Dicyclohexylcarbodiimide

1.Introduction of Dicyclohexylcarbodiimide

Dicyclohexylcarbodiimide,with its CAS NO.538-75-0,is a kind of white or slight yellow crystalline solid. It has synonyms of 1,3-Dicyclohexylcarbodiimide ; Bis(cyclohexyl)carbodiimide ; Carbodicyclohexylimide ; DCC ; DCCD ; DCCI ; N,N'-Dicyclohexylcarbodiimide ; N,N'-Methanetetraylbiscyclohexaamine and NSC 30022. Dicyclohexylcarbodiimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P₂O₅ or SOCl₂ generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NO_x). Dicyclohexylcarbodiimide is incompatible with acids and oxidizing agents. It is probably combustible.

2.Properties of Dicyclohexylcarbodiimide

(1) Molecular Weight 206.32718 [g/mol]  (2) Molecular Formula C13H22N2  (3) XLogP3-AA 4.7
(4) H-Bond Acceptor 2  (5) Rotatable Bond Count 2  (6) Exact Mass 206.178299
(7) MonoIsotopic Mass 206.178299  (8) Topological Polar Surface Area 24.7  (9) Heavy Atom Count 15 
(10) Complexity 201  (11) Covalently-Bonded Unit Count 1  (12) Feature 3D Acceptor Count 2
(13) Feature 3D Cation Count 1  (14) Feature 3D Ring Count 2 (15) Effective Rotor Count 4.4
(16) Conformer Sampling RMSD 0.6  (17) CID Conformer Count 23
 

3.Structure descriptors of  Dicyclohexylcarbodiimide

Canonical SMILES: C1CCC(CC1)N=C=NC2CCCCC2
InChI: InChI=1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2
InChIKey: QOSSAOTZNIDXMA-UHFFFAOYSA-N
 

4.Safety information of Dicyclohexylcarbodiimide

Hazard Codes: T,Xn
Risk Statements: 23/24/25-34-40-43-41-36/38-21-24-22-62-37/38-10-61
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed
R34: Causes burns
R40: Limited evidence of a carcinogenic effect
R43: May cause sensitization by skin contact
R41: Risk of serious damage to eyes
R36/38: Irritating to eyes and skin
R21: Harmful in contact with skin
R24: Toxic in contact with skin
R22: Harmful if swallowed
R62: Possible risk of impaired fertility
R37/38: Irritating to respiratory system and skin
R10: Flammable
R61: May cause harm to the unborn child
Safety Statements: 26-36/37/39-45-41-24-37/39-24/25-36-16-53
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
S41: In case of fire and/or explosion do not breathe fumes
S24: Avoid contact with skin
S37/39: Wear suitable gloves and eye/face protection
S24/25: Avoid contact with skin and eyes
S36: Wear suitable protective clothing
S16: Keep away from sources of ignition - No smoking
S53: Avoid exposure - obtain special instruction before use
RIDADR: UN 2922 8/PG 2
WGK Germany: 3
RTECS: FF2160000
F: 3-8-10-21: Hygroscopic. Photosensitive. Keep under argon. Sensitive to humidity.
HazardClass: 6.1
PackingGroup: II
 

5.Production of Dicyclohexylcarbodiimide

Dicyclohexylcarbodiimide has several synthesis methods. Pri-Bara et al. use palladium acetate, iodine, and oxygen to couple cyclohexyl amine and cyclohexyl isocyanide. 
C₆H₁₁NC + C₆H₁₁NH₂ + O₂ → (C₆H₁₁N)₂C + H₂O
Tang et al. condense two isocyanates using the catalyst OP(MeNCH₂CH₂)₃N in yields of 92%:

 Dicyclohexylcarbodiimide has also been made from dicyclohexylurea using a phase transfer catalyst by Jaszay et al. The disubstituted urea, arenesulfonyl chloride, and potassium carbonate react in toluene in the presence of benzyl trimethylammonium chloride to give Dicyclohexylcarbodiimide in 50% yield.

6.Toxity data of Dicyclohexylcarbodiimide