US2729660A - Phosphite esters as esterification catalysts - Google Patents
Phosphite esters as esterification catalysts Download PDFInfo
- Publication number
- US2729660A US2729660A US332555A US33255553A US2729660A US 2729660 A US2729660 A US 2729660A US 332555 A US332555 A US 332555A US 33255553 A US33255553 A US 33255553A US 2729660 A US2729660 A US 2729660A
- Authority
- US
- United States
- Prior art keywords
- esterification
- acid
- acids
- rosin
- esters
- 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 - Lifetime
Links
- 150000008301 phosphite esters Chemical class 0.000 title claims description 4
- 230000032050 esterification Effects 0.000 title description 19
- 238000005886 esterification reaction Methods 0.000 title description 19
- 239000003054 catalyst Substances 0.000 title description 14
- 239000002253 acid Substances 0.000 claims description 22
- 150000007513 acids Chemical class 0.000 claims description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 13
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Chemical class O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 13
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical class OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- -1 aliphatic alcohols Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 239000003784 tall oil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000000061 acid fraction Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HDIBKVVPMJKRGL-UHFFFAOYSA-N bis(2-ethylhexyl) hydrogen phosphite Chemical compound CCCCC(CC)COP(O)OCC(CC)CCCC HDIBKVVPMJKRGL-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- ICVIFRMLTBUBGF-UHFFFAOYSA-N 2,2,6,6-tetrakis(hydroxymethyl)cyclohexan-1-ol Chemical compound OCC1(CO)CCCC(CO)(CO)C1O ICVIFRMLTBUBGF-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
Definitions
- the present invention relates to a process of esterification in which esters of phosphorous acid are employed as esterification catalysts.
- the invention is applicable to the esterification of fatty acids or rosin acids with aliphatic alcohols, either monohydric or polyhydric.
- These catalysts can be used without causing appreciable color formation during the esterification, which is particularly troublesome with conventional catalysts, especially when unsaturated higher fatty acids are esterified.
- Common esterification catalysts such as strong acids cause darkening of the product during esterification.
- acid catalysts are difficult to remove.
- the phosphorous esters of the present invention are volatile, and can be removed easily by vacuum distillation at the end of the reaction.
- the esters which are obtained according to the present invention may have a very low free hydroxyl content, depending upon the extent to which it is desired to carry the esterification.
- the invention is applicable to the esterification of 1 higher fatty acids or rosin acids, or mixtures thereof.
- higher fatty acids as used herein, it is meant acids containing from 8-22 carbon atoms. These may be single isolated fatty acids or may be the whole mixed acids of a fat or oil, or any selected fraction thereof, either saturated or unsaturated.
- the rosin acids which may be employed in the present invention may be any of a wide variety of rosin acids which are available naturally or which have been made available by the modification of naturally occurring rosin acids.
- rosin hydrogenated rosin, dehydrogenated rosin, polymerized rosin, tall oil, the isolated rosin acid fraction of tall oil, and many others.
- the application is applicable to mixtures of fatty acids and rosin acids, as in the case of tall oil or in the case of the rosin acid fraction of tall oil, which fraction may contain approximately 30% fatty acids and approximately 70% rosin acids, with a minor amount of unsaponifiable material.
- aliphatic alcohols may be employed including the monohydric alcohols, methyl, ethyl, propyl, butyl alcohol and the like, and also the polyhydric alcohols, such as the glycols, ethyleneglycol, diethyleneglycol, glycerol, pentaeryt'nritol, 2,2,6,6-tetramethylolcyclohexanol and others.
- the catalysts employed in the present invention are ei her aliph tic or ar matic esters of phosphorous acid.
- the phosphorous acid may be completely or only partially esterified.
- Typical of the phosphorous acid esters which may be'employed are triphenylphosphite, tn'paracresyb phosphite, tri-(Z-ethylhexyl)phosphite and di-.(2-ethyl. hexyDphosphite.
- the esterification is effected by introducing the alcohol, the esterifying acid and the catalyst into a reaction vessel, preferably together with an azeotrope such as xylene or toluene.
- the quantity of catalyst which may be ernployed may vary from %5% based on the Weight of the cid being employed for esterifieat on. Usually, howe r, from 12% is found to be a pref rr d rang
- the temperatures employed during the esterification may vary quite widely, depending upon the nature of the materials being esterified. For example, with low molecular weight monohydric aliphatic alcohols which are quite volatile, it is preferred to operate at fairly low temperatures.
- the reaction is preferably carried out at a much more elevated temperature.
- temperatures of from l50-250 C. are suitable.
- any temperature up to the decomposition temperature of the materials employed may be used.
- the time period for esterification likewise, varies with the nature of the materials, and with the extent to which esterification is desired. It has been found, however, that the employment of the phosphorous esters appreciably reduces the time required, as compared with the same process in which no catalyst is employed.
- Example 1 The following materials were placed in a three-necked round bottom flask: glycerine, 33 g., soybean oil acids, 280 g., triphenyl phosphite, 2 g., and xylene cc.
- the flask was equipped with a mechanical stirrer, a Stark and Dean tube with condenser and a thermometer.
- the reaction was heated by a mantle heater.
- the mixture was heated rapidly to a pot temperature of 180 C., thenv gradually raised to a final temperature of 197-199 C.
- the Water was removed azeotropically.
- the following data show the comparative speed of the above esterification and a control in which the triphenyl phosphite was left out.
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- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
United States Patent PHDSPHITE ESTERS AS ESTERKFICATK DN CATALYSTS No Dra ing. Application January 21, 1e53,
' Seria Pin-3 2, 55
. 4 Claims. c1. 2e0-.-41s.6)
The present invention relates to a process of esterification in which esters of phosphorous acid are employed as esterification catalysts.
The invention is applicable to the esterification of fatty acids or rosin acids with aliphatic alcohols, either monohydric or polyhydric. These catalysts can be used without causing appreciable color formation during the esterification, which is particularly troublesome with conventional catalysts, especially when unsaturated higher fatty acids are esterified. Common esterification catalysts such as strong acids cause darkening of the product during esterification. Moreover, such acid catalysts are difficult to remove. In contrast, the phosphorous esters of the present invention are volatile, and can be removed easily by vacuum distillation at the end of the reaction. Moreover, the esters which are obtained according to the present invention may have a very low free hydroxyl content, depending upon the extent to which it is desired to carry the esterification.
It is, therefore, an object of the present invention to provide a novel esterification process involving the use of phosphorous esters as esterification catalysts.
The invention is applicable to the esterification of 1 higher fatty acids or rosin acids, or mixtures thereof. The
invention may be applied to the esterification of saturated higher fatty acids, but is particularly adapted to the esterification of unsaturated higher fatty acids, since it is with these unsaturated higher fatty acids that the greatest advantages are obtained. By higher fatty acids as used herein, it is meant acids containing from 8-22 carbon atoms. These may be single isolated fatty acids or may be the whole mixed acids of a fat or oil, or any selected fraction thereof, either saturated or unsaturated. The rosin acids which may be employed in the present invention may be any of a wide variety of rosin acids which are available naturally or which have been made available by the modification of naturally occurring rosin acids. These include rosin, hydrogenated rosin, dehydrogenated rosin, polymerized rosin, tall oil, the isolated rosin acid fraction of tall oil, and many others. Moreover, the application is applicable to mixtures of fatty acids and rosin acids, as in the case of tall oil or in the case of the rosin acid fraction of tall oil, which fraction may contain approximately 30% fatty acids and approximately 70% rosin acids, with a minor amount of unsaponifiable material.
A wide variety of aliphatic alcohols may be employed including the monohydric alcohols, methyl, ethyl, propyl, butyl alcohol and the like, and also the polyhydric alcohols, such as the glycols, ethyleneglycol, diethyleneglycol, glycerol, pentaeryt'nritol, 2,2,6,6-tetramethylolcyclohexanol and others.
The catalysts employed in the present invention are ei her aliph tic or ar matic esters of phosphorous acid. The phosphorous acid may be completely or only partially esterified. Typical of the phosphorous acid esters which may be'employed are triphenylphosphite, tn'paracresyb phosphite, tri-(Z-ethylhexyl)phosphite and di-.(2-ethyl. hexyDphosphite.
The esterification is effected by introducing the alcohol, the esterifying acid and the catalyst into a reaction vessel, preferably together with an azeotrope such as xylene or toluene. The quantity of catalyst which may be ernployed may vary from %5% based on the Weight of the cid being employed for esterifieat on. Usually, howe r, from 12% is found to be a pref rr d rang The temperatures employed during the esterification may vary quite widely, depending upon the nature of the materials being esterified. For example, with low molecular weight monohydric aliphatic alcohols which are quite volatile, it is preferred to operate at fairly low temperatures. Where, however, the alcohol is not appreciably volatile, as for example is the case with the glycerine, the reaction is preferably carried out at a much more elevated temperature. In preparing esters of these acids with the usual polyhydric alcohols, such as the glycols and glycerol, temperatures of from l50-250 C. are suitable. However, any temperature up to the decomposition temperature of the materials employed may be used. The time period for esterification, likewise, varies with the nature of the materials, and with the extent to which esterification is desired. It has been found, however, that the employment of the phosphorous esters appreciably reduces the time required, as compared with the same process in which no catalyst is employed.
Example 1 The following materials were placed in a three-necked round bottom flask: glycerine, 33 g., soybean oil acids, 280 g., triphenyl phosphite, 2 g., and xylene cc. The flask was equipped with a mechanical stirrer, a Stark and Dean tube with condenser and a thermometer. The reaction was heated by a mantle heater. The mixture was heated rapidly to a pot temperature of 180 C., thenv gradually raised to a final temperature of 197-199 C. The Water was removed azeotropically. The following data show the comparative speed of the above esterification and a control in which the triphenyl phosphite was left out.
Percent Esteritication Esterifieation Time in hours Trlphenyl phosphite catalyzed y Example 2 The following materials were refluxed in a stirred l-liter, 3-necked flask equipped with thermometer and Stark and Dean tube with condenser: Wood rosin, 340 g. (1 mole rosin acid), pentaerythritol (pentek), 36 g. (1 equivalent of hydroxyl), 6.8 g. di(2-ethylhexyl)phosphite (catalyst), and 60 cc. xylene (azeotrope). A similar run was made with one exception that no di(2-ethylhexyl) phosphite was used. The water which was produced was separated and measured in the Stark and Dean tube. The data obtained were as follows:
Percent Esterifica- Esterification Time Water Eliminated tion on Basis of Water r- Catalyst, No Cata- No Gate- Hours 31m. cc lyst Catalyst lyst I claim as my invention: 1. Process of esterifying an acid selected from the group'consisting of higher fatty acids and rosin acids with an aliphatic alcohol which comprises heating the alcohol and the acid in the presence of a phosphite ester, said ester being selected from the group consisting of aliphatic and aromatic esters.
2. Process of esterifying a higher unsaturated fatty acid with an aliphatic alcohol comprising heating the alcohol and the acid in the presence of a phosphite ester selected from the group consisting of aliphatic and aromatic esters.
3. Process of esterifying an unsaturated higher fatty acid with a polyhydric aliphatic alcohol which comprises heating the alcohol and the acid in the presence of an aromatic phosphite ester.
4. Process of esterifying an unsaturated higher fatty acid with a polyhydric aliphatic alcohol which comprises heating the alcohol and the acid in the presence of phos phite aliphatic ester.
References Cited in the file of this patent UNITED STATES PATENTS 1,796,231 Bannister Nov. 10, 1931
Claims (1)
1. PROCESS OF ESTERIFYING AN ACID SELECTED FROM THE GROUP CONSISTING OF HIGHER FATTY ACIDS AND ROSIN ACIDS WITH AN ALIPHATIC ALCOHOL WHICH COMPRISES HEATING THE ALCOHOL AND THE ACID IN THE PRESENCE OF A PHOSPHITE ESTER, SAID ESTER BEING SELECTED FROM THE GROUP CONSISTING OF ALIPHATIC AND AROMATIC ESTERS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US332555A US2729660A (en) | 1953-01-21 | 1953-01-21 | Phosphite esters as esterification catalysts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US332555A US2729660A (en) | 1953-01-21 | 1953-01-21 | Phosphite esters as esterification catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2729660A true US2729660A (en) | 1956-01-03 |
Family
ID=23298766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US332555A Expired - Lifetime US2729660A (en) | 1953-01-21 | 1953-01-21 | Phosphite esters as esterification catalysts |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2729660A (en) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409148A (en) * | 1981-12-09 | 1983-10-11 | Uop Inc. | Process for the reduction of unsaturated carboxylic acids |
| US4548746A (en) * | 1984-05-14 | 1985-10-22 | Westvaco Corporation | Rosin pentaerythritol ester preparation improvement |
| US4643848A (en) * | 1986-02-21 | 1987-02-17 | Westvaco Corporation | Modified rosin ester preparation |
| US4690783A (en) * | 1986-08-29 | 1987-09-01 | Union Camp Corporation | Method of preparing rosin ester from polyol with phosphorous acid catalyst |
| US4693847A (en) * | 1986-11-14 | 1987-09-15 | Union Camp Corporation | Method of preparing hot-melt stable rosin ester with organic ester of hypophosphorous acid catalyst |
| EP0270773A1 (en) * | 1986-11-14 | 1988-06-15 | Union Camp Corporation | Method of preparing rosin esters of improved thermal stability |
| US4758379A (en) * | 1986-11-14 | 1988-07-19 | Union Camp Corporation | Process of preparing polyol esters of rosin with excess rosin |
| EP0459760A2 (en) * | 1990-05-30 | 1991-12-04 | Union Camp Corporation | Method for the preparation of light-colored rosin esters |
| US5543110A (en) * | 1993-03-16 | 1996-08-06 | Westvaco Corporation | Tall oil deodorization process |
| US5830992A (en) * | 1996-12-12 | 1998-11-03 | Union Camp Corporation | Light color, color stable rosin esters and methods for preparing same |
| US20070104923A1 (en) * | 2005-11-04 | 2007-05-10 | Whitaker Robert H | Novel mineral composition |
| US20080173212A1 (en) * | 2005-11-04 | 2008-07-24 | Whitaker Robert H | Novel mineral composition |
| US20110213120A1 (en) * | 2010-03-01 | 2011-09-01 | Arizona Chemical Company | Rosin esters for non-woven applications, methods of making and using and products therefrom |
| WO2015048426A2 (en) | 2013-09-27 | 2015-04-02 | Arizona Chemical Company, Llc | Methods of making rosin esters |
| WO2015048421A2 (en) | 2013-09-27 | 2015-04-02 | Arizona Chemical Company, Llc | Rosin esters and compositions thereof |
| WO2015048415A2 (en) | 2013-09-27 | 2015-04-02 | Arizona Chemical Company, Llc | Rosin esters and compositions thereof |
| WO2016154456A1 (en) | 2015-03-26 | 2016-09-29 | Arizona Chemical Company, Llc | Compositions containing rosin ester and ethylene polymers |
| WO2017117576A1 (en) | 2015-12-31 | 2017-07-06 | Arizona Chemical Company, Llc | Oligoesters and compositions thereof |
| WO2018058005A1 (en) | 2016-09-23 | 2018-03-29 | Kraton Chemical, Llc | Oligoesters compositions and methods of making and using same |
| US9951254B2 (en) | 2013-09-27 | 2018-04-24 | Arizona Chemical Company, Llc | Compositions containing ethylene polymers |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1796231A (en) * | 1930-05-16 | 1931-03-10 | Commercial Solvents Corp | Oleic acid ester |
-
1953
- 1953-01-21 US US332555A patent/US2729660A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1796231A (en) * | 1930-05-16 | 1931-03-10 | Commercial Solvents Corp | Oleic acid ester |
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409148A (en) * | 1981-12-09 | 1983-10-11 | Uop Inc. | Process for the reduction of unsaturated carboxylic acids |
| US4548746A (en) * | 1984-05-14 | 1985-10-22 | Westvaco Corporation | Rosin pentaerythritol ester preparation improvement |
| DE3516776A1 (en) * | 1984-05-14 | 1985-11-14 | Westvaco Corp., New York, N.Y. | METHOD FOR PRODUCING COLOPHONIUM PENTAERYTHRITESTER |
| FR2564101A1 (en) * | 1984-05-14 | 1985-11-15 | Westvaco Corp | IMPROVED PROCESS FOR ESTERIFYING POTATORY THERAPY WITH PENTAERYTHRITOL |
| NL8501335A (en) * | 1984-05-14 | 1985-12-02 | Westvaco Corp | METHOD FOR EESTIFYING NATURAL RESIN WITH PENTAERYTRITOL AND THE PRODUCT OBTAINED BY THIS METHOD |
| US4643848A (en) * | 1986-02-21 | 1987-02-17 | Westvaco Corporation | Modified rosin ester preparation |
| US4690783A (en) * | 1986-08-29 | 1987-09-01 | Union Camp Corporation | Method of preparing rosin ester from polyol with phosphorous acid catalyst |
| US4693847A (en) * | 1986-11-14 | 1987-09-15 | Union Camp Corporation | Method of preparing hot-melt stable rosin ester with organic ester of hypophosphorous acid catalyst |
| EP0270773A1 (en) * | 1986-11-14 | 1988-06-15 | Union Camp Corporation | Method of preparing rosin esters of improved thermal stability |
| US4758379A (en) * | 1986-11-14 | 1988-07-19 | Union Camp Corporation | Process of preparing polyol esters of rosin with excess rosin |
| EP0459760A2 (en) * | 1990-05-30 | 1991-12-04 | Union Camp Corporation | Method for the preparation of light-colored rosin esters |
| EP0459760A3 (en) * | 1990-05-30 | 1993-03-24 | Union Camp Corporation | Method for the preparation of light-colored rosin esters |
| US5543110A (en) * | 1993-03-16 | 1996-08-06 | Westvaco Corporation | Tall oil deodorization process |
| US5830992A (en) * | 1996-12-12 | 1998-11-03 | Union Camp Corporation | Light color, color stable rosin esters and methods for preparing same |
| US20070104923A1 (en) * | 2005-11-04 | 2007-05-10 | Whitaker Robert H | Novel mineral composition |
| US20080173212A1 (en) * | 2005-11-04 | 2008-07-24 | Whitaker Robert H | Novel mineral composition |
| US7651559B2 (en) | 2005-11-04 | 2010-01-26 | Franklin Industrial Minerals | Mineral composition |
| US20110213120A1 (en) * | 2010-03-01 | 2011-09-01 | Arizona Chemical Company | Rosin esters for non-woven applications, methods of making and using and products therefrom |
| US9940852B2 (en) | 2013-09-27 | 2018-04-10 | Kranton Chemical, LLC | Rosin esters and compositions thereof |
| WO2015048421A2 (en) | 2013-09-27 | 2015-04-02 | Arizona Chemical Company, Llc | Rosin esters and compositions thereof |
| WO2015048415A2 (en) | 2013-09-27 | 2015-04-02 | Arizona Chemical Company, Llc | Rosin esters and compositions thereof |
| WO2015048426A2 (en) | 2013-09-27 | 2015-04-02 | Arizona Chemical Company, Llc | Methods of making rosin esters |
| US9951254B2 (en) | 2013-09-27 | 2018-04-24 | Arizona Chemical Company, Llc | Compositions containing ethylene polymers |
| US10011740B2 (en) | 2013-09-27 | 2018-07-03 | Kraton Chemical, Llc | Rosin esters and compositions thereof |
| US10336922B2 (en) | 2013-09-27 | 2019-07-02 | Kraton Chemical, Llc | Compositions containing ethylene polymers |
| WO2016154456A1 (en) | 2015-03-26 | 2016-09-29 | Arizona Chemical Company, Llc | Compositions containing rosin ester and ethylene polymers |
| WO2017117576A1 (en) | 2015-12-31 | 2017-07-06 | Arizona Chemical Company, Llc | Oligoesters and compositions thereof |
| US10435586B2 (en) | 2015-12-31 | 2019-10-08 | Kraton Chemical, Llc | Oligoesters and compositions thereof |
| WO2018058005A1 (en) | 2016-09-23 | 2018-03-29 | Kraton Chemical, Llc | Oligoesters compositions and methods of making and using same |
| US10407593B2 (en) | 2016-09-23 | 2019-09-10 | Kraton Chemical, Llc | Oligoesters compositions and methods of making and using same |
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