JPS5879970A - Propiolic acid ester - Google Patents

Abstract

NEW MATERIAL:2-(p-Chlorophenylthio)ethyl propiolate of the formula. USE:Water life repellent, fungicide: it is dispersed in water in the form of an emulsion or wettable dust or coated after it is mixed in a paint. The resultant water life repellent shows improved antidecaying properties and bad smelling of the materials coated therewith and improved toxicity to human. PREPARATION:The reaction of propiolic acid with 2-(p-chlorophenylthio)ethanol is conducted in an organic solvent such as benzene in the presence of an acid catalyst such as p-toluenesulfonic acid to give 2-(p-chlorophenylthio)ethyl propiolate of the formula.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to fatty acid propionic acid ester compounds.

Currently, the bottoms of ships, fishing nets, buoys, and other equipment placed in seawater, underwater structures such as dam affixing facilities, and water intake channels for condenser cooling water in thermal power plants are constantly in contact with seawater. Mourning 5
VC includes seaweed and shellfish such as blue-green lettuce, sea lettuce, seaweed, fujibo, mussel, and sea squirt, as well as freshwater irrigation ponds, ornamental fish ponds, and cooling 4.
In order for the algae of Aomidoro and Hoshimidoro to propagate,
Economic losses and aesthetic defects are caused by ornamental pyroelectricity.

For example, on a ship, not only does it cause an increase in cruising speed and fuel consumption, but also economic losses due to the cost of cleaning the bottom of the ship or the suspension of operations during this cleaning period. It's a thing.

In underwater structures, handling operations become inconvenient. Water intakes, heat exchangers, etc. (/J In water intakes, water intake capacity decreases, cooling efficiency decreases, or desorption occurs.
This is the cause of the lower performance of mechanical species than biomass.

Aquaculture fishing nets [Examples of minor losses caused by the proliferation of shellfish algae, such as oxygen deprivation, fish mortality due to internal air, and decreased survival rate, are common.

(1) J: In order to prevent problems caused by the propagation of eel seawater and freshwater harmful organisms,
Shichiki tin compounds such as tribunal tin oxide, organic chlorine compounds centered on pentachlorophenol,
Organic sulfur thread compounds such as menalembisiosilinate are used in paints, etc., and cooling water σ) is used.
In the intake canal, the salt-watered water was cooled down through the surface waterway.

However, these traditional aquatic biorepellents.

Although it may be effective depending on the purpose or season,
It corrodes the coating material. Or, in practical use, the odor was not necessarily satisfactory in terms of toxicity to the human body, etc. The Ministry of Invention and others decided to combine each building in order to solve this problem.
As a result of synthesizing I, preparing its offspring to prevent biological adhesion, and conducting extensive research, we discovered that it is a propiol-intoxicated ester compound, a novel compound that is used as a propiol-drinking ester compound, and has not yet been published in any literature. He discovered something and perfected his invention.

Book @ Ming's #Ki propiolic acid ester compound.

It is indicated by.

The novel brohyalic acid ester compound of the present invention is an organic bath compound.
In the presence of an acid catalyst, propiolic acid and 2-(p-90lov, nilthio)ethanol and ? It is synthesized by reacting i-&.

The novel compound of the present invention can be used as an aquatic organism repellent, an orchid control agent, and the like.

In order to use the novel compound W of the present invention as an aquatic organism repellent, it can be dispersed in water as an emulsion or a hydrating agent, or it can be coated containing a material.

I can use it for convenience.

An example will be described below.

Example 1 (Synthesis Example) Synthesis of 2-(p-chlorophenylthio)ethyl-propiolade
Equip a 200 d reaction flask with a 2-(
p-chlorophenylthio)ethanol 6P (0,0
5 mol), propiolic acid 222 (003 mol), p-1
Add luenesulfonic acid θ5P and benzene 100m/
? # case, 5 o'clock reaction under reflux 〇After 1 heart, BI
M> The monk washed the liquid with water, dried it, and shrunk it.

By vacuum evaporation, 2-(p-chlorophenylthio)ethyl-propiolade (colorless liquid, 8 points 121-126)
"010.2tmHJ)5.2? (Yield 4
4 Subb) No, no.

Former Murasaki Analysis (Military Quantity Section) OH O,, H, Oノ, 0. Calculated value as S 54,
89 3.77 Analysis value
55.08 362 Example 2 11 female offspring hatched within 48 hours (7 Arte
Dispense mia in 1012!4 portions and get 19CG with 1 artificial seawater
shall be.

Leave this in a glass petri dish [$L, :) 4 o'clock...1.

In advance, 2% of the developed compound, 90% of tuclohexanone,
The emulsion prepared in Tween-808 was diluted with artificial seawater to the same degree as F9T, and 1 ml of this was added to a petri dish to make the concentration of 10 ppm in the water surrounding Artemia. For cctr, 1!6 per ward
Make one petri dish. Cover the petri dish and place it in a thermostatic room at 20°C.

After 24 hours, the survival rate of Artemia f7) was examined. The results were judged based on the following criteria.

A Mortality rate 100% B 190-99% 0 〃 80-89% D Mortality rate 50-79% E O-49 The results are shown in the following table 1-0 Test compound Compound of the present invention A

Claims (1)

[Claims] propiolic acid ester compound.