TW201749B - - Google Patents
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- TW201749B TW201749B TW081102981A TW81102981A TW201749B TW 201749 B TW201749 B TW 201749B TW 081102981 A TW081102981 A TW 081102981A TW 81102981 A TW81102981 A TW 81102981A TW 201749 B TW201749 B TW 201749B
- Authority
- TW
- Taiwan
- Prior art keywords
- temperature range
- reaction
- item
- applying
- thiourea
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 15
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 Butyl acyl ester Chemical class 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NAHLQCFWWVZWDY-UHFFFAOYSA-N 1,4-dioxane;ethane-1,2-diol Chemical compound OCCO.C1COCCO1 NAHLQCFWWVZWDY-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- XFKQXANXMAWSKE-UHFFFAOYSA-N [S].NC(N)=S Chemical compound [S].NC(N)=S XFKQXANXMAWSKE-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 1
- QHNXEVRKFKHMRL-UHFFFAOYSA-N dimethylazanium;acetate Chemical compound CNC.CC(O)=O QHNXEVRKFKHMRL-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N ethylene glycol dimethyl ether Natural products COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 239000008433 xiaoji Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/06—Peri-condensed systems
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/121—Charge-transfer complexes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Paper (AREA)
Description
0J 81.9.2 2 _势彷49 ’ ’ /νυ —，........... .it G _ 五、發明説明（L) 本發明是關經5,6. 11, 12 -四氛四¥和硫脲及硫之混合 物在極性非質子性溶劑中進行反應以産出5 . 6 , 1 1 , 1 2 -四 碕四¥之方法。 在 Latv. P S R Z i n a t . A k a d . Vestis, K h i m. S e r., P.633(1989), R.Medne et al.曾提及在惰性大氣中5,6 ,U.〗2 -四氛四¥和硫脲在六甲磷三醛胺中之反應。此 反應所得之5,6, 11 ,12 -四硫四¥産率為中等且其純度欠 佳。 · 迄今經發現藉由添加及同向流動之硫於此反應可實質上 提高産物之産率和純度，即使是不在惰氣環境中亦為如此。 故此，本發明是有關於一種製備式I之5,6, 11, 12 -四
硫四¥之方法，其中 S-S
S-S (I) 經濟部屮央標準;0cx工消价合作社印製
將式Π之5,6. 11, 12 -四氣四¥ Cl CI
(II)
… .Cl CI 與硫豚在極性非筲子性溶劑中反應&此製程亦包括與硫 脲_硫之混合物反應，、 -3 - 81. 4. 10,000^(11) (請先間請背而之注意事項种塡寫木頁) 本紙5fc尺度边用中Η國家«liMCNS) T4規格(210X297公龙） £01749 Λ 6 η 6 經濟部十央榀準/(·;Α工消作合作杜印Μ 五、發明説明（ζ ) 合適的溶劑包括Ν -烷化酸醯胺和内醛胺（典型的為二 甲基甲醯胺，二乙基甲醯胺，二甲基乙醯胺，四甲基解 ,六甲礤三醯胺，Ν -甲基吡咯啶酮），醚類（包含二丙 醚，二丁醚，四氫呋喃，二噁烷乙烯二醇二甲基或二乙 醚），酷類或内酯類，（典型的為乙基，丙基.丁基酷 酯，乙基丙醯酯，乙基丁醯酯，丁内酯，戊内酯），6風 類和亞δ風類（典型二甲亞硯，二甲5思，四乙烯δ；| )，.較 佳溶劑為H -烷化羧醯胺或内醛胺，最佳為二甲基乙醯胺 〇 . 反噻溫度之範圍可在7 0至2 5 0 t：,較佳為由8 0至2 0 0 t 及較佳為80至16〇υ。在本發明的一個較佳的實體中， 反暱是開始時進行2 0小時，較佳為至1 0小時.而溫度的 範圍為70至120C.較佳為80至110Τ：,然後接着的6小 時.較佳為4小時.溫度範圍為1201至25〇υ,較佳為 1301 至 2001,最佳為 至 16〇1〇。 硫脲與硫之用量.基於5,6, 11, 12 -四氯四¥之量，可 為同當最。較佳為使用過量之硫胛，，在此新穎性的製程 的一舾較佳的《體中，採用4.2至42Μ耳當量，較佳為 10至15其耳當《的硫脲和2. 5至10其耳當量.較佳為4至 6契耳笟费之硫，皆偽基於1 Μ耳的5,6, U. 12 -四氯四 ¥ 5.6, 11. 12 -四氛四¥在反應混合物中的濃度為毎升溶 劑由0.01至0.20埏耳.較佳為0.06至0.12契耳。 -4- (4先閲-;*?背而之注意事項#填窵木頁) 裝. 訂· 線. 本紙張尺度边用中《»家樣準（CNS)T4規格（210x297公放） 81. 4. 10,000張⑻ \\6 \\6 經濟部屮央標準灼只工消奸合作社印奴 五、發明説明（3 ) 此反應可在提升之溫度中進行，但常壓下是有利的。 在惰性大氣進行此反應亦為可能。此新穎性製程的一特 為惰性大氣並非必要，而反應可在大氣中進行。 此新穎性製程可有效的將硫加入溶劑中並加熱此混合 物。随後將硫解和5,6, 11, 12 -四氛四¥加入此熱溶液中 ,將其在所指的溫度中攪拌一段時間。随後將溫度提高 並繼禳搜拌一段時間。 用已知的方法將5,6, 11, 12 -四氛四¥隔離，而典型之 方法為將此反應混合物與稀礦酸進行水解.然後將其沉 殿物锊過濾以捎得。 5,6. 11, 12 -四硫四¥是已知的電子予體，其可與電子 受體结合.其中電子受體之例子囱素，導電自由陽離子 鹽（有機化金屬物）可用來做為抗解霣處理之塑膠或做為 霄極。 本發明可由以下之實施例說明。 K施例： 將6克之硫和 225¾升的二甲基乙酸胺在開口的容 器中加熱至90t：,、随後加入30克的碕脲並攪拌此溶液。 抟转添加13.5克的5,6, 11. 12 -四氮四¥。此反應混合物 開始時在90t中先攛拌6小時.然後在140t：中HS拌2 小時將此黑绵溶液冷卻至丨丨0 Ό並以含4 . 5牵升之5 N H C丨的】1 2 5奄升的水，以點滴方式在1 0分鐽内加入^在 4 0 將沉澱以過濾法隔離並以1升之水.1升之乙醇， -5- 〈請先•閲1.?背而之注意事項孙蜞寫本頁) 裝. 訂 本紙張尺度逍用中《 ffl家«準（CNS)〒4規彷（210X297公Λ) 81_ 4‘ 〗0,000張（||)
Λ (5 l\C 五、發明説明（4 ) 1升之苯和200毫升的二乙醚洗餻。在室溫及真空中將 此産物烘乾，可得11.3克（理論值為855；)的5,6, 11,12-四硫四¥ .其純度超過98% 。 (^先^誚背而之注意事項洱填寫木頁) 經濟部屮央榀準而只工消价合作社印魟 8L 4. )0,000¾ (JI) 本紙張尺度边用中《«家«毕（CNS)T4規格（210x297公釐）
Claims (1)
- S-S將式Π之5， 6, 11，12 -四氰四 A7 B7 Cl D7 六、申請專利範園 第81102981號「製儎5, 6, 11, 12 -四硫四分之方法」 (8 2年1月修正） 1. 一種製備式I之5， 6，11，12 -四硫四#之方法，其 中 (I) (請先閲讀背面之注意事項再填寫本頁) 裝. Cl CI(II) 訂. 線. 經濟部中央襟準局S工消费合作社印製 與硫脲在極性非質子性溶_中反應且此製程亦包括與硫 脲與硫之混合物反應，其中溶劑為Ν-烷化之竣胺或為内 醛胺，反應溫度之範園為70至250t，包含採用10至15 莫耳當量之硫脲和每奠耳5, 6，11，12 _四«四f之 4至6莫耳當量之硫且5, 6, 11, 12 -四氛四斧在反 應混合物中之獷度是由毎升溶_ — 0.01至0·20奠耳。 -1 - 私紙張尺度適用中國國家標準（CNS)甲4规格（210 X 297公釐） A7 • B7 C7 D7 六、申請專利範園 2. 如申謫專利範園第1項之方法，其中溶劑為二甲基乙酸 醛胺。 3. 如申謫專利範_第1項之方法，其中反窿溫度之範圍為 80 至 20 01： 〇 4如申_專利範匾第1項之方法，其中反應開始20小時之 溫度範園為70至128t：.随後之6小時之溫度範圆為 120 至 250 T： 〇 5. 如申謓專利範圍第4項之方法，其中反醮颶始2〇小時之 溫度範圔為80至110t：,随後之6小時之溫度範圍為 130 至 2001C 〇 6. 如申請專利範团第1項之方法，其中反應偽在非惰氣環 * 境中進行。 4-----裝------訂 τ---i—-線 (請先閲讀背面之注意事項再塡寫本頁) 經濟部中央揉準局Λ工消费合作社印製 -2- 本紙張尺度適用中蹰家螵準（CNS) Τ 4规格（210 X 297公釐）
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH123691 | 1991-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201749B true TW201749B (zh) | 1993-03-11 |
Family
ID=4205662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW081102981A TW201749B (zh) | 1991-04-25 | 1992-04-16 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5206388A (zh) |
| EP (1) | EP0511164B1 (zh) |
| JP (1) | JPH05202058A (zh) |
| KR (1) | KR920019795A (zh) |
| CA (1) | CA2066939A1 (zh) |
| DE (1) | DE59206210D1 (zh) |
| TW (1) | TW201749B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2076732T3 (es) * | 1991-07-02 | 1995-11-01 | Ciba Geigy Ag | Sales de tetratiotetraceno de cation radical y cloruro de cobre su preparacion y uso. |
| US7989695B2 (en) * | 2001-12-18 | 2011-08-02 | Steven Allen Carlson | Organic photovoltaic cells |
| JP5652856B2 (ja) * | 2010-06-15 | 2015-01-14 | 国立大学法人 岡山大学 | ヘキサチアペンタセン化合物及びその製造方法、並びにそれからなる光触媒 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636048A (en) * | 1970-07-15 | 1972-01-18 | American Cyanamid Co | Chloronaphtho dithiole compounds and a method for their preparatio |
| DE3870012D1 (de) * | 1987-04-03 | 1992-05-21 | Ciba Geigy Ag | Antistatische und elektrisch leitende polymere und formmassen. |
| EP0344111A3 (de) * | 1988-05-27 | 1990-04-04 | Ciba-Geigy Ag | Substituierte Tetrathio- und Tetraselenotetracene |
-
1992
- 1992-04-13 JP JP4118537A patent/JPH05202058A/ja active Pending
- 1992-04-16 EP EP92810284A patent/EP0511164B1/de not_active Expired - Lifetime
- 1992-04-16 TW TW081102981A patent/TW201749B/zh active
- 1992-04-16 DE DE59206210T patent/DE59206210D1/de not_active Expired - Fee Related
- 1992-04-22 US US07/872,735 patent/US5206388A/en not_active Expired - Fee Related
- 1992-04-23 KR KR1019920006845A patent/KR920019795A/ko not_active Withdrawn
- 1992-04-23 CA CA002066939A patent/CA2066939A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0511164B1 (de) | 1996-05-08 |
| CA2066939A1 (en) | 1992-10-26 |
| DE59206210D1 (de) | 1996-06-13 |
| EP0511164A1 (de) | 1992-10-28 |
| US5206388A (en) | 1993-04-27 |
| JPH05202058A (ja) | 1993-08-10 |
| KR920019795A (ko) | 1992-11-20 |
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