1,2,3,6-Tetrahydrophthalic anhydride Chemical Properties

Melting point:

101-102°C

Boiling point:

195°C 5mm

Density 

1,375 g/cm³

vapor pressure 

0.021Pa at 20℃

refractive index 

1.4810 (estimate)

Flash point:

157°C

storage temp. 

Store below +30°C.

solubility 

soluble in DCM, Ethyl Acetate, Toluene

form 

Solid

pka

3.84[at 20 ℃]

color 

Off-White to Light Tan

PH

2.1 (20°C, 10g/L in H2O)

Water Solubility 

29.4g/L at 20℃

LogP

1.29 at 40℃

CAS DataBase Reference

85-43-8(CAS DataBase Reference)

EPA Substance Registry System

Tetrahydrophthalic anhydride (85-43-8)

Safety Information

Risk Statements 

41-42/43-52/53

Safety Statements 

26-36/37/39

RIDADR 

2698

Autoignition Temperature

400°C

HazardClass 

8

PackingGroup 

III

Hazardous Substances Data

85-43-8(Hazardous Substances Data)

1,2,3,6-Tetrahydrophthalic anhydride Usage And Synthesis

Chemical Properties

white flaky solid

Uses

Chemical intermediate for light-colored alkyds, polyesters, plasticizers, and adhesives; intermediate for pesticides; hardener for resins.

Definition

ChEBI: 1,2,3,6-tetrahydrophthalic anhydride is a cyclic dicarboxylic anhydride that is 1,3,3a,4,7,7a-hexahydro-2-benzofuran carrying oxo groups at positions 1 and 3. It is a cyclic dicarboxylic anhydride and a tetrahydrofurandione.

General Description

Clear colorless to light yellow slight viscous liquid. Highly toxic and a strong irritant to skin, eyes and mucous membranes. Corrosive to skin and metal. Used in making polyester, alkyd resins, and plasticizers.

Air & Water Reactions

Reacts exothermically with water to form memtetrahydrophthalic acid.

Reactivity Profile

CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE; >98% is combustible. Reacts with oxidizers. Reacts exothermically with water. These reactions are usually slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.

Hazard

Strong irritant to eyes and skin.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Flammability and Explosibility

Non flammable

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. A corrosive irritant to skin, eyes, and mucous membranes. Combustible when exposed to heat or flame. Will react with water or steam to produce heat; can react with oxidizing materials. To fight fre, use water, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.

Synthesis

2.0 g of lanthanum nitrate hexahydrate was dissolved in 100 mL of deionized water, and the resulting solution was added dropwise to a suspension formed from 5.0 g of H-type Y-zeolite (Tosoh Corporation, HSZ-320H0A, Si/Al ratio = 2.8) with 200 mL of deionized water at room temperature. Subsequently, the mixture was heated at 90 °C for 3 hours. Upon completion of the reaction, the solid product was separated by centrifugation, washed five times with 45 mL of deionized water, and dried at 85 °C overnight. The dried solid was calcined in an air atmosphere at 500 °C for 2 h to obtain the alkylation catalyst (hereinafter referred to as La/HY). The content of La in the catalyst was determined to be 5.6 wt% by ICP analysis. The alkylation reaction was carried out in a SUS autoclave equipped with a 50 mL glass liner. To the glass liner were added 0.10 g of the above La/HY catalyst (100 wt% relative to the unsaturated compounds), 0.16 g of tridecane (internal standard), 0.1 g (0.53 mmol) of methyl 1-cyclohexene-4,5-dicarboxylate (hereinafter referred to as CEDA) as the unsaturated compounds, and 3.0 g (28.30 mmol) of o-xylene as the aromatic compound. The system was sealed under nitrogen atmosphere after three displacements with nitrogen. The reaction was initiated by immersing the autoclave in an oil bath preheated to 180 °C. The reaction was carried out in a water bath. After 2 hours of reaction, the reactor was cooled with water to release the internal gases. The alkylation products 3,4-dimethoxycarbonylcyclohexyl-3',4'-dimethylbenzene (hereinafter referred to as CDMB) and 1-cyclohexene-4,5-dicarboxylic anhydride, etc., in the reaction solution were quantitatively analyzed by gas chromatography with an FID detector as an internal standard method. The results showed that the yield of CDMB was 49.6% and the selectivity was 51.0%.CDMB is a new compound with the following physical properties: boiling point: 166 °C/66 Pa; 1H NMR (500 MHz, CDCl3): δ 1.44-1.48 (m, 1H), 1.69-1.76 (m, 1H), 1.95-2.04 (m, 2H), 2.13-2.16 (m, 1H), 2.22 (s, 3H), 2.24 (s, 3H), 2.33-2.38 (m, 1H), 2.48-2.56 (m, 2H), 3.37-3.96 (m, 1H), 3.71 (s, 3H*2), 6.92 (d, J=7.7 Hz, 1H), 6.96 (s, 1H), 7.06 (d, J=7.7 Hz, 1H) 7.06 (d, J=7.7 Hz, 1H); 13C NMR (500 MHz, CDCl3): δ 19.3, 19.8, 24.5, 33.2, 35.5, 39.0, 42.0, 43.3, 51.8, 123.9, 128.2, 129.7, 134.4, 136.5, 143.4, 173.8, 174.2; IR (d, J=7.7 Hz, 1H). 174.2; IR (neat, cm-1): 3450, 3000, 2950, 2860, 1734.

References

[1] Patent: US2013/41174, 2013, A1. Location in patent: Paragraph 0051; 0072

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