NL2030938A - A method for preparing dehydroabietic acid - Google Patents
A method for preparing dehydroabietic acid Download PDFInfo
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- NL2030938A NL2030938A NL2030938A NL2030938A NL2030938A NL 2030938 A NL2030938 A NL 2030938A NL 2030938 A NL2030938 A NL 2030938A NL 2030938 A NL2030938 A NL 2030938A NL 2030938 A NL2030938 A NL 2030938A
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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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
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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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
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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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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Abstract
The invention discloses a method for preparing dehydroabietic acid, which belongs to the forest products chemical industry. The rosin that the proportion of abietic resin acid in the total resin acid is 292% is the reactant in the invention, mixing with catalyst, reacting, then obtaining product, removing the catalyst in the product, and obtaining dehydroabietic acid with a purity of 290%. Compared with disproportionated rosin, the separation and purification of abietic resin acid from the rosin is easier to achieve. The invention obviously simplified the purification process, improves the yield, significantly reduces the usage amount of the solvent, and effectively reduces the production cost, has a good application prospect.
Description
A METHOD FOR PREPARING DEHYDROABIETIC ACID
The invention relates to the forest products chemical industry, in particular to a method for preparing dehydroabietic acid.
The main component of rosin is resin acid. Resin acid is a general term for a class of mixtures, Most of them are Ca0H3602, which is a monocarboxylic acid with a tricyclic phenanthrene skeleton and two double bonds. A few of them are bicyclic carboxylic acids.
Rosin resin acids can be divided into three types according to the alkyl group and the position of the double bond.
The first type is abietic acid resin acid, which includes abietic acid, dehydroabietic acid, levopimaric acid, palustric acid and neoabietic acid.
En / 9 / 1 í R PI ; A 9 LL | - hag
COOH ‘COOH COOH
Abietic acid Dehydroabietic acid Levopimaric acid / fy | L } x. “COOH “COOH
Palustric acid Neoabietic acid
The second type is pimaric acid/isopimaric acid type resin acid, which includes sandaracopimaric acid, pimaric acid and isopimaric acid.
on, STN > OD =
AY eN sed 7 COOH 7 coon COOH
Sandaracopimarie acid A) Pimaric acid Isopimaric acid
Pa
DS ; .
Sa € 7 "CooH 7 coon
Pimaric acid Isopimaric acid
The third type is bicyclic resin acid that also called Laudan resin acid, which includes elliotinoic acid and mercusic acid. Elliotinoic acid is a monobasic acid, and mercusic acid is a dibasic acid.
DC
; br COOH
L “, “ COOH
Elliotinoic acid Mercusic acid
The dehydroabietic acid 1s a kind of resin acid produced by the disproportionation reaction of resin acid in rosin. Its unique properties are widely used in the fields of medicine and chemical analysis.
Chinese patent No. 200410078372.2 discloses a method for the simultaneous production of light-colored disproportionated rosin with high content of dehydroabietic acid and p-cymene, and the content of dehydroabietic acid in the product is 72-82%. Chinese patent No. 201310378151.6 discloses a method for increasing the content of dehydroabietic acid in disproportionated rosin, and the content of the dehydroabietic acid in the product is up to 743%. Chinese patent No. 201710596640.7 discloses a process for producing disproportionated rosin with high content of dehydroabietic acid, and the highest content of dehydroabietic acid in the product 1s 74.8%. The purity requirement of dehydrabietic acid products with commercial value on the market is not less than 90%. The above methods cannot meet this requirement. In order to obtain high-purity dehydroabietic acid, the current process is converting rosin into disproportionated rosin with a content of 40-60% dehydroabietic acid, and then completing some steps to obtain dehydroabietic acid with a purity of more than 90%, such as amination, extraction, recrystallization, acid reduction, recrystallization, drying, etc. This process uses a large amount of solvents, and has a complicated process, low yield and high cost.
The purpose of the present invention is to overcome the above shortcomings, and further provide a method for preparing dehydroabietic acid. The purity of the dehydroabietic acid obtained by the method is not less than 90%, and the process of the method is simple. At the same time, this method achieves high yield and low cost.
Dehydroabietic acid is converted from the internal redox reaction of abietic acid-type resin acid molecules, which reaction is also called disproportionation reaction. The structure of abietic resin acid contains conjugated double bonds, so it can generate dehydroabietic acid.
The structure of pimaric acid and isopimaric acid type resin acid do not contain conjugated double bonds, so they cannot generate dehydroabietic acid. The structure of the bicyclic resin acid that also called Laudan resin acid is bicyclic, it cannot generate dehydroabietic acid too.
The inventor of this patent used gas chromatograph to measure the proportion of resin acids in rosin and found that if the proportion of abietic acid-type resin acids in the total resin acids is not less than 92%, and the palladium-carbon catalyst is used to catalyze the reaction at high temperatures, the dehydroabietic acid that purity is not less than 90% will be obtained.
In order to achieve the above objective, the invention provides a method for preparing dehydroabietic acid, comprising: the rosin that the proportion of abietic resin acid in the total resin acid is 292% is the reactant, mixing with catalyst, reacting, and obtaining product, then removing the catalyst in the product to obtain dehydroabietic acid with a purity of 290%.
The detection of rosin components showed that the sundry tree species and picking time resulted in significant differences in the proportion of resin acid components in rosin. In the rosin that has not been separated and purified, the proportion of abietic acid resin acid is generally not more than 86%. Therefore, for the rosin that proportion of abietic acid resin acid in the total resin acid >92%, the separation and purification is required.
Preferably, the rosin that the proportion of abietic resin acid in the total resin acid is 292% is prepared according to the following steps: (1) rosin undergoes isomerization reaction at high temperature; (2) after the reaction, adding extraction solvent, cooling down, precipitating rosin crystals, and obtaining the rosin that the proportion of abietic resin acid in the total resin acid is 292%.
More preferably, the process of step (1) comprising: heating up the rosin under the protection of nitrogen, keeping the reaction at 275-285°C for 30-60 minutes. Most preferably, keeping the reaction at 285°C for 30 minutes.
More preferably, the process of step (2) comprising: after the reaction, cooling down to 50-70°C, most preferably 60°C, adding the extraction solvent, raising the temperature to dissolve the rosin completely, then cooling down to 0-8°C, precipitating the rosin crystals, and obtaining the rosin that the proportion of abietic resin acid in the total resin acid is >92%.
More preferably, in step (2), the extraction solvent is at least one of methanol, ethanol, ethyl acetate, acetone and petroleum ether. More preferably, the extraction solvent is a mixed solution of ethyl acetate and methanol, most preferably, in the mixture of ethyl acetate and methanol, the volume ratio of ethyl acetate to methanol is 92-95:5-8.
Preferably, the catalyst is palladium-carbon catalyst. More preferably, the weight percentage content of palladium in the palladium-carbon catalyst is 3-5%.
More preferably, the weight ratio of the palladium-carbon catalyst to the rosin is 1:1000-5000.
Preferably, the temperature of the reaction is 270-310°C, more preferably 290°C.
Preferably, the time of reaction is 120-240 minutes, more preferably 150 minutes.
Preferably, the method for removing the catalyst in the product comprising: cooling down to 200-250° C, and putting the product in filter to filter the catalyst.
The beneficial technical effects brought by the invention:
The method for preparing dehydroabietic acid provided by the present invention increases the content of abietic acid-type resin acids that can generate dehydroabietic acid, so that its ratio to the total resin acids is >92%. Prior art separates and purifies dehydroabietic acid from disproportionated rosin, compared with it, the separation and purification of abietic resin acid from the rosin is easier to achieve. The invention obviously simplifys the purification process, improves the yield, significantly reduces the usage amount of the solvent 5 and production cost.
In order to make the technical means, creative features, objectives and effects of the present invention are easy to understand, specific embodiments are used to further illustrate the present invention, while the following embodiments are only preferred embodiments of the present invention instead of all of them. Other embodiments obtained by those skilled in the art without creative work shall fall based on the following embodiments, within the protection scope of the present invention. Unless otherwise specified, the operating methods used are all conventional operating methods, the equipment used is all conventional equipment, and the equipment materials used in each embodiment are same in the following embodiments.
In the following examples, the softening point of the masson pine rosin is 78.8°C, the acid value is 176.9mg KOH/g, and the Ghanaian color number is 7. The softening point of the slash rosin is 76.9°C, the acid value is 168.8mg KOH/g, and the Ghanaian color number is 6.5.
The weight percentage content of the palladium is 5% in the palladium-carbon catalyst.
The measurement method is as follows: the softening point is determined by the ring and ball method, the acid value is determined by acid-base titration, the color is determined by
Ghanaian color method, and the product components is determined by gas chromatography area normalization method.
Example 1: (1) Crushing 250g of masson pine rosin, putting it into a three-necked flask equipped with reflux device, heating under the protection of nitrogen, then raising the temperature to 280°C and reacting for 40 minutes. Cooling down to 60°C, adding 700ml of mixture of ethyl acetate and methanol (25 °C, the volume ratio of ethyl acetate to methanol is 92:8), and raising the temperature to make the solution reflux. After the rosin is completely dissolved, reducing the temperature to 5°C, then placing for 24 hours to filtering out crystals, and drying the crystals to constant weight in an oven at 100°C under the protection of nitrogen. 177.9g of product A was obtained in this example, and the yield was 71.16%. The composition of resin acid was determined by gas chromatograph, as shown in table 1. (2)Weighing 100g of product A, then weighing 0.045g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 180 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 99.12g of product was obtained in this example, and the yield was 99.12%, and the reaction product yield (based on rosin) was calculated as follow: 71.16% 99.12%=70.37%.
The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in Table 2.
Example 2: (1) Crushing 250g of masson pine rosin, putting it into a three-necked flask equipped with reflux device, heating under the protection of nitrogen, then raising the temperature to 275°C and reacting for 60 minutes. Cooling down to 60°C, adding 700ml of mixture of ethyl acetate and methanol (25 °C, the volume ratio of ethyl acetate to methanol is 92:8), and raising the temperature to make the solution reflux. After the rosin is completely dissolved, reducing the temperature to 5°C, then placing for 24 hours to filtering out crystals, and drying the crystals to constant weight in an oven at 100°C under the protection of nitrogen. 175.5g of product A was obtained in this example, and the yield was 70.2%. The composition of resin acid was determined by gas chromatograph, as shown in table 1. (2)Weighing 100g of product A, then weighing 0.05g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 180 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst.
99.07g of product was obtained in this example, and the yield was 99.07%, and the reaction product yield (based on rosin) was calculated as follow: 70.2%x99.07%=69.54%. The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in
Table 2.
Example 3: (1) Crushing 250g of masson pine rosin, putting it into a three-necked flask equipped with reflux device, heating under the protection of nitrogen, then raising the temperature to 285°C and reacting for 30 minutes. Cooling down to 60°C, adding 700ml of mixture of ethyl acetate and methanol (25 °C, the volume ratio of ethyl acetate to methanol is 92:8), and raising the temperature to make the solution reflux. After the rosin is completely dissolved, reducing the temperature to 5°C, then placing for 24 hours to filtering out crystals, and drying the crystals to constant weight in an oven at 100°C under the protection of nitrogen. 182.1g of product A was obtained in this example, and the yield was 72.84%. The composition of resin acid was determined by gas chromatograph, as shown in table 1. (2)Weighing 100g of product A, then weighing 0.038g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 120 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 99 24g of product was obtained in this example, and the yield was 99.24%, and the reaction product yield (based on rosin) was calculated as follow: 72.84% 99.24% =72.23%.
The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in Table 2.
Example 4: (1) Crushing 250g of masson pine rosin, putting it into a three-necked flask equipped with reflux device, heating under the protection of nitrogen, then raising the temperature to
275°C and reacting for 30 minutes. Cooling down to 60°C, adding 700ml of mixture of ethyl acetate and methanol (25 °C, the volume ratio of ethyl acetate to methanol is 92:8), and raising the temperature to make the solution reflux. After the rosin is completely dissolved, reducing the temperature to 5°C, then placing for 24 hours to filtering out crystals, and drying the crystals to constant weight in an oven at 100°C under the protection of nitrogen. 175g of product A was obtained in this example, and the yield was 70%. The composition of resin acid was determined by gas chromatograph, as shown in table 1. (2)Weighing 100g of product A, then weighing 0.04g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 240 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 98.8g of product was obtained in this example, and the yield was 98.8%, and the reaction product yield (based on rosin) was calculated as follow: 70%x98.8%=69. 16%. The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in Table 2.
Example 5: (1) Crushing 250g of slash rosin, putting it into a three-necked flask equipped with reflux device, heating under the protection of nitrogen, then raising the temperature to 280°C and reacting for 40 minutes. Cooling down to 60°C, adding 700ml of mixture of ethyl acetate and methanol (25 °C, the volume ratio of ethyl acetate to methanol is 95:5), and raising the temperature to make the solution reflux. After the rosin is completely dissolved, reducing the temperature to 5°C, then placing for 24 hours to filtering out crystals, and drying the crystals to constant weight in an oven at 100°C under the protection of nitrogen. 160g of product A was obtained in this example, and the yield was 64%. The composition of resin acid was determined by gas chromatograph, as shown in table 1. (2)Weighing 100g of product A, then weighing 0.065g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 150 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 98.78g of product was obtained in this example, and the yield was 98.78%, and the reaction product yield (based on rosin) was calculated as follow: 64%x98.78%=63.21%. The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in
Table 2.
Example 6: (1) Crushing 250g of slash rosin, putting it into a three-necked flask equipped with reflux device, heating under the protection of nitrogen, then raising the temperature to 285°C and reacting for 30 minutes. Cooling down to 60°C, adding 700ml of mixture of ethyl acetate and methanol (25 °C, the volume ratio of ethyl acetate to methanol is 95:5), and raising the temperature to make the solution reflux. After the rosin is completely dissolved, reducing the temperature to 5°C, then placing for 24 hours to filtering out crystals, and drying the crystals to constant weight in an oven at 100°C under the protection of nitrogen. 161.75g of product A was obtained in this example, and the yield was 64.7%. The composition of resin acid was determined by gas chromatograph, as shown in table 1. (2)Weighing 100g of product A, then weighing 0.055g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 180 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 98.74g of product was obtained in this example, and the yield was 98.74%, and the reaction product yield (based on rosin) was calculated as follow: 64. 7%x98 74% =63.32%. The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in
Table 2.
Example 7: (1) Crushing 250g of slash rosin, putting it into a three-necked flask equipped with reflux device, heating under the protection of nitrogen, then raising the temperature to 275°C and reacting for 30 minutes. Cooling down to 60°C, adding 700ml of mixture of ethyl acetate and methanol (25 °C, the volume ratio of ethyl acetate to methanol is 95:5), and raising the temperature to make the solution reflux. After the rosin is completely dissolved, reducing the temperature to 5°C, then placing for 24 hours to filtering out crystals, and drying the crystals to constant weight in an oven at 100°C under the protection of nitrogen. 156.4g of product A was obtained in this example, and the yield was 62.56%. The composition of resin acid was determined by gas chromatograph, as shown in table 1. (2) Weighing 100g of product A, then weighing 0.07g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 240 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 98.65g of product was obtained in this example, and the yield was 98.65%, and the reaction product yield (based on rosin) was calculated as follow: 62.56%%98.65%=61.72%.
The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in Table 2.
Comparative example 1:
The composition of masson pine rosin resin acid was determined by gas chromatograph, as shown in table 1.
Weighing 100g of masson pine rosin, then weighing 0.045g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 150 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 98.18g of product was obtained in this example, and the yield was 98.18%. The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in Table 2.
Comparative example 2:
(1) Crushing 250g of masson pine rosin, putting it into a three-necked flask equipped with reflux device, heating under the protection of nitrogen, then raising the temperature to 275°C and reacting for 20 minutes. Cooling down to 60°C, adding 700ml of mixture of ethyl acetate and methanol (25 °C, the volume ratio of ethyl acetate to methanol is 92:8), and raising the temperature to make the solution reflux. After the rosin is completely dissolved, reducing the temperature to 5°C, then placing for 24 hours to filtering out crystals, and drying the crystals to constant weight in an oven at 100°C under the protection of nitrogen. 170.6g of product A was obtained in this example, and the yield was 68.24%. The composition of resin acid was determined by gas chromatograph, as shown in table 1. (2)Weighing 100g of product A, then weighing 0.04g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 240 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 99.01g of product was obtained in this example, and the yield was 99.01%, and the reaction product yield (based on rosin) was calculated as follow: 68.24% 99.01%=67.56%.
The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in Table 2.
Comparative example 3:
The composition of masson pine rosin resin acid was determined by gas chromatograph, as shown in table 1.
Weighing 100g of slash rosin, then weighing 0.07g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 240 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 96.22g of product was obtained in this example, and the yield was 96.22%. The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in Table 2.
Comparative example 4: (1) Crushing 250g of slash rosin, putting it into a three-necked tlask equipped with reflux device, heating under the protection of nitrogen, then raising the temperature to 275°C and reacting for 20 minutes. Cooling down to 60°C, adding 700ml of mixture of ethyl acetate and methanol (25 °C, the volume ratio of ethyl acetate to methanol is 95:5), and raising the temperature to make the solution reflux. After the rosin is completely dissolved, reducing the temperature to 5°C, then placing for 24 hours to filtering out crystals, and drying the crystals to constant weight in an oven at 100°C under the protection of nitrogen. 156.2g of product A was obtained in this example, and the yield was 62.48%. The composition of resin acid was determined by gas chromatograph, as shown in table 1. (2) Weighing 100g of product A, then weighing 0.07g of palladium-carbon (palladium content 5%) by analytical balance, putting them in a three-necked flask, evacuating the air, injecting nitrogen to decompress and maintaining a small flow rate, then heating up to 290°C and keeping the temperature for 240 minutes. Cooling the material to 220°C and moving it to the filter to filter out the catalyst. 98.47g of product was obtained in this example, and the yield was 98.47%, and the reaction product yield (based on rosin) was calculated as follow: 62.48%x98.47%=61.52%.
The purity of the dehydroabietic acid product was measured by gas chromatograph, as shown in Table 2.
Table 1. pimaric | elliotin | sandar | isopi | palus | dehydr | levop | abieti | neoabi | abietic
Group acid oic acopim | maric | tric | oabieti | mari c etic acid acid aric acid | acid | c acid c acid acid resin acid acid acid
Comparative 9.37 2.24 1.63 | 2037 | 431 0.28 | 46.05 | 14.94 85.95 example 1
Comparative 481 0 1.85 0.72 | 898 5.07 0.19 | 72.43 | 5.02 91.69 example 2
Comparative 3.13 2.27 1.77 | 10.84 | 21.28 | 3.83 0.32 | 35.39 | 1934 80.16 example 3
Comparative 2.92 0 0.96 3.77 | 8.73 5.02 0.18 | 72.56 | 4.86 91.33 example 4
Table 2.
Example 1 93.26 70.37
Example 5 90.11 63.21
Comparative example 1 71.66 98.18
Comparative example 2 78.45 67.56
Comparative example 4 78.08
It can be seen that in the present invention, the rosin that the proportion of abietic resin acid in the total resin acid is 292% is used as raw material, the high-purity dehydroabietic acid with a purity of >90% will be obtained by the raw material reacting with the catalyst. The purity is extremely low if dehydroabietic acid is prepared directly from rosin. When the ratio of abietic acid-type resin acids in the total resin acid is less than 92%, the purity of dehydroabietic acid obtained by the same method decreases significantly.
It will be apparent to those skilled in the art that modifications and variations can be made without departing from the scope and spirit disclosed by the appended claims of the present disclosure, and such modifications and variations all fall in the protection extent of the claims of the present disclosure.
Claims (10)
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CN1317348C (en) * | 2004-09-27 | 2007-05-23 | 广西大学 | Method for producing pale disproportionated rosin with high content dehydroabietic acid and P-camphogen simultinuously |
CN101020630A (en) * | 2007-01-23 | 2007-08-22 | 广西民族大学 | Abietic acid preparing process |
CN102127369A (en) * | 2010-12-16 | 2011-07-20 | 广东科茂林产化工股份有限公司 | Method for preparing disproportionated rosin |
CN103436175B (en) * | 2013-08-27 | 2016-01-20 | 广西梧州松脂股份有限公司 | Improve the method for nilox resin dehydrogenation abietic acid content |
EP3085248B1 (en) * | 2015-04-22 | 2020-07-01 | Analyticon Discovery GmbH | Compositions comprising dehydro abietic acid |
CN105111940B (en) * | 2015-09-23 | 2017-11-14 | 广西科茂林化有限公司 | A kind of disproportionated rosin and preparation method thereof |
CN105622397B (en) * | 2016-01-06 | 2017-09-12 | 昆明理工大学 | A kind of method of purification of dehydroabietic acid |
CN107142024A (en) * | 2017-07-20 | 2017-09-08 | 广西容县宏旺树脂有限公司 | A kind of disproportionated rosin production technology of high dehydrogenation abietic acid |
CN112341329B (en) * | 2020-11-09 | 2023-07-25 | 广西科开成林科技有限公司 | Preparation method of high-purity abietic acid rosin |
CN113652171B (en) * | 2021-07-29 | 2022-12-06 | 广西大学 | Method for preparing disproportionated rosin with high dehydroabietic acid content |
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