Trimethylhydroquinone Property

Melting point:

169-172 °C (lit.)

Boiling point:

295 °C (759.8513 mmHg)

Density 

0.9595 (rough estimate)

vapor pressure 

0-0.017Pa at 20-50℃

refractive index 

1.4464 (estimate)

Flash point:

191 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

methanol: 0.1 g/mL, clear

pka

11.28±0.28(Predicted)

form 

Crystalline Powder

color 

Beige

Water Solubility 

2 g/L (20 ºC)

BRN 

1909183

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

AUFZRCJENRSRLY-UHFFFAOYSA-N

LogP

3.32 at 25℃

Dissociation constant

10.8-12.9

CAS DataBase Reference

700-13-0(CAS DataBase Reference)

NIST Chemistry Reference

Trimethylhydroquinone(700-13-0)

EPA Substance Registry System

1,4-Benzenediol, 2,3,5-trimethyl- (700-13-0)

Safety

Hazard Codes 

Xn,N

Risk Statements 

20-37/38-41-43-50/53

Safety Statements 

24-26-37/39-60-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

2

RTECS 

MX7820000

F 

9-23

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29072990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H332Harmful if inhaled

H335May cause respiratory irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Trimethylhydroquinone Chemical Properties,Usage,Production

The intermediate of Vitamin E

Trimethylhydroquinone and isophytol are two intermediate in the synthesis of vitamin E, currently trimethylhydroquinone in world market is mainly produced by BASF and Roche, it can not meet the needs of vitamin E. The 2,3,5-trimethyl hydroquinone of China is put into operation by only a few companies, China has become the world's second largest feed production country, if the amount of vitamin E in animal feed reach the average level of foreign words, the annual consumption vitamin E is nearly 2000t. According to Chinese feed industry planning, the amount of feed demand synthetic vitamin E is about 2500t in 2005. Furthermore, the needs of vitamin E in pharmaceutical, food, cosmetics and other needs for vitamin E will grow steadily in the future. So in the last ten years, or even 20 years, the future market 2,3,5-trimethyl hydroquinone can not be not saturated. The development of this project has broad application prospects.
Vitamin E is not only used as a medicine, feed, food, cosmetic additives, but also get more and more applications in industry, such as industrial antioxidants, polyolefin non-toxic, biodegradable stabilizer. A sharp increase in domestic and international market demand for vitamin E is present. The naturally occurring vitamin E is very limited, so timely start-up and expansion of production of vitamin E will bring better economic benefits.
The above information is edited by the chemicalbook of Wang Xiaodong.

Chemical Properties

It is crystalline solid. When heated, it can sublimate, when esposed to moisture, it can turn black easily. It can be slightly soluble in water, soluble in ethyl alcohol, insoluble in petroleum ether. Melting point is 173℃.

Uses

The product is main ring of vitamin E, it can condensation with isophytol to get vitamin E.
Organic intermediates, pharmaceutical intermediates, it can be used for the synthesis of VE.

Production method

By sulfonation, nitration, reduction, oxidation 1,2,4-trimethylbenzene can get 2,3,5-trimethyl benzoquionone ([935-92-2]). 2,3,5-trimethyl benzoquionone is yellow needle crystallization, melting point is 32℃ (38-29.5℃), the boiling point is 53℃(53Pa). Said step of products are generally to obtain a solution of petroleum ether or gasoline. In 2,3,5-trimethyl gasoline solution (petroleum ether), hydrosulfite solution is added with stirring, stir at room temperature for 3h, then filter, the cake should be washed with 0.5% hydrosulfite solution, and then dry to get trimethyl hydroquinone.

Chemical Properties

off-white, tan or orange powder

Uses

Trimethylhydroquinone is used for synthesizing vitamin E and used as medical intermediate.

Uses

Trimethylhydroquinone is a key precursor for the synthesis of tocopherols (vitamin E) and (±)-madindolines.

Definition

ChEBI: 2,3,5-trimethylhydroquinone is a member of the class of hydroquinones that is hydroquinone substituted by methyl groups at positions 2, 3 and 5. It is a member of hydroquinones and a methylbenzene.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 16, p. 378, 1968 DOI: 10.1248/cpb.16.378

Safety Profile

Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Recrystallise the hydroquinone from water, under anaerobic conditions. [Beilstein 6 H 931, 6 IV 5997.]