With dicyandiamide

Uses. The principal use of adiponitrile is for hydrogenation to hexamethylene diamine leading to nylon-6,6. However, as a result of BASE s new adiponitrile-to-caprolactam process, a significant fraction of ADN produced may find its way into nylon-6 production. Adipoquanamine, which is prepared by the reaction of adiponitrile with dicyandiamide [461-58-5] (cyanoguanidine), may have uses in melamine—urea amino resins (qv) (see "Benzonitrile, Uses"). Its typical Hquid nitrile properties suggest its use as an extractant for aromatic hydrocarbons. 

B.Gapud, M.Shoemake, E.Searcy, MF resins modified with dicyandiamide sorbitol for impregnation of substrates for post-formable decorative laminates, U.S Patent No.6,001,92 (1999). 

The earliest polymeric cationic aftertreatments stemmed from the development of crease-resist finishes for cellulosic fibres. One such, promoted specifically for its colour fastness improvements when applied as an aftertreatment to direct dyeings, was a condensation product of formaldehyde with dicyandiamide (Scheme 10.82). Many similar compounds followed, such as condensation products of formaldehyde with melamine (10.212), polyethylene imine) with cyanuric chloride (10.213) and alkyl chlorides with polyethylene imine) (10.214 R = alkyl). 

The preparation of alkylguanidines by fusing amine salts with dicyandiamide at 180° for three hours has been advocated [104], however it has been shown that, depending on the conditions, a guanidine or a biguanide can result [105, 106]. 

Nickel may he measured quantitatively hy several microanalytical gravimetric methods that include (l)formation of a red precipitate with dimethyl-glyoxime, (2) precipitation as a hlack sulfide with ammonium sulfide, (3) precipitating as a complex cyanide hy treating with alkali cyanide and bromine, and (4) precipitation as a yellow complex hy treating an ammoniacal solution of nickel with dicyandiamide sulfate (Grossman s reagent), followed hy the addition of potassium hydroxide. All of these methods can separate nickel from cobalt in solution. 

Chloroximes (hydroxamic acid chlorides) react with dicyandiamide to yield 5-guanido-oxadiazoles Mb)... 

The same compound has been prepared in poor yield by treating benzo-nitrile oxide with dicyandiamide (J9) (see p. 826). 

Dicyandiamide (116) reacts with a variety of two-atom components to form 2,4-diamino-1,3,5-triazines. The route, which bears some resemblance to the syntheses from biguanides (see Section 2.20.4.2.1), was discovered by Ostrogovich (11MI22000). He found that 1,3,5-triazines were prepared efficiently on heating alkyl or aryl nitriles with dicyandiamide (equation 59). 

Uses. The principal use of adiponitrile is for hydrogenation to hexamethylene diamine leading to nylon-6,6. Adipoquanamine, prepared by the reaction of adiponitrile with dicyandiamide (cyanoguanidine), has typical liquid nitrile properties that suggest its use as an extractant for aromatic hydrocarbons. 

Like acetonitrile, benzonitrile is a powerful solvent fnr many inorganic and organic materials including some polymers. It can be converted to a large number and variety of derivatives by simple syntheses e.g.. by hydrolysis, it can be converted to either benzoic acid nr benzamicle. The most important reaction is with dicyandiamide to produce 2,4-diamino-6-phenyl-l,3,5-triazine (benzogunnamine) ... 

To date, the best studied modified systems are Pt catalysts inhibited with sulfur compounds, morpholine or phosphorous compounds (ref. 5). Raney nickel modified with dicyandiamide has also been reported to be able to hydrogenate aromatic chloronitro compounds with very good selectivities and activities. Since nickel is an attractive alternative to precious metal catalysts we decided to search for other types of inhibitors and to investigate the stage at which dehaiogenation occurs. 

Figures 2a-d show plots of catalyst potential and substrate concentration (GLC) versus hydrogen consumption for the hydrogenation with formamidine acetate (a), with dicyandiamide (b), with guanidine acetate (c) and without modifier (d). This type of presentation allows to standardize and to compare reactions with different reaction times, which are indicated at the upper edge of the graphs. As expected by analogy with the results reported for the unmodified nickel catalysts (ref.9), no dehalogenation is observed as long as either nitro compounds or partially reduced intermediates are present in solution.

Carboxy-phenyl] 3(oder l) cyanguanyl -triazen-(l) 2- [Cyanoguanyl-triazeno] -benzoesaure or [2-Carboxy-benzoldiazo] dicyandiamid in Ger), HOOC.C6H4,N N.NH.C-( NH).NH.CN mw 232.20 N 36.20% yel crysts (from MeOH), mp dec ca 98° readily sol in hot ale si sol in benz, eth or chlf insol in w was prepd by treating diazotized anthranilic acid with dicyandiamid in alksoln.Its Silver salt... 

The Eastern Forest Products Laboratory (12,71) at Ottawa, Ontario, has been active in development of leach-resistant treatments using melamine or urea with dicyandiamide, formaldehyde, and phosphoric acid. Decay resistance is also shown for a urea-based treatment (72). One stystem has met the requirements for Class C wood roofing under ASTM El08 by Underwriters Laboratories of Canada (12,73). This treatment, or one similar, is expected to be introduced into the United States within the year as an approved exterior-type leach-resistant treatment. 

Melamine, a white powder, was discovered and identified by Liebig in 1834 but commercial manufacture came only in 1939, by Cyanamid Company of America with dicyandiamide as raw material. Melamine is 2,4,6-triamino-l,3,5-triazine with a structure as shown in Figure 53. On reaction with formaldehyde in aqueous solution the melamine powder dissolves rapidly on heating to form various methylol melamines, as in Figure 54. After further heating and the elimination of water the methylol melamines condense to form resinous polymers. 

Table 12.14 shows a comparison of dicyandiamide cured epoxy adhesives formulated with and without a CTBN adduct. When compared to the control epoxy, the toughened formulation exhibits significantly higher peel strength and moderately higher tensile shear strength. CTBN modified epoxy adhesives are generally one-part systems, cured with dicyandiamide at elevated temperature. 

One-component epoxy adhesive cured with dicyandiamide... 

Baumeister et al. studied the hydrogenation of various halonitrobenzenes using Raney Ni modified with amidine derivatives.115 Formamidine acetate (19b) has been found to be the most effective inhibitor for dehalogenation. It has been shown that the dehalogenation occurs as a consecutive reaction after the halogenated aniline has been formed. A typical example with use of this inhibitor is shown in eq. 9.51 for the hydrogenation of l-chloro-2,4-dinitrobenzene in comparison with dicyandiamide. It is noted that the reaction time could be shortened with 19b compared to that with 19a. 

Mes3GeN=0=NGeMes3, mp 237-238 °C, in 75% yield. Also, trietliylgermyl-N,N-diethylamine reacts with dicyandiamide 5 to give a 83 % yield of 4 ... 

The same oxide reacts with tritylcyanamide to give a 78 % yield of N-triphenylmethyl-N -triphenylstannylcarbodiimide, and bis(tributylstannyl)oxide reacts with dicyandiamide to give a 98 % yield of bis(tributylstannyl)carbodiimide. ... 

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