TWI290916B - Phosphoric acid salt of an aromatic diamin - Google Patents
Phosphoric acid salt of an aromatic diamin Download PDFInfo
- Publication number
- TWI290916B TWI290916B TW089106728A TW89106728A TWI290916B TW I290916 B TWI290916 B TW I290916B TW 089106728 A TW089106728 A TW 089106728A TW 89106728 A TW89106728 A TW 89106728A TW I290916 B TWI290916 B TW I290916B
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- phenylenediamine
- phosphoric acid
- patent application
- phosphate
- Prior art date
Links
- 125000006157 aromatic diamine group Chemical group 0.000 title 1
- 150000003016 phosphoric acids Chemical class 0.000 title 1
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 claims abstract description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- OOZKQOFEBPDHPA-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine;phosphoric acid Chemical compound OP(O)(O)=O.CNC1=CC=CC=C1N OOZKQOFEBPDHPA-UHFFFAOYSA-N 0.000 claims description 3
- -1 phosphonium-methyl-o-phenylenediamine phosphate Chemical compound 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 7
- 235000011007 phosphoric acid Nutrition 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 102000011759 adducin Human genes 0.000 description 1
- 108010076723 adducin Proteins 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/51—Phenylenediamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Detergent Compositions (AREA)
- Packaging Frangible Articles (AREA)
- Packages (AREA)
Description
1290916 A7 ----~-~2Z___ 五、發明說明（3 ) 並播其他此種鹽類於先前技藝中所提之缺點及導致的問 題，，或使此等缺點及問題減低至明顯的程度。 A本發明經由轉變^^_甲基_鄰_苯二胺成下列通式（1)之磷 酸鹽而解決了該問題·· nh2 * η Η3Ρ〇4 ch3 ⑴ 其中η爲介於〇·5至1的數字。 磷酸鹽”一詞表示Ν _甲基-鄰一苯二胺與正磷酸（Η3ρ〇4) 之所有鹽。根據化學式I，1分子的H3pq4對1分子的ν -甲 基-鄰·苯二胺之比例以統計上之平均値η表示。 上述之鹽中，η以0 · 7至〇 . 8爲較佳··以等於0.75至〇.78爲# 最佳。 在一特佳的實施例中，本發明之Ν-甲基-鄰·苯二胺之磷 酸鹽爲無水的或只含有非常少量的水。該鹽的含水量一般 介於1.0%至1.5重量％之間。 根據本發明之Ν -甲基-鄰-苯二胺之磷酸鹽的優點在於其 氧化抗性、光不敏感性及不吸濕的特性。因此易於辟存而 不需任何大筆的花費，以及視情況有時需將其轉換成游離 驗外，可於無額外處置下用於接續反應。另外，可驚人地 容易的方式被大量製造，因磷酸可以晶體的方式加入。再 者，當該磷酸鹽本身在高溫下被進一步使用時，在該反靡 條件下’不會生成具侵蚀性及高腐蚀的氣體。 -6- 本紙張尺度適用中關家標準（CNS)A4規格（210 X 297公" ---- ------------裝--------訂—------^9. (請先閱讀背面之注咅？事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製
1290916 五、發明說明（4 ) 再一万面，本發明係關於上述N-甲基-鄰.苯二胺磷酸 鹽之工業規模製造。 該鹽易藉下法以高產量獲得：將…甲基_鄭_苯二胺溶於 水可互落性或醇可互溶性溶劑（諸如的醇類，較佳者 爲乙醇、丙醇或異丙醇）中。錢將此混合物與鱗酸結晶 或磷酸溶液（75至1()()莫耳百分比的量）反應。磷酸可溶於 或懸浮於水、Cl_C5醇類（如甲醇、乙醇、丙醇、異丙醇） 或其混合物中^較佳以乙醇、丙醇或異丙醇做爲溶劑。 N-甲基-鄰-苯二胺_磷酸鹽可從溶劑中析出，或視情況 經由加入非極性溶劑如脂肪族或芳香族烴或醚使其析出。 在較佳製程中，使用無水磷酸。 本發明的另一實施例係關於經由鄰-硝基_ N -甲苯胺之還 原原地製備N -甲基-鄰-苯二胺之製程。 鄰-硝基_N_甲苯胺之還原可用先前技藝已知的方法進 行。較佳的還原劑爲氫，並使用在做爲溶劑之醇類（以乙 醇、丙醇或異丙醇爲較佳）中之氫化催化劑。當移除此催 化劑之後，將所得的溶液與磷酸或磷酸溶液反應。進行氯 化時較佳使用結晶性無水磷酸懸浮於醇之懸浮液。 實例1 將1 90公斤的鄰-硝基-N -甲苯胺、0.95公斤的鈀/焦炭催 化劑（10%的鈀）及5 70公升的異丙醇之混合物在12〇〇公升_ VA-氫化器中氫化直到氫的吸收已停止，氫化條件爲在氯 氣壓2至6巴爾、溫度60 C ’取南爲85 °C。將99公斤的石采 酸晶體與2 3 8公升的乙醇置於另一 1200公升的裝置中，嚷 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 裝--------訂--------- (請先閱讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 1290916 A7
五、發明說明（5 ) 氫化裝置中的内容物於攪拌下流入裝置中，同時遽除催化 劑。 (請先閱讀背面之注意事項再填寫本頁) 在過濾與所過濾的催化劑中，加入9 5公升的乙醇，冷卻 至1 0至2 0 °C之後並攪拌3 0至6 0分鐘。離心該產物、以 238公升的乙醇清洗並在4〇至60 Ό下眞空乾燥。 產量：230公斤的N-甲基苯二胺、0.77公斤的碍酸鹽 (9 2 %的理論回收率）。 該產物典型上含有1.0至1.5%的水。 根據滴定的結果，計算出内容物爲61 ·〇〇/〇的n -甲基苯二 胺及37.7%的嶙酸。 元素分析··碳：42.00%氫：6.34%氮：14.00%嶙·· 11.92% 實例2 經濟部智慧財產局員工消費合作社印製 將1 9 0公斤的鄰-硝基-N -甲苯胺、〇·95公斤的鈀/焦炭催 化劑（10%的鈀）及5 7 0公升的異丙醇之混合物在1200公升_ VA-氫化作用器中還原直到氫的吸收已停止，氫化條件爲 在氫氣壓2至6巴爾、溫度60 °C，最高爲85 °C。將99公斤 的磷酸晶體與238公升的異丙醇置於另一 1200公升的裝置 中，讓氫化裝置中的内容物於攪摔下流入裝置中，同時濾 除催化劑。 在過濾與所過濾的催化劑中，加入9 5公升的異丙醇，冷 卻至1 0至2 0 C之後並擅;摔3 0至6 0分鐘。離心該產物、以 238公升的異丙醇清洗並在40至60°C下眞空乾燥。 產量：225公斤的N -甲基苯二胺、〇.77公斤的磷酸鹽 -8 - 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 1290916 A7 _B7_ 五、發明說明（6 ) (9 0 %的理論回收率）。 根據滴定的結果，計算出内容物爲61.1 %的N -甲基苯二 胺及37.6的磷酸。 元素分析：碳：41.98% 氫：6.35% 氮：14.04%磷： 11.93% (請先閱讀背面之注意事項再填寫本頁) ▼裝---- 訂--- Φ 經濟部智慧財產局員工消費合作社印製 9 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐）
Claims (1)
- 焱728號專利申請案 中文申清專利籙阂替換太㈧6年7弓、 六、申請專利範圍 種下式N -甲基-鄰-苯二胺之磷酸鹽2.根據申請專利範圍第1項之N -甲基-鄰-苯二胺之磷酸 鹽 其特徵在於具通式I其中η為介於〇·5至1的數字。 3_根據申請專利範圍第2項之ν -甲基-鄰-苯二胺之磷酸 鹽，其中η介於〇·7至0.8之間。 4.根據申請專利範圍第2至3項中任一項之Ν -甲基-鄰-苯 二胺之磷酸鹽，其特徵為η介於〇·75至0.78之間。 5· —種製備申請專利範圍第1至4項中任一項之甲基_ 鄰·苯二胺之磷酸鹽之方法，其特徵在於將申請專利範 圍第1至4項中任一項之Ν -甲基-鄰苯二胺溶於心至。 醇類中及與結晶性或被溶解的磷酸混合。 6.根據申請專利範圍第5項之製備方法，其特徵在於原地 製備Ν ·甲基-鄰-苯二胺。 7·根據申請專利範圍第6項之製備方法，其特徵在於由鄰_ 硝基-Ν ·甲基苯胺原地製備Ν -甲基-鄰-苯二胺。 63306-960727.DOC 本紙張尺度適用中國國家標準(CNS) Α4規格(210 X 297公釐) 6 1A 09 9 12 8 8 8 8 A B c D 六、申請專利範圍 8. 根據申請專利範圍第5項之製備方法，其特徵在於N -甲 基-鄰-苯二胺及磷酸之溶劑為乙醇、丙醇或異丙醇。 9. 根據申請專利範圍第8項之製備方法，其特徵在於N -甲 基-鄰-苯二胺及磷酸之溶劑為乙醇。 63306-960727.DOC 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19917526A DE19917526C1 (de) | 1999-04-17 | 1999-04-17 | Phosphorsäuresalz von N-Methyl-o-phenylendiamin und Verfahren zu seiner Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI290916B true TWI290916B (en) | 2007-12-11 |
Family
ID=7905007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089106728A TWI290916B (en) | 1999-04-17 | 2000-04-11 | Phosphoric acid salt of an aromatic diamin |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US6169204B1 (zh) |
| EP (1) | EP1180093B1 (zh) |
| JP (1) | JP3833477B2 (zh) |
| KR (1) | KR100700909B1 (zh) |
| CN (1) | CN1161323C (zh) |
| AR (2) | AR006063A4 (zh) |
| AT (1) | ATE251114T1 (zh) |
| AU (1) | AU763072B2 (zh) |
| BG (1) | BG65020B1 (zh) |
| BR (1) | BR0009783B1 (zh) |
| CA (1) | CA2364671C (zh) |
| CO (1) | CO5160306A1 (zh) |
| CZ (1) | CZ299581B6 (zh) |
| DE (2) | DE19917526C1 (zh) |
| DK (1) | DK1180093T3 (zh) |
| EA (1) | EA003614B1 (zh) |
| EE (1) | EE04586B1 (zh) |
| EG (1) | EG22689A (zh) |
| ES (1) | ES2204546T3 (zh) |
| HK (1) | HK1043109B (zh) |
| HR (1) | HRP20010745B1 (zh) |
| HU (1) | HU223962B1 (zh) |
| IL (1) | IL145029A0 (zh) |
| MX (1) | MXPA01010468A (zh) |
| MY (1) | MY119962A (zh) |
| NO (1) | NO327533B1 (zh) |
| NZ (1) | NZ515121A (zh) |
| PE (1) | PE20010090A1 (zh) |
| PL (1) | PL194186B1 (zh) |
| PT (1) | PT1180093E (zh) |
| RS (1) | RS49893B (zh) |
| SA (1) | SA00210071B1 (zh) |
| SK (1) | SK285277B6 (zh) |
| TR (1) | TR200103003T2 (zh) |
| TW (1) | TWI290916B (zh) |
| UA (1) | UA71003C2 (zh) |
| UY (1) | UY26108A1 (zh) |
| WO (1) | WO2000063156A1 (zh) |
| ZA (1) | ZA200107904B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004040647B4 (de) * | 2004-08-20 | 2013-01-03 | Dhw Deutsche Hydrierwerke Gmbh Rodleben | Verfahren zur Herstellung von hellfarbenen, primären Fettaminen |
| US7501448B2 (en) * | 2004-10-15 | 2009-03-10 | Teva Pharmaceutical Industries, Ltd. | Process for preparing telmisartan |
| US9977667B2 (en) | 2015-09-09 | 2018-05-22 | Red Hat, Inc. | Updating software utilizing domain name system (DNS) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2142585A1 (de) * | 1971-08-20 | 1973-02-22 | Schering Ag | 2-(5-nitro-2-thiazolyl)-benzimidazole |
| CH774974A4 (zh) * | 1974-06-06 | 1976-02-13 | ||
| HU186018B (en) * | 1982-05-12 | 1985-05-28 | Magyar Asvanyolaj Es Foeldgaz | Process for preparing o-phenylene-diamine |
| US5149700A (en) * | 1990-05-30 | 1992-09-22 | American Home Products Corporation | Substituted arylsulfonamides and benzamides |
| IL98599A (en) * | 1990-06-28 | 1995-06-29 | Merck & Co Inc | Stable salts of "4-deoxy-" 4-epi-methylamino abramectin and insecticides containing them |
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1997
- 1997-04-25 AR ARM970101737U patent/AR006063A4/es unknown
-
1999
- 1999-04-17 DE DE19917526A patent/DE19917526C1/de not_active Expired - Fee Related
-
2000
- 2000-03-23 US US09/533,482 patent/US6169204B1/en not_active Expired - Lifetime
- 2000-04-11 TW TW089106728A patent/TWI290916B/zh not_active IP Right Cessation
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