Synthesis of succinic acid

Preparation of succinic acid (butanedioic acid; 1,2-ethanedicarboxylic acid; amber acid; 1,4-butanedioic acid)

Preparation of succinic acid by reduction of maleic acid

The succinic acid could be prepared by reduction of maleic acid at high pressure. The carboxyl group is unaffected in the hydrogenations reaction if the alkali salt of the unsaturated acid is used.

Preparation of succinic acid by reduction of maleic acid

Preparation of succinic acid by reduction of maleic acid

In an autoclave of 325 ml capacity, 58 g of maleic acid, dissolved in 100 ml of water containing 5 g of sodium hydroxide more than needed for neutralization, were treated with 5-8 g of Raney nickel (prepared according W. Covert and H. Adkins, J . Amer. Chem. Soc, 54, 4116, 1932). Hydrogen was added to a pressure of 170 atm and heating then commenced. The pressure at first rose, but it decreased as reaction began at 100° C. This temperature of 100° C was maintained until the end of the reaction; after 26 min there was no further fall in pressure. After removal of the Raney nickel catalyst (pyrophoric!!!), the mixture was acidified and the water removed in a vacuum. The succinic acid was extracted with absolute ethanol and the ethanol was then evaporated. After recrystallization from water succinic acid melted at 184-185° C. The yield  57 g (or 98 %).

B. B. Allen, B. W. Wyatt, H. R. Henze, J . Amer. Chem. Soc, 61, 843 (1939).

Preparation of succinic acid from ethylene dibromide

Preparation of succinic acid from ethylene dibromide

Preparation of succinic acid from ethylene dibromide

100 g of ethylene dibromide and 75 g of potassium cyanide in alcoholic solution are refluxed on a water bath in a 1-liter round-bottomed flask until potassium bromide ceases to separate out from the solution. The latter is then cooled and filtered; 60 g of solid potassium hydroxide are added, and the mixture again refluxed on a water bath in a fume cupboard until the strong evolution of ammonia gas begins to slacken. The flask is then cooled, and the contents are acidified with dilute hydrochloric acid and carefully evaporated to dryness. The dry powdered residue is repeatedly extracted with absolute alcohol, and the extract distilled on a water bath. The succinic acid remains behind in small crystals; it is recrystallized from hot water, decolorising if necessary with a little animal charcoal. The yield of succinic acid  is 80% theoretical. Colorless prisms; soluble in water, alcohol, and ether; insoluble in chloroform; sublime above 100° C without decomposition; m.p. 185° C; at 235° C decompose forming the anhydride.

Systematic organic chemistry, by W. M. Cumming, 125-126, 1937.

Preparation of succinic acid from malic acid

Preparation of succinic acid from malic acid

Preparation of succinic acid from malic acid

10 g of malic acid are dissolved in 40 g of 57% (constant boiling mixture) hydriodic acid and the solution, together with 3 g of red phosphorus, heated in a sealed tube in a tube furnace at 130° C for 6 hours. When cool, the tube is opened, the contents evaporated to dryness on a water bath, and the cold residue extracted with small quantities of chloroform until no more free iodine is removed. The succinic acid is then heated at 70° C to remove all traces of chloroform, and recrystallised from hot water. Yield 60%. Colourless prisms; soluble in water, alcohol and ether; insoluble in chloroform; m.p. 182° C.

Systematic organic chemistry, by W. M. Cumming, 192, 1937.

IUPAC Name

butanedioic acid

InChI

InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

InChI Key

KDYFGRWQOYBRFD-UHFFFAOYSA-N

Canonical SMILES

C(CC(=O)O)C(=O)O

MeSH Synonyms

1,2 Ethanedicarboxylic Acid, 1,2-Ethanedicarboxylic Acid, 1,4 Butanedioic Acid, 1,4-Butanedioic Acid, Ammonium Succinate, Butanedioic Acid, Potassium Succinate, Succinate, Succinate, Ammonium, Succinate, Potassium, Succinic Acid

Depositor-Supplied Synonyms

succinic acid, butanedioic acid, Asuccin, Amber acid, Katasuccin, 110-15-6, Bernsteinsaure, Dihydrofumaric acid, Wormwood acid, succinate, 1,2-Ethanedicarboxylic acid, 1,4-Butanedioic acid, Wormwood, ethylenesuccinic acid, Butanedionic acid, Butandisaeure, Spirit of amber, Acidum succinicum, Kyselina jantarova, Ethylene dicarboxylic acid, Succinellite, Sal succini, Acid of amber, Succinicum acidum, Bernsteinsaure [German], Kyselina jantarova [Czech], Ethanedicarboxylic acid, Ethylene succinic acid, succ, Bernsteinsaeure, HSDB 791, acide succinique, Potassium Succinate, UNII-AB6MNQ6J6L, Succinicun acidum, 1cze, succinate, 9, acide butanedioique, NSC 106449, CHEBI:15741, AI3-06297, Succinic acid (8CI), NSC25949, AC1L1AQW, Butanedioic acid (9CI), EINECS 203-740-4, SBB040562, WLN: QV2VQ, SUCCINIC ACID, ACS, bmse000183, CHEMBL576, HOOC-CH2-CH2-COOH, BRN 1754069, NCGC00159372-02, E363, S9512_SIGMA, W502707_ALDRICH, W502715_ALDRICH, AC1Q757B, C4H6O4, S3674_SIAL, S7501_SIAL, Butanedioic acid diammonium salt, 14078_FLUKA, 14079_FLUKA, KDYFGRWQOYBRFD-UHFFFAOYSA-N, 14079_SIAL, 398055_SIAL, Amber acid, Butanedioic acid, Ethylenesuccinic acid, LMFA01170043, NSC106449, STK387105, AKOS000118899, DB00139, NCGC00159372-03, NCGC00159372-04, ethylenedicarboxylic acid, LS-147378, S0100, DSSTox_CID_3602, 1,4-BUTANEDIOIC ACID (SUCCINIC ACID), C00042, DSSTox_RID_77102, A 12084, DSSTox_GSID_23602, 4-02-00-01908 (Beilstein Handbook Reference), SIN, I04-1083, 37E8FFFB-70DA-4399-B724-476BD8715EF0, InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8, 623158-99-6, 6283-68-7, CAS-110-15-6, butanedioicacid, Dihydrofumarate, Butane diacid, Salt of amber, CID1110, 1,4-Butanedioate, Succinic acid, 6, nchembio856-comp9, Succinic acid [NF], 4lh2, nchembio.186-comp50, nchembio.198-comp17, nchembio.266-comp26, 1,2-Ethanedicarboxylate, Substrate analogue, 11, AB6MNQ6J6L, bmse000968, nchembio.2007.47-comp2, ethane-1,2-dicarboxylic acid, KSC175Q2B, ACMC-20995h, GTPL3637, BDBM26121, CTK0H5820, HMDB00254, MolPort-000-871-623, Tox21_111612, Tox21_201918, Tox21_303247, ANW-16131, BBL002473, DAP000545, NSC-25949, Tox21_111612_1, LS40373, MCULE-5889111640, NSC-106449, RP19292, RTR-002122, TRA0035567, NCGC00159372-05, NCGC00257092-01, NCGC00259467-01, 4CN-0813, AJ-24134, AK111253, AN-22587, BP-21128, I847, KB-60642, SC-47173, 98-EP2269610A2, 98-EP2269983A1, 98-EP2269984A1, 98-EP2269986A1, 98-EP2269988A2, 98-EP2269989A1, 98-EP2269990A1, 98-EP2270002A1, 98-EP2270003A1, 98-EP2270006A1, 98-EP2270008A1, 98-EP2270011A1, 98-EP2270505A1, 98-EP2272516A2, 98-EP2272537A2, 98-EP2272827A1, 98-EP2275401A1, 98-EP2275411A2, 98-EP2275412A1, 98-EP2275413A1, 98-EP2275414A1, 98-EP2277507A1, 98-EP2277848A1, 98-EP2277858A1, 98-EP2277866A1, 98-EP2277867A2, 98-EP2280003A2, 98-EP2280006A1, 98-EP2280010A2, 98-EP2281559A1, 98-EP2281563A1, 98-EP2281819A1, 98-EP2284146A2, 98-EP2284147A2, 98-EP2284149A1, 98-EP2284160A1, 98-EP2284165A1, 98-EP2284169A1, 98-EP2284178A2, 98-EP2284179A2, 98-EP2286795A1, 98-EP2287153A1, 98-EP2287155A1, 98-EP2287156A1, 98-EP2287160A1, 98-EP2287161A1, 98-EP2287162A1, 98-EP2289510A1, 98-EP2289518A1, 98-EP2289876A1, 98-EP2289879A1, 98-EP2289883A1, 98-EP2289890A1, 98-EP2292227A2, 98-EP2292231A1, 98-EP2292234A1, 98-EP2292592A1, 98-EP2292611A1, 98-EP2292617A1, 98-EP2292619A1, 98-EP2295401A2, 98-EP2295402A2, 98-EP2295406A1, 98-EP2295416A2, 98-EP2295424A1, 98-EP2295426A1, 98-EP2295427A1, 98-EP2295433A2, 98-EP2295437A1, 98-EP2298731A1, 98-EP2298734A2, 98-EP2298735A1, 98-EP2298742A1, 98-EP2298746A1, 98-EP2298747A1, 98-EP2298748A2, 98-EP2298757A2, 98-EP2298758A1, 98-EP2298759A1, 98-EP2298768A1, 98-EP2298772A1, 98-EP2298775A1, 98-EP2301544A1, 98-EP2301922A1, 98-EP2301924A1, 98-EP2301931A1, 98-EP2301937A1, 98-EP2301940A1, 98-EP2305219A1, 98-EP2305248A1, 98-EP2305257A1, 98-EP2305633A1, 98-EP2305636A1, 98-EP2305641A1, 98-EP2305646A1, 98-EP2305651A1, 98-EP2305653A1, 98-EP2305655A2, 98-EP2305657A2, 98-EP2305659A1, 98-EP2305663A1, 98-EP2305664A1, 98-EP2305673A1, 98-EP2305675A1, 98-EP2305676A1, 98-EP2305679A1, 98-EP2308839A1, 98-EP2308849A1, 98-EP2308850A1, 98-EP2308851A1, 98-EP2308854A1, 98-EP2308857A1, 98-EP2308861A1, 98-EP2308869A1, 98-EP2308872A1, 98-EP2308873A1, 98-EP2308875A1, 98-EP2311807A1, 98-EP2311808A1, 98-EP2311809A1, 98-EP2311810A1, 98-EP2311811A1, 98-EP2311814A1, 98-EP2311818A1, 98-EP2311829A1, 98-EP2311831A1, 98-EP2311834A1, 98-EP2311837A1, 98-EP2311842A2, 98-EP2314295A1, 98-EP2314574A1, 98-EP2314575A1, 98-EP2314576A1, 98-EP2314581A1, 98-EP2314585A1, 98-EP2314586A1, 98-EP2314588A1, 98-EP2314593A1, 98-EP2316457A1, 98-EP2316458A1, 98-EP2316459A1, 98-EP2316825A1, 98-EP2316826A1, 98-EP2316827A1, 98-EP2316828A1, 98-EP2316829A1, 98-EP2316831A1, 98-EP2316834A1, 98-EP2316835A1, 98-EP2316836A1, 98-EP2371797A1, 98-EP2371798A1, 98-EP2371800A1, 98-EP2371802A1, 98-EP2371804A1, 98-EP2371805A1, 98-EP2372017A1, 98-EP2374454A1, 98-EP2374780A1, 98-EP2374781A1, 98-EP2380874A2, TR-002122, FT-0652509, N1941, ST24031670, ST50213944, T7308, 47632-EP2281817A1, 47632-EP2311811A1, AB01332192-02, 196539-EP2270007A1

Removed Synonyms

Ammonium succinate, fumaric acid, maleic acid, Dicarboxylic acid, DL-malic acid, Guna-allergy-prev, Succinate, Ammonium, Succinate, Potassium, 1,4 Butanedioic Acid, 1,2 Ethanedicarboxylic Acid, D019802, 109-59-1, 60719-85-9, fum, MAE, suc

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *