PL99572B1 - METHOD OF MAKING THE SODIUM SALT OF ITACONIC ACID - Google Patents
METHOD OF MAKING THE SODIUM SALT OF ITACONIC ACID Download PDFInfo
- Publication number
- PL99572B1 PL99572B1 PL1974170923A PL17092374A PL99572B1 PL 99572 B1 PL99572 B1 PL 99572B1 PL 1974170923 A PL1974170923 A PL 1974170923A PL 17092374 A PL17092374 A PL 17092374A PL 99572 B1 PL99572 B1 PL 99572B1
- Authority
- PL
- Poland
- Prior art keywords
- itaconic acid
- making
- sodium salt
- sodium
- reactions
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 title description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 title description 2
- NOJNFULGOQGBKB-UHFFFAOYSA-M sodium;3-[3-tert-butylsulfanyl-1-[[4-(6-ethoxypyridin-3-yl)phenyl]methyl]-5-[(5-methylpyridin-2-yl)methoxy]indol-2-yl]-2,2-dimethylpropanoate Chemical compound [Na+].C1=NC(OCC)=CC=C1C(C=C1)=CC=C1CN1C2=CC=C(OCC=3N=CC(C)=CC=3)C=C2C(SC(C)(C)C)=C1CC(C)(C)C([O-])=O NOJNFULGOQGBKB-UHFFFAOYSA-M 0.000 title 1
- 238000000034 method Methods 0.000 claims description 10
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 claims description 3
- UMTVCEDYAZNYBU-UHFFFAOYSA-N 2-methylidenebutanedioic acid;sodium Chemical compound [Na].OC(=O)CC(=C)C(O)=O UMTVCEDYAZNYBU-UHFFFAOYSA-N 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarza¬ nia soli sodowej kwasu itakonowego.Znany jest sposób wytwarzania kwasu itakono¬ wego oraz jego pochodnych metoda fermentacyj¬ na, która jednak z przemyslowego punktu widze¬ nia jest niedogodna ze wzgledu na niska wydaj¬ nosc i znaczny koszt instalacji.Znane sa takze zastosowania pochodnych kwa¬ su itakowego, np. jako manomerów, które poli¬ meryzuje sie z innymi waznymi monomerami, ta¬ kimi jak akrylonitryl, styren, estry kwasu akry¬ lowego, a otrzymane polimery odznaczaja sie cha¬ rakterystycznymi wlasciwosciami (przyczepnosc barwnika).Sposób wedlug wynalazku zapewnia proste i ta¬ nie wytwarzanie soli sodowej kwasu itakowego z latwo dostepnych surowców. Sposób wedlug wy¬ nalazku polega na tym, ze poddaje sie reakcji trio- ksan z bursztynianem dwuetylowym. Reakcje te prowadzi sie w fazie cieklej w roztworze rozpusz¬ czalnika alkoholowego w obecnosci alkoholanu, takiego jak III rz. butanolan sodu w temperaturze i pod cisnieniem zdolnym do utrzymania fazy cie¬ klej.Nizej podany przyklad ilustruje przedmiot wy¬ nalazku.Przyklad. W autoklawie o pojemnosci 500 ml, wyposazonym w mieszadlo, umieszcza sie 63,3 ¦ g bursztynianiu dwuetylu i 10 g trioksanu, a na¬ stepnie w atmosferze azotu, dodaje sie roztwór III rz. butanolanu sodu w III. rz. butanolu, otrzy¬ many z 13 g sodu rozpuszczonego w 200 ml III. rz. butanolu. Mieszanine ogrzewa sie do temperatury 65—85°C i z roztworu na drodze hydrolizy wydzie¬ la sie sól sodowa kwasu itakowego z wydajnoscia 70%. PLThe subject of the invention is a method for the production of sodium itaconic acid. There is a known method for the production of itaconic acid and its derivatives by fermentation method, which, however, from an industrial point of view, is inconvenient due to the low efficiency and high cost of the installation. There are also known uses of itacic acid derivatives, e.g. as manomers which are polymerized with other important monomers, such as acrylonitrile, styrene, acrylic acid esters, and the polymers obtained have characteristic properties (adhesion The method of the invention provides for the simple and inexpensive preparation of sodium itacic acid from readily available raw materials. The process according to the invention consists in reacting trioxane with diethyl succinate. These reactions are carried out in the liquid phase in a solution of an alcoholic solvent in the presence of an alkoxide such as third order. Sodium butoxide at a temperature and pressure capable of maintaining the phase liquid adhesive. The following example illustrates the subject of the invention. In a 500 ml autoclave equipped with a stirrer, 63.3 g of diethyl succinate and 10 g of trioxane are placed, and then, under a nitrogen atmosphere, a third solution is added. sodium butoxide in III. noun butanol, obtained from 13 g of sodium dissolved in 200 ml of III. noun butanol. The mixture is heated to 65 ° -85 ° C. and the sodium salt of itacic acid is separated from the solution by hydrolysis in a yield of 70%. PL
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23862/73A IT987221B (en) | 1973-05-09 | 1973-05-09 | PROCESS FOR THE PREPARATION OF ITACONIC ACID AND ITS DERIVATIVES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL99572B1 true PL99572B1 (en) | 1978-07-31 |
Family
ID=11210488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974170923A PL99572B1 (en) | 1973-05-09 | 1974-05-08 | METHOD OF MAKING THE SODIUM SALT OF ITACONIC ACID |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5013319A (en) |
| AR (1) | AR209749A1 (en) |
| AT (1) | AT332368B (en) |
| BE (1) | BE814616A (en) |
| BG (1) | BG25205A3 (en) |
| BR (1) | BR7403403D0 (en) |
| CH (1) | CH603529A5 (en) |
| CS (1) | CS184765B2 (en) |
| DD (1) | DD111365A5 (en) |
| DE (1) | DE2422375A1 (en) |
| EG (1) | EG11957A (en) |
| ES (1) | ES426245A1 (en) |
| FR (1) | FR2228760B1 (en) |
| GB (1) | GB1418451A (en) |
| HU (1) | HU169262B (en) |
| IE (1) | IE39754B1 (en) |
| IN (1) | IN140247B (en) |
| IT (1) | IT987221B (en) |
| LU (1) | LU70019A1 (en) |
| MW (1) | MW1574A1 (en) |
| NL (1) | NL7406207A (en) |
| PL (1) | PL99572B1 (en) |
| RO (1) | RO63044A (en) |
| SE (1) | SE425732B (en) |
| ZA (1) | ZA742522B (en) |
| ZM (1) | ZM7074A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4480125A (en) * | 1981-11-16 | 1984-10-30 | Polaroid Corporation | Itaconamide compounds and method of preparation |
| GB201506308D0 (en) * | 2015-04-14 | 2015-05-27 | Lucite Int Uk Ltd | A process for the production of ethylenically unsaturated carboxylic acids or esters |
-
1973
- 1973-05-09 IT IT23862/73A patent/IT987221B/en active
-
1974
- 1974-04-19 ZA ZA00742522A patent/ZA742522B/en unknown
- 1974-04-22 RO RO7400078518A patent/RO63044A/en unknown
- 1974-04-24 EG EG138/74D patent/EG11957A/en active
- 1974-04-25 BR BR3403/74A patent/BR7403403D0/en unknown
- 1974-04-26 MW MW15/74*UA patent/MW1574A1/en unknown
- 1974-04-29 FR FR7414888A patent/FR2228760B1/fr not_active Expired
- 1974-04-30 ZM ZM70/74A patent/ZM7074A1/en unknown
- 1974-05-01 GB GB1919574A patent/GB1418451A/en not_active Expired
- 1974-05-02 IE IE939/74A patent/IE39754B1/en unknown
- 1974-05-06 BE BE143982A patent/BE814616A/en unknown
- 1974-05-07 AR AR253632A patent/AR209749A1/en active
- 1974-05-07 ES ES426245A patent/ES426245A1/en not_active Expired
- 1974-05-08 PL PL1974170923A patent/PL99572B1/en unknown
- 1974-05-08 CH CH627574A patent/CH603529A5/xx not_active IP Right Cessation
- 1974-05-08 NL NL7406207A patent/NL7406207A/xx not_active Application Discontinuation
- 1974-05-08 AT AT379674A patent/AT332368B/en not_active IP Right Cessation
- 1974-05-08 DD DD178371A patent/DD111365A5/xx unknown
- 1974-05-08 HU HUSA2640A patent/HU169262B/hu unknown
- 1974-05-08 CS CS7400003334A patent/CS184765B2/en unknown
- 1974-05-08 LU LU70019A patent/LU70019A1/xx unknown
- 1974-05-09 IN IN1034/CAL/74A patent/IN140247B/en unknown
- 1974-05-09 JP JP49050798A patent/JPS5013319A/ja active Pending
- 1974-05-09 SE SE7406232A patent/SE425732B/en unknown
- 1974-05-09 DE DE2422375A patent/DE2422375A1/en active Pending
- 1974-05-09 BG BG026640A patent/BG25205A3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7406207A (en) | 1974-11-12 |
| FR2228760B1 (en) | 1978-03-31 |
| EG11957A (en) | 1978-06-30 |
| ES426245A1 (en) | 1976-07-01 |
| CS184765B2 (en) | 1978-09-15 |
| IE39754L (en) | 1974-11-09 |
| GB1418451A (en) | 1975-12-17 |
| AR209749A1 (en) | 1977-05-31 |
| CH603529A5 (en) | 1978-08-15 |
| BG25205A3 (en) | 1978-08-10 |
| FR2228760A1 (en) | 1974-12-06 |
| MW1574A1 (en) | 1975-05-13 |
| BR7403403D0 (en) | 1974-12-03 |
| RO63044A (en) | 1978-05-15 |
| IE39754B1 (en) | 1978-12-20 |
| DD111365A5 (en) | 1975-02-12 |
| ZA742522B (en) | 1975-06-25 |
| ATA379674A (en) | 1976-01-15 |
| JPS5013319A (en) | 1975-02-12 |
| IT987221B (en) | 1975-02-20 |
| DE2422375A1 (en) | 1974-11-28 |
| ZM7074A1 (en) | 1974-12-20 |
| LU70019A1 (en) | 1974-10-01 |
| SE425732B (en) | 1982-11-01 |
| BE814616A (en) | 1974-09-02 |
| AT332368B (en) | 1976-09-27 |
| IN140247B (en) | 1976-10-02 |
| AU6814174A (en) | 1975-10-23 |
| HU169262B (en) | 1976-10-28 |
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