CA2020301A1 - Process for the preparation of an ester of a c -c -monocarboxylic acid - Google Patents
Process for the preparation of an ester of a c -c -monocarboxylic acidInfo
- Publication number
- CA2020301A1 CA2020301A1 CA002020301A CA2020301A CA2020301A1 CA 2020301 A1 CA2020301 A1 CA 2020301A1 CA 002020301 A CA002020301 A CA 002020301A CA 2020301 A CA2020301 A CA 2020301A CA 2020301 A1 CA2020301 A1 CA 2020301A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- ester
- monocarboxylic acid
- conductivity
- ppm
- 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.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
Abstract
Abstract:
Process for the preparation of an ester of a C22-C40-monocarboxylic acid Esterification of a C22-C40-monocarboxylic acid with alcohols in the presence of an acidic ion exchanger as the catalyst gives esters having a very low metal ion content, low conductivity and very good thermal and color stability.
Process for the preparation of an ester of a C22-C40-monocarboxylic acid Esterification of a C22-C40-monocarboxylic acid with alcohols in the presence of an acidic ion exchanger as the catalyst gives esters having a very low metal ion content, low conductivity and very good thermal and color stability.
Description
2~2~3~
HOECHST AKTIENGE5ELLSCHAFT HOE 89/F 211 ~r. DA/gm Description Process for the preparation of an ester of ~ C~-C~O-monocar~o~ylic acid ~he invention relates to a process for the preparation o~
an ester of a C22-C40-monocarboxylic acid having a low content of metal ions and low electrical conductivity.
Industrial pla8tic8, in particular tho~e based on poly-esters, polycarbonates, polyaryl ether sulfones or polyether ketones have particular resistance to mechan-ical and/or thermal stress. However, the functional groups which are pre~ent in these plastics are suscept-ible to degradation reactions. If degradation reactions occur, the mechanical and thermal propertie~ of the plastics are impaired~ Degradation reaction~ of thi~ type such as, for example, tran6es~erifica~ions, are promoted by metal ions and in particular hare by ~odium ions.
In many applications it i5 essenti l to suppress degrad=
ation reactions of this type and ~o the plastic molding compositions must contain only insignificant amounts of metal ionsO Lubricants and release agents for moldinq compositions of this type must likewi~e independently ~atisfy the hi~h purity requirement~.
The preparation of lubricant waxes by e~teri~ication of long-chain carboxylic acids with alcohol~ normally employs, as catalysts, protonic catalysts ~uch as H2SO4, p-toluenesulfonic acid, H3POzl or Zn compounds or Sn compounds. In this procednre, the cataly~t must be deactivated after the reaction~ The re~ulting salts either remain in the product or mu~t be ~eparated in a complex operation, for example by extraction or distillatio~.
, , : , .
20203~1 Although the use of ion exchangers as esterifica~ion catalysts in the non-aqueous medium has been disclos~d (cf. US-A-3,90,073), this use is limited to the prepar ation of low molecular weigh~, dissolved compound~.
The object of the invention is to provide an esterifi-cation process in which esters of long-~hain carboxylic acids having an extremely low metal ion content axs obtained in a single step.
It has been found that this objec~ can be achieved if the esterification cataly~t used is an acidic ion exchanger.
The present i~vention accordingly provides a process for the preparation of an ester of a C22-C40-monocarboxylic acid by esterification of the carboxylic acid with an alcohol in the presence of a catalyst, which comprises using an acid ion exchanger as the catalys~.
The process according to the invention employs a C22-C40-, premprises using a C24-C34-monocarboxylic acid. Examples of suitable acids are tetracosanoic acid, lignoceric acid, cerotic acid, montanic acid and melis~ic acid. Preference is given to montanic acid, in particular industri~l montanic acid which is a mixture of C2q-C34-monocarboxylic acids and is obtained by oxidation of crude montan wa~O
Most particular preference i8 given to an acid which h~s an acid number of above 120, a content of Na ions of below 10 ppm and a conductivity of le~s than 150 ~S.
Suitable alcohols for the process according to the invention are mono- and poly-hydr$c alcohols having 2 to 18 carbon atoms and 1 to 6 OH groups, preferably C2~C6-polyol~ having 2 to 6 OH group~. Alcohol~ of this type are lauryl alcohol, benzyl alcohol, 1,2-ethanediol, 1,4-butanediol, trimethylolpropane, pentaerythritol and glycerol. Among the~e alcohols, preference i8 given to the use of 1,2-ethanediol and trimethylolpropane.
.
2~20~
The es~erification ca~alyst is an acidic ion exchanger.
Suitable ion exchangers are ca~ion exchangers, which are commercially aYailable from a number of manufacturer~.
Particularly suitable are polytstyrenesulfonic acids), for example having a particle size of 0.1 to 2.0 mm. The ion exchanger is used in an amount from 2.0 to 0.1 % by weight, relative to the total batch.
The reaction is carried out in the melt at a temperature of 100 to 135, preferably 115 to 125DC. This reaction can be carried out under atmo~pheric pres~ure or under reduced pressure, and it i~ also pos~i~le to use an inert gas atmosphere. The reaction time is 1 to 10, preferably 3 to 7 hours. In this reaction, the ion exchanger func-tions not only as a cataly~t bu~ as an adsorbent for polar substances which impair the thermal stability.
After the e~terification, the ion exchanger is removed by filtration and freed from adhering products by wa~hing with a solvent, for example toluene or CH2C12. The ion exchanger can be then be reu~ed. Regeneration i~ only necessa~y after repeated use.
The esters which have been prepared by the process according to the invention have very good thermal stabil-ity, high color stability, a very low ion content and low conductivity.
The invention is further explained by means of the examples which follow.
The conductivity was determined by adding 100 cm3 of deionized wa~er to 10 g of wax and heating the mixture in a 300 cm3 Erlenmeyer flask for 10 minutes under reflux.
The agueous phase wa~ separated off and the pH of this phase and itB conductivity at room temperature were measured. A calibrated conductometer wa~ used for the measurement.
-: :
,. , , ~
.
~ ~2~3~1 ~:Kampl~
734 g (1.76 mol) of industrial montan wax acid (SZ 134) were melted and to this were added 65.2 g (1.05 mol) of 1,2-ethanediol and 4 g (0.5 % by weight) of an acidic ion exchanger ~poly(styrenesulfonic acid), particle size 0.3 to 1.2 ~m). Th~ batch was heated to 125C with stirring and kept at this tempera~ure, while distilling off the water of xeaction, until an aliquot of the wax had an acid number of below 25. Then the batch was flltered.
Na 5 ppm; conductivity 54 ~S.
E~ample 2:
The process of Example 1 was used to esterify industrial montan wax acid with glycerol. The components used were 917.6 g (2.2 mol) of montan wax acid, 92 g (1.0 mol) of glycerol and g (0.5 % by weight) of the acidic ion exchanger as in Example 1.
Acid number 23 Na 6 ppm; conductivity S9 ~S.
~xa~ple 3:
The process of Example 1 was used to esterify industrial montan wax acid with trimethylol propane. The components used were 917.6 g (2.2 mol) of montan wax acid, 134 g (1.0 mol) of trimethylolpropane and g (0.5 ~ by weight) of the acidic ion exchanger as in Example 1.
Acid number ~ 10 Na 4 ppm; conductivity 50 ~S.
- , .;
, ' . ', . ' ~
~203~
Comparative ~ample A:
Example l was repeated, but ins~ead of the ion exchanger, 0.8 g ~0.1 ~ by weight) of 50 % strength H3PO2 was used ax the catalyst. Before the batch was filtered, the catalyst was neutralized using 10 % strength NaOH.
Na 240 ppm; conductivity 153 ~5.
A portion of the product was melted and washed in the ratio of 1:5 with 5 % strength acetic acid. The aqueous phase was separated off and the wax pha6e washed a further 4 times with deionized water. The wax phase wa~
then dried in vacuo.
Na 5 ppm; conductivity 65 ~S.
Comparative E~ample B:
Example 2 was repeated but instead of the ion exchanger, 1.0 g (0.1 ~ by weight) of 44 % streng~h HzSO4 was used as catalyst. Before the batch was filtered, the catalyst was neutralized using 10 % strength NaOH.
Na 258 ppm; conductivity 143 ~S.
Washing the product as described in Comparative Ex~mple A
gave:
Na 9 ppm; conductivity 63 ~S.
Comparative RxE~ple C:
Example 3 was repeated but instead of the ion e~chang0r, 1~0 g (Ool % by weight) of 44 % strength ~I2SO4 was used a~
the catalyst. Before the batch was filtered, the catalyst was neutralized using 10 % strength NaOH.
Na 278 ppm; conductivity 157 ~S.
Washing the product as described in Comparative Example A
gave:
Na 7 ppm; conductivity 63 ~S.
i ..
202~
-- 6 _ ~ample 4:
Color stability of PVC formulations The test formulations which follow were used to carry out comparative color tests with glycerol montanate. ~he te~t mixtures were processed at 140~C and 15/20 rpm on a labora-tory mill to give milled hides. At interval~ of 5, 10 and 15 minutes, samples were taken from the mill and the yellow-ness index of these wa3 determined using a colorimeter.
Formulation 1 S-PVC (R 60) 100 parts Zn Stabilizer" 0.1 "
Ca Stearate 0.3 ~-Diketone stabilizerZ~ 0.3 Epoxidized soya bean oil 3.0 "
MBS impact modifier3~ 8.0 "
Process aid4) 1.0 "
Hydrogenated castor oil 1.0 Brightening agent 2.0 Glycerol montanate 1.2 Formulation 2 M-PVC (~ 57) 100 parts Dioctyltin glycolate 1.6 "
NBS impact modifier3~ 8.0 "
Process aid4) 1.2 Epoxidized ~oya bean oil 1.0 Glycerol monostearate 0.3 ~
Glycerol montanate 0.6 "
l) Organic zinc salt, di~solved a) Stearoyl-, palmitoyl-benzoylmethane 3) Crosslinked copolymer of methacrylates, butadiene and styrene 4) Copolymer of methyl methacrylate and ethyl acrylate ,. . ~ , ::
.
2~3~1 Color measurements on milled hides Color (YI) in Color (YI) in formulation 1 formulation 2 5 min 10 min 15 min 5 min 10 min 15 min Wax A ~ 18.2 25.2 68.1 9.5 13.4 16.5 Wax B - 14.6 29 70 9.7 15.2 20.2 Wax A = glycerol montanate according to Example 2 Wax B = glycerol montanate according to Comparative Example B
~xample 5:
Stability of polyester 0.25 part~ of ethylene glycol montanate were added to a commercially available polyester (RPolyclear T 86;
Hoechst). The proce~ing ~tability was determined by preparing 4 mm thick injection molded platelets from the test mixtures and the color and al~o the VICAT ~oftening points were determined on these platelets.
The processingstability under prolonged thermal stress was determined using residence time of the plastic composition in the injection-molding machine of 5, 10 and 15 minutes.
The in~ection-molding machine u~ed for the test~ was a Wind~or SP 50 type, the temperature profile of the in~ection unit being 260, 270, 290, 300C, and the temperature in the mold being 15C.
Wax Color (YI) VICAT softening point 5 min 10 min 15 min 5 min lO min 15 min None 9.0 14.9 19.5 76 75 75 Wax C 19.0 21.2 30.2 75.5 75 75 Wax D 17.2 19.8 27.5 76 75 75 Wax C = glycol montanate according to Comparative Example A
Wax D = glycol montanate according to Example 1 "~
- : , . , . . . : ~
- ;'
HOECHST AKTIENGE5ELLSCHAFT HOE 89/F 211 ~r. DA/gm Description Process for the preparation of an ester of ~ C~-C~O-monocar~o~ylic acid ~he invention relates to a process for the preparation o~
an ester of a C22-C40-monocarboxylic acid having a low content of metal ions and low electrical conductivity.
Industrial pla8tic8, in particular tho~e based on poly-esters, polycarbonates, polyaryl ether sulfones or polyether ketones have particular resistance to mechan-ical and/or thermal stress. However, the functional groups which are pre~ent in these plastics are suscept-ible to degradation reactions. If degradation reactions occur, the mechanical and thermal propertie~ of the plastics are impaired~ Degradation reaction~ of thi~ type such as, for example, tran6es~erifica~ions, are promoted by metal ions and in particular hare by ~odium ions.
In many applications it i5 essenti l to suppress degrad=
ation reactions of this type and ~o the plastic molding compositions must contain only insignificant amounts of metal ionsO Lubricants and release agents for moldinq compositions of this type must likewi~e independently ~atisfy the hi~h purity requirement~.
The preparation of lubricant waxes by e~teri~ication of long-chain carboxylic acids with alcohol~ normally employs, as catalysts, protonic catalysts ~uch as H2SO4, p-toluenesulfonic acid, H3POzl or Zn compounds or Sn compounds. In this procednre, the cataly~t must be deactivated after the reaction~ The re~ulting salts either remain in the product or mu~t be ~eparated in a complex operation, for example by extraction or distillatio~.
, , : , .
20203~1 Although the use of ion exchangers as esterifica~ion catalysts in the non-aqueous medium has been disclos~d (cf. US-A-3,90,073), this use is limited to the prepar ation of low molecular weigh~, dissolved compound~.
The object of the invention is to provide an esterifi-cation process in which esters of long-~hain carboxylic acids having an extremely low metal ion content axs obtained in a single step.
It has been found that this objec~ can be achieved if the esterification cataly~t used is an acidic ion exchanger.
The present i~vention accordingly provides a process for the preparation of an ester of a C22-C40-monocarboxylic acid by esterification of the carboxylic acid with an alcohol in the presence of a catalyst, which comprises using an acid ion exchanger as the catalys~.
The process according to the invention employs a C22-C40-, premprises using a C24-C34-monocarboxylic acid. Examples of suitable acids are tetracosanoic acid, lignoceric acid, cerotic acid, montanic acid and melis~ic acid. Preference is given to montanic acid, in particular industri~l montanic acid which is a mixture of C2q-C34-monocarboxylic acids and is obtained by oxidation of crude montan wa~O
Most particular preference i8 given to an acid which h~s an acid number of above 120, a content of Na ions of below 10 ppm and a conductivity of le~s than 150 ~S.
Suitable alcohols for the process according to the invention are mono- and poly-hydr$c alcohols having 2 to 18 carbon atoms and 1 to 6 OH groups, preferably C2~C6-polyol~ having 2 to 6 OH group~. Alcohol~ of this type are lauryl alcohol, benzyl alcohol, 1,2-ethanediol, 1,4-butanediol, trimethylolpropane, pentaerythritol and glycerol. Among the~e alcohols, preference i8 given to the use of 1,2-ethanediol and trimethylolpropane.
.
2~20~
The es~erification ca~alyst is an acidic ion exchanger.
Suitable ion exchangers are ca~ion exchangers, which are commercially aYailable from a number of manufacturer~.
Particularly suitable are polytstyrenesulfonic acids), for example having a particle size of 0.1 to 2.0 mm. The ion exchanger is used in an amount from 2.0 to 0.1 % by weight, relative to the total batch.
The reaction is carried out in the melt at a temperature of 100 to 135, preferably 115 to 125DC. This reaction can be carried out under atmo~pheric pres~ure or under reduced pressure, and it i~ also pos~i~le to use an inert gas atmosphere. The reaction time is 1 to 10, preferably 3 to 7 hours. In this reaction, the ion exchanger func-tions not only as a cataly~t bu~ as an adsorbent for polar substances which impair the thermal stability.
After the e~terification, the ion exchanger is removed by filtration and freed from adhering products by wa~hing with a solvent, for example toluene or CH2C12. The ion exchanger can be then be reu~ed. Regeneration i~ only necessa~y after repeated use.
The esters which have been prepared by the process according to the invention have very good thermal stabil-ity, high color stability, a very low ion content and low conductivity.
The invention is further explained by means of the examples which follow.
The conductivity was determined by adding 100 cm3 of deionized wa~er to 10 g of wax and heating the mixture in a 300 cm3 Erlenmeyer flask for 10 minutes under reflux.
The agueous phase wa~ separated off and the pH of this phase and itB conductivity at room temperature were measured. A calibrated conductometer wa~ used for the measurement.
-: :
,. , , ~
.
~ ~2~3~1 ~:Kampl~
734 g (1.76 mol) of industrial montan wax acid (SZ 134) were melted and to this were added 65.2 g (1.05 mol) of 1,2-ethanediol and 4 g (0.5 % by weight) of an acidic ion exchanger ~poly(styrenesulfonic acid), particle size 0.3 to 1.2 ~m). Th~ batch was heated to 125C with stirring and kept at this tempera~ure, while distilling off the water of xeaction, until an aliquot of the wax had an acid number of below 25. Then the batch was flltered.
Na 5 ppm; conductivity 54 ~S.
E~ample 2:
The process of Example 1 was used to esterify industrial montan wax acid with glycerol. The components used were 917.6 g (2.2 mol) of montan wax acid, 92 g (1.0 mol) of glycerol and g (0.5 % by weight) of the acidic ion exchanger as in Example 1.
Acid number 23 Na 6 ppm; conductivity S9 ~S.
~xa~ple 3:
The process of Example 1 was used to esterify industrial montan wax acid with trimethylol propane. The components used were 917.6 g (2.2 mol) of montan wax acid, 134 g (1.0 mol) of trimethylolpropane and g (0.5 ~ by weight) of the acidic ion exchanger as in Example 1.
Acid number ~ 10 Na 4 ppm; conductivity 50 ~S.
- , .;
, ' . ', . ' ~
~203~
Comparative ~ample A:
Example l was repeated, but ins~ead of the ion exchanger, 0.8 g ~0.1 ~ by weight) of 50 % strength H3PO2 was used ax the catalyst. Before the batch was filtered, the catalyst was neutralized using 10 % strength NaOH.
Na 240 ppm; conductivity 153 ~5.
A portion of the product was melted and washed in the ratio of 1:5 with 5 % strength acetic acid. The aqueous phase was separated off and the wax pha6e washed a further 4 times with deionized water. The wax phase wa~
then dried in vacuo.
Na 5 ppm; conductivity 65 ~S.
Comparative E~ample B:
Example 2 was repeated but instead of the ion exchanger, 1.0 g (0.1 ~ by weight) of 44 % streng~h HzSO4 was used as catalyst. Before the batch was filtered, the catalyst was neutralized using 10 % strength NaOH.
Na 258 ppm; conductivity 143 ~S.
Washing the product as described in Comparative Ex~mple A
gave:
Na 9 ppm; conductivity 63 ~S.
Comparative RxE~ple C:
Example 3 was repeated but instead of the ion e~chang0r, 1~0 g (Ool % by weight) of 44 % strength ~I2SO4 was used a~
the catalyst. Before the batch was filtered, the catalyst was neutralized using 10 % strength NaOH.
Na 278 ppm; conductivity 157 ~S.
Washing the product as described in Comparative Example A
gave:
Na 7 ppm; conductivity 63 ~S.
i ..
202~
-- 6 _ ~ample 4:
Color stability of PVC formulations The test formulations which follow were used to carry out comparative color tests with glycerol montanate. ~he te~t mixtures were processed at 140~C and 15/20 rpm on a labora-tory mill to give milled hides. At interval~ of 5, 10 and 15 minutes, samples were taken from the mill and the yellow-ness index of these wa3 determined using a colorimeter.
Formulation 1 S-PVC (R 60) 100 parts Zn Stabilizer" 0.1 "
Ca Stearate 0.3 ~-Diketone stabilizerZ~ 0.3 Epoxidized soya bean oil 3.0 "
MBS impact modifier3~ 8.0 "
Process aid4) 1.0 "
Hydrogenated castor oil 1.0 Brightening agent 2.0 Glycerol montanate 1.2 Formulation 2 M-PVC (~ 57) 100 parts Dioctyltin glycolate 1.6 "
NBS impact modifier3~ 8.0 "
Process aid4) 1.2 Epoxidized ~oya bean oil 1.0 Glycerol monostearate 0.3 ~
Glycerol montanate 0.6 "
l) Organic zinc salt, di~solved a) Stearoyl-, palmitoyl-benzoylmethane 3) Crosslinked copolymer of methacrylates, butadiene and styrene 4) Copolymer of methyl methacrylate and ethyl acrylate ,. . ~ , ::
.
2~3~1 Color measurements on milled hides Color (YI) in Color (YI) in formulation 1 formulation 2 5 min 10 min 15 min 5 min 10 min 15 min Wax A ~ 18.2 25.2 68.1 9.5 13.4 16.5 Wax B - 14.6 29 70 9.7 15.2 20.2 Wax A = glycerol montanate according to Example 2 Wax B = glycerol montanate according to Comparative Example B
~xample 5:
Stability of polyester 0.25 part~ of ethylene glycol montanate were added to a commercially available polyester (RPolyclear T 86;
Hoechst). The proce~ing ~tability was determined by preparing 4 mm thick injection molded platelets from the test mixtures and the color and al~o the VICAT ~oftening points were determined on these platelets.
The processingstability under prolonged thermal stress was determined using residence time of the plastic composition in the injection-molding machine of 5, 10 and 15 minutes.
The in~ection-molding machine u~ed for the test~ was a Wind~or SP 50 type, the temperature profile of the in~ection unit being 260, 270, 290, 300C, and the temperature in the mold being 15C.
Wax Color (YI) VICAT softening point 5 min 10 min 15 min 5 min lO min 15 min None 9.0 14.9 19.5 76 75 75 Wax C 19.0 21.2 30.2 75.5 75 75 Wax D 17.2 19.8 27.5 76 75 75 Wax C = glycol montanate according to Comparative Example A
Wax D = glycol montanate according to Example 1 "~
- : , . , . . . : ~
- ;'
Claims (8)
1. A process for the preparation of an ester of a C22-C40-monocarboxylic acid by esterification of the carboxylic acid with an alcohol in the presence of a catalyst, which comprises using an acidic ion exchanger as the catalyst.
2. The process as claimed in claim 1, wherein the C22-C40-monocarboxylic acid is montanic acid which has been obtained from montan waxes.
3. The process as claimed in claim 1, wherein the mon-tanic acid used has an acid number of above 120, a content of Na ions below 10 ppm and a conductivity of less than 150 µS.
4. The process as claimed in claim 1, wherein the alcohol component used is a C2-C6-polyol having a 2 to 6 OH
groups.
groups.
5. An ester of an C22-C40-monocarboxylic acid having an alkali metal content of below 10 ppm and a conductivity of less than 70 µS, prepared by the process as claimed is claim 1.
6. The use of the esters which have been prepared as claimed in claim 1 as an auxiliary in the processing of plastic molding compositions which are essentially composed of polycarbonates, polyesters, polyphenylene sulfide or polyphenylene oxide.
7. A plastic molding composition which is essentially composed of polycarbonate, polyesters, polyphenylene sulfide or polyphenylene oxide, and contains 0.01-5 % by weight of an ester which has been prepared as claimed in claim 1.
8. The process as claimed in claim 1 and substantially as described herein.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3921917A DE3921917A1 (en) | 1989-07-04 | 1989-07-04 | METHOD FOR PRODUCING THE ESTER OF A C (DOWN ARROW) 2 (DOWN ARROW) (DOWN ARROW) 2 (DOWN ARROW) -C (DOWN ARROW) 4 (DOWN ARROW) (DOWN ARROW) - 0 (DOWN ARROW) MONTH |
| DEP3921917.8 | 1989-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2020301A1 true CA2020301A1 (en) | 1991-01-05 |
Family
ID=6384245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002020301A Abandoned CA2020301A1 (en) | 1989-07-04 | 1990-07-03 | Process for the preparation of an ester of a c -c -monocarboxylic acid |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0406767B1 (en) |
| JP (1) | JP2966484B2 (en) |
| KR (1) | KR910002762A (en) |
| AT (1) | ATE111436T1 (en) |
| AU (1) | AU630208B2 (en) |
| CA (1) | CA2020301A1 (en) |
| DE (2) | DE3921917A1 (en) |
| ES (1) | ES2063865T3 (en) |
| HK (1) | HK1007134A1 (en) |
| ZA (1) | ZA905188B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6310227B1 (en) | 1997-01-31 | 2001-10-30 | The Procter & Gamble Co. | Reduced calorie cooking and frying oils having improved hydrolytic stability, and process for preparing |
| US8304478B2 (en) | 2010-07-30 | 2012-11-06 | Sabic Innovative Plastics Ip B.V. | Polyamide/poly(arylene ether) composition, article, and method |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2062928B1 (en) * | 1992-12-17 | 1995-07-16 | Consejo Superior Investigacion | PROCEDURE FOR THE SELECTIVE OBTAINING OF MONOLESTERS OF DIOLES AND TRIOLS USING ZEOLITICAL CATALYSTS. |
| AU738499B2 (en) * | 1997-01-31 | 2001-09-20 | Procter & Gamble Company, The | Reduced calorie cooking and frying oils having improved hydrolytic stability, and process for preparing |
| AU7606700A (en) * | 1999-09-27 | 2001-04-30 | Eastman Chemical Company | Polyester-wax compositions and methods of making the same |
| WO2020032271A1 (en) * | 2018-08-10 | 2020-02-13 | 国立大学法人東北大学 | Production method for polyvalent alcohol ester compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3590073A (en) * | 1967-12-15 | 1971-06-29 | Atlantic Richfield Co | Esterification of tertiary alcohols |
| GB1461597A (en) * | 1973-05-15 | 1977-01-13 | Ucb Sa | Unsaturated compounds and compositions containing them |
| BR8008845A (en) * | 1979-09-27 | 1981-07-21 | Union Carbide Corp | USE OF PERFLUOROSULPHONIC ACID RESINS AS CATALYSTS TO PREPARE ESTERS |
| US4332738A (en) * | 1980-11-24 | 1982-06-01 | Exxon Research & Engineering Co. | Esterification of neo acids by the use of cation exchange resins |
| DE3734138A1 (en) * | 1987-10-09 | 1989-04-20 | Scharmer Klaus Dr Ing | ACID CATALYST AND METHOD FOR PRODUCING THE CATALYST |
-
1989
- 1989-07-04 DE DE3921917A patent/DE3921917A1/en not_active Withdrawn
-
1990
- 1990-07-02 DE DE59007110T patent/DE59007110D1/en not_active Expired - Fee Related
- 1990-07-02 AT AT90112599T patent/ATE111436T1/en not_active IP Right Cessation
- 1990-07-02 ES ES90112599T patent/ES2063865T3/en not_active Expired - Lifetime
- 1990-07-02 EP EP90112599A patent/EP0406767B1/en not_active Expired - Lifetime
- 1990-07-03 JP JP2174635A patent/JP2966484B2/en not_active Expired - Lifetime
- 1990-07-03 CA CA002020301A patent/CA2020301A1/en not_active Abandoned
- 1990-07-03 ZA ZA905188A patent/ZA905188B/en unknown
- 1990-07-03 AU AU58621/90A patent/AU630208B2/en not_active Ceased
- 1990-07-03 KR KR1019900009987A patent/KR910002762A/en active IP Right Grant
-
1998
- 1998-06-24 HK HK98106333A patent/HK1007134A1/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6310227B1 (en) | 1997-01-31 | 2001-10-30 | The Procter & Gamble Co. | Reduced calorie cooking and frying oils having improved hydrolytic stability, and process for preparing |
| US8304478B2 (en) | 2010-07-30 | 2012-11-06 | Sabic Innovative Plastics Ip B.V. | Polyamide/poly(arylene ether) composition, article, and method |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA905188B (en) | 1991-04-24 |
| AU630208B2 (en) | 1992-10-22 |
| DE59007110D1 (en) | 1994-10-20 |
| ES2063865T3 (en) | 1995-01-16 |
| EP0406767A2 (en) | 1991-01-09 |
| DE3921917A1 (en) | 1991-01-17 |
| JP2966484B2 (en) | 1999-10-25 |
| HK1007134A1 (en) | 1999-04-01 |
| KR910002762A (en) | 1991-02-26 |
| EP0406767A3 (en) | 1991-10-23 |
| AU5862190A (en) | 1991-01-10 |
| JPH0344350A (en) | 1991-02-26 |
| ATE111436T1 (en) | 1994-09-15 |
| EP0406767B1 (en) | 1994-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |