JPS59130841A - フエニレンジアミン類の製造法 - Google Patents

フエニレンジアミン類の製造法

Info

Publication number: JPS59130841A
Authority: JP; Japan
Prior art keywords: reaction; water; compound; nitroaniline; hydrocarbon
Prior art date: 1983-01-17
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

JP58004217A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0234341B2 (2

Inventor

Kuniyasu Akiyoshi

邦康秋吉

Toshio Tanabe

田辺　稔夫

Masaki Fujimoto

昌樹藤本

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.)

1983-01-17

Filing date

1983-01-17

Publication date

1984-07-27

1983-01-17 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1983-01-17 Priority to JP58004217A priority Critical patent/JPS59130841A/ja

1984-07-27 Publication of JPS59130841A publication Critical patent/JPS59130841A/ja

1990-08-02 Publication of JPH0234341B2 publication Critical patent/JPH0234341B2/ja

Status Granted legal-status Critical Current

Links

-1 phenylenediamine compound Chemical class 0.000 title abstract description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
229930195733 hydrocarbon Natural products 0.000 claims abstract description 21
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 19
239000003054 catalyst Substances 0.000 claims abstract description 17
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
239000000203 mixture Substances 0.000 claims abstract description 12
238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 11
239000004094 surface-active agent Substances 0.000 claims abstract description 8
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 7
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims description 25
150000004986 phenylenediamines Chemical class 0.000 claims description 19
229910000564 Raney nickel Inorganic materials 0.000 claims description 17
239000007868 Raney catalyst Substances 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 8
239000000725 suspension Substances 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 abstract description 29
239000000047 product Substances 0.000 abstract description 12
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract description 9
239000007788 liquid Substances 0.000 abstract description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
238000005984 hydrogenation reaction Methods 0.000 abstract description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract description 5
238000000926 separation method Methods 0.000 abstract description 3
239000002904 solvent Substances 0.000 abstract description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract description 2
239000006227 byproduct Substances 0.000 abstract description 2
229910000510 noble metal Inorganic materials 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 abstract 2
239000012295 chemical reaction liquid Substances 0.000 abstract 1
238000000034 method Methods 0.000 description 25
229910052739 hydrogen Inorganic materials 0.000 description 23
239000001257 hydrogen Substances 0.000 description 23
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000003085 diluting agent Substances 0.000 description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 17
238000003756 stirring Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 10
150000002828 nitro derivatives Chemical class 0.000 description 9
239000012071 phase Substances 0.000 description 8
239000002002 slurry Substances 0.000 description 8
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 3
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
150000005215 alkyl ethers Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
238000004062 sedimentation Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
101000603223 Homo sapiens Nischarin Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 1
102100038995 Nischarin Human genes 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000012190 activator Substances 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001273 butane Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000004855 decalinyl group Chemical class C1(CCCC2CCCCC12)* 0.000 description 1
238000010908 decantation Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000005611 electricity Effects 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012847 fine chemical Substances 0.000 description 1
NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
SPIFDSWFDKNERT-UHFFFAOYSA-N nickel;hydrate Chemical compound O.[Ni] SPIFDSWFDKNERT-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
239000000049 pigment Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
230000003068 static effect Effects 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP58004217A 1983-01-17 1983-01-17 フエニレンジアミン類の製造法 Granted JPS59130841A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP58004217A JPS59130841A (ja)	1983-01-17	1983-01-17	フエニレンジアミン類の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58004217A JPS59130841A (ja)	1983-01-17	1983-01-17	フエニレンジアミン類の製造法

Publications (2)

Publication Number	Publication Date
JPS59130841A true JPS59130841A (ja)	1984-07-27
JPH0234341B2 JPH0234341B2 (2)	1990-08-02

Family

ID=11578444

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58004217A Granted JPS59130841A (ja)	1983-01-17	1983-01-17	フエニレンジアミン類の製造法

Country Status (1)

Country	Link
JP (1)	JPS59130841A (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100362772B1 (ko) *	2000-07-07	2002-12-11	금호석유화학 주식회사	파라페닐렌디아민의 제조방법

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5126826A (ja) *	1973-10-30	1976-03-05	Hoechst Ag	Aminobenzenjudotaino seiho
JPS5328130A (en) *	1976-08-26	1978-03-16	Asahi Chem Ind Co Ltd	Preparation of p-phenylenediamines

1983
- 1983-01-17 JP JP58004217A patent/JPS59130841A/ja active Granted

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5126826A (ja) *	1973-10-30	1976-03-05	Hoechst Ag	Aminobenzenjudotaino seiho
JPS5328130A (en) *	1976-08-26	1978-03-16	Asahi Chem Ind Co Ltd	Preparation of p-phenylenediamines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100362772B1 (ko) *	2000-07-07	2002-12-11	금호석유화학 주식회사	파라페닐렌디아민의 제조방법

Also Published As

Publication number	Publication date
JPH0234341B2 (2)	1990-08-02

Publication	Publication Date	Title
DE69222417T3 (de)	2006-11-16	Verfahren zur herstellung von 4-aminodiphenylamin
USRE44175E1 (en)	2013-04-23	Process for preparing 4-aminodiphenylamines
US3499034A (en)	1970-03-03	Hydrogenation of aromatic nitro compounds
JPS6120343B2 (2)	1986-05-21
JPS62120347A (ja)	1987-06-01	制御ニトロ化によるベンゼンあるいはベンゼン誘導体から直接に芳香族モノアミン及び芳香族ジアミンを共生産する方法と装置
US4185036A (en)	1980-01-22	Hydrogenation of mixed aromatic nitrobodies
JP2000506126A (ja)	2000-05-23	芳香族ニトロ化合物の芳香族アミンへの水素化
EP0002308A1 (en)	1979-06-13	Catalytic hydrogenation process for the manufacture of aromatic amines
EP0171052B1 (en)	1990-07-18	Conitration of mixed aromatic hydrocarbons
US2166150A (en)	1939-07-18	Catalytic hydrogenation of dinitriles to diamines
JPS60115556A (ja)	1985-06-22	４−アルコキシアニリン類の製造方法
US2166151A (en)	1939-07-18	Catalytic hydrogenation of adiponitriles to produce hexamethylene diamines
US3361819A (en)	1968-01-02	Process for producing chlorinesubstituted aromatic amines
JPS59130841A (ja)	1984-07-27	フエニレンジアミン類の製造法
US2587572A (en)	1952-02-26	Process for production of amino hydroxy compounds by hydrogenation of nitro hydroxy compounds
GB982903A (en)	1965-02-10	Process for the manufacture of aromatic amines
Hou et al.	2008	Selective partial hydrogenation of dinitrobenzenes to nitroanilines catalyzed by Ru/C
Werner	1948	Amination by reduction
US3093685A (en)	1963-06-11	Catalytic reduction of aromatic mononitro compounds
US2408171A (en)	1946-09-24	Process for preparation of 2-methyl-1, 2-propanediamine
JPH03204841A (ja)	1991-09-06	アニリンとｍ―フェニレンジアミン、芳香族モノアミンと芳香族ジアミンの協同生産の連続２段法
JPS62270550A (ja)	1987-11-24	４−アミノメチル−１，８−ジアミノオクタンの製造方法
US3366683A (en)	1968-01-30	Method for the production of benzyl anilines
US3260750A (en)	1966-07-12	Process for preparing hydrazobenzenes
US3232989A (en)	1966-02-01	Aromatic dinitro compounds

JPS59130841A - フエニレンジアミン類の製造法 - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=11578444

Family Applications (1)

Country Status (1)

Cited By (1)

Citations (2)

Patent Citations (2)

Cited By (1)

Also Published As

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