CA1092124A - Procede de fabrication d'amines aromatiques - Google Patents

Procede de fabrication d'amines aromatiques

Info

Publication number: CA1092124A
Authority: CA; Canada
Prior art keywords: parts; alkyl; chloro; group; amine
Prior art date: 1976-11-17
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.): Expired

Application number

CA291,029A

Other languages

English (en)

Inventor

Massimo Stolfi

Enzo Rosati

Saverio Frigerio

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.)

Aziende Colori Nazionali Affini ACNA SpA

Original Assignee

Aziende Colori Nazionali Affini ACNA SpA

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.)

1976-11-17

Filing date

1977-11-16

Publication date

1980-12-23

1977-11-16 Application filed by Aziende Colori Nazionali Affini ACNA SpA filed Critical Aziende Colori Nazionali Affini ACNA SpA

1980-12-23 Application granted granted Critical

1980-12-23 Publication of CA1092124A publication Critical patent/CA1092124A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 29
150000004982 aromatic amines Chemical class 0.000 title claims abstract description 10
238000002360 preparation method Methods 0.000 title claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 12
239000002904 solvent Substances 0.000 claims description 23
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
235000011149 sulphuric acid Nutrition 0.000 claims description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
125000004181 carboxyalkyl group Chemical group 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
150000001491 aromatic compounds Chemical class 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
239000012429 reaction media Substances 0.000 claims description 6
239000001117 sulphuric acid Substances 0.000 claims description 6
238000005576 amination reaction Methods 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims 6
125000000547 substituted alkyl group Chemical group 0.000 claims 4
235000003891 ferrous sulphate Nutrition 0.000 claims 3
239000011790 ferrous sulphate Substances 0.000 claims 3
230000015572 biosynthetic process Effects 0.000 abstract description 6
238000003786 synthesis reaction Methods 0.000 abstract description 5
239000012847 fine chemical Substances 0.000 abstract description 2
239000013067 intermediate product Substances 0.000 abstract description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
229960001701 chloroform Drugs 0.000 description 12
239000000047 product Substances 0.000 description 10
125000003118 aryl group Chemical group 0.000 description 9
239000000758 substrate Substances 0.000 description 9
238000000605 extraction Methods 0.000 description 8
MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
230000021962 pH elevation Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000003054 catalyst Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 4
CIQJWKNJDQKPPO-UHFFFAOYSA-N 1-chloropiperidine Chemical compound ClN1CCCCC1 CIQJWKNJDQKPPO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
-1 aromatic amine compounds Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
239000000987 azo dye Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000002826 coolant Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
229960003893 phenacetin Drugs 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
239000003643 water by type Substances 0.000 description 2
XPMONGRYKYAUSP-UHFFFAOYSA-N 1-chloro-4-methylpiperazine Chemical compound CN1CCN(Cl)CC1 XPMONGRYKYAUSP-UHFFFAOYSA-N 0.000 description 1
LZDQPXAJNKGROO-UHFFFAOYSA-N 2-(dimethylamino)-n-phenylacetamide Chemical compound CN(C)CC(=O)NC1=CC=CC=C1 LZDQPXAJNKGROO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000011068 loading method Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
XVAIDCNLVLTVFM-UHFFFAOYSA-N methacetin Chemical compound COC1=CC=C(NC(C)=O)C=C1 XVAIDCNLVLTVFM-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
KEEBHMMBUBEEOV-UHFFFAOYSA-N n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CC=C1 KEEBHMMBUBEEOV-UHFFFAOYSA-N 0.000 description 1
DJEKCANOAKSYPG-UHFFFAOYSA-N n-(chloromethyl)-1-phenylmethanamine Chemical compound ClCNCC1=CC=CC=C1 DJEKCANOAKSYPG-UHFFFAOYSA-N 0.000 description 1
MTHIAHVNZDWREN-UHFFFAOYSA-N n-chloro-n-methylethanamine Chemical compound CCN(C)Cl MTHIAHVNZDWREN-UHFFFAOYSA-N 0.000 description 1
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
101150100282 rplK gene Proteins 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

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

CA291,029A 1976-11-17 1977-11-16 Procede de fabrication d'amines aromatiques Expired CA1092124A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2941776A IT1067024B (it)	1976-11-17	1976-11-17	Procedimento per la preparazione di ammine aromatiche
IT29417A/76		1976-11-17

Publications (1)

Publication Number	Publication Date
CA1092124A true CA1092124A (fr)	1980-12-23

Family

ID=11226944

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA291,029A Expired CA1092124A (fr)	1976-11-17	1977-11-16	Procede de fabrication d'amines aromatiques

Country Status (10)

Country	Link
JP (1)	JPS5363331A (fr)
BE (1)	BE860921A (fr)
CA (1)	CA1092124A (fr)
CH (1)	CH629745A5 (fr)
DE (1)	DE2750951A1 (fr)
ES (1)	ES464205A1 (fr)
FR (1)	FR2397393A1 (fr)
GB (1)	GB1595498A (fr)
IT (1)	IT1067024B (fr)
NL (1)	NL7712428A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2134130A (en) *	1983-01-21	1984-08-08	Yorkshire Chemicals Ltd	Disperse azo dyes

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL6717121A (fr) *	1965-10-29	1968-06-28
NL7800026A (nl) *	1977-01-07	1978-07-11	Acna	Werkwijze voor de bereiding van gesubstitueerde amino-benzenen.

1976
- 1976-11-17 IT IT2941776A patent/IT1067024B/it active
1977
- 1977-11-11 NL NL7712428A patent/NL7712428A/xx not_active Application Discontinuation
- 1977-11-14 CH CH1389577A patent/CH629745A5/it not_active IP Right Cessation
- 1977-11-14 JP JP13579077A patent/JPS5363331A/ja active Pending
- 1977-11-14 GB GB4736177A patent/GB1595498A/en not_active Expired
- 1977-11-15 DE DE19772750951 patent/DE2750951A1/de not_active Withdrawn
- 1977-11-16 CA CA291,029A patent/CA1092124A/fr not_active Expired
- 1977-11-16 FR FR7734444A patent/FR2397393A1/fr not_active Withdrawn
- 1977-11-16 ES ES464205A patent/ES464205A1/es not_active Expired
- 1977-11-17 BE BE182695A patent/BE860921A/fr unknown

Also Published As

Publication number	Publication date
CH629745A5 (en)	1982-05-14
IT1067024B (it)	1985-03-12
FR2397393A1 (fr)	1979-02-09
JPS5363331A (en)	1978-06-06
ES464205A1 (es)	1978-07-16
BE860921A (fr)	1978-05-17
GB1595498A (en)	1981-08-12
NL7712428A (nl)	1978-05-19
DE2750951A1 (de)	1978-05-18

Legal Events

Date	Code	Title	Description
1997-12-23	MKEX	Expiry

Publication	Publication Date	Title
JPS6393735A (ja)	1988-04-25	（２，２）−パラシクロフアンおよびその誘導体の製造方法
GB2081715A (en)	1982-02-24	Novel 5-phenylcarbamoylbarbituric acid compounds
CA1092124A (fr)	1980-12-23	Procede de fabrication d'amines aromatiques
CA1092125A (fr)	1980-12-23	Procede d'obtention d'amino-phenyl-urees et d'amino- carbanylates
US4225534A (en)	1980-09-30	Process for the production of 2-chlorobenzonitrile derivatives
US4421694A (en)	1983-12-20	Process for the preparation of nitroanilines
US2895991A (en)	1959-07-21	New chloromethylated amlides
ES435756A1 (es)	1977-04-01	Procedimiento para la preparacion de amidas aromaticas de compuestos heterociclicos.
US4727188A (en)	1988-02-23	Preparation of o,o'-dithiodibenzamides
US3254094A (en)	1966-05-31	3-imino-2, 1-benzisothiazoles
CA1209589A (fr)	1986-08-12	Methode de preparation d'anilines pouvant etre halogenees
US2849465A (en)	1958-08-26	New compounds and methods of making same
US3737449A (en)	1973-06-05	Production of hydroxybenzonitriles
DE69406885T2 (de)	1998-04-09	Verfahren zur Herstellung von Säurechloriden
US4292446A (en)	1981-09-29	Aniline derivatives
US2961465A (en)	1960-11-22	Alkali metal derivatives of di-nu-substituted formamides
CA1130305A (fr)	1982-08-24	Procede d'obtention de 2-naphtaleneethanimidamides disubstituees en n,n' et de leurs intermediaires
US4081436A (en)	1978-03-28	Process for dry quaternization of azo compounds
US3105833A (en)	1963-10-01	4, 5-dihydroxy-piperidazines and their production
EP0618199B1 (fr)	1997-08-13	Procédé pour la préparation de triazolecarboxamides
JPH029882A (ja)	1990-01-12	フタロシアニン類の製造法
CA1119179A (fr)	1982-03-02	Procede d'obtention de composes a base de n-tritylimidazole
CA1189536A (fr)	1985-06-25	Derives du nitroarylalcoylsulfone, gametocytocides
US5298606A (en)	1994-03-29	Process for the preparation of substituted azoxycyanides
US5908955A (en)	1999-06-01	Process for producing alkyl 3-amino-4-substituted benzoates