GB717232A - Improvements in or relating to fluorinated amines - Google Patents

Improvements in or relating to fluorinated amines

Info

Publication number
GB717232A
GB717232A GB5620/51A GB562051A GB717232A GB 717232 A GB717232 A GB 717232A GB 5620/51 A GB5620/51 A GB 5620/51A GB 562051 A GB562051 A GB 562051A GB 717232 A GB717232 A GB 717232A
Authority
GB
United Kingdom
Prior art keywords
prepared
acid
amine
fluorocarbon
formula
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
Application number
GB5620/51A
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.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
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 Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of GB717232A publication Critical patent/GB717232A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/15—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 1,1 - dihydro - perfluoroalkylamines of the formula CnF2n+1CH2NH2 where n is an integer from 3 to 17, their salts and their N-substituted amide derivatives of the formula RCONHCH2CnF2n+1, where RCO is an acyl radical of a monocarboxylic acid. The amines are prepared by reducing a perfluorocarboxamide of the general formula CnF2n+1CONH2 in dry ether solution under an inert atmosphere with lithium aluminium hydride. The fluorocarbon amides can be prepared by reacting the corresponding fluorocarbon acid fluorides or alkyl esters with ammonia. The fluorocarbon acid fluorides, having the formula CnF2n+1COF can be prepared by electrolysis of a solution of anhydrous liquid hydrogen fluoride containing in solution the corresponding hydrocarbon carboxylic acid of formula CnH2n+1COOH or its anhydride at a cell voltage insufficient under the conditions of reaction to generate free fluorine. The amines may be isolated as their insoluble sulphates or hydrochlorides from which the free amine is liberated by treatment with caustic alkali. Water may be removed by distillation from freshly calcined calcium oxide. In examples: (1) 1,1-dihydroheptafluorobutylamine is prepared by the reduction with lithium aluminium hydride of heptafluorobutyramide in ether. The product is isolated as its bi-sulphate, and the free base is liberated by adding alkali to the dried salt followed by distillation. From the mother liquors from the amine bisulphate there may be isolated heptafluorobutyric acid, and heptafluorobutyraldehyde hydrate (C3F7CH (OH)2) which may be converted into the aldehyde C3F7CHO by dehydration. Dihydropentafluoropropylamine is prepared similarly, but is isolated as its hydrochloride, the aldehyde hydrate by-product being first removed by extraction with ether of the sulphuric acid solution of the amine. 1,1-Dihydrotrifluoroethylamine is prepared similarly, preferably in a tetrahydrofuran reaction mixture. (2) 1,1-Dihydrononadecafluorodecylamine is prepared similarly by reduction of n-nonadecafluorocapric amide. Physical constants of compounds CnF2n+1CH2NH2, in which n is 3 to 1 (inclusive) are given. The products of the invention can be diazotized and the resulting diazo compounds purified by distillation. With acids stronger than acetic acid, e.g. with fluorocarbon carboxylic acids, the amines form salts. Reaction of the amines with carboxylic acid anhydrides yields amides of the formula R.CONH.CH2CnF2n+1, where R.CO is the acyl radical corresponding to the anhydride, such as C3F7CONHCH2C3F7 by reaction with heptafluorobutyric anhydride, and CH3CONHCH2 C3F7 by reaction with acetic anhydride, of the corresponding fluorocarbon amine. The hydrochloride p C3F7CH2NH2.HCl, and the amine C9F19CH2NH2 and its hydrochloride can be sublimed. Specifications 670,991, 676,273 and U.S.A. Specification 2,348,321 are referred to.
GB5620/51A 1950-03-13 1951-03-08 Improvements in or relating to fluorinated amines Expired GB717232A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US717232XA 1950-03-13 1950-03-13

Publications (1)

Publication Number Publication Date
GB717232A true GB717232A (en) 1954-10-27

Family

ID=22103159

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5620/51A Expired GB717232A (en) 1950-03-13 1951-03-08 Improvements in or relating to fluorinated amines

Country Status (1)

Country Link
GB (1) GB717232A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3086946A (en) * 1960-06-06 1963-04-23 Research Corp Fluoroamidines and condensation products thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3086946A (en) * 1960-06-06 1963-04-23 Research Corp Fluoroamidines and condensation products thereof

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