1,1-diethoxyethane (1,1-diethoxyethane) is just one of the primary downstream items of ethanol, which has the advantages of low poisoning, excellent solubility, and also low boiling point; it is very important for the synthesis of carbonyl substances such as ketones and aldehydes intermediates. At the same time, 1,1-diethoxyethane has good miscibility with diesel oil and has superb burning efficiency. It can change ethanol as the oxygen-containing addition element of biomass in diesel oil, which can significantly decrease the discharge of particulates and also NO, as well as raise the amount of cetane worth, is a possible premium gas and also gas additive.
0.831 g/mL at 25 °C(lit.)
4.1 (vs air)
20 mm Hg ( 20 °C)
Store at +2°C to +8°C.
at 1.00 % in propylene glycol. ether green nut earthy sweet vegetable
46 g/L (25 ºC)
1,1-Diethoxyethane is a new type of top-quality spice and an essential artificial intermediate, commonly made use of in cosmetics, food and various other additive industries and also natural synthesis.
1,1-diethoxyethane can be used as a solvent, and additionally made use of in the synthesis of dyes, plastics, scents and the natural synthesis of secured aldehyde teams.
1,1-diethoxyethane is made use of as an important alcohol additive, as a solvent, as well as additionally utilized in the synthesis of dyes, plastics, and seasonings.
1,1-diethoxyethane GB 2760-1996 states that it is allowed to be utilized in food spices.
1. Acetal as a solvent
The chemical stability as well as decreased density of 1,1-Diethoxyethane determine that it can be utilized as a solvent with exceptional efficiency in different chemical treatments such as elimination, dilution as well as recrystallization. Considering that acetal is immiscible with water, when it is utilized as a solvent medium in chemical handling, much less waste fluid in addition to drainage are produced during recycling, which boosts the environmental management benefits as well as economical performance of the dealing with treatment. Considered that acetal has a freezing point as lowered as -66 ° C as well as also a boiling point as high as 88 ° C, its operating temperature level array is suitable for many chemical treatments. For that reason, acetal is a feasible new generation of industrial natural solvents, which may replace the existing tetrahydrofuran (THF), ethyl acetate, methylene chloride, toluene, 1,4-dioxane, methyl tertiary Organic solvents such as butyl ether, ethylene oxide along with other ethers (see Table 2). Acetal is made use of as a commercial organic solvent. It has the features of broad application selection, risk-free safety and also safety and also very easy operation.
1.1 Solvents in organic synthesis
Contrasted to various other ether solvents (such as THF), the biggest distinction in between 1,1-Diethoxyethane is that acetal has water immiscibility as well as additionally its non-hygroscopic residential or commercial properties. Acetal can be made right into a very entirely dry product (water product is just 100-150 × 10-6, as well as the peroxidation prevention BHT is only 100 × 10-6). This product can still be used directly after being subjected inside for one year. In water-sensitive organometallic reactions (no additional drying out is called for as it is non-hygroscopic). Nonetheless, the “anhydrous” grade THF utilized as a solvent for organometallic responses must be saved in an inert gas Ar gas for moisture-proof storage area. In -NaH as a basic energizer, 3-butyn-1-alcohol is implemented benzylation with benzyl bromide to prepare 1-benzyloxy-3-butyne (scent intermediate) in the reaction, use acetal to do The reaction solvent is better than THF, the previous does not take in water, that makes the item splitting up less complicated. In the process of preparing 1-phenyl-l-butanol (medicine intermediate) from benzaldehyde as well as n-butyllithium, acetal is used instead of THF as the reaction solvent, not only the thing splitting up is less complex, yet additionally the conversion of the feedback The rate can furthermore be enhanced by 5-10%. Methylmagnesium chloride and benzaldehyde manufacture 1-phenyl-1-ethanol (a spices, furthermore called styrol) is a common Crignard reaction, if acetal is used as reaction solvent in its process, item splitting up also calls for Much less difficult than when making use of THF as solvent.
In all the organometallic reactions checked out, making use of acetal as the action solvent amounted or much better than anhydrous grade THF solvent. It has in fact been located that dialkyl lithium cuprate militarized conjugate enhancement response, palladium militarized allylation action, rare-earth element militarized hydrogenation action as well as enzyme catalyzed numerous esterification responses can be utilized Aldehyde is taken advantage of as an action solvent, and the effect will be better.
1.2 New power ingredients
1,1-Diethoxyethane is an actually valuable solvent in anhydrous lithium batteries as well as anhydrous aluminum batteries. Compared with other ether solvents, it is discovered that acetal has little adjustment in battery voltage, can hinder the fragmentation of electrodes as well as electrolytes, as well as can make The battery can be recharged extra times.
Researchers from FMC Company of the United States heated NaAlH as well as likewise LiCl with each other in an acetal solvent from 25 ° C to the boiling reflux temperature level of acetal up until the action was complete. LiAlH items can be straight created through metathesis in one step171. Japanese scholars have produced a low-pollution methanol-based automotive gas. This gas consists of 3 sorts of components:
( 1) Methanol;
( 2) substantial gas, as well as the weight ratio of (1 )/( 2 )= 2 ～ 5; ( 3) 2 or perhaps a lot more ingredients (containing acetal, diethoxyethane along with MTBE, and so on). The alcohol-based gas compounded by doing this presents reduced carbon monoxide, HC and also NO when utilized as an environmentally friendly automobile gas. Exhaust discharges and also this gas is additionally secure in storage room at reduced temperature levels without stage separation. This gas has a higher octane score.
3. Handling assistance for materials and also layers
1,1-Diethoxyethane is an outstanding solvent for preparing phenolic material adhesives, urea-formaldehyde product adhesives as well as neoprene adhesives. This sort of adhesive has decreased viscosity, strong infiltration, excellent cleaning efficiency, consistent storage room and also a lot longer trusted life span. In addition to that, acetal can be made use of in covering additives generally utilized in auto layers. In peroxyethylene paint thinner, acetal can alter harmful benzene thinner.
1,1-Diethoxyethane is made use of as an end-capping representative in the manufacturing of polyoxymethylene material, which can not just enhance the thermal security of polyoxymethylene, but also boost the yield of resin products. For instance, researchers from Ticona Firm in Germany liquified 0.2 X 10 West (according to the weight of trioxane monomer used) trifluoromethanesulfonic acid in 500 × 10-6 acetal, in addition to added it to 96. In a combined monomer composed of 6% trioxane as well as 3.4%– oxolane, polymerize at 80 ° C to acquire a copolymerized acetal product. The unsaturated incurable team consisted of in this polymer particle is exceptionally tiny, simply 0.04%, as well as its thaw thickness coefficient is 2.5 ml/10cmm.
2. Acetal as response reagent
2.1 as ethoxymethylation reagent
Acetals are truly favorable for the ethoxymethylation of alcohols, phenols along with amines due to the existence of two oxygens. Typical ethoxymethylation reagents include chloromethyl ethyl ether, yet it is damaging under alkaline problems, while acetal is safe and additionally safe as an ethoxymethylation reagent under acidic chauffeur conditions The normal ethoxymethylation reaction is as adheres to:
2.2 As an equivalent to formaldehyde
1,1-Diethoxyethane is a secured sort of formaldehyde, which can be used as a substitute for anhydrous formaldehyde to make the action much more protected. For example, acetal, like CH20, can be used as a methylene reagent, and the typical response it has really analyzed is as follow:
1. The synthesis of 6-methylene-substituted steroidal spin-offs, which are expected to be utilized as anticancer medicines in the future, can be prepared by reacting the parent with acetal under the catalysis of POCl.
2. Dihydrocarbyl phenol or trihydrocarbyl phenol with steric limitation reacts with acetal under acidic issues to develop dimers and also polymers. These polymers are anemic in addition to safe, and additionally can be used as rubber, plastic low volatility anti-oxidant.
3. Diphenylcarbamate can be prepared by responding phenylcarbamate with acetal under the catalysis of excess acid.
4. Using acetal as a reagent can manufacture dihydroisoflavone by-products in one action.
1. Dichloromethane method This method is an earlier method for the synthesis of diethoxymethane. The reaction not only requires sodium ethoxide as a reagent, but also requires anhydrous operation, and the low yield limits its development.
2. Dimethyl sulfoxide method Dimethyl sulfoxide is unstable to acid, and it is heated and decomposed to form formaldehyde, which is added to ethanol to obtain acetal. Due to the large amount of dimethyl sulfoxide and the low yield, it is not conducive to large-scale production.
3. Calcium chloride method The reaction yield is good, but the reaction time is long and the post-processing is inconvenient.
4. Acid-catalyzed method This method is simple in operation, short in reaction time and high in yield, and is an ideal preparation method.
5. Researchers from Germany’s Ticona company developed a process for preparing acetal by catalytic acetal billion, combining reactive distillation and extractive distillation in a distillation tower, and obtaining high-quality acetal from the condensation reaction of aldehydes and alcohols Acetal product with high product concentration and high product yield. Its disposable product concentration (acetal content) is >90%.
The inner diameter of the reaction/distillation tower is 350mm, which consists of a material heating zone (including the 1st and 2nd sections), a reaction/distillation zone (including the 3rd, 4th and 5th sections), and an extractive distillation zone (the 6th section) consists of three parts. In the reaction, Kata-pak components (produced by SulzerChemtech, Germany) are installed in the 3rd, 4th and 5th sections of the distillation zone, and these components are filled with a small bag of a small bag of acidic ion exchange resin catalysts to form three condensations. Hydroformylation catalytic fixed bed. The same acidic ion exchange resin catalyst is also installed in the prereactor. The alcohol/aldehyde condensation reactant conversion rate in the prereactor is 15% to 40%. The extractant is actually deionized water, and its reflux ratio is between 2 and 6. The total conversion rate of alcohols forming acetal can reach more than 95%, and the acetal content in the crude acetal product obtained from the reaction is more than 98%. After the crude product is subjected to further low boiler removal distillation and extractive rectification, a high-purity acetal product with a product purity of 99.9% can be obtained.
Taking the production of methylal CH:(OCH,): as an example, 20% formaldehyde aqueous solution is fed into the pre-reactor together with 100 kg/h methanol at a feed rate of 280 kg/h, and the reaction temperature of the pre-reactor is controlled. Pre-reformation was carried out at about 80°C, and the composition of the reaction effluent was 19.5% methanol, 11.5% formaldehyde, 8% methylal and 61% water, corresponding to a methanol pre-reformation rate of 26%. Send 120kg/h low-pressure steam (temperature 100°C) to the bottom of the reaction/distillation tower for heating, so that the temperature of the Katapak catalytic bed is maintained at 50°C, and the temperature at the top of the tower is maintained at 46°C. The reaction mixed liquid flowing out from the pre-reactor is sent to the reaction/distillation column through a distributor between the 4th and 5th sections of the reaction/distillation zone for further acetalization conversion. At the same time, between the 5th and 6th sections of the reaction/distillation tower, 100kg/h of deionized water (extractant) is fed through a disc distributor. Condensate all the gaseous substances from the reaction/distillation tower, and circulate 500kg/h of the distillate back to the top of the tower for reflux treatment, and the remaining 110kg/h of the distillate is used as the crude methylal product liquid take out. The composition of its crude methylal product liquid is 98.2% methylal. 4% methanol, 0.8% water and 0.6% methyl formate. The outflow of the reaction/distillation tower liquid is 380kg/h, which contains 1% methanol and 4% formaldehyde, and the rest is water. The overall conversion of methanol was 95.5%. The crude methylal product liquid is further distilled to remove low boilers, and after extraction and rectification purification treatment with ethylene glycol, a pure methylal product with a purity of >99.9% can be obtained, wherein the methanol content is < 100×10-6.
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