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822-06-0

Basic Information
CAS No.: 822-06-0
Name: Hexamethylene Diisocyanate
Article Data: 107
Molecular Structure:
Molecular Structure of 822-06-0 (Hexamethylene Diisocyanate)
Formula: C8H12N2O2
Molecular Weight: 168.195
Synonyms: Isocyanicacid, hexamethylene ester (6CI,8CI);1,6-Hexamethyldiisocyanate;1,6-Hexamethylene diisocyanate;1,6-Hexanediisocyanate;1,6-Hexylene diisocyanate;GMDI;HDI;HMDI;Hexamethylene diisocyanate;Hexamethylene diisocyanate-acrylonitrile copolymer;Hexane 1,6-diisocyanate;NSC 11687;1,6-Diisocyanatohexane;
EINECS: 212-485-8
Density: 1.01 g/cm3
Melting Point: -55 °C
Boiling Point: 255 °C at 760 mmHg
Flash Point: 140 °C
Solubility: reacts with water
Appearance: colourless liquid
Hazard Symbols: ToxicT
Risk Codes: 23-36/37/38-42/43
Safety: 26-28-38-45-28A
Transport Information: UN 2281 6.1/PG 2
PSA: 58.86000
LogP: 1.21840
Synthetic route
4223-31-8

N,N′-hexanediyl bis-carbamic acid diphenyl ester

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
at 150℃; Pyrolysis;99.8%
at 220℃; under 97.5098 Torr; Product distribution / selectivity; Industry scale;97%
at 100 - 150℃; under 11.2511 - 60.006 Torr; for 240h; Product distribution / selectivity;97%
124-09-4

1,6-Hexanediamine

103-71-9

phenyl isocyanate

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
With phosgene In chlorobenzene at 10 - 130℃; for 4 - 5h; Solvent;99.6%

N,N’-hexanediyl-di((4-tert-octylphenyl)carbamate)

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
at 280℃; under 7.50075 Torr;98%
6030-54-2

1,6-bis(methoxycarbonylamino)hexane

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
With dibutyltin dilaurate; 3-(3-methyl-1H-imidazol-3-ium-1-yl)propane-1-sulfonate at 240℃; under 20 Torr; for 2h; Temperature; Reagent/catalyst; Pressure;97.4%
With dibutyltin dilaurate In butan-1-ol at 120 - 240℃; under 20 Torr; Solvent; Temperature; Flow reactor;92.2%
With antimony(III) trioxide; vanadium(V) oxide; titanium(IV) oxide at 250℃; under 20 Torr; Temperature;83.9%
124-09-4

1,6-Hexanediamine

75-44-5

phosgene

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
In chlorobenzene at 185℃; under 30003 Torr;97%
Stage #1: 1,6-Hexanediamine With hydrogenchloride In chlorobenzene at 40℃; under 1500.15 Torr; for 2h; Flow reactor; Large scale;
Stage #2: phosgene In chlorobenzene at 130℃; under 1500.15 Torr; for 4h; Flow reactor; Large scale;
96.5%
In chlorobenzene at 97 - 160℃; under 4500.45 - 23252.3 Torr; for 7.5h;95%
124-09-4

1,6-Hexanediamine

32315-10-9

bis(trichloromethyl) carbonate

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
With triethylamine at 0 - 10℃; for 1.83333h; Inert atmosphere;96%
With triethylamine at 0 - 20℃; for 1.5h; Inert atmosphere;96%
4223-31-8

N,N′-hexanediyl bis-carbamic acid diphenyl ester

A

102-09-0

bis(phenyl) carbonate

B

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
at 150℃; under 11.2511 - 112.511 Torr;A n/a
B 95.3%
75-44-5

phosgene

6055-52-3

hexane-1,6-diamine dihydrochloride

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
Stage #1: phosgene; hexane-1,6-diamine dihydrochloride With N-benzyl-N,N,N-triethylammonium chloride In 5,5-dimethyl-1,3-cyclohexadiene at 95 - 140℃; for 5h;
Stage #2: With triethylamine
95%
6030-54-2

1,6-bis(methoxycarbonylamino)hexane

A

13590-53-9

1-isocyanato-6-methoxycarbonylaminohexane

B

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
With dibutyltin dilaurate; 3-(3-methyl-1H-imidazol-3-ium-1-yl)propane-1-sulfonate at 240℃; under 20 Torr; for 2h; Temperature; Reagent/catalyst; Pressure;A 5.2%
B 94.1%
With zinc diacetate In nitrobenzene at 160℃; for 1h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Time; Temperature;A 41 %Chromat.
B 17 %Chromat.
With Zn-2Co/ZSM-5 In chlorobenzene at 230℃; under 5100.51 Torr; for 3h; Reagent/catalyst; Inert atmosphere;
40777-33-1

hexane-1,6-diyl dicarbamate

822-06-0

Hexamethylene diisocyanate

Conditions
ConditionsYield
In chlorobenzene at 140 - 210℃; under 5250.53 Torr; for 1h; Inert atmosphere; Green chemistry;93.6%
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Consensus Reports

1,6-DIISOCYANATOHEXANE's reported in EPA TSCA Inventory.

Standards and Recommendations

ACGIH TLV: TWA 0.005 ppm
DFG MAK: 0.005 ppm (0.035 mg/m3)
NIOSH REL: (Diisocyanates) TWA 0.005 ppm; CL 0.02 ppm/10M
DOT Classification:  6.1; Label: Poison

Analytical Methods

For occupational chemical analysis use OSHA: #42.

Specification

The 1,6-Diisocyanatohexane , with cas registry number of 822-06-0, has other registry numbers including (1) 133394-59-9 ; (2) 243121-01-9 ; (3) 280144-19-6 ; (4) 53192-27-1 ; (5) 57350-77-3 ect. It belongs to the classification codes of Agricultural Chemical; Air Pollutants; Air Pollutants, occupational; Cross-Linking Reagents; Environmental Pollutants; Indicators and Reagents. Its systematic name and IUPAC name are the same which is called 1,6-diisocyanatohexane . This chemical has its several superlist names which are (1) HDI ; (2) Hexamethylene diisocyanate ; (3) Hexamethylene diisocyanate [UN2281] [Poison] ; (4) Hexamethylene diisocyanate, 1,6- ; (5) Hexamethylene-1,6-diisocyanate ; . It is a colorless crystalline solid.

Physical properties about 1,6-Diisocyanatohexane are:
(1)ACD/LogP:  3.447; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  3.45; (4)ACD/LogD (pH 7.4):  3.45; (5)ACD/BCF (pH 5.5):  245.36; (6)ACD/BCF (pH 7.4):  245.36; (7)ACD/KOC (pH 5.5):  1787.40; (8)ACD/KOC (pH 7.4):  1787.40; (9)#H bond acceptors:  4; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  7; (12)Index of Refraction:  1.483; (13)Molar Refractivity:  47.225 cm3; (14)Molar Volume:  165.276 cm3; (15)Polarizability:  18.721 10-24cm3 ; (16)Surface Tension:  39.398998260498 dyne/cm; (17)Density:  1.018 g/cm3 ; (18)Flash Point:  140 °C; (19)Enthalpy of Vaporization:  49.245 kJ/mol; (20)Boiling Point:  254.999 °C at 760 mmHg; (21)Vapour Pressure:  0.017000000923872 mmHg at 25°C.

Preparation of  1,6-Diisocyanatohexane :
 this chemical can be prepared by octanedioic acid .

This reaction needs reagent 1,8-bis (dimethylamino) naphthalene , solvent tetrahydrofuran and other condition like heating. The reaction time is 6 hours with yield of 76.1%.

Uses of  1,6-Diisocyanatohexane :
It mainly used to prepare other chemicals. Here is a example, it can react with 2-hydrazino-ethanol to give hexamethylenedi[2-(b-hydroxyethyl)-4-semicarbazide] .

This reaction is a kind of addition reaction. It occurs in solvent propan-2-ol at temperature of 10 ℃. The yield is about 89%.

Safety information of 1,6-Diisocyanatohexane :
When you are using this chemical, please be cautious about it as the following:Poison by inhalation and intravenous routes. Moderately toxic by ingestion and skin contact. Potentially explosive reaction with alcohols and base. When heated to decomposition it emits toxic fumes of NOx.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C=N\CCCCCC/N=C=O;
(2)InChI:InChI=1/C8H12N2O2/c11-7-9-5-3-1-2-4-6-10-8-12/h1-6H2;
(3)InChIKey:RRAMGCGOFNQTLD-UHFFFAOYAI

The toxicity data of 1,6-Diisocyanatohexane is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 30mg/m3 (30mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 74, 1982.
mouse LD50 intravenous 5600ug/kg (5.6mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07805,
mouse LD50 oral 350mg/kg (350mg/kg)   Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 39, Pg. 202, 1980.
rabbit LD50 skin 570uL/kg (0.57mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rat LCLo inhalation 60mg/m3/4H (60mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 12(10), Pg. 40, 1968.
rat LD50 oral 710uL/kg (0.71mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.