14144-48-0

Basic information

• Product Name: butyl 3-butoxypropanoate
• Synonyms: butyl 3-butoxypropanoate
• CAS NO: 14144-48-0
• Molecular Formula: C₁₁H₂₂O₃
• Molecular Weight: 202.29
• Mol File: 14144-48-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 280.42°C (rough estimate)
• Flash Point: 92.124 °C
• Appearance: /
• Density: 1.0270 (rough estimate)
• Vapor Pressure: 0.00801mmHg at 25°C
• Refractive Index: 1.4174 (estimate)
• Water Solubility: 799.4mg/L(25 oC)
• CAS DataBase Reference: butyl 3-butoxypropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: butyl 3-butoxypropanoate(14144-48-0)
• EPA Substance Registry System: butyl 3-butoxypropanoate(14144-48-0)

Safety Data

• Hazardous Substances Data: 14144-48-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 544, 1946 DOI: 10.1021/ja01208a003

InChI:InChI=1/C11H22O3/c1-3-5-8-13-10-7-11(12)14-9-6-4-2/h3-10H2,1-2H3

Synthetic route

β-Propiolactone (57-57-8) + butan-1-ol (71-36-3) → butyl 3-butoxypropionate (14144-48-0)

Conditions	Yield
With sulfuric acid

acrylic acid n-butyl ester (141-32-2) + sodium butanolate (2372-45-4) → butyl 3-butoxypropionate (14144-48-0)

acrylic acid methyl ester (292638-85-8) + sodium butanolate (2372-45-4) → butyl 3-butoxypropionate (14144-48-0)

methyl 3-methoxypropionate (3852-09-3) + butan-1-ol (71-36-3) → butyl β-methoxypropionate (4195-88-4) + butyl 3-butoxypropionate (14144-48-0)

Conditions	Yield
With sodium butanolate

acrylic acid n-butyl ester (141-32-2) + butan-1-ol (71-36-3) → butyl 3-butoxypropionate (14144-48-0)

Conditions	Yield
in Gegenwart eines basischen Anionenaustauschers;
With calcium hydroxide at 50℃; Product distribution / selectivity;

sulfuric acid mono-(2-carbamoyl-ethyl) ester (3840-67-3) + butan-1-ol (71-36-3) → butyl 3-butoxypropionate (14144-48-0)

3-Bromo-propionimidic acid butyl ester; hydrochloride + butan-1-ol (71-36-3) → butyl 3-butoxypropionate (14144-48-0)

3-hydroxypropionic acid (503-66-2) + butan-1-ol (71-36-3) → acrylic acid n-butyl ester (141-32-2) + butyl-β-hydroxy propionate (4890-38-4) + butyl 3-butoxypropionate (14144-48-0)

Conditions	Yield
magnesium hydroxide In water at 220℃; under 2585.81 Torr; for 1.6h; Product distribution / selectivity;	A 47 %Chromat. B 5 %Chromat. C 48 %Chromat.
sodium hydroxide In water at 220℃; under 2585.81 Torr; for 1.6h; Product distribution / selectivity;
calcium hydroxide In water at 220℃; under 2585.81 Torr; for 1.6h; Product distribution / selectivity;

acrylic acid (79-10-7) + butan-1-ol (71-36-3) → acrylic acid n-butyl ester (141-32-2) + butyl 3-butoxypropionate (14144-48-0) + n-butyl β-acryloxypropionate (39181-89-0)

Conditions	Yield
With 10H-phenothiazine at 107.8 - 117.4℃; under 9.976 Torr; for 0.25h; Product distribution / selectivity; dispersant Beycostat FB095;

acrylic acid (79-10-7) + butan-1-ol (71-36-3) → acrylic acid n-butyl ester (141-32-2) + butyl 3-butoxypropionate (14144-48-0)

Conditions	Yield
With 10H-phenothiazine; sulfuric acid In water at 80 - 100℃; under 90 - 620 Torr; for 2 - 3.5h; Product distribution / selectivity;

butyl 3-butoxypropionate (14144-48-0) + dimethyl amine (124-40-3) → 3-n-butoxy-N,N-dimethylpropionamide

Conditions	Yield
With diglycerol; potassium tert-butylate at 60℃; for 6h; Autoclave;	85%

2-methoxy-ethanol (109-86-4) + butyl 3-butoxypropionate (14144-48-0) → 3-butoxy-propionic acid-(2-methoxy-ethyl ester)

Conditions	Yield
With sulfuric acid
With toluene-4-sulfonic acid

2-Butoxyethanol (111-76-2) + butyl 3-butoxypropionate (14144-48-0) → 3-butoxy-propionic acid-(2-butoxy-ethyl ester) (7770-34-5)

Conditions	Yield
With toluene-4-sulfonic acid
With sulfuric acid

butyl 3-butoxypropionate (14144-48-0) + sodium butanolate (2372-45-4) → 2-butoxymethyl-3-methoxy-acrylic acid butyl ester (100538-51-0)

Conditions	Yield
With formic acid ethyl ester; benzene beim Erwaermen des Reaktionsgemisches mit Dimethylsulfat;

butyl 3-butoxypropionate (14144-48-0) + n-butyl β-acryloxypropionate (39181-89-0) → dibutyl ether (142-96-1) + acetic acid butyl ester (123-86-4) + acrylic acid n-butyl ester (141-32-2) + acrylic acid (79-10-7) + butan-1-ol (71-36-3)

Conditions	Yield
With TEMPOL; sulfuric acid at 135.7 - 174.3℃; under 760.051 Torr; for 0.5h; Conversion of starting material; dispersant Beycostat FB095;

acrylic acid n-butyl ester (141-32-2) + butyl-β-hydroxy propionate (4890-38-4) + butyl 3-butoxypropionate (14144-48-0) + n-butyl β-acryloxypropionate (39181-89-0) + hydroquinone (123-31-9) → acrylic acid (79-10-7) + butan-1-ol (71-36-3)

Conditions	Yield
With methoxyquinone; sulfuric acid In water at 190℃; under 750.075 Torr; Product distribution / selectivity;

Upstream product

• 3852-09-3 methyl 3-methoxypropionate 
• 71-36-3 butan-1-ol 
• 141-32-2 acrylic acid n-butyl ester 
• 79-10-7 acrylic acid 
• 503-66-2 3-hydroxypropionic acid 
• 3840-67-3 sulfuric acid mono-(2-carbamoyl-ethyl) ester 
• 292638-85-8 acrylic acid methyl ester 
• 2372-45-4 sodium butanolate 
• 57-57-8 β-Propiolactone 

Downstream Products

• 7770-34-5 3-butoxy-propionic acid-(2-butoxy-ethyl ester) 
• 142-96-1 dibutyl ether 
• 123-86-4 acetic acid butyl ester 
• 141-32-2 acrylic acid n-butyl ester 
• 79-10-7 acrylic acid 
• 71-36-3 butan-1-ol 

Relevant articles and documents

PROCESS FOR PRODUCING -ALKOXYPROPIONAMIDE

A method for producing a β-alkoxypropionamide shown by the following formula (I) including the step of reacting a β-alkoxypropionic acid ester with an amine in the presence of a basic catalyst or in the presence of a basic catalyst and a polyol: wherein R1 is an alkyl group having 1 to 8 carbon atoms, and R2 and R3 are independently hydrogen, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a methoxymethyl group or a glycidyl group.

PROCESS FOR THE MANUFACTURE OF C1 -C4 ALKYL (METH)ACRYLATES

The invention relates to an improved process for the manufacture of C1-C4 alkyl (meth)acrylates by a direct esterification of (meth)acrylic acid by the corresponding alcohol in the presence of sulphuric acid, phenothiazine being used as polymerization inhibitor. The said process comprises a stage of recovering in value the heavy byproducts generated during this manufacture which consists of a distillation at a relatively low temperature and under an inert atmosphere, followed by a catalytic cracking under an inert atmosphere.

METHODS OF MANUFACTURING DERIVATIVES OF β-HYDROXYCARBOXYLIC ACIDS

Preparation of derivatives of β-hydroxycarboxylic acid, including β-hydroxycarboxylic acid esters, α,β-unsaturated carboxylic acids, esters of α,β-unsaturated carboxylic acid, and alkoxy derivatives.

Process for preparing butyl acrylate by direct esterification

Butyl acrylate is prepared by reacting acrylic acid and butanol in a reactor in the presence of an esterification catalyst the water formed being entrained by distillation in a column (2) in the form of a heteroazeotropic mixture with butanol mixture following condensation, being separated in a decanter (3) to give an upper, organic phase which is recycled to the top of the distillation column (2) and a lower, aqueous phase which is drawn off. The reaction is conducted with deferred introduction of part of the butanol at the top of the distillation column (2) or to the decanter (3) or to the reactor (1), the butanol/acrylic acid molar ratio being initially between 0.5 and 1 before rising to between 1 and 1.5 following the completion of the deferred introduction of the butanol.

Transesterification of alkoxyesters

Method for the highly selective transesterification of alkyl 3-alkoxypropionates, as well as several novel alkoxypropionate compounds, are provided. Transesterification catalyzed by titanium alkoxides or tin compounds does not catalyze the Michael reaction, and therefore, provide highly selective transesterification reactions of these reactive materials.