JPS591450A - ｏ−フエニレンジアミンの製造方法 - Google Patents

ｏ−フエニレンジアミンの製造方法

Info

Publication number: JPS591450A
Authority: JP; Japan
Prior art keywords: ammonia; hydrogen; phenylenediamine; reactor; catalyst
Prior art date: 1982-05-12
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.): Pending

Application number

JP58081058A

Other languages

English (en)

Japanese (ja)

Inventor

レズソ・クシコス

ゼノ・トロクサニイ

ペテロ・ハムメリ

ズソルト・バルガ

ヨズセフ・バソリイ

ラヨス・キスゲルゲリイ

ジユラ・キンチエス

サンドル・イエレン

エレメル・フルタク

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.)

Magyar Asvanyolaj es Foldgaz Kiserleti Intezet

Original Assignee

Magyar Asvanyolaj es Foldgaz Kiserleti Intezet

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.)

1982-05-12

Filing date

1983-05-11

Publication date

1984-01-06

1983-05-11 Application filed by Magyar Asvanyolaj es Foldgaz Kiserleti Intezet filed Critical Magyar Asvanyolaj es Foldgaz Kiserleti Intezet

1984-01-06 Publication of JPS591450A publication Critical patent/JPS591450A/ja

Status Pending legal-status Critical Current

Links

GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title claims description 30
238000004519 manufacturing process Methods 0.000 title description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 81
229910052739 hydrogen Inorganic materials 0.000 claims description 45
239000001257 hydrogen Substances 0.000 claims description 44
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
229910021529 ammonia Inorganic materials 0.000 claims description 37
239000003054 catalyst Substances 0.000 claims description 27
238000000034 method Methods 0.000 claims description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 15
239000000460 chlorine Chemical group 0.000 claims description 8
229910052801 chlorine Chemical group 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
238000002425 crystallisation Methods 0.000 claims description 5
230000008025 crystallization Effects 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000000638 solvent extraction Methods 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 26
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
235000019270 ammonium chloride Nutrition 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
230000008020 evaporation Effects 0.000 description 9
239000007789 gas Substances 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
239000006227 byproduct Substances 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
239000007791 liquid phase Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
150000001412 amines Chemical class 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000006096 absorbing agent Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000012467 final product Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical group ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-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
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 2
PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
-1 chloroform Chemical compound 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000008240 homogeneous mixture Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000001495 arsenic compounds Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
210000003296 saliva Anatomy 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
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP58081058A 1982-05-12 1983-05-11 ｏ−フエニレンジアミンの製造方法 Pending JPS591450A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU1487/82		1982-05-12
HU821487A HU186018B (en)	1982-05-12	1982-05-12	Process for preparing o-phenylene-diamine

Publications (1)

Publication Number	Publication Date
JPS591450A true JPS591450A (ja)	1984-01-06

Family

ID=10954685

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58081058A Pending JPS591450A (ja)	1982-05-12	1983-05-11	ｏ−フエニレンジアミンの製造方法

Country Status (8)

Country	Link
JP (1)	JPS591450A (de)
CH (1)	CH655093A5 (de)
DD (1)	DD270208A3 (de)
DE (1)	DE3316465A1 (de)
FR (1)	FR2526790B1 (de)
GB (1)	GB2122607B (de)
HU (1)	HU186018B (de)
IT (1)	IT1164222B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR006063A4 (es) *	1999-04-17	1999-08-11	Romario S R L	Bandeja termica para pizzas
CN106316863A (zh) *	2016-08-13	2017-01-11	安徽东至广信农化有限公司	一种邻苯二胺的高效回收方法
CN109879762B (zh) *	2019-03-27	2022-02-22	宁夏瑞泰科技股份有限公司	一种邻苯二胺的提纯方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3230259A (en) *	1963-04-09	1966-01-18	Universal Oil Prod Co	Preparation of o-phenylenediamines
GB1344796A (en) *	1971-08-14	1974-01-23	Hoechst Ag	Process for the preparation of aromatic diamines
JPS532427A (en) *	1976-06-25	1978-01-11	Mitsui Toatsu Chem Inc	Preparation of phenylenediamine
HU175397B (hu) *	1977-08-12	1980-07-28	Magyar Asvanyolaj Es Foeldgaz	Sposob poluchenija o-fenilen-diamina

1982
- 1982-05-12 HU HU821487A patent/HU186018B/hu not_active IP Right Cessation
1983
- 1983-05-05 DE DE19833316465 patent/DE3316465A1/de not_active Withdrawn
- 1983-05-06 GB GB08312557A patent/GB2122607B/en not_active Expired
- 1983-05-10 FR FR8307783A patent/FR2526790B1/fr not_active Expired
- 1983-05-10 CH CH2553/83A patent/CH655093A5/de not_active IP Right Cessation
- 1983-05-11 JP JP58081058A patent/JPS591450A/ja active Pending
- 1983-05-11 DD DD83250843A patent/DD270208A3/de not_active IP Right Cessation
- 1983-05-12 IT IT21066/83A patent/IT1164222B/it active

Also Published As

Publication number	Publication date
FR2526790B1 (fr)	1988-02-05
DD270208A3 (de)	1989-07-26
GB2122607A (en)	1984-01-18
FR2526790A1 (fr)	1983-11-18
IT8321066A0 (it)	1983-05-12
GB8312557D0 (en)	1983-06-08
IT8321066A1 (it)	1984-11-12
HU186018B (en)	1985-05-28
IT1164222B (it)	1987-04-08
CH655093A5 (de)	1986-03-27
GB2122607B (en)	1986-01-29
DE3316465A1 (de)	1983-11-17

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