; for 48h; Enzymatic reaction;88%
With Candida antarctica lipase B (Novozym 435); 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃; for 24h; Product distribution; Kinetics; Further Variations:; Reaction partners; Reagents;
With Candida antartica lipase B at 100℃; Enzyme kinetics; Further Variations:; Reagents; Temperatures;
butyraldehyde
123-72-8

butyraldehyde

A

butyl butyrate
109-21-7

butyl butyrate

B

butyric acid
107-92-6

butyric acid

C

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With dihydridotetrakis(triphenylphosphine)ruthenium; water; 1-Phenylbut-1-en-3-one In 1,2-dimethoxyethane at 180℃; for 24h; Product distribution; Mechanism; in the absence of hydrogen acceptor (benzalacetone); other aldehydes;A n/a
B 85%
C n/a
triethylsilane
617-86-7

triethylsilane

A

triethylsilyl chloride
994-30-9

triethylsilyl chloride

B

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With butyryl chloride; bis(acetylacetonate)nickel(II) at 90℃; for 2h;A 83%
B 68%
n-pentyldimethylsilane
29681-51-4

n-pentyldimethylsilane

A

butyl butyrate
109-21-7

butyl butyrate

B

dimethylpentylsilylchloride
25938-34-5

dimethylpentylsilylchloride

Conditions
ConditionsYield
With butyryl chloride; bis(acetylacetonate)nickel(II) at 90℃; for 2h;A 69%
B 81%
dimethylhexylsilane
63246-85-5

dimethylhexylsilane

A

butyl butyrate
109-21-7

butyl butyrate

B

dimethylhexylsilyl chloride
3634-59-1

dimethylhexylsilyl chloride

Conditions
ConditionsYield
With butyryl chloride; bis(acetylacetonate)nickel(II) at 90℃; for 2h;A 64%
B 81%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

(PPh3)3CoH(N2)
21373-88-6, 16920-54-0

(PPh3)3CoH(N2)

A

Co(OCO-n-C3H7)
99668-71-0

Co(OCO-n-C3H7)

B

propane
74-98-6

propane

C

butyl butyrate
109-21-7

butyl butyrate

D

nitrogen
7727-37-9

nitrogen

E

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
In toluene in toluene at room temp. for 1 day;A n/a
B 16%
C 30%
D 81%
E 13%
butyryl chloride
141-75-3

butyryl chloride

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With triethylsilane; iron(III)-acetylacetonate at 20℃;80%
dihydridotetrakis(triphenylphosphine)ruthenium
27599-25-3, 54083-06-6, 19529-00-1

dihydridotetrakis(triphenylphosphine)ruthenium

butyraldehyde
123-72-8

butyraldehyde

A

RuH(OCOC3H7)(P(C6H5)3)3
25087-79-0

RuH(OCOC3H7)(P(C6H5)3)3

B

butyl butyrate
109-21-7

butyl butyrate

C

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
In neat (no solvent) educts mixed at in vac., stirred at -30°C for 2 h; evapd. in vac., solid washed with Et2O and hexane, dissolved in toluene, filtered, concd. in vac., ppt. filtered, washed with hexane, dried in vac.;A 80%
B n/a
C <1
In neat (no solvent) educts mixed at in vac., stirred at 0°C for 2 h; evapd. in vac., solid washed with Et2O and hexane, dissolved in toluene, filtered, concd. in vac., ppt. filtered, washed with hexane, dried in vac.;A n/a
B 0%
C <1
propyl cyanide
109-74-0

propyl cyanide

butan-1-ol
71-36-3

butan-1-ol

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With Bromotrichloromethane; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate at 20℃; for 12h; Irradiation; Inert atmosphere;80%
butan-1-ol
71-36-3

butan-1-ol

A

butyl butyrate
109-21-7

butyl butyrate

B

butyraldehyde
123-72-8

butyraldehyde

Conditions
ConditionsYield
With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; iodine; sodium hydrogencarbonate In dichloromethane; water at 20 - 25℃; for 3h;A 79.7%
B 20.3%
With sodium chlorate; sulfuric acid; vanadia
With chromium(III) oxide; sulfuric acid
normal butyl hypochlorite
5923-22-8

normal butyl hypochlorite

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
In tetrachloromethane for 4h; Irradiation;78%
In benzene Ambient temperature; Irradiation;78%
butan-1-ol
71-36-3

butan-1-ol

A

butyl butyrate
109-21-7

butyl butyrate

B

butyric acid
107-92-6

butyric acid

Conditions
ConditionsYield
With sodium bromate; sodium hydrogensulfite for 2h; Ambient temperature;A 76%
B 5%
With sodium bromate; sodium hydrogensulfite for 2h; Product distribution; Mechanism; Ambient temperature; other primary alcohols and α,ω-diols, var. solvents, temp. and time;A 76%
B 5%
With [pentamethylcyclopentadienyl*Ir(2,2′-bpyO)(OH)][Na]; sodium hydroxide In water for 40h; Time; Reflux; Inert atmosphere;A 22%
B 70%
butyryl chloride
141-75-3

butyryl chloride

A

methyldiethylchlorosilane
17680-28-3

methyldiethylchlorosilane

B

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With diethylmethylsilane; bis(acetylacetonate)nickel(II) at 90℃; for 2h;A 76%
B 68%
1-butoxy-1-isobutoxy butane
20266-12-0

1-butoxy-1-isobutoxy butane

A

2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

B

butyl butyrate
109-21-7

butyl butyrate

C

isobutyl n-butyrate
539-90-2

isobutyl n-butyrate

D

isobutyric Acid
79-31-2

isobutyric Acid

E

butyric acid
107-92-6

butyric acid

F

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate at 90℃; under 750.06 Torr; Mechanism; Rate constant; other oxygen pressure;A 5.5%
B 3%
C 3.5%
D 5%
E 73.5%
F 7%
dibutyl ether
142-96-1

dibutyl ether

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
With manganese (VII)-oxide In tetrachloromethane; acetone at -45℃;73%
With zinc dichromate(VI) In dichloromethane for 3h; Ambient temperature;60%
With sodium bromate; hydrogen bromide In dichloromethane at 35 - 40℃; for 20h;54%
Octanal
124-13-0

Octanal

butan-1-ol
71-36-3

butan-1-ol

A

butyl butyrate
109-21-7

butyl butyrate

B

Octanoic acid
124-07-2

Octanoic acid

C

butyl octanoate
589-75-3

butyl octanoate

Conditions
ConditionsYield
With sodium bromate; sodium hydrogensulfite for 2h; Ambient temperature;A 17%
B 13%
C 70%
dibutyl ether
142-96-1

dibutyl ether

butyryl chloride
141-75-3

butyryl chloride

A

octane-4,5-dione
5455-24-3

octane-4,5-dione

B

butyl butyrate
109-21-7

butyl butyrate

Conditions
ConditionsYield
CoCl2 In acetonitrile Ambient temperature;A 10%
B 68%
dibutyl ether
142-96-1

dibutyl ether

A

butyl butyrate
109-21-7

butyl butyrate

B

butyric acid
107-92-6

butyric acid

C

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 4h;A 65%
B 8%
C 10%
ethanol
64-17-5

ethanol

crotonaldehyde
123-73-9

crotonaldehyde

A

ethyl crotonate
10544-63-5

ethyl crotonate

B

butyl butyrate
109-21-7

butyl butyrate

C

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With sodium carbonate; rhodium(III) chloride; triphenylphosphine for 5h; Heating;A 8 % Chromat.
B 61%
C 31%
crotonaldehyde
123-73-9

crotonaldehyde

A

ethyl crotonate
10544-63-5

ethyl crotonate

B

butyl butyrate
109-21-7

butyl butyrate

C

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With ethanol; sodium carbonate; rhodium(III) chloride; triphenylphosphine for 5h; Heating;A 8%
B 61%
C 31%
butyl butyrate
109-21-7

butyl butyrate

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave;98%
With hydrogen at 223.84℃; under 5625.56 Torr; Kinetics; Thermodynamic data; Concentration; Pressure; Temperature; neat (no solvent, gas phase);
With [RuH(η2-BH4)(2-di-tert-butylphosphinomethyl-6-diethylaminomethylpyridine)]; hydrogen In tetrahydrofuran at 110℃; under 7600.51 Torr; for 12h; Autoclave;97 %Chromat.
hexan-1-amine
111-26-2

hexan-1-amine

butyl butyrate
109-21-7

butyl butyrate

N-hexylbutanamide
10264-17-2

N-hexylbutanamide

Conditions
ConditionsYield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene; benzene at 135℃; for 24h; Inert atmosphere;97%
morpholine
110-91-8

morpholine

butyl butyrate
109-21-7

butyl butyrate

(N-morpholin-4-yl)butan-1-one
5327-51-5

(N-morpholin-4-yl)butan-1-one

Conditions
ConditionsYield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene; benzene at 135℃; for 21h; Inert atmosphere;95%
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium tert-butylate In toluene at 120℃; for 48h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;55%
piperidine
110-89-4

piperidine

butyl butyrate
109-21-7

butyl butyrate

1-(piperidin-1-yl)butan-1-one
4637-70-1

1-(piperidin-1-yl)butan-1-one

Conditions
ConditionsYield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene; benzene at 135℃; for 19h; Inert atmosphere;94%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

butyl butyrate
109-21-7

butyl butyrate

1-(4-methylpiperazin-1-yl)butan-1-one
10001-51-1

1-(4-methylpiperazin-1-yl)butan-1-one

Conditions
ConditionsYield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene; benzene at 135℃; for 24h; Inert atmosphere;94%
butyl butyrate
109-21-7

butyl butyrate

cyclohexanol
108-93-0

cyclohexanol

cyclohexyl butyrate
1551-44-6

cyclohexyl butyrate

Conditions
ConditionsYield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene for 34h; Inert atmosphere; Reflux;92%
butyl butyrate
109-21-7

butyl butyrate

para-fluorobenzylamine
140-75-0

para-fluorobenzylamine

N-(4-fluorobenzyl)butyramide

N-(4-fluorobenzyl)butyramide

Conditions
ConditionsYield
With C31H40MnN2O3P*C6H14O; potassium tert-butylate In toluene; 1,3,5-trimethyl-benzene at 110℃; for 48h; Schlenk technique;88%
bromobenzene
108-86-1

bromobenzene

butyl butyrate
109-21-7

butyl butyrate

1,1-diphenylbutan-1-ol
5331-17-9

1,1-diphenylbutan-1-ol

Conditions
ConditionsYield
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; Barbier Coupling Reaction; chemoselective reaction;87%
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; chemoselective reaction;87%
butyl butyrate
109-21-7

butyl butyrate

phenethylamine
64-04-0

phenethylamine

N-(2-phenylethyl)butanamide
6283-13-2

N-(2-phenylethyl)butanamide

Conditions
ConditionsYield
With C31H40MnN2O3P*C6H14O; potassium tert-butylate In toluene; 1,3,5-trimethyl-benzene at 110℃; for 48h; Schlenk technique;85%
butyl butyrate
109-21-7

butyl butyrate

para-bromotoluene
106-38-7

para-bromotoluene

1,1-di(p-tolyl)butan-1-ol
31067-10-4

1,1-di(p-tolyl)butan-1-ol

Conditions
ConditionsYield
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; Barbier Coupling Reaction; chemoselective reaction;83%
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; chemoselective reaction;83%
butyl butyrate
109-21-7

butyl butyrate

benzylamine
100-46-9

benzylamine

N-benzylbutyramide
10264-14-9

N-benzylbutyramide

Conditions
ConditionsYield
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium tert-butylate In toluene at 120℃; for 48h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;82%
butyl butyrate
109-21-7

butyl butyrate

aniline
62-53-3

aniline

N-phenylbutyramide
1129-50-6

N-phenylbutyramide

Conditions
ConditionsYield
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium tert-butylate In toluene at 120℃; for 48h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;80%

109-21-7Relevant articles and documents

Highly efficient self-esterification of aliphatic alcohols using supported gold nanoparticles under mild conditions

Wang, Fan,Xiao, Qi,Han, Pengfei,Sarina, Sarina,Zhu, Huaiyong

, p. 61 - 69 (2016)

Long aliphatic esters were prepared by the one-step catalytic self-esterification of primary alcohols using molecular oxygen as a green oxidant and supported gold nanoparticles (Au NPs) as catalyst. This heterogeneous catalyst achieved high activity and selectivity in a wide range of less reactive straight-chain alcohols (C4-C12) at atmospheric pressure O2 and near ambient temperature (45?°C). Under optimised conditions, the catalyst with Au loading of 3?wt% achieved the highest catalytic activity and selectivity. The AuNP catalysts are efficient and readily recyclable. The finding of this study may inspire further studies on new efficient catalytic systems for a wide range of organic syntheses using supported AuNP catalysts.

Lipase-catalyzed reactions in ionic liquids.

Madeira Lau,van Rantwijk,Seddon,Sheldon

, p. 4189 - 4191 (2000)

[reaction:see text] Candida antarctica lipase was shown to catalyze alcoholysis, ammoniolysis, and perhydrolysis reactions using the ionic liquids 1-butyl-3-methylimidazolium tetrafluoroborate or hexafluorophosphate as reaction media. Reaction rates were generally comparable with, or better than, those observed in organic media.

A quantitative comparison between conventional and bio-derived solvents from citrus waste in esterification and amidation kinetic studies

Clark, James H.,MacQuarrie, Duncan J.,Sherwood, James

, p. 90 - 93 (2012)

(R)-(+)-Limonene, which is available in large quantities from citrus waste, and its close derivative p-cymene are shown herein to be viable yet sustainable solvents for amidation and esterification reactions.

Use of salt hydrates to buffer optimal water level during lipase catalysed in synthesis in organic media: A practical procedure for organic chemists

Kvittingen, Lise,Sjursnes, Birte,Anthonsen, Thorleif,Halling, Peter

, p. 2793 - 2802 (1992)

Enzyme catalyzed reactions in mainly organic media depend very much on the amount of water in the system. We have shown that addition of appropriate solid salt hydrates to the reaction mixture is a simple and convenient method to obtain optimal water level conditions throughout the reaction. As a model reaction the esterification of butanoic acid with butanol catalysed by lipase from Candida rugosa was chosen. Variations in the amount of enzyme, in the solvent and in the concentration of reactants were made.

Genome Mining of Oxidation Modules in trans-Acyltransferase Polyketide Synthases Reveals a Culturable Source for Lobatamides

Ueoka, Reiko,Meoded, Roy A.,Gran-Scheuch, Alejandro,Bhushan, Agneya,Fraaije, Marco W.,Piel, J?rn

, p. 7761 - 7765 (2020)

Bacterial trans-acyltransferase polyketide synthases (trans-AT PKSs) are multimodular megaenzymes that biosynthesize many bioactive natural products. They contain a remarkable range of domains and module types that introduce different substituents into growing polyketide chains. As one such modification, we recently reported Baeyer–Villiger-type oxygen insertion into nascent polyketide backbones, thereby generating malonyl thioester intermediates. In this work, genome mining focusing on architecturally diverse oxidation modules in trans-AT PKSs led us to the culturable plant symbiont Gynuella sunshinyii, which harbors two distinct modules in one orphan PKS. The PKS product was revealed to be lobatamide A, a potent cytotoxin previously only known from a marine tunicate. Biochemical studies show that one module generates glycolyl thioester intermediates, while the other is proposed to be involved in oxime formation. The data suggest varied roles of oxygenation modules in the biosynthesis of polyketide scaffolds and support the importance of trans-AT PKSs in the specialized metabolism of symbiotic bacteria.

Dunbar

, p. 244 (1938)

Saegusa et al.

, p. 1960,1961 (1967)

Crystal structure, thermal decomposition mechanism and catalytic performance of hexaaquaaluminum methanesulfonate

Wang, Rui,Li, Rongrong,Jiang, Heng,Gong, Hong,Bi, Yanfeng

, p. 1327 - 1338 (2017)

Hexaaquaaluminum methanesulfonate crystals, [Al(H2O)6][CH3SO3]3 were synthesized by a hydrothermal reaction of Al(OH)3 with methanesulfonic acid. Single-crystal diffraction determination revealed that Al3+ was coordinated by six water molecules in octahedral geometry, while the CH3SO3 – anion connected with Al3+ through coordinated water molecules by hydrogen bonds. The six-coordinate environment of Al was also determined by 27Al MAS NMR measurement. Thermogravimetric analysis and Fourier transform infrared spectroscopy showed that the decomposition intermediate at 265–365?°C was Al2(μ-OH)(CH3SO3)5 and the final product was amorphous Al2O3 residue with about 0.8 wt% SO3 at 520–800?°C. A pure phase of [Al(H2O)6][CH3SO3]3 was confirmed by powder X-ray diffraction analysis. Esterification of n-butyric acid with n-butanol and ketalization of cyclohexanone with glycol catalyzed by [Al(H2O)6][CH3SO3]3 and Al2(μ-OH)(CH3SO3)5, respectively, proceeded in 100% yield by continuously removing the produced water. In the case of tetrahydropyranylation of n-butanol at room temperature in dichloromethane, the catalytic activity of [Al(H2O)6][CH3SO3]3 was much lower than that of Al2(μ-OH)(CH3SO3)5. Furthermore, both [Al(H2O)6][CH3SO3]3 precursor and Al2(μ-OH)(CH3SO3)5 catalysts could be recycled.

Homoleptic lanthanide amides as homogeneous catalyst for the Tishchenko reaction

Berberich, Helga,Roesky, Peter W.

, p. 1569 - 1571 (1998)

Known for about 25 years, the bis(trimethylsilyl)amides of Group 3 metals and lanthanides, M[N(SiMe3)2]3, are well suited as highly efficient catalysts for the dimerization of aldehydes [Tishchenko reaction, Eq. (1)].

Self-Condensation of n-Butyraldehyde over Solid Base Catalysts

Tsuji, Hideto,Yagi, Fuyuki,Hattori, Hideshi,Kita, Hideaki

, p. 759 - 770 (1994)

The catalytic properties of various solid bases for self-condensation of n-butyraldehyde in liquid phase were studied to elucidation the factors governing the activity and selectivity.For alkaline earth oxide catalysts and γ-alumina catalyst, aldol condensation ocurred, followed by Tishchenko-type cross-esterification of n-butyraldehyde with the dimer produced by the aldol condensation to form trimeric glycol ester.Alkali ion-modified alumina catalysts exhibited a high selectivity for the aldol condensation dimer, the trimeric glycol ester being formed little.Both basic and acidic sites on the surfaces of the alkaline earth oxides and γ-alumina were assumed to contribute to Tishchenko-type cross-esterification.The suppression of Tischenko-type cross-esterification.The suppression of Tischenko-type cross-esterification for alkali ion-modified alumina catalysts is due to the absence of acidic sites on the surfaces.The catalytic performances of alumina-supported magnesium oxide exhibited lower activity but higher selectivity to trimeric glycol ester than MgO.This catalytic feature was caused by the lower basicity and higher acidity on the surface of alumina-supported magnesium oxide as compared with MgO.The activity of alkali ion-exchanged zeolites was lowest among the catalysts examined in this study.The modification of zeolites with excess alkali ions improved the activity.

Facile Ester Synthesis on Ag-Modified Nanoporous Au: Oxidative Coupling of Ethanol and 1-Butanol Under UHV Conditions

Stowers, Kara J.,Madix, Robert J.,Biener, Monika M.,Biener, Juergen,Friend, Cynthia M.

, p. 1217 - 1223 (2015)

A dilute Ag alloy of nanoporous Au (npAu) has been shown to self-couple methanol with 100 % selectivity and high conversion under catalytic flow conditions. However, because prior studies in flow reactors showed difficulty in self-coupling ethanol and 1-butanol over npAu in flow reactors, the inherent capability on npAu for self-coupling of ethanol and 1-butanol was examined under ultrahigh vacuum conditions on identical npAu catalysts. This study shows that the oxygen-covered Ag-modified npAu does efficiently effect the self-coupling of ethanol and 1-butanol under UHV conditions. The coupling is initiated by adsorbed atomic oxygen formed from O2 dissociation via a chemisorbed molecular state. The amount of ester formed increases with the degree of oxygen precoverage at the expense of aldehyde production. Repeated annealing of the catalyst above 550 K for temperature programmed reaction changes the ligament and pore sizes, affecting the product distribution, but high reactivity is sustained over many heating cycles. (Figure Presented).

SELENOESTERS IN ORGANIC SYNTHESIS. 1. CONVERSION OF MIXED CARBOXYLIC ACID ESTERS TO SELENOESTERS

Sviridov, A. F.,Ermolenko, M. S.,Yashunskii, D. V.,Kochetkov, N. K.

, p. 1509 - 1513 (1985)

-

Organoaluminum cations for carbonyl activation

Kannan, Ramkumar,Chambenahalli, Raju,Kumar, Sandeep,Krishna, Athul,Andrews, Alex P.,Jemmis, Eluvathingal D.,Venugopal, Ajay

, p. 14629 - 14632 (2019)

In search of stable, yet reactive aluminum Lewis acids, we have isolated an organoaluminum cation, [(Me2NC6H4)2Al(C4H8O)2]+, coordinated with two labile tetrahydrofuran ligands. Its catalytic performance in aldehyde dimerization reveals turn-over frequencies reaching up to 6000 h-1, exceeding that of the reported main group catalysts. The cation is further demonstrated to catalyze hydroelementation of ketones. Mechanistic investigations reveal that aldehyde dimerization and ketone hydrosilylation occur through carbonyl activation.

Deuterium kinetic isotopic study for hydrogenolysis of ethyl butyrate

Gnanamani, Muthu Kumaran,Jacobs, Gary,Keogh, Robert A.,Davis, Burtron H.

, p. 27 - 35 (2011)

The hydrogenation of ethyl butyrate, n-butyric acid, and n-butyraldehyde to their corresponding alcohol(s) has been studied over a γ-Al 2O3-supported cobalt catalyst using a high-pressure fixed-bed reactor in the temperature range of 473-493 K. H2-D 2-H2 switching experiments show that ethyl butyrate and n-butyric acid follow an inverse kinetic isotope effect (KIE) (i.e. r H/rD = 0.50-0.54), whereas n-butyraldehyde did not display any KIE (i.e. rH/rD = 0.98). DRIFTS experiments were performed over the support and catalyst to monitor the surface species formed during the adsorption of ethyl butyrate and n-butyric acid at atmospheric pressure and the desired temperature. Butanoate and butanoyl species are the stable surface intermediates formed during hydrogenation of ethyl butyrate. Hydrogenation of butanoate to a partially hydrogenated intermediate is likely involved in the rate-determining step of ethyl butyrate and butyric acid hydrogenation.

Ruthenium PNN(O) Complexes: Cooperative Reactivity and Application as Catalysts for Acceptorless Dehydrogenative Coupling Reactions

De Boer, Sandra Y.,Korstanje, Ties J.,La Rooij, Stefan R.,Kox, Rogier,Reek, Joost N. H.,Van Der Vlugt, Jarl Ivar

, p. 1541 - 1549 (2017)

The novel tridentate PNNOH pincer ligand LH features a reactive 2-hydroxypyridine functionality as well as a bipyridyl-methylphosphine skeleton for meridional coordination. This proton-responsive ligand coordinates in a straightforward manner to RuCl(CO)(H)(PPh3)3 to generate complex 1. The methoxy-protected analogue LMe was also coordinated to Ru(II) for comparison. Both species have been crystallographically characterized. Site-selective deprotonation of the 2-hydroxypyridine functionality to give 1′ was achieved using both mild (DBU) and strong bases (KOtBu and KHMDS), with no sign of involvement of the phosphinomethyl side arm that was previously established as the reactive fragment. Complex 1′ is catalytically active in the dehydrogenation of formic acid to generate CO-free hydrogen in three consecutive runs as well as for the dehydrogenative coupling of alcohols, giving high conversions to different esters and outperforming structurally related PNN ligands lacking the NOH fragment. DFT calculations suggest more favorable release of H2 through reversible reactivity of the hydroxypyridine functionality relative to the phosphinomethyl side arm.

Acceptorless dehydrogenative coupling of alcohols catalysed by ruthenium PNP complexes: Influence of catalyst structure and of hydrogen mass transfer

Zhang, Lei,Raffa, Guillaume,Nguyen, Duc Hanh,Swesi, Youssef,Corbel-Demailly, Louis,Capet, Frédéric,Trivelli, Xavier,Desset, Simon,Paul, Sébastien,Paul, Jean-Fran?ois,Fongarland, Pascal,Dumeignil, Franck,Gauvin, Régis M.

, p. 331 - 343 (2016)

Base-free catalytic acceptorless dehydrogenative homo-coupling of alcohols to esters under neat conditions was investigated using a combined organometallic synthesis and kinetic modelling approach. The considered bifunctional ruthenium aliphatic PNP complexes are very active, affording TONs up to 15,000. Notably, gas mass transfer issues were identified, which allowed us to rationalize previous observations. Indeed, the reaction kinetics are limited by the rate of transfer from the liquid phase to the gas phase of the hydrogen co-produced in the reaction. Mechanistically speaking, this relates to the interconverting couple amido monohydride/amino bishydride. Overcoming this by switching into the chemical regime leads to an initial turnover frequency increase from about 2000 up to 6100?h?1. This has a significant impact when considering assessment of novel or reported catalytic systems in this type of reaction, as overlooking of these engineering aspects can be misleading.

Tuning acidity in zirconium-based metal organic frameworks catalysts for enhanced production of butyl butyrate

Jrad, Asmaa,Abu Tarboush, Belal J.,Hmadeh, Mohamad,Ahmad, Mohammad

, p. 31 - 41 (2019)

Three isostructural zirconium-based metal organic frameworks (MOFs), UiO-66, UiO-66(COOH)2 and UiO-66(NH2) were synthesized, fully characterized and efficiently used as active and recyclable catalysts for the esterification reaction of butyric acid to produce a green fuel additive, butyl butyrate. The catalytic activities of the used structures were comparable, and mostly better, than other heterogeneous acid catalyst reported in the literature. Moreover, 90% conversion was achieved by employing the most acidic member, UiO-66(COOH)2, which is close to the 95% conversion obtained by the conventional liquid catalyst H2SO4. Using the synthesized MOFs, large variations in the conversion to butyl butyrate were obtained which was the base of a detailed investigation on the origin of their catalytic activities. The analysis of the TGA results helped estimate the number of structural defects in each studied MOF. Interestingly, it was concluded that, for the MOFs with different organic linkers, the catalytic activity was not directly related to the number of defects. Further analysis was done to investigate the alternative parameters that could be behind this difference in catalytic activity, and the parameters included but were not limited to the surface area of the MOFs, their particle size, the linkers’ active sites, and their accessibility through effective mass transfer. Although a combination of these factors were found to contribute to the superior catalytic activity of UiO-66(COOH)2, however, its exceptional conversion was mainly attributed to the effect of the additional active acid functional groups grafted onto its organic linker, along with its smaller particle size which allowed for better mass transfer and accessibility of the active site Furthermore, two kinetic models were successfully developed and used to determine the different kinetic parameters of the esterification reaction and to study their dependence on the different characteristics of the MOFs. With this knowledge, catalytic activity of MOFs can be engineered from a laboratory prototype and optimized by tuning the functional groups of the organic linkers to serve as effective catalysts for the production of fine chemicals such as biofuels.

An antimony(V) substituted Keggin heteropolyacid, H4PSbMo 11O40: Why is its catalytic activity in oxidation reactions so different from that of H4PVMo11O 40?

Goldberg, Hila,Kumar, Devesh,Sastry, G. Narahari,Leitus, Gregory,Neumann, Ronny

, p. 152 - 157 (2012)

An antimony(V) containing α-Keggin type acidic polyoxometalate, H4PSbMo11O40, was prepared by reacting NaMoO4, H3PO4 and Sb2O3 in the presence of aqua regia to appraise its reactivity compared to the well known vanadate analog, H4PVMo11O40. Characterization was by X-ray diffraction, MALDI-TOF MS, IR, UV-vis and 31P NMR spectroscopy. Catalytic redox reactions, such as oxidative dehydrogenation using O2 and N2O as terminal oxidants were studied and showed very different reactivity of H4PSbMo 11O40 versus H4PVMo11O40. It was found by DFT calculations that in contrast to analogous H 4PVMo11O40 where vanadium centered catalysis is observed, in H4PSbMo11O40 catalysis is molybdenum and not antimony centered.

Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone

Kakasi-Zsurka, Sandor,Todea, Anamaria,But, Andrada,Paul, Cristina,Boeriu, Carmen G.,Davidescu, Corneliu,Nagy, Lajos,Kuki, Akos,Keki, Sandor,Peter, Francisc

, p. 22 - 28 (2011)

Lipase-catalyzed reaction of 3-hydroxybutyric acid with d-glucono-δ-lactone at 5:1 molar ratio and 80°C yielded a mixture of moderate molecular weight linear and cyclic oligomers. The most efficient biocatalyst, Candida antarctica B lipase (Novozyme 435), allowed the synthesis of new oligomeric compounds with ring-opened gluconolactone units included in the oligomeric chain, without previous derivatization of the sugar, or activation of the acid monomer. The reaction medium nature had an important influence on the product composition. Although the main copolymer amount was synthesized in tert-butanol/dimethylsulfoxide medium, the highest polymerization degrees, up to 9 for the copolymer, and 10 for the 3-hydroxybutyric acid homopolymer co-product, were achieved in solventless conditions.

Efficient dimeric esterification of alcohols with NBS in water using l-proline as catalyst

Liu, Xiuhong,Wu, Jun,Shang, Zhicai

, p. 75 - 83 (2012)

The L-proline-catalyzed oxidation of aliphatic primary alcohols with N-bromosuccimide (NBS) in water at room temperature to afford the corresponding dimeric esters in good to excellent yields was described. This pathway of dimeric esterification was proved to be very simple and environmentally friendly.

Buffer-mediated activation of Candida antarctica lipase B dissolved in hydroxyl-functionalized ionic liquids

Ou, Guangnan,Yang, Jing,He, Biyan,Yuan, Youzhu

, p. 66 - 70 (2011)

Ionic-liquid buffer having phosphate anion was synthesized for the development of buffered enzymatic ionic liquid systems. Both the conformation and transesterification activity of Candida antarctica lipase B (CALB) dissolved in the hydroxyl-functionalized ionic liquids were buffer dependent. Intrinsic fluorescence studies indicated that the CALB possessed a more compact conformation in the medium consisted of ionic liquid buffer having phosphate anion and hydroxyl-functionalized ionic liquids like 1-(1-hydroxyethyl)-3- methyl-imidazolium tetrafluoroborate and 1-(1-hydroxyethyl)-3-methyl-imidazolium nitrate. High activity and outstanding stability could be obtained with the CALB enzyme in the buffered ionic liquids for the transesterification.

One-step solvent-free aerobic oxidation of aliphatic alcohols to esters using a tandem Sc-Ru?MOF catalyst

Feng, Tingkai,Li, Conger,Li, Tao,Zhang, Songwei

, p. 1474 - 1480 (2022/03/08)

Esters are an important class of chemicals in industry. Traditionally, ester production is a multi-step process involving the use of corrosive acids or acid derivatives (e.g. acid chloride, anhydride, etc.). Therefore, the development of a green synthetic protocol is highly desirable. This work reports the development of a metal-organic framework (MOF) supported tandem catalyst that can achieve direct alcohol to ester conversion (DAEC) using oxygen as the sole oxidizing agent under strictly solvent-free conditions. By incorporating Ru nanoparticles (NPs) along with a homogeneous Lewis acid catalyst, scandium triflate, into the nanocavities of a Zr MOF, MOF-808, the compound catalyst, Sc-Ru?MOF-808, can achieve aliphatic alcohol conversion up to 92% with ester selectivity up to 91%. A mechanistic study reveals a unique “via acetal” pathway in which the alcohol is first oxidized on Ru NPs and rapidly converted to an acetal on Sc(iii) sites. Then, the acetal slowly decomposes to release an aldehyde in a controlled manner for subsequent oxidation and esterification to the ester product. To the best of our knowledge, this is the first example of DAEC of aliphatic alcohols under solvent-free conditions with high conversion and ester selectivity.

Dual utility of a single diphosphine-ruthenium complex: A precursor for new complexes and, a pre-catalyst for transfer-hydrogenation and Oppenauer oxidation

Mukherjee, Aparajita,Bhattacharya, Samaresh

, p. 15617 - 15631 (2021/05/19)

The diphosphine-ruthenium complex, [Ru(dppbz)(CO)2Cl2] (dppbz = 1,2-bis(diphenylphosphino)benzene), where the two carbonyls are mutually cis and the two chlorides are trans, has been found to serve as an efficient precursor for the synthesis of new complexes. In [Ru(dppbz)(CO)2Cl2] one of the two carbonyls undergoes facile displacement by neutral monodentate ligands (L) to afford complexes of the type [Ru(dppbz)(CO)(L)Cl2] (L = acetonitrile, 4-picoline and dimethyl sulfoxide). Both the carbonyls in [Ru(dppbz)(CO)2Cl2] are displaced on reaction with another equivalent of dppbz to afford [Ru(dppbz)2Cl2]. The two carbonyls and the two chlorides in [Ru(dppbz)(CO)2Cl2] could be displaced together by chelating mono-anionic bidentate ligands, viz. anions derived from 8-hydroxyquinoline (Hq) and 2-picolinic acid (Hpic) via loss of a proton, to afford the mixed-tris complexes [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], respectively. The molecular structures of four selected complexes, viz. [Ru(dppbz)(CO)(dmso)Cl2], [Ru(dppbz)2Cl2], [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], have been determined by X-ray crystallography. In dichloromethane solution, all the complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows redox responses within 0.71 to -1.24 V vs. SCE. [Ru(dppbz)(CO)2Cl2] has been found to serve as an excellent pre-catalyst for catalytic transfer-hydrogenation and Oppenauer oxidation.

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