JPH0466588A - Manufacturing method of Texyltrichlorosilane - Google Patents
Manufacturing method of TexyltrichlorosilaneInfo
- Publication number
- JPH0466588A JPH0466588A JP2172449A JP17244990A JPH0466588A JP H0466588 A JPH0466588 A JP H0466588A JP 2172449 A JP2172449 A JP 2172449A JP 17244990 A JP17244990 A JP 17244990A JP H0466588 A JPH0466588 A JP H0466588A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- group
- thexyltrichlorosilane
- mol
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
［産業上の利用分野コ
本発明はテキシルトリクロロシランの製造方法、特には
シリコーン樹脂の原料として、また無機物質の表面処理
剤や錯体触媒の添加剤として有用とされるテキシルトリ
クロロシランの製造方法に関するものである。[Detailed Description of the Invention] [Industrial Field of Application] The present invention relates to a method for producing thexyltrichlorosilane, which is particularly useful as a raw material for silicone resins, and as a surface treatment agent for inorganic substances and as an additive for complex catalysts. The present invention relates to a method for producing thexyltrichlorosilane.
［従来の技術］
ＣＨ，ＣＨ３
式Ｈ−Ｃ−Ｃ−Ｓ ｉ ＣＲ、で示されるテキシルトリ
クＣＨ，ＣＢ。[Prior Art] CH,CH3 Textiltric CH,CB represented by the formula H-C-C-S i CR.
ロロシランはシリコーン樹脂原料、無機物質の表面処理
剤、錯体触媒の添加剤として使用されているものであり
、最近は特殊なシリル化剤としても有望視されている。Rorosilane is used as a raw material for silicone resins, as a surface treatment agent for inorganic substances, and as an additive for complex catalysts, and has recently been seen as promising as a special silylation agent.
そして、このものはヒドロシランに２．３−ジメチル−
２−ブテンを付加させるという方法で製造されているが
、この製造法についてはつぎの方法が公知とされている
。And this one is hydrosilane with 2,3-dimethyl-
It is manufactured by adding 2-butene, and the following method is known as this manufacturing method.
ｌ）過酸化ジアセチルの存在下で反応させる方法［Ｊ、
Ａｍ、Ｃｈｅｍ、Ｓｏｃ、７０．４８４（１９４８）］
２）極高温高圧下に無触媒で反応させる方法［Ｃｈｅｍ
、Ｌｉ５ｔｙ、５２．６４０（１９５８）］、３）触媒
としての塩化アルミニウムの存在下で反応させる方法［
Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔ、、２６．５５１１
（１９８５）］、
４）白金、ニッケル、パラジウムなどの遷移金属錯体の
存在下で反応させる方法。l) Method of reacting in the presence of diacetyl peroxide [J,
Am, Chem, Soc, 70.484 (1948)]
2) Method of reaction without catalyst at extremely high temperature and high pressure [Chem
, Li5ty, 52.640 (1958)], 3) A method of reacting in the presence of aluminum chloride as a catalyst [
Tetrahedron Lett, 26.5511
(1985)], 4) A method of reacting in the presence of a transition metal complex such as platinum, nickel, or palladium.
Ｅ発明が解決しようとする課題〕
しかし、この公知の方法については、上記したｌ）の方
法には過酸を使用するために危険である、２）の方法に
は極高温、高圧が必要であるし、この］）、２）の方法
では目的とするテキシルトリクロロシランの収率が５０
〜６０％で必ずしもよくないという不利があり、３）の
方法にはここに使用されるヒドロシランがジメチルクロ
ロシラン、ブチルメチルクロロシランのような有機クロ
ロ水素含有シランに限定され、無機のトリクロロシラン
では反応しないという不利があり、４）の方法にはオレ
フィンの異性化が生じてテキシル基の導入が難しくなる
という欠点があり、いずれの方法も満足すべきものでは
ない。[Problem to be solved by the invention] However, regarding this known method, method 1) is dangerous because it uses peracid, and method 2) requires extremely high temperature and high pressure. However, in method 2), the yield of the desired thexyltrichlorosilane is 50%.
There is a disadvantage that 60% is not necessarily good, and the hydrosilane used here is limited to organic chlorohydrogen-containing silanes such as dimethylchlorosilane and butylmethylchlorosilane, and does not react with inorganic trichlorosilane. However, method 4) has the disadvantage that olefin isomerization occurs, making it difficult to introduce thexyl groups, and neither method is satisfactory.
［課題を解決するための手段］
本発明はこのような不利を解決したテキシルトリクロロ
シランの製造方法に関するものてあり、これはトリクロ
ロシランと２．３−ジメチル−２−ブテンとを式Ｒ−Ｎ
＝Ｎ−Ｒ（ここにＲはアルキル基、アルキルシアノ基、
アルキルエーテルシアノ基、環状アルキルシアノ基から
選択される基）で示される触媒としてのアゾ化合物の存
在下で反応させることを特徴とするものである。[Means for Solving the Problems] The present invention relates to a method for producing thexyltrichlorosilane that solves the above-mentioned disadvantages. N
=NR (where R is an alkyl group, an alkylcyano group,
The method is characterized in that the reaction is carried out in the presence of an azo compound as a catalyst represented by a group selected from an alkyl ether cyano group and a cyclic alkyl cyano group.
すなわち、本発明者らはテキシルトリクロロシランの効
果的な製造方法を開発すべく種々検討した結果、トリク
ロロシランと２．３−ジメチル−２−ブテンとの反応時
に触媒として式Ｒ−Ｎ＝Ｎ−Ｒ（Ｒは前記したとおり）
で示されるアゾ化合物を使用すると、この反応が比較的
温和な条件下に容易に進行し、目的とするテキシルトリ
クロロシランを殆んど定量的に高収率で得ることができ
ることを見出して本発明を完成させた。That is, as a result of various studies aimed at developing an effective method for producing thexyltrichlorosilane, the present inventors found that the formula R-N=N was used as a catalyst during the reaction between trichlorosilane and 2,3-dimethyl-2-butene. -R (R is as described above)
We have discovered that this reaction can easily proceed under relatively mild conditions and the desired thexyltrichlorosilane can be obtained in high yield almost quantitatively by using the azo compound shown by Completed the invention.
以下にこれをさらに詳述する。This will be explained in further detail below.
［作用］
本発明はトリクロロシランと２，３−ジメチル２−ブテ
ンとをアゾ化合物の存在下で反応させてテキシルトリク
ロロシランを製造する方法に関するものである。[Function] The present invention relates to a method for producing thexyltrichlorosilane by reacting trichlorosilane and 2,3-dimethyl-2-butene in the presence of an azo compound.
ロロシランがトリクロロシランのようなヒドロシランと
２，３−ジメチル−２−ブテンとの反応により製造され
ることは従来公知とされるところであるが、本発明はこ
の反応をアゾ化合物を触媒として反応させて目的とする
テキシルトリクロロシランを高収率で得ようとするもの
である。It is conventionally known that lorosilane is produced by the reaction of a hydrosilane such as trichlorosilane and 2,3-dimethyl-2-butene, but the present invention proposes a method in which this reaction is carried out using an azo compound as a catalyst. The objective is to obtain the desired thexyltrichlorosilane in high yield.
本発明におけるトリクロロシランと２．３−ジメチル−
２−ブテンとの反応は従来公知の方法に準じて行えばよ
く、したがってこれは２．３−ジメチル−２−ブテン１
当量に対してトリクロロシランを１〜１０当量、好まし
くは１．１〜５当量添加し、３０〜１５（１℃、好まし
くは３０〜１１０℃で反応させればよい。Trichlorosilane and 2,3-dimethyl- in the present invention
The reaction with 2-butene may be carried out according to a conventionally known method; therefore, this reaction is 2,3-dimethyl-2-butene
1 to 10 equivalents, preferably 1.1 to 5 equivalents, of trichlorosilane may be added to the equivalent amount, and the reaction may be carried out at 30 to 15°C (1°C, preferably 30 to 110°C).
本発明で触媒として使用するアゾ化合物は式Ｒ−Ｎ＝Ｎ
−Ｒで示され、Ｒがメチル基、エチル基、１，１，３．
３−テトラメチルブチル基などのアルキル基、シアノメ
チル基、シアノエチル基、１−シアノ−１−メチルエチ
ル基、１−シアノ−１−メチルプロピル基などのアルキ
ルシアノ基、１−シアノ−１，３−ジメチル−３−メト
キシブチル基などのアルキルエーテルシアノ基、１−シ
アノ−シクロヘキシル基などの環状アルキルシアノ基か
ら選択されるものとされるが、これには下記のものが例
示される。The azo compound used as a catalyst in the present invention has the formula R-N=N
-R, where R is a methyl group, an ethyl group, 1,1,3.
Alkyl groups such as 3-tetramethylbutyl group, alkylcyano groups such as cyanomethyl group, cyanoethyl group, 1-cyano-1-methylethyl group, 1-cyano-1-methylpropyl group, 1-cyano-1,3- It is selected from alkyl ether cyano groups such as dimethyl-3-methoxybutyl group and cyclic alkyl cyano groups such as 1-cyano-cyclohexyl group, and the following are exemplified.
Ｃ）１３ ＣＨ３
ＣＨ３ＣＨ２−Ｃ−Ｎ−Ｎ−Ｃ−ＣＨ２ＣＨ３ＣＮ
ＣＮ
ＣＨ３ＣＨ。C) 13 CH3 CH3CH2-C-N-N-C-CH2CH3CN
CN CH3CH.
ＣＨ３ＣＨｓ ＣＨｓ ＣＨ３ＣＨｓ”−
Ｃ−ＣＨ２−Ｃ−Ｎ−Ｎ−Ｃ−ＣＨ２−Ｃ−ＣＨ３Ｃ）
１３ Ｃ８３Ｇ）１３ ＣＨｓＣＮ
Ｎに
のアゾ化合物の添加量はここに使用される２、３−ジメ
チル−２−ブテンに対して０．１モル％以下では反応速
度が極めて遅いし、５０モル％より多くすると経済的に
不利となるので０．１〜５０モル％の範囲とすればよい
が、反応速度や収率の点からは０．１〜１０モル％とす
ればよく、これによれば前記したような温度条件で略々
定量的に反応を行なわせることができるので目的とする
テキシルトリクロロシランを収率９５〜９８％という高
率で得ることができる。CH3CHs CHs CH3CHs"-
C-CH2-C-N-N-C-CH2-C-CH3C)
13 C83G) 13 CHsCN
If the amount of the azo compound added to N is less than 0.1 mol % based on the 2,3-dimethyl-2-butene used here, the reaction rate will be extremely slow, and if it is more than 50 mol %, it will be economically disadvantageous. Therefore, the range may be from 0.1 to 50 mol%, but from the viewpoint of reaction rate and yield, it may be from 0.1 to 10 mol%, and according to this, under the temperature conditions mentioned above, Since the reaction can be carried out almost quantitatively, the desired thexyltrichlorosilane can be obtained at a high yield of 95 to 98%.
なお、この反応は必要に応じオートクレーブを使用した
加圧下で行なってもよく、このときには反応温度５０〜
１００℃、反応圧力１．１〜１０気圧という条件で行え
ばよりよい結果を得ることかてぎる。In addition, this reaction may be carried out under pressure using an autoclave if necessary, and in this case, the reaction temperature is 50 to 50℃.
Better results may be obtained if the reaction is carried out at a temperature of 100° C. and a reaction pressure of 1.1 to 10 atm.
［実施例］ つぎに本発明の実施例、比較例をあげる。[Example] Next, examples of the present invention and comparative examples will be given.
実施例１
内容積６０ｍｊ＋の弗素樹脂加工されたＳＵＳ製のオー
トクレーブに、２．３−ジメチル−２−ブテン１５．１
ｇ （０，１８モル）とトリクロロシラン３６．６ｇ（
０，２７モル）および触媒としての２，２゛−アゾビス
（イソブチロニトリル） ０．３０ｇ （０，００１８
モル）を入れ、８０℃で５気圧下に３００時間反応せ、
反応終了後に反応溶液を蒸溜したところ、テキシルトリ
クロロシラン３７．３ｇ （０，１７モル）が収率９８
％で得られた。Example 1 15.1 of 2.3-dimethyl-2-butene was placed in a fluororesin-treated SUS autoclave with an internal volume of 60 mJ+.
g (0.18 mol) and 36.6 g of trichlorosilane (
0.27 mol) and 0.30 g of 2,2'-azobis(isobutyronitrile) as catalyst (0.0018
mol) and reacted at 80°C under 5 atm for 300 hours.
After the reaction was completed, the reaction solution was distilled, and 37.3 g (0.17 mol) of thexyltrichlorosilane was obtained in a yield of 98.
Obtained in %.
なお、ここに得られたテキシルトリクロロシランは沸点
８１℃／２３ｍｍＨｇ、 ’Ｈ−ＮＭＲ（ＣＣＲ４，６
０ＭＨｚ）。The thexyltrichlorosilane obtained here has a boiling point of 81°C/23mmHg, 'H-NMR (CCR4,6
0MHz).
δ２．３〜１．７（ｍ、 ＩＨ）、 １．２５（Ｓ、
６）１）、 １．１３（ｄ、 ６Ｈ。δ2.3~1.7 (m, IH), 1.25 (S,
6)1), 1.13(d, 6H.
Ｊ−６Ｈｚ） という物性を示した。J-6Hz).
比較例１
攪拌機、還流器、滴下ロートおよび温度計を備えた２０
０ｍ＃の四ツロフラスコにトリクロロシラン３５．２ｇ
（０，２６モル）、触媒としての無水塩化アルミニウ
ム２．７ ｇ （０，，０２モル）を入れ、滴下ロート
から２．３−ジメチル−２−ブテン１６．８ｇ （０，
２０モル）を１時間で滴下し、１５〜２０℃で反応させ
、滴下終了後に温度を２０〜３０℃に保持して１時間熟
成させ、反応終了後ガスクロマトグラフィーで分析した
ところ、原料としての２．３−ジメチル−２−ブテンは
消失していたが、この場合には多数の生成物が与えられ
ているものの目的とするテキシルトリクロロシランは得
られず、テキシルトリクロロシランを得るために無水塩
化アルミニウムは適当なものでないことが確認された。Comparative Example 1 20 equipped with stirrer, reflux, dropping funnel and thermometer
35.2g of trichlorosilane in a 0m# Yotsuro flask
(0.26 mol), 2.7 g (0.02 mol) of anhydrous aluminum chloride as a catalyst, and 16.8 g (0.02 mol) of 2.3-dimethyl-2-butene from the dropping funnel.
20 mol) was added dropwise over 1 hour and reacted at 15-20°C. After the dropwise addition, the temperature was maintained at 20-30°C and aged for 1 hour. After the reaction was completed, analysis by gas chromatography revealed that it was a raw material. 2.3-dimethyl-2-butene had disappeared, but in this case, although a large number of products were given, the desired thexyltrichlorosilane could not be obtained, and in order to obtain thexyltrichlorosilane, It has been determined that anhydrous aluminum chloride is not suitable.
比較例２
内容積６０ｍＪのオートクレーブに２．３−ジメチル−
２−ブテン１０．２ｇ （０，１２モル）とトリクロロ
シラン１７．６ｇ （０，１２５モル）および触媒とし
ての塩化白金酸六水和物０．１モルイソプロピルアルコ
ール溶液０１３ｇを入れ、８０℃で５気圧下に５時間反
応させ、反応終了後反応溶液を蒸溜したところ、ＣＨ２
Ｈ
示される２、３−ジメチルブチルトリクロロシラン２０
．５ｇ （０，０９モル）が収率７７％で得られ、この
ものは沸点６３℃／ ７ ｍｍＨｇ、 ’Ｈ−ＮＭＲ（
ＣＨＣｌ）ｓ、 ６０Ｍ）ｌｚ）。Comparative Example 2 2.3-dimethyl- was placed in an autoclave with an internal volume of 60 mJ.
10.2 g (0.12 mol) of 2-butene, 17.6 g (0.125 mol) of trichlorosilane, and 013 g of a 0.1 mol isopropyl alcohol solution of chloroplatinic acid hexahydrate as a catalyst were added, and the mixture was heated at 80°C for 50 minutes. The reaction was carried out under atmospheric pressure for 5 hours, and when the reaction solution was distilled after the reaction, CH2
H 2,3-dimethylbutyltrichlorosilane 20 as shown
．． 5 g (0.09 mol) was obtained with a yield of 77%, which had a boiling point of 63 °C / 7 mmHg, 'H-NMR (
CHCl)s, 60M)lz).
δ２．１〜１．６（ｍ、 ２Ｈ）、 １．５〜１．３（
ｍ、 ２Ｈ）、 １．２〜０．８（ｍ、 ９Ｈ）という
物性を示したが、この場合にはテキシルトリクロロシラ
ンは得られなかった。δ2.1~1.6(m, 2H), 1.5~1.3(
m, 2H) and 1.2 to 0.8 (m, 9H), but thexyltrichlorosilane was not obtained in this case.
実施例２
実施例１における触媒としての２，２°−アゾビス（イ
ソブチロニトリル）の代わりに、つぎの第１表に示した
アゾ化合物を用いたほかは実施例１と同じ方法で反応さ
せたところ、第１表に記載した収率でテキシルトリクロ
ロシランを得ることができた。Example 2 A reaction was carried out in the same manner as in Example 1, except that the azo compounds shown in Table 1 below were used instead of 2,2°-azobis(isobutyronitrile) as a catalyst in Example 1. As a result, thexyltrichlorosilane could be obtained in the yield shown in Table 1.
′ｆＳ１表
ルキルシアノ基から選択される基）で示される触媒とし
てのアゾ化合物の存在下で反応させることを特徴とする
ものであるが、これによればこの反応が比較的温和な条
件下で容易に進行し、目的とするテキシルトリクロロシ
ランを殆んど定量的に９５〜９８％といつ高収率で得る
ことができるという工業的な有利性が与えられる。This method is characterized by carrying out the reaction in the presence of an azo compound as a catalyst represented by 'fS1 (a group selected from alkylcyano group), which allows this reaction to be carried out easily under relatively mild conditions. It is industrially advantageous that the desired thexyltrichlorosilane can be obtained almost quantitatively in a high yield of 95 to 98%.
［発明の効果コ
本発明はテキシルトリクロロシランの製造方法に関する
もので、これは前記したようにトリクロロシランと２．
３−ジメチル−２−ブテンとを式Ｒ−Ｎ＝Ｎ−Ｒ（ここ
にＲはアルキル基、アルキルシアノ基、アルキルエーテ
ルシアノ基、環状ア特許出願人 信越化学工業株式会社[Effects of the Invention] The present invention relates to a method for producing thexyltrichlorosilane, which, as described above, comprises trichlorosilane and 2.
3-dimethyl-2-butene and the formula R-N=N-R (where R is an alkyl group, an alkyl cyano group, an alkyl ether cyano group, a cyclic apatent applicant Shin-Etsu Chemical Co., Ltd.
Claims (1)
とを式Ｒ−Ｎ＝Ｎ−ＲここにＲはアルキル基、アルキル
シアノ基、アルキルエーテルシアノ基、環状アルキルシ
アノ基から選択される基）で示される触媒としてのアゾ
化合物の存在下に反応させることを特徴とするテキシル
トリクロロシランの製造方法。1. Trichlorosilane and 2,3-dimethyl-2-butene are expressed by the formula R-N=NR-R, where R is a group selected from an alkyl group, an alkyl cyano group, an alkyl ether cyano group, and a cyclic alkyl cyano group) 1. A method for producing thexyltrichlorosilane, which is characterized by carrying out the reaction in the presence of an azo compound as a catalyst represented by:
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2172449A JP2517783B2 (en) | 1990-06-29 | 1990-06-29 | Method for producing thexyltrichlorosilane |
| CH185691A CH681725A5 (en) | 1990-06-29 | 1991-06-24 | Tri:chloro-silane deriv. prodn. for prepn. of silicone resins, etc. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2172449A JP2517783B2 (en) | 1990-06-29 | 1990-06-29 | Method for producing thexyltrichlorosilane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0466588A true JPH0466588A (en) | 1992-03-02 |
| JP2517783B2 JP2517783B2 (en) | 1996-07-24 |
Family
ID=15942194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2172449A Expired - Fee Related JP2517783B2 (en) | 1990-06-29 | 1990-06-29 | Method for producing thexyltrichlorosilane |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP2517783B2 (en) |
| CH (1) | CH681725A5 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69520332T2 (en) * | 1994-11-25 | 2001-08-09 | Japan Polyolefins Co. Ltd., Tokio/Tokyo | Catalyst for polymerizing olefins and process for producing polyolefins using the same |
| US5527936A (en) * | 1995-02-17 | 1996-06-18 | E. I. Du Pont De Nemours And Company | Hydrosilylation of unsaturated compounds |
| US5530152A (en) * | 1995-02-17 | 1996-06-25 | E. I. Du Pont De Nemours And Company | Method for manufacturing organosilanes |
-
1990
- 1990-06-29 JP JP2172449A patent/JP2517783B2/en not_active Expired - Fee Related
-
1991
- 1991-06-24 CH CH185691A patent/CH681725A5/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH681725A5 (en) | 1993-05-14 |
| JP2517783B2 (en) | 1996-07-24 |
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