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Itaconic anhydride

Itaconic anhydride structure

CAS No:
2170-03-8
Formula:
C5H4O3
Chemical Name:
Itaconic anhydride
Synonyms:
2-Methylenebutanedioic anhydride;Methylenesuccinic acid anhydride;3,4-Dihydro-3-methylene-2,5-furandione Methylenesuccinic Anhydride;Itaconic anhydride(2-Methylenesuccinic anhydride);Itaconic anhydride 95%;Itaconic anhydride,98%;ITACONIC ANHYDIDE;ITACONIC ANHYDRIDE
Categories:
Chemical Reagents > Organic Reagents

Description

WHITE TO CREAM CRYSTALLINE POWDER

Itaconic anhydride (ITA) is a biobased material that is obtained from renewable resources. It is produced from the pyrolysis of citric acid or by fermenting carbohydrates which forms itanoic acid. Itanoic acid can be dehydrated to form an anhydride. It is relatively more reactive that maleic anhydride and can be used as an alternating monomer that facilitates the introduction of polar functionalities in polymers.

Crystallise the anhydride from CHCl3/pet ether. It can be distilled under reduced pressure. Distillation at atmospheric pressure, or prolonged distillation causes rearrangement to citraconic anhydride (2-methylmaleic anhydride). If the material (as seen in the IR spectrum) contains much free acid, then heat with acetyl chloride or SOCl2, evaporate and distil at as high a vacuum as possible. The crude anhydride deposits crystals of itaconic acid on standing probably due to hydrolysis by H2O — store it in sealed ampoules under dry N2. [Skinner et al. Org Synth Coll Vol II 368 1943, IR: Nagai Bull Chem Soc Jpn 37 369 1964, Kelly & Segura J Am Chem Soc 56 2497 1934, Beilstein 17/11 V 66.]

Itaconic anhydride Basic Attributes

Molecular Weight：

112.08

Exact Mass：

112.08

BRN：

2212

EC Number：

218-518-2

UNII：

Y455KS1U7Q

NSC Number：

43979|43972

TSCA：

TSCA listed

DSSTox ID：

DTXSID8062230

Color/Form：

White to cream

HScode：

2917 19 80

Characteristics

PSA：

43.4

XLogP3：

0.01610

Appearance：

White to cream Crystalline Powder

Density：

1.2600

Melting Point：

66-68 °C (lit.)

Boiling Point：

114-115 °C/12 mmHg (lit.)

Flash Point：

114-115°C/12mm

Refractive Index：

1.5130 (estimate)

Water Solubility：

Hydrolyzes in water.

Storage Conditions：

Store below +30°C.

Critical Temperature & Pressure：

Store below +30°C.

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

Xi,Xn

safety instructions：

26-36-24/25

Marks：

Xi,Xn

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

36/37/38-22

GHS Classification：

|Warning|H302 (85.11%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Itaconic anhydride Use and Manufacturing

Methods of Manufacturing

Heat 200g (0.95mol) of citric acid monohydrate to melt, and arrange for rapid distillation in a distillation device (to avoid overheating). The distillate contains water and itaconic anhydride. After layering, remove the lower layer to obtain 40-50g of product, with a yield of 37. -47%.

Uses

Widely used in metal adhesion promoters, synthetic resin improvers, esterifying agents, anti-tarnish agents, herbicides, insecticides, etc.

Itaconic anhydride is used in immobilization of β-glucosidase. It undergoes estrification to obtain suitable monomers for emulsion polymerization itaconates.

Manufacturing Info：

2,5-Furandione, dihydro-3-methylene-: ACTIVE

Computed Properties

Molecular Weight:112.08
XLogP3:0.2
Hydrogen Bond Acceptor Count:3
Exact Mass:112.016043985
Monoisotopic Mass:112.016043985
Topological Polar Surface Area:43.4
Heavy Atom Count:8
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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