US2013180A - Process of preparing diazonium compounds from 4-aminodiarylamines - Google Patents

Process of preparing diazonium compounds from 4-aminodiarylamines Download PDF

Info

Publication number
US2013180A
US2013180A US714205A US71420534A US2013180A US 2013180 A US2013180 A US 2013180A US 714205 A US714205 A US 714205A US 71420534 A US71420534 A US 71420534A US 2013180 A US2013180 A US 2013180A
Authority
US
United States
Prior art keywords
parts
solution
water
amino
diazotization
Prior art date
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 - Lifetime
Application number
US714205A
Other languages
English (en)
Inventor
Koch Wilhelm
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.)
General Aniline Works Inc
Original Assignee
General Aniline Works Inc
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.)
Filing date
Publication date
Application filed by General Aniline Works Inc filed Critical General Aniline Works Inc
Application granted granted Critical
Publication of US2013180A publication Critical patent/US2013180A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films

Definitions

  • the present invention relates to a process of preparing diazonium compounds from fi-aminodiarylamines;"more particularly it relates to ⁇ a process which comprises diazotizing a li-aminodiarylamine in a Georgianitride, the pH-value of which is between 1 and 4.
  • Probst describes a series of complications which are liable tooccur in the diazotization'of-aminodiphenylamine and the derivatives thereof and which he proposes toavoid by a particular kind of diazotization. He states on page 15 of his publication that simultaneously withthe diazotizationanother process takesplace the nal result of which is Ythat part of the Ll-arninodiarylamine is split with formation of a para- Vquinone from the aryl radical carrying the amino-group and of a diazonium compound from thesecond aryl radical.
  • This invention is based on the observation that Vthe coursebffthe diazotization of the aminodiarylamines depends on the acidity of the reaction medium and that no cleavage by oxidation occurs if. the diazotization iscarried outl in a medium thepI-I-value of which is between l ande.
  • reaction media there may be used aqueous solutions of salts, for instance, of zinc chloride,
  • the base may be ground, if desired, with the addition of a suitable'suspending or dispersing agent; or it maybe dissolved previously in a solvent miscible with water, Vsuch as Vacetone or alcohol, so that ⁇ if such a solution is mined with the aqueous reaction liquid the-baseis obtained in a iinely divided form.
  • a suitable'suspending or dispersing agent or it maybe dissolved previously in a solvent miscible with water, Vsuch as Vacetone or alcohol, so that ⁇ if such a solution is mined with the aqueous reaction liquid the-baseis obtained in a iinely divided form.
  • the base for instance, in a zinc chloride solution with sodiumA nitrite'or Zinc nitrite, the zinc chloride double salts of the diarylamino- Ll-diazcniumchlorides are directly obtained.
  • diphenylamines or-naphthylphenylamines or biphenyl-phenylamines and ani thracylphenylamines in which an amino group -portance for the production of ice colors of the 2.3-hydroxynaphthoic ⁇ acid arylaxnide seriesi
  • the process of this ⁇ invention has a high technical value. It allows of producing the diazonium salts of the bases without secondary reactions in a pure form. Furthermore, itis only by employingthis invention that the technical utilization of a number ofjbases of this kind for dyestui u manufacturing purposes ble.
  • ferrous sulfate there may also be used solutions of, for instance, 360 parts of copper chloride hydrate in 5000 parts of Water or of 3300 parts of copper sulfate hydrate in 5000 parts of water or of 530 parts of aluminium sulfate of the formula Alz(SO4)3.l2I-I2O in 6000 parts of Water, or the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Paper (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US714205A 1933-03-07 1934-03-05 Process of preparing diazonium compounds from 4-aminodiarylamines Expired - Lifetime US2013180A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE434725X 1933-03-07

Publications (1)

Publication Number Publication Date
US2013180A true US2013180A (en) 1935-09-03

Family

ID=6506667

Family Applications (1)

Application Number Title Priority Date Filing Date
US714205A Expired - Lifetime US2013180A (en) 1933-03-07 1934-03-05 Process of preparing diazonium compounds from 4-aminodiarylamines

Country Status (3)

Country Link
US (1) US2013180A (fr)
FR (1) FR769810A (fr)
GB (1) GB434725A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2691649A (en) * 1951-12-14 1954-10-12 Nat Distillers Prod Corp Diazotizing of glycine esters
US2691650A (en) * 1951-12-14 1954-10-12 Nat Distillers Prod Corp Diazotizing of glycine esters
US2825724A (en) * 1958-03-04 Diazotizing aryl amines
US2827449A (en) * 1958-03-18 Process of diazotization of aromatic
US3423391A (en) * 1963-11-28 1969-01-21 Basf Ag Continuous diazotization process

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL69026C (fr) * 1948-02-14

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2825724A (en) * 1958-03-04 Diazotizing aryl amines
US2827449A (en) * 1958-03-18 Process of diazotization of aromatic
US2691649A (en) * 1951-12-14 1954-10-12 Nat Distillers Prod Corp Diazotizing of glycine esters
US2691650A (en) * 1951-12-14 1954-10-12 Nat Distillers Prod Corp Diazotizing of glycine esters
US3423391A (en) * 1963-11-28 1969-01-21 Basf Ag Continuous diazotization process

Also Published As

Publication number Publication date
FR769810A (fr) 1934-09-03
GB434725A (en) 1935-09-09

Similar Documents

Publication Publication Date Title
US1962111A (en) Stable tetrazomonoazo compounds and their preparation
US2346531A (en) Azole disazo dye compounds and their manufacture
US2013180A (en) Process of preparing diazonium compounds from 4-aminodiarylamines
US1308071A (en)
US1218654A (en) Ureids and thioureids.
EP0068338B1 (fr) Procédé de préparation de phényldiazosulfonates
DE2358080A1 (de) Azofarbstoff-stoffzusammensetzungen
US2080191A (en) Complex metal compounds of disazo dyestuffs
US4720541A (en) Process for improving the application properties of disazo pigments
US733280A (en) Red azo dye and process of making same.
DE2555515A1 (de) Verfahren zur monodiazotierung von aromatischen diaminen
US2809964A (en) Process of preparing lower alkyl substituted aminoazoanilines
US333042A (en) Bkecht
US2027066A (en) Solid mineral acid diazonium salts and a process of preparing them
US1867937A (en) Stable diazo preparations and process of making same
US2191820A (en) Process for the preparation of 2-nitronaphthalene-4, 8-disulphonic acid
US2067132A (en) Solid diazo salts
US310155A (en) Leo vigk
US2156141A (en) Heterocyclic azo compounds and a method of producing the same
US2138559A (en) Diazo compounds and process of making same
US1635168A (en) Benzoxazolon arsonic acids
US1880442A (en) Purification of r-acid
US2012307A (en) Production of nitro-arylamines
US2036530A (en) Conversion products of n-nitramines of primary aromatic amines nitrated in the nucleus and process of making same
US2198300A (en) Hydroxylated 2-aryl-pseudonaphthazimides