JPH0412261B2 - - Google Patents

Info

Publication number: JPH0412261B2
Authority: JP; Japan
Prior art keywords: anilines; reaction; alkynyl; butadiene; chloro
Prior art date: 1984-04-13
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.): Expired

Application number

JP7447284A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60218359A (ja

Inventor

Ko Horino

Atsushi Hayashi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Zeon Corp

Original Assignee

Nippon Zeon Co Ltd

Priority date (The priority date 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 date listed.)

1984-04-13

Filing date

1984-04-13

Publication date

1992-03-04

1984-04-13 Application filed by Nippon Zeon Co Ltd filed Critical Nippon Zeon Co Ltd

1984-04-13 Priority to JP7447284A priority Critical patent/JPS60218359A/ja

1985-11-01 Publication of JPS60218359A publication Critical patent/JPS60218359A/ja

1992-03-04 Publication of JPH0412261B2 publication Critical patent/JPH0412261B2/ja

Status Granted legal-status Critical Current

Links

150000001448 anilines Chemical class 0.000 claims description 19
238000004519 manufacturing process Methods 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
FBSZAHKIQXIJJG-UHFFFAOYSA-N 4-chlorobuta-1,2-diene Chemical compound ClCC=C=C FBSZAHKIQXIJJG-UHFFFAOYSA-N 0.000 description 7
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002994 raw material Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
-1 -butynyl)-2 Chemical class 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000012433 hydrogen halide Substances 0.000 description 4
229910000039 hydrogen halide Inorganic materials 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 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
239000000376 reactant Substances 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QCSGBUUEKXTMGI-UHFFFAOYSA-N 1-bromobuta-1,2-diene Chemical compound CC=C=CBr QCSGBUUEKXTMGI-UHFFFAOYSA-N 0.000 description 1
OKWUYBGGPXXFLS-UHFFFAOYSA-N 1-chlorobut-2-yne Chemical compound CC#CCCl OKWUYBGGPXXFLS-UHFFFAOYSA-N 0.000 description 1
KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 1
VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 1
SLNVSARGOSPIPA-UHFFFAOYSA-N 4-bromobuta-1,2-diene Chemical compound BrCC=C=C SLNVSARGOSPIPA-UHFFFAOYSA-N 0.000 description 1
HSTQZOGEDVASKB-UHFFFAOYSA-N 4-iodobuta-1,2-diene Chemical compound ICC=C=C HSTQZOGEDVASKB-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000000034 method Methods 0.000 description 1
AXJMLZYMKQODSE-UHFFFAOYSA-N n-but-2-ynylaniline Chemical compound CC#CCNC1=CC=CC=C1 AXJMLZYMKQODSE-UHFFFAOYSA-N 0.000 description 1
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
LVMTVPFRTKXRPH-UHFFFAOYSA-N penta-1,2-diene Chemical compound CCC=C=C LVMTVPFRTKXRPH-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP7447284A 1984-04-13 1984-04-13 Ｎ−（２−アルキニル）アニリン類の製造方法 Granted JPS60218359A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP7447284A JPS60218359A (ja)	1984-04-13	1984-04-13	Ｎ−（２−アルキニル）アニリン類の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP7447284A JPS60218359A (ja)	1984-04-13	1984-04-13	Ｎ−（２−アルキニル）アニリン類の製造方法

Publications (2)

Publication Number	Publication Date
JPS60218359A JPS60218359A (ja)	1985-11-01
JPH0412261B2 true JPH0412261B2 (fr)	1992-03-04

Family

ID=13548226

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7447284A Granted JPS60218359A (ja)	1984-04-13	1984-04-13	Ｎ−（２−アルキニル）アニリン類の製造方法

Country Status (1)

Country	Link
JP (1)	JPS60218359A (fr)

1984
- 1984-04-13 JP JP7447284A patent/JPS60218359A/ja active Granted

Also Published As

Publication number	Publication date
JPS60218359A (ja)	1985-11-01

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