EP2928604A1 - Résine échangeuse d'ions à propriétés chélatantes, son procédé de préparation et ses utilisations - Google Patents
Résine échangeuse d'ions à propriétés chélatantes, son procédé de préparation et ses utilisationsInfo
- Publication number
- EP2928604A1 EP2928604A1 EP13801541.7A EP13801541A EP2928604A1 EP 2928604 A1 EP2928604 A1 EP 2928604A1 EP 13801541 A EP13801541 A EP 13801541A EP 2928604 A1 EP2928604 A1 EP 2928604A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- resin
- phenolic
- group
- formaldehyde
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000003456 ion exchange resin Substances 0.000 title claims abstract description 15
- 229920003303 ion-exchange polymer Polymers 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims abstract description 13
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000011347 resin Substances 0.000 claims abstract description 64
- 229920005989 resin Polymers 0.000 claims abstract description 64
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 54
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000000178 monomer Substances 0.000 claims abstract description 51
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 33
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 31
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000012736 aqueous medium Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 8
- 239000002609 medium Substances 0.000 claims abstract description 8
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 14
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 4
- YVGKLVZOQWYWTI-UHFFFAOYSA-N calixresorc[4]arene Chemical compound C1C(C(=CC=2O)O)=CC=2CC(C(=CC=2O)O)=CC=2CC(=C2)C(O)=CC(O)=C2CC2=CC1=C(O)C=C2O YVGKLVZOQWYWTI-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 3
- RUESGWAQQFPVIF-UHFFFAOYSA-N 2,3,4-trihydroxybenzenesulfonic acid Chemical class OC1=CC=C(S(O)(=O)=O)C(O)=C1O RUESGWAQQFPVIF-UHFFFAOYSA-N 0.000 claims description 2
- 241001120493 Arene Species 0.000 claims description 2
- VZJNFKPOGDRXBL-UHFFFAOYSA-N P(O)(O)=O.OC=1C(=C(C=CC1)O)O Chemical class P(O)(O)=O.OC=1C(=C(C=CC1)O)O VZJNFKPOGDRXBL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003637 basic solution Substances 0.000 claims description 2
- VERMEZLHWFHDLK-UHFFFAOYSA-N benzene-1,2,3,4-tetrol Chemical compound OC1=CC=C(O)C(O)=C1O VERMEZLHWFHDLK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001896 cresols Chemical class 0.000 claims description 2
- 229960001553 phloroglucinol Drugs 0.000 claims description 2
- 229940079877 pyrogallol Drugs 0.000 claims description 2
- 150000005170 trihydroxybenzoic acids Chemical class 0.000 claims description 2
- 150000003739 xylenols Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000003381 solubilizing effect Effects 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000005202 decontamination Methods 0.000 abstract description 5
- 230000003588 decontaminative effect Effects 0.000 abstract description 5
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 28
- -1 cesium ions Chemical class 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 238000000605 extraction Methods 0.000 description 13
- 150000001408 amides Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 6
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 6
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 229960003330 pentetic acid Drugs 0.000 description 6
- 239000013535 sea water Substances 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229960003742 phenol Drugs 0.000 description 5
- 238000012958 reprocessing Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 239000003758 nuclear fuel Substances 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229960003732 tyramine Drugs 0.000 description 4
- DZGWFCGJZKJUFP-UHFFFAOYSA-O tyraminium Chemical group [NH3+]CCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-O 0.000 description 4
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 101100496858 Mus musculus Colec12 gene Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 229910052746 lanthanum Inorganic materials 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229960003540 oxyquinoline Drugs 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RDJUHLUBPADHNP-UHFFFAOYSA-N 1,2,3,5-tetrahydroxybenzene Chemical compound OC1=CC(O)=C(O)C(O)=C1 RDJUHLUBPADHNP-UHFFFAOYSA-N 0.000 description 2
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- GPDXFYPVHRESMA-UHFFFAOYSA-N 2,4,5-trihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=C(O)C=C1O GPDXFYPVHRESMA-UHFFFAOYSA-N 0.000 description 2
- IBHWREHFNDMRPR-UHFFFAOYSA-N 2,4,6-Trihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 description 2
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
- FAXWFCTVSHEODL-UHFFFAOYSA-N 2,4-dibromophenol Chemical compound OC1=CC=C(Br)C=C1Br FAXWFCTVSHEODL-UHFFFAOYSA-N 0.000 description 2
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-UHFFFAOYSA-N 0.000 description 2
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GVLDWRAOOIKSMW-UHFFFAOYSA-N OP(O)=O.OC1=CC=CC=C1O Chemical compound OP(O)=O.OC1=CC=CC=C1O GVLDWRAOOIKSMW-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000975 co-precipitation Methods 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229960001484 edetic acid Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YIDVLWDHYNWHMH-UHFFFAOYSA-N (4-hydroxyphenyl)phosphonic acid Chemical compound OC1=CC=C(P(O)(O)=O)C=C1 YIDVLWDHYNWHMH-UHFFFAOYSA-N 0.000 description 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- NXEQAZTWIDXTKX-UHFFFAOYSA-N 1,6-dihydroxycyclohexa-2,4-diene-1-sulfonic acid Chemical compound OC1C=CC=CC1(O)S(O)(=O)=O NXEQAZTWIDXTKX-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- BRRSNXCXLSVPFC-UHFFFAOYSA-N 2,3,4-Trihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1O BRRSNXCXLSVPFC-UHFFFAOYSA-N 0.000 description 1
- OUCSIUCEQVCDEL-UHFFFAOYSA-N 2,3,4-tribromophenol Chemical compound OC1=CC=C(Br)C(Br)=C1Br OUCSIUCEQVCDEL-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- IJGSULQFKYOYEU-UHFFFAOYSA-N 2,3,4-trifluorophenol Chemical compound OC1=CC=C(F)C(F)=C1F IJGSULQFKYOYEU-UHFFFAOYSA-N 0.000 description 1
- JOELYYRJYYLNRR-UHFFFAOYSA-N 2,3,5-trihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1O JOELYYRJYYLNRR-UHFFFAOYSA-N 0.000 description 1
- VCNCNAPAHSSWCI-UHFFFAOYSA-N 2,3,6-tribromophenol Chemical compound OC1=C(Br)C=CC(Br)=C1Br VCNCNAPAHSSWCI-UHFFFAOYSA-N 0.000 description 1
- XGCHAIDDPMFRLJ-UHFFFAOYSA-N 2,3,6-trichlorophenol Chemical compound OC1=C(Cl)C=CC(Cl)=C1Cl XGCHAIDDPMFRLJ-UHFFFAOYSA-N 0.000 description 1
- QSFGUSFDWCVXNR-UHFFFAOYSA-N 2,3,6-trifluorophenol Chemical compound OC1=C(F)C=CC(F)=C1F QSFGUSFDWCVXNR-UHFFFAOYSA-N 0.000 description 1
- ADUSGJRADQMJGN-UHFFFAOYSA-N 2,3,6-trihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC(O)=C1O ADUSGJRADQMJGN-UHFFFAOYSA-N 0.000 description 1
- FNAKEOXYWBWIRT-UHFFFAOYSA-N 2,3-dibromophenol Chemical compound OC1=CC=CC(Br)=C1Br FNAKEOXYWBWIRT-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- RPEPGIOVXBBUMJ-UHFFFAOYSA-N 2,3-difluorophenol Chemical compound OC1=CC=CC(F)=C1F RPEPGIOVXBBUMJ-UHFFFAOYSA-N 0.000 description 1
- 229940082044 2,3-dihydroxybenzoic acid Drugs 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
- QQFWMPUXPLBWTG-UHFFFAOYSA-N 2,4,6-trifluorophenol Chemical compound OC1=C(F)C=C(F)C=C1F QQFWMPUXPLBWTG-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- NVWVWEWVLBKPSM-UHFFFAOYSA-N 2,4-difluorophenol Chemical compound OC1=CC=C(F)C=C1F NVWVWEWVLBKPSM-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- GUXWVUVLXIJHQF-UHFFFAOYSA-N 2,5-dibromophenol Chemical compound OC1=CC(Br)=CC=C1Br GUXWVUVLXIJHQF-UHFFFAOYSA-N 0.000 description 1
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 1
- INXKVYFOWNAVMU-UHFFFAOYSA-N 2,5-difluorophenol Chemical compound OC1=CC(F)=CC=C1F INXKVYFOWNAVMU-UHFFFAOYSA-N 0.000 description 1
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 description 1
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 1
- CKKOVFGIBXCEIJ-UHFFFAOYSA-N 2,6-difluorophenol Chemical compound OC1=C(F)C=CC=C1F CKKOVFGIBXCEIJ-UHFFFAOYSA-N 0.000 description 1
- RAEOEMDZDMCHJA-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CCN(CC(O)=O)CC(O)=O)CC(O)=O RAEOEMDZDMCHJA-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KYZSNVXYOQKZAK-UHFFFAOYSA-N 3,4-dibromophenol Chemical compound OC1=CC=C(Br)C(Br)=C1 KYZSNVXYOQKZAK-UHFFFAOYSA-N 0.000 description 1
- BNPWVUJOPCGHIK-UHFFFAOYSA-N 3,4-difluorophenol Chemical compound OC1=CC=C(F)C(F)=C1 BNPWVUJOPCGHIK-UHFFFAOYSA-N 0.000 description 1
- LTPDITOEDOAWRU-UHFFFAOYSA-N 3,4-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1O LTPDITOEDOAWRU-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- HEVGGTGPGPKZHF-UHFFFAOYSA-N Epilaurene Natural products CC1C(=C)CCC1(C)C1=CC=C(C)C=C1 HEVGGTGPGPKZHF-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- CIOAGBVUUVVLOB-NJFSPNSNSA-N Strontium-90 Chemical compound [90Sr] CIOAGBVUUVVLOB-NJFSPNSNSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000001636 atomic emission spectroscopy Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 0.000 description 1
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- GQPLZGRPYWLBPW-UHFFFAOYSA-N calix[4]arene Chemical compound C1C(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC2=CC=CC1=C2 GQPLZGRPYWLBPW-UHFFFAOYSA-N 0.000 description 1
- MMYYTPYDNCIFJU-UHFFFAOYSA-N calix[6]arene Chemical compound C1C(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC2=CC=CC1=C2 MMYYTPYDNCIFJU-UHFFFAOYSA-N 0.000 description 1
- HDPRHRZFFPXZIL-UHFFFAOYSA-N calix[8]arene Chemical compound OC1=C(CC=2C(=C(CC=3C(=C(CC=4C(=C(CC=5C(=C(CC=6C(=C(CC=7C(=C(C8)C=CC=7)O)C=CC=6)O)C=CC=5)O)C=CC=4)O)C=CC=3)O)C=CC=2)O)C=CC=C1CC1=C(O)C8=CC=C1 HDPRHRZFFPXZIL-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- TVFDJXOCXUVLDH-RNFDNDRNSA-N cesium-137 Chemical compound [137Cs] TVFDJXOCXUVLDH-RNFDNDRNSA-N 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960003887 dichlorophen Drugs 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 150000005169 dihydroxybenzoic acids Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000003717 m-cresyl group Chemical group [H]C1=C([H])C(O*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 231100000336 radiotoxic Toxicity 0.000 description 1
- 230000001690 radiotoxic effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000002915 spent fuel radioactive waste Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 229910001427 strontium ion Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
-
- 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
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/19—Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
-
- 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
- C02F1/68—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water
- C02F1/683—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water by addition of complex-forming compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
-
- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21F—PROTECTION AGAINST X-RADIATION, GAMMA RADIATION, CORPUSCULAR RADIATION OR PARTICLE BOMBARDMENT; TREATING RADIOACTIVELY CONTAMINATED MATERIAL; DECONTAMINATION ARRANGEMENTS THEREFOR
- G21F9/00—Treating radioactively contaminated material; Decontamination arrangements therefor
- G21F9/04—Treating liquids
- G21F9/06—Processing
- G21F9/12—Processing by absorption; by adsorption; by ion-exchange
-
- 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
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
- C02F2001/425—Treatment of water, waste water, or sewage by ion-exchange using cation exchangers
-
- 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
- C02F2101/006—Radioactive compounds
Definitions
- the invention relates to the field of radionuclide decontamination of aqueous media in which these radionuclides are present in small amounts.
- the invention relates to an ion exchange resin, of the formo-phenolic type, which has chelating properties, which has a selectivity to both cesium and strontium and which is therefore as such, particularly adapted to coextract (that is to say, extract in a grouped manner) these two elements of an aqueous medium in which they are located, this aqueous medium can be a freshwater medium or a seawater environment.
- the invention also relates to a process for preparing this resin as well as to uses of said resin.
- the invention is likely to find applications in all situations where it may be desirable to decontaminate an aqueous medium of cesium and / or strontium and, in particular, in the nuclear industry to treat aqueous liquid effluents which affect the environment.
- one and / or the other of these two elements which are likely to be produced by nuclear facilities, either as part of their normal operation (for example, in the context of an activity of reprocessing spent nuclear fuel) either accidentally.
- Irradiated nuclear fuel reprocessing plants produce so-called low and intermediate-level aqueous liquid effluents (FA-MA), which contain a number of radionuclides resulting from nuclear fission and corrosion of fuel cladding. , and therefore need to be treated for extract these radionuclides.
- FA-MA low and intermediate-level aqueous liquid effluents
- To the effluents resulting from the reprocessing of the irradiated nuclear fuels are added the effluents of washing of the contaminated equipment as well as the effluents related to possible nuclear incidents.
- Cesium 137 and strontium 90 are among the radionuclides whose extraction is more specifically targeted because they are abundant in irradiated nuclear fuels (and of which in the aqueous liquid effluents resulting from the reprocessing of these fuels) and their period of approximately 30 years makes them particularly radiotoxic. Moreover, this period is too long for the decay to take place within a reasonable time interval.
- the decontamination of aqueous effluents FA-MA is generally carried out by means of purification systems based on the use of ion exchange resins (sulfonic, carboxylic, formo-phenolic, ...) or by processes of coprecipitation.
- ion exchange resins sulfonic, carboxylic, formo-phenolic, ...)
- processes of coprecipitation have limitations, namely that co-precipitation generates large volumes of waste in the form of sludge and thus leads to large volumes of storage, while the ion exchange resins currently used have a low ability to extract metal ions in a grouped manner.
- the possibility of extracting radionuclides in a grouped manner from aqueous liquid effluents is a key point for treating these effluents while producing a minimum of waste.
- formo-phenolic polymer resins which are also known as phenol-formaldehyde resins and which are obtained by the polycondensation of phenolic compounds and formaldehyde, typically in a basic medium, can be used to extract cesium and strontium from an aqueous saline medium.
- K.A. K. Ebraheem et al. (Sep. Sci.Technol., 35 (13), 2115-2125 (2000), reference [4]) incorporated 8-hydroxyquinoline in bisphenol A and formaldehyde resins, and studied the behavior of resins thus obtained with respect to lanthanum, cerium, neodymium, samarium and gadolinium;
- the DTPA is present in the polymer matrix forming the resin without being immobilized on this matrix, which, taking into account the solubility of this compound in the aqueous phase, may lead to its release by the resin during the use of the latter in an aqueous medium and, therefore, to an alteration, even a loss, of its chelating properties.
- the purpose of the inventors is to provide new ion exchange resins with chelating properties that are selective both for cesium and strontium and In this way, these two elements of an aqueous medium can be grouped together and their chelating properties are not likely to be altered during use.
- the goal of the inventors is also that the synthesis of these resins is simple to implement and can be achieved at costs compatible with their use on an industrial scale.
- At least one first phenolic monomer, chelating which corresponds to the following general formula (I):
- n 0, 1 or 2
- R2, R3, R 4, R 5 represent independently each other a hydrogen atom, -OH, an alkyl group in Ci to Ci 0, alkoxy, Ci to Ci 0 aryl, an aryloxy group, a -SO 3 H group, a -COOR group in which R represents a hydrogen atom or a C 1 -C 10 alkyl group, a -P (O) (OR) (OR ') group or a -C (O) NRR 'group in which R and R' are, independently of each other, a hydrogen atom or a C 1 -C 10 alkyl group; with the proviso that at least one of R 1 to R 5 is -OH and at least two of R 1 to R 5 are hydrogen;
- the resin according to the invention is a formophenolic type resin which is functionalized with chelating groups derived from ethylene diamine tetraacetic acid (EDTA), diethylene triamine pentaacetic acid (DTPA) or acid. triethylene tetramine hexaacetic acid (HTTA) but in which the chelating groups are an integral part of the polymer matrix of the resin since the latter is obtained by condensation of a first phenolic monomer carrying these chelating groups, a second phenolic monomer and formaldehyde .
- EDTA ethylene diamine tetraacetic acid
- DTPA diethylene triamine pentaacetic acid
- HTTA triethylene tetramine hexaacetic acid
- this resin has been shown to have a selectivity, not only towards cesium but also towards strontium, as will be demonstrated in Example 3 below.
- C 1 -C 10 alkyl group means any alkyl group, linear or branched, which is formed by at least one carbon atom and at most ten carbon atoms such as a methyl, ethyl or propyl group such as ⁇ -propyl or isopropyl, butyl such as ⁇ -butyl, sec-butyl, isobutyl or ieri-butyl, pentyl as ⁇ -pentyl, sec-pentyl or isopentyl, hexyl as ⁇ -hexyl or isohexyl, heptyl as ⁇ -heptyl or isoheptyl, octyl as ⁇ -octyl or isooctyl, nonyl as n-nonyl or isononyl, decyl as ⁇ -decyl or isodecyl, etc. ;
- C 1 -C 10 alkoxy group means any linear or branched O-alkyl group which is formed by at least one carbon atom and at most ten carbon atoms such as a methoxy, ethoxy or propoxy group; , isopropoxy, butoxy such as ⁇ -butoxy, sec-butoxy or isobutoxy, pentoxy as ⁇ -pentoxy, sec-pentoxy or iso-pentoxy, hexoxy as ⁇ -hexoxy or isohexoxy, heptoxy as ⁇ -heptoxy or isoheptoxy, octoxy as ⁇ -octoxy or isooctoxy, nonoxy such as ⁇ -nonoxy or isononoxy, decoxy as ⁇ -decoxy or isodecoxy, etc .;
- Aryl group means any group derived from an arene, that is to say from a hydrocarbon whose formula is derived from benzene, such as a phenyl, benzyl, naphthyl, o-tolyl or m-tolyl group; p-tolyl, o-xylyl, m-xylyl, p-xylyl, phenethyl, etc .; and by
- Aryloxy group means any O-aryl group in which the aryl group is as defined above such as, for example, phenoxy, benzyloxy, naphthyloxy, o-tolyloxy, m-tolyloxy, p-tolyloxy, o- xylyloxy, m-xylyloxy, p-xylyloxy, phenethyloxy, etc.
- alkyl and alkoxy groups which comprise from 1 to 6 carbon atoms, aryl groups which are chosen from phenyl, benzyl and phenethyl groups, the phenyl group being especially preferred - and aryloxy groups which are selected from phenoxy, benzyloxy and phenethyloxy, phenyloxy being most preferred.
- the first phenolic monomer preferably corresponds to the general formula (I) above in which R 3 represents a -OH group, Ri and R 5 both represent a hydrogen atom, while m, n, R 2 and R 4 have the same meaning as above.
- the first phenolic monomer corresponds to the general formula (I) above wherein m is 2, R 3 is -OH, R 1, R 2 and R 5 all represent a hydrogen atom, R 4 represents a hydrogen atom or a -OH group, while n has the same meaning as above.
- Phenolic monomers which correspond to the above general formula (I) in which m is 2, R 3 represents a group -OH, R 1, R 2 , R 4 and R 5 all represent a hydrogen atom, while n is 0 or 1, are most preferred.
- the second phenolic monomer can be any phenolic compound which is capable of conducting, by condensation with formaldehyde, a formophenolic resin provided that this compound does not meet the general formula (I) below. before.
- it can be any compound which comprises at least one benzene ring at least one carbon atom of which bears an -OH group and at least two carbon atoms of which carry a hydrogen atom but which do not meets the general formula (I) above.
- the second phenolic monomer preferably comprises 1 to 4 benzene rings, which can either be connected two by two through a vertex or via an atom, for example oxygen, or a group, by -CH 2 - or -C (CH 3 ) 2 -, forming a bridge, or be contiguous to each other, each of these benzene rings having at least one carbon atom carrying a -OH group and at least two carbon atoms carrying a hydrogen atom.
- the second phenolic monomer can be chosen from phenol, catechol (or 1,2-dihydroxybenzene), resorcinol (or 1,3-dihydroxybenzene), hydroquinone (or 1,4-dihydroxybenzene), hydroxyquinol (or 1,2,4-trihydroxybenzene), phloroglucinol (or 1,3,5-trihydroxybenzene), pyrogallol (or 1,2,3-trihydroxybenzene), benzenetetrol (or 1,2,3,5-tetrahydroxybenzene), cresols (m-, o- and p-cresol), xylenols (2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2 , 6-xylenol, 3,4-xylenol and 3,5-xylenol), hydroxybenzoic acids (2-hydroxybenzoic acid, 3-hydroxybenzoic acid and 4-hydroxy
- the second phenolic monomer is preferably chosen from dihydroxybenzenes (cathecol, resorcinol and hydroquinone) and calix [4] resorcinarene, resorcinol being very particularly preferred.
- the resin according to the invention may in particular be obtained by a process which comprises:
- reaction medium comprising the first and second phenolic monomers, formaldehyde and a strong base
- step a) the application of a heat treatment to the reaction medium thus prepared to obtain the formation of the resin by polycondensation of the first and second phenol monomers and formaldehyde.
- step a) may in particular be carried out by:
- step a) use is preferably made of:
- a molar ratio between the first phenolic monomer and the second phenolic monomer which is between 0.1 and 5 and, more preferably, between 0.5 and 2;
- a molar ratio between formaldehyde and the first and second phenolic monomers which is between 2 and 10 and, more preferably, between 2 and 4;
- a molar ratio between the strong base and the first and second phenolic monomers which is between 0.5 and 2.5 and more preferably between 1 and 2;
- a molar ratio between the water (which is present in the aqueous solution of strong base) and the first and second phenolic monomers which is between 25 and 500 and, more preferably, between 50 and 150.
- the strong base is preferably a metal hydroxide such as an alkali metal hydroxide of the lithium hydroxide type, sodium hydroxide, potassium hydroxide or cesium hydroxide, or an alkaline earth metal hydroxide of calcium hydroxide type, strontium hydroxide or barium hydroxide.
- a metal hydroxide such as an alkali metal hydroxide of the lithium hydroxide type, sodium hydroxide, potassium hydroxide or cesium hydroxide, or an alkaline earth metal hydroxide of calcium hydroxide type, strontium hydroxide or barium hydroxide.
- Sodium hydroxide is most preferred.
- the heat treatment preferably consists in heating the reaction medium to a temperature of between 95 ° C. and 130 ° C. and, more preferably, between 95 ° C. and 110 ° C., for 16 hours at 96 hours and, better still, 48 to 96 hours.
- the process may advantageously furthermore comprise the reduction of the resin obtained in stage b) in the form of particles, for example by grinding, these particles preferably measuring from 0.05 to 1 mm, the washing the particles thus obtained with aqueous solutions, for example alternately acidic and basic, and drying the particles thus washed, for example in an oven.
- aqueous solutions for example alternately acidic and basic
- An ion exchange resin is thus obtained, which has chelating properties and is ready to be used for extracting cesium or strontium from an aqueous medium containing one of these elements, or even more to extract these two elements grouped together if they are both present in the same aqueous medium.
- the subject of the invention is also the use of an ion exchange resin with chelating properties, as defined above, for extracting cesium and / or strontium from an aqueous medium in which one and / or the other of these elements are present.
- the resin is used to co-extract cesium and strontium from an aqueous medium in which these two elements are present.
- the aqueous medium is preferably an industrial aqueous liquid effluent and, in particular, an aqueous liquid effluent from the nuclear industry such as, for example, a low and medium activity effluent resulting from the reprocessing of irradiated nuclear fuel, or any other aqueous liquid effluent containing radio-contaminants.
- the extraction of cesium and / or strontium from an aqueous medium, whether it be a freshwater or seawater medium, using a resin according to the invention is extremely simple to implement since it is sufficient to put this resin in contact with the aqueous medium, for example in a stirred reactor or in a column, for a time sufficient to allow cesium and / or strontium to be complexed by the resin, and then separate the resin from the aqueous medium.
- the first phenolic monomer of general formula (I) can be obtained by reaction of a compound of general formula (II) below: in which n is 0, 1 or 2, with a compound of general formula (III) below:
- R lr R 2, R 3, R 4, R 5 represent independently each other a hydrogen atom, -OH, an alkyl group in Ci to Ci 0, a alkoxy Ci-Ci 0, an aryl group, an aryloxy group, an -S0 3 H group, a -COOR group wherein R represents a hydrogen atom or an alkyl group C1 to 0, a group -P (O) (OR) (OR ') or a group -C (O) NRR' in which R and R 'independently of one another represent a hydrogen atom or a C 1 -C 10 alkyl group ; with the proviso that at least one of R 1 to R 5 is -OH and at least two of R 1 to R 5 are hydrogen; using procedures adapted from those described in the literature (Lauren et al., Eur J.
- FIG. 1 represents, in graphic form, the values of the distribution coefficient (K D in ml / g) and of the extraction percentage (E) obtained for strontium during tests consisting in extracting cesium and strontium from a aqueous solution simulating a seawater diluted to 200 ppm sodium and doped with cesium and strontium, at a concentration of 10 -4 M, with two resins according to the invention (ETRF-Na and DTRF-Na) and by varying the amount of resin used from 0.5 g to 25 g / l of aqueous solution.
- K D in ml / g the distribution coefficient
- E extraction percentage
- FIG. 2 represents, in graphical form, the values of the distribution coefficient (K D in ml / g) and of the extraction percentage (E) obtained for cesium in tests consisting in extracting cesium and strontium from a aqueous solution simulating a seawater diluted to 200 ppm sodium and doped with cesium and strontium, at a concentration of 10 -4 M, with two resins according to the invention (ETRF-Na and DTRF-Na) and by varying the quantity of resin used from 0.5 g to 25 g / l of aqueous solution DETAILED DESCRIPTION OF PARTICULAR EMBODIMENTS
- n 1 for DTPA-bis-dopamide.
- R 4 represents a hydrogen atom or an -OH group, while n is 0 or ln is 0 or 1
- the products are dissolved in ethanol (32 ml for the two products resulting from the condensation with dopamine and 65 ml for the two products resulting from the condensation with tyramine), then precipitated in diethyl ether (150 mL). The precipitates are filtered and then washed with diethyl ether before drying in vacuo.
- the returns are in all cases of the order of 80%.
- Resins according to the invention are synthesized using:
- NaOH sodium hydroxide
- CsOH cesium hydroxide
- a chelating monomer / phenol monomer / formaldehyde / strong base / H 2 0 molar ratio of 0.5 / 0.5 / 2.5 / 1.5 / 100.
- the chelating monomer (0.5 mmol) and the phenolic monomer (0.5 mmol) are first solubilized in a solution of NaOH or CsOH (1.5 mmol in 100 mmol H 2 0). The resulting solution is stirred at room temperature or at 0 ° C and formaldehyde (2.5 mmol) is added to this solution. The reaction mixture is stirred for 24 hours after which it is heated in an oven under air at 100 ° C for 96 hours.
- solution 1 ultrapure water (milli-Q TM water) doped with cesium and strontium (in the form of CsCl and SrCl 2 chlorides) at a concentration of 10 -4 M;
- solution 2 a solution simulating a seawater diluted at 200 ppm (parts per million) of sodium and doped with cesium and strontium (in the form of CsCl and SrCl 2 chlorides) at a concentration of 10 -4 M;
- solution 3 a solution simulating a seawater diluted with 200 ppm of sodium and 25 ppm of calcium, doped with cesium and strontium (in the form of chlorides CsCl and SrCl 2 ) at a concentration of 10 -4 M.
- K D the coefficient of distribution
- ml / g the coefficient of distribution
- Ci initial concentration of the cation in solution (in mg / L);
- V volume of solution (in mL);
- Ci initial concentration of the cation in solution (in mg / L);
- Tables II and III below show the K D , E and FD values obtained for cesium and strontium respectively, with the twenty-two resins synthesized in Example 2 and solutions 1 and 2, and using 1 g of resin per L of solution.
- Table IV shows the K D and E values obtained for strontium, with the ETRF-Na and DTRF-Na resins synthesized in Example 2 above and solutions 2 and 3, by varying the amount of resin used per L solution of 0.5 g to 25 g. Table IV
- FIG. 1 represents, in graphic form, the results presented in Table IV above for solution 2, while FIG. 2 represents, also in graphical form, the K D and E values obtained for cesium, with the ETRF-Na and DTRF-Na resins synthesized in Example 2 above and the solution 2, made it vary the amount of resin used per L of solution (from 0.5 g to 25 g)
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Abstract
Description
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FR1261620A FR2998816B1 (fr) | 2012-12-04 | 2012-12-04 | Resine echangeuse d'ions a proprietes chelatantes, son procede de preparation et ses utilisations |
PCT/EP2013/075406 WO2014086788A1 (fr) | 2012-12-04 | 2013-12-03 | Résine échangeuse d'ions à propriétés chélatantes, son procédé de préparation et ses utilisations |
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WO2009150983A1 (fr) * | 2008-06-12 | 2009-12-17 | 日立化成工業株式会社 | Procédé de fabrication de résine novolac phénolique et sable enduit à la résine |
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