GB599713A - Manufacture of alkyl-substituted dicyandiamides - Google Patents
Manufacture of alkyl-substituted dicyandiamidesInfo
- Publication number
- GB599713A GB599713A GB2615645A GB2615645A GB599713A GB 599713 A GB599713 A GB 599713A GB 2615645 A GB2615645 A GB 2615645A GB 2615645 A GB2615645 A GB 2615645A GB 599713 A GB599713 A GB 599713A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyano
- methylisothiourea
- alkyl
- similarly
- isopropyl
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- AMIOZQPEOJWSTP-UHFFFAOYSA-N C(C)(C)N(C(SC)=N)C#N Chemical compound C(C)(C)N(C(SC)=N)C#N AMIOZQPEOJWSTP-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 239000000243 solution Substances 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 3
- JOZLTXPMBGUZGJ-UHFFFAOYSA-N C(C)N(C(SC)=N)C#N Chemical compound C(C)N(C(SC)=N)C#N JOZLTXPMBGUZGJ-UHFFFAOYSA-N 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N Isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-Butylamine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N Picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 230000001476 alcoholic Effects 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- 230000003993 interaction Effects 0.000 abstract 2
- NSDDRJXKROCWRZ-UHFFFAOYSA-N 1-isothiocyanato-2-methylpropane Chemical compound CC(C)CN=C=S NSDDRJXKROCWRZ-UHFFFAOYSA-N 0.000 abstract 1
- WPAJZLYKRSMHFO-UHFFFAOYSA-N C(#N)N(C(SC)=N)CCC Chemical compound C(#N)N(C(SC)=N)CCC WPAJZLYKRSMHFO-UHFFFAOYSA-N 0.000 abstract 1
- VKXFHZOVCZYUFV-UHFFFAOYSA-N C(C(C)C)N(C(SC)=N)C#N Chemical compound C(C(C)C)N(C(SC)=N)C#N VKXFHZOVCZYUFV-UHFFFAOYSA-N 0.000 abstract 1
- VPRRPNKDHNXJFM-UHFFFAOYSA-N C(CCC)N(C(SC)=N)C#N Chemical compound C(CCC)N(C(SC)=N)C#N VPRRPNKDHNXJFM-UHFFFAOYSA-N 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical compound CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 0.000 abstract 1
- JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- FCQJEPASRCXVCB-UHFFFAOYSA-N flavianic acid Chemical class C1=C(S(O)(=O)=O)C=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FCQJEPASRCXVCB-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- CIRSLBTYBPGMNO-UHFFFAOYSA-N methyl N-cyano-N-methylcarbamimidothioate Chemical compound CSC(=N)N(C)C#N CIRSLBTYBPGMNO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000003139 primary aliphatic amines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012047 saturated solution Substances 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alkyl-substituted dicyandiamides of the general formula R-NH-C( : NR1)-NH-CN, wherein R represents an alkyl (or cycloalkyl) group and R1 hydrogen or an alkyl (or cycloalkyl) group, are manufactured by the interaction of N-alkyl-N1-cyano-S-alkylisothioureas, of the general formula R.N = C(SR11)-NH-CN (wherein R11 represents a lower alkyl group), with ammonia or a primary aliphatic amine. In examples: (1) N-methyl-N1-cyano-S-methylisothiourea is heated in a closed vessel with a saturated solution of ammonia in ethanol to produce o -methyldicyandiamide; the product may be coverted into its salts with picric and flavianic acids by mixing alcoholic solutions of the acids and the base; (2) N - ethyl - N1 - cyano - S - methylisothiourea similarly yields o -ethyldicyandiamide and its picric and flavianic acid salts; (3) N-isopropyl-N1-cyano-S-methylisothiourea similarly yields o -isopropyldicyandiamide; (4) N-n-propyl-N1-cyano-S-methylisothiourea similarly yields o -n-propyldicyandiamide; (5) N-n-butyl-N1-cyano-S-methylisothiourea similarly yields o -n-butyldicyandiamide; (6) N-isobutyl-N1-cyano-S-methylisothiourea similarly yields o -isobutyldicyandiamide; (7) the alcoholic ammonia in (1) is replaced by aqueous methylamine solution, producing o : o 1-dimethyldicyandiamide; (8) aqueous ethylamine solution similarly yields o - methyl - o 1 - ethyldicyandiamide; (9) n-butylamine (in ethanol) similarly yields o -methyl - o 1 - n - butyldicyandiamide; (10) N-isopropyl - N1 - cyano - S - methylisothiourea is heated in a closed vessel with n-propylamine to give o - n - propyl - o 1 - isopropyldicyandiamide; (11) N - ethyl - N1 - cyano - S - methylisothiourea and isopropylamine similarly yield N2 - ethyl - N3 - isopropyldicyandiamide; (12) N - isopropyl - N1 - cyano - S - methylisothiourea and aqueous ethylamine solution yield the same product; (13) N - isopropyl - N1 - cyano - S - methylisothiourea and isopropylamine similarly yield N2 : N3-di-isopropyldicyandiamide; (14) n-butylamine similarly yields N2 - isopropyl - N3 - n - butyldicyandiamide; (15) cyclohexylamine similarly yields N2 - isopropyl - N3 - - cyclohexyldicyandiamide. Specification 599,714 is referred to. N-Alkyl-N1-cyano-S-alkylisothioureas are obtainable by the interaction of the appropriate alkyl isothioeyanate (e.g. methyl, ethyl, n- or iso-propyl or n- or iso-butyl isothiocyanate) with sodium cyanamide in alcohol, and alkylation of the resulting N-alkyl-N1-cyanoisothiourea sodium salt, e.g. with methyl iodide.
Publications (1)
Publication Number | Publication Date |
---|---|
GB599713A true GB599713A (en) | 1948-03-18 |
Family
ID=1739848
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2615645A Expired GB599713A (en) | 1945-10-08 | Manufacture of alkyl-substituted dicyandiamides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB599713A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5387656A (en) * | 1990-07-23 | 1995-02-07 | Alliedsignal Inc. | Substituted cyanoguanidines as curing agents for epoxy resins |
-
1945
- 1945-10-08 GB GB2615645A patent/GB599713A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5387656A (en) * | 1990-07-23 | 1995-02-07 | Alliedsignal Inc. | Substituted cyanoguanidines as curing agents for epoxy resins |
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