GB742340A - Improvements in or relating to diaminoadiponitriles - Google Patents

Improvements in or relating to diaminoadiponitriles

Info

Publication number
GB742340A
GB742340A GB27395/53A GB2739553A GB742340A GB 742340 A GB742340 A GB 742340A GB 27395/53 A GB27395/53 A GB 27395/53A GB 2739553 A GB2739553 A GB 2739553A GB 742340 A GB742340 A GB 742340A
Authority
GB
United Kingdom
Prior art keywords
bis
dimethylamino
butadiene
hydrogen cyanide
adiponitrile
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
GB27395/53A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas 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 Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB742340A publication Critical patent/GB742340A/en
Expired legal-status Critical Current

Links

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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles

Landscapes

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

Abstract

The invention comprises diamino-adiponitriles having the general formula <FORM:0742340/IV(a)/1> wherein R1, R2, R5 and R6 taken individually represent hydrocarbon groups; R1 and R2 and R5 and R6 when taken together represent divalent chains which form heterocycles with the nitrogen; and R3 and R4 represent hydrogen or hydrocarbon groups. The compounds are prepared by reacting hydrogen cyanide with 1 : 4 - diamino - 1 : 3 - butadienes of the general formula <FORM:0742340/IV(a)/2> at between 0 DEG and 100 DEG C., preferably in the presence of an inert organic solvent. The products are corrosion inhibitors; also they may be converted into quaternary ammonium salts having bactericidal and insecticidal properties and into amides, esters, salts and acids. In examples (1) 1 : 4-bis(dimethylamino-1 : 3-butadiene is added to a solution of hydrogen cyanide in diisopropyl ether yielding 2 : 5-bis(dimethylamino) adiponitrile having insecticidal properties; the nitrile may be alkylated with methyl iodide in dimethylformamide forming the quaternary iodide, which on treatment with aqueous silver hydroxide yields the free quaternary base convertible to any desired salt by reaction with the appropriate acid; treatment of the diamino adiponitrile with hot aqueous sulphuric acid yields 2 : 5-bis(dimethylamino) adipamide which is converted into dimethyl or diethyl 2 : 5-bis (dimethylamino) adipate by heating with methanol or ethanol and sulphuric acid; (2) hydrogen cyanide is added to 1 : 4-dimorpholino-1 : 3-butadiene in dioxane yielding 2 : 5-dimorpholino-adiponitrile; (3) 2 : 2 : 4 : 11 : 13 : 13 - hexamethyl - 6 : 9 - bis (dimethylamino) - 6 : 8 - tetradecadiene is added to hydrogen cyanide in pentane yielding 2 : 2 : 4 : 11 : 13 : 13 - hexamethyl - 6 : 9 - bis (dimethylamino) - 6 : 9 - dicyanotetradecane from which the 6 : 9-diamido derivative is obtained by alkaline hydrolysis; 4-morpholino-1 - dimethylamino - 1 : 3 - pentadiene and 1-morpholino - 1 - phenyl - 4 - dimethylamino-1 : 3 - butadiene may be used likewise; (4) hydrogen cyanide is added to 1 : 4-dipyrrolidino-1 : 5-butadiene in ether giving 2 : 5-bis (pyrrolidino) adiponitrile. Other specified butadiene starting materials include 1 : 4 - bis (din - butylamino), 1 : 4 - bis (N - methyl - N-octylamino), 1 : 4 - bis (diallylamino), 1 : 4 - dipiperidino, 1 : 4 - bis(N - methyl - N - phenylamino), 1 : 4 - bis (dicyclohexylamino), 1 : 4-diphenyl - 1 : 4 - bis (dimethylamino) and 1 : 4-bis (dimethylamino) - 1 : 4 - bis (2 : 4 : 4 - trimethylpentyl), - 1 : 3 - butadienes and those of the above formula wherein R1 and R2 or R5 and R6 represent -CH2CH2SCH2CH2-. The diamino butadienes may be prepared by isomerization of the corresponding diaminobutynes <FORM:0742340/IV(a)/3> for example as described in Specification 742,342, the butynes being obtained by Reppe's procedure from appropriate secondary amines and aldehydes and acetylene.
GB27395/53A 1952-10-23 1953-10-06 Improvements in or relating to diaminoadiponitriles Expired GB742340A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US742340XA 1952-10-23 1952-10-23

Publications (1)

Publication Number Publication Date
GB742340A true GB742340A (en) 1955-12-21

Family

ID=22118474

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27395/53A Expired GB742340A (en) 1952-10-23 1953-10-06 Improvements in or relating to diaminoadiponitriles

Country Status (1)

Country Link
GB (1) GB742340A (en)

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