Dimethyl itaconate

Boiling point

Description of key information

Experimental data under vacuum and ambient pressure, no decomposition

Key value for chemical safety assessment

Boiling point at 101 325 Pa:

208 °C

Additional information

After his first publication from 1881 reporting the first synthesis of the submission item, Anschütz (1905) describes the production of a highly pure grade. In both publications slightly different boiling points at ambient pressure are reported, but the later one is considered more reliable as a better purity was achieved. At the time of the publication no guideline existed. During the investigation of its boiling behaviour the material was visually inspected. The temperature was measured and recorded. The chemical identity was verified by burning with subsequent elemental analysis, whereas the molecular weight was confirmed by measuring effects on melting point decrease / boiling point increase of solutions and finally by determination of the vapour density. The observations are reported in great detail. However an old publication, the experiments are deemed valid, conclusive and thus suitable for assessment (reliable with restrictions, Klimisch score 2). The value of Anschütz (1905) was confirmed by further literature and company data and used for handbooks and collection of data including the U.S. EPA EPI Suite software MPBPVP v1.43, September 2008, training set. The data are considered relevant and taken together adequate for the assessment of the boiling point.

The test item was slowly heated and was visually observed. No signs of decomposition were present until boiling. Under ambient pressure conditions (780 mm Hg) the substance boiled at 208 °C, while in vacuum (11 mm Hg) the boiling point was reduced to 108 °C.

• Anschütz R (1881). 505. Beiträge zur Kenntnis der Itaconsäure, Citraconsäure und Mesaconsäure. ISSN 1099-0682 CODEN CHBEA Berichte der Deutschen Chemischen Gesellschaft (Berlin, since 1947 renamed in Chemische Berichte) 14:2784 -9. http://gallica.bnf.fr/ark:/12148/bpt6k906939/f1193.image.langDE
• Anschütz R (1905). 107. Ueber den einfachen Itaconsäuremethylester. ISSN 1099-0682 CODEN CHBEA Berichte der Deutschen Chemischen Gesellschaft (Berlin, since 1947 renamed in Chemische Berichte) 38:691-3.

Further data on boiling under vacuum (1.3, 10, 11, 13, 15, 20 and 22 mm Hg) exist in the literature:

Table: Overview of Boiling points at several pressure conditions (supplementary data)

Boiling Point [°C]	Pressure [Torr = mm Hg]	Literature Reference no.
56 - 58	1.3	3
108 - 109	10	5
93 - 95		10
108	11	1, 2
111	13	9
95 - 100	15	4
102 - 103	20	6
105	22	8
110 - 112	not specified	7

The value (208 °C) of Anschütz (1905) was confirmed in practical use, by company data and was used for handbooks / collection of data including the U.S. EPA EPI Suite software MPBPVP v1.43, September 2008, training set.

In conclusion the submission item has a boiling point of 208 °C and does not decompose during boiling.

References:

1. Anschütz R (1905). 107. Ueber den einfachen Itaconsäuremethylester. ISSN 1099-0682 CODEN CHBEA Berichte der Deutschen Chemischen Gesellschaft (Berlin, since 1947 renamed in Chemische Berichte) 38:691-3.
2. Borisow et al. (1974). Izv.Otd.Khim.Nauki (Bulg.Akad.Nauk.) 25:26-8.
3. Kloetzel MC (1948). Reactions of Nitroparaffins. II Addition of Nitroparaffins to Unsaturated Esters. DOI 10.1021/ja01191a009 J Amer Chem Soc 70(11):3571-6, on page 3573.
4. Nogi & Tsuji (1969). Tetrahedron 25(17):4099,4107.
5. Askarov, Tadzhieva (1967 & 1969). Miner Struktur Gerbits 261:262-4 & Chem Abstr 71(71031).
6. Nagui El Ghandour, Soulier (1971). Bull Soc Chim Fr 2290:2291.
7. Kamal et al. (1971). Pak J Sci Ind Res 14:86,88.
8. Sakai (1977). Bull Chem Soc Jpn 50:1232.
9. Sakai et al. (1978). Bull Chem Soc Jpn 51:2970.
10. Gusev BP, El'perina EA, Kucherov VF, Pirozhkov SD, Lapidus AL (1980). Bull Acad Sci USSR Div Chem Sci (English Translation) 29(3):421-5 & Izv Akad Nauk SSSR Ser Khim 3:603-7.