70445-33-9

Usage

Uses

Used in Cosmetic Industry:
3-[2-(Ethylhexyl)oxyl]-1,2-propandiol is used as a natural preservative for cosmetic products, serving as an alternative to parabens. It is used in various cosmetic products such as anti-aging creams, sunscreens, eye shadows, eye creams, lip gloss, deodorants, facial moisturizers, and cleansers.
Used in Deodorant Application:
Ethylhexylglycerin is the novel raw material for deodorants and is widely used as a cosmetic emollient. It reliably inhibits odor-causing bacteria, yeast, and fungi on the skin.
Used as an Emollient Solvent and Fixative:
3-[2-(Ethylhexyl)oxyl]-1,2-propandiol serves as an emollient solvent and a fixative with antimicrobial properties. It is reported to enhance the uptake of preservatives in microorganisms and is often used as an alternative to parabens.
Used in Leave-on and Rinsed-off Products:
Ethylhexylglycerin is used at a concentration up to 2% in leave-on products and 8% in rinse-off products, making it suitable for a wide range of cosmetic applications.

Safety

With an EWG score of 1 and a rating of GOOD from Paula’s Choice, ethylhexylgylcerin is deemed to be very safe and a non-irritant.Ethylhexylglycerin is a topical skin care ingredient and deodorizing agent, often indicated as a conditioning ointment in the treatment of eczema. It can also be a surfactant and preservative-enhancer and can be found as a substituent for parabens. Ethylhexylglycerin is commonly found in baby products or cosmetics marketed as “hypoallergenic” or “formaldehyde free”.Ethylhexylglycerin has been reported to cause dermatitis and skin irritation.www.cir-safety.orgWhat Is Ethylhexylglcerin & Is It Safe?

Toxicity evaluation

The oral toxicity of ethylhexylglycerin (Sensiva? SC 50, in polyethylene glycol 400) at doses of 100, 500, and 1,500 mg/kg was evaluated in a 28-day study using groups of 10 rats of an unspecified strain. The test substance was administered at a dose volume of 5 ml/kg.There were no treatment-related mortalities. Body weight development was retarded in mid- and high-dose groups, and this finding was accompanied by a non-statistically significant reduction in food intake when compared to the control (polyethylene glycol 400) group. Both eye and ear functions remained unchanged during the study, and increased salivation (dose not stated) was the only clinical symptom observed. Hematological parameters were unaffected by treatment; however, serum analyses indicated changes in aminotransferase (above normal) in high-dose rats. Urinalysis and necropsy findings were unremarkable.

Reference

W. Beilfuss, M. Leschke, K. Weber, A New Concept to Boost the Preservative Efficacy of Phenoxyethanol, S?FW-Journal, 2005, vol. 131

Contact allergens

This glycerol monoalkylether is used as a skin conditioning agent, with bactericidal properties against Gram-positive bacteria.

Synthesis

Synthesis of ethylhexylglycerin?is via the catalytic splitting of ethylhexylglycidyl ether followed by the addition of water. The product can then be purified by vacuum distillation.

InChI:InChI=1/C11H24O3/c1-3-5-6-10(4-2)8-14-9-11(13)7-12/h10-13H,3-9H2,1-2H3

Synthetic route

2-ethyl-hexyl glycidyl ether (2461-15-6) → 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
With formic acid; water; sodium hydroxide In Triethylene glycol dimethyl ether at 120℃; for 12h; Reagent/catalyst; Solvent;	98.5%
Stage #1: 2-ethyl-hexyl glycidyl ether With boron trifluoride diethyl etherate In acetone at 10 - 20℃; for 2.66667h; Stage #2: With methylamine In water; acetone at 10 - 20℃; for 0.166667h; Stage #3: With formic acid In water at 50 - 55℃; for 3h; Temperature; Reagent/catalyst;	89.1%
Stage #1: 2-ethyl-hexyl glycidyl ether With formic acid; sulfuric acid at 80 - 100℃; Stage #2: With methanol at 60℃; Stage #3: With water; sodium hydroxide Product distribution / selectivity;	78.1%

2-Ethylhexyl alcohol (104-76-7) + 3-monochloro-1,2-propanediol (96-24-2) → 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
With sodium hydroxide at 90℃; for 0.666667h; Temperature; Reagent/catalyst;	92.4%

glycidyl acetate (6387-89-9) + 2-Ethylhexyl alcohol (104-76-7) → 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
Stage #1: glycidyl acetate; 2-Ethylhexyl alcohol With boron trifluoride diethyl etherate at 20℃; for 4h; Stage #2: With toluene-4-sulfonic acid In water at 100℃; for 8h; Temperature; Solvent;	88.2%

2-Ethylhexanoic acid (149-57-5) + glycerol (56-81-5) → 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
With palladium on activated charcoal; hydrogen at 120℃; under 37503.8 Torr; for 16h; Autoclave; Inert atmosphere;	47%
With palladium on activated charcoal; hydrogen In neat (no solvent) at 120℃; under 37503.8 Torr; for 16h;

2-Ethylhexyl alcohol (104-76-7) + oxiranyl-methanol (556-52-5) → 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
With potassium hydroxide at 65℃; for 2.25h; Reagent/catalyst; Green chemistry;	36%

2-(2-ethyl)hexoxy-1,2-propanediol + d,l-2-ethylhexanal (123-05-7) + glycerol monoethers 3-(2-ethyl)hexoxy-1,2-propanediol → 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
With hydrogen; methanol; palladium-carbon In water; glycerol

d,l-2-ethylhexanal (123-05-7) + glycerol (56-81-5) → 2-Ethylhexyl alcohol (104-76-7) + 5,13-diethyl-7,11-dioxa-9-heptadecanol (59068-03-0) + 2-(2-ethylhexyloxy)-1,3-propanediol (1027549-81-0) + 2,3-di(2-ethylhexyloxy)-1-propanol (59068-04-1) + 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon at 200℃; under 51716.2 Torr; for 22h;	A 6.5 %Chromat. B n/a C n/a D n/a E n/a

2-Ethylhexyl alcohol (104-76-7) → 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / 0.5 h / -40 °C / Inert atmosphere 1.2: 12 h / 40 °C 2.1: boron trifluoride / water; dimethyl sulfoxide / 20 h / 120 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / 0.5 h / -40 °C / Inert atmosphere 1.2: 12 h / 60 °C 2.1: boron trifluoride / water; dimethyl sulfoxide / 20 h / 120 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / 0.5 h / -40 °C / Inert atmosphere 1.2: 12 h / 80 °C 2.1: boron trifluoride / water; dimethyl sulfoxide / 20 h / 120 °C / Inert atmosphere View Scheme

2-ethyl-hexyl glycidyl ether (2461-15-6) → C22H46O5 + 1-O-(2-ethylhexyl)glycerin (70445-33-9)

Conditions	Yield
With water at 300℃; under 760.051 Torr; for 2h; Temperature; Gas phase;

vanillin (121-33-5) + 1-O-(2-ethylhexyl)glycerin (70445-33-9) → vanillin-1-(2-ethyl) hexyloxyglycerol acetal

Conditions	Yield
toluene-4-sulfonic acid In water; toluene at 140℃; for 5h; Heating / reflux; with Dean-Stark tube;	91.9%

dimethyl sulfate (77-78-1) + 1-O-(2-ethylhexyl)glycerin (70445-33-9) → 3-[(2,3-dimethoxypropoxy)methyl]heptane

Conditions	Yield
Stage #1: 1-O-(2-ethylhexyl)glycerin With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In neat (no solvent) at 20℃; Schlenk technique; Inert atmosphere; Stage #2: dimethyl sulfate In neat (no solvent) at 20℃; Schlenk technique; Inert atmosphere;	74%

trimethyl phosphite (512-56-1) + 1-O-(2-ethylhexyl)glycerin (70445-33-9) → 3-[(2,3-dimethoxypropoxy)methyl]heptane

Conditions	Yield
With iron(II) triflate In neat (no solvent) at 100℃; for 15h;	62%

Upstream product

• 2461-15-6 2-ethyl-hexyl glycidyl ether 
• 104-76-7 2-Ethylhexyl alcohol 
• 96-24-2 3-monochloro-1,2-propanediol 
• 556-52-5 oxiranyl-methanol 
• 149-57-5 2-Ethylhexanoic acid 
• 56-81-5 glycerol 
• 123-05-7 d,l-2-ethylhexanal 
• 6387-89-9 glycidyl acetate 

Relevant academic research and scientific papers

Method for continuously synthesizing ethylhexylglycerin by micro-channel reactor

The invention discloses a method for continuously synthesizing ethylhexylglycerin by using a micro-channel reactor. The method comprises the following steps: by using isooctyl alcohol, 3-chloro-1, 2-propylene glycol and inorganic base as raw materials, carrying out ethylhexylglycerin continuous synthesis by using the micro-channel reactor, separating the organic phase from a product, distilling and the like to obtain the high-purity ethylhexylglycerin product. According to the process method disclosed by the invention, the characteristics that the micro-channel reactor strengthens heat transfer and mass transfer and can realize accurate control are fully utilized; the defects of more byproducts, difficulty in control, poorer reaction selectivity, low product yield, complicated process, higher cost and the like caused by non-uniform reaction heating when the ethylhexylglycerin is synthesized by the conventional reactor equipment are overcome, continuous production and automatic control of the process can be realized, production is efficient and safe in production, mild reaction conditions, short reaction time, high product purity and yield are also realized, and the method is green and economic, and is beneficial to popularization and application of ethylhexylglycerin in cosmetics and daily chemical industries.

METHODS FOR PREPARING ALKYLGLYCERYL ETHERS

The present invention relates to a method for manufacturing alkyl glyceryl ether by conducting reaction of alkyl glycidyl ether and water in the presence of a solvent and a catalyst to obtain alkyl glyceryl ether, wherein the solvent comprises glycol ethers, and the catalyst comprises an alkali metal salt of a carboxylic acid. The method of the present invention does not require use of chemicals other than the solvent and the catalyst, so that the production cost is low and cost-effective.COPYRIGHT KIPO 2018

A process for preparing ethyl hexyl glycerin method

This invention discloses a process for preparing ethyl hexyl glycerin method, comprises the following steps: (1) in order to boron trifluoride ether solution is used as the catalyst, under stirring condition, make the isooctanol and glycidyl ester type of stirring at room temperature the reaction, to produce intermediate; (2) in the step (1) and capable of adding acid as catalyst, and then adding water or alcohol, under the conditions of normal pressure or reduced in the reaction, so that the steps (1) intermediate obtained by hydrolysis or alcoholysis; (3) the step (2) of the product after washing liquid, ethyl hexyl glycerin through distillation. The invention of the method of preparing ethyl hexyl glycerin operation process is simple, mild reaction conditions, low energy consumption, is suitable for the large-scale industrial production, can be colorless ethyl hexyl glycerin, product yield is greater than 82%, the purity of 99% or more.

A process for preparing high purity ethyl hexyl glycerin method

The invention provides a method for preparing high-purity ethylhexylglycerin. According to the method, an intermediate 4-alkoxymethyl-1,3-dioxoane is generated from 2-ethylhexylglycidyl ether and acetone under the action of boron trifluoride diethyl etherate, a terminator is added in good time before hydrolysis, and after liquid separation, an oil-phase substance is neutralized by use of sodium hydrogen carbonate and then washed, next, a stabilizer is added, and finally, the high-purity ethylhexylglycerin is obtained by use of short-path distillation. The method is suitable for cosmetic additives and suitable for large-scale industrial production, and has the advantages of simple process, small energy consumption, product yield of greater than 88%, purity of 99.3%, no color and no taste, and the like.

The Preparation method of 2-ethylhexylglycerolether from 2-ethylhexylglycidylether by gas phase hydrolysis

The present invention relates to a method for manufacturing 2-ethyl hexyl glycerol ether, which performs hydrolysis of 2-ethyl hexyl glycidyl ether by reacting the 2-ethyl hexyl glycidyl ether with water, while controlling the reaction temperature at the temperature of 250-350anddeg;C to process the reaction in a gas phase. In the present invention, by applying a method of vapor phase hydrolysis of 2-ethyl hexyl glycidyl ether in the manufacture of 2-ethyl hexyl glycerol ether, it is possible to ensure simplification and efficiency of manufacturing processes, and to achieve a high yield of 2-ethyl hexyl glycerol ether which is a target material by inhibiting the generation of 2-ethyl hexyl glycerol ether dimer byproducts in a reaction step.(AA) Vaporizer(BB) Controlled volume pump(CC) 2-ethyl hexyl glycidyl ether(DD) Water(EE) Vapor phase hydrolysis reactor(FF) Condensate plate(GG) Exhaust treatment(HH) Vacuum pump(II) Low temperature cooing device(JJ) Product collecting device(KK) 2-ethyl hexyl glycidyl ether purification processCOPYRIGHT KIPO 2017

Synthesis of 3-alkoxypropan-1,2-diols from glycidol: Experimental and theoretical studies for the optimization of the synthesis of glycerol derived solvents

A straightforward synthetic methodology has been derived for the synthesis of glycerol monoethers from glycidol and alcohols. Several homogeneous and heterogeneous basic catalysts have been tested, the best results being obtained with readily available and inexpensive alkaline metal hydroxides. In the best case, good yield of the desired monoether is obtained under smooth reaction conditions, always with total conversion of glycidol. The selectivity of the reactions mainly depends on the alcohol used, due to the concurrence of undesired side reactions. A mechanistic study carried out through computational DFT calculations, in which solvent effects are taken into account, also complemented the experiments, has allowed to identify the main reaction paths taking place under reaction conditions, giving insights into the main causes affecting the reaction selectivity and also into how it could be improved.

Method for producing ethylhexylglycerin

The present invention provides a producing method of ethylhexylglycerin, comprising the steps of (A) agitating 2-ethylhexylglycidyl ether, water, an organic solvent and a catalyst; (B) reacting the mixture at 80-120anddeg;C for 15-25 hours after the agitation, and then synthesizing ethylhexylglycerin; (C) adding ethylacetate after the synthesis; (D) removing a water layer in the step (C) and washing an organic layer with water; and (E) distilling the washed organic layer, and accordingly obtaining ethylhexylglycerin.(AA) Temperature(anddeg;C)COPYRIGHT KIPO 2015

1,2,3-Trimethoxypropane and glycerol ethers as bio-sourced solvents from glycerol: Synthesis by solvent-free phase-transfer catalysis and utilization as an alternative solvent in chemical transformations

1,2,3-Trimethoxypropane (2), 1-alkoxy-2,3-dimethoxy-propanes, and 1-aryloxy-2,3-dimethoxypropanes were prepared in good yields and selectivity by solid-liquid phase-transfer catalysis in the presence of an inorganic base and an ammonium salt as the phase-transfer catalyst with no additional solvent. No heating was required, and the synthesis was easily performed under atmospheric pressure on a 150g scale. For the preparation of 2, the conversion of glycerol was complete and the selectivity for the expected glycerol trimethylether was above 95%. This product was utilized as a solvent in organic reactions such as transesterifications between glycerol and vegetable oil, organometallic reactions (Grignard- and Barbier-type reactions), carbon-carbon coupling reactions (Suzuki, Sonogashira, Heck), and in etherification reactions by dehydrogenative alkylation. The solvent showed interesting properties for the solubilization of polymers.

COALESCENT FOR AQUEOUS COMPOSITIONS

A coalescent composition selected from 1,3-(C6-C12alkyloxy)-2-propanol, 1,1′-oxybis[3-(C6-C12alkyloxy)]-2-propanol, and mixtures thereof is provided. Preferred coalescents are 1,3-(decyloxy)-2-propanol and 1,1′-oxybis[3-(heptyloxy)]-2-propanol. A method for forming glycerol diethers and diglycerol diethers, an aqueous coating composition including the coalescent compositions and a method for forming a coating are also provided.

Selective synthesis of 1-O-Alkyl(poly)glycerol ethers by catalytic reductive alkylation of carboxylic acids with a recyclable catalytic system

(Poly)glycerol monoethers were synthesized in good yield and selectivity by the catalytic reductive alkylation of glycerol, diglycerol, and triglycerol with readily available, cheap and/or bio-sourced carboxylic acids. The reaction was catalyzed by 1 mol % of Pd/C under 50 bar H2 using an acid ion-exchange resin as a recyclable cocatalyst. The catalytic system was recycled several times, and a mechanism is proposed for this transformation.