The Synthetic Routes of 1,1′-(1,5-Pentanediyl) di-2-propenoate

The synthesis of 1,1′-(1,5-Pentanediyl) di-2-propenoate, commonly known as TMPD, is a crucial step in the production of a wide range of chemicals and materials in the chemical industry.
There are several synthetic routes available for the production of TMPD, each with its own advantages and disadvantages.
In this article, we will discuss the most commonly used synthetic routes for TMPD and their applications in the chemical industry.

1. The Rosenthal-Trost Route

The Rosenthal-Trost route is one of the most commonly used methods for the synthesis of TMPD.
This route involves the reaction of 1,5-pentanediol with acrylic acid in the presence of sodium hydroxide and dimethyl sulfoxide (DMSO) as a solvent.
The reaction produces TMPD as a colorless liquid with a mild odor.
This method is considered to be relatively simple and efficient, and the product can be easily purified by recrystallization.
The Rosenthal-Trost route is widely used in industrial production due to its high yield and low cost.

2. The Hydrolysis of Cyclohexene Oxide

Another common method for the synthesis of TMPD is the hydrolysis of cyclohexene oxide.
This reaction involves the treatment of cyclohexene oxide with water in the presence of a catalyst, such as sodium hydroxide or hydrochloric acid.
The reaction produces TMPD as a colorless liquid with a mild odor.
This method is also relatively simple and efficient, and the product can be easily purified by recrystallization.
The only disadvantage of this method is that it requires the use of a catalyst, which can increase the cost of production.

3. The Bischler-Napieralski Route

The Bischler-Napieralski route is another commonly used method for the synthesis of TMPD.
This route involves the reaction of 1,5-pentanediol with sodium hydroxide and dichloromethane as a solvent.
The reaction produces TMPD as a colorless liquid with a mild odor.
This method is considered to be more complex than the other two methods, but it is also more versatile and can be used to produce a wider range of chemicals and materials.

4. The Other Synthetic Routes

There are several other synthetic routes for the production of TMPD, such as the Ogawa-Colby route and the Sharpless/Evans route.
However, these routes are less commonly used in industrial production due to their complexity and high cost.

In conclusion, the synthesis of TMPD is a crucial step in the production of a wide range of chemicals and materials in the chemical industry.
There are several synthetic routes available for the production of TMPD, each with its own advantages and disadvantages.
The Rosenthal-Trost route, the hydrolysis of cyclohexene oxide, and the Bischler-Napieralski route are the most commonly used methods for the production of TMPD.
These routes are relatively simple, efficient, and cost-effective, making them the preferred methods for industrial production.