JPS6067454A - ポリクロロベンゾニトリル類の製造方法 - Google Patents

ポリクロロベンゾニトリル類の製造方法

Info

Publication number: JPS6067454A
Authority: JP; Japan
Prior art keywords: dichlorotoluene; bromine; catalyst; reaction; bromide
Prior art date: 1983-09-24
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

Application number

JP17670783A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0244464B2 (2

Inventor

Hiroshi Hayamizu

宏速水

Yasuo Kuroda

泰男黒田

Makoto Kikuchi

菊地　孚

Kenji Koshi

古志　健二

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.)

Nippon Kayaku Co Ltd

Original Assignee

Nippon Kayaku 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.)

1983-09-24

Filing date

1983-09-24

Publication date

1985-04-17

1983-09-24 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1983-09-24 Priority to JP17670783A priority Critical patent/JPS6067454A/ja

1984-09-21 Priority to DE8484111258T priority patent/DE3468411D1/de

1984-09-21 Priority to EP19840111258 priority patent/EP0141228B1/en

1985-04-17 Publication of JPS6067454A publication Critical patent/JPS6067454A/ja

1990-10-04 Publication of JPH0244464B2 publication Critical patent/JPH0244464B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
238000006243 chemical reaction Methods 0.000 claims abstract description 35
239000003054 catalyst Substances 0.000 claims abstract description 23
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052794 bromium Inorganic materials 0.000 claims abstract description 13
229910021529 ammonia Inorganic materials 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
239000001301 oxygen Substances 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
239000007789 gas Substances 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims description 2
DMEDNTFWIHCBRK-UHFFFAOYSA-N 1,3-dichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Cl DMEDNTFWIHCBRK-UHFFFAOYSA-N 0.000 abstract description 13
RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methyl-benzene Natural products CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 abstract description 13
238000000034 method Methods 0.000 abstract description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract description 4
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
239000004009 herbicide Substances 0.000 abstract description 2
229910000042 hydrogen bromide Inorganic materials 0.000 abstract description 2
239000012808 vapor phase Substances 0.000 abstract 2
239000003905 agrochemical Substances 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
239000002994 raw material Substances 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 11
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 7
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 7
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000008187 granular material Substances 0.000 description 2
VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
OHDYZVVLNPXKDX-UHFFFAOYSA-N 2,3-dichlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1Cl OHDYZVVLNPXKDX-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
UEAVUAACIHROJL-UHFFFAOYSA-N [O-2].[O-2].[V+5].[Fe+2] Chemical compound [O-2].[O-2].[V+5].[Fe+2] UEAVUAACIHROJL-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
-1 bromine compound Chemical class 0.000 description 1
150000004768 bromobenzenes Chemical class 0.000 description 1
AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
229950005228 bromoform Drugs 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
230000002363 herbicidal effect Effects 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
OGUCKKLSDGRKSH-UHFFFAOYSA-N oxalic acid oxovanadium Chemical compound [V].[O].C(C(=O)O)(=O)O OGUCKKLSDGRKSH-UHFFFAOYSA-N 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/28—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing six-membered aromatic rings, e.g. styrene
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP17670783A 1983-09-24 1983-09-24 ポリクロロベンゾニトリル類の製造方法 Granted JPS6067454A (ja)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
JP17670783A JPS6067454A (ja)	1983-09-24	1983-09-24	ポリクロロベンゾニトリル類の製造方法
DE8484111258T DE3468411D1 (en)	1983-09-24	1984-09-21	A process for producing polychlorobenzonitrile
EP19840111258 EP0141228B1 (en)	1983-09-24	1984-09-21	A process for producing polychlorobenzonitrile

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP17670783A JPS6067454A (ja)	1983-09-24	1983-09-24	ポリクロロベンゾニトリル類の製造方法

Publications (2)

Publication Number	Publication Date
JPS6067454A true JPS6067454A (ja)	1985-04-17
JPH0244464B2 JPH0244464B2 (2)	1990-10-04

Family

ID=16018344

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP17670783A Granted JPS6067454A (ja)	1983-09-24	1983-09-24	ポリクロロベンゾニトリル類の製造方法

Country Status (3)

Country	Link
EP (1)	EP0141228B1 (2)
JP (1)	JPS6067454A (2)
DE (1)	DE3468411D1 (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113024412A (zh) *	2021-03-23	2021-06-25	上海立科化学科技有限公司	2,4,6-三氯苯腈的制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2187712B (en) *	1986-03-11	1990-05-23	Tetra Pak Finance & Trading	Fluid pack and process for the production therof
CN1055028C (zh) *	1997-01-13	2000-08-02	武汉大学	氨氧化法制2,6-二氯苯腈的新型催化剂
AU2003242614A1 (en)	2002-06-04	2003-12-19	Tessenderlo Chemie S.A.	Method for the preparation of halogenated benzonitriles

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4010188A (en) *	1968-06-24	1977-03-01	Standard Oil Company	Catalytic conversion of saturated hydrocarbons to unsaturated products by oxidation in the presence of a halogen
JPS5390238A (en) *	1977-01-14	1978-08-08	Nippon Kayaku Co Ltd	Preparation of arom. cyano cpds.
SU759506A1 (ru) *	1977-12-15	1980-08-30	Inst Teoreticheskikh Khim T An	СПОСОБ ПОЛУЧЕНИЯ ЗАМЕЩЁННЫХ БЕНЗОНИТРИЛОВ ί

1983
- 1983-09-24 JP JP17670783A patent/JPS6067454A/ja active Granted
1984
- 1984-09-21 DE DE8484111258T patent/DE3468411D1/de not_active Expired
- 1984-09-21 EP EP19840111258 patent/EP0141228B1/en not_active Expired

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4010188A (en) *	1968-06-24	1977-03-01	Standard Oil Company	Catalytic conversion of saturated hydrocarbons to unsaturated products by oxidation in the presence of a halogen
JPS5390238A (en) *	1977-01-14	1978-08-08	Nippon Kayaku Co Ltd	Preparation of arom. cyano cpds.
SU759506A1 (ru) *	1977-12-15	1980-08-30	Inst Teoreticheskikh Khim T An	СПОСОБ ПОЛУЧЕНИЯ ЗАМЕЩЁННЫХ БЕНЗОНИТРИЛОВ ί

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113024412A (zh) *	2021-03-23	2021-06-25	上海立科化学科技有限公司	2,4,6-三氯苯腈的制备方法

Also Published As

Publication number	Publication date
JPH0244464B2 (2)	1990-10-04
EP0141228B1 (en)	1988-01-07
DE3468411D1 (en)	1988-02-11
EP0141228A1 (en)	1985-05-15

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JPH0132820B2 (2)	1989-07-10
US6727370B1 (en)	2004-04-27	Method for preparing oxydiphthalic anhydrides using bicarbonate as catalyst
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JPH0272132A (ja)	1990-03-12	フェノールの製法
US3527819A (en)	1970-09-08	Oxychlorination process for preparing trichloroethylene and tetrachloroethylene
JPH0244464B2 (2)	1990-10-04
US4530797A (en)	1985-07-23	Process for producing polychlorobenzonitrile
JPS582233B2 (ja)	1983-01-14	フタロニトリルの調製方法
US3089909A (en)	1963-05-14	Production of unsaturated aliphatic aldehydes
US2828325A (en)	1958-03-25	Production of benzonitrile
JPS5998031A (ja)	1984-06-06	トリフルオロアセチルクロライドの製造方法
US3326961A (en)	1967-06-20	Method for preparing acrylonitrile
US2615054A (en)	1952-10-21	Vinyl chloride preparation
JPS5892630A (ja)	1983-06-02	メタンの部分酸化法
JPS625420B2 (2)	1987-02-04
JPS585188B2 (ja)	1983-01-29	アクリロニトリルの製造方法
JPS58109471A (ja)	1983-06-29	インド−ル類の製法
JP2001179094A (ja)	2001-07-03	アクリロニトリルまたはメタクリロニトリル製造用触媒
JPS5939413B2 (ja)	1984-09-22	メタクロレインとメタクリル酸の製造方法
JP3487516B2 (ja)	2004-01-19	フェノキシ置換ベンゾニトリルの製造法
JPS58121270A (ja)	1983-07-19	インド−ル類の製法

JPS6067454A - ポリクロロベンゾニトリル類の製造方法 - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (3)

Applications Claiming Priority (1)

Publications (2)

Family

ID=16018344

Family Applications (1)

Country Status (3)

Cited By (1)

Families Citing this family (3)

Citations (3)

Patent Citations (3)

Cited By (1)

Also Published As

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