WO2018056927A2 - An arsenic adsorbent and a method for obtaining thereof - Google Patents

An arsenic adsorbent and a method for obtaining thereof Download PDF

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Publication number
WO2018056927A2
WO2018056927A2 PCT/TR2017/000079 TR2017000079W WO2018056927A2 WO 2018056927 A2 WO2018056927 A2 WO 2018056927A2 TR 2017000079 W TR2017000079 W TR 2017000079W WO 2018056927 A2 WO2018056927 A2 WO 2018056927A2
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Prior art keywords
gma
plasma
cellulose
treating
radicals
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PCT/TR2017/000079
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French (fr)
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WO2018056927A3 (en
Inventor
Pinar AKKAS KAVAKLI
Cengiz KAVAKLI
Serdar KORPAYEV
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Akkas Kavakli Pinar
Kavakli Cengiz
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Publication of WO2018056927A2 publication Critical patent/WO2018056927A2/en
Publication of WO2018056927A3 publication Critical patent/WO2018056927A3/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
    • C08F251/02—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof on to cellulose or derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3206—Organic carriers, supports or substrates
    • B01J20/3208—Polymeric carriers, supports or substrates
    • B01J20/3212—Polymeric carriers, supports or substrates consisting of a polymer obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3268—Macromolecular compounds
    • B01J20/3272—Polymers obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3268—Macromolecular compounds
    • B01J20/3278—Polymers being grafted on the carrier
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3268—Macromolecular compounds
    • B01J20/328—Polymers on the carrier being further modified
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/28—Treatment of water, waste water, or sewage by sorption
    • C02F1/286—Treatment of water, waste water, or sewage by sorption using natural organic sorbents or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/46—Treatment of water, waste water, or sewage by electrochemical methods
    • C02F1/4608—Treatment of water, waste water, or sewage by electrochemical methods using electrical discharges
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
    • C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/28—Treatment by wave energy or particle radiation
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/10—Inorganic compounds
    • C02F2101/103—Arsenic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
    • C08J2301/02—Cellulose; Modified cellulose

Definitions

  • the present invention relates to an arsenic adsorbent which can be used as filter or sensor for removing heavy metals such as particularly arsenic (V) from environmental waste waters and a method which is used for obtaining this adsorbent.
  • V arsenic
  • the Chinese patent document no. CN102139202 discloses an adsorbent with cellulose content for removing arsenic and fluoride ions in water and a method for preparing this adsorbent.
  • a polyolefin containing an amino group is grafted on cellulose surface by using cerium ammonium nitrate as initiator in order that it has electrostatic interaction with As(III) and As(V) ions in water.
  • Graft polymerization of natural cellulose fibers with monomers containing amino group of hydroxyl derivatives is disclosed in the said document.
  • An objective of the present invention is to realize an arsenic adsorbent obtained by using cotton cellulose which does not exhibit any adverse effect on environment and human health, can be modified easily and which is a natural polymer; and a method for obtaining this adsorbent.
  • Another objective of the present invention is to realize an arsenic adsorbent wherein cotton cellulose -which is abundant in nature and particularly in Turkey and biocompatible with living organisms and tissues- is used; and a method for obtaining this adsorbent.
  • Another objective of the present invention is to realize an arsenic adsorbent which is environmentally harmless, can be obtained and recycled easily, and which is biodegradable after use; and a method for obtaining this adsorbent.
  • Another objective of the present invention is to realize an arsenic adsorbent which has high As(V) ions-holding capability; and a method for obtaining this adsorbent.
  • Another objective of the present invention is to realize an economical and environmentally harmless method for obtaining an arsenic adsorbent via modification of cotton cellulose -which is a natural polymer- by generating free radicals by means of plasma technique -which is one of cheap methods- and using water instead of organic solvent in emulsion medium.
  • Figure 1 is a flow chart of the inventive method.
  • the inventive method ( 100) comprises steps of:
  • GMA giycidyl methacrylate
  • surface radicals are generated by pre-treating cellulose with at least one plasma at a predetermined plasma atmosphere, pressure, power and processing time ( 101).
  • cellulose is treated with plasma at Ar-plasma medium. 0.2 mbar pressure, 60 watt power and for 60 seconds (101).
  • GMA glycidyl methacrylate
  • GMA grafting time (102) is carried out in the presence of surface active agent by using preferably water as solvent instead of organic solvents in emulsion medium.
  • polyethylene glycol sorbitan monolaurate (Tween20) is used as surface active agent.
  • Grafting glycidyl methacrylate (GMA) monomer to the cellulose -on which radicals are generated by pre-treating with plasma- by means of graft polymerization method by using surface active agent in emulsion medium ( 102) is carried out preferably at 40°C temperature, 3% GMA concentration for 2 hours.
  • the GMA grafted cellulose chain is modified with ethvlenediamine (EDA) by opening GMA epoxy chain (103).
  • EDA ethvlenediamine
  • Modifying the GMA grafted cellulose chain with ethvlenediamine by opening GMA epoxy chain ( 103) has 97% (3.48 mmol EDA/g polymer) yield.
  • a cellulosic arsenic adsorbent grafted with glycidyl methacrylate (GMA) and modified with ethylenediamine (EDA) is obtained by plasma technique (Schematic diagram 1 ).
  • the said arsenic adsorbent has 155 mg As(V)/g adsorbent adsorption value by reaching balance at pH 3 value within 250 ppm As(V) solution in 3 hours.
  • Schematic diagram 1 Schematic diagram about obtaining the inventive adsorbent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Electrochemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)

Abstract

The present invention relates to an arsenic adsorbent which can be used as filter or sensor for removing heavy metals such as particularly arsenic (V) from environmental waste waters and a method which is used for obtaining this adsorbent.

Description

AN ARSENIC ADSORBENT AND A METHOD FOR OBTAINING
THEREOF
Technical Field
The present invention relates to an arsenic adsorbent which can be used as filter or sensor for removing heavy metals such as particularly arsenic (V) from environmental waste waters and a method which is used for obtaining this adsorbent.
Background of the Invention Today, recycling of waste waters is of great importance due to the fact that water resources gradually decrease. Soluble, unsoluble. inorganic, reduced, oxidized, precipitated, absorbed or free metals are usually included in waste waters. A wide range of methods such as adsorption, ion exchange, precipitation-coprecipitation and membrane filtration are used in order to remove these materials included in waste waters threatening human health. However, studies are carried on so as to develop environmental and economic approaches for these applications.
The Chinese patent document no. CN102139202, an application in the state of the art. discloses an adsorbent with cellulose content for removing arsenic and fluoride ions in water and a method for preparing this adsorbent. In the invention described in the said document, a polyolefin containing an amino group is grafted on cellulose surface by using cerium ammonium nitrate as initiator in order that it has electrostatic interaction with As(III) and As(V) ions in water. Graft polymerization of natural cellulose fibers with monomers containing amino group of hydroxyl derivatives is disclosed in the said document. The article titled as '"Synthesis and Characterization of Multi-amino- functionalized Cellulose for Arsenic Adsorption (2013)" (Carbohydrate Polymers, 92, 380- 387) in the state of the art discloses preparation of modified cellulose derivative modified by amine group and use of this product as arsenic adsorbent. In the invention described in the said document, cotton is grafted on cellulose surface with glycidyl methacrylate chemical method by using cerium ammonium nitrate. Then, it is modified with tetraethylenepentamine by ring opening Summary of the Invention
An objective of the present invention is to realize an arsenic adsorbent obtained by using cotton cellulose which does not exhibit any adverse effect on environment and human health, can be modified easily and which is a natural polymer; and a method for obtaining this adsorbent.
Another objective of the present invention is to realize an arsenic adsorbent wherein cotton cellulose -which is abundant in nature and particularly in Turkey and biocompatible with living organisms and tissues- is used; and a method for obtaining this adsorbent.
Another objective of the present invention is to realize an arsenic adsorbent which is environmentally harmless, can be obtained and recycled easily, and which is biodegradable after use; and a method for obtaining this adsorbent.
Another objective of the present invention is to realize an arsenic adsorbent which has high As(V) ions-holding capability; and a method for obtaining this adsorbent.
Another objective of the present invention is to realize an economical and environmentally harmless method for obtaining an arsenic adsorbent via modification of cotton cellulose -which is a natural polymer- by generating free radicals by means of plasma technique -which is one of cheap methods- and using water instead of organic solvent in emulsion medium.
Detailed Description of the Invention
"An Arsenic Adsorbent and a Method for Obtaining Thereof1 realized to fulfil the objectives of the present invention is shown in the figure attached, in which:
Figure 1 is a flow chart of the inventive method.
The components illustrated in the figure are individually numbered, where the numbers refer to the following:
The inventive method ( 100) comprises steps of:
- generating surface radicals by pre-treating cellulose with at least one plasma at a predetermined plasma atmosphere, pressure, power -and processing time ( 101 );
- grafting at least one giycidyl methacrylate (GMA) monomer to the cellulose -on which radicals are generated by pre-treating with plasma- by means of graft polymerization method by using surface active agent in emulsion medium at a predetermined temperature, concentration and grafting time ( 102);
- modifying the GMA grafted cellulose chain with ethylenediamine by opening GMA epoxy chain ( 103).
In the inventive method (100), surface radicals are generated by pre-treating cellulose with at least one plasma at a predetermined plasma atmosphere, pressure, power and processing time ( 101). In one preferred embodiment of the inventive method (100), cellulose is treated with plasma at Ar-plasma medium. 0.2 mbar pressure, 60 watt power and for 60 seconds (101). In the inventive method (100), glycidyl methacrylate (GMA) is grafted to the cellulose -which is pre-treated with plasma and surface radicals of which are generated- by means of graft polymerization method (102). In the said method ( 100), GMA grafting time (102) is carried out in the presence of surface active agent by using preferably water as solvent instead of organic solvents in emulsion medium. In one preferred embodiment of the inventive method (100), polyethylene glycol sorbitan monolaurate (Tween20") is used as surface active agent. Grafting glycidyl methacrylate (GMA) monomer to the cellulose -on which radicals are generated by pre-treating with plasma- by means of graft polymerization method by using surface active agent in emulsion medium ( 102) is carried out preferably at 40°C temperature, 3% GMA concentration for 2 hours.
In the inventive method (100), the GMA grafted cellulose chain is modified with ethvlenediamine (EDA) by opening GMA epoxy chain (103). Modifying the GMA grafted cellulose chain with ethvlenediamine by opening GMA epoxy chain ( 103) has 97% (3.48 mmol EDA/g polymer) yield.
With the inventive method ( 100), a cellulosic arsenic adsorbent grafted with glycidyl methacrylate (GMA) and modified with ethylenediamine (EDA) is obtained by plasma technique (Schematic diagram 1 ). The said arsenic adsorbent has 155 mg As(V)/g adsorbent adsorption value by reaching balance at pH 3 value within 250 ppm As(V) solution in 3 hours.
COTTON CELLULOSE
Plasma
Figure imgf000006_0001
COTTON CELLULOSE
Schematic diagram 1. Schematic diagram about obtaining the inventive adsorbent.
Within these basic concepts; it is possible to develop various embodiments of the inventive "An Arsenic Adsorbent and a Method for Obtaining Thereof ( 100)", the invention cannot be limited to examples disclosed herein and it is essentially according to claims.

Claims

A method (100) characterized by steps of:
generating surface radicals by pre-treating cellulose with at least one plasma at a predetermined plasma atmosphere, pressure, power and processing time (101 );
grafting at least one glycidyl methacrylate (GMA) monomer to the cellulose -on which radicals are generated by pre-treating with plasma- by means of graft polymerization method by using surface active agent in emulsion medium at a predetermined temperature, concentration and grafting time ( 102); and
modifying the GMA grafted cellulose chain with ethylenediamine by opening GMA epoxy chain (103)
A method (100) according to Claim 1 ; characterized by the step of generating surface radicals by pre-treating with at least one plasma at Ar- plasma medium ( 101).
A method (100) according to Claim 1 or 2; characterized by the step of generating surface radicals by pre-treating with at least one plasma at 0.2 mbar pressure (101).
A method (100) according to any of the preceding claims; characterized by the step of generating surface radicals by pre-treating with at least one plasma at 60 watt power (101).
5. A method (100) according to any of the preceding claims; characterized by the step of generating surface radicals by pre-treating with at least one plasma for 60 seconds (101 ).
6. A method (100) according to any of the preceding claims; characterized by the step of grafting at least one glycidyl methacrylate (GMA) monomer to the cellulose -solvent of which is water- by means of graft polymerization method by using surface active agent in emulsion medium at a predetermined temperature, concentration and grafting time ( 102).
7. A method (100) according to any of the preceding claims; characterized by the step of grafting at least one glycidyl methacrylate (GMA) monomer to the cellulose -wherein polyethylene glycol sorbitan monolaurate (Tween20 ) is used as a surface active- by means of graft polymerization method in emulsion medium (102).
8. A method (100) according to any of the preceding claims; characterized by the step of grafting at least one glycidyl methacrylate (GMA) monomer to the cellulose -on surface of which radicals are generated by pre-treating with plasma- by means of graft polymerization method in emulsion medium by using surface active agent at 40°C temperature ( 102).
9. A method (100) according to any of the preceding claims; characterized by the step of grafting at least one glycidyl methacrylate (GMA) monomer to the cellulose -on surface of which radicals are generated by pre-treating with plasma- by means of graft polymerization method in emulsion medium by using surface active agent at 3% concentration (102).
10. A method (100) according to any of the preceding claims; characterized by the step of grafting at least one glycidyl methacrylate (GMA) monomer to the cellulose -on surface of which radicals are generated by pre-treating with plasma- by means of graft polymerization method in emulsion medium by using surface active agent for 2 hours (102).
1 1. A method ( 100) according to any of the preceding claims; characterized by the step of modifying the GMA grafted cellulose chain -which has 97% (3.48 mmol EDA/g polymer) yield- with ethyl enedi amine by opening GMA epoxy chain ( 103)
12. A cellulosic arsenic adsorbent obtained by a method according to any of the preceding claims; which is grafted with glycidyl methacrylate (GMA) and modified with ethylenediamine (EDA).
13. A cellulosic arsenic adsorbent which is grafted with glycidyl methacrylate
(GMA) and modified with ethylenediamine (EDA).
14. An arsenic adsorbent according to Claim 13; which has 155 mg As(V)/g adsorbent adsorption value by reaching balance at pH 3 value and within 250 ppm As(V) solution in 3 hours.
PCT/TR2017/000079 2016-07-19 2017-07-12 An arsenic adsorbent and a method for obtaining thereof WO2018056927A2 (en)

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TR201610010 2016-07-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115722214A (en) * 2022-12-07 2023-03-03 东莞市亿茂滤材有限公司 Ammonia gas removing resin material and preparation method thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102139202A (en) 2010-01-28 2011-08-03 中国科学院理化技术研究所 Cellulose base adsorption material used for removing arsenic ions and fluoric ions in water and preparation method thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5082038B2 (en) * 2007-03-23 2012-11-28 独立行政法人日本原子力研究開発機構 Graft-polymerized functional nonwoven fabric filter and method for producing the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102139202A (en) 2010-01-28 2011-08-03 中国科学院理化技术研究所 Cellulose base adsorption material used for removing arsenic ions and fluoric ions in water and preparation method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Synthesis and Characterization of Multi-amino-functionalized Cellulose for Arsenic Adsorption", CARBOHYDRATE POLYMERS, vol. 92, 2013, pages 380 - 387

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115722214A (en) * 2022-12-07 2023-03-03 东莞市亿茂滤材有限公司 Ammonia gas removing resin material and preparation method thereof
CN115722214B (en) * 2022-12-07 2024-03-29 东莞市亿茂滤材有限公司 Ammonia-removal resin material and preparation method thereof

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