US3140300A - Composition consisting of maleic anhydride and a fatty acid - Google Patents
Composition consisting of maleic anhydride and a fatty acid Download PDFInfo
- Publication number
- US3140300A US3140300A US69256A US6925660A US3140300A US 3140300 A US3140300 A US 3140300A US 69256 A US69256 A US 69256A US 6925660 A US6925660 A US 6925660A US 3140300 A US3140300 A US 3140300A
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- Prior art keywords
- flaking
- maleic anhydride
- product
- fatty acid
- dust
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- 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.)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/573—Separation; Purification; Stabilisation; Use of additives
Definitions
- This application relates to a specification grade solid maleic anhydride product in dust-free, particulate form containing a small amount of flaking agent, and also to processes for converting such a material from the liquid form to the particulate, solid form by flaking, and more particularly it relates to such a product and process wherein the flaking agent is a higher aliphatic acid such as stearic acid.
- Maleic anhydride is a commercially important material and for many purposes it is packaged and shipped in free flowing solid form such as flakes, or the flakes may be converted to briquettes.
- Specification grade maleic anhydride may contain a small amount or trace of maleic acid as well as of xylene or the like azeotroping agent, and such material tends to form powder or dust when the molten material is flaked in a conventional manner.
- dust is particularly bothersome from the manufacturing viewpoint (requiring costly shut-down for cleaning out), gives rise to health hazards, and also increases losses due to evaporation from the relatively extensive surface thereof.
- the art is confronted by the problem of providing substantially dust free specification grade maleic anhydride in free-flowing solid or particulate form, as well as methods for producing such a product in a convenient and economic manner.
- a method for producing specification grade maleic anhydride product in dust-free, solid, particulate form which comprises flaking molten maleic anhydride containing a higher, aliphatic, mono-carboxylic acid as a flaking agent, the amount of the flaking agent being insufiicient to render the composition off-grade and yet sufficient to permit converting the molten material to the desired form by flaking, without dusting;
- the following runs are carried out by converting the molten material into flake form by applying the material in a thin layer to a revolving drum on which the material cools, solidifies, and is removed in flake form by a stationary knife.
- the apparatus used includes a revolving drum cooled by water which drum dips in a shallow heated pan filled with the molten material. A knife or doctor against the drum removes the product from the surface in solid form.
- the charge of maleic anhydride is brought to a temperature of about 58 C. and the cooled rotating drum is brought into the pan.
- the interior of the drum is cooled by means of water maintained at 16 to 28 C. The following results are obtained using a 5 inch diameter drum.
- EXAMPLE I High purity maleic anhydride (M.P. of about 52.6 C.) is melted together with 0.1 wt. percent thereof of stearic acid and the mixture is flaked using a drum speed of 10 rpm. The product obtained is oblong in form with the majority of the particles of inch to /2 inch in length about inch in width and about 12 thousandths of inch thick. This product is dust free and does not tend to cake up readily on standing.
- Comparative Example A In a comparative run except using no additive, small flakes of about one fourth or less of the size of those of Example I are obtained, with considerable dust. Upon standing the product tends to cake rather rapidly.
- the procedure of the invention gives specification grade product in large particulate form which is free-flowing and dust-free, as illustrated in Example I.
- the comparative run without the addive produces unsatisfactory particles and an undesirable amount of dust.
- the maleic anhydride starting material as Well as the product is of specification grade, and this grade is defined as:
- the standard used to indicate the quantity or intensity of color of the products in molten or liquid form is known as the APHA standard color test. This test is one developed by the American Public Health Association which is known as the Hazen Platinum-Cobalt Scale a description of which is found on page 2048 of the 5th edition of Standard Methods of Chemical Analysis, by Wilford W. Scott.
- the flaking may be carried out on large commercial type apparatus which may be of a diameter 3 to 4 feet and this gives relatively larger flakes, if dust-free material is obtained with the small diameter apparatus.
- the amount of flaking agent is insuflicient to render the composition off-grade; however, it is suflicient to permit converting the molten material to the desired from by flaking, without dusting. In the absence of the flaking agent, the starting material tends to dust and gives particles of an undesirable small size.
- the flaking agent may be a higher aliphatic, mono-carboxylic acid which is compatible with the anhydride and does not render it olfgrade in the amounts required for flaking. Generally,
- this acid should contain at least about 10 carbon atoms in the molecule and desirably not over 25 carbon atoms.
- the preferred amount of flaking agent is the minimum required to attain the desired flaking effect, and generally an amount of 0.07 and 0.1 weight percent is effective.
- The'initial or starting maleic anhydride may contain a small amount of Xylene or the like azeotroping agent, and 5 it may contain a small amount of maleic acid.
- the flaking operation is conducted with the melt at a temperature at a range of about 53 to 60 C., preferably about 55 to 58 C.
- the cooling medium in the flaking drum may be a temperature in the range of 16 to 28 C.
- the flaking drum is preferably rotated at a sped of 8 to a 12 rotations per minute.
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,140,300 COMPOSITION CONSISTING 0F MALEIC AN- HYDRIDE AND A FATTY ACID Manfred Gans, Leonia, and Joseph L. Russell, Ridgewood, N.J., assignors to Halcon International, Inc., a
corporation of Delaware No Drawing. Filed Nov. 15, 1960, Ser. No. 69,256
2 Claims. (Cl. 260-3463) This application relates to a specification grade solid maleic anhydride product in dust-free, particulate form containing a small amount of flaking agent, and also to processes for converting such a material from the liquid form to the particulate, solid form by flaking, and more particularly it relates to such a product and process wherein the flaking agent is a higher aliphatic acid such as stearic acid.
Maleic anhydride is a commercially important material and for many purposes it is packaged and shipped in free flowing solid form such as flakes, or the flakes may be converted to briquettes. Specification grade maleic anhydride may contain a small amount or trace of maleic acid as well as of xylene or the like azeotroping agent, and such material tends to form powder or dust when the molten material is flaked in a conventional manner. Such dust is particularly bothersome from the manufacturing viewpoint (requiring costly shut-down for cleaning out), gives rise to health hazards, and also increases losses due to evaporation from the relatively extensive surface thereof. The art is confronted by the problem of providing substantially dust free specification grade maleic anhydride in free-flowing solid or particulate form, as well as methods for producing such a product in a convenient and economic manner.
The discoveries associated with the invention and relating to the solutions of the above problems, and the objects achieved in accordance with the invention as set forth herein include the provision of:
A specification grade maleic anhydride product in dustfree, solid, particulate form containing a higher, aliphatic, mono-carboxylic acid as a flaking agent, the amount of the flaking agent being insufiicient to render the composition off-grade and yet suflicient to permit converting the molten material to the desired form by flaking, without dusting;
A method for producing specification grade maleic anhydride product in dust-free, solid, particulate form which comprises flaking molten maleic anhydride containing a higher, aliphatic, mono-carboxylic acid as a flaking agent, the amount of the flaking agent being insufiicient to render the composition off-grade and yet sufficient to permit converting the molten material to the desired form by flaking, without dusting;
Such a method wherein the flaking agent is a straightchain fatty acid;
Such a method wherein the amount of flaking agent is in the range of 0.07 to 0.1 weight percent;
Such a method wherein the flaking agent is stearic acid.
Such a method wherein the product contains a small amount of xylene;
Such a method wherein the product contains small amount of maleic acid;
Such a method wherein the flaking drum is rotated at a speed of 8 to 12 rotations per minute;
Such a method wherein the molten material is maintained at a temperature in the range of 53 as to 60 0.;
Such a method wherein the cooling medium in the flaking drum is at a temperature in the range of 16 to 28 C.; and
Other objects which will be apparent as details or embodiments of the invention are set forth hereinafter.
In order to indicate still more fully the nature of the 3,140,300 Patented July 7, 1964 present invention, the following examples of typical pro cedures are set forth in which parts and percent mean part and percent by weight, respectively, unless otherwise indicated, it being understood that these examples are presented as illustrative only and are not intended to limit the scope of the invention.
The following runs are carried out by converting the molten material into flake form by applying the material in a thin layer to a revolving drum on which the material cools, solidifies, and is removed in flake form by a stationary knife. The apparatus used includes a revolving drum cooled by water which drum dips in a shallow heated pan filled with the molten material. A knife or doctor against the drum removes the product from the surface in solid form.
The charge of maleic anhydride is brought to a temperature of about 58 C. and the cooled rotating drum is brought into the pan. The interior of the drum is cooled by means of water maintained at 16 to 28 C. The following results are obtained using a 5 inch diameter drum.
EXAMPLE I High purity maleic anhydride (M.P. of about 52.6 C.) is melted together with 0.1 wt. percent thereof of stearic acid and the mixture is flaked using a drum speed of 10 rpm. The product obtained is oblong in form with the majority of the particles of inch to /2 inch in length about inch in width and about 12 thousandths of inch thick. This product is dust free and does not tend to cake up readily on standing.
Comparative Example A In a comparative run except using no additive, small flakes of about one fourth or less of the size of those of Example I are obtained, with considerable dust. Upon standing the product tends to cake rather rapidly.
The procedure of the invention gives specification grade product in large particulate form which is free-flowing and dust-free, as illustrated in Example I. On the other hand, the comparative run without the addive produces unsatisfactory particles and an undesirable amount of dust.
These runs are repeated with specification grade maleic anhydride containing a trace of xylene and comparable results to Example I are obtained with the additive; on the other hand, if no additive is present most of the product is in the form of a fine troublesome dust.
The maleic anhydride starting material as Well as the product is of specification grade, and this grade is defined as:
M.P 52.4-52..8 C.
Color (Hazen) 20 or less (for the molten material).
5% Xylene solution Clear.
Purity 99.5% minimum.
The standard used to indicate the quantity or intensity of color of the products in molten or liquid form is known as the APHA standard color test. This test is one developed by the American Public Health Association which is known as the Hazen Platinum-Cobalt Scale a description of which is found on page 2048 of the 5th edition of Standard Methods of Chemical Analysis, by Wilford W. Scott.
Comparable results to the foregoing are achieved that follows modifications thereof, including the following:
The flaking may be carried out on large commercial type apparatus which may be of a diameter 3 to 4 feet and this gives relatively larger flakes, if dust-free material is obtained with the small diameter apparatus.
The amount of flaking agent is insuflicient to render the composition off-grade; however, it is suflicient to permit converting the molten material to the desired from by flaking, without dusting. In the absence of the flaking agent, the starting material tends to dust and gives particles of an undesirable small size. The flaking agent may be a higher aliphatic, mono-carboxylic acid which is compatible with the anhydride and does not render it olfgrade in the amounts required for flaking. Generally,
this acid should contain at least about 10 carbon atoms in the molecule and desirably not over 25 carbon atoms.
The preferred amount of flaking agent is the minimum required to attain the desired flaking effect, and generally an amount of 0.07 and 0.1 weight percent is effective.
The'initial or starting maleic anhydride may contain a small amount of Xylene or the like azeotroping agent, and 5 it may contain a small amount of maleic acid.
The flaking operation is conducted with the melt at a temperature at a range of about 53 to 60 C., preferably about 55 to 58 C. The cooling medium in the flaking drum may be a temperature in the range of 16 to 28 C.
'The flaking drum is preferably rotated at a sped of 8 to a 12 rotations per minute.
In view of the foregoing disclosures, variations and modifications thereof will be apparent to one skilled in the art and it is intended to include Within the invention References Cited in the file ofthis patent UNITED STATES PATENTS 1,934,450 Sheppard et a1 Nov. 7, 1933 2,211,738 Cairns Aug. 13, 1940 2,770,630 Miller Nov. 13, 1956 FOREIGN PATENTS 527,157 Canada July 3, 1956 OTHER REFERENCES Riegel Industrial Chemistry (fifth edition; 1949) page 876.
Claims (1)
1. A COMPOSITION CONSISTING ESSENTIALLY OF AT LEAST 99.5 WT. PERCENT MALEIC ANHYDRIDE AND AT LEAST 0.07 WT. PERCENT OF AN ALIPHATIC MONOCARBOXYLIC ACID HAVING FROM ABOUT 10 TO 25 CARBON ATOMS.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US69256A US3140300A (en) | 1960-11-15 | 1960-11-15 | Composition consisting of maleic anhydride and a fatty acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US69256A US3140300A (en) | 1960-11-15 | 1960-11-15 | Composition consisting of maleic anhydride and a fatty acid |
Publications (1)
Publication Number | Publication Date |
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US3140300A true US3140300A (en) | 1964-07-07 |
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US69256A Expired - Lifetime US3140300A (en) | 1960-11-15 | 1960-11-15 | Composition consisting of maleic anhydride and a fatty acid |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3459798A (en) * | 1966-06-23 | 1969-08-05 | Du Pont | Process for preventing caking of adipic acid,and product |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1934450A (en) * | 1929-01-03 | 1933-11-07 | Eastman Kodak Co | Process for the manufacture of cellulose acetate and product thereof |
US2211738A (en) * | 1937-07-08 | 1940-08-13 | Hercules Powder Co Ltd | Blasting explosive |
CA527157A (en) * | 1956-07-03 | F. Heald Robert | Treatment of soap particles | |
US2770630A (en) * | 1952-03-12 | 1956-11-13 | Allied Chem & Dye Corp | Recovery of maleic anhydride |
-
1960
- 1960-11-15 US US69256A patent/US3140300A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA527157A (en) * | 1956-07-03 | F. Heald Robert | Treatment of soap particles | |
US1934450A (en) * | 1929-01-03 | 1933-11-07 | Eastman Kodak Co | Process for the manufacture of cellulose acetate and product thereof |
US2211738A (en) * | 1937-07-08 | 1940-08-13 | Hercules Powder Co Ltd | Blasting explosive |
US2770630A (en) * | 1952-03-12 | 1956-11-13 | Allied Chem & Dye Corp | Recovery of maleic anhydride |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3459798A (en) * | 1966-06-23 | 1969-08-05 | Du Pont | Process for preventing caking of adipic acid,and product |
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