19224-26-1

Basic information

• Product Name: 1,2-PROPANEDIOL DIBENZOATE
• Synonyms: 1,2-PROPANEDIOL DIBENZOATE;propane-1,2-diyl dibenzoate;Propylene glycol dibenzoate;1,2-PROPANEDIOL DIBENZOATE 96%;Bis(benzoic acid)propane-1,2-diyl ester;1,2-Propanediol,1,2-dibenzoate
• CAS NO: 19224-26-1
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31
• EINECS: 242-894-7
• Product Categories: C12 to C63;Carbonyl Compounds;Esters
• Mol File: 19224-26-1.mol

Chemical Properties

• Melting Point: −3 °C(lit.)
• Boiling Point: 232 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.16 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.8E-06mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Water Solubility: 7.7mg/L at 20℃
• CAS DataBase Reference: 1,2-PROPANEDIOL DIBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-PROPANEDIOL DIBENZOATE(19224-26-1)
• EPA Substance Registry System: 1,2-PROPANEDIOL DIBENZOATE(19224-26-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19224-26-1(Hazardous Substances Data)

Usage

Chemical Properties

Propylene glycol dibenzoate has virtually no odor.

InChI:InChI=1/C17H16O4/c1-13(21-17(19)15-10-6-3-7-11-15)12-20-16(18)14-8-4-2-5-9-14/h2-11,13H,12H2,1H3

Synthetic route

propylene glycol (57-55-6) + benzoic acid (65-85-0) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With Sb2(OCH2CH2O)3 at 180℃; for 30h;	94%
sulfonic acid at 120 - 225℃;
at 120 - 225℃;

benzoyl cyanide (613-90-1) + propylene glycol (57-55-6) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With dmap; 1-ethylene glycol monomethyl ether-3-methylimidazolium methanesulfonate at 25 - 35℃;	92%

propylene glycol (57-55-6) + benzoic acid anhydride (93-97-0) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; for 8h;	85%

propylene glycol (57-55-6) + diethyl benzoylphosphonate (3277-27-8) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.333333h; Product distribution; Ambient temperature;	A 17 % Spectr. B 83 % Spectr. C 8%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.333333h; Ambient temperature;	A 17 % Spectr. B 83 % Spectr. C 8%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.333333h; Ambient temperature; Title compound not separated from byproducts;	A 17 % Spectr. B 83 % Spectr. C 8%

1,2-Dibromopropane (78-75-1) + silver benzoate (532-31-0) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield

silver benzoate (532-31-0) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With iodine; benzene anschliessend Behandeln mit Propen;

propylene glycol (57-55-6) + N-benzoyloxybenzotriazole (54769-36-7) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With triethylamine In dichloromethane for 24h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

propylene glycol (57-55-6) + benzoyl chloride (98-88-4) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
multistep reaction: monoacylation of diols with reversed chemoselectivity; other diols; quenching with chlorosilanes;
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

propylene glycol (57-55-6) + benzoic acid (65-85-0) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 1h; Product distribution; Mechanism; other asymmetric 1,2-diol;

propylene glycol (57-55-6) + dibenzoyl peroxide (94-36-0) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With triphenylphosphine In dichloromethane for 1h; Product distribution; Mechanism; Ambient temperature; other diols, other benzoylating agent;

benzoyl chloride (98-88-4) + (+-)-propylene glycol → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With pyridine

benzoyl chloride (98-88-4) + lead sulfide → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / Et3N / CH2Cl2 / 0.33 h 2: Et3N / CH2Cl2 / 24 h / Ambient temperature View Scheme

benzoyl fluoride (455-32-3) + C21H26O2Si → 2-((1,3-diphenylprop-2-yn-1-yl)oxy)propyl benzoate + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With dmap In chloroform-d1 at 20℃; Inert atmosphere; Overall yield = 30.6 mg;

1,2-bis-benzoyloxy-propane (19224-26-1) → [(1R)-2-hydroxy-1-methyl-ethyl]benzoate (113566-74-8) + (S)-1-hydroxypropan-2-yl benzoate (113566-73-7)

Conditions	Yield
With octanol; Pseudomonas sp. lipase PS*celite In di-isopropyl ether at 20℃; Product distribution; Further Variations:; Reagents;

Upstream product

• 57-55-6 propylene glycol 
• 3277-27-8 diethyl benzoylphosphonate 
• 65-85-0 benzoic acid 
• 93-97-0 benzoic acid anhydride 
• 455-32-3 benzoyl fluoride 
• 613-90-1 benzoyl cyanide 
• 98-88-4 benzoyl chloride 
• 94-36-0 dibenzoyl peroxide 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 532-31-0 silver benzoate 
• 78-75-1 1,2-Dibromopropane 

Downstream Products

• 113566-74-8 [(1R)-2-hydroxy-1-methyl-ethyl]benzoate 
• 113566-73-7 (S)-1-hydroxypropan-2-yl benzoate 

Relevant articles and documents

Method for triggering hydroxy selective acylation of dihydric alcohol or polyhydric alcohol by catalytic amount of organic amine

The invention belongs to the field of organic chemical engineering, and particularly provides a method for triggering hydroxy selective acylation of dihydric alcohol or polyhydric alcohol by a catalytic amount of organic amine. According to the method, dihydric alcohol or polyhydric alcohol dissolves in an appropriate amount of organic solvents, a chemical amount of anhydride and the catalytic amount of organic amine are added, N,N-diisopropylethylamine is added particularly, reaction is conducted at the temperature of 0-50 DEG C for 4-12 hours, and high-selectivity acylation on specific hydroxyl can be realized. The method has the advantages that reaction conditions are mild, the method is simple and convenient to operate, inhibitors are green, environmentally friendly, low in cost and easy to get, and the method has wide application value in labs and industries.

Catalytic Alkynylation of Cyclic Acetals and Ketals Enabled by Synergistic Gold(I)/Trimethylsilyl Catalysis

A completely regioselective and challenging gold(I)-catalyzed ring-opening of cyclic 1,3-dioxolanes and dioxanes by trimethylsilyl alkynes to set diol-derived propargyl trimethylsilyl bis-ethers is reported. This unprecedented and not trivial transformation does not operate with the catalytic methodologies recently reported for catalytic alkynylation of acyclic acetals/ketals, and is uniquely enabled by the application of a recently introduced synergistic gold(I)-silicon catalysis concept capable of producing simultaneously catalytic amounts of two key players, a silicon-based Lewis superacid and a nucleophilic gold acetylide.

A two-benzoic acid preparation method of dihydric alcohol ester plasticizers (by machine translation)

A two-benzoic acid dihydric alcohol ester plasticizers of the preparation method, the method to benzoic acid and dihydric alcohol as raw materials, in under the catalytic action, 100 - 250 °C, to carry out the esterification reaction, the reaction 0.5 - 48h. By distilling under reduced pressure, to obtain two-benzoic acid dihydric alcohol ester product. Two-benzoic acid ester is a non-toxic alcohol plasticizer, can replace the phthalic acid ester used for plastic, rubber in the industry field. The method for preparing the product of high yield, product is easy to separate, environment friendly, has very good application prospect. (by machine translation)

Personal care products containing high refractive index esters and methods of preparing the same

The invention includes personal care compositions and methods of preparing these personal care compositions that include incorporation of a polyol polyester that is the reaction product of an aliphatic polyol that does not contain an ether group, and benzoic acid, wherein the resultant polyol polyester has a refractive index at 25° C. of greater than about 1.5. The aliphatic polyol may have two to three carbon atoms. Alternatively, the invention includes personal care compositions and methods of preparing personal care compositions including incorporating a polyol polyester into a personal care formulation. The polyol polyester is represented by formula (I): wherein R is an aliphatic alkyl group that does not contain an ether group and has a refractive index of greater than about 1.5 at 25° C. Also described are methods of preparing personal care compositions comprising a first phase and a second phase, wherein the second phase contains any of the polyol polyesters described above.

PERSONAL CARE PRODUCTS CONTAINING HIGH REFRACTIVE INDEX ESTERS AND METHODS OF PREPARING THE SAME

The invention includes personal care compositions and methods of preparing these personal care compositions that include incorporation of a polyol polyester that is the reaction product of an aliphatic polyol that does not contain an ether group, and benzoic acid, wherein the resultant polyol polyester has a refractive index at 25° C of greater than about 1.5. The aliphatic polyol may have two to three carbon atoms. Alternatively, the invention includes personal care compositions and methods of preparing personal care compositions including incorporating a polyol polyester into a personal care formulation. The polyol polyester is represented by formula (I): wherein R is an aliphatic alkyl group that does not contain an ether group and has a refractive index of greater than about 1.5 at 25° C. Also described are methods of preparing personal care compositions comprising a first phase and a second phase, wherein the second phase contains any of the polyol polyesters described above.

'Green' methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid

Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a 'green' alternative and mild reaction condition protocol to conventional pyridine-benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide-ionic liquid combination has been successfully extended for highly efficient benzoylation of phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol, which indicates the versatility of this benzoylating system.

Solubilizing agents for active or functional organic compounds

An active or functional organic compound is solubilized in a diaryl organic compound having a polar or polarizable functional group therein, as a solvent, cosolvent or additive, to form a composition thereof. Representative active or functional organic compounds include those present in personal care products, e.g., sunscreens containing UVA/UVB absorbing compounds, such as avobenzone, benzophenone-3, and 4-methylbenzylidene camphor. Such compositions also show increased SPF, UVA/UVB absorbance ratio, and critical wavelength performance properties.

Antiperspirant compositions

Antiperspirant compositions comprise an antiperspirant active and a carrier oil in which the carrier oil comprises an aromatic ester oil obeying the general formula: [in-line-formulae]R1—CO2—X—Y—R2 [/in-line-formulae] in which R1 and R2 each represent a phenyl group, X represents an alkylene group containing from 2 to 4 carbons including at least one pendant alkyl group and Y represents a bond, or an ether or ester linkage.

Organotin-Mediated Monoacylation of Diols with Reversed Chemoselectivity: A Convenient Synthetic Method

The organotin-mediated monoesterification of unsymmetrical diols with reversed chemoselectivity has been explored to ascertain scope and limits of the method and to provide an easy and convenient synthetic procedure.The reaction has been performed on a set of substituted diols with some acylating agents usually employed as protecting groups.Two different procedures have been devised to obtain either the desired diol monoesters directly or the corresponding trialkylsilyl ethers as protected derivatives.The latter provides a convenient approach to the preparation of easily interconvertible diol monoesters.Also, the reaction has been optimized as a one-pot procedure, avoiding the isolation and purification of the stannylated intermediates.The reversed monoesterification method has been successfully applied to 1,2-, 1,3-, and 1,4-diols of primary-secondary, primary-tertiary, and secondary-tertiary types and to ether functions containing 1,2-diols.Within its limits, the described method represents the first direct one-pot monoesterification of diols at the most substituted site, allowing some remarkable achievements as (a) an almost regiospecific reversed monobenzoylation of some 1,2-diols, (b) the selective acylation of the tertiary hydroxyl of a primary-tertiary diol, and (c) a highly selective preparation of secondary pivalate of primary-secondary diols.