CN1194634A - 制备4-氰基-2,5-二氟苯胺的方法 - Google Patents
制备4-氰基-2,5-二氟苯胺的方法 Download PDFInfo
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- CN1194634A CN1194634A CN96196648A CN96196648A CN1194634A CN 1194634 A CN1194634 A CN 1194634A CN 96196648 A CN96196648 A CN 96196648A CN 96196648 A CN96196648 A CN 96196648A CN 1194634 A CN1194634 A CN 1194634A
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- Prior art keywords
- reaction
- difluoroaniline
- cyano group
- thinner
- ammonia
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- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- LAPGMTOHOQPDGI-UHFFFAOYSA-N 4-amino-2,5-difluorobenzonitrile Chemical compound NC1=CC(F)=C(C#N)C=C1F LAPGMTOHOQPDGI-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 230000008676 import Effects 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 cyclic aliphatic Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DLKNOGQOOZFICZ-UHFFFAOYSA-N 2,4,5-trifluorobenzonitrile Chemical compound FC1=CC(F)=C(C#N)C=C1F DLKNOGQOOZFICZ-UHFFFAOYSA-N 0.000 description 1
- SGZSJPBASHYOHQ-UHFFFAOYSA-N 2-chloro-5-fluorobenzoyl chloride Chemical class FC1=CC=C(Cl)C(C(Cl)=O)=C1 SGZSJPBASHYOHQ-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及制备4-氰基-2,5-二氟苯胺—一种制备除草剂或液体晶体的中间体的方法。
Description
本发明涉及制备4-氰基-2,5-二氟苯胺-一种制备除草剂或液体晶体的中间体的方法。
由2,5-二氟苯胺制备4-氰基-2,5-二氟苯胺的二步法是已知的(参见EP-A1 0 224 001)。第一步是溴化,生成4-溴-2,5-二氟苯胺。第二步是溴由氰基代替。该反应除了加入至少等摩尔量的氰化铜外,还需要大约5-倍摩尔量的10%氰化钠溶液用于后处理。明显的缺点包括氰化铜的成本和废水的处理,废水处理成问题不仅是因为结合成氰基配合物的铜,冗长的萃取后处理,特别是需要大量的二氯甲烷,而且还因为要处理大量的毒性非常大的氰化钠溶液。
业已发现,如果在增高温度下,任选在稀释剂存在下,使2,4,5-三氟苄腈与过量的氨反应,可以高收率和高纯度地获得4-氰基-2,5-二氟苯胺。
出人意外的是,即使是大量过量的氨也不产生二胺或三胺。再者,非常出人意外的是,交换只选择性地出现在4-位而不出现在2-位上。而使用2,4-二氟苄腈的类似反应,在本发明条件下,给出大致比率为1∶1的上述二种可能的胺。
需作为起始原料的2,4,5-三氟苄腈有市售商品且可以使用由2,4-二氯-5-氟苯甲酰氯通过氟化、酰胺化且随后脱水而制备。
适合于进行本发明反应的稀释剂是水、某些有机溶剂及其任一混合物。可以以例举的方式提到的稀释剂有:脂族、环脂族或芳族烃,例如,石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;卤代烃,例如氯苯或二氯苯;醚类,例如,乙醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、2-甲基四氢呋喃、1,2-二甲氧基乙烷、二甘醇二甲基醚、1,2-二乙氧基乙烷或茴香醚。原则上,使用稀释剂是优选的。优选的溶剂是二噁烷、四氢呋喃、甲苯和水。
此反应是在50至150℃,优选在80至130℃的温度下进行的。
此反应通常是在加压下进行的。优选的是,反应是在相应于在反应温度下的反应混合物的至少自压的压力下进行。压力为2至50巴表压是特别优选的。
通常,本发明反应是每摩尔的2,4,5-三氟苄腈使用1.5至50摩尔,优选2至20摩尔的氨,如果需要,0.1至3升,优选0.3至2升的稀释剂来进行的。
在本发明方法反应步骤的优选实施方案中,腈与稀释剂一起导入密闭的反应容器中,并加热至反应温度。之后将液体氨顶着容器压力,以可以保持内部温度恒定的速率泵入。
在本发明方法后处理步骤的优选实施方案中,反应完毕后,将体系冷却,将容器减压,并去除过量的氨和稀释剂,如果需要,在减压下进行。为分离4-氰基-2,5-二氟苯胺,将残留物用水搅拌,分离出晶体,用水制成淤浆,再分离出来,并最后干燥。
可以通过本发明方法制备的4-氰基-2,5-二氟苯胺可以用作例如制备除草剂或液体晶体的中间体(参见例如,EP-A1 648 772;DE-OS 38351 68;JP 02 243 676)。
实施例1
将于2000毫升四氢呋喃中的515克2,4,5-三氟苄腈导入反应釜中,并加热至100℃。之后以使温度仍保持在100至150℃的范围的速率,泵入250毫升液体氨。之后将混合物在此温度下搅拌8小时,之后冷却。压力达到最大22巴表压。在将氨吹出后,使用旋转蒸发器,将溶剂去除。残留物搅拌入500毫升水中,将置于抽吸过滤器上。抽吸过滤后,残留物再用200毫升水制成淤浆,并抽吸过滤。在40℃下于真空中干燥后,得到482克(理论值的95.4%)4-氰基-2,5-二氟苯胺,熔点99-100℃。实施例2
在大致20℃下,将4500毫升液体氨加入到3000克2,3,5-三氟苄腈的10升甲基叔丁基醚溶液中,所述的溶液预先置于40升备有锚式搅拌器的不锈钢反应釜中。除了反应混合物的自压外,注入10巴氮气,并将混合物在100℃下反应16小时。在去除未反应的氨之后,将溶剂用水萃取,在40至60℃(200至300毫巴)下蒸馏掉溶剂。获得的残留物是2839克纯产物,相当于理论收率的96.5%。
Claims (5)
1.制备4-氰基-2,5-二氟苯胺的方法,其特征在于,使2,4,5-三氟苄腈与过量的氨在增高的温度下,任选在稀释剂存在下进行反应。
2.根据权利要求1的制备4-氰基-2,5-二氟苯胺的方法,其特征在于,反应是在50至150℃的温度下进行的。
3.根据权利要求1的制备4-氰基-2,5-二氟苯胺的方法,其特征在于,反应是在增压下进行的。
4.根据权利要求1的制备4-氰基-2,5-二氟苯胺的方法,其特征在于,反应是每摩尔2,4,5-三氟苄腈使用1.5至50摩尔氨,且如果需要,使用0.1至3升稀释剂来进行的。
5.根据权利要求1的制备4-氰基-2,5-二氟苯胺的方法,其特征在于,腈与稀释剂一起导入密闭的反应容器中,并加热至反应温度,之后将液体氨顶着容器压力,以可以保持内部温度的速率泵入,反应完毕后,将体系冷却,去除过量的氨和稀释剂,如果需要,在减压下进行,将残留物用水搅拌,分离出品体,用水洗涤或用水制成淤浆,再分离出来,并最后干燥。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19531895A DE19531895A1 (de) | 1995-08-30 | 1995-08-30 | Verfahren zur Herstellung von 4-Cyano-2,5-difluoranilin |
DE19531895.1 | 1995-08-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1194634A true CN1194634A (zh) | 1998-09-30 |
CN1068869C CN1068869C (zh) | 2001-07-25 |
Family
ID=7770760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96196648A Expired - Fee Related CN1068869C (zh) | 1995-08-30 | 1996-08-19 | 制备4-氰基-2,5-二氟苯胺的方法 |
Country Status (13)
Country | Link |
---|---|
US (1) | US6075160A (zh) |
EP (1) | EP0854859B1 (zh) |
JP (1) | JPH11511443A (zh) |
KR (1) | KR19990044132A (zh) |
CN (1) | CN1068869C (zh) |
AU (1) | AU6822596A (zh) |
BR (1) | BR9610020A (zh) |
CA (1) | CA2230509A1 (zh) |
DE (2) | DE19531895A1 (zh) |
DK (1) | DK0854859T3 (zh) |
ES (1) | ES2146015T3 (zh) |
HK (1) | HK1016154A1 (zh) |
WO (1) | WO1997008136A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109678741A (zh) * | 2019-01-29 | 2019-04-26 | 金凯(辽宁)化工有限公司 | 4-氨基-3-氟苯甲酸的制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4504660A (en) * | 1982-07-06 | 1985-03-12 | American Home Products Corporation | Process for the production of 2,6-diaminobenzonitrile derivatives |
US4863959A (en) * | 1985-10-17 | 1989-09-05 | American Cyanamid Company | Anthranilonitrile derivatives as useful agents for promoting growth, improving feed efficiency, and for increasing the lean meat to fat ratio of warm-blooded animals |
DE3678252D1 (de) * | 1985-10-17 | 1991-04-25 | American Cyanamid Co | Anthranilonitrilderivate und verwandte verbindungen als nuetzliche stoffe zur wachstumsbeschleunigung, zur verbesserung der futterqualitaet und zur steigerung des fleisch/fett-verhaeltnisses bei warmbluetigen tieren. |
GB8919679D0 (en) * | 1989-08-31 | 1989-10-11 | Ici Plc | Fluorobenzene derivatives |
JPH0565250A (ja) * | 1991-01-28 | 1993-03-19 | Ishihara Sangyo Kaisha Ltd | 3,5−ジフルオロアニリンの製造方法 |
-
1995
- 1995-08-30 DE DE19531895A patent/DE19531895A1/de not_active Withdrawn
-
1996
- 1996-08-19 DE DE59605320T patent/DE59605320D1/de not_active Expired - Fee Related
- 1996-08-19 DK DK96928476T patent/DK0854859T3/da active
- 1996-08-19 ES ES96928476T patent/ES2146015T3/es not_active Expired - Lifetime
- 1996-08-19 WO PCT/EP1996/003642 patent/WO1997008136A1/de active IP Right Grant
- 1996-08-19 CN CN96196648A patent/CN1068869C/zh not_active Expired - Fee Related
- 1996-08-19 AU AU68225/96A patent/AU6822596A/en not_active Abandoned
- 1996-08-19 KR KR1019980701365A patent/KR19990044132A/ko active IP Right Grant
- 1996-08-19 BR BR9610020A patent/BR9610020A/pt not_active IP Right Cessation
- 1996-08-19 CA CA002230509A patent/CA2230509A1/en not_active Abandoned
- 1996-08-19 US US09/011,943 patent/US6075160A/en not_active Expired - Fee Related
- 1996-08-19 EP EP96928476A patent/EP0854859B1/de not_active Expired - Lifetime
- 1996-08-19 JP JP9509799A patent/JPH11511443A/ja active Pending
-
1999
- 1999-03-17 HK HK99101113A patent/HK1016154A1/xx not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109678741A (zh) * | 2019-01-29 | 2019-04-26 | 金凯(辽宁)化工有限公司 | 4-氨基-3-氟苯甲酸的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JPH11511443A (ja) | 1999-10-05 |
EP0854859A1 (de) | 1998-07-29 |
WO1997008136A1 (de) | 1997-03-06 |
DE19531895A1 (de) | 1997-03-06 |
ES2146015T3 (es) | 2000-07-16 |
BR9610020A (pt) | 1999-07-06 |
EP0854859B1 (de) | 2000-05-24 |
US6075160A (en) | 2000-06-13 |
CA2230509A1 (en) | 1997-03-06 |
KR19990044132A (ko) | 1999-06-25 |
AU6822596A (en) | 1997-03-19 |
DE59605320D1 (de) | 2000-06-29 |
HK1016154A1 (en) | 1999-10-29 |
MX9801595A (es) | 1998-05-31 |
DK0854859T3 (da) | 2000-09-25 |
MX9801604A (es) | 1998-05-31 |
CN1068869C (zh) | 2001-07-25 |
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