123-86-4

Basic information

• Product Name: Butyl acetate
• Synonyms: acetatedebutyle(french);Butile;Butile(acetati di);butile(acetatidi);Butyl ester of acetic acid;Butyl ester, acetic acid;Butylacetat;Butylacetaten
• CAS NO: 123-86-4
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• EINECS: 204-658-1
• Product Categories: Pharmaceutical Intermediates;Organics;Analytical Chemistry;Solvents for HPLC & Spectrophotometry;Solvents for Spectrophotometry;ReagentPlus(R) Solvent Grade ProductsSaturated fatty acids and derivatives;ReagentPlus(R)Semi-Bulk Solvents;ReagentPlus(R)Solvents;Biotech SolventsSolvents;A-B;A-BFlavors and Fragrances;Alphabetical Listings;Certified Natural Products;Flavors and Fragrances;A-BSaturated fatty acids and derivatives;Alcohol AcetatesAlphabetic;Alpha Sort;B;BI - BZAnalytical Standards;Chemical Class;EstersAnalytical Standards;Solvents;Volatiles/ Semivolatiles;A-B, Puriss p.a.Saturated fatty acids and derivatives;Analytical Reagents for General Use;Puriss p.a.;Alcohol AcetatesSolvents;Anhydrous Grade SolventsSolvents;Solvent Bottles;Sure/Seal? Bottles;ACS Grade SolventsSaturated fatty acids and derivatives;ACS GradeSemi-Bulk Solvents;ACS GradeSolvents;Alcohol Acetates;Carbon Steel Cans with NPT Threads;Alcohol AcetatesSolvent Bottles;CHROMASOLV
• Mol File: 123-86-4.mol

Chemical Properties

• Melting Point: −78 °C(lit.)
• Boiling Point: 124-126 °C(lit.)
• Flash Point: 74 °F
• Appearance: ≤10(APHA)/Liquid
• Density: 0.88 g/mL at 25 °C(lit.)
• Vapor Density: 4 (vs air)
• Vapor Pressure: 15 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.394(lit.)
• Storage Temp.: Flammables area
• Solubility: 5.3g/l
• Explosive Limit: 1.4-7.5%(V)
• Water Solubility: 0.7 g/100 mL (20 ºC)
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, strong bases.
• Merck: 14,1535
• BRN: 1741921
• CAS DataBase Reference: Butyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Butyl acetate(123-86-4)
• EPA Substance Registry System: Butyl acetate(123-86-4)

Safety Data

• Statements: 10-66-67-R67-R66-R10
• Safety Statements: 25-S25
• RIDADR: UN 1123 3/PG 3
• WGK Germany: 1
• RTECS: AF7350000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 123-86-4(Hazardous Substances Data)

Usage

Chemical Properties

Butyl acetate is a colorless or yellowish liquid with a strong fruity odor. burning and then sweet taste reminiscent of pineapple. It occurs in many fruits and is a constituent of apple aromas. Butyl acetate is incompatible with strong oxidizing agents, strong acids, and strong bases. There are 4 isomers. At 20 °C, the density of the n-butyl isomer is 0.8825 g/ cm3, and the density of the sec-isomer is 0.8758 g/cm3 (Bisesi, 1994). The n-butyl isomer is soluble in most hydrocarbons and acetone, and it is miscible with ethanol, ethyl ether, and chloroform (Haynes, 2010). It dissolves many plastics and resins (NIOSH, 1981).

Physical properties

Clear, colorless liquid with a strong fruity odor resembling bananas. Sweetish taste as low concentrations (<30 μg/L). Experimentally determined detection and recognition odor threshold concentrations were 30 μg/m3 (6.3 ppbv) and 18 μg/m3 (38 ppbv), respectively (Hellman and Small, 1974). Cometto-Mu?iz et al. (2000) reported nasal pungency threshold concentrations ranged from approximately 550 to 3,500 ppm.

Occurrence

Reported present in rum ether, pears, pear brandy, cider, mango, mountain papaya (C. pubescens), soybean, roasted peanuts and honey and other natural products.

Uses

Different sources of media describe the Uses of 123-86-4 differently. You can refer to the following data:
1. n-Butyl acetate is used in the manufactureof lacquers, plastics, photographic films, andartificial leathers.
2. Butyl acetate is one of the more important derivatives of n-butyl alcohol produced commercially, is employed as a solvent in rapid drying paints and coatings. In some instances, butyl acetate, C6H12O2, has replaced ethoxyethyl acetate due to the latter’s reported toxicity and teratogenicity.
3. Butyl Acetate is a flavoring agent which is a clear, colorless liquid possessing a fruity and strong odor. it is sparingly soluble in water and miscible in alcohol, ether, and propylene glycol. it is also termed n-butyl acetate.

Definition

ChEBI: The acetate ester of butanol.

Production Methods

Butyl alcohol is combined with acetic acid in the presence of a catalyst such as sulfuric acid. After esterification is complete, the solution is distilled to yield butyl acetate .

Preparation

By esterification of n-butyl alcohol with acetic acid.

Aroma threshold values

Detection: 10 to 500 ppb

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 5265, 1951 DOI: 10.1021/ja01155a075The Journal of Organic Chemistry, 39, p. 3728, 1974 DOI: 10.1021/jo00939a026

General Description

A clear colorless liquid with a fruity odor. Flash point 72 - 88°F. Density 7.4 lb / gal (less than water). Hence floats on water. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Very slightly soluble in water.

Reactivity Profile

Butyl acetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Attacks many plastics. [Handling Chemicals Safely 1980. p. 233].

Hazard

Skin irritant, toxic. Flammable, moderate fire risk. Eye and upper respiratory tract irritant.

Health Hazard

Different sources of media describe the Health Hazard of 123-86-4 differently. You can refer to the following data:
1. Exposures to n-butyl acetate cause harmful effects that include, but are not limited to, coughing and shortness of breath. High concentrations have a narcotic effect, with symp toms such as sore throat, abdominal pain, nausea, vomiting, and diarrhea. High concen trations of n-butyl acetate cause severe poisoning. Prolonged periods of exposure cause adverse effects to the lungs, the nervous system, and the mucous membranes. Repeated skin contact causes skin dryness or cracking, and dermatitis.
2. The narcotic effects of n-butyl acetate isgreater than the lower alkyl esters of aceticacid. Also, the toxicities and irritant actionsare somewhat greater than n-propyl, iso propyl, and ethyl acetates. Exposure to its vapors at about 2000 ppm caused mild irritation of the eyes and salivation in test animals. A 4-hour exposure to 14,000 ppm wasfatal to guinea pigs. In humans, inhalation of 300-400 ppm of n-butyl acetate may produce moderate irritation of the eyes and throat, and headache.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Flammable

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Biochem/physiol Actions

Taste at 30 ppm

Safety Profile

Moderately toxic by intraperitoneal route. Mdly toxic by inhalation and ingestion. An experimental teratogen. A skin and severe eye irritant. Human systemic effects by inhalation: conjunctiva irritation, unspecified nasal and respiratory system effects. A mild allergen. High concentrations are irritating to eyes and respiratory tract and cause narcosis. Evidence of chronic systemic toxicity is inconclusive. Flammable liquid. Moderately explosive when exposed to flame. Ignites on contact with potassium tert-butoxide. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid and irritating fumes. See also ESTERS.

Carcinogenicity

There are no indications of mutagenic or cytogenic effects for n-butyl acetate.

Source

Identified as a volatile constituent released by fresh coffee beans (Coffea canephora variety Robusta) at different stages of ripeness (Mathieu et al., 1998). Also identified among 139 volatile compounds identified in cantaloupe (Cucumis melo var. reticulates cv. Sol Real) using an automated rapid headspace solid phase microextraction method (Beaulieu and Grimm, 2001).

Environmental fate

Biological. Heukelekian and Rand (1955) reported a 5-d BOD value of 0.52 g/g which is 23.5% of the ThOD value of 2.21 g/g. Photolytic. Butyl acetate reacts with OH radicals in the atmosphere at a rate constant of 4.15 x 10-12 cm3/molecule?sec at 296 K (Wallington et al., 1988b). Chemical/Physical. Hydrolyzes in water forming 1-butanol and acetic acid. Estimated hydrolysis half-lives at 20 °C: 11.4 d at pH 9.0, 114 d at pH 8.0, and 3.1 yr at pH 7.0 (Mabey and Mill, 1978). At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 154 mg/L. The adsorbability of the carbon was 169 mg/g carbon (Guisti et al., 1974).

storage

n-Butyl acetate should be kept stored in a segregated and approved area. Workers should keep the container in a cool, well-ventilated area, closed tightly, and sealed until ready for use. Workers should avoid all possible sources of ignition/spark at the workplace

Purification Methods

Distil, reflux with successive small portions of KMnO4 until the colour persists, dry with anhydrous CaSO4, filter and redistil. [Beilstein 2 IV 143.]

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Precautions

On exposure to Butyl acetate, immediately wash with plenty of water, also under the eyelids, for at least 15 min. Remove contact lenses. Butyl acetate?is flammable in the pres ence of open flames, sparks, oxidizing materials, acids, and alkalis. It poses explosion risk in the presence of mechanical impact. For health safety, management authorities should provide exhaust ventilation facilities at the workplace to keep the airborne concentrations of vapors of Butyl acetate?below TLV.

InChI:InChI=1/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3

Synthetic route

acetic acid (64-19-7) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With crosslinked sulphonated polystyrene at 80℃; for 2h; Product distribution; other acids and solvents; var. catalysts, temp. and time;	100%
zirconium(IV) oxide for 2h; Heating;	100%
phosphomolybdic acid hydrate at 65 - 70℃; for 1h; Product distribution; Further Variations:; Catalysts; Reaction partners;	100%

sec-Butyl acetate (105-46-4) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4) + iso-butanol (78-92-2, 15892-23-6)

Conditions	Yield
With water; sodium butanolate at 30℃; for 0.0833333h; carried out in a reaction-distillation unit, industrial preparation;	A n/a B 100%

acetic anhydride (108-24-7) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With N-methylmorpholinium propanesulfonic acid ammonium hydrogensulfate at 25℃; for 0.0333333h; Inert atmosphere; neat (no solvent); chemoselective reaction;	99%
With SBA-15-Ph-Pr-SO3H at 20℃; for 0.05h;	99%
With sulfonic group functionalized polyacrylonitrile preoxidated nanofiber mat at 60℃; for 3h;	99.58%

Reaxys ID: 11464599 → acetic acid butyl ester (123-86-4)

Conditions	Yield
at 105℃;	99.1%
With hydrogen at 95.5℃;	99.1%
at 102℃;	95%
With hydrogen at 95.5℃; under 6750.68 Torr;	94%

ethyl acetate (141-78-6) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With 2C18H22N4*Zn(2+)*2C2F3O2(1-) for 18h;	99%
With K5 for 2h; Heating;	92%
With tin(IV) oxide at 200℃; further conditions: liquid phase, reflux;	82%

vinyl acetate (108-05-4) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With pseudomonas fuorescens lipase immobilized on multiwall carbon nano-tubes at 50℃; for 4.5h; Green chemistry;	99%
With porcine pancreatic lipase In tetrahydrofuran for 48h; Ambient temperature; Yield given;
With steapsin lipase In hexane at 55℃; for 24h; Enzymatic reaction;	99 %Chromat.

acetic acid (64-19-7) + butyloxy(diphenyl)-λ6-sulfanenitrile (143885-04-5) → acetic acid butyl ester (123-86-4) + S,S-diphenylsulphoximine (22731-83-5)

Conditions	Yield
With hydrogenchloride In chloroform-d1 at 20℃; for 0.25h;	A 99% B n/a

Reaxys ID: 11465424 → acetic acid butyl ester (123-86-4)

Conditions	Yield
at 95.5℃;	98.8%

1-bromo-butane (109-65-9) + potassium acetate (127-08-2) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With tetrabutylammomium bromide In neat (no solvent) at 60℃; for 2h;	98%
Aliquat 336 for 20h; Ambient temperature;	93%
PEG-400; silica gel In toluene for 3h; Heating; var. catalysts;	56%
With aluminum oxide 1.) water, 2.) 85 deg C, 20 h;	50%
With 18-crown-6-based covalent organic framework In acetonitrile at 85℃; for 5h;	85 %Chromat.

phosphoric acid tributyl ester (126-73-8) + sodium acetate (127-09-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
at 200 - 220℃; for 5h;	96%
Heating;

acetyl chloride (75-36-5) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
zirconium(IV) oxychloride at 20℃; for 0.0333333h;	95%
With zinc(II) oxide at 20℃; for 0.25h;	95%
bismuth(III) oxychloride at 20℃; for 0.0333333h;	95%

Phenyl acetate (122-79-2) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With 2Zn(2+)*C20H14N4*4C2H3O2(1-)*1.5CH4O In neat (no solvent) at 50℃; for 18h; Temperature; Reagent/catalyst; Solvent;	95%
With acetic acid for 0.166667h; Microwave irradiation; neat (no solvent);
With C21H31N2O12Zn2(1+)*2H2O*C2H3O2(1-) at 50℃; for 20h; Reagent/catalyst; Sealed tube;	68 %Chromat.

Allyl acetate (591-87-7) → acetic acid butyl ester (123-86-4)

Conditions	Yield
at 102℃;	93%

acetic anhydride (108-24-7) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4) + dimethylglyoxal (431-03-8)

Conditions	Yield
With cobalt(II) chloride In acetonitrile at 25℃; for 2h; other primary and secondary alcohols, other temperature;	A 92% B n/a
With cobalt(II) chloride In acetonitrile at 25℃; for 2h;	A 92% B n/a

1-bromo-butane (109-65-9) + acetic acid (64-19-7) → acetic acid butyl ester (123-86-4)

Conditions	Yield
In neat (no solvent) at 20℃; for 0.666667h;	92%
With tetradecyl(trihexyl)phosphonium bistriflamide; potassium carbonate at 70℃; for 6h;	74%
Stage #1: acetic acid With tetradecyl(trihexyl)phosphonium bistriflimide; potassium carbonate at 70℃; for 0.5h; Stage #2: 1-bromo-butane at 70℃; for 6h;	74%
With ISOPROPYLAMIDE; tetra(n-butyl)ammonium hydroxide at 100℃; for 1h; 1) pH 10 - 12;
With tetraethylammonium tosylate In N,N-dimethyl-formamide Ambient temperature; electrolysis;	60 % Chromat.

acetylacetone (123-54-6) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With iron(III) chloride; ammonium persulfate In tetrachloromethane; 1,2-dichloro-ethane at 120℃; for 15h;	92%

1-Acetyl-4(1H)-pyridinon (30074-98-7) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
In dichloromethane at 20℃; for 12h;	91%

-butyl vinyl ether (111-34-2) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With oxygen; Pd2060(NO3)360(OAc)360O80; titanium(IV) oxide In N,N-dimethyl acetamide; water at 80℃; for 2h; Wacker oxidation;	91%
With bis-triphenylphosphine-palladium(II) chloride; dihydrogen peroxide; triethylamine In N,N-dimethyl acetamide; water at 60℃; for 1h;	72 %Chromat.
With bis-triphenylphosphine-palladium(II) chloride; dihydrogen peroxide; triethylamine In N,N-dimethyl acetamide; water at 60℃; for 1h; Green chemistry;	72 %Chromat.

1-bromo-butane (109-65-9) + sodium acetate (127-09-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With Aliquat 336 at 120℃;	90%
With polyethylene glycol 400 at 65 - 70℃; for 4h;	90%

1-iodo-butane (542-69-8) + sodium acetate (127-09-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With polyethylene glycol 400 at 65 - 70℃; for 2h;	90%

allyl n-butyl ether (3739-64-8) + acetyl chloride (75-36-5) → acetic acid butyl ester (123-86-4)

Conditions	Yield
cobalt(II) chloride In acetonitrile for 4h; Ambient temperature;	89%

allyl n-butyl ether (3739-64-8) + acetyl chloride (75-36-5) → acetic acid butyl ester (123-86-4) + dimethylglyoxal (431-03-8)

Conditions	Yield
CoCl2 In acetonitrile Ambient temperature; Yields of byproduct given;	A 89% B n/a

n-Butyl chloride (109-69-3) + sodium acetate (127-09-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With polyethylene glycol 400 at 65 - 70℃; for 5h;	89%

-butyl vinyl ether (111-34-2) + acetyl chloride (75-36-5) → n-butyl 1-chloroethyl ether (3450-47-3) + acetic acid butyl ester (123-86-4)

Conditions	Yield
CoCl2 In acetonitrile Ambient temperature;	A 10% B 85%

dibutyl ether (142-96-1) + acetic anhydride (108-24-7) → acetic acid butyl ester (123-86-4)

Conditions	Yield
FeCl3-Montmorillonite K-10 at 70℃; for 24h;	83%
With thallium(III) nitrate Ambient temperature;	57%
With sulfuric acid

benzyl 1-butyl ether (588-67-0) + acetyl chloride (75-36-5) → acetic acid butyl ester (123-86-4) + N-(phenylmethyl)acetamide (588-46-5) + benzyl chloride (100-44-7) + dimethylglyoxal (431-03-8)

Conditions	Yield
CoCl2 In acetonitrile Ambient temperature; Yields of byproduct given;	A 80% B 21% C 15% D n/a

-butyl vinyl ether (111-34-2) + acetyl chloride (75-36-5) → acetic acid butyl ester (123-86-4)

Conditions	Yield
cobalt(II) chloride In acetonitrile at 0℃; for 1h;	79%

Acetanilid (103-84-4) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With hydrogenchloride; iron(III) chloride hexahydrate In hexane; water at 80℃; for 14h;	79%

1-pentyl acetate (628-63-7) + butan-1-ol (71-36-3) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With diethylamine; lithium bromide at 20℃; for 24h; neat (no solvent);	78%
K2CO3 + 5percent Carbowax 6000 at 170℃;	58 % Chromat.

2-butoxytetrahydropyran (1927-68-0) + ethyl acetate (141-78-6) → acetic acid butyl ester (123-86-4)

Conditions	Yield
With indium (III) iodide for 14h; Heating;	78%

acetic acid butyl ester (123-86-4) + 4,4'-bis(carbomethoxy)-2,2'-bipyridine (71071-46-0) → 4,4′-bis(2-carboxyvinyl)-2,2'-bipyridine (773130-04-4)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; platinum on activated charcoal In tetrahydrofuran at 145℃; under 760.051 Torr; for 36h; Inert atmosphere;	98.5%

acetic acid butyl ester (123-86-4) + benzaldehyde (100-52-7) → (E)-3-(phenyl)acrylic acid butyl ester (52392-64-0)

Conditions	Yield
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 25℃; Inert atmosphere; stereoselective reaction;	98%

acetic acid butyl ester (123-86-4) → ethanol-1,1-d2 (1859-09-2)

Conditions	Yield
With lithium aluminium deuteride In diethyl ether	97%
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino]ruthenium(II); deuterium In neat (no solvent) at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox;

acetic acid butyl ester (123-86-4) → tetra(n-butoxy)silane (4766-57-8)

Conditions	Yield
With tetrabutoxytitanium; tetraethoxy orthosilicate Heating;	96%

acetic acid butyl ester (123-86-4) → ethanol (64-17-5)

Conditions	Yield
With (Ppyz)Zr(BH4)2Cl2 In diethyl ether for 4h; Heating;	95%
With sodium tetrahydroborate; [fac-8-(2-diphenylphosphinoethyl)amidotrihydroquinoline]RuH(PPh3)(CO); hydrogen In tetrahydrofuran at 120℃; under 38002.6 Torr; for 18h; Autoclave; Industrial scale;
With sodium tetrahydroborate; [fac-8-(2-diphenylphosphinoethyl)amidotrihydroquinoline]RuH(PPh)3(CO); hydrogen In tetrahydrofuran at 120℃; under 37503.8 Torr; for 18h; Inert atmosphere; Autoclave;

acetic acid butyl ester (123-86-4) → acetyl iodide (507-02-8) + trimethylsilyl acetate (2754-27-0)

Conditions	Yield
With trimethylsilyl iodide; iodine In chloroform-d1 at 50℃; for 2h;	A 6% B 94%

1-amino-3-methylbutane (107-85-7) + acetic acid butyl ester (123-86-4) → N-isopentylacetamide (13434-12-3)

Conditions	Yield
Stage #1: 1-amino-3-methylbutane With diisobutylaluminium hydride In tetrahydrofuran; toluene Stage #2: acetic acid butyl ester In tetrahydrofuran at 20℃; for 2h;	94%

acetic acid butyl ester (123-86-4) + 4-chloro-N-(1,1-dimethylprop-2-ynyl)benzamide (24911-15-7) → 2-(4-chloro-phenyl)-4,4-dimethyl-5-methylene-4,5-dihydrooxazole (247196-65-2)

Conditions	Yield
copper(I) chloride	94%
copper(I) chloride	94%

concentrated sodium hydroxide + acetic acid butyl ester (123-86-4) + (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]-N-(2-methylphenylsulphonyl)benzamide (136564-68-6) → 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxy-N-(2-methylphenylsulfonyl)benzamide

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water	94%

acetic acid butyl ester (123-86-4) + (E)-3-trimethylsilyl-2-propenal (58107-34-9, 64081-45-4, 33755-86-1) → butyl (E)-3-hydroxy-5-(trimethylsilyl)pent-4-enoate (128855-24-3)

Conditions	Yield
Stage #1: acetic acid butyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (E)-3-trimethylsilyl-2-propenal In tetrahydrofuran; hexane at -78℃; for 0.166667h;	93%
With lithium diisopropyl amide In tetrahydrofuran	77%

acetic acid butyl ester (123-86-4) + N-(α,α-dimethylpropargyl)-1-benzenecarboxamide (33244-86-9) → 4,4-dimethyl-5-methylene-2-phenyl-4,5-dihydrooxazole

Conditions	Yield
With silver nitrate	93%
With silver nitrate	93%

acetic acid butyl ester (123-86-4) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → (2,2-dimethyl-1,3-dioxolan-4-yl)methyl acetate (121348-86-5)

Conditions	Yield
With sodium methylate In methanol at 120℃; for 5h;	92.7%

acetic acid butyl ester (123-86-4) + benzylamine (100-46-9) → N-(phenylmethyl)acetamide (588-46-5)

Conditions	Yield
With Candida antarctica lipase B; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 60℃; for 24h; Molecular sieve; Ionic liquid; Enzymatic reaction;	92%
Stage #1: benzylamine With diisobutylaluminium hydride In tetrahydrofuran; toluene Stage #2: acetic acid butyl ester In tetrahydrofuran at 20℃; for 2h;	91%
Stage #1: benzylamine With [m-(1,4-diazabicyclo[2.2.2]octanekN1:kN4)]hexamethyldialuminum In tetrahydrofuran at 40℃; for 1h; Stage #2: acetic acid butyl ester In tetrahydrofuran for 18h; Heating;	70%

1,5-pentanedioic acid (110-94-1) + acetic acid butyl ester (123-86-4) → Pentanedioic acid dibutyl ester (6624-57-3) + Pentanedioic acid monobutyl ester (93504-86-0)

Conditions	Yield
With Dowex 50W-X2 (50-100 mesh) In octane at 70℃; for 7.33333h;	A 5% B 92%
With Dowex 50Wx2 In octane at 70℃; for 7.33333h; Esterification;	A 5% B 92%

acetic acid butyl ester (123-86-4) + 5-bromo-6-methoxy-2-acetylnaphthalene (84167-74-8) → 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

Conditions	Yield
With hydrogenchloride; sodium methylate In water	92%
With hydrogenchloride; sodium methylate In water	92%

Upstream product

• 123-91-1 1,4-dioxane 
• 14300-06-2 N-butyl-N-nitroso-acetamide 
• 56-23-5 tetrachloromethane 
• 98276-11-0 1-butylperoxy-ethanol 
• 64-17-5 ethanol 
• 142-82-5 n-heptane 
• 67-66-3 chloroform 
• 142-96-1 dibutyl ether 
• 507-02-8 acetyl iodide 
• 591-78-6 n-hexan-2-one 
• 1912-32-9 n-butyl methanesulfonate 
• 127-09-3 sodium acetate 
• 106-42-3 para-xylene 
• 108-24-7 acetic anhydride 

Downstream Products

• 141-32-2 acrylic acid n-butyl ester 
• 21305-56-6 3-methylthio-4-phenyl-1,2-dithiolium iodide 
• 1591-02-2 dimethyldibutoxysilane 
• 136-60-7 benzoic acid, butyl ester 
• 591-60-6 butyl acetoacetate 
• 108-21-4 Isopropyl acetate 
• 3085-30-1 aluminum tri-n-butoxide 
• 60-35-5 acetamide 
• 106-98-9 1-butylene 
• 2203-36-3 3-chloro-1-butyl acetate 
• 6962-92-1 4-Chlorobutyl acetate 
• 7779-75-1 isobutyl acetoacetate 
• 5917-45-3 3-butoxy-3-oxopropanoic acid 
• 64-19-7 acetic acid 

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Relevant articles and documents

Characterization of HNbMoO6, HNbWO6 and HTiNbO 5 as solid acids and their catalytic properties for esterification reaction

HTiNbO5, HNbMoO6·H2O and HNbWO 6·1.5H2O were prepared by proton-exchange of the precursors KTiNbO5, LiNbMoO6 and LiNbWO6, respectively, which were synthesized by a solid-state reaction method. The morphology and the micro-structure were characterized by means of scanning electron microscope (SEM), transmission electron microscope (TEM), powder X-ray diffraction (XRD) and Fourier-transform infrared spectroscopy (FT-IR). NH 3 temperature-programmed desorption (NH3-TPD) was used to measure the acidic properties of the samples. The Sanderson electronegativity and Kataoka′s bond strength theory were also applied to investigate the acid properties of the as-prepared samples. Finally, their catalytic activities were evaluated through catalyzing the liquid-phase esterification reaction of acetic acid and n-butanol to form n-butyl acetate. It has been revealed that H+ ions existed in different forms and interaction modes with MO bond in the solid acids. The acid strength for these as-prepared samples follows the order HNbMoO6·H2O > HNbWO6·1. 5H2O > HTiNbO5. In this work, HNbMoO 6·H2O presents an excellent catalytic activity for the esterification reaction, while HNbWO6·1.5H2O and HTiNbO5 have little catalytic activity. The result suggested that the catalytic activity of the layered solid acid for the esterification reaction was mainly controlled by gallery height.

A facile synthesis of vanadium phosphate: An efficient catalyst for solvent free esterification of acetic acid

This paper reports the facile synthesis of vanadium phosphate (VPO) by the decomposition of VOHPO4?0.5H2O which was prepared by reduction of dihydrate VOPO4?2H2O with isobutanol. The material was promoted with aluminum by impregnation method. The catalysts were unambiguously characterized by N2 adsorption-desorption, XRD, FT-IR techniques, UV-Vis DRS and the total amount of the acidity of the catalysts was estimated by NH3-TPD. The catalytic activities were checked in the heterogeneous catalytic esterification of acetic acid with 1° alcohol (n-butanol) in a solvent free medium. The optimization of reaction was carried out by varying temperature from 75 to 150 °C, molar ratio (butanol:acetic acid) from 1:1 to 1:4. Under optimum conditions, the catalytic esterification runs revealed a significant effect of the VPO giving 62% conversion with 100% selectivity to butyl acetate.

PHASE TRANSFER CATALYSTS POLYETHYLENE GLYCOLS IMMOBILIZED ONTO METAL OXIDE SURFACES

Catalysts prepared by reacting polyethylene glycol and polyethylene glycol monomethyl ether with both alumina and silica gel were found to be effective phase transfer agents in displacement and oxidation reactions.

Facile synthesis of dodecatungstophosphoric acid @ TiO2 pillared montmorillonite and its effectual exploitation towards solvent free esterification of acetic acid with n-butanol

An acid activated montmorillonite, treated with organic cationic surfactant, i.e. cetyltrimethylammonium bromide (CTAB), was used as a template to prepare TiO2 pillared montmorillonite taking titanium ethoxide as titania precursor in hydrochloric acid environment. The pillared montmorillonite was further promoted by dodecatungstophosphoric acid impregnation. The as prepared materials were characterized by various spectroscopic and analytical characterization techniques. The catalyst was employed towards a solvent free esterification of acetic acid with n-butanol. The catalyst showed excellent results with 88% conversion and 100% butyl acetate selectivity. It can be recovered and reused readily, making product isolation and catalyst reuse simple.

Modulation of starch nanoparticle surface characteristics for the facile construction of recyclable Pickering interfacial enzymatic catalysis

In this work, maize starch (MS) was successively modified via an esterification reaction with acetic anhydride (AA) and phthalic anhydride (PTA). Combined with the gelatinization-precipitation process, the formed starch nanoparticles at an AA/PTA ratio of 2 (MS-AP (2)) and 3 (MS-AP (3)) had similar regular spheres but distinct surface characteristics. In order to enhance the activity of lipase B from Candida antarctica (CALB) in an organic solvent, we designed an oil-in-water (o/w) and a water-in-oil (w/o) Pickering interfacial catalytic system simultaneously by utilizing MS-AP (2) and MS-AP (3) as robust Pickering emulsion stabilizers. Impressively, during the esterification of 1-butanol and vinyl acetate, the specific activity of CALB in the o/w (0.0843 U μL-1) or w/o (0.0724 U μL-1) Pickering interfacial catalytic system was much higher than that of free enzymes in the monophasic (0.0198 U μL-1) and biphasic (0.0282 U μL-1) system. Moreover, after preliminarily elaborating mass transfer discrepancies between the o/w and w/o Pickering interfacial catalytic systems and calculating their mass transfer resistance, we clarified the effects of the location of these two phases on the catalytic capacity of the Pickering emulsion. Impressively, both Pickering interfacial catalytic systems exhibited high effectiveness in product separation. It was found that the w/o Pickering emulsion enabled the organic product to be facilely isolated through a simple decantation, while the o/w Pickering emulsion achieved similar results after adjusting the system temperature. The bio-based nanomaterials and simple protocol, in conjunction with the stability to simultaneously achieve high catalysis efficiency and excellent recyclability, makes us believe that this starch nanoparticle-based Pickering interfacial catalytic system is a promising system for meeting the requirements of green and sustainable chemistry.

Esterification of acetic acid with n-Butanol using vanadium oxides supported on γ-alumina

Esterification of acetic acid with n-Butanol has been studied in a heterogeneous reaction system using two γ-alumina-supported vanadium oxide catalysts with different V loadings, which were prepared by the impregnation of a precipitated alumina. The alumina support and the supported catalysts were characterized using X-ray diffraction, N2 adsorption, EDX analysis and NH3-TPD techniques. The effects of the reaction time, of the molar ratio of the reactants, of the speed of agitation and of the mass fraction of the catalyst on the catalytic properties were studied. In the presence of the supported catalyst containing 10 wt % V2O5 (10V-Al2O3 sample) the conversion reached 87.7% after 210 min of reaction at 100 °C with an n-Butanol-to-acetic acid mole ratio equal to one. The conversion as well as the total acidity measured by TPD of NH 3 increased in the following order: Al2O3 2O3 (5 wt % V2O5/Al 2O3) 2O3. In all cases the reaction was completely selective to n-butyl acetate. Nevertheless, a loss in catalytic activity after three reaction cycles with 10 V2O 5-Al2O3 catalyst was observed.

Polymers as reagents and catalysts. Part 28. The effect of polymer catalyst structure on the esterification of acids

Crosslinked sulphonated polystyrene (Dowex 20 M) and various salts of crosslinked co-poly[styrene-4-vinylpyridine] with hydrogen halides were used as solid catalysts in investigations of the conversion of acids to esters. The role of the structure of the acid (acetic acid, benzoic acid), solvent (n-octane, toluene, n-butanol) and reaction temperature in the presence of polymer supported catalyst was tested in the reaction with n-butanol. Sulphonated crosslinked polystyrene (3a) was the most active catalys, similar activity was found with crosslinked co-poly[styrene-4-vinyl(pyridinium chloride)], while catalysts bearing a fluoride (3b) and iodide (3e) function were almost unreactive. The important role of co-solvents was also established.

One-step synthesis of a novel carbon-based strong acid catalyst through hydrothermal carbonization

A novel carbon-based strong acid catalyst was synthesized through the one-step hydrothermal carbonization of furaldehyde and p-toluenesulfonic acid (PTSA) in aqueous solution at 180 °C for only 4 h. The novel carbonbased solid acid possessed high acidity, and the catalytic activities were investigated by esterification and oxathioketalization. The results showed that the novel catalyst demonstrated much greater activity than the traditional solid acids and was comparable to sulfuric acid. The onestep method provides an efficient procedure for the synthesis of various functionalized carbons by one-step hydrothermal carbonization. Springer-Verlag 2010.

A Convenient Synthesis of Isotopically Labelled Anthraquinones, Chrysophanol, Islandicin, and Emodin. Incorporation of Chrysophanol into Tajixanthone in Aspergillus variecolor

Cycloaddition reactions of labelled 6-methoxy-3-methyl-2-pyrone (1) with naphthoquinones provide the common fungal anthraquinones, chrysophanol (2), islandicin (3), and emodin (4) suitably labelled for biosynthetic studies, as demonstrated by synthesis and incorporation of chrysophanol into the xanthone metabolite, tajixanthone (17) in Aspergillus variecolor.

Tailoring ionic liquid catalysts: Structure, acidity and catalytic activity of protonic ionic liquids based on anionic clusters, [(HSO4)(H 2SO4)x]- (x = 0, 1, or 2)

Aiming at inexpensive Bronsted-acidic ionic liquids, suitable for industrial-scale catalysis, a family of protonic ionic liquids based on nitrogen bases and sulfuric acid has been developed. Variation of the molar ratio of sulfuric acid, ?H2SO4, was used to tune acidity. The liquid structure was studied using 1H NMR and IR spectroscopies, revealing the existence of hydrogen-bonded clusters, [(HSO4)(H2SO4)]?, for ?H2SO4 0.50. Acidity, quantified by Gutmann Acceptor Number (AN), was found to be closely related to the liquid structure. The ionic liquids were employed as acid catalysts in a model reaction; Fischer esterification of acetic acid with 1-butanol. The reaction rate depended on two factors; for ?H2SO4 0.50, the key parameter was acidity (expressed as AN value), while for ?H2SO4 0.50 it was the mass transport (solubility of starting materials in the ionic liquid phase). Building on this insight, the ionic liquid catalyst and reaction conditions have been chosen. Conversion values of over 95% were achieved under exceptionally mild conditions, and using an inexpensive ionic liquid, which could be recycled up to eight times without diminution in conversion or selectivity. It has been demonstrated how structural studies can underpin rational design and development of an ionic liquid catalyst, and in turn lead to a both greener and economically viable process.