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WO2018122700A1 - Production method of environmentally friendly chitosan from acrididae, tenebrionidae and gammaridae families - Google Patents

Production method of environmentally friendly chitosan from acrididae, tenebrionidae and gammaridae families Download PDF

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Publication number
WO2018122700A1
WO2018122700A1 PCT/IB2017/058279 IB2017058279W WO2018122700A1 WO 2018122700 A1 WO2018122700 A1 WO 2018122700A1 IB 2017058279 W IB2017058279 W IB 2017058279W WO 2018122700 A1 WO2018122700 A1 WO 2018122700A1
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Prior art keywords
acrididae
gammaridae
tenebrionidae
chitosan
families
Prior art date
Application number
PCT/IB2017/058279
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French (fr)
Inventor
Orhan ÖZCAN
İbrahim SERTDEMİR
Okşan KARAL YILMAZ
M. Naci YAZICIOĞLU
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Tubitak
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Filing date
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Publication of WO2018122700A1 publication Critical patent/WO2018122700A1/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
    • C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass

Definitions

  • the present invention relates to the production method of environmentally friendly chitosan.
  • the invention more particularly relates to the production method of chitosan which is environmentally friendly in terms of chemical factors and energy, from Acrididae (grashoppers), Tenebrionidae (darkling beetles, mealworms), and Gammaridae (Gammarus freshwater crustaceans) families, which are less likely to contain toxic or heavy metal compounds.
  • the thus obtained products principally include chitin and primary derivative thereof, chitosan.
  • Another biopolymer, chitosan has maintained its importance as a material of interest for the researchers especially in the last 50 years.
  • Chitosan which has many advantages when compared to chitin, is used in many industrial fields, primarily including food, cosmetics, agriculture, medicine, paper and textile industries. It has deemed necessary to develop various methods in order to obtain chitosan, whose area of use has expanded.
  • the Chinese Patent Application No. CN102037020 filed on 19.03.2008 within the state of the art discloses a method for producing chitosan from naturally occurring chitin-containing raw material, such as crustacean shells.
  • the products are first washed with a diluted hydrochloric acid mixture at a concentration of 3-4%. They are cleaned with water, and then aqueous sodium hydroxide at a concentration of 3 to 4% at 100°C is added for removing fat and protein, followed by washing the product again and drying.
  • aqueous sodium hydroxide at a concentration of 3 to 4% at 100°C is added for removing fat and protein, followed by washing the product again and drying.
  • chitin is placed at a 48% aqueous sodium hydroxide solution concentration and incubated for 6-8 hours. Afterwards, it is washed until neutralized. The resulting chitosan is dried.
  • demineralization is performed with 0.5N-0.1 N, i.e. 1.9-3.7 % HC1 in the method according to the invention and the used temperature is 50°C, not 100°C.
  • the deacetylation stage is performed with 48% NaOH for 6-8 hours at 100°C while in the method according to the invention, it is performed with 40% NaOH for 4 hours at 90°C.
  • heavy metal at PPM level is present here due to the use of sea-origin raw material, which is at PPB level in the method according to the invention. Further, the exemplified patent document does not mention depigmentation.
  • the Chinese Patent Application No. CN103665191A filed on 25.12.2013 within the state of the art discloses the production method of chitosan.
  • the shells are washed, dried, and then filtered. They are then soaked with hydrochloric acid. Afterwards, boiling with a sodium hydroxide solution, cooling and filtering are performed.
  • the protein removed shells are soaked with potassium permanganate. They are then subject to filtration, and subsequent to filtering the products, they are heated till complete decoloration. They are dried for forming chitin. Chitin is soaked with sodium hydroxide and cleaned. Once the hydroxide is removed, the product is dried and ground, thereby obtaining the chitosan.
  • KM11O 4 is used during deacetylation in the exemplified document and the use of said chemical is prohibited in Europe as well as in the USA. Moreover, the fact that the deacetylation occurs between 15-20 hours is associated with the used raw material. The harder chitin is, the longer the duration is.
  • the object of the present invention is to provide a production method of chitosan from Acrididae, Tenebrionidae and Gammaridae families.
  • Another object of the present invention is to provide an environmentally friendly chitosan production method with less energy and chemicals, using Acrididae, Tenebrionidae and Gammaridae families.
  • Another object of the present invention is to provide an environmentally friendly chitosan production method with low cost, using Acrididae, Tenebrionidae and Gammaridae families.
  • the method according to the invention is related to environmentally friendly chitosan production.
  • Dried organisms of Acrididae, Tenebrionidae and Gammaridae families are used as raw materials.
  • the method consists of seven main steps. The steps of the method are: making the organisms into powder form, pre-treating the powder in order to remove soluble organic and inorganic materials, removing lipids and soluble proteins, demineralization, deproteinization, and depigmentation and deacetylation for forming chitosan from chitin.
  • source organisms are selected from freshwater environment or edible insects.
  • the duration of depigmentation for obtaining an environmentally friendly, low-cost and high quality chitosan is shortened.
  • the invention is the production method of environmentally friendly chitosan from Acrididae, Tenebriomdae and Gammaridae families, wherein it comprises the steps of: making dead organisms of Acrididae, Tenebriomdae and Gammaridae families into powder form, boiling powdered organisms in water, removing lipids and soluble proteins, demineralization, deproteinization, depigmentation, deacetylation, and removing chitin in order to increase purity.
  • the organisms from Acrididae, Tenebriomdae and Gammaridae families, the chitin origin are made into powder form at 0.1-3 mm dimensions.
  • the powder is subject to pre-treatment so as to remove soluble organic and inorganic materials.
  • the chitin having been made into powder form is boiled with water for 1-4 hours (depending on the particle size) at 1-5 g powder/ 100 ml. After boiling, the organic phase with soluble substance content and the lipids accumulating on the water surface are removed.
  • the liquid in the aggregate that remains undissolved is removed as much as possible in order that it will not adversely affect the mineralization stage and that the used acid will be reduced.
  • deproteinization stage 5 g of demineralized insect waste is mixed with 100 ml of 2-5% NaOH for 2-4 hours at 50-70°C. After removing the liquid phase, the aggregate is first washed with 0.1N HC1 (0.1 Normality) and then with water. The base amount to be used is determined depending on the deproteinization temperature. First, longer deproteinization is useful for Acrididae family. Baseline base amount may be determined by measuring the pellet pH value with litmus paper.
  • decoloration step is also sufficient for depigmentation. In these cases, depigmentation steps can be omitted. It is not required to dry the pellet.
  • the decoloring solution is washed (50: EtOH 50: H 2 0 and 1 : H 2 0 2 ) in order to remove undissolved fraction pigments subsequent to the deproteinization step. Excessive H 2 0 2 is eliminated with water.
  • the use of lighter insects as raw material source means that H 2 0 2 is not required in the decoloring solution. Yellowish pinkish Gammaridae families do not require H 2 0 2 . It is because water and alcohol are not present when dried at 55°C. The darkening of the sample during the drying process results from excessive amount of H 2 0 2 or insufficient deproteinization. Therefore, the deproteinization step must be repeated.
  • the source organisms used here have a direct impact on the NaOH amount to be used. In case of a caterpillar pupa form, a more concentrated NaOH should be used.
  • Deacetylation is the step in which the chitin is turned into chitosan.
  • isolated chitin is dried.
  • 50 ml NaOH at 40% concentration is mixed for each g of chitin and incubated for 4 hours at 90°C (the temperature may be increased up to 150°C and thus the times period may be shortened).
  • the chitin/chitosan mixture is first washed with 0.1N HC1 (0.1 Normal HC1) and then with water.
  • the chitin/chitosan mixture is subject to 50°C for drying the same.
  • the dried mixture is mixed for 4-8 hours in the dark and dissolved in acetic acid.
  • the chitin-containing undissolved portion is removed.
  • the pH of the liquid portion is increased from pH 3-3.5 to pH 7.2-7.5 using 10% NaOH.
  • the chitin-chitosan mixture is made insoluble with this pH adjustment.
  • the liquid portion comprising chitosan is separated by physical methods, for example centrifuge or filtration. The remaining acetic acid is washed with water and removed.
  • lipids of Tenebrionidae family are edible, and thus they can be used not only in food but also in feed industry. The lipid content of such organisms can reach up to 30% of their weight.
  • the yield of the method is based on the source type. 100 g of the larval form of dried Tenebrio produces 25-35 g of edible oil. This oil can also be used as food additive for distilled alcoholic drinks such as tequila.
  • a 15-20 g of chitin/organic carbonate ash mixture is obtained for each 100 g of residue.
  • chitin is turned into chitosan
  • a mixture of 7 to 9 g containing chitosan, chitin and ash is obtained in the undissolved fraction.
  • the amount of ash varies between 15 and 20% of the mixture depending on the larval phase of the source. High yield chitin may be obtained in larvae molting period.
  • 100 g of the dried Acrididae yields in 30-35 g of locust leftovers which may be used as feed ingredient. 8.5 to 11 g of chitin-chitosan-ash mixture is obtained. The amount of chitosan varies between 2.5 and 4 g. During wing and late periods of adult Acrididae, high amounts of chitin/chitosan mixture is obtained.
  • chitin/ash per 100 g of dried organism is extracted after the deproteinization step.
  • the chitosan content in chitin-chitosan mixture is about 65%.
  • the solubility of acetic acid ensures that the final product weight of chitosan is as high as 84.6%.
  • Acrididae, Tenebrionidae and Gammaridae families can be produced at large amounts and they are commercially available.
  • the final product, chitosan is used in pharmaceutical, food and feed industries.
  • the by-products of the method are not toxic, which, in turn, makes such by-product suitable for use in feed and food industries.
  • the chemicals and materials used in this method are easy to obtain in bulk amounts.
  • the fact that only simple physical methods are utilized facilitates the method to be adjusted to large-scale fermenter systems.
  • the chemical agent amount and the total handling time is reduced; as a result, the production costs, time and required energy are also decreased. As a result, less waste material is produced reducing the cost of waste materials/wastes as well as the environmental problems.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
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  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

The invention relates to the production method of environmentally friendly - in terms of both chemical issues and energy - chitosan from Acrididae, Tenebnonidae and Gammaridae families, which are less likely to contain toxic or heavy metal compounds. The invention is the production method of environmentally friendly chitosan from Acrididae, Tenebrionidae and Gammaridae families, characterized by comprising the process steps of making dead organisms of Acrididae, Tenebrionidae and Gammaridae families into powder form, pre-treatment, removing lipids and soluble proteins, demineralization, deproteinization, depigmentation, deacetylation, and removing chitin in order to increase purity.

Description

DESCRIPTION
PRODUCTION METHOD OF ENVIRONMENTALLY FRIENDLY CHITOSAN FROM ACRIDIDAE, TENEBRIONIDAE AND
GAMMARIDAE FAMILIES Technical Field of the Invention
The present invention relates to the production method of environmentally friendly chitosan.
The invention more particularly relates to the production method of chitosan which is environmentally friendly in terms of chemical factors and energy, from Acrididae (grashoppers), Tenebrionidae (darkling beetles, mealworms), and Gammaridae (Gammarus freshwater crustaceans) families, which are less likely to contain toxic or heavy metal compounds.
Prior Art
Today, a considerable amount of crab and shrimp shells is wasted to the environment without being recycled by seafood products companies worldwide. With the recycling of wastes becoming a current issue during the recent years, crustacean/shell seafood products are not decomposed, instead they are recycled by chemical and biological methods and new products are obtained therefrom.
The thus obtained products principally include chitin and primary derivative thereof, chitosan. Another biopolymer, chitosan, has maintained its importance as a material of interest for the researchers especially in the last 50 years. Chitosan, which has many advantages when compared to chitin, is used in many industrial fields, primarily including food, cosmetics, agriculture, medicine, paper and textile industries. It has deemed necessary to develop various methods in order to obtain chitosan, whose area of use has expanded. The Chinese Patent Application No. CN102037020 filed on 19.03.2008 within the state of the art discloses a method for producing chitosan from naturally occurring chitin-containing raw material, such as crustacean shells. In this method, the products are first washed with a diluted hydrochloric acid mixture at a concentration of 3-4%. They are cleaned with water, and then aqueous sodium hydroxide at a concentration of 3 to 4% at 100°C is added for removing fat and protein, followed by washing the product again and drying. During deacetylation stage, chitin is placed at a 48% aqueous sodium hydroxide solution concentration and incubated for 6-8 hours. Afterwards, it is washed until neutralized. The resulting chitosan is dried. However, demineralization is performed with 0.5N-0.1 N, i.e. 1.9-3.7 % HC1 in the method according to the invention and the used temperature is 50°C, not 100°C. Not only the used chemical but also the consumed energy is less. The deacetylation stage is performed with 48% NaOH for 6-8 hours at 100°C while in the method according to the invention, it is performed with 40% NaOH for 4 hours at 90°C. At the same time, heavy metal at PPM level is present here due to the use of sea-origin raw material, which is at PPB level in the method according to the invention. Further, the exemplified patent document does not mention depigmentation.
The Chinese Patent Application No. CN103665191A filed on 25.12.2013 within the state of the art, on the other hand, discloses the production method of chitosan. In this method, the shells are washed, dried, and then filtered. They are then soaked with hydrochloric acid. Afterwards, boiling with a sodium hydroxide solution, cooling and filtering are performed. The protein removed shells are soaked with potassium permanganate. They are then subject to filtration, and subsequent to filtering the products, they are heated till complete decoloration. They are dried for forming chitin. Chitin is soaked with sodium hydroxide and cleaned. Once the hydroxide is removed, the product is dried and ground, thereby obtaining the chitosan. However, KM11O4 is used during deacetylation in the exemplified document and the use of said chemical is prohibited in Europe as well as in the USA. Moreover, the fact that the deacetylation occurs between 15-20 hours is associated with the used raw material. The harder chitin is, the longer the duration is.
The chemicals used in current techniques for the isolation and purification of chitosan are harmful to the human health and environment. As a result, it has become necessary to develop the production method of environmentally friendly chitosan from Acrididae, Tenebrionidae and Gammaridae families, which are less likely to contain toxic or heavy metal compounds, according to the invention.
Objects and Summary of the Invention
The object of the present invention is to provide a production method of chitosan from Acrididae, Tenebrionidae and Gammaridae families.
Another object of the present invention is to provide an environmentally friendly chitosan production method with less energy and chemicals, using Acrididae, Tenebrionidae and Gammaridae families.
Another object of the present invention is to provide an environmentally friendly chitosan production method with low cost, using Acrididae, Tenebrionidae and Gammaridae families.
The method according to the invention is related to environmentally friendly chitosan production. Dried organisms of Acrididae, Tenebrionidae and Gammaridae families are used as raw materials. The method consists of seven main steps. The steps of the method are: making the organisms into powder form, pre-treating the powder in order to remove soluble organic and inorganic materials, removing lipids and soluble proteins, demineralization, deproteinization, and depigmentation and deacetylation for forming chitosan from chitin. In order to reduce heavy metal and toxic compound contamination, source organisms are selected from freshwater environment or edible insects. In the method, while the HC1 and NaOH amount used in demineralization stage is reduced, the duration of depigmentation for obtaining an environmentally friendly, low-cost and high quality chitosan is shortened.
Detailed Description of the Invention
The invention is the production method of environmentally friendly chitosan from Acrididae, Tenebriomdae and Gammaridae families, wherein it comprises the steps of: making dead organisms of Acrididae, Tenebriomdae and Gammaridae families into powder form, boiling powdered organisms in water, removing lipids and soluble proteins, demineralization, deproteinization, depigmentation, deacetylation, and removing chitin in order to increase purity.
In this method, organisms from Acrididae, Tenebriomdae and Gammaridae families are used. The chitin in these organisms is less likely to present a multilayer structure. Therefore, the chemicals used in pre-treatment step may be reduced.
It is more advantageous to use small sizes in order to decrease the incubation time and temperature required for chitin extraction. Further, more successful results in de stage can be obtained by increasing the surface/volume ratio. As a consequence, in the first step the organisms from Acrididae, Tenebriomdae and Gammaridae families, the chitin origin, are made into powder form at 0.1-3 mm dimensions. The powder is subject to pre-treatment so as to remove soluble organic and inorganic materials. At this stage, the chitin having been made into powder form is boiled with water for 1-4 hours (depending on the particle size) at 1-5 g powder/ 100 ml. After boiling, the organic phase with soluble substance content and the lipids accumulating on the water surface are removed. The liquid in the aggregate that remains undissolved is removed as much as possible in order that it will not adversely affect the mineralization stage and that the used acid will be reduced.
During demineralization stage, 100 ml 0.05-0.1 N HC1 is used for 5 g of undissolved pellet, and then the liquid portion is received and the pellet is washed with water twice.
During deproteinization stage, on the other hand, 5 g of demineralized insect waste is mixed with 100 ml of 2-5% NaOH for 2-4 hours at 50-70°C. After removing the liquid phase, the aggregate is first washed with 0.1N HC1 (0.1 Normality) and then with water. The base amount to be used is determined depending on the deproteinization temperature. First, longer deproteinization is useful for Acrididae family. Baseline base amount may be determined by measuring the pellet pH value with litmus paper.
For nonpigmented season of the Gammaridae and nonpigmented form of the Tenebrionidae families, decoloration step is also sufficient for depigmentation. In these cases, depigmentation steps can be omitted. It is not required to dry the pellet.
It is very important to completely remove NaOH for depigmentation step. The decoloring solution is washed (50: EtOH 50: H20 and 1 : H202) in order to remove undissolved fraction pigments subsequent to the deproteinization step. Excessive H202 is eliminated with water. However, the use of lighter insects as raw material source means that H202 is not required in the decoloring solution. Yellowish pinkish Gammaridae families do not require H202. It is because water and alcohol are not present when dried at 55°C. The darkening of the sample during the drying process results from excessive amount of H202 or insufficient deproteinization. Therefore, the deproteinization step must be repeated. The source organisms used here have a direct impact on the NaOH amount to be used. In case of a caterpillar pupa form, a more concentrated NaOH should be used.
Deacetylation is the step in which the chitin is turned into chitosan. Here, isolated chitin is dried. In order to turn chitin into chitosan, 50 ml NaOH at 40% concentration is mixed for each g of chitin and incubated for 4 hours at 90°C (the temperature may be increased up to 150°C and thus the times period may be shortened). After removing the liquid phase, the chitin/chitosan mixture is first washed with 0.1N HC1 (0.1 Normal HC1) and then with water. The chitin/chitosan mixture is subject to 50°C for drying the same. The dried mixture is mixed for 4-8 hours in the dark and dissolved in acetic acid. The chitin-containing undissolved portion is removed. The pH of the liquid portion is increased from pH 3-3.5 to pH 7.2-7.5 using 10% NaOH. The chitin-chitosan mixture is made insoluble with this pH adjustment. The liquid portion comprising chitosan is separated by physical methods, for example centrifuge or filtration. The remaining acetic acid is washed with water and removed.
During chitosan production from Acrididae family, a high amount of protein is obtained. The by-products of this protein may be used in feed industry lowering the waste disposal costs, even providing an income. Similarly, the lipids of Tenebrionidae family are edible, and thus they can be used not only in food but also in feed industry. The lipid content of such organisms can reach up to 30% of their weight. The yield of the method is based on the source type. 100 g of the larval form of dried Tenebrio produces 25-35 g of edible oil. This oil can also be used as food additive for distilled alcoholic drinks such as tequila. After deproteinization step, a 15-20 g of chitin/organic carbonate ash mixture is obtained for each 100 g of residue. Once the chitin is turned into chitosan, a mixture of 7 to 9 g containing chitosan, chitin and ash is obtained in the undissolved fraction. The amount of ash varies between 15 and 20% of the mixture depending on the larval phase of the source. High yield chitin may be obtained in larvae molting period.
On the other hand, 100 g of the dried Acrididae yields in 30-35 g of locust leftovers which may be used as feed ingredient. 8.5 to 11 g of chitin-chitosan-ash mixture is obtained. The amount of chitosan varies between 2.5 and 4 g. During wing and late periods of adult Acrididae, high amounts of chitin/chitosan mixture is obtained.
For Gammarus pulex, 25-30 g of chitin/ash per 100 g of dried organism is extracted after the deproteinization step. Subsequent to deacetylation step, the chitosan content in chitin-chitosan mixture is about 65%. The solubility of acetic acid ensures that the final product weight of chitosan is as high as 84.6%.
Acrididae, Tenebrionidae and Gammaridae families can be produced at large amounts and they are commercially available. The final product, chitosan, is used in pharmaceutical, food and feed industries. The by-products of the method are not toxic, which, in turn, makes such by-product suitable for use in feed and food industries. The chemicals and materials used in this method are easy to obtain in bulk amounts. In addition, the fact that only simple physical methods are utilized facilitates the method to be adjusted to large-scale fermenter systems. The chemical agent amount and the total handling time is reduced; as a result, the production costs, time and required energy are also decreased. As a result, less waste material is produced reducing the cost of waste materials/wastes as well as the environmental problems.

Claims

The production method of environmentally friendly chitosan from Acrididae, Tenebrionidae and Gammaridae families, characterized in that it comprises the process steps of: making dead organisms of Acrididae, Tenebrionidae and Gammaridae families into powder form, boiling powdered organisms in water, removing lipids and soluble proteins, demineralization, deproteinization, depigmentation, deacetylation, and removing chitin in order to increase purity.
The production method of environmentally friendly chitosan from Acrididae, Tenebrionidae and Gammaridae families according to Claim 1, characterized in that acid is used during demineralization stage.
The production method of environmentally friendly chitosan from Acrididae, Tenebrionidae and Gammaridae families according to Claim 2, characterized in that the acid used during demineralization stage comprises 20 ml of 0.1 N HC1 per g of powder.
The production method of environmentally friendly chitosan from Acrididae, Tenebrionidae and Gammaridae families according to Claim 3, characterized in that the acid used during demineralization stage is incubated for at least 10 minutes. The production method of environmentally friendly chitosan from Acrididae, Tenebrionidae and Gammaridae families according to Claims 1 or 2, characterized in that alcohol is used during depigmentation stage.
The production method of environmentally friendly chitosan from Acrididae, Tenebrionidae and Gammaridae families according to Claim 5, characterized in that the alcohol used during depigmentation stage comprises 50% ethanol.
The production method of environmentally friendly chitosan from Acrididae, Tenebrionidae and Gammaridae families according to Claims 1 or 2 or 5, characterized in that the incubation period in deproteinization step is at least 4 hours.
PCT/IB2017/058279 2016-12-30 2017-12-21 Production method of environmentally friendly chitosan from acrididae, tenebrionidae and gammaridae families WO2018122700A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112992276A (en) * 2021-02-05 2021-06-18 滨州学院 Model and method for predicting chitosan yield in preparation of pillbug at different water bath temperatures

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991005808A1 (en) * 1989-10-20 1991-05-02 Firextra Oy Method for manufacture of chitosan and other products from shells of organisms, especially marine organisms
CA2201212A1 (en) * 1996-03-27 1997-09-27 Gaston Picard Process and apparatus for the recovery of chitin
US6310188B1 (en) * 2000-01-24 2001-10-30 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Method for producing chitin or chitosan
US20140275507A1 (en) * 2013-03-15 2014-09-18 Johannes van Leeuwen Processes for isolating chitin and chitosan from fungal biomass

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991005808A1 (en) * 1989-10-20 1991-05-02 Firextra Oy Method for manufacture of chitosan and other products from shells of organisms, especially marine organisms
CA2201212A1 (en) * 1996-03-27 1997-09-27 Gaston Picard Process and apparatus for the recovery of chitin
US6310188B1 (en) * 2000-01-24 2001-10-30 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Method for producing chitin or chitosan
US20140275507A1 (en) * 2013-03-15 2014-09-18 Johannes van Leeuwen Processes for isolating chitin and chitosan from fungal biomass

Non-Patent Citations (1)

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Title
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112992276A (en) * 2021-02-05 2021-06-18 滨州学院 Model and method for predicting chitosan yield in preparation of pillbug at different water bath temperatures
CN112992276B (en) * 2021-02-05 2022-10-18 滨州学院 Method for predicting yield of chitosan prepared by pillbug at different water bath temperatures

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