Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for producing polyhalogenated diamantane and derivative thereof

A technology of adamanttetradecane and adamanttetradecanediol, which is applied in the field of manufacture of polyhalogenated adamantatetradecanes and adamanttetradecane polyols, and can solve the problems of low reactivity, no progress, no transformation, etc. problem, to achieve the effect of low reactivity

Inactive Publication Date: 2010-05-05
TOKUYAMA CORP
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The second reason, based on common sense in chemistry, is that dichloroadamantotetradecanes have lower reactivity than dibromoadamantotetradecanes. The reaction of diols hardly proceeds, and adamantetetradecanediols cannot be obtained
[0012] In addition, there are no reports of the transformation of trihalogenated adamantinetetradecanes into adamantinetetradecanetriols.
[0013] Therefore, the reaction yields of the above-mentioned various production methods are low, and there are few polyhalogenated adamantinetetradecanes that can be adapted, so it can be said that they are not necessarily industrially advantageous methods.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for producing polyhalogenated diamantane and derivative thereof
  • Method for producing polyhalogenated diamantane and derivative thereof
  • Method for producing polyhalogenated diamantane and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0140] Under nitrogen flow, add 40 g of concentrated sulfuric acid (2 times the mass of adamantine tetradecane) and 1.5 g of sodium sulfate (0.0106 mol, 0.1 times the mole of adamantine tetradecane) into a 500 ml four-neck flask. Then 20 g (0.106 mol) of adamantine tetradecane was added, and stirred for 10 minutes while maintaining the suspended state at about 20°C. Then, 24.7 g (0.212 mol, 2 times mol of adamantinetetradecane) of chlorosulfonic acid was added slowly so that the reaction would not run out, and it stirred at 30 degreeC for 3 hours. The reaction solution after 3 hours was in a suspended state. As a result of analyzing the reaction solution by GC, it was found that the adamantinetetradecane used as raw materials was 74% by mass, the monochloroadamantatetradecane was 2% by mass, the dichloroadamantotetradecane was 22% by mass, and the trichloroadamantotetradecane was 2% by mass, the progress of the reaction came to a halt. Then, drop into chlorosulfonic acid 37....

Embodiment 2～4

[0143] Except that the amount of chlorosulfonic acid used in Example 1 was changed according to Table 1, the same operation was carried out. The results are shown in Table 1.

[0144] Table 1

[0145]

Embodiment 5

[0147] Operate and react in the same manner as in Example 1, and carry out aftertreatment. To the obtained crude product, 20 g of n-heptane (one time the mass of the raw material adamantinetetradecane) was added, followed by heating and reflux for 2 hours. Liquids are often in suspension. Then, it was cooled to 5° C., stirred for 5 hours and matured, and the solid was filtered to obtain 22 g (containing 96% of dichloroadamantyl tetradecane) of a white solid, with a yield of 78% (based on adamantine tetradecane).

[0148] The obtained dichloroadamantotetradecane is almost selectively 4,9-dichloroadamantotetradecane. figure 1 shows the nuclear magnetic resonance (NMR) spectrum of the proton, figure 2 The nuclear magnetic resonance (NMR) spectrum of carbon is shown.

[0149] MASS (EI): molecular weight 256 (M + )

[0150] 1 H-NMR spectrum (TMS reference): δ2.10 (H a , s, 12H), δ1.96(H b , s, 6H)

[0151] 13 C-NMR spectrum (TMS reference): δ66.2 (C a ), δ46.7(C b ), δ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Disclosed is a method for producing polyhalogenated diamantanes which is characterized by reacting diamantanes with a halosulfonic acid. Also disclosed is a method for producing diamantane polyols which is characterized in that the polyhalogenated diamantanes obtained by the above-described method are reacted with water in the presence of a water-soluble organic solvent and a carboxylate.

Description

technical field [0001] The present invention relates to a method for producing polyhalogenated diamantanes and adamantanetetradecane polyols, which are suitable as raw materials for the production of functional materials and electronic materials. Background technique [0002] The adamantane derivative has a skeleton similar to that of the adamantane derivative. Since adamantane derivatives have excellent heat resistance and high transparency, adamantane tetradecane derivatives with a similar skeleton are also expected to be used in high-functional materials such as heat-resistant polymers or semiconductors that require transparency. Used in the raw materials of electronic materials such as photoresist. Among the adamantinetetradecane derivatives, polyhalogenated adamantotetradecanes are important compounds used as starting materials in the production of various adamantotetradecane derivatives. [0003] As a method for producing polyhalogenated adamantinetetradecanes, a met...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/10C07C23/46C07C29/124C07C35/44C07B61/00
CPCC07C23/46C07C29/124C07C2103/90C07C17/10C07C2603/90C07C35/44C07B61/00
Inventor 前原孝之山口真男
Owner TOKUYAMA CORP