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2170-03-8

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2170-03-8 Usage

Chemical Properties

WHITE TO CREAM CRYSTALLINE POWDER

Uses

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

Preparation

To a flask equipped with a 12 mm diameter ground glass adaptor tube bent for downward distillation and joined to a 100 cm condenser is added 200 gm (0.95 mole) of citric acid monohydrate. An ice-cooled flask and a cold trap are connected to the condenser. The flask containing the citric acid is heated rapidly with a wide flame of the Meker burner so that in 12-15 min the distillation at 175-190°C is complete. The distillation is stopped earlier if the vapors in the reaction flask become yellow. Superheating of the citric acid will cause rearrangement to citraconic anhydride. The water is quickly separated from the distillate and the itaconic anhydride layer dried to afford 40-50 gm (37-47%), m.p. 67-68°C. Long time contact of the water with the anhydride causes it to hydrolyze to itaconic acid, m.p. 162-165°C.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 6027, 1984 DOI: 10.1016/S0040-4039(01)81751-2

General Description

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.

Purification Methods

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 2170-03-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,7 and 0 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2170-03:
(6*2)+(5*1)+(4*7)+(3*0)+(2*0)+(1*3)=48
48 % 10 = 8
So 2170-03-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O7/c1-5(3-7(11)12)9(15)17-10(16)6(2)4-8(13)14/h1-4H2,(H,11,12)(H,13,14)

2170-03-8 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (B25216)  Itaconic anhydride, 97%   

  • 2170-03-8

  • 25g

  • 336.0CNY

  • Detail
  • Alfa Aesar

  • (B25216)  Itaconic anhydride, 97%   

  • 2170-03-8

  • 100g

  • 1099.0CNY

  • Detail
  • Alfa Aesar

  • (B25216)  Itaconic anhydride, 97%   

  • 2170-03-8

  • 500g

  • 4955.0CNY

  • Detail
  • Aldrich

  • (259926)  Itaconicanhydride  95%

  • 2170-03-8

  • 259926-25G

  • 422.37CNY

  • Detail
  • Aldrich

  • (259926)  Itaconicanhydride  95%

  • 2170-03-8

  • 259926-100G

  • 1,207.44CNY

  • Detail

2170-03-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-methylideneoxolane-2,5-dione

1.2 Other means of identification

Product number -
Other names 3,4-dihydro-3-methylidenefuran-2,5-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2170-03-8 SDS

2170-03-8Relevant articles and documents

Four component Passerini polymerization of bulky monomers under high shear flow

Barner-Kowollik, Christopher,Bui, Aaron H.,Raston, Colin L.,Truong, Vinh X.,Tuten, Bryan T.,Wiedbrauk, Sandra

, p. 8328 - 8331 (2021)

We introduce a four component Passerini polymerization utilizing sterically bulky isocyanide monomers. Under typical Passerini conditions, bulky isocyanides do not react within standard Passerini reaction timescales (hours). We overcome this challenge via the unique physiochemical conditions present in a vortex fluidic device, reducing the reaction time to 2 h on average. Under these high-shear thin-film conditions, bulky isocyanides are readily incorporated into the multicomponent polymerization without the need of high-pressure or temperature. Finally, we demonstrate that the four component approach using functional cyclic anhydrides allows for post-polymerization modification.

NMR Investigation of the Thermolysis of Citric Acid

Fischer, John W.,Merwin, Lawrence H.,Nissan, Robin A.

, p. 120 - 126 (1995)

The thermolytic decomposition of citric acid in the presence of tin/lead solder has been investigated.The solid reaction products were first examined by solid-state 13C NMR.The samples were then dissolved in D2O, and 1H and 13C 1D and 2D (HMQC, TOCSY) spectra were obtained.Results indicate the presence of a series of compounds including 3-hydroxyglutaric, citraconic, itaconic and aconitic acids, and anhydrides.Solution- and solid-state NMR data are provided for citric acid and a number of metal and alkali metal citrate salts.Results of this work are related to the use of citric acid as a solder flux and to the elimination of chlorofluorocarbon cleaning processes in the electronics industry.Index Headings: NMR; Solid-state NMR; Citric acid; Thermolysis.

New type of prototropic tautomerism involving carbon, hydrogen, and oxygen atoms

Filimoshkin,Kosolapova,Petrenko,Aksenov,Poleshchuk

, p. 462 - 466 (2004)

A low-molecular weight analog of the vinyl chloride-maleic anhydride copolymer, chloromethylsuccinic anhydride gives rise to a new type of prototropic tautomerism, cyclic anhydride-enol, with formation of quasiaromatic enol and dienol derivatives. The ratio of the anhydride and enol tautomers in solution at room temperature is 7:1.

FRAGRANCE MIXTURE

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Paragraph 0317-0319, (2020/01/24)

A fragrance mixture and its applications, in particular perfume oils, cosmetic agents, application agents or washing and cleaning agents, containing a sensory effective amount of (i) (E)-2-methyl-but-2-endicarboxylic acid diethyl ester, (ii) (Z)-2-methyl-but-2-endicarboxylic acid diethyl ester or (iii) 2-methylenebutanedicarboxylic acid diethyl ester and mixtures thereof and analogous esters derived from these compounds and mixtures.

(Re)Investigation of the reactivity of uranium hexafluoride toward several organic functions at room temperature

Roy, Olivier,Marquet, Bernard,Alric, Jean-Paul,Jourdan, Alex,Morel, Bertrand,Langlois, Bernard R.,Billard, Thierry

, p. 74 - 78 (2015/03/04)

The annual worldwide production of UF6 is very large and this compound is not used. Consequently, it could be interesting to find some applications as organic reagent. UF6 could be considered as an oxidizer of various functions. However, it seems also present some possibilities as a fluorinating reagent in mild conditions.

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