US991721A - Process of producing beta-methyltetramethylene-diamin. - Google Patents

Process of producing beta-methyltetramethylene-diamin. Download PDF

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Publication number
US991721A
US991721A US52954609A US1909529546A US991721A US 991721 A US991721 A US 991721A US 52954609 A US52954609 A US 52954609A US 1909529546 A US1909529546 A US 1909529546A US 991721 A US991721 A US 991721A
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United States
Prior art keywords
diamin
methyltetramethylene
producing beta
beta
germany
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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
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US52954609A
Inventor
Fritz Hofmann
Carl Coutelle
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Bayer AG
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Farbenfabriken Vorm Friedr Bayer and Co
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Priority to US52954609A priority Critical patent/US991721A/en
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Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/50—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of carboxylic acid amides

Definitions

  • Our invention relates to a new and valuable process for producing beta-methyltetramethylene-dlamin.
  • the new process consists in treating the diamid of beta-methyladipic acid in 10 parts of hot water is added. After heating for a short time to 70-80" C. the product of the reaction is neutralized with BrH and then concentrated by evaporation. Sodium bromid separates which is filtered Application filed November 28, 1909. Serial No. 529,546.
  • the filtrate contains part of the BrX a and the bromohydrate of the base (NHi. GH -CH-CHz-CHFN H2) from which the latter base is set freeby treating the solution with caustic soda.
  • the free base is isolated in the form of an oil, it is dried and finally purified by distillation.
  • the process for producing beta-methyl tetramethylene-diamin which process con- .sists in treating the diamid of beta-methyladipic acid with an aqueous solution at halogen in caustic alkaline 'lyes and isolating .the free base by treating the halogen salt with alkali, substantially as described.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adornments (AREA)
  • Materials For Medical Uses (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Description

UNITED STATES PATENT OFFICE.
FRITZ HOEMANN AND CARL FARBENFABRIKEN VORM. CORPORATION OF GERMANY.
COUTELLE,
FRIEDR. BAYER & C
013 ELBERFELD, GERMANY, ASSIGNORS TO 0., OF ELBERIEELD, GERMANY, A
PROCESS OF PRODUCING BETA-METHYLTETRAMETHYLENE-DIAMIN.
No Drawing,
Specification of Letters Patent.
Patented May 9, 1 911.
. To all whom it may camera:
Be it known that-we, FRITZ HOFMANN and CARL ComELLE, doctors of philosophy, chemists, citizens of the German Empire, residing at Elberfeld, Germany, have invented new and useful Improvements in Processes for Producing Beta-h/Iethyltetramethylene-Diamin, of which the following is a specification.
Our invention relates to a new and valuable process for producing beta-methyltetramethylene-dlamin.
which is a valuable intermediate compound for the production of pharmaceutical compounds, dyestufl's, etc.
The new process consists in treating the diamid of beta-methyladipic acid in 10 parts of hot water is added. After heating for a short time to 70-80" C. the product of the reaction is neutralized with BrH and then concentrated by evaporation. Sodium bromid separates which is filtered Application filed November 28, 1909. Serial No. 529,546.
oil. The filtrate contains part of the BrX a and the bromohydrate of the base (NHi. GH -CH-CHz-CHFN H2) from which the latter base is set freeby treating the solution with caustic soda. The free base is isolated in the form of an oil, it is dried and finally purified by distillation.
The "formation ofthe product takes probably place accordingto the following formula:
The process is carried out in an analogous manner on using instead of bronnn the equivalent amount of chlorin. In this case the product of'the reaction is neutralized with hydrochloric acid.
The process for producing beta-methyl tetramethylene-diamin, which process con- .sists in treating the diamid of beta-methyladipic acid with an aqueous solution at halogen in caustic alkaline 'lyes and isolating .the free base by treating the halogen salt with alkali, substantially as described.
set our hand in the presence of two subscribmg Witnesses.
FRITZ HOFMANN. 1 5. CARL COUTELLE. a 3.
Witnesses -O'r'ro Keno,
CHAS. J. WRIGHT.
In testimony whereof we have hereunto- (so I
US52954609A 1909-11-23 1909-11-23 Process of producing beta-methyltetramethylene-diamin. Expired - Lifetime US991721A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US52954609A US991721A (en) 1909-11-23 1909-11-23 Process of producing beta-methyltetramethylene-diamin.

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US52954609A US991721A (en) 1909-11-23 1909-11-23 Process of producing beta-methyltetramethylene-diamin.

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US991721A true US991721A (en) 1911-05-09

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198348A (en) * 1977-06-14 1980-04-15 Snia Viscosa Societa Nazionale Industria Applicazioni Viscosa S.P.A. Process for the preparation of amines
US5410082A (en) * 1993-05-11 1995-04-25 Pfirmann; Ralf Process for preparing amines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198348A (en) * 1977-06-14 1980-04-15 Snia Viscosa Societa Nazionale Industria Applicazioni Viscosa S.P.A. Process for the preparation of amines
US5410082A (en) * 1993-05-11 1995-04-25 Pfirmann; Ralf Process for preparing amines

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