CA1054628A - Esterification process - Google Patents
Esterification processInfo
- Publication number
- CA1054628A CA1054628A CA230857A CA230857A CA1054628A CA 1054628 A CA1054628 A CA 1054628A CA 230857 A CA230857 A CA 230857A CA 230857 A CA230857 A CA 230857A CA 1054628 A CA1054628 A CA 1054628A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- trimethyl
- titanate
- ammonium salt
- dodecadienoic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Abstract of the Disclosure Esters of fatty acids are prepared in high yield by reacting a tetraalkyl titanate with a fatty acid or the ammonium salt thereof.
Description
`
This invention relates to a novel process for preparing ~ -fatty acid esters in high yield by the reaction of a tetraalkyl titanate with a fatty acid or the ammonium salt thereof. -~
The process of this invention provides a convenient and economical, one-step process for preparing fatty acid esters in ~
high yield. In carrying out the reaction, a fatty acid of the ~;
formula R-~-OH or the ammonium salt thereof is reacted with a t~traalkyl titanate of the formula (R'o)4Ti, wherein R is a group selected from the class consisting of aliphatic hydrocarbon groups and substituted aliphatic hydrocarbon groups with one or ~ -~
more alkoxy groups. Each of the aliphatic hydrocarbon groups has a carbon atom chainlength of at least five car~on atoms. R' is lower alkylO This reaction is particularly advantageous for preparing esters of con~ugated unsaturated esters which are often difficult to obtain by alternate routes.
3 In order to obtain maximum yields, there must be ~3~ ~
present at least 0.75 mole of titanatle per mole of fatty acid i - or ammonium salt thereof. While no limit need be set on the ~;~
excess of titanate that can be present, as a practical matter, 20~ no advantage is derived ~rom greater than a two-fold molar excess of titanate to acid. Pre~erably 0.75 to 1.5 molar equivalents of titana~e per mole o~ acid is employed, more preferably 0~9 to ~ 1.5 molar equivalents o~ titanate per mole o~ acid. Ordinarily, `~
`~ only 0.75 molar e~uivalents of tetraalkyl titanate are consumed in the reaction. Excess titanate may be recovered at the end of ~ `
~ the reaction by distillation.
j While the acid may be diluted with solvent inert to the reaction, such as hexane, it is preferred that the reaction be carried out in the absence of any solvent to simplify recovery.
,~ ,, .
'~. ~" '' '' ` ,,'. ' ~,-i ~ O~ ~ 2 The reaction is carried out at a temperature of from about 110 to 200C, prcferably 130 to 185C. The reaction is ordinarily complete in about 1 to 2 hours. Lower reaction temperatures can be used but as a consequence, longer reaction time is required.
During the initial phase of the reaction, any by-product alcohol from the tetraalkyl titanate (along with any solvent initially present~ is removed by distillation. If the ammonium salt o the acid is being employed, ammonia is a]so evolved and removed at this stage.
After completion of the reaction, residual tetraalkyl -titanate ester may be recovered by distillation under vacuum ~ ~-or residual organotitanates can be removed by diluting with a , solvent inert to the ester, such as hexane, pentane, benzene, xylene, and the lik.e, and adding a small amount of water and a base such as calcium oxide or sodium hydroxide. The resultant precipitate of hydrated titanium oxide lS removed by filtration.
'~ Alternatively, the reaction mixture in hexane can be extracted ï ~with a large excess of aqueous acid, such as 8N sulfuric acid, ;~
followed by an aqueous solution of a titanium (IV) complexing J~ agent, such as 5% aqueous hydroxyacetic acid followed by aqueous base, such as 2N aqueous sodium hydroxide.
As used herein, the term "aliphatic hydrocarbon group"
refers to a straight or branched chain alkyl, alkenyl or alkynyl `~
group, optionally substituted by one or more lower alkoxy groups, containing from five to thirty carbon atoms and having a chain-length of at least five carbon atoms.
The term "lower alkyl" refers to a saturated aliphatic - hydrocarbon ~roup of one to six carbon atoms, e.g. methyl, ethyl, ; propvl, i50propyl, butyl, and the like.
:', ' ` ' .
,, , ~-, .
3 ~
~ , . . . . .
~ ~5 Typical fcltty acids contcmplated or usc in the process o this invention include the following: sorbic acid, lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, parinaric acid, erythrogenic acid, 3,7 7 11 - trimethyldodeca-2,4- `:
dienoic acid, ll-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid, ll-ethoxy-3,7,11-trimethyldodeca-2,4-dienoic acid, and the amrnonium salts thereof.
The following examples illustrate the process of this invention. Temperature l5 glven in degrees Centigrade.
., , ~-, '` ' '' ;' :.' ' ' - ' ` :'". . . . :.
,, . , ; . .
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To 143 g. (0.5 mole) of the ammonium salt of (2E,4E)-ll-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid (containing a small amount of 2Z,4E isomer~ under nitrogen is added ]48 ml.
(0.5 mole) of tetraisopropyl titanate. The mixture is heated ; to 150. As the temperature rises, the ammonium salt dissolves with evolution of ammonia and isopropyl alcohol distills from the solution. The reaction mixture is allowed to stand at 150-155 for 1.5 hours. The temperature is then lowered to 100 and residual tetraisopropyl titanate (33.4 g.) is recovered by dis-tillation at 0.3 mm. The residual liquid is cooled to 25 and diluted with 500 ml. hexane. 20 Grams of calcium oxide is added, followed by 30 ml~ of water. The resultant slurry is stirred for 3 hours and then the product is separated by filtration to give 144.4 g. of isopropyl t2E,4E)-ll-methoxy-3,7,11-trimethyl-274-dodecadlenoate (containing a small amount of 2Z,4~) as a pale yellow oil in 93% yield, b.p. ~bath) 90 ~0.010 mm.).
¦ EXAMPLE 2 :, A mixture of ll-methoxy-3,7,11-trimethyl-2,4-dodecadie-noic acid (34.95 g-), mostly 2E,4E isomer and tetraisopropyl ~titanate (39 ml.) is heated under an atomsphere of nitrogen to , ~ . .
90. Volatile material is removed by distillation at a pressure of 100 mm. and a pot temperature of 90 to 130. The distillate, `~
which consists mostly of isopropyl alcohol, amounts to 9 ml. The `~
residue is then heated under an atmosphere of nitrogen to 150 and is held at 145 to 155 for l.S hours. The mixture is ~, . .
cooled to about 100 and residual tetraisopropyl titanate is recovered by distillation at 3 mm. and a pot temperature of 100 to 150. This operation, which requires about 15 minutes, gives .
, ' . ' i -5- ~
.. . . . ..
.
.. . . .
8 ~-9.5 ml. of recovered tetraisopropyl titanate. The residual liquid is cooled to room temperature, diluted with hexane, and extracted for 10 minutes with 4~ ml. of 8N sulfuric acid. The hexane phase is separated and washed successively with 5~ aqueo~s hydroxyacetic acid, 2N aqueous sodium hydroxide, and water. Each ~ -aqueous phase is back-extracted with hexane. The hexane solutions . .
are combined and solvent is removed under vacuum to give isopropyl ~ - methoxy-3,7,11-trimethyl-2,4-dodecadienoate in 97~ yield as a pale amber liquid, mostly trans,trans.
'~ A mixture of 3,7,11-trimethyl-2,4-dodecadienoic acid (5.95 g., 0.025 mole), mostly 2E,4E isomer, and tetramethyl titanate (6.45 g., 0.0375 mole) is heated to 70 with stirring 1 under an atomsphere of nitrogen. After most of the solid has : .
dissolved, the vessel is evacuated to 100 mm. pressure and methanol lS removed by distillation. The mixture is heated to 140 w1th stirring under vacuum~ then nitrogen is introduced and the temperature is raised to 165. After three hours at 160 to 165, the r.eact~ion mixture is cooled to about 25~ and diluted with 15 ml. of hexane. The resul~ing solution is stirred vi~orously with 18 ml. of 8N suIfuric acid for 30 minutes. The organic;phase is separated, filtered, and washed -~
successively with 5% aqueous hydroxyacetic acid, lN aqueous sodium hydr~oxide, and water. Solvent is removed by evaporation under vacuum to give 5.74 g. of methyl 3,7,11-trimethyl-2,4- t !~', ' ,~,'' dodecadienoate in 90~ yield as a pale yellow liquid, mostly 2E,4E isomer, b.p. ~bath) 95 (0.3 mm.).
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. ~ . . . .
~ :, .~ - .
-6- - :
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~ ~5~
EX~MPIE 4 A mixture o~ the ammoniwn salt of 3,7,11-trimethyl-
This invention relates to a novel process for preparing ~ -fatty acid esters in high yield by the reaction of a tetraalkyl titanate with a fatty acid or the ammonium salt thereof. -~
The process of this invention provides a convenient and economical, one-step process for preparing fatty acid esters in ~
high yield. In carrying out the reaction, a fatty acid of the ~;
formula R-~-OH or the ammonium salt thereof is reacted with a t~traalkyl titanate of the formula (R'o)4Ti, wherein R is a group selected from the class consisting of aliphatic hydrocarbon groups and substituted aliphatic hydrocarbon groups with one or ~ -~
more alkoxy groups. Each of the aliphatic hydrocarbon groups has a carbon atom chainlength of at least five car~on atoms. R' is lower alkylO This reaction is particularly advantageous for preparing esters of con~ugated unsaturated esters which are often difficult to obtain by alternate routes.
3 In order to obtain maximum yields, there must be ~3~ ~
present at least 0.75 mole of titanatle per mole of fatty acid i - or ammonium salt thereof. While no limit need be set on the ~;~
excess of titanate that can be present, as a practical matter, 20~ no advantage is derived ~rom greater than a two-fold molar excess of titanate to acid. Pre~erably 0.75 to 1.5 molar equivalents of titana~e per mole o~ acid is employed, more preferably 0~9 to ~ 1.5 molar equivalents o~ titanate per mole o~ acid. Ordinarily, `~
`~ only 0.75 molar e~uivalents of tetraalkyl titanate are consumed in the reaction. Excess titanate may be recovered at the end of ~ `
~ the reaction by distillation.
j While the acid may be diluted with solvent inert to the reaction, such as hexane, it is preferred that the reaction be carried out in the absence of any solvent to simplify recovery.
,~ ,, .
'~. ~" '' '' ` ,,'. ' ~,-i ~ O~ ~ 2 The reaction is carried out at a temperature of from about 110 to 200C, prcferably 130 to 185C. The reaction is ordinarily complete in about 1 to 2 hours. Lower reaction temperatures can be used but as a consequence, longer reaction time is required.
During the initial phase of the reaction, any by-product alcohol from the tetraalkyl titanate (along with any solvent initially present~ is removed by distillation. If the ammonium salt o the acid is being employed, ammonia is a]so evolved and removed at this stage.
After completion of the reaction, residual tetraalkyl -titanate ester may be recovered by distillation under vacuum ~ ~-or residual organotitanates can be removed by diluting with a , solvent inert to the ester, such as hexane, pentane, benzene, xylene, and the lik.e, and adding a small amount of water and a base such as calcium oxide or sodium hydroxide. The resultant precipitate of hydrated titanium oxide lS removed by filtration.
'~ Alternatively, the reaction mixture in hexane can be extracted ï ~with a large excess of aqueous acid, such as 8N sulfuric acid, ;~
followed by an aqueous solution of a titanium (IV) complexing J~ agent, such as 5% aqueous hydroxyacetic acid followed by aqueous base, such as 2N aqueous sodium hydroxide.
As used herein, the term "aliphatic hydrocarbon group"
refers to a straight or branched chain alkyl, alkenyl or alkynyl `~
group, optionally substituted by one or more lower alkoxy groups, containing from five to thirty carbon atoms and having a chain-length of at least five carbon atoms.
The term "lower alkyl" refers to a saturated aliphatic - hydrocarbon ~roup of one to six carbon atoms, e.g. methyl, ethyl, ; propvl, i50propyl, butyl, and the like.
:', ' ` ' .
,, , ~-, .
3 ~
~ , . . . . .
~ ~5 Typical fcltty acids contcmplated or usc in the process o this invention include the following: sorbic acid, lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, parinaric acid, erythrogenic acid, 3,7 7 11 - trimethyldodeca-2,4- `:
dienoic acid, ll-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid, ll-ethoxy-3,7,11-trimethyldodeca-2,4-dienoic acid, and the amrnonium salts thereof.
The following examples illustrate the process of this invention. Temperature l5 glven in degrees Centigrade.
., , ~-, '` ' '' ;' :.' ' ' - ' ` :'". . . . :.
,, . , ; . .
'' ., -.:
! ~
: -:! ` . ~:
.:j . ' ,-~' ' ' ''l , ''' ''' " ' - - : ~, ~.~5 . , ., . ~
1 ~.- .
',, 'i''; : ' ' '' ' ' ~ : '` : ' ' , ' ' , ' ` ,.:
J - 4- ~ ~
:
.. . .
46 ~
To 143 g. (0.5 mole) of the ammonium salt of (2E,4E)-ll-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid (containing a small amount of 2Z,4E isomer~ under nitrogen is added ]48 ml.
(0.5 mole) of tetraisopropyl titanate. The mixture is heated ; to 150. As the temperature rises, the ammonium salt dissolves with evolution of ammonia and isopropyl alcohol distills from the solution. The reaction mixture is allowed to stand at 150-155 for 1.5 hours. The temperature is then lowered to 100 and residual tetraisopropyl titanate (33.4 g.) is recovered by dis-tillation at 0.3 mm. The residual liquid is cooled to 25 and diluted with 500 ml. hexane. 20 Grams of calcium oxide is added, followed by 30 ml~ of water. The resultant slurry is stirred for 3 hours and then the product is separated by filtration to give 144.4 g. of isopropyl t2E,4E)-ll-methoxy-3,7,11-trimethyl-274-dodecadlenoate (containing a small amount of 2Z,4~) as a pale yellow oil in 93% yield, b.p. ~bath) 90 ~0.010 mm.).
¦ EXAMPLE 2 :, A mixture of ll-methoxy-3,7,11-trimethyl-2,4-dodecadie-noic acid (34.95 g-), mostly 2E,4E isomer and tetraisopropyl ~titanate (39 ml.) is heated under an atomsphere of nitrogen to , ~ . .
90. Volatile material is removed by distillation at a pressure of 100 mm. and a pot temperature of 90 to 130. The distillate, `~
which consists mostly of isopropyl alcohol, amounts to 9 ml. The `~
residue is then heated under an atmosphere of nitrogen to 150 and is held at 145 to 155 for l.S hours. The mixture is ~, . .
cooled to about 100 and residual tetraisopropyl titanate is recovered by distillation at 3 mm. and a pot temperature of 100 to 150. This operation, which requires about 15 minutes, gives .
, ' . ' i -5- ~
.. . . . ..
.
.. . . .
8 ~-9.5 ml. of recovered tetraisopropyl titanate. The residual liquid is cooled to room temperature, diluted with hexane, and extracted for 10 minutes with 4~ ml. of 8N sulfuric acid. The hexane phase is separated and washed successively with 5~ aqueo~s hydroxyacetic acid, 2N aqueous sodium hydroxide, and water. Each ~ -aqueous phase is back-extracted with hexane. The hexane solutions . .
are combined and solvent is removed under vacuum to give isopropyl ~ - methoxy-3,7,11-trimethyl-2,4-dodecadienoate in 97~ yield as a pale amber liquid, mostly trans,trans.
'~ A mixture of 3,7,11-trimethyl-2,4-dodecadienoic acid (5.95 g., 0.025 mole), mostly 2E,4E isomer, and tetramethyl titanate (6.45 g., 0.0375 mole) is heated to 70 with stirring 1 under an atomsphere of nitrogen. After most of the solid has : .
dissolved, the vessel is evacuated to 100 mm. pressure and methanol lS removed by distillation. The mixture is heated to 140 w1th stirring under vacuum~ then nitrogen is introduced and the temperature is raised to 165. After three hours at 160 to 165, the r.eact~ion mixture is cooled to about 25~ and diluted with 15 ml. of hexane. The resul~ing solution is stirred vi~orously with 18 ml. of 8N suIfuric acid for 30 minutes. The organic;phase is separated, filtered, and washed -~
successively with 5% aqueous hydroxyacetic acid, lN aqueous sodium hydr~oxide, and water. Solvent is removed by evaporation under vacuum to give 5.74 g. of methyl 3,7,11-trimethyl-2,4- t !~', ' ,~,'' dodecadienoate in 90~ yield as a pale yellow liquid, mostly 2E,4E isomer, b.p. ~bath) 95 (0.3 mm.).
;'l ' . , ' '~,~
. ~ . . . .
~ :, .~ - .
-6- - :
'' . ~:, , .
~ ~5~
EX~MPIE 4 A mixture o~ the ammoniwn salt of 3,7,11-trimethyl-
2,4-dodecadicnoic acid (20.4 g., 0.080 mole), mostly 2~,4F isomer, and tetraethyltitanate (25 ml., 0.12 mole) is heated under an -atmosphere of nitrogen to 80. The system is evacuated to a pressure of 100 mm., causing ethanol and ammonia to evaporate from the reaction mixture. The temperature is raised to 130 and nitrogen is admitted to the vessel. The reaction mixture is held at 150 to 155 for two hours, then is cooled to about 25, diluted with 50 ml. of hexane and extracted with 60 ml.
of 8N sulfuric acid by vigorous stirring over a period of 30 minutes. lhe organic phase is separated and washed successively with 5% aqueous hydroxyacetic acid, lN aqueous sodium hydroxide, and water. Solvent is removed by evaporation under vacuum to ;
give 19.73 g. of ethyl 3,7,11-trimethyl-2,4-dodecadienoate as an amber liquid in 93% yield, mostly 2E,4E isomer, b.p. (bath) 95 t0.03 mm.).
. ! . , ','; ' ' ` :
5~ EXAMPLE 5 The process of Example 2 is repeated using ll-ethoxy-l ~ ~ 3,7,11-trimethyl-2,4-dodecadienoic acid, mostly trans,trans and -; tetraethyltitanate to give ethy1 11-ethoxy-3,7,11-trimethyl-2,4-dodecadienoate, mostly trans, trans, b.p. (bath) 120 (0.5 mm.).
: .;: .
:1 . . . .. ~ : -- ' ' ~: .
. ~ .
:;, . .
.
,, ' .
,'. ' ': -, . : , ~............. ., : ,, .
..
,............. ~ .. . .
of 8N sulfuric acid by vigorous stirring over a period of 30 minutes. lhe organic phase is separated and washed successively with 5% aqueous hydroxyacetic acid, lN aqueous sodium hydroxide, and water. Solvent is removed by evaporation under vacuum to ;
give 19.73 g. of ethyl 3,7,11-trimethyl-2,4-dodecadienoate as an amber liquid in 93% yield, mostly 2E,4E isomer, b.p. (bath) 95 t0.03 mm.).
. ! . , ','; ' ' ` :
5~ EXAMPLE 5 The process of Example 2 is repeated using ll-ethoxy-l ~ ~ 3,7,11-trimethyl-2,4-dodecadienoic acid, mostly trans,trans and -; tetraethyltitanate to give ethy1 11-ethoxy-3,7,11-trimethyl-2,4-dodecadienoate, mostly trans, trans, b.p. (bath) 120 (0.5 mm.).
: .;: .
:1 . . . .. ~ : -- ' ' ~: .
. ~ .
:;, . .
.
,, ' .
,'. ' ': -, . : , ~............. ., : ,, .
..
,............. ~ .. . .
Claims (7)
1. A process for the preparation of fatty acid esters of the formula R-?-OR' wherein R is a group selected from the class consisting of aliphatic hydrocarbon groups and substituted ali-phatic hydrocarbon groups with one or more alkoxy groups, each of said aliphatic hydrocarbon groups having a carbon atom chain-length of at least five carbon atoms and R' is lower alkyl which comprises, reacting a fatty acid of the formula R-?-OR or the ammonium salt thereof with a titanate of the formula (R'O)4Ti, at a temperature of 110° to 200°C, there being present at least 0.75 mole of titanate per mole of fatty acid or ammonium salt thereof.
2. The process according to Claim 1 wherein the molar ratio of fatty acid or ammonium salt thereof to titanate is from 1.000.75 to 1.0:1.5.
3. The process according to Claim 2 wherein R' is lower alkyl of one to three carbon atoms and the acid is a conjugated unsaturated acid or the ammonium salt thereof.
4. The process according to Claim 3 wherein the fatty acid is 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid, 11-ethoxy-3,7,11-trimethyl-2,4-dodecadienoic acid or 3,7,11-trimethy1-2,4-dodecadienoic acid, said acids having mostly 2E,4E isomerism.
5. The process according to Claim 4 wherein R' is isopropyl and the fatty acid is 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid, mostly the 2E,4E isomer.
6. The process according to Claim 1 wherein there is reacted the ammonium salt of (2E,4E) 11-methoxy-3,7,11-tri-methyl-2,4-dodecadienoic acid with said titanate wherein R' is isopropyl to yield isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate, said acid and said ester containing a small amount of 2Z,4E isomer.
7. The process according to Claim 3 wherein the titanate is reacted with the ammonium salt of 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid, 11-ethoxy-3,7,11-trimethyl-2,4-dodecadienoic acid or 3,7,11-trimethyl-2,4-dodecadienoic acid, said acid having mostly 2E,4E isomerism.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA230857A CA1054628A (en) | 1975-07-04 | 1975-07-04 | Esterification process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA230857A CA1054628A (en) | 1975-07-04 | 1975-07-04 | Esterification process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054628A true CA1054628A (en) | 1979-05-15 |
Family
ID=4103541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230857A Expired CA1054628A (en) | 1975-07-04 | 1975-07-04 | Esterification process |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1054628A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241588A (en) * | 2011-04-29 | 2011-11-16 | 常州胜杰化工有限公司 | Preparation method for (2Z,4E)11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester |
| CN102267907A (en) * | 2011-06-07 | 2011-12-07 | 湖南中烟工业有限责任公司 | Preparation method for (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester |
-
1975
- 1975-07-04 CA CA230857A patent/CA1054628A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241588A (en) * | 2011-04-29 | 2011-11-16 | 常州胜杰化工有限公司 | Preparation method for (2Z,4E)11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester |
| CN102241588B (en) * | 2011-04-29 | 2013-05-29 | 常州胜杰化工有限公司 | Preparation method for (2Z,4E)11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester |
| CN102267907A (en) * | 2011-06-07 | 2011-12-07 | 湖南中烟工业有限责任公司 | Preparation method for (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester |
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