14858-73-2

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C17H34O3/c1-5-9-11-15(7-3)13-19-17(18)20-14-16(8-4)12-10-6-2/h15-16H,5-14H2,1-4H3

Synthetic route

2-Ethylhexyl alcohol (104-76-7) + urea (57-13-6) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
With diisobutylaluminum hydride; triphenylphosphine In toluene at 160 - 270℃; for 16h;	87%

2-Ethylhexyl alcohol (104-76-7) + Diethyl carbonate (105-58-8) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
With di(n-butyl)tin oxide at 140℃; for 26h;	70.6%

2-Ethylhexyl alcohol (104-76-7) + carbon dioxide (124-38-9) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 18h;	61%
1,1,3,3-tetrabutyl-1,3-bis(2-ethylhexyloxy)distannoxane In water at 120℃; for 600h; Industry scale; Autoclave;

methanol (67-56-1) + carbon dioxide (124-38-9) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
dibutyl-bis(2-ethylhexyloxy)tin; 1,1,3,3-tetrabutyl-1,3-bis(2-ethylhexyloxy)distannoxane In 2-Ethylhexyl alcohol at 120℃; under 22502.3 - 26252.6 Torr; for 4h;	25%

dibutyl-bis(2-ethylhexyloxy)tin (149746-25-8) + 1,1,3,3-tetrabutyl-1,3-bis(2-ethylhexyloxy)distannoxane (10301-02-7) + tributyl-(2-ethylhexyloxy)-tin (3644-24-4) + carbon dioxide (124-38-9) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
at 120℃; under 30003 Torr; for 3.16667h; Product distribution / selectivity;	25%

dibutyl-bis(2-ethylhexyloxy)tin (149746-25-8) + 1,1,3,3-tetrabutyl-1,3-bis(2-ethylhexyloxy)distannoxane (10301-02-7) + tributyl-(2-ethylhexyloxy)-tin (3644-24-4) + carbon dioxide (124-38-9) → carbon dioxide adduct of tributyltin(2-ethylhexyloxide) + bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
at 120℃; under 30003 Torr; for 3.16667h; Product distribution / selectivity;	A 0.1% B 25%

2-Ethylhexyl alcohol (104-76-7) + magnesium acetate (142-72-3, 92123-19-8) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
With triphenylphosphine; urea

dibutyl-bis(2-ethylhexyloxy)tin (149746-25-8) + tributyl-(2-ethylhexyloxy)-tin (3644-24-4) + carbon dioxide (124-38-9) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
at 130℃; Gas phase;

dibutyl-bis(2-ethylhexyloxy)tin (149746-25-8) + carbon dioxide (124-38-9) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
1,1,3,3-tetrabutyl-1,3-bis(2-ethylhexyloxy)distannoxane at 120℃; under 30003 Torr; for 4h; Autoclave; Industry scale;

dibutyl-bis(2-ethylhexyloxy)tin (149746-25-8) + 1,1,3,3-tetrabutyl-1,3-bis(2-ethylhexyloxy)distannoxane (10301-02-7) + carbon dioxide (124-38-9) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
at 100 - 120℃; under 30753.1 Torr; for 4h; Large scale;

2-Ethylhexyl alcohol (104-76-7) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2.67 h / 157 °C / 150.01 - 750.08 Torr / Inert atmosphere; Large scale 2: 140 °C / 315.03 Torr / Large scale 3: 4 h / 100 - 120 °C / 30753.1 Torr / Large scale View Scheme

1,1,3,3-tetrabutyl-1,3-bis(2-ethylhexyloxy)distannoxane (10301-02-7) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 140 °C / 315.03 Torr / Large scale 2: 4 h / 100 - 120 °C / 30753.1 Torr / Large scale View Scheme

2-Ethylhexyl alcohol (104-76-7) + 2-Ethylhexyl chloroformate (24468-13-1) → bis(2-ethylhexyl) carbonate (14858-73-2)

Conditions	Yield
Stage #1: 2-Ethylhexyl alcohol With pyridine In hexane at 20℃; Stage #2: 2-Ethylhexyl chloroformate In hexane at 80℃; for 3.5h;

Upstream product

• 104-76-7 2-Ethylhexyl alcohol 
• 124-38-9 carbon dioxide 
• 67-56-1 methanol 
• 149746-25-8 dibutyl-bis(2-ethylhexyloxy)tin 
• 10301-02-7 1,1,3,3-tetrabutyl-1,3-bis(2-ethylhexyloxy)distannoxane 
• 3644-24-4 tributyltin(2-ethylhexyloxide) 
• 142-72-3 magnesium acetate 
• 24468-13-1 2-Ethylhexyl chloroformate 
• 105-58-8 Diethyl carbonate 
• 57-13-6 urea 

Relevant academic research and scientific papers

Synthesis and Characterization of Dialkyl Carbonates Prepared from Mid-, Long-Chain, and Guerbet Alcohols

A series of organic carbonates derived from mid-, long-chain, and Guerbet alcohols were synthesized in good yields (69-80% isolated yields after purification by distillation or recrystallization) through a carbonate interchange reaction by heating the linear or Guerbet alcohols with diethyl carbonate in the presence of catalyst, n-dibutyltin oxide. The carbonates were isolated by Kuegelrohr distillation or recrystallization from acetone and characterized using FTIR, GC, 11H and 13C NMR spectroscopy, and GC-MS. El and positive Cl mass-spectral techniques were used to characterize the carbonates. Such materials are currently of commercial interest as lubricants and additives in various industrial applications.

Lubricant composition, magnetic recording medium, and novel polyether compound

An aspect of the present invention relates to a lubricant composition comprising a polyether compound comprising an alkylene oxide residue and a carbonic acid ester residue.

Mixture for recovery utilization or transfer of carbon dioxide

It is an object of the present invention to provide a mixture for recovery utilization or transfer of carbon dioxide gas. According to the present invention, disclosed is a mixture containing carbon dioxide and an alkyltin alkoxide composition containing carbon dioxide complex of an alkyltin alkoxide, the mixture having a composition with a specified ratio.

PROCESS FOR PRODUCING ISOCYANATE

An object of the present invention is to provide a process that enables isocyanate to be produced stably over a long period of time and at high yield without encountering problems of the prior art during production of isocyanate without using phosgene. The present invention discloses a process for producing an isocyanate by subjecting a carbamic acid ester to a thermal decomposition reaction, including the steps of: recovering a low boiling point component in a form of a gaseous phase component from a thermal decomposition reaction vessel in which the thermal decomposition reaction is carried out; recovering a liquid phase component containing a carbamic acid ester from a bottom of the thermal decomposition reaction vessel; and supplying all or a portion of the liquid phase component to an upper portion of the thermal decomposition reaction vessel.

ISOCYANATE PRODUCTION PROCESS

An object of the present invention is to provide a process that enables isocyanate to be produced stably over a long period of time and at high yield without encountering problems of the prior art during production of isocyanate without using phosgene. The present invention discloses a process for producing an isocyanate by subjecting a carbamic acid ester to a thermal decomposition reaction, including the steps of: recovering a low boiling point component in a form of a gaseous phase component from a thermal decomposition reaction vessel in which the thermal decomposition reaction is carried out; recovering a liquid phase component containing a carbamic acid ester from a bottom of the thermal decomposition reaction vessel; and supplying all or a portion of the liquid phase component to an upper portion of the thermal decomposition reaction vessel.

PROCESS FOR PRODUCTION OF ALKYLTIN ALKOXIDES

A process for the production of alkyltin alkoxides which comprises subjecting at least one alkyltin compound selected from among organotin compounds having tin-oxygen-tin linkages as the starting compound and a hydroxyl compound as the reactant to dehydration to obtain an alkyltin alkoxide corresponding to the starting compound and the reactant, characterized by continuously feeding the starting compound and the reactant into a reactor, discharging a water-containing low boiling point component from the reactor, and continuously withdrawing a reaction fluid containing an alkyltin alkoxide as the bottom from the reactor.

PROCESS FOR PRODUCING CARBONIC ESTER

A method for producing a carbonic ester, comprising: (1) performing a reaction between an organometal compound mixture and carbon dioxide, the organometal compound mixture comprising a reactive organometal compound and an unregenerable unreactive compound derived from the reactive organometal compound, to thereby obtain a reaction mixture containing a carbonic ester, the unregenerable unreactive compound, and a regenerable metamorphic organometal compound derived from the reactive organometal compound, (2) separating the reaction mixture into a first portion containing the carbonic ester and the unregenerable unreactive compound, and a second portion containing the regenerable meta-, morphic organometal compound, and (3) reacting the second portion of the reaction mixture with an alcohol to form an organometal compound mixture and water and removing the water from the organometal compound mixture, the organometal compound mixture comprising a reactive organometal compound and an unregenerable unreactive compound derived from the reactive organometal compound.

PROCESS FOR PRODUCING CARBONIC ESTER

A method for producing a carbonic ester, comprising (1) performing a reaction between an organometal compound having a metal-oxygen-carbon linkage and carbon dioxide to obtain a reaction mixture containing a carbonic ester formed by the reaction, (2) separating the carbonic ester from the reaction mixture to obtain a residual liquid, and (3) reacting the residual liquid with an alcohol to form an organometal compound having a metal-oxygen-carbon linkage and form water and removing the water from the organometal compound, wherein the organometal compound obtained in step (3) is recovered for recycle thereof to step (1).

Process for the preparation of carbonic acid esters

The present invention relates to a process for the preparation of carbonic acid esters of monoalcohols or polyalcohols, which is characterized in that ureas are reacted with monoalcohols or with polyalcohols in the molar ratio of at least 1:2, in the presence of a catalyst, at reaction temperatures between 120° C. and 270° C. Accordingly, the present invention also relates to a process for the preparation of oligocarbonates and polycarbonates, which is characterized in that ureas are reacted with primary dialcohols in the molar ratio of about 1.5:1 to about 1:1.5, together with monoalcohols, in the presence of catalysts at reaction temperatures between 120° C. and 270° C.