Synthesis of succinic anhydride

Preparation succinic anhydride

Preparation of succinic anhydride (dihydrofuran-2,5-dione; oxolane-2,5-dione)

Preparation of succinic anhydride (dihydrofuran-2,5-dione; oxolane-2,5-dione)

In a 100 ml round-bottomed flask fitted with a reflux condenser closed with a calcium chloride tube 15 grams of succinic acid and 25 ml of acetic anhydride are placed. Instead of acetic anhydride 30 ml of acetyl chloride could be used. The mixture gently heated with occasional shaking until a clear solution is obtained and then for one half hour longer to insure completion of the reaction. The flask is cooled to room temperature and then in an ice bath, the obtained crystals are collected by filtration,  washed with small amount of ether. The yield is 10-11 grams with melting point 120° C.

Experiments in Organic Chemistry, L. F. Fieser, 104, 1941

Preparation of succinic anhydride

Preparation of succinic anhydride

10 g of finely powdered succinic acid are refluxed for 3 hours with 20 g of acetyl chloride and allowed to stand in a soda-lime desiccator until acetyl chloride and acetic acid are completely removed. The residue is recrystallised from absolute alcohol. Yield almost theoretical. Long needles; m.p. 119.6° C; b.p. 131° C/10mm; b.p. 261° C/760 mm.

Systematic organic chemistry, by W. M. Cumming, 266, 1937.

IUPAC Name

oxolane-2,5-dione

InChI

InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2

InChI Key

RINCXYDBBGOEEQ-UHFFFAOYSA-N

Canonical SMILES

C1CC(=O)OC1=O

MeSH Synonyms

succinic anhydride

Depositor-Supplied Synonyms

SUCCINIC ANHYDRIDE, 108-30-5, dihydrofuran-2,5-dione, Dihydro-2,5-furandione, Succinyl oxide, 2,5-Diketotetrahydrofuran, Succinic acid anhydride, oxolane-2,5-dione, Succinyl anhydride, 2,5-Furandione, dihydro-, Butanedioic anhydride, Tetrahydro-2,5-dioxofuran, Rikacid SA, 2,5-Dioxotetrahydrofuran, Tetrahydro-2,5-furandione, Bernsteinsaure-anhydrid, NCI-C55696, NSC 8518, Dihydro-furan-2,5-dione, tetrahydrofuran-2,5-dione, UNII-6RF4O17Z8J, CCRIS 2386, HSDB 792, Bernsteinsaure-anhydrid [German], CHEBI:36595, Dihydro-2,5-diketotetrahydrofuran, RINCXYDBBGOEEQ-UHFFFAOYSA-N, EINECS 203-570-0, SBB040819, BRN 0108441, AI3-52664, 3,4-dihydrofuran-2,5-dione, Succinyloxide, 2, dihydro-, Bernsteinsaeureanhydrid, PubChem21337, ACMC-1BZUC, WLN: T5VOVTJ, DSSTox_CID_1287, AC1L1PV0, AC1Q6EJ8, tetrahydro-furan-2,5-dione, DSSTox_RID_76059, DSSTox_GSID_21287, SCHEMBL16123, 2,5(3H,4H)-Furandione, KSC492A9N, MLS002454448, Succinic anhydride treated BSA, 239690_ALDRICH, 6RF4O17Z8J, CHEMBL1370164, CTK3J2096, NSC8518, MolPort-000-871-978, HMS3039B10, NSC-8518, STR01303, EINECS 270-161-1, Tox21_201179, ANW-15922, LS-457, AKOS000121191, MCULE-1458819618, NE10403, RP09600, RTR-001926, TRA0038939, NCGC00091291-01, NCGC00091291-02, NCGC00258731-01, AK139125, AN-22506, BC676904, BP-13070, CAS-108-30-5, SC-16393, SMR001372026, AB1002026, DB-050501, KB-145694, ST2412820, TR-001926, FT-0652573, S0107, ST50214397, Dihydro-2,5-furandione; Butanedioic anhydride, 2-Alkenyl (C11-C13) succinic acid anhydride, C19524, Succinic anhydride treated bovine serum albumin, 40410-EP2270015A1, 40410-EP2289893A1, 40410-EP2292593A2, 40410-EP2305808A1, 40410-EP2311830A1, 40410-EP2371805A1, 5-17-11-00006 (Beilstein Handbook Reference), A801840, 3B4-0899, S04-0168, T6075840, BUTANEDIOIC ACID,ANHYDRIDE SUCCINIC ANHYDRIDE, 2,5-Furandione, dihydro-, mono-C11-13-alkenyl derivs., 3B3-024387, InChI=1/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H, 1123596-58-6, 68412-02-2

Removed Synonyms

Succinyl peroxide, CID7922, DTHKSEIAHRFKDLGEEQFKGLVLIAFSQYLQQCPFDEHVKLVNELTEFAKTCVADESHAGCEKSLHTLFGDELCKVASLRETYGDMADCCEKQEPERNECFLSHKDDSPDLPKLKPDPNTLCDEFKADEKKFWGKYLYEIARRHPYFYAPELLYYANKYNGVFQDCCQAEDKGACLLPKIETMREKVLASSARQRLRCASIQKFGERALKAWSVARLSQKFPKAEFVEVTKLVTDLTKVHKECCHGDLLECADDRADLAKYICDNQDTISSKLKECCDKPLLEKSHCIAEVEKDAIPENLPPLTADFAEDKDVCKNYQEAKDAFLGSFLYEYSRRHPEYAVSVLLRLAKEYEATLEECCAKDDPHACYSTVFDKLKHLVDEPQNLIKQNCDQFEKLGEYGFQNALIVRYTRKVPQVSTPTLVEVSRSLGKVGTRCCTKPESERMPCTEDYLSLILNRLCVLHEKTPVSEKVTKCCTESLVNRRPCFSALTPDETYVPKAFDEKLFTFHADICTLPDTEKQIKKQTALVELLKHKPKATEEQLKTVMENFVAFVDKCCAADDKEACFAVEGPKLVVSTQTALA, SAA

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2 comments

  1. Qalbe Hassan

    Hi!
    I’m just looking for diagram of procedure for prepation of succinic anhydride from succinic acid.
    Please help me??

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