CS244623B1 - Method of p-phenylendiamide's derivatives preparation - Google Patents

Method of p-phenylendiamide's derivatives preparation Download PDF

Info

Publication number: CS244623B1
Authority: CS; Czechoslovakia
Prior art keywords: ethanol; reduction; ethyl; methyl; cast iron
Prior art date: 1984-03-31

Application number

CS842446A

Other languages

Czech (cs)

English (en)

Other versions

CS244684A1 (en

Inventor

Jiri Terc

Arnost Bartos

Jana Cervinkova

Miroslav Pokorny

Jiri Bilek

Original Assignee

Jiri Terc

Arnost Bartos

Jana Cervinkova

Miroslav Pokorny

Jiri Bilek

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.)

1984-03-31

Filing date

1984-03-31

Publication date

1986-08-14

1984-03-31 Application filed by Jiri Terc, Arnost Bartos, Jana Cervinkova, Miroslav Pokorny, Jiri Bilek filed Critical Jiri Terc

1984-03-31 Priority to CS842446A priority Critical patent/CS244623B1/cs

1985-02-04 Priority to DD27309185A priority patent/DD256800A3/de

1985-02-11 Priority to SU857773740A priority patent/SU1694572A1/ru

1985-09-17 Publication of CS244684A1 publication Critical patent/CS244684A1/cs

1986-08-14 Publication of CS244623B1 publication Critical patent/CS244623B1/cs

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 7
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 title claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
150000002828 nitro derivatives Chemical class 0.000 claims description 19
230000009467 reduction Effects 0.000 claims description 17
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
229910001018 Cast iron Inorganic materials 0.000 claims description 13
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 12
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 4
229910052742 iron Inorganic materials 0.000 claims description 4
239000003792 electrolyte Substances 0.000 claims description 3
239000002245 particle Substances 0.000 claims description 3
150000004989 p-phenylenediamines Chemical class 0.000 claims description 2
238000006722 reduction reaction Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000000047 product Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000011701 zinc Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 4
238000002955 isolation Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
238000011946 reduction process Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000010802 sludge Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
QIOYLWJGCRELQX-UHFFFAOYSA-N 2-(4-amino-n-ethyl-3-methylanilino)ethanol;sulfuric acid;hydrate Chemical compound O.OS(O)(=O)=O.OCCN(CC)C1=CC=C(N)C(C)=C1 QIOYLWJGCRELQX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
230000004913 activation Effects 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
238000005530 etching Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
KUWCVCMJPABJDI-UHFFFAOYSA-N n-[2-(4-amino-n-ethyl-3-methylanilino)ethyl]methanesulfonamide;sulfuric acid;dihydrate Chemical compound O.O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CS(=O)(=O)NCCN(CC)C1=CC=C(N)C(C)=C1.CS(=O)(=O)NCCN(CC)C1=CC=C(N)C(C)=C1 KUWCVCMJPABJDI-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
229910001060 Gray iron Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000394605 Viola striata Species 0.000 description 1
MPLZNPZPPXERDA-UHFFFAOYSA-N [4-(diethylamino)-2-methylphenyl]azanium;chloride Chemical compound [Cl-].CC[NH+](CC)C1=CC=C(N)C(C)=C1 MPLZNPZPPXERDA-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229940006199 ferric cation Drugs 0.000 description 1
229960004887 ferric hydroxide Drugs 0.000 description 1
229940045203 ferrous cation Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
-1 iron-water-ethanol Chemical compound 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
NPKFETRYYSUTEC-UHFFFAOYSA-N n-[2-(4-amino-n-ethyl-3-methylanilino)ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCN(CC)C1=CC=C(N)C(C)=C1 NPKFETRYYSUTEC-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000009738 saturating Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1

Landscapes

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

CS842446A 1984-03-31 1984-03-31 Method of p-phenylendiamide's derivatives preparation CS244623B1 (en)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CS842446A CS244623B1 (en)	1984-03-31	1984-03-31	Method of p-phenylendiamide's derivatives preparation
DD27309185A DD256800A3 (de)	1984-03-31	1985-02-04	Verfahren zur gewinnung von p-phenylendiamin-derivaten der allgemeinen formel i
SU857773740A SU1694572A1 (ru)	1984-03-31	1985-02-11	Способ получени солей производных п-фенилендиамина

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS842446A CS244623B1 (en)	1984-03-31	1984-03-31	Method of p-phenylendiamide's derivatives preparation

Publications (2)

Publication Number	Publication Date
CS244684A1 CS244684A1 (en)	1985-09-17
CS244623B1 true CS244623B1 (en)	1986-08-14

Family

ID=5361632

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS842446A CS244623B1 (en)	1984-03-31	1984-03-31	Method of p-phenylendiamide's derivatives preparation

Country Status (3)

Country	Link
CS (1)	CS244623B1 (de)
DD (1)	DD256800A3 (de)
SU (1)	SU1694572A1 (de)

1984
- 1984-03-31 CS CS842446A patent/CS244623B1/cs unknown
1985
- 1985-02-04 DD DD27309185A patent/DD256800A3/de unknown
- 1985-02-11 SU SU857773740A patent/SU1694572A1/ru active

Also Published As

Publication number	Publication date
DD256800A3 (de)	1988-05-25
SU1694572A1 (ru)	1991-11-30
CS244684A1 (en)	1985-09-17

Publication	Publication Date	Title
FI78457B (fi)	1989-04-28	Foerfarande foer framstaellning av propargylammoniumklorider.
PL177669B1 (pl)	1999-12-31	Sposób wytwarzania 2-alkilo-6-metylo-N-(1-metoksypropylo-2)-anilin i sposób wytwarzania chloroacetanilidów
EP0773923B1 (de)	2000-04-26	Verfahren zur herstellung von halosubstituierter aromatischer säure
US4788331A (en)	1988-11-29	Method of preparing 5-amino salicylic acid
US2241769A (en)	1941-05-13	Sulphonic acid derivatives of aryl diamines
CS244623B1 (en)	1986-08-14	Method of p-phenylendiamide's derivatives preparation
US3441602A (en)	1969-04-29	1,1 - diphenyl - 1 - lower alkoxy - 3 - or - 4-amino-alkanes and the salts thereof
JPH0245452A (ja)	1990-02-15	４‐クロロ‐２，５‐ジメトキシアニリンの製造方法
US2446519A (en)	1948-08-10	Process for preparing aminophenols
EP0415595A1 (de)	1991-03-06	Fluorbenzol-Derivate
JPH0249299B2 (de)	1990-10-29
RU2308448C1 (ru)	2007-10-20	Способ получения этилендиамин-n, n, n`, n`-тетрапропионовой кислоты
US5523472A (en)	1996-06-04	Process for the preparation of 5-fluoroanthranilic acid
US4718994A (en)	1988-01-12	Method for preparing hydroxy compounds of aromatic and heteroaromatic series
JPH01308268A (ja)	1989-12-12	ベンゾトリアゾール誘導体およびそれを含有するカルボン酸類分析用試薬
US4179476A (en)	1979-12-18	Semi-continuous process for obtaining amino compounds
JPS6357574A (ja)	1988-03-12	イミダゾ−ル類の製造法
RU2268261C2 (ru)	2006-01-20	Способ получения динатриевой соли фенилен-бис-бензимидазол-тетрасульфоновой кислоты
SU437270A1 (ru)	1974-07-25	Способ получени ароматических оксиальдегидов
US3927098A (en)	1975-12-16	Process for the preparation of 2-amino-4-nitro-anisole
RU2044725C1 (ru)	1995-09-27	Способ получения тиогликолиевой кислоты или ее натриевой или моноэтаноламиновой соли
JPS6389691A (ja)	1988-04-20	両性界面活性剤の製造方法
SU552023A3 (ru)	1977-03-25	Способ получени 3,5-динитро-4-замещени аминофенилалкилсульфонов
CN1063170C (zh)	2001-03-14	一步法制备2－萘肼的方法
JPS63280055A (ja)	1988-11-17	２，６−ナフタレンジスルホン酸の製造方法