106972-45-6

Basic information

• Product Name: DL-Glycerin-1-n-hexylether
• Synonyms: DL-Glycerin-1-n-hexylether
• CAS NO: 106972-45-6
• Molecular Formula: C₉H₂₀O₃
• Molecular Weight: 0
• Mol File: 106972-45-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DL-Glycerin-1-n-hexylether(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Glycerin-1-n-hexylether(106972-45-6)
• EPA Substance Registry System: DL-Glycerin-1-n-hexylether(106972-45-6)

Safety Data

• Hazardous Substances Data: 106972-45-6(Hazardous Substances Data)

Upstream product

• 96-24-2 3-monochloro-1,2-propanediol 
• 111-27-3 hexan-1-ol 
• 111-25-1 1-bromo-hexane 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 16224-24-1 1-chloro-3-hexyloxy-propan-2-ol 
• 106-70-7 methyl hexanoate 
• 56-81-5 glycerol 
• 66-25-1 hexanal 
• 142-62-1 hexanoic acid 
• 5926-90-9 hexyloxymethyloxirane 
• 90677-40-0 3-hex-1-en-t-yloxy-propane-1,2-diol 
• 502-53-4 2,3-dihydroxypropyl hexanoate 

Downstream Products

• 106881-93-0 C₃₅H₄₀O₃ 
• 106882-00-2 C₂₁H₃₈NO₆P 
• 106881-98-5 Phosphoric acid 2-benzyloxy-3-hexyloxy-propyl ester 2-bromo-ethyl ester 
• 92948-22-6 2-Benzyloxy-3-hexyloxy-propan-1-ol 
• 106881-90-7 1-Hexyloxy-3-trityloxy-propan-2-ol 

Relevant articles and documents

PROCESS FOR PREPARING A POLYOL ETHER

The present invention relates to a process for preparing a polyol ether of formula (I), comprising a step of reductive alkylation involving a compound of general formula (II) and a compound of general formula (III): in which R1, R2, R3 and R4 are as defined in claim 1.

1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: Catalytic reductive alkylation and transesterification/reduction

From available and bio-sourced methyl esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters or triolein and consisted of a first transesterification to the corresponding monoglyceride with a BaO/Al2O3 catalyst, then its reduction to the desired glycerol monoether with a recyclable heterogeneous catalytic system Pd/C and Amberlyst 35 under H2 pressure. In addition, a mechanism for the reaction was also proposed.

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.

Catalytic etherification of glycerol with short chain alkyl alcohols in the presence of Lewis acids

Here we report the homogeneously-catalyzed etherification of glycerol with short chain alkyl alcohols. Among the large variety of Bronsted and Lewis acids tested, we show here that metal triflates are not only the most active but are also capable of catalyzing this reaction with an unprecedented selectivity. In particular, in the presence of Bi(OTf)3, the targeted monoalkylglyceryl ethers were obtained with up to 70% yield. Although tested Bronsted acids were also capable of catalyzing the etherification of glycerol with alkyl alcohols, they were found however less active and less selective than Bi(OTf)3. By means of counter experiments, we highlighted that the high activity and selectivity of Bi(OTf)3 may rely on a synergistic effect between Bi(OTf)3 and triflic acid, a Bronsted acid that can be released by in situ glycerolysis of Bi(OTf)3. The scope of this methodology was also extended to other polyols and, in all cases, the monoalkylpolyol ethers were conveniently obtained with fair to good yields.

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.

POLYOL ETHERS AND PROCESS FOR MAKING THEM

New polyol ether compounds and a process for their preparation. The process comprises reacting a polyol, a carbonyl compound, and hydrogen in the presence of hydrogenation catalyst, to provide the polyol ether. The molar ratio of polyol to carbonyl compound in the process is greater than 5:1.

Acid-catalyzed etherification of glycerol with long-alkyl-chain alcohols

Rubbing the right way: The direct etherification of glycerol with long-chain alcohols typically suffers from poor contact between the reaction phases. A dodecylbenzene sulfonic acid catalyst enables a better contact between the glycerol and alcohol phases, enhancing the yield of monoalkyl glyceryl ethers and offering a direct route for the synthesis of these surfactants. Copyright

PROCESS FOR MAKING POLYOL ETHERS

The present invention generally relates to a process for making polyol ethers by reacting a polyol and a carbonyl compound together in the presence of hydrogen gas and a palladium hydrogenation catalyst on an acidic mesoporous carbon support.

POLYOL ETHERS AND PROCESS FOR MAKING THEM

New polyol ether compounds and a process for their preparation. The process comprises reacting a polyol, a carbonyl compound, and hydrogen in the presence of hydrogenation catalyst, to provide the polyol ether. The molar ratio of polyol to carbonyl compound in the process is greater than 5:1.

An efficient synthesis of glyceryl ethers: Catalyst-free hydrolysis of glycidyl ethers in water media

Hydrolysis of hydrophobic glycidyl ethers in pressurized water media afforded the corresponding glyceryl ethers in good to excellent selectivity within several minutes without catalyst.