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Synthesis of MTHPA (MHHPA) from maleic anhydride and pentadiene

Brief introduction
 
Hydro-phthalic anhydrides -- tetra-hydrophthalic anhydride, hexa-hydrophthalic anhydride, methyl tetrahydrophthalic anhydride (MTHPA), and methyl hexahydrophthalic anhydride (MHHPA) -- are used by the electronic information industry and are important intermediates for the pharmaceutical, pesticide, resin, and national defense industries. They have low toxicity and low volatility and are mainly used for curing agents of epoxy resin.
 
Process

The synthesis of MTHPA from maleic anhydride and pentadiene is a typical Diels-Alder condensation reaction, i.e. the unsaturated maleic anhydride with olefinic bonds is a dienophile. It takes a 1,4 addition reaction with pentadiene, a catenary diene with conjugated diene, to generate a cyclohexene ring - hydroaromatic compound. The production flow goes as followings: with polymerization inhibitors, maleic anhydride reacts with pentadiene to generate MTHPA; after a preliminary separation of MTHPA, isomerization catalyst is added to continue the reaction to generate liquid MTHPA; after rectification, the colorless, transparent liquid MTHPA presults. MHHPA is the product of the hydrogenation of MTHPAT and follows a similar process.

Product quality

Quality indicators of MTHPA

Item

Indicator

Appearance

Colorless, transparent liquid

Chroma (Pt-Co scale)

<200

Specific gravity (25℃)

1.21±0.04

Viscosity cp (25℃)

50~70

Melting point ℃

≤-15

Acid value mgKOH/g

660~670

Anhydride content %

≥41

Heating loss %

<1

Free acid %

<1

Quality indicators of MHHPA

Item

Indicator

Appearance

Colorless, transparent liquid

Specific gravity (25℃)

1.16±0.04

Viscosity cp (25℃)

50~60

Melting point ℃

≤-15

Acid value mgKOH/g

≥660

Iodine value

<2

HHPA content %

≥99%

Free acid %

≤0.5

 

Technical indicators

Item

Specification

Unit

Consumption quota

Maleic anhydride

Industrial grade

t

0.7

C5 fraction

Industrial grade

t

0.5

Catalyst

Industrial grade

kg

4

Cooling water

t

50

Electricity

220V/380V

kWh

800

Steam

0.8MPa

t

2.5

Waste treatment

The process is highly selective with few byproducts. Only a small amount of organic liquid waste is discharged from the rectification tower and it can be incinerated.

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