JPH01168645A - Production of 4-chloro-2-fluoronitrobenzene - Google Patents
Production of 4-chloro-2-fluoronitrobenzeneInfo
- Publication number
- JPH01168645A JPH01168645A JP62325514A JP32551487A JPH01168645A JP H01168645 A JPH01168645 A JP H01168645A JP 62325514 A JP62325514 A JP 62325514A JP 32551487 A JP32551487 A JP 32551487A JP H01168645 A JPH01168645 A JP H01168645A
- Authority
- JP
- Japan
- Prior art keywords
- dichloronitrobenzene
- chloro
- fluoronitrobenzene
- reaction
- crown
- 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.)
- Granted
Links
- PTCPUGKKWNMITF-UHFFFAOYSA-N 4-chloro-2-fluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1F PTCPUGKKWNMITF-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 claims abstract description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 150000003983 crown ethers Chemical class 0.000 claims abstract description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 abstract description 6
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 5
- 239000012454 non-polar solvent Substances 0.000 abstract description 5
- 239000008096 xylene Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 12
- 239000011698 potassium fluoride Substances 0.000 description 7
- 235000003270 potassium fluoride Nutrition 0.000 description 6
- VZHJIJZEOCBKRA-UHFFFAOYSA-N 1-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1 VZHJIJZEOCBKRA-UHFFFAOYSA-N 0.000 description 3
- RJXOVESYJFXCGI-UHFFFAOYSA-N 2,4-difluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1F RJXOVESYJFXCGI-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
- KQOOFMWRLDRDAX-UHFFFAOYSA-N 2-chloro-4-fluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1Cl KQOOFMWRLDRDAX-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- -1 crown-6 Chemical class 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野） る。[Detailed description of the invention] [Industrial application field] Ru.
２．４−ジクロルニトロベンゼン（１） とフッ化アル
カリとの反応によるフルオロニトロベンゼン類の製造法
に関しては、既にい（つかの報告がある。There have already been some reports regarding a method for producing fluoronitrobenzenes by reacting 2.4-dichloronitrobenzene (1) with an alkali fluoride.
しかしながら、この反応により得られるフルオロニトロ
ベンゼン類としては４−クロル−２−フルオロ〉トレ
二トロベンゼンＣＵ）、２−クロル−４−フルオ官（ン
ゼン（Ｉｆｆ）、２．４−ジフルオロニトロベンゼン（
■）があげられ、これら化合物のうち、４−クロル−２
−フルオロニトロベンゼン（Ｉｆ） ヲ高選択的に得る
方法に関する報告はない。However, the fluoronitrobenzenes obtained by this reaction include 4-chloro-2-fluorotrenitrobenzene (CU), 2-chloro-4-fluorobenzene (Iff), and 2,4-difluoronitrobenzene (Iff).
■) Among these compounds, 4-chloro-2
-Fluoronitrobenzene (If) There is no report on a method for highly selectively obtaining fluoronitrobenzene (If).
例えば、Ｃｈｅｓ＋１ｓｔｒｙ ａｎｄ Ｉｎｄｕｓｔ
ｒｙ １９２Ｂ（１９６２）では２．４−ジクロルニト
ロベンゼン（Ｉ）をジメチルスルホン中、フッ化カリウ
ムと反応させること事
により、４−クロル−２−フルオロベンゼン（Ｉｔ）及
び２．４−ジフルオロニトロベンゼン（ｍＶ）を得てい
るが、収率及び転化率の記載はない。For example, Ches+1try and Industry
ry 192B (1962), 4-chloro-2-fluorobenzene (It) and 2,4-difluoronitrobenzene (I) were prepared by reacting 2,4-dichloronitrobenzene (I) with potassium fluoride in dimethylsulfone. mV), but the yield and conversion rate are not described.
Ｂｒ１ｔ、 Ｐａｔｅｎｔ １５１４０８２では、２．
４−ジクロルニトロベンゼン（１）をスルホラン中、フ
ッ化カリウムと反応させることにより、４−クロル−２
−フルオロニトロベンゼン（ｎ）、２−クロル−４−フ
ルオロニトロベンゼン（ＤＩ）及び２．４−ジフルオロ
ニトロ■）である。Brlt, Patent 1514082, 2.
By reacting 4-dichloronitrobenzene (1) with potassium fluoride in sulfolane, 4-chloro-2
-fluoronitrobenzene (n), 2-chloro-4-fluoronitrobenzene (DI), and 2,4-difluoronitrobenzene (2).
本発明の目的は、２．４−ジクロルニトロベンゼン（１
）から高選択的に４−クロル−２−フルオロニトロベン
ゼン（ＩＩ）を製造する方法を提供することである。The object of the present invention is to obtain 2,4-dichloronitrobenzene (1
) to provide a method for highly selectively producing 4-chloro-2-fluoronitrobenzene (II).
本発明ハ、２．４−ジクロルニトロベンゼン（１）にフ
ッ化アルカリを反応させて４−クロル−２−フルオロニ
トロベンゼン（ＩＩ）を製造するに際し、非極性溶媒中
、クラウンエーテル又は四級アンモニウム塩の触媒の存
在下で反応させることを特徴とする４−クロル−２−フ
ルオロニトロベンゼン（ＩＩ）の製造法である。In the present invention, when producing 4-chloro-2-fluoronitrobenzene (II) by reacting 2,4-dichloronitrobenzene (1) with an alkali fluoride, a crown ether or a quaternary ammonium salt is prepared in a non-polar solvent. This is a method for producing 4-chloro-2-fluoronitrobenzene (II), characterized in that the reaction is carried out in the presence of a catalyst.
本発明で用いられる非極性溶媒として好ましいものは、
ベンゼン、トルエン、キシレン、メシチレン等の芳香族
炭化水素系、ジエチレングリコールジエチルエーテル、
エチレングリコールジエチルエーテル等のエーテル系で
ある。Preferred nonpolar solvents used in the present invention are:
Aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, diethylene glycol diethyl ether,
It is an ether type such as ethylene glycol diethyl ether.
本発明で用いられる触媒は、１Ｂ−クラウン−６、ジベ
ンゾ−１８−クラウン−６、ジシクロへキシル−１８−
クラウン−６等のクラウンエーテル、トリオクチルメチ
ルアンモニウムクロライド、トリエチルベンジルアンモ
ニウムクロライド、トリメチルフェニルアンモニウムク
ロライド、Ｎ−（２−エチルヘキシル） −４−（ジメ
チル）アミノピリジウムクロライド等の四級アンモニウ
ム塩であり、使用量は（１）に対し１モル％〜１０モル
％である。The catalysts used in the present invention include 1B-crown-6, dibenzo-18-crown-6, dicyclohexyl-18-
A crown ether such as crown-6, a quaternary ammonium salt such as trioctylmethylammonium chloride, triethylbenzylammonium chloride, trimethylphenylammonium chloride, N-(2-ethylhexyl)-4-(dimethyl)aminopyridium chloride, The amount used is 1 mol % to 10 mol % based on (1).
フッ化カリウムが用いられ、その使用量は（１）に対し
当モル以上、好ましくは１．２〜２．６倍モルである。Potassium fluoride is used, and the amount used is at least the equivalent molar amount of (1), preferably 1.2 to 2.6 times the molar amount.
反応温度は８０〜１９０℃好ましくは１１０℃から用い
る溶媒の沸点である。The reaction temperature is 80 to 190°C, preferably 110°C to the boiling point of the solvent used.
反応温度は８０〜１９０℃好ましくは１１０℃から用い
る溶媒の沸点である。The reaction temperature is 80 to 190°C, preferably 110°C to the boiling point of the solvent used.
次に実施例を挙げ本発明を更に詳細に説明する。 Next, the present invention will be explained in more detail with reference to Examples.
実施例１
５０ 丸底フラスコに攪拌子を入れ２．４−ジクロル
ニトロベンゼン４．８ｇ（０，０２５モル）、フッ化カ
リウム３．８ｇ（０，０６５モル）、１８−クラウン−
６０，７ＦＣ０，００２５モル）を混合し、メシチレン
２０ｍ１で希釈した後１６４℃まで加温して反応を行な
った。Example 1 50 Put a stir bar into a round bottom flask and add 4.8 g (0,025 mol) of 2,4-dichloronitrobenzene, 3.8 g (0,065 mol) of potassium fluoride, and 18-crown-
60.7FC (0,0025 mol) was mixed, diluted with 20 ml of mesitylene, and then heated to 164°C to carry out a reaction.
反応生成物の分析はガスクロマトグラフィーにより（Ｇ
Ｃ分析と略記する場合あり、）行なった。結実施例２
実施例１０ＫＦ量を１．８ｇに変え、その他は実施例１
と同様に反応した結果は表−２に示す。The reaction products were analyzed by gas chromatography (G
(Sometimes abbreviated as C analysis) was carried out. Conclusion Example 2 Example 10 The amount of KF was changed to 1.8 g, and the rest was Example 1.
The results of the same reaction are shown in Table 2.
実施例３
実施例１のメシチレン量を４０ｍ ｌに変え、その他は
実施例１と同様に反応した。結果は表−２に示す。Example 3 The reaction was carried out in the same manner as in Example 1 except that the amount of mesitylene in Example 1 was changed to 40 ml. The results are shown in Table-2.
実施例４
実施例１のメシチレンをトルエンに又反応温度を１１０
℃に変え、その他は実施例１と同様に反応した。結果
は表−２に示す。Example 4 The mesitylene of Example 1 was changed to toluene and the reaction temperature was changed to 110℃.
The reaction temperature was changed to 0.degree. C., and the reaction was otherwise carried out in the same manner as in Example 1. The results are shown in Table-2.
実施例５
実施例１のメシチレンをキシレンに反応温度を１４０℃
に変え、その他は実施例１と同様に反応した。結果は表
−２に示す。Example 5 Mesitylene of Example 1 was converted into xylene at a reaction temperature of 140°C.
The reaction was carried out in the same manner as in Example 1 except that the reaction was performed in the same manner as in Example 1. The results are shown in Table-2.
実施例６
実施例４の１８−クラウン−６０，７ｇをトリオクチル
メチルアンモニウムクロライド０．９ｇに変えその他は
実施例４と同様に反応した。結果は表−２に示す。Example 6 The reaction was carried out in the same manner as in Example 4 except that 60.7 g of 18-crown in Example 4 was replaced with 0.9 g of trioctylmethylammonium chloride. The results are shown in Table-2.
実施例７
５００ 丸底フラスコに攪拌子を入れジムロートコン
デンサー、塩化カルシウム管を付け２，４−ジクロルニ
トロベンゼン４８．０ｇ フッ化カリウム３６．０ｇ１
８−クラウン−６７，０ｇを混合しキシレン２００ａｒ
で希釈した。この混合物を油浴で加熱還流させた。１９
時間後室温まで冷却し、水洗、１０％にＣＺ水洗、硫酸
マグネシウム乾燥後、キシレンを減圧濃縮して残渣をウ
ィツトマー精留管を用いて減圧蒸留を行なった。結果は
表−３に示す。Example 7 500 Put a stirrer in a round bottom flask, attach a Dimroth condenser and a calcium chloride tube, 48.0 g of 2,4-dichloronitrobenzene, 36.0 g of potassium fluoride.
8-crown-67.0g mixed with xylene 200ar
diluted with This mixture was heated to reflux in an oil bath. 19
After an hour, the mixture was cooled to room temperature, washed with water, washed with 10% CZ water, dried with magnesium sulfate, concentrated under reduced pressure to remove xylene, and the residue was distilled under reduced pressure using a Wittmer rectifying tube. The results are shown in Table-3.
表−３
２トｖ
反応率は２８．１％、４−クロル−２−フルオーくンゼ
ンの収率２４．２％、選択率８６．１％であった。Table 3: The reaction rate was 28.1%, the yield of 4-chloro-2-fluoroquinzene was 24.2%, and the selectivity was 86.1%.
実施例８
実施例７の還流時間を６８時間に変えその他は実施例７
と同様に反応後処理を行なった。蒸留結果を表−４に示
す。Example 8 Example 7 except that the reflux time in Example 7 was changed to 68 hours.
Post-reaction treatment was carried out in the same manner as above. The distillation results are shown in Table 4.
表−４ ンの収率５９．１％、選択率は７１．４％であった。Table-4 The yield was 59.1%, and the selectivity was 71.4%.
比較例
２．４−ジクロルニトロベンゼン４．８ｇ、フッ化カリ
ウム２．０ｇ、をスルホラン１．７ｇに溶解して２４０
℃で１５時間反応を行った。Comparative Example 2. 4.8 g of 4-dichloronitrobenzene and 2.0 g of potassium fluoride were dissolved in 1.7 g of sulfolane.
The reaction was carried out at ℃ for 15 hours.
反応生成物の分析はガスクロマトグラフィーにより行っ
た。Analysis of the reaction products was performed by gas chromatography.
結果を表−５に示す。The results are shown in Table-5.
表−５
（■）カラ４−クロル−２−フルオロニトロベンゼン（
ＩＩ）が高選択的かつ高収率で得られる。Table 5 (■) Kara-4-chloro-2-fluoronitrobenzene (
II) is obtained with high selectivity and high yield.
出 願 人 日本曹達株式会社Applicant: Nippon Soda Co., Ltd.
Claims (1)
化アルカリを反応させて４−クロル−２−フルオロニト
ロベンゼン（II）を製造するに際し、非極性溶媒中、ク
ラウンエーテル又は四級アンモニウム塩の触媒の存在下
で反応させることを特徴とする４−クロル−２−フルオ
ロニトロベンゼン（II）の製造法。(1) When producing 4-chloro-2-fluoronitrobenzene (II) by reacting 2,4-dichloronitrobenzene (I) with an alkali fluoride, crown ether or quaternary ammonium salt is A method for producing 4-chloro-2-fluoronitrobenzene (II), characterized by carrying out the reaction in the presence of a catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62325514A JP2520276B2 (en) | 1987-12-24 | 1987-12-24 | Process for producing 4-chloro-2-fluoronitrobenzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62325514A JP2520276B2 (en) | 1987-12-24 | 1987-12-24 | Process for producing 4-chloro-2-fluoronitrobenzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01168645A true JPH01168645A (en) | 1989-07-04 |
| JP2520276B2 JP2520276B2 (en) | 1996-07-31 |
Family
ID=18177728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62325514A Expired - Lifetime JP2520276B2 (en) | 1987-12-24 | 1987-12-24 | Process for producing 4-chloro-2-fluoronitrobenzene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2520276B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5463148A (en) * | 1991-07-17 | 1995-10-31 | Hoechst Aktiengesellschaft | Process for the preparation of chlorofluoronitrobenzenes |
| WO2005113547A1 (en) * | 2004-05-24 | 2005-12-01 | Wako Pure Chemical Industries, Ltd. | Ionic-liquid-supporting crown compound |
-
1987
- 1987-12-24 JP JP62325514A patent/JP2520276B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5463148A (en) * | 1991-07-17 | 1995-10-31 | Hoechst Aktiengesellschaft | Process for the preparation of chlorofluoronitrobenzenes |
| WO2005113547A1 (en) * | 2004-05-24 | 2005-12-01 | Wako Pure Chemical Industries, Ltd. | Ionic-liquid-supporting crown compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2520276B2 (en) | 1996-07-31 |
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