WO1995001838A1 - Charbons actives renfermant des groupes fonctionnels - Google Patents

Charbons actives renfermant des groupes fonctionnels Download PDF

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Publication number
WO1995001838A1
WO1995001838A1 PCT/GB1994/001452 GB9401452W WO9501838A1 WO 1995001838 A1 WO1995001838 A1 WO 1995001838A1 GB 9401452 W GB9401452 W GB 9401452W WO 9501838 A1 WO9501838 A1 WO 9501838A1
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WO
WIPO (PCT)
Prior art keywords
carbon
functional group
nucleophilic agent
group
temperature
Prior art date
Application number
PCT/GB1994/001452
Other languages
English (en)
Inventor
Richard James Holmes
Christopher Richard Hall
Original Assignee
The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland filed Critical The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland
Priority to JP7503901A priority Critical patent/JPH09500572A/ja
Priority to GB9600233A priority patent/GB2295826A/en
Priority to AU70786/94A priority patent/AU7078694A/en
Priority to EP94919763A priority patent/EP0708686A1/fr
Publication of WO1995001838A1 publication Critical patent/WO1995001838A1/fr

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Classifications

    • 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
    • B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/18—Carbon, coal or tar
    • 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
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
    • 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
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/24—Carbon, coal or tar
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography

Definitions

  • the present invention relates to the production of activated carbons that have functional groups associated with their surfaces, such that species specificity in adsorption processes may be achieved.
  • Preferred functional groups are borne upon organic chemical moieties.
  • the present inventors have previously described the production of chlorinated activated carbons that have age resistant properties when exposed to humid air, an agent that can be shown to degrade the materials adsorbent properties over time (Hall and Holmes: Carbon (1992) Vol 2. pp 173-176).
  • activated carbon samples at l8 ⁇ °C for 3 hours in a chlorine atmosphere, followed by washing with water or methanol, they were able to produce materials that at least as effective in adsorbing a model contaminant, trichloronitromethane, as the original activated carbon, even after having been pre -equilibrated by exposure to relative humidity of 80# (w/w) .
  • Results suggested that the materials were of enhanced adsorbent activity.
  • a method for producing carbon materials incorporating a functional group comprising halogenating a carbon containing material under conditions such that halogen is incorporated therein but remains displaceable by treatment with a nucleophilic agent, treating the halogenated carbon with a nucleophilic agent bearing the functional group, or a chemical precursor group therefor, to effect displacement of halogen to give a product in which the functional group remains associated with the carbon after heating at reduced pressure and/or washing with aqueous solvents.
  • Particularly preferred materials retain the functional group after heating at a temperature of 120°C and a pressure of 3 mbar.
  • Fluorine, chlorine, bromine and iodine can all be displaced from the surface of carbon with which they have been reacted.
  • bromination must be carried out at relatively high temperature (ca. 200°C) and is difficult to displace, whilst fluorine reacts with the surface and at the same time is absorbed by the carbon.
  • the slow release of absorbed fluorine results in a carbon of low surface stability and introduces a degree of hygroscopic character which is often undesirable.
  • Iodine is difficult to handle and is relatively unreactive.
  • chlorination may be carried out at low temperatures thus simplifying sample preparation and gas handling procedures.
  • Displaceable chlorine is provided in significant amounts depending upon the temperature of chlorination and is replaced with relative ease by contacting it with a liquid or vapour form of the nucleophilic agent.
  • Halogenation is preferably with chlorine or bromine, most preferably with chlorine. Chlorination is preferably carried out at 120°C or less, more preferably 85°C or less, and conveniently at 30°C or less, and is carried out, preferably, from 1 to several hours eg. 2-4 hours.
  • the nucleophilic agent may be a solid, liquid or gas, and may be any agent, organic or inorganic, that includes a group capable of displacement of the halogen from the carbon surface. It will be realised that while the term nucleophilic agent is used herein, the precise nature of the association of the agent with the carbon, and displacement of halogen, has not yet been elucidated and thus no limitation on the mechanism of reaction is placed upon the method of the present invention.
  • nucleophilic agent and thus the functional groups thereon, are retained on the carbon at reduced pressure and elevated temperature after such halogen pretreatment whereas without that it is not so retained and thus in time suffers loss of functional group content.
  • association of functional group bearing moieties with the carbon is increased with temperature in the displacement step, preferably being the reflux temperature of a liquid nucleophile or about 200°C.
  • nucleophilic agents examples include those of formula (I) :
  • each R is independently selected from H and optionally substituted alkyl or alkenyl groups, or two or more groups R include or form together one or more optionally substituted cycloalkyl, cycloalkenyl or heterocyclic groups; and n is equal to the valency of atom X minus 1 (with respect to the bond H-X) .
  • the functional groups to be associated with the carbon, or chemical precursors of these, will depend upon the properties desired of the end product modified carbon, and may include hydrophobic moieties, but most commonly will be groups such as amino, thiol, sulphonic or other sulphur oxide, halogen, carboxy, keto, aldehyde groups or groups specifically capable of being loaded with metal ions or atoms.
  • Other functional groups such as those taking the form of heterocyclic rings may also be substituents, eg. pyridine and piperidine rings.
  • chemical precursor as used here is intended to cover a moiety that is capable of undergoing chemical conversion to a desired group, eg. by oxidation or reduction, once associated with the carbon surface.
  • agents that are capable of associating with a carbon pretreated with a chlorine at low temperature to leave a substituted carbon surface resistant to outgassing at reduced pressure and elevated temperature in that they leave functional groups thereon, include alcohols or amines, eg. methanol, ammonia, ethanolamine, ethyla ine, ethylene diamine and isopropylamine.
  • alcohols or amines eg. methanol, ammonia, ethanolamine, ethyla ine, ethylene diamine and isopropylamine.
  • nucleophile that includes a moiety or moieties bearing the given group or its precursor, as well as a nucleophilic group which is used to achieve the association with the carbon.
  • nucleophile used may comprise such a moiety linked to a nucleophilic group by a spacer. This strategy is particularly applicable where steric problems may be encountered with a nucleophilic group such as that represented by the opposing nitrogens in piperazine.
  • pyridine, piperazine and triethylamine moieties may be associated with carbon using the method of the present invention by use of a compounds of Formula II a-c respectively as the nucleophile wherein X is OH or NH 2 or -SH in each case.
  • water may be used as a nucleophilic agent although the effect of hydroxy substituents on the carbon would be deleterious for most uses, including use as a filter agent for most noxious materials.
  • the nucleophilic agent is a gas
  • the cooled halogenated carbon is flushed with the nucleophilic gas and is then heated up to a treatment temperature gradually by ramping, eg. at about 5°C per minute, before heating at the treatment temperature for a period of some hours, eg. 3 _ 5 hours, where 1 bar pressure is used.
  • nucleophilic agent is a liquid it is preferred to reflux this at its boiling point with the carbon, for example in a air -excluded system.
  • the agent is methanol, ethanolamine pyridine, isopropylamine, triethylamine or ethylene diamine this method is preferred. Reflux is carried out conveniently for several hours.
  • nucleophilic agent is a solid it will be necessary to gasify it or to dissolve it a solvent in which it can be introduced to the surface of the carbon.
  • the functional group containing carbon product of the invention is washed alternately with acid and alkali and additionally with water to remove all reagents.
  • an odourless carbon is provided that shows significant amounts of elemental content corresponding to the nucleophilic agent, eg. nitrogen, where the amines are used.
  • Activated carbon samples (30g) were outgassed in an 81 stainless steel vessel for 3 hours at l8 ⁇ °C, cooled if required to the halogenation temperature, then >99# chlorine gas was introduced at a pressure of about 1 bar. After 24 hours the resultant chlorinated carbons were outgassed (3mbar, l8 ⁇ °C) to constant weight before being washed with the nucleophilic agent (flushed if gas) until the washings were no longer strongly acidic, usually 7 * 100ml, then treated at elevated temperature with a further 100ml for 8 hours, under reflux. Samples were dried to a constant weight at 120°C and 3 ⁇ bar.
  • BPL and SCII carbons were pretreated as described in Example 1 and then chlorinated at 30°C before being added to ethanolamine or ethylenediamine and heated under reflux for 8 hours. Carbons were decanted and then washed and outgassed as in 1 - 7 below.
  • the water adsorption properties of the modified carbons were consistent with the presence of additional polar functional groups of secondary amines and hydroxyl or secondary amine with ethylene diamine and ethanolamine as the nucleophilic agent respectively. These modified carbons adsorbed more water at RH values below ca 60% compared to the controls and the water adsorption capacity at high RH (ca. 90-95%) suggested that the modification did not result in significant loss of pore volume. Nitrogen adsorption figures showed that the treatments resulted in less than 10% decrease in total surface area. That the product carbons had a significantly increased content of chemisorbed amine was confirmed by elemental analysis and X-ray photoelectron spectroscopy. See Table 2.
  • the chlorinated/ethylenediamine, chlorinated/ethanolamine modified carbons adsorbed certain light gases which are known to react specifically with secondary amines more efficiently from high humidity air compared with control samples. It was also apparent that for ethanolamine the reaction with surface chlorine can take place either with the amine group or the hydroxyl group since the absorption performance of the ethylenediamine modified carbon against the gas was always greater; in this case a free secondary amine group should always be present. Carbons modified with amines (eg. dipropylamine) also absorbed methyl iodide from humid air more efficiently than unmodified controls.
  • Mass % is derived from atomic % EXAMPLE 3 (Comparative, .
  • Example 2 Similar experiments to those of Example 2 were performed using dimethylamine with essentially the same outcome. In some cases the carbon was treated with gaseous amine at 600°C but without prior chlorination. XPS and elemental analysis showed the treatment to result in a much smaller increase in nitrogen content compared to those of Example 2 where a chlorination step was included (see Tables 2 and 3). No increase in nitrogen content was observed when the carbon was exposed to the amine at ca. 200°C again without the chlorination step. This correlates well with Example 1 where it is seen that treatment with methanol or water did not affect carbon surface chemistry unless the chlorination step was included.
  • BPL carbons having either ethylenediamine or propylenediamine associated with their surface were prepared using a method as described in Example 2 modified in that the halogenation was carried out at 25°C and the number of bicarbonate washes was reduced to one.
  • BPL carbons having either ethylenediamine or 1,3-diaminopropane (propylenediamine) associated with their surfaces were prepared using a method as described in Example 2 modified in that the halogenation was carried out at 23°C and that the number of bicarbonate washes was reduced to one.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Carbon And Carbon Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production de charbons activés modifiés, dans lequel on traite le charbon activé dans une atmosphère contenant un halogène à une température inférieure à 180 °C. On traite ensuite le produit obtenu à l'aide d'un agent nucléophile, à température élevée. De préférence, l'halogénation est une chloration, et elle s'effectue de préférence à 120 °C ou moins, ou mieux à 85 °C ou moins et avantageusement à 30 °C ou moins. L'agent nucléophile peut être un liquide ou un gaz. Il peut s'agir de n'importe quel agent organique ou inorganique ayant un groupe capable d'effectuer un déplacement nucléophile de l'halogène, par exemple du chlore, de la surface du charbon. L'halogénation s'effectue en plusieurs heures, par exemple 24 heures. La présente invention concerne la production de charbons activés ayant des groupes fonctionnels associés à leur surface, ce qui permet d'obtenir une spécificité d'espèce dans des procédés d'adsorption.
PCT/GB1994/001452 1993-07-05 1994-07-05 Charbons actives renfermant des groupes fonctionnels WO1995001838A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP7503901A JPH09500572A (ja) 1993-07-05 1994-07-05 官能基を含む活性炭
GB9600233A GB2295826A (en) 1993-07-05 1994-07-05 Functional group containing activated carbons
AU70786/94A AU7078694A (en) 1993-07-05 1994-07-05 Functional group containing activated carbons
EP94919763A EP0708686A1 (fr) 1993-07-05 1994-07-05 Charbons actives renfermant des groupes fonctionnels

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9313871.7 1993-07-05
GB939313871A GB9313871D0 (en) 1993-07-05 1993-07-05 Substituted activated carbons

Publications (1)

Publication Number Publication Date
WO1995001838A1 true WO1995001838A1 (fr) 1995-01-19

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ID=10738319

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1994/001452 WO1995001838A1 (fr) 1993-07-05 1994-07-05 Charbons actives renfermant des groupes fonctionnels

Country Status (7)

Country Link
EP (1) EP0708686A1 (fr)
JP (1) JPH09500572A (fr)
CN (1) CN1129913A (fr)
AU (1) AU7078694A (fr)
CA (1) CA2166609A1 (fr)
GB (2) GB9313871D0 (fr)
WO (1) WO1995001838A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997047382A1 (fr) * 1996-06-14 1997-12-18 Cabot Corporation Adsorbants carbones modifies et procedes d'adsorption correspondants
US5885335A (en) * 1996-06-14 1999-03-23 Cabot Corporation Modified carbon products and inks and coatings containing modified carbon products
US5895522A (en) * 1997-08-12 1999-04-20 Cabot Corporation Modified carbon products with leaving groups and inks and coatings containing modified carbon products
US5922118A (en) * 1996-06-14 1999-07-13 Cabot Corporation Modified colored pigments and ink jet inks, inks, and coatings containing modified colored pigments
US6069190A (en) * 1996-06-14 2000-05-30 Cabot Corporation Ink compositions having improved latency
US6068688A (en) * 1997-11-12 2000-05-30 Cabot Corporation Particle having an attached stable free radical and methods of making the same
US6103380A (en) * 1998-06-03 2000-08-15 Cabot Corporation Particle having an attached halide group and methods of making the same
US6337358B1 (en) 1997-10-31 2002-01-08 Cabot Corporation Particles having an attached stable free radical, polymerized modified particles, and methods of making the same
US6368239B1 (en) 1998-06-03 2002-04-09 Cabot Corporation Methods of making a particle having an attached stable free radical
US6472471B2 (en) 1997-12-16 2002-10-29 Cabot Corporation Polymeric products containing modified carbon products and methods of making and using the same
US6787029B2 (en) 2001-08-31 2004-09-07 Cabot Corporation Material for chromatography
WO2005018802A2 (fr) * 2003-08-25 2005-03-03 Cabot Corporation Compositions et materiaux de chromatographie pour la separation biologique
CN103071457A (zh) * 2013-01-15 2013-05-01 中国科学院青海盐湖研究所 凝胶型碘离子吸附剂、其制备方法及应用
KR101405481B1 (ko) 2012-10-09 2014-07-01 재단법인 포항산업과학연구원 활성탄소섬유 제조방법 및 이에 의해 제조되는 활성탄소섬유
US10086357B2 (en) 2016-04-05 2018-10-02 Hyundai Motor Company Method for manufacturing activated carbon
US11155465B2 (en) 2015-04-22 2021-10-26 Stella Chemifa Corporation Cross-linked structure of carbon material and method for producing same

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KR101588768B1 (ko) 2014-10-27 2016-01-26 현대자동차 주식회사 활성탄소 및 그 제조방법
CN111013533A (zh) * 2019-12-10 2020-04-17 华东理工大学 一种净化甲醛的改性活性炭及其制备方法
CN113893651A (zh) * 2021-11-24 2022-01-07 内蒙古国华呼伦贝尔发电有限公司 重金属脱除系统、重金属脱除方法及烟气处理系统

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR835371A (fr) * 1937-03-17 1938-12-20 Carbo Norit Union Verwaltungs Procédé pour préparer un agent adsorbant stable à la chaleur
FR1086491A (fr) * 1952-08-04 1955-02-14 Procédé de fabrication d'un charbon actif ayant le pouvoir d'échanger des cations
DE938308C (de) * 1952-06-28 1956-01-26 Bayer Ag Verfahren zur Herstellung von Aktivkohle
EP0031586A2 (fr) * 1979-12-26 1981-07-08 Rohm And Haas Company Adsorbants fonctionnalisés à base de carbone, pouvant être des matériaux d'échange d'ions ou des précurseurs de ceux-ci, procédés pour leur fabrication et leur utilisation
EP0486015A1 (fr) * 1990-11-16 1992-05-20 Nippondenso Co., Ltd. Charbon actif pour la déodorisation et procédé de fabrication

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR835371A (fr) * 1937-03-17 1938-12-20 Carbo Norit Union Verwaltungs Procédé pour préparer un agent adsorbant stable à la chaleur
DE938308C (de) * 1952-06-28 1956-01-26 Bayer Ag Verfahren zur Herstellung von Aktivkohle
FR1086491A (fr) * 1952-08-04 1955-02-14 Procédé de fabrication d'un charbon actif ayant le pouvoir d'échanger des cations
EP0031586A2 (fr) * 1979-12-26 1981-07-08 Rohm And Haas Company Adsorbants fonctionnalisés à base de carbone, pouvant être des matériaux d'échange d'ions ou des précurseurs de ceux-ci, procédés pour leur fabrication et leur utilisation
EP0486015A1 (fr) * 1990-11-16 1992-05-20 Nippondenso Co., Ltd. Charbon actif pour la déodorisation et procédé de fabrication

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5885335A (en) * 1996-06-14 1999-03-23 Cabot Corporation Modified carbon products and inks and coatings containing modified carbon products
US5922118A (en) * 1996-06-14 1999-07-13 Cabot Corporation Modified colored pigments and ink jet inks, inks, and coatings containing modified colored pigments
AU720312B2 (en) * 1996-06-14 2000-05-25 Cabot Corporation Modified carbon adsorbents and processes for adsorption using the same
US6069190A (en) * 1996-06-14 2000-05-30 Cabot Corporation Ink compositions having improved latency
WO1997047382A1 (fr) * 1996-06-14 1997-12-18 Cabot Corporation Adsorbants carbones modifies et procedes d'adsorption correspondants
US5895522A (en) * 1997-08-12 1999-04-20 Cabot Corporation Modified carbon products with leaving groups and inks and coatings containing modified carbon products
US5968243A (en) * 1997-08-12 1999-10-19 Belmont; James A. Modified carbon products with leaving groups inks and coatings containing modified carbon products
US6337358B1 (en) 1997-10-31 2002-01-08 Cabot Corporation Particles having an attached stable free radical, polymerized modified particles, and methods of making the same
US6068688A (en) * 1997-11-12 2000-05-30 Cabot Corporation Particle having an attached stable free radical and methods of making the same
US6472471B2 (en) 1997-12-16 2002-10-29 Cabot Corporation Polymeric products containing modified carbon products and methods of making and using the same
US7282526B2 (en) 1998-06-03 2007-10-16 Cabot Corporation Particle having an attached halide group and methods of making the same
US6368239B1 (en) 1998-06-03 2002-04-09 Cabot Corporation Methods of making a particle having an attached stable free radical
US6103380A (en) * 1998-06-03 2000-08-15 Cabot Corporation Particle having an attached halide group and methods of making the same
US6551393B2 (en) 1998-06-03 2003-04-22 Cabot Corporation Methods of making a particle having an attached stable free radical
US6664312B2 (en) 1998-06-03 2003-12-16 Cabot Corporation Particle having an attached halide group and methods of making the same
US6350519B1 (en) 1998-06-03 2002-02-26 Cabot Corporation Particle having an attached halide group and methods of making the same
US6787029B2 (en) 2001-08-31 2004-09-07 Cabot Corporation Material for chromatography
US7951297B2 (en) 2001-08-31 2011-05-31 Cabot Corporation Material for chromatography
US7008534B2 (en) 2001-08-31 2006-03-07 Cabot Corporation Material for chromatography
US7195713B2 (en) 2001-08-31 2007-03-27 Cabot Corporation Material for chromatography
WO2005018802A3 (fr) * 2003-08-25 2006-10-05 Cabot Corp Compositions et materiaux de chromatographie pour la separation biologique
WO2005018802A2 (fr) * 2003-08-25 2005-03-03 Cabot Corporation Compositions et materiaux de chromatographie pour la separation biologique
KR101405481B1 (ko) 2012-10-09 2014-07-01 재단법인 포항산업과학연구원 활성탄소섬유 제조방법 및 이에 의해 제조되는 활성탄소섬유
CN103071457A (zh) * 2013-01-15 2013-05-01 中国科学院青海盐湖研究所 凝胶型碘离子吸附剂、其制备方法及应用
US11155465B2 (en) 2015-04-22 2021-10-26 Stella Chemifa Corporation Cross-linked structure of carbon material and method for producing same
US10086357B2 (en) 2016-04-05 2018-10-02 Hyundai Motor Company Method for manufacturing activated carbon

Also Published As

Publication number Publication date
GB9600233D0 (en) 1996-03-20
AU7078694A (en) 1995-02-06
GB2295826A (en) 1996-06-12
CA2166609A1 (fr) 1995-01-19
CN1129913A (zh) 1996-08-28
JPH09500572A (ja) 1997-01-21
GB9313871D0 (en) 1993-08-18
EP0708686A1 (fr) 1996-05-01

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