CH620193A5 - Process for preparing salts of carbonic acid monoesters - Google Patents

Process for preparing salts of carbonic acid monoesters Download PDF

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Publication number
CH620193A5
CH620193A5 CH1594275A CH1594275A CH620193A5 CH 620193 A5 CH620193 A5 CH 620193A5 CH 1594275 A CH1594275 A CH 1594275A CH 1594275 A CH1594275 A CH 1594275A CH 620193 A5 CH620193 A5 CH 620193A5
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CH
Switzerland
Prior art keywords
reaction
alcohol
process according
carried out
carbonic acid
Prior art date
Application number
CH1594275A
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Italian (it)
Inventor
Gioacchino Cipriani
Carlo Neri
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Anic Spa
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Publication of CH620193A5 publication Critical patent/CH620193A5/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00Preparation of esters of carbonic or haloformic acids
    • C07C68/04Preparation of esters of carbonic or haloformic acids from carbon dioxide or inorganic carbonates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/141Feedstock

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Inorganic Fibers (AREA)

Abstract

The technical problem of preparing certain salts of carbonic acid monoesters is solved by reacting the alcohol corresponding to the desired monoester with carbon dioxide and a compound of the metal to be introduced into the molecule of the said monoester.

Description

620193 620193

Claims (6)

RIVENDICAZIONI 1. Procedimento per la preparazione di sali di monoesteri dell'acido carbonico di formula1. Process for the preparation of monoester salts of the carbonic acid of formula (RO—C—0)uMe(RO—C—0)uMe IIII OOR nella quale R è un radicale alchilico, arilico, cicloalchilico, o arilalchilico, semplice o sostituito, mono o poliossidrilato, saturo o insaturo; n è 1 o 2 ed Me è un metallo alcalino o alca-lino-terroso, consistente nel far reagire i corrispondenti alcoli con anidride carbonica ed un composto del metallo di formula MemX„ nella quale X è scelto fra C03=, S03=, 0=, OH", B0 r, S=, SH~, m è 1, 2 o 3, ed n ha i valori sopra riportati.wherein R is an alkyl, aryl, cycloalkyl, or arylalkyl radical, simple or substituted, mono or polyhydroxylated, saturated or unsaturated; n is 1 or 2 and Me is an alkali or alkaline-earth metal, consisting in reacting the corresponding alcohols with carbon dioxide and a compound of the metal of the formula MemX„ in which X is selected from C03=, S03=, 0 =, OH", B0 r, S=, SH~, m is 1, 2 or 3, and n has the above values. 2. Procedimento secondo la rivendicazione 1, caratterizzato dal fatto che la reazione viene effettuata ad una pressione di CO. variabile dalla pressione ambiente a 100 atm.2. Process according to claim 1, characterized in that the reaction is carried out at a pressure of CO. variable from ambient pressure to 100 atm. 3. Procedimento secondo la rivendicazione 1, caratterizzato dal fatto che la reazione viene effettuata a temperature comprese fra la temperatura di congelamento e quella di ebollizione dell'alcool impiegato.3. Process according to claim 1, characterized in that the reaction is carried out at temperatures comprised between the freezing point and the boiling point of the alcohol used. 4. Procedimento secondo la rivendicazione 3, caratterizzato dal fatto che la reazione viene preferibilmente effettuata a temperature comprese fra 0 e 60°C.4. Process according to claim 3, characterized in that the reaction is preferably carried out at temperatures ranging from 0 to 60°C. 5. Procedimento secondo la rivendicazione 1, caratterizzato dal fatto che la reazione viene effettuata in presenza del solo alcool come mezzo di reazione.5. Process according to claim 1, characterized in that the reaction is carried out in the presence of only alcohol as reaction medium. 6. Procedimento secondo la rivendicazione 1, caratterizzato dal fatto che la reazione viene effettuata in presenza di un solvente inerte alla stessa.6. Process according to claim 1, characterized in that the reaction is carried out in the presence of a solvent inert thereto. La presente invenzione concerne un procedimento per la preparazione di sali di monoesteri dell'acido carbonico di formulaThe present invention relates to a process for the preparation of monoester salts of the carbonic acid of formula (RO—C—0)nMe(RO—C—0)nMe IIII OOR nella quale R è un radicale alchilico, arilico, cicloalchilico, o arilalchilico, semplice o sostituito mono o poliossidrilato, saturo o insaturo, n è 1 o 2 ed Me è un metallo alcalino o al-calino-terroso, consistente nel far reagire i corrispondenti alcoli con anidride carbonica ed un composto del metallo di formula MemX„ nella quale X è scelto fra COa=, S03=, 0=, OH", B03=, S , SH~, m è 1, 2 o 3, ed n ha i valori sopra riportati.in which R is an alkyl, aryl, cycloalkyl, or arylalkyl radical, simple or substituted mono or polyhydroxylated, saturated or unsaturated, n is 1 or 2 and Me is an alkali or alkaline-earth metal, consisting in reacting the corresponding alcohols with carbon dioxide and a metal compound of the formula MemX„ in which X is selected from COa=, S03=, 0=, OH", B03=, S , SH~, m is 1, 2 or 3, and n has the above values. La reazione, che procede secondo il seguente schema MeÄ + n COo + „ROH (ROCOO)„Me + HnXn Mem_! avviene semplicemente facendo passare una corrente di C02 attraverso una soluzione o sospensione del sale scelto nell'alcool cui si è interessati, preferibilmente sotto agitazione. La pressione di C02 può variare dalla pressione ambiente a 100 atm., mentre la temperatura è mantenuta tra quella di congelamento ed ebollizione dell'alcool, preferibilmente tra 0 e 60°C.The reaction, which proceeds according to the following scheme MeÄ + n COo + „ROH (ROCOO)„Me + HnXn Mem_! it occurs simply by passing a stream of C02 through a solution or suspension of the selected salt in the alcohol in question, preferably under stirring. The pressure of C02 can vary from ambient pressure to 100 atm., while the temperature is maintained between the freezing and boiling temperatures of the alcohol, preferably between 0 and 60°C. Si può altresì operare in presenza di un solvente qualsiasi purché inerte agli effetti della reazione in oggetto.It is also possible to operate in the presence of any solvent provided it is inert to the effects of the reaction in question. I sali dei monoesteri dell'acido carbonico possono essere isolati per filtrazione, se insolubili, o precipitati con adatto solvente o, infine, per evaporazione del mezzo di reazione.The salts of the carbonic acid monoesters can be isolated by filtration, if insoluble, or precipitated with a suitable solvent or, lastly, by evaporation of the reaction medium. Essi possono essere impiegati al posto dei corrispondenti alcolati nelle reazioni di condensazione, ad esempio nelle condensazioni di aldeidi con molecole a idrogeni attivi, o di esteri con uree, oppure quali catalizzatori nelle reazioni di disproporzione di aldeidi aromatiche.They can be used instead of the corresponding alcoholates in the condensation reactions, for example in the condensation of aldehydes with active hydrogen molecules, or of esters with ureas, or as catalysts in the disproportionation reactions of aromatic aldehydes. Rispetto agli alcolati, i sali ottenuti secondo la presente invenzione esercitano, nelle suddette reazioni, un'azione più blanda, limitano le reazioni parassite ed inoltre presentano un costo inferiore.Compared to the alcoholates, the salts obtained according to the present invention exert a milder action in the above reactions, limit the parasitic reactions and furthermore have a lower cost. Quanto detto risulterà più evidente dall'esame degli esempi seguenti, con i quali si intende illustrare l'invenzione, quale definita nella rivendicazione 1.What has been said will become more evident from an examination of the following examples, with which it is intended to illustrate the invention, as defined in claim 1. Esempio 1Example 1 10 g di K2C03 anidro vengono sospesi in 100 cc di metanolo anidro; si fa passare un flusso di C02 leggermente superiore a quella assorbita, sotto buona agitazione, a 25°C.10 g of anhydrous K2CO3 are suspended in 100 cc of anhydrous methanol; a flow of C02 slightly higher than that absorbed is passed, under good stirring, at 25°C. La reazione è esotermica e veloce ed è completa entro 30'. Quando l'assorbimento è cessato si filtra il residuo (KHC03) e si evapora sotto vuoto la soluzione; si ottengono 8,5 g di KOCOOCHs impuro per tracce di KHC03.The reaction is exothermic and fast and is complete within 30'. When the absorption has ceased, the residue (KHC03) is filtered and the solution is evaporated under vacuum; 8.5 g of KOCOOCHs impure for traces of KHC03 are obtained. Esempio 2Example 2 5,6 g di CaO vengono sospesi in 100 cc di alcool allilico e agitati a 25°C in flusso di C02; si ha reazione esotermica e veloce che è completa in 35'. Il precipitato bianco voluminoso viene filtrato sotto N2, lavato con etere etilico e seccato sotto vuoto; si ottengono 20 g di Ca(OCOOCH2CH=CH2)2.5.6 g of CaO are suspended in 100 cc of allyl alcohol and stirred at 25°C in a stream of CO2; there is a fast exothermic reaction which is complete in 35'. The voluminous white precipitate is filtered under N2, washed with ethyl ether and dried under vacuum; 20 g of Ca(OCOOCH2CH=CH2)2 are obtained. Esempio 3Example 3 10 g di NaOCOOCH3 (0,1 moli) vengono disciolti in 100 mi di metanolo; si aggiungono 16 g di dietilmalonato e 6 g di urea. Si tiene a ricadere il tutto per circa 8 ore, quindi si tira a secco sotto vuoto per ottenere circa 15 g di sale sodico dell'acido barbiturico.10 g of NaOCOOCH3 (0.1 moles) are dissolved in 100 ml of methanol; 16 g of diethyl malonate and 6 g of urea are added. The whole is kept under reflux for about 8 hours, then it is dried under vacuum to obtain about 15 g of sodium salt of barbituric acid. Quest'ultimo, dopo idrolisi con HCl 2N ed estrazione con etere da gr. 12 di acido barbiturico.The latter, after hydrolysis with 2N HCl and extraction with ether from gr. 12 of barbituric acid. Esempio 4Example 4 12 g di cianuro di benzile e 11 g di benzaldeide e 10 g di NaCCOOCHj vengono disciolti in 100 mi di metanolo e tenuti a ricadere per due ore. Si filtra a caldo il sodio carbonato e si evapora sotto vuoto il solvente; si ottengono 22 g di fe-nilcinnamonitrile impuro per Na2C03. Si ottiene puro lavando con acqua.12 g of benzyl cyanide and 11 g of benzaldehyde and 10 g of NaCCOOCHj are dissolved in 100 ml of methanol and kept under reflux for two hours. The sodium carbonate was filtered while hot and the solvent was evaporated under vacuum; 22 g of impure phenylcinnamonitrile per Na2 CO3 are obtained. It is obtained pure by washing with water. 22 55 1010 1515 2020 2525 3030 3535 4040 4545 5050 Vv
CH1594275A 1974-12-10 1975-12-08 Process for preparing salts of carbonic acid monoesters CH620193A5 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT30338/74A IT1026904B (en) 1974-12-10 1974-12-10 PROCEDURE FOR THE PREPARATION OF MONOESTER SALTS OF CARBONIC ACID

Publications (1)

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CH620193A5 true CH620193A5 (en) 1980-11-14

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CH1594275A CH620193A5 (en) 1974-12-10 1975-12-08 Process for preparing salts of carbonic acid monoesters

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JP (1) JPS593982B2 (en)
AT (1) AT343090B (en)
BE (1) BE836385A (en)
CA (1) CA1058204A (en)
CH (1) CH620193A5 (en)
DE (1) DE2555567C3 (en)
DK (1) DK142749B (en)
ES (1) ES443588A1 (en)
FR (1) FR2294160A1 (en)
GB (1) GB1523477A (en)
IE (1) IE42376B1 (en)
IT (1) IT1026904B (en)
LU (1) LU73950A1 (en)
NL (1) NL175520C (en)
NO (1) NO144703C (en)
SE (1) SE426390B (en)
SU (1) SU656503A3 (en)
ZA (1) ZA757614B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0488860A1 (en) * 1990-11-30 1992-06-03 Rhone-Poulenc Chimie Method for the production of polyalkoxylated aromatic compounds

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4123446A (en) * 1977-04-11 1978-10-31 Allied Chemical Corporation Synthesis of metal alkyl carbonates
US4217298A (en) * 1977-09-05 1980-08-12 Tokuyama Soda Kabushiki Kaisha Process for preparing organic carbonates
DE2748718A1 (en) * 1977-10-29 1979-05-03 Bayer Ag PROCESS FOR THE PRODUCTION OF DIALKYLCARBONATES
JPH0251684U (en) * 1988-10-03 1990-04-12

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0488860A1 (en) * 1990-11-30 1992-06-03 Rhone-Poulenc Chimie Method for the production of polyalkoxylated aromatic compounds
FR2669925A1 (en) * 1990-11-30 1992-06-05 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF POLYALKOXYL AROMATIC COMPOUNDS

Also Published As

Publication number Publication date
DK142749B (en) 1981-01-12
DE2555567B2 (en) 1978-10-12
IT1026904B (en) 1978-10-20
ES443588A1 (en) 1977-05-01
CA1058204A (en) 1979-07-10
ATA932875A (en) 1977-09-15
DK142749C (en) 1981-08-17
LU73950A1 (en) 1976-07-01
IE42376B1 (en) 1980-07-30
FR2294160B1 (en) 1980-04-25
NL7514361A (en) 1976-06-14
BE836385A (en) 1976-06-08
FR2294160A1 (en) 1976-07-09
AT343090B (en) 1978-05-10
NO754159L (en) 1976-06-11
DE2555567C3 (en) 1979-06-07
JPS5182214A (en) 1976-07-19
IE42376L (en) 1976-06-10
NL175520B (en) 1984-06-18
ZA757614B (en) 1976-11-24
GB1523477A (en) 1978-08-31
JPS593982B2 (en) 1984-01-27
DE2555567A1 (en) 1976-06-16
NL175520C (en) 1984-11-16
NO144703C (en) 1981-10-21
NO144703B (en) 1981-07-13
SU656503A3 (en) 1979-04-05
SE426390B (en) 1983-01-17
SE7513876L (en) 1976-06-11
DK557375A (en) 1976-06-11

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