592-84-7

Basic information

• Product Name: Butyl formate
• Synonyms: 1-butylformate;Butylester kyseliny mravenci;butylesterkyselinymravenci;HCOO(CH2)3CH3;Methanoicacid,butylester;Methanoicacidbutylester;n-Butyl methanoate;FEMA 2196
• CAS NO: 592-84-7
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: 209-772-5
• Product Categories: Industrial/Fine Chemicals
• Mol File: 592-84-7.mol

Chemical Properties

• Melting Point: -91 °C
• Boiling Point: 107 °C
• Flash Point: 57 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.894
• Vapor Pressure: 26.6mmHg at 25°C
• Refractive Index: n20/D 1.389(lit.)
• Storage Temp.: Flammables area
• Explosive Limit: 1.7-8.2%(V)
• Water Solubility: SLIGHTLY SOLUBLE
• BRN: 1742108
• CAS DataBase Reference: Butyl formate(CAS DataBase Reference)
• NIST Chemistry Reference: Butyl formate(592-84-7)
• EPA Substance Registry System: Butyl formate(592-84-7)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37
• Safety Statements: 9-16-24-33
• RIDADR: UN 1128 3/PG 2
• WGK Germany: 1
• RTECS: LQ5500000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 592-84-7(Hazardous Substances Data)

Usage

Uses

Used in the Solvent Industry:
Butyl formate is used as a solvent for nitrocellulose, some types of cellulose acetate, many cellulose ethers, and various natural and synthetic resins. It is also utilized in the production of lacquers and perfumes due to its fruity, plum-like odor.
Used in the Flavoring Industry:
Butyl formate serves as a flavoring agent in the food and beverage industry, contributing to the characteristic fruity and plum-like taste in various products.
Used in the Organic Synthesis Industry:
Butyl formate is employed as an intermediate in organic synthesis, playing a crucial role in the production of various chemicals and compounds.

Preparation

By azeotropic distillation of formic acid and n-butyl alcohol with isopropyl formate; by boiling n-butyl alcohol and formamide in the presence on ZnCl, ZnSo4 or HgCl2.

Synthesis Reference(s)

Journal of the American Chemical Society, 109, p. 3330, 1987 DOI: 10.1021/ja00245a024

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Butyl formate 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. Can generate electrostatic charges [Handling Chemicals Safely 1980. p. 247].

Hazard

Narcotic and irritating in high concentra- tion. Flammable, dangerous fire risk.

Health Hazard

Exposure can cause irritation of eyes, nose and throat. High concentrations have a narcotic effect.

Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation. Human systemic effects by inhalation: muscle contractions and spasticity, conjunctiva irritation, and unspecified respiratory changes. An irritant and narcotic in high concentrations. See also ESTERS, nBUTYL ALCOHOL, and FORMIC ACID. Dangerous fire hazard when exposed to heat or flame. To fight fire, use alcohol foam, foam, CO2, dry chemical. Incompatible with oxidizing materials. When heated to decomposition it emits acrid and irritating fumes.

Purification Methods

Wash the formate with saturated NaHCO3 solution in the presence of saturated NaCl, until no further reaction occurs, then with saturated NaCl solution, dry (MgSO4), filter and fractionally distil the filtrate. [Beilstein 2 IV 28.]

InChI:InChI=1/C5H10O2/c1-2-3-4-7-5-6/h5H,2-4H2,1H3

Upstream product

• 64-18-6 formic acid 
• 22598-39-6 chlorosulfurous acid butyl ester 
• 856371-54-5 1-butoxy-1-formyloxy-ethane 
• 142-96-1 dibutyl ether 
• 588-43-2 Tributyl orthoformate 
• 98-88-4 benzoyl chloride 
• 75-07-0 acetaldehyde 
• 77287-34-4 formamide 
• 71-36-3 butan-1-ol 
• 6267-24-9 tris(ethylsulfanyl)methane 
• 646-06-0 1,3-DIOXOLANE 
• 74-85-1 ethene 
• 1120-97-4 4-methyl-1,3-dioxane 
• 754-05-2 ethenyltrimethylsilane 

Downstream Products

• 98273-82-6 N-(p-chlorophenylsulfonyl)formamide 
• 628-81-9 butyl ethyl ether 
• 762-75-4 tert-butyl formate 
• 123-86-4 acetic acid butyl ester 
• 6343-54-0 N-benzylformamide 
• 6959-71-3 3-butoxypropanenitrile 
• 1014-41-1 1,4-di-sec-butylbenzene 
• 135-98-8 sec-Butylbenzene 
• 93-58-3 benzoic acid methyl ester 
• 136-60-7 benzoic acid, butyl ester 
• 71-43-2 benzene 
• 5454-28-4 butyl heptanoate 
• 50623-57-9 n-butyl nonanoate 
• 79420-98-7 n-butyl 2-methyloctanoate 

Relevant articles and documents

Impregnation of 12-tungstophosphoric acid on tonsil: An effective catalyst for esterification of formic acid with n-butyl alcohol and kinetic modeling

Esterification of formic acid with n-butanol was catalyzed by dodecatungstophosphoric acid, H3PW12O40 (DTP) impregnated on tonsil earth. A series of catalysts containing 10%, 20% and 30% of DTP on tonsil earth were synthesized. The samples were characterized by FT-IR, XRD, BET and TG. The 20% DTP loaded on tonsil showed the highest catalytic activity among the samples prepared in this study. Therefore the kinetics of esterification of formic acid with butanol has been studied in the presence of 20% DTP/T. The kinetic behavior of the reaction has been found to follow the Eley-Rideal model.

Assessment of ion exchange resins as catalysts for the direct transformation of fructose into butyl levulinate

The transformation of fructose into butyl levulinate in aqueous 1-butanol (initial molar ratio 1-butanol/fructose 79, and butanol/water 1.19) has been studied in a discontinuous reactor at 80?120 °C and 2.0 MPa over 8 sulfonic polystyrene-DVB ion exchange resins as catalysts (catalyst loading 0.85–3.4 %). Resins swell greatly in the reaction medium and the reaction takes place mainly in the swollen gel-phase. Swollen resins in water have been characterized by analysis of ISEC data, and spaces originated in the gel phase upon swelling are described in terms of zones of different polymer density. A relationship has been found between the morphology of swollen resins and ester production. Swollen resins with low polymer density show the highest butyl levulinate yield. Dowex 50Wx2 was the most effective because it creates the largest and widest spaces in the gel-phase when swelling. Consequently, it better accommodates the proton-transfer-reaction mechanisms.

Alcohol-Activated Vanadium-Containing Polyoxometalate Complexes in Homogeneous Glucose Oxidation Identified with 51V-NMR and EPR Spectroscopy

Alcoholic solvents, especially methanol, show an activating affect for heteropolyacids in homogenously catalysed glucose transformation reactions. In detail, they manipulate the polyoxometalate-based catalyst in a way that thermodynamically favoured total oxidation to CO2 can be completely supressed. This allows a nearly 100 % carbon efficiency in the transformation reaction of glucose to methyl formate in methanolic solution at mild reaction conditions of 90 °C and 20 bar oxygen pressure. By using powerful spectroscopic tools like 51V-NMR and continuous wave EPR we could unambiguously prove that the vanadate-methanol-complex[VO(OMe)3]n is responsible for the selectivity shift in methanolic solution compared to the aqueous reference system.

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.

Photo-on-Demand Synthesis of Chloroformates with a Chloroform Solution Containing an Alcohol and Its One-Pot Conversion to Carbonates and Carbamates

Chloroformates are key reagents for synthesizing carbonates and carbamates. The present study reports a novel photo-on-demand in situ synthesis of chloroformates with a CHCl3 solution containing a primary alkyl alcohol. It further allowed the one-pot synthesis of carbonates and carbamates through subsequent addition of alcohols or amines, respectively.

A sulfonic acid type double-nuclear ionic liquid in catalytic synthesis of carboxylic acid butyl ester in application and method

The invention relates to the field of organic synthetic technology, in particular discloses a sulfonic acid type double-nuclear ionic liquid in catalytic synthesis of carboxylic acid butyl ester in application and method, the sulfonic acid type can absorb almost double-nuclear ionic liquid as Wherein m=3 - 4 ,n=3 - 4 ,X- For the HSO4- . The carboxylic acid of the n-butyl synthetic method is the double-nuclear ionic liquid the states the sulfonic acid, carboxylic acid and normal butanol added into the reactor, heating to reflux the reaction is carried out, after the reaction is finished layered, recovery of the lower sulfonic acid type double-nuclear ionic liquid catalyst, the upper layer to obtain the product carboxylic acid is n-butyl. The invention selected ionic liquid environment friendly, easy to recycle, to the carboxylic acid esterification reaction of high catalytic efficiency.

PROCESS FOR MAKING FORMIC ACID UTILIZING LOWER-BOILING FORMATE ESTERS

Disclosed is a process for recovering formic acid from a formate ester of a C3 to C4 alcohol. Disclosed is also a process for producing formic acid by carbonylating a C3 to C4 alcohol, hydrolyzing the formate ester of the alcohol, and recovering a formic acid product. The alcohol may be dried and returned to the reactor. The process enables a more energy efficient production of formic acid than the carbonylation of methanol to produce methyl formate.

Sustainable Co-Synthesis of Glycolic Acid, Formamides and Formates from 1,3-Dihydroxyacetone by a Cu/Al2O3 Catalyst with a Single Active Sites

Glycolic acid (GA), as important building block of biodegradable polymers, has been synthesized for the first time in excellent yields at room temperature by selective oxidation of 1,3-dihyroxyacetone (DHA) using a cheap supported Cu/Al2O3 catalyst with single active CuII species. By combining EPR spin-trapping and operando ATR-IR experiments, different mechanisms for the co-synthesis of GA, formates, and formamides have been derived, in which .OH radicals formed from H2O2 by a Fenton-like reaction play a key role.

SEPARATION OF ORGANIC ACIDS FROM MIXTURES CONTAINING AMMONIUM SALTS OF ORGANIC ACIDS

The invention relates to a process for separation of organic acids from mixture of ammonium salts of one or more organic acids and other compounds via an integrated process. The process involves suspending mixture of ammonium salts of one or more organic acids and other compounds in dry hydrocarbon solvent/s or mixtures thereof; wherein the selected hydrocarbon solvent/s or mixtures thereof have boiling point more than 100° C. and forms an azeotrope with water. The reaction mixture thus obtained is dehydrated azeotropically followed by esterification of basic salt of the organic acids by addition of alcohol in presence of metal or metal salt; thereafter the individual esters formed are separated by distillation and hydrolysed to obtain corresponding organic acids having more than 98% purity.

Method for preparing formate-type compound

The invention discloses a method for preparing a formate-type compound. The method comprises the following steps of: adopting an alcohol-type compound and 1,3-dihydroxyacetone as reaction raw materials, and under the existence of a composite catalyst and an oxidant, reacting for 2-48 hours in a reaction medium in a reactor at a reaction temperature of 25-100 DEG C so as to obtain the formate-typecompound. The method disclosed by the invention is simple, and is mild in reaction condition, and by the method, a target product can be obtained by low cost and high yield; the used catalyst has highcatalytic activity, and is easily separated from a reaction system to be repeatedly used; the whole process is environment-friendly, and the reaction raw material (1,3-dihydroxyacetone) is easily converted from a side product (glycerol) of biodiesel, so that the utilization of the glycerol is promoted.