JP3206844B2 - Purification method of non-aqueous organic solvent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for purifying a non-aqueous organic solvent. More specifically, dehydration of water, thiol or amine compounds contained in the non-aqueous organic solvent,
It relates to a method for desulfurization and deamine.

[0002]

2. Description of the Related Art Conventionally, as a method for purifying a non-aqueous organic solvent, a method such as simple distillation or extractive distillation has been mainly used. In a special case, a method of adding an adsorbent such as a molecular sieve, metallic sodium or the like and performing distillation has been used.

[0003]

However, it is difficult to remove trace water in a non-aqueous organic solvent and thiol or amine compounds having a boiling point close to that of the non-aqueous organic solvent at once and with high precision. there were. Also, it was extremely difficult to remove a trace amount of water.

An object of the present invention is to provide a method for removing water and thiol-based or amine-based compounds in a non-aqueous organic solvent at once and with high accuracy in order to solve the problems of the prior art. .

[0005]

Means for Solving the Problems In order to achieve the above object, a method for purifying a non-aqueous organic solvent according to the present invention comprises: adding a silyl compound containing a plurality of halogen groups to a non-aqueous organic solvent; The water contained in the non-aqueous organic solvent is reacted with a thiol-based compound or an amine-based compound to form a siloxane compound, and then the siloxane compound and unreacted silyl compound are separated from the non-aqueous organic solvent. It is provided with a configuration of removing.

In the above construction, the silyl compound containing a plurality of halogen groups is composed of SiCl ₄ , SiHCl ₃ , S
iH ₂ Cl ₂ and SiCl ₃ O (SiCl ₂ O) _n S
It is preferably at least one selected from iCl ₃ (n is 0 or an integer).

[0007] The amount of the silyl compound to be added may be an appropriate amount necessary for removing water, thiol or amine compounds contained in the non-aqueous organic solvent.

[0008]

According to the present invention, when water, a thiol-based or an amine-based compound is contained in a non-aqueous organic solvent, a silyl compound containing a plurality of halogen groups (for example, chloro group) is added and mixed. By water or thiol,
Alternatively, the active hydrogen of the amine compound and the halogen group of the silyl compound cause a dehydrohalogenation reaction. For example, when a chlorosilyl compound is used, a dehydrochlorination reaction occurs to generate a siloxane compound and hydrochloric acid. In this state, the siloxane compound and hydrochloric acid can be easily separated from the non-aqueous solvent by distillation or filtration, and the water and thiol or amine compounds in the non-aqueous organic solvent can be separated and removed very easily. There is.

Further, the silyl compound containing a plurality of halogen groups may be selected from SiCl ₄ , SiHCl ₃ , SiH ₂ Cl ₂ ,
And at least one selected from SiCl ₃ O (SiCl ₂ O) _n SiCl ₃ (n is 0 or an integer),
It is preferable because many functional groups contribute to the reaction and siloxane after the reaction is easily separated and removed.

[0010]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Embodiments will be described below in order. In the following examples,% means% by weight unless otherwise specified.

Example 1 As a non-aqueous organic solvent, for example, n-decane (a non-aqueous organic solvent containing no active hydrogen, for example, petroleum benzene, n-hexane, benzene, toluene, xylene, ether, gasoline, kerosene) Etc.)
kg, and 4 g of SiCl ₃ OSiCl ₃ was added as a silyl compound containing a plurality of chloro groups, and the mixture was thoroughly stirred. At this time, the water contained in the n-decane was subjected to a dehydrochlorination reaction with SiCl ₃ OSiCl ₃ as shown in the following formula (Formula 1) to generate a hydrochloric acid gas and a siloxane compound.

[0012]

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The thiol-based SH group undergoes a dehydrochlorination reaction with the SiCl group, and as shown in the following formula (2), hydrochloric acid and S
An i-S bond was generated and fixed to the siloxane compound.
In the following formula (Formula 2), R represents an alkyl group.

[0014]

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The NH group and NH ₂ group of the amine compound were also dehydrochlorinated with the SiCl group to generate hydrochloric acid and a Si—N bond, and were fixed to the siloxane compound. In the following formula (Chemical formula 3), R ¹ and R ^{2 each} represent hydrogen or an alkyl group. In the case of an alkyl group, R ¹ and R ² may have a cyclic structure (cycloalkyl group).

[0016]

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As described above, dehydration, desulfurization, and deamination could be performed. Next, distillation at around 145 ° C.
Hydrochloric acid could be removed as vapor, and the siloxane compound could easily be removed as evaporation residue due to its high boiling point.

When a relatively large amount of water is contained as an impurity, a high-molecular-weight polysiloxane compound is produced, and thus it was possible to separate the solution by centrifugation or filtration.

Example 2 An experiment was conducted in the same manner as in Example 1 except that kerosene was used instead of n-decane as the non-aqueous organic solvent and the distillation temperature was 175 to 325 ° C. As a result, thiol-based and amine-based compounds causing nitrogen oxides and sulfur oxides could be almost completely removed.

In the above embodiment, a plurality of chlorosilicone
As a substance containing a silyl group, SiCl_ThreeOSiCl_ThreeTo
Used, but SiCl_FourOr SiHCl_Three, SiH_Two
Cl _Two, SiCl_ThreeO (SiCl_TwoO)_nSiCl
_Three(N is 0 or an integer, preferably 0 to 20)
It was possible. In particular, SiCl_ThreeO (SiCl_Two
O)_nSiCl_Three(Preferable n is an integer of 2 to 20)
Points are high and stable, making them easier to handle than others.
Was.

As described above, according to the embodiment of the present invention, a silyl compound having a plurality of chloro groups is added to a non-aqueous solvent and mixed with water, a thiol compound or an amine compound contained therein. To produce a polysiloxane compound, then separating the polysiloxane compound and unreacted substances containing a plurality of chlorosilicyl groups,
Purify the non-aqueous organic solvent. Dehydration, desulfurization and deamination of water, thiol or amine compounds contained in non-aqueous organic solvents.

[0022]

As described above, the method according to the present invention comprises:
Water and thiol or amine compounds contained in non-aqueous organic solvents can be easily and efficiently separated and removed. That is, when water, a thiol-based or an amine-based compound is contained in a non-aqueous organic solvent, water, a thiol-based compound, or Active hydrogen of the amine compound and the halogen group of the silyl compound cause a dehydrohalogenation reaction. In this state, the siloxane compound and hydrochloric acid can be easily separated from the non-aqueous solvent by distillation or filtration, and the water and thiol or amine compounds in the non-aqueous organic solvent can be separated and removed very easily. There is.

Further, the silyl compound containing a plurality of halogen groups is SiCl ₄ , SiHCl ₃ , SiH ₂ Cl ₂ ,
And at least one selected from SiCl ₃ O (SiCl ₂ O) _n SiCl ₃ (n is 0 or an integer),
It is preferable because many functional groups contribute to the reaction and siloxane after the reaction is easily separated and removed.

──────────────────────────────────────────────────続 き Continued on the front page (58) Fields investigated (Int. Cl. ⁷ , DB name) C10G 29/02-29/20 C10G 29/20 C07B 63/00 C07C 7/148 WPI / L (QUESTEL)

Claims (2)

(57) [Claims] 1. A non-aqueous organic solvent to which a silyl compound containing a plurality of halogen groups is added and mixed, and reacted with water, a thiol-based compound or an amine-based compound contained in the non-aqueous organic solvent. A non-aqueous organic solvent, wherein the siloxane compound and the unreacted silyl compound are separated and removed from the non-aqueous organic solvent. 2. The method according to claim 1, wherein the silyl compound containing a plurality of halogen groups is at least one selected from SiCl ₄ , SiHCl ₃ , SiH ₂ Cl ₂ , and SiCl ₃ O (SiCl ₂ O) _n SiCl ₃ (n is 0 or an integer). Claim 1 which is one
3. The method for purifying a non-aqueous organic solvent described in 1. above.