DI-o-TOLYLGUANIDINE

PRODUCT IDENTIFICATION
CAS NO. 97-39-2

DI-O-TOLYLGUANIDINE

EINECS NO. 202-577-6
FORMULA (CH3C6H4NH)2C(=NH)
MOL WT. 239.32

H.S. CODE

 2925.29.0090

TOXICITY

 Rat LD50 (Oral): 500mg/kg
SYNONYMS 1,3-Ditolylguanidine; N,N'-Bis(2-methylphenyl)guanidine;
1,3-Bis(o-tolyl)guanidine; 1,3-Di-o-tolyguanidine; DOTG; DTG; Diorthotolylguanidine; N,N'-Di-o-tolueylguanidine; N,N'-Di-o-tolylguanidine; 132116-33-7; 46913-50-2; 60297-72-5;

SMILES

 c1(NC(Nc2c(cccc2)C)=N)c(cccc1)C

CLASSIFICATION

Guanidine,  Vulcanization accelerator, Anticonvulsant

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE

white to grayish powder

MELTING POINT

 175 - 178 C
BOILING POINT  
SPECIFIC GRAVITY 1.1 - 1.2

SOLUBILITY IN WATER

 Insoluble (soluble in acetone, chloroform and alcohol)
pH  
VAPOR DENSITY  
AUTOIGNITION

 

log Pow 3.99 (Octanol-water)
OH RATE 1.05E-10 (cm3/molecule-sec at 25 C Atmospheric )

REFRACTIVE INDEX

 

NFPA RATINGS

 

FLASH POINT

 

STABILITY Stable under ordinary conditions

GENERAL DESCRIPTION & EXTERNAL LINKS
Guanidine, also called carbamidine, is a strongly alkaline and water-soluble compound, NHC(NH2)2 It is formed by the oxidation of guanine in urine as a normal product of protein metabolism in the body. In industry, guanidine, containing nitrogens and N=C solid bond, and its modified derivatives are versatile intermediates used in the manufacture of plastics, resins, rubber chemicals, nitroguanidines (explosives), photo chemicals, fungicides, and disinfectant. It has also biotechnological application of protein separation, purification and as a protein denaturant. It can be used as an oxygen scavenger to prevent corrosion damage. It is used as a component of rocket propellants because it produce a large amount of heat when burned.

Di-o-tolylguanidine is used as a secondary rubber accelerator with  thiazoles, thiurams, dithiocarbamates and sulfenamides to speed the vulcanization. It is unsuitable for food-contact and medical products. It has similar activity to diphenylguanidine.

http://www.thefreelibrary.com/
.....Activators are chemicals which increase the rate of vulcanization by reacting first with the accelerators to form rubber soluble complexes. These complexes then activate the sulfur to effect vulcanization. The most common activators are combinations of zinc oxide and stearic acid. Other metal oxides have been used for specific purposes ie. lead, cadmium etc., and other fatty acids used include lauric and proprionic acids. Soluble zinc salts of fatty acid such as zinc 2-ethyl hexanoate are also available, and these "rubber soluble" activators are effective in natural rubber to produce low set, low creep compounds used in load bearing applications. Also, weak amines and amino alcohols have also been used as activators in combinations with the metal oxides.
Natural rubber usually contains sufficient fatty acid to solubilize the zinc salt. However, if the fatty acids are first extracted by acetone, the resultant "clean" natural rubber exhibits a much lower state of cure. Therefore, to insure consistent cure rate, fatty acids are usually added for insurance. Synthetic rubbers, especially the solution polymers, do not contain fatty acids and require their addition to the cure system.
Sulfenamide accelerators generally require less fatty acid because they release an amine during the vulcanization process which acts to solubilize the zinc. Guanidines as similar amine accelerators also serve to both activate and accelerate vulcanization.
Paris has systematically studied the effect of stearic acid and zinc oxide on a sulfenamide accelerated, sulfur cured natural rubber compound (ref. 16). Figure 7 dramatically shows the need for both the zinc and fatty acid activators.....
SALES SPECIFICATION

APPEARANCE

white to gray powder

INITIAL MELTING POINT

165 C

SIEVE ANALYSIS

0.1% max (+ 150 µm)

OIL CONTENT

1.0 - 2.0%

HEAT LOSS

0.3% max

ASH

0.3% max

TRANSPORTATION
PACKING 25kgs in Bag
HAZARD CLASS 6.1 (Packing Group: III)
UN NO. 2811

OTHER INFORMATION

Hazard Symbols: XN, Risk Phrases: 22, Safety Phrases: 26-36
GENERAL DESCRIPTION OF ACCELERATOR
Sulfur combines with nearly all elements. Sulfur forms ring and chain structures as it is the second only to carbon in exhibiting catenation. The 8-membered ring and shorter chain structure of sulfur molecule is important in vulcanization process which individual polymers are linked to other polymer molecules by atomic bridges. This process produces thermoset materials which are cross-linked and irreversible substances. The term thermoplastic is for high molecular weight polymers which can undergo melting-freezing cycle. Thermosets are not melted and re-molded on heating after cured. The split of sulfur 8-membered ring structure into shorter chains provides rubber vulcanization process. The split are liked with cure sites (some of the solid bonds in the molecule) on rubber molecules, resulting in forming sulfur bridges typically between 2 and 10 atoms long. Vulcanization makes rubber harder, more durable and more resistant to heating, aging and chemical attacks. The number of sulfur atoms in the sulfur bridges varies physical properties of the end products. Short bridges containing one or two sulfur atoms offer heat resistance and long bridges offer flexible property. Vulcanization can also be accomplished with certain peroxides, gamma radiation, and several other organic compounds. The principal classes of peroxide cross-linking agents are dialkyl and diaralkyl peroxides, peroxyketals and peroxyesters. Other vulcanizing agents include amine compounds for the cross-linking of fluorocarbon rubbers, metal oxides for chlorine-containing rubbers (notably zinc oxide for chloroprene rubber) and phenol-formaldehyde resins for the production of heat-resistant butyl rubber vulcanizates. Accelerator, in the rubber industry, is added with a curing agent to speed the vulcanization. Accelerators contain sulfur and nitrogen like derivatives of benzothiazole and thiocarbanilides. The popular accelerators are sulfenamides (as a delayed-action accelerators), thiazoles, thiuram sulfides, dithocarbamates and guanidines.

There are some types of rubber accelerators. They are used in combination with each other in accordance with vulcanizing and/or acid-base conditions. Some examples classified by chemical structure are as below;

  • Thiazole
    • 2-Mercaptobenzothiazole (CAS #: 149-30-4)
    • Dibenzothiazole disulfide (CAS #: 120-78-5)
    • 2-Mercaptobenzothiazole Zinc salt (CAS #: 155-04-4)
  • Sulphenamide
    • N-Cyclohexyl-2-benzothiazole sulfenamide (CAS #: 95-33-0)
    • N-Oxydienthylene-2-benzothiazole sulfenamide (CAS #: 102-77-2)
    • N-tert-butyl-2-benzothiazyl sulfenamide (CAS #: 95-31-8)
  • Guanidine
    • Diphenyl guanidine (CAS #: 102-06-7)
    • Di-o-tolylguanidine (CAS #: 97-39-2)
  • Thiuram
    • Tetramethyl thiuram disulfide (CAS #: 137-26-8)
    • Tetraethyl thiuram disulfide (CAS #: 97-77-8)
    • Tetramethyl thiuram monosulfide (CAS #: 97-74-5)
    • Isobutyl thiuram disulfide (CAS #: 3064-73-1)
    • Tetrabenzylthiuram disulfide (CAS #: 10591-85-2)
    • Dipentamethylene thiuramtetrasulfide (CAS #: 120-54-7)
  • Dithiocarbamate
    • Zinc dimethyl dithiocarbamate (CAS #: 137-30-4)
    • Zinc diethyl dithiocarbamate (CAS #: 14324-55-1)
    • Zinc dibutyl dithiocarbamate (CAS #: 136-23-2)
    • Zinc N-ethyl-dithiocarbamate (CAS #: 14634-93-6)
    • Zinc dibenzyl dithiocarbamate (CAS #: 14726-36-4)
    • Copper dimethyl dithiocarbamate (CAS #: 137-29-1)
  • Thiourea
    • Ethylene thiourea (CAS #: 96-45-7)
    • N,N'-Diethylthiourea (CAS #: 105-55-5)
    • N-N'-Diphenylthiourea (CAS #: 102-08-9)