CH619960A5 - Process for the preparation of tris(hydroxymethyl)-aminomethane-gluconate dihydroxy-aluminate - Google Patents
Process for the preparation of tris(hydroxymethyl)-aminomethane-gluconate dihydroxy-aluminate Download PDFInfo
- Publication number
- CH619960A5 CH619960A5 CH555475A CH555475A CH619960A5 CH 619960 A5 CH619960 A5 CH 619960A5 CH 555475 A CH555475 A CH 555475A CH 555475 A CH555475 A CH 555475A CH 619960 A5 CH619960 A5 CH 619960A5
- Authority
- CH
- Switzerland
- Prior art keywords
- gluconate
- hydroxymethyl
- tris
- aluminum
- aminomethane
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 title claims description 8
- GJJYZOBRHIMORS-GQOAHPRESA-K aloglutamol Chemical compound OCC(N)(CO)CO.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)O[Al](O)O GJJYZOBRHIMORS-GQOAHPRESA-K 0.000 title abstract 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims abstract description 15
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000012208 gluconic acid Nutrition 0.000 claims abstract description 11
- 229950006191 gluconic acid Drugs 0.000 claims abstract description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229960003681 gluconolactone Drugs 0.000 claims abstract description 5
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 claims abstract description 4
- ICPMTQOYWXXMIG-OPDGVEILSA-K aluminum;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Al+3].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O ICPMTQOYWXXMIG-OPDGVEILSA-K 0.000 claims abstract description 4
- 235000012209 glucono delta-lactone Nutrition 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 238000010907 mechanical stirring Methods 0.000 claims abstract description 3
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000174 gluconic acid Substances 0.000 abstract description 4
- 230000001458 anti-acid effect Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000004411 aluminium Substances 0.000 abstract 2
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 abstract 2
- 238000004090 dissolution Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- -1 hydroxy aluminate Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
io La presente invenzione riguarda un nuovo procedimento di fabbricazione industriale di tris (idrossimetil)-aminome-tan-gluconato- di idrossi alluminato la cui formula bruta è: C10Ha3O12N Al, di peso molecolare 376,27 ed avente la seguente formula di struttura: The present invention relates to a new industrial manufacturing process of tris (hydroxymethyl) -aminome-tan-gluconate- of hydroxy aluminate whose brute formula is: C10Ha3O12N Al, of molecular weight 376.27 and having the following structural formula:
CHo0H CHo0H
H(\ I 2 H (\ I 2
V 1 V 1
A1-0~CH2-(CH0H)4-CQ0H . NH2-C-CH20H (I) A1-0 ~ CH2- (CH0H) 4-CQ0H. NH2-C-CH20H (I)
W CH20H W CH20H
Il composto ottenuto con il procedimento secondo la pre-25 sente invenzione è già noto in letteratura (vedi Journal of Pharmaceutical Sciences - voi. 56, n. 2, febbraio 1967); di tale composto è già nota ed è stata studiata l'attività come antiacido ideale, per la sua alta capacità neutralizzante per unità di peso. The compound obtained with the process according to the present invention is already known in the literature (see Journal of Pharmaceutical Sciences - vol. 56, n. 2, February 1967); of this compound is already known and its activity as an ideal antacid has been studied, due to its high neutralizing capacity per weight unit.
30 Tuttavia i procedimenti noti e descritti per ottenere il prodotto (I) sono adatti solo ed esclusivamente per metodi di laboratorio, mentre per produzioni industriali essi non sono accettabili per le intrinseche ed obiettive difficoltà, evidenti per qualsiasi esporto dell'arte. 30 However, the known and described processes for obtaining the product (I) are suitable only and exclusively for laboratory methods, while for industrial production they are not acceptable due to the intrinsic and objective difficulties evident for any export of the art.
35 Per la preparazione del composto in oggetto sono noti i seguenti procedimenti: 35 The following processes are known for preparing the compound in question:
— Reazione di acido gluconico in soluzione acquosa con THAM e successiva aggiunta di alluminio isopropilato disciolto in alcool isopropilico. ' - Reaction of gluconic acid in aqueous solution with THAM and subsequent addition of isopropylated aluminum dissolved in isopropyl alcohol. '
40 — Reazione di acido gluconico con THAM e successiva aggiunta di alluminio isopropilato solido in polvere. 40 - Reaction of gluconic acid with THAM and subsequent addition of solid isopropylated aluminum in powder form.
Questi metodi noti si prestano male ad essere attuati su scala industriale. These known methods are not suitable for being implemented on an industrial scale.
Per ovviare a tale inconveniente la presente invenzione 45 propone un procedimento di fabbricazione industriale del tris (idrossimetil) aminometan-gluconato-diidrossi-alluminato secondo il seguente schema di reazioni: To overcome this drawback, the present invention 45 proposes an industrial manufacturing process of tris (hydroxymethyl) aminomethan-gluconate-dihydroxy-aluminate according to the following reaction scheme:
619960 619960
CH?~0H CH? 0H ~
Ah-oh I Ah-oh I
(j- H—0 H CH-OH (j- H — 0 H CH-OH
Ah-oh Ah-oh
I ' COOH I 'COOH
CH CH
*<3/CH * <3 / CH
3 3
.CH. .CH.
9H 9H
îl-0^3 IL-0 ^ 3
i \ i \
XCH XCH
CH,.OH CH, .OH
i the
II N-C-CH OH II N-C-CH OH
ÎH2oh ÎH2oh
CH -O-A.l CH -O-A.l
I 2 I 2
CH-OH CH-OH
Ah-oh l Ah-oh l
(j'.H-CH OH-CH (j'.H-CH OH-CH
Aoo ■ Aoo ■
■OH -OH ■ OH -OH
CH OH CH OH
H^N-C-CHo0H 3 '- H ^ N-C-CHo0H 3 '-
CH?0H CH? 0H
+ +
H- H-
3 CH^-CH-CH, OH 3 CH ^ -CH-CH, OH
In particolare, partendo da gluconolattone si ottiene per soluzione ed idrolisi in acqua una soluzione di acido D-glu-conico che si fa, secondo l'invenzione, reagire in una prima tappa con alluminio isopropilato; in una seconda fase il glu-conato di alluminio viene fatto reagire con trisidrossimetil aminometano per ottenere il prodotto (I). In particular, starting from gluconolactone, a solution of D-gluconic acid is obtained by solution and hydrolysis in water which, according to the invention, is reacted in a first step with isopropylated aluminum; in a second step, the aluminum gluconate is reacted with trishydroxymethyl aminomethane to obtain the product (I).
La presente invenzione potrà essere meglio compresa dal seguente esempio di messa in opera dell'invenzione dato a puro titolo indicativo e pertanto non limitativo: The present invention can be better understood from the following example of implementation of the invention given purely by way of non-limiting example:
Esempio Example
In un beaker da 21 si sciolgono 375 g di gluconolattone in 720 mi di acqua sotto agitazione meccanica; il tempo per avere soluzione completa e conseguente idrolisi da 8-glucono-lattone ad acido D-gluconico è circa 3 h. Si ottiene una soluzione di acido D-gluconico che, all'analisi, ha dato un titolo del 44,3%. In a 21 beaker 375 g of gluconolactone are dissolved in 720 ml of water under mechanical stirring; the time to obtain complete solution and consequent hydrolysis from 8-glucono-lactone to D-gluconic acid is about 3 h. A solution of D-gluconic acid is obtained which, upon analysis, gave a titer of 44.3%.
In un pallone da 3 1 si caricano 810 mi della soluzione di acido gluconico al 44,3 %, 1200 mi di acqua e 381 g di alluminio isopropilato; si porta la miscela sotto agitazione a 810 ml of the 44.3% gluconic acid solution, 1200 ml of water and 381 g of isopropylated aluminum are loaded into a 3 1 flask; the mixture is stirred a
65°C e si lascia fino a completa soluzione (circa 3 h) si raffredda e si precipita con circa 1200 mi di acetone, si filtra, si lava bene spappolando il prodotto 2 volte con 200 mi di acetone e si essicca in stufa sotto vuoto a 45-50°C. 35 Si ottengono 440 g, con resa dell'88% ed un titolo 94,5%. 65 ° C and is left until complete solution (about 3 h), it is cooled and precipitated with about 1200 ml of acetone, filtered, washed well by pulping the product twice with 200 ml of acetone and dried in a stove under vacuum. at 45-50 ° C. 35 440 g are obtained, with a yield of 88% and a titer of 94.5%.
20 g al 94,5% (0,737 moli = al 100%) di gluconato di alluminio (PM = 256,17 - titolo 94,5 %) sono sciolti in 50 mi di acqua; a questa soluzione si aggiungono sotto agitazione 8,93 g (0,737 moli) di trisidrossimetil aminometano (PM = 40 121) sciolti in 15 mi di acqua, si lascia sotto agitazione a freddo per 30 minuti (soluzione completa) indi si evapora con lo spray-dryng. Si ottengono 28,5 g del prodotto di formula (I). 20 g of 94.5% (0.737 moles = 100%) of aluminum gluconate (PM = 256.17 - 94.5% titer) are dissolved in 50 ml of water; 8.93 g (0.737 moles) of trishydroxymethyl aminomethane (PM = 40 121) dissolved in 15 ml of water are added under stirring, left under cold stirring for 30 minutes (complete solution) then evaporated with the spray -dryng. 28.5 g of the product of formula (I) are obtained.
Il potere tamponante del prodotto ottenuto secondo l'invenzione è di circa 110-120 ml HCl 01 N, sul prodotto per-45 fettamente anidro. The buffering power of the product obtained according to the invention is about 110-120 ml HCl 01 N, on the product perfectly dry.
Benché sia stato dato un solo esempio di messa in opera del procedimento secondo l'invenzione, sarà ora facile ad un esperto del ramo provvedere a numerose modifiche e varianti che devono ritenersi tutte comprese nell'ambito del presente so trovato. Although only one example of implementation of the method according to the invention has been given, it will now be easy for a person skilled in the art to make numerous modifications and variations which must be considered all included within the scope of the present invention.
v v
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT308074 | 1974-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619960A5 true CH619960A5 (en) | 1980-10-31 |
Family
ID=11104418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH555475A CH619960A5 (en) | 1974-05-22 | 1975-04-30 | Process for the preparation of tris(hydroxymethyl)-aminomethane-gluconate dihydroxy-aluminate |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH619960A5 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2524470A1 (en) * | 1982-04-05 | 1983-10-07 | Corvi Camillo Spa | ORGANOMETALLIC COMPLEXES OF N-CYCLOHEXYL-PIPERAZINO-ACETAMIDES OR -PROPIONAMIDES, PREPARATION AND USE OF SUCH SUBSTANCES AS BUFFER MEDICINES TO COMBAT ULCERES AND SECRETION FORMATION |
-
1975
- 1975-04-30 CH CH555475A patent/CH619960A5/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2524470A1 (en) * | 1982-04-05 | 1983-10-07 | Corvi Camillo Spa | ORGANOMETALLIC COMPLEXES OF N-CYCLOHEXYL-PIPERAZINO-ACETAMIDES OR -PROPIONAMIDES, PREPARATION AND USE OF SUCH SUBSTANCES AS BUFFER MEDICINES TO COMBAT ULCERES AND SECRETION FORMATION |
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| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |