CN102449101A - 溴化锂/水吸收循环系统中的离子化合物 - Google Patents
溴化锂/水吸收循环系统中的离子化合物 Download PDFInfo
- Publication number
- CN102449101A CN102449101A CN2010800241084A CN201080024108A CN102449101A CN 102449101 A CN102449101 A CN 102449101A CN 2010800241084 A CN2010800241084 A CN 2010800241084A CN 201080024108 A CN201080024108 A CN 201080024108A CN 102449101 A CN102449101 A CN 102449101A
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- Prior art keywords
- acid
- methylimidazole
- substituted
- compsn
- independently
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 title claims abstract description 170
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 110
- 238000010521 absorption reaction Methods 0.000 title claims abstract description 99
- 150000008040 ionic compounds Chemical class 0.000 title claims abstract description 65
- 239000000203 mixture Substances 0.000 claims abstract description 92
- 239000012530 fluid Substances 0.000 claims abstract description 34
- 239000003507 refrigerant Substances 0.000 claims description 109
- 229910052757 nitrogen Inorganic materials 0.000 claims description 85
- 150000002500 ions Chemical class 0.000 claims description 83
- 239000002253 acid Substances 0.000 claims description 73
- -1 alkali metal salt Chemical class 0.000 claims description 73
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 55
- 150000001336 alkenes Chemical class 0.000 claims description 51
- 229910052760 oxygen Inorganic materials 0.000 claims description 51
- 229910052710 silicon Inorganic materials 0.000 claims description 51
- 229910052717 sulfur Inorganic materials 0.000 claims description 51
- 150000001924 cycloalkanes Chemical class 0.000 claims description 49
- 229940040102 levulinic acid Drugs 0.000 claims description 41
- 239000000460 chlorine Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 34
- 229940059936 lithium bromide Drugs 0.000 claims description 33
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 30
- 229910052794 bromium Inorganic materials 0.000 claims description 29
- 238000001816 cooling Methods 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 229910052740 iodine Inorganic materials 0.000 claims description 27
- 239000006200 vaporizer Substances 0.000 claims description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 18
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 claims description 14
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 13
- 229960001231 choline Drugs 0.000 claims description 13
- 125000000129 anionic group Chemical group 0.000 claims description 12
- KZWJWYFPLXRYIL-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)F KZWJWYFPLXRYIL-UHFFFAOYSA-N 0.000 claims description 11
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 claims description 10
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 claims description 10
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- JJJOZVFVARQUJV-UHFFFAOYSA-N 2-ethylhexylphosphonic acid Chemical compound CCCCC(CC)CP(O)(O)=O JJJOZVFVARQUJV-UHFFFAOYSA-N 0.000 claims description 8
- ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 claims description 8
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 150000003973 alkyl amines Chemical class 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Substances OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- GKCVFQNAFQNNQE-UHFFFAOYSA-N C(CCC)N1CN(C=C1)C.C(CC)(=O)O Chemical compound C(CCC)N1CN(C=C1)C.C(CC)(=O)O GKCVFQNAFQNNQE-UHFFFAOYSA-N 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims description 6
- MDSBAFLOQJDAHX-UHFFFAOYSA-N 3-butyl-1-methyl-1,2-dihydroimidazol-1-ium;ethanesulfonate Chemical compound CCS([O-])(=O)=O.CCCCN1C[NH+](C)C=C1 MDSBAFLOQJDAHX-UHFFFAOYSA-N 0.000 claims description 5
- 229910016467 AlCl 4 Inorganic materials 0.000 claims description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 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 claims description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 claims description 5
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- 239000004153 Potassium bromate Substances 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims description 4
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims description 4
- 150000003983 crown ethers Chemical class 0.000 claims description 4
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 claims description 4
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 claims description 4
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims description 4
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 claims description 4
- 229940102859 methylene diphosphonate Drugs 0.000 claims description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000007965 phenolic acids Chemical class 0.000 claims description 4
- 150000003016 phosphoric acids Chemical class 0.000 claims description 4
- 229940094037 potassium bromate Drugs 0.000 claims description 4
- 235000019396 potassium bromate Nutrition 0.000 claims description 4
- 239000000276 potassium ferrocyanide Substances 0.000 claims description 4
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 claims description 4
- 239000001230 potassium iodate Substances 0.000 claims description 4
- 229940093930 potassium iodate Drugs 0.000 claims description 4
- 235000006666 potassium iodate Nutrition 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229960003351 prussian blue Drugs 0.000 claims description 4
- 239000013225 prussian blue Substances 0.000 claims description 4
- 229940023144 sodium glycolate Drugs 0.000 claims description 4
- XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 claims description 4
- FURUVJOXOXSHDX-UHFFFAOYSA-M 2,2-dichloroacetate;tetramethylazanium Chemical compound C[N+](C)(C)C.[O-]C(=O)C(Cl)Cl FURUVJOXOXSHDX-UHFFFAOYSA-M 0.000 claims description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- JSGREAVPDCFWAB-UHFFFAOYSA-M 2-oxopropanoate;tetramethylazanium Chemical compound C[N+](C)(C)C.CC(=O)C([O-])=O JSGREAVPDCFWAB-UHFFFAOYSA-M 0.000 claims description 3
- 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 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- FWYSSOIRLVHQNC-UHFFFAOYSA-M benzyl(trimethyl)azanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)CC1=CC=CC=C1 FWYSSOIRLVHQNC-UHFFFAOYSA-M 0.000 claims description 3
- 229910052792 caesium Inorganic materials 0.000 claims description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- WWIYWFVQZQOECA-UHFFFAOYSA-M tetramethylazanium;formate Chemical compound [O-]C=O.C[N+](C)(C)C WWIYWFVQZQOECA-UHFFFAOYSA-M 0.000 claims description 3
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 24
- 230000000996 additive effect Effects 0.000 abstract description 22
- 238000002425 crystallisation Methods 0.000 abstract description 14
- 230000008025 crystallization Effects 0.000 abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- 239000003795 chemical substances by application Substances 0.000 description 108
- 239000000243 solution Substances 0.000 description 106
- 239000007788 liquid Substances 0.000 description 74
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 73
- 238000005057 refrigeration Methods 0.000 description 60
- 239000000047 product Substances 0.000 description 52
- 238000003756 stirring Methods 0.000 description 46
- 238000002360 preparation method Methods 0.000 description 42
- 239000007787 solid Substances 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 239000002608 ionic liquid Substances 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000005406 washing Methods 0.000 description 18
- 230000003311 flocculating effect Effects 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 16
- 229910021641 deionized water Inorganic materials 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 238000003760 magnetic stirring Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 229910052500 inorganic mineral Inorganic materials 0.000 description 13
- 239000011707 mineral Substances 0.000 description 13
- 235000010755 mineral Nutrition 0.000 description 13
- 239000002002 slurry Substances 0.000 description 12
- 238000000967 suction filtration Methods 0.000 description 12
- 238000013019 agitation Methods 0.000 description 11
- 230000006837 decompression Effects 0.000 description 11
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 229910052744 lithium Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- 239000013529 heat transfer fluid Substances 0.000 description 9
- 238000010926 purge Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000005660 chlorination reaction Methods 0.000 description 8
- 230000008021 deposition Effects 0.000 description 8
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 238000004378 air conditioning Methods 0.000 description 7
- 229940075419 choline hydroxide Drugs 0.000 description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 7
- 239000002826 coolant Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 7
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 6
- 239000013068 control sample Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
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- 238000005303 weighing Methods 0.000 description 6
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000033228 biological regulation Effects 0.000 description 5
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- 239000010410 layer Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- IKGXNKJBJMBJRA-UHFFFAOYSA-N potassium;1,1,2,2-tetrafluoroethanesulfonic acid Chemical compound [K].OS(=O)(=O)C(F)(F)C(F)F IKGXNKJBJMBJRA-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000004062 sedimentation Methods 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- DVYSHWKJRYAQOJ-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCCCN1CN(C)C=C1 DVYSHWKJRYAQOJ-UHFFFAOYSA-N 0.000 description 4
- ZXLOSLWIGFGPIU-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;acetate Chemical compound CC(O)=O.CCN1CN(C)C=C1 ZXLOSLWIGFGPIU-UHFFFAOYSA-N 0.000 description 4
- SFPTVQNKTCPLAX-UHFFFAOYSA-N 3-ethyl-1-methyl-1,2-dihydroimidazol-1-ium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC[NH+]1CN(C)C=C1 SFPTVQNKTCPLAX-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 0 CC1N(*)NC(*)C(*)C1* Chemical compound CC1N(*)NC(*)C(*)C1* 0.000 description 4
- 229910000990 Ni alloy Inorganic materials 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000004645 aluminates Chemical class 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/047—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for absorption-type refrigeration systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
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- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
- F25B15/00—Sorption machines, plants or systems, operating continuously, e.g. absorption type
- F25B15/02—Sorption machines, plants or systems, operating continuously, e.g. absorption type without inert gas
- F25B15/06—Sorption machines, plants or systems, operating continuously, e.g. absorption type without inert gas the refrigerant being water vapour evaporated from a salt solution, e.g. lithium bromide
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
- F25B2315/00—Sorption refrigeration cycles or details thereof
- F25B2315/001—Crystallization prevention
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A30/00—Adapting or protecting infrastructure or their operation
- Y02A30/27—Relating to heating, ventilation or air conditioning [HVAC] technologies
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
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- Y02B30/62—Absorption based systems
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Sorption Type Refrigeration Machines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
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| US16516609P | 2009-03-31 | 2009-03-31 | |
| US16517309P | 2009-03-31 | 2009-03-31 | |
| US16516009P | 2009-03-31 | 2009-03-31 | |
| US61/165173 | 2009-03-31 | ||
| US61/165166 | 2009-03-31 | ||
| US61/165160 | 2009-03-31 | ||
| PCT/US2010/029322 WO2010117836A1 (en) | 2009-03-31 | 2010-03-31 | Ionic compounds in lithium bromide/water absorption cycle systems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102449101A true CN102449101A (zh) | 2012-05-09 |
Family
ID=42236734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN2010800241084A Pending CN102449101A (zh) | 2009-03-31 | 2010-03-31 | 溴化锂/水吸收循环系统中的离子化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20120011886A1 (enExample) |
| EP (1) | EP2414476A1 (enExample) |
| JP (1) | JP2012522873A (enExample) |
| KR (1) | KR20120003471A (enExample) |
| CN (1) | CN102449101A (enExample) |
| AU (1) | AU2010234813A1 (enExample) |
| BR (1) | BRPI1006734A2 (enExample) |
| CA (1) | CA2754599A1 (enExample) |
| WO (1) | WO2010117836A1 (enExample) |
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| CN108190916A (zh) * | 2017-12-29 | 2018-06-22 | 新奥泛能网络科技股份有限公司 | 合成氨分离的方法和系统 |
| CN109477671A (zh) * | 2016-04-06 | 2019-03-15 | 华氏有限公司 | 吸附式热泵和用于运行吸附式热泵的方法 |
| CN110530055A (zh) * | 2018-05-25 | 2019-12-03 | 株式会社日立电力解决方案 | 吸收式冷热水机、吸收式冷热水机用追加液、吸收式冷热水机用吸收液及维护方法 |
| CN113025282A (zh) * | 2021-03-26 | 2021-06-25 | 苏州佳永新能源科技有限公司 | 一种化学吸收循环用复配吸附介质 |
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| EP2088389B1 (de) * | 2008-02-05 | 2017-05-10 | Evonik Degussa GmbH | Absorptionskältemaschine |
| WO2010054230A2 (en) * | 2008-11-07 | 2010-05-14 | E. I. Du Pont De Nemours And Company | Absorption cycle utilizing ionic compounds and/or non-ionic absorbents as working fluids |
| DE102009047564A1 (de) * | 2009-12-07 | 2011-06-09 | Evonik Degussa Gmbh | Arbeitsmedium für eine Absorptionskältemaschine |
| CA2817264C (en) * | 2010-11-08 | 2016-12-13 | Evonik Degussa Gmbh | Working medium for absorption heat pumps |
| DE102011077377A1 (de) | 2010-11-12 | 2012-05-16 | Evonik Degussa Gmbh | Verfahren zur Absorption von sauren Gasen aus Gasmischungen |
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| WO2013072147A1 (de) | 2011-11-14 | 2013-05-23 | Evonik Degussa Gmbh | Verfahren und vorrichtung zur abtrennung von sauren gasen aus einer gasmischung |
| DE102012200907A1 (de) | 2012-01-23 | 2013-07-25 | Evonik Industries Ag | Verfahren und Absorptionsmedium zur Absorption von CO2 aus einer Gasmischung |
| DE102012207509A1 (de) | 2012-05-07 | 2013-11-07 | Evonik Degussa Gmbh | Verfahren zur Absorption von CO2 aus einer Gasmischung |
| WO2014172042A1 (en) * | 2013-03-15 | 2014-10-23 | Sandia Corporation | Synthesis of novel ionic liquids from lignin-derived compounds |
| US8720216B1 (en) | 2013-10-01 | 2014-05-13 | King Fahd University Of Petroleum And Minerals | Hybrid aqua-ammonia and lithium bromide-water absorption chiller |
| US20160231032A1 (en) * | 2015-02-07 | 2016-08-11 | Morteza Ghassemi | Piezo Electric and High Voltage Absorption Cooling System |
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| DE102015212749A1 (de) | 2015-07-08 | 2017-01-12 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
| GB201513304D0 (en) * | 2015-07-28 | 2015-09-09 | Innospec Ltd | Compositions and Methods |
| WO2017058747A1 (en) | 2015-09-28 | 2017-04-06 | University Of Florida Research Foundation, Inc. | Ionic liquid-based absorption cooling system with high coefficient of performance |
| WO2017205807A1 (en) * | 2016-05-26 | 2017-11-30 | Yazaki Corporation | Eutectic mixtures of ionic liquids in absorption chillers |
| JP2019517654A (ja) * | 2016-05-26 | 2019-06-24 | 矢崎総業株式会社 | 吸収式冷凍機におけるグアニジニウム系イオン液体 |
| WO2017214334A1 (en) | 2016-06-07 | 2017-12-14 | National Technology & Engineering Solutions Of Sandia, Llc | Conversion of lignin to ionic liquids |
| DE102016210478A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
| DE102016210483A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren und Absorptionsmittel zur Entfeuchtung von feuchten Gasgemischen |
| DE102016210484A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
| EP3257568B1 (de) | 2016-06-14 | 2019-09-18 | Evonik Degussa GmbH | Verfahren zur entfeuchtung von feuchten gasgemischen mit ionischen flüssigkeiten |
| EP3257843A1 (en) | 2016-06-14 | 2017-12-20 | Evonik Degussa GmbH | Method of preparing a high purity imidazolium salt |
| DE102016210481B3 (de) | 2016-06-14 | 2017-06-08 | Evonik Degussa Gmbh | Verfahren zum Reinigen einer ionischen Flüssigkeit |
| US10584904B2 (en) * | 2017-03-27 | 2020-03-10 | Rebound Technologies, Inc. | Cycle enhancement methods, systems, and devices |
| WO2018186859A1 (en) | 2017-04-05 | 2018-10-11 | General Electric Company | Absorption cycle apparatus and related method |
| US11028249B2 (en) * | 2017-08-31 | 2021-06-08 | National Technology & Engineering Solutions Of Sandia, Llc | Methods of synthesizing ionic liquids from primary alcohol-containing lignin compounds |
| ES3020410T3 (en) | 2018-02-23 | 2025-05-22 | Rebound Tech Inc | Freeze point suppression cycle control systems, methods, and devices |
| JP2020015688A (ja) * | 2018-07-25 | 2020-01-30 | 国立大学法人千葉大学 | 硫黄を含むホスホニウム型カチオン及び硫黄を含むホスホニウム型イオン液体 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| WO2020132467A1 (en) | 2018-12-20 | 2020-06-25 | Rebound Technologies, Inc. | Thermo-chemical recuperation systems, devices, and methods |
| EP3810578B1 (en) * | 2019-01-15 | 2023-01-04 | Yazaki Corporation | Ionic liquid additives for use as an absorbent in absorption chillers |
| GB2600445A (en) * | 2020-10-29 | 2022-05-04 | Burton Geoff | Phase change material |
| CN112944719A (zh) * | 2021-03-24 | 2021-06-11 | 苏州佳永新能源科技有限公司 | 一种化学吸收制冷循环用复配工质对和应用方法 |
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- 2010-03-31 CN CN2010800241084A patent/CN102449101A/zh active Pending
- 2010-03-31 JP JP2012503643A patent/JP2012522873A/ja not_active Abandoned
- 2010-03-31 AU AU2010234813A patent/AU2010234813A1/en not_active Abandoned
- 2010-03-31 KR KR1020117025482A patent/KR20120003471A/ko not_active Withdrawn
- 2010-03-31 WO PCT/US2010/029322 patent/WO2010117836A1/en not_active Ceased
- 2010-03-31 BR BRPI1006734A patent/BRPI1006734A2/pt not_active IP Right Cessation
- 2010-03-31 EP EP10712637A patent/EP2414476A1/en not_active Withdrawn
- 2010-03-31 US US13/259,229 patent/US20120011886A1/en not_active Abandoned
- 2010-03-31 CA CA2754599A patent/CA2754599A1/en not_active Abandoned
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109477671A (zh) * | 2016-04-06 | 2019-03-15 | 华氏有限公司 | 吸附式热泵和用于运行吸附式热泵的方法 |
| CN109477671B (zh) * | 2016-04-06 | 2021-04-27 | 华氏有限公司 | 吸附式热泵和用于运行吸附式热泵的方法 |
| CN108190916A (zh) * | 2017-12-29 | 2018-06-22 | 新奥泛能网络科技股份有限公司 | 合成氨分离的方法和系统 |
| CN108190916B (zh) * | 2017-12-29 | 2020-09-18 | 新奥泛能网络科技股份有限公司 | 合成氨分离的方法和系统 |
| CN110530055A (zh) * | 2018-05-25 | 2019-12-03 | 株式会社日立电力解决方案 | 吸收式冷热水机、吸收式冷热水机用追加液、吸收式冷热水机用吸收液及维护方法 |
| CN113025282A (zh) * | 2021-03-26 | 2021-06-25 | 苏州佳永新能源科技有限公司 | 一种化学吸收循环用复配吸附介质 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2754599A1 (en) | 2010-10-14 |
| EP2414476A1 (en) | 2012-02-08 |
| KR20120003471A (ko) | 2012-01-10 |
| BRPI1006734A2 (pt) | 2019-04-02 |
| JP2012522873A (ja) | 2012-09-27 |
| AU2010234813A1 (en) | 2011-09-22 |
| AU2010234813A2 (en) | 2011-09-22 |
| WO2010117836A1 (en) | 2010-10-14 |
| US20120011886A1 (en) | 2012-01-19 |
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