GB1074233A - Cuprous chloride or bromide complexing agents - Google Patents
Cuprous chloride or bromide complexing agentsInfo
- Publication number
- GB1074233A GB1074233A GB2556764A GB2556764A GB1074233A GB 1074233 A GB1074233 A GB 1074233A GB 2556764 A GB2556764 A GB 2556764A GB 2556764 A GB2556764 A GB 2556764A GB 1074233 A GB1074233 A GB 1074233A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cuprous
- particles
- cuprous halide
- acetylene
- bromide
- 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.)
- Expired
Links
- 239000008139 complexing agent Substances 0.000 title abstract 15
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 title abstract 7
- 229910021589 Copper(I) bromide Inorganic materials 0.000 title abstract 7
- 229910021591 Copper(I) chloride Inorganic materials 0.000 title abstract 6
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 title abstract 6
- 229940045803 cuprous chloride Drugs 0.000 title abstract 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 16
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 16
- 239000002245 particle Substances 0.000 abstract 16
- 150000004820 halides Chemical class 0.000 abstract 14
- -1 ethylene, propylene, butylene, isobutylene Chemical group 0.000 abstract 10
- 238000001556 precipitation Methods 0.000 abstract 8
- 239000002904 solvent Substances 0.000 abstract 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 125000001931 aliphatic group Chemical group 0.000 abstract 6
- 239000012296 anti-solvent Substances 0.000 abstract 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 6
- 239000007788 liquid Substances 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 4
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical group CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 abstract 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 abstract 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 230000003213 activating effect Effects 0.000 abstract 4
- 150000001298 alcohols Chemical class 0.000 abstract 4
- 150000001361 allenes Chemical class 0.000 abstract 4
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 abstract 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000005677 ethinylene group Chemical class [*:2]C#C[*:1] 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- 150000002334 glycols Chemical class 0.000 abstract 4
- 150000002576 ketones Chemical class 0.000 abstract 4
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 abstract 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 abstract 4
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 abstract 4
- 238000000926 separation method Methods 0.000 abstract 4
- 125000002723 alicyclic group Chemical group 0.000 abstract 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 abstract 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 2
- DTCCTIQRPGSLPT-ONEGZZNKSA-N (E)-2-pentenal Chemical compound CC\C=C\C=O DTCCTIQRPGSLPT-ONEGZZNKSA-N 0.000 abstract 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 abstract 2
- TVONJMOVBKMLOM-UHFFFAOYSA-N 2-methylidenebutanenitrile Chemical compound CCC(=C)C#N TVONJMOVBKMLOM-UHFFFAOYSA-N 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001491 aromatic compounds Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- DTCCTIQRPGSLPT-UHFFFAOYSA-N beta-Aethyl-acrolein Natural products CCC=CC=O DTCCTIQRPGSLPT-UHFFFAOYSA-N 0.000 abstract 2
- 235000013844 butane Nutrition 0.000 abstract 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 2
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 abstract 2
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000000536 complexating effect Effects 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(II) bromide Substances [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 abstract 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 abstract 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract 2
- 229960003280 cupric chloride Drugs 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 2
- 230000008020 evaporation Effects 0.000 abstract 2
- 239000012530 fluid Substances 0.000 abstract 2
- 125000000524 functional group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 239000011261 inert gas Substances 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- LABTWGUMFABVFG-UHFFFAOYSA-N methyl propenyl ketone Chemical compound CC=CC(C)=O LABTWGUMFABVFG-UHFFFAOYSA-N 0.000 abstract 2
- 239000011859 microparticle Substances 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- QTYUSOHYEPOHLV-UHFFFAOYSA-N octadiene group Chemical group C=CC=CCCCC QTYUSOHYEPOHLV-UHFFFAOYSA-N 0.000 abstract 2
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 abstract 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 abstract 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 abstract 2
- 239000003208 petroleum Substances 0.000 abstract 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 2
- 229920000098 polyolefin Polymers 0.000 abstract 2
- 239000011148 porous material Substances 0.000 abstract 2
- 238000011084 recovery Methods 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 abstract 2
- 235000010265 sodium sulphite Nutrition 0.000 abstract 2
- 238000004230 steam cracking Methods 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 150000005673 monoalkenes Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cuprous chloride or bromide particles having a porosity of above 10% of the total volume of a particle as 550-10,000 <\>rA pores are prepared by the precipitation of the cuprous halide particles complexed with a complexing agent which forms a stable complex of ratio copper to complexing agent greater than 1:1 from (1) liquids containing the complexed cuprous halide in solution and (2) liquid mixtures of the complexing agents and an activating material selected from monoolefin solvents for the cuprous halide, alcohols, glycols, acids, water containing uncomplexed cuprous halide particles slurred therein, and dissociating the complexed cuprous halide particles to regenerate cuprous chloride or bromide. Suitable complexing agents, gaseous or liquid, may be: carbon monoxide, hydrogen cyanide, C2 to C16 compounds containing one or more of the following functional groups:- (a) C=C, e.g. ethylene, propylene, butylene, isobutylene, pentenes. Olefinic aromatic compounds may also be used, e.g. styrene. (b) C=R=C, where R is C or an alkylene group, e.g. conjugated or non-conjugated aliphatic, cyclic or alicyclic diolefins or polyolefins such as allene, butadiene, isoprene, piperylene, octadienes, cyclohexadiene, cyclo-octadiene, divinyl benzene, cyclododecatriene. (c) -CC-, e.g. aliphatic or alicyclic acetylenes or acetylenes containing additional unsaturation, e.g. acetylene, methylacetylene, propyl acetylene, phenyl acetylene, vinyl acetylene. (d) -CN, aliphatic or alicyclic saturated or unsaturated nitriles such as acetonitrile, acrylonitrile, propionitrile, phenylnitrile, methacrylonitrile, ethacrylonitrile, methane nitrile, ethane nitrile, propane nitrile. Aryl, alkaryl, aryl-alkyl nitriles may also be used. (e) C=O unsaturated carbonyl compounds, e.g. propenal, butenal, pentenal; unsaturated ketones, e.g. 1-butene-3-one, 1,4-pentadiene-3-one, 2 - pentene - 4 - pentadiene - 3 - one, 2 - pentene-4-one. Pure streams, or streams diluted with an inert gas, or natural dilute petroleum streams (e.g. butadiene diluted with butene and butanes) can be used. Reaction conditions are those within which the desired complex is stable, e.g. - 80-80 DEG C., 1 to 165 p.s.i.a. pressure. Suitable solvents in (1) may be aqueous concentrated or dilute inorganic acids, e.g. 2 to 12N HCl or HBr, and concentrated aqueous inorganic solutions. Particles above 10m sizes are prepared by slow precipitation, e.g. <1000 gms./hour/litre. Slow precipitation may be by (a) addition of an antisolvent; (b) change in temperature, (c) evaporation of solvent; or by addition of the complexing agent with or without antisolvent to an uncomplexed cuprous halide solution in a solvent having lower solubility for the complex. Antisolvents may be water, C1 to C10 alcohols, e.g. methanol, ethanol, isopropanol; water-soluble ethers, esters, ketones, e.g. diethyl ether, acetone, methyl ethyl ketone, methyl acetate; sodium hydroxide solution. Precipitation may also be from an uncomplexed solution of cupric chloride or bromide by adding a complexing agent and a reducing agent, e.g. SO2 or Na2SO3. Suitable activating agents in (2) may be C1 to C10 monoalcohols, e.g. methyl, ethyl and n-propyl; C1 to C10 glycols, e.g. ethylene and propylene glycol; C4 to C8 branched or straight chain olefine, e.g. butene-1, isobutylene, pentene-1, hexene-1. The cuprous halide may be above 50% 10-600m single particles or spherical macroparticles composed of continuously joined 5m microparticles. The particles form especially active, complexing agents in the separation of compounds capable of forming a complex with cuprous chloride or cuprous bromide, e.g. in the fluid bed recovery of butadiene from crude butadiene, ethylene separated from steam cracking a C2 stream, acrylonitrile from acetonitrile, carbon monoxide from hydrogen, allene from methyl acetylene, piperlenes from cyclopentene. Preferred complexing and decomplexing conditions in these separation processes are specified.ALSO:Cuprous chloride or bromide particles having a porosity of above 10% of the total volume of a particle as 550-10,000 DEG A. pores are prepared by the precipitation of the cuprous halide particles complexed with a complexing agent which forms a stable complex of ratio copper to complexing agent greater than 1 : 1 from (1) liquids containing the complexed cuprous halide in solution and (2) liquid mixtures of the complexing agents and an activating material selected from monoolefine solvents for the cuprous halide, alcohols, glycols, acids, water containing uncomplexed cuprous halide particles slurred therein, and dissociating the complexed cuprous halide particles to regenerate cuprous chloride or bromide. Suitable complexing agents, gaseous or liquid, may be: carbon monoxide, hydrogen cyanide, C2 to C16 compounds containing one or more of the following functional groups. (a) C = C, e.g. ethylene, propylene, butylene, isobutylene, pentenes. Olefinic aromatic compounds may also be used, e.g. styrene. (b) C = R = C, where R is C or an alkylene group, e.g. conjugated or non-conjugated aliphatic, cyclic or alicyclic diolefines or polyolefines such as allene, butadiene, isoprene, piperylene, octadienes, cyclohexadiene, cyclooctadiene, divinyl benzene, cyclododecatriene. (c) -CC-, e.g. aliphatic or alicyclic acetylenes or acetylenes containing additional unsaturation, e.g. acetylene, methylacetylene, propyl acetylene, phenyl acetylene, vinyl acetylene. (d) -CN, aliphatic or alicyclic saturated or unsaturated nitriles such as acetonitrile, acrylonitrile, proprionitrile, phenylnitrile, methacrylonitrile ethacrylonitrile, methane nitrile, ethane nitrile, propane nitrile. Aryl, alkaryl, arylalkyl nitriles may also be used. (e) C = O unsaturated carbonyl compounds, e.g. propenal, butenal, pentenal; unsaturated ketones, e.g. 1-butene-3-one, 1,4-pentadiene-3-one, 2 - pentene - 4 - pentadiene - 3 - one, 2 - pentene-4-one. Pure streams, or streams diluted with an inert gas, or natural dilute petroleum streams (e.g. butadiene diluted with butene and butanes) can be used. Reaction conditions are those within which the desired complex is stable, e.g. - 80-80 DEG C., 1 to 165 p.s.i.a. pressure. Suitable solvents in (1) may be aqueous concentrated or dilute inorganic acids, e.g. 2 to 12 N -HCl or HBr, and concentrated aqueous inorganic solutions. Particles above 10 m Pl sizes are prepared by slow precipitation, e.g. <1000 gms./ hour/lite. Slow precipitation may be by (a) addition of an antisolvent, (b) change in temperature, (c) evaporation of solvent; or by addition of the complexing agent with or without antisolvent to an uncomplexed cuprous halide solution in a solvent having lower solubility for the complex. Antisolvents may be water, C1 to C10 alcohols, e.g. methanol, ethanol, isopropanol; water soluble ethers, esters, ketones, e.g. diethyl ether, acetone, methyl ethyl ketone, methyl acetate; sodium hydroxide solution. Precipitation may also be from an uncomplexed solution of cupric chloride or bromide by adding a complexing agent and a reducing agent, e.g. SO2 or Na2SO3. Suitable activating agents in (2) may be C1 to C10 monoalcohols, e.g. methyl, ethyl and n-propyl; C1 to C10 glycols, e.g. ethylene and propylene glycol; C4 to C8 branched or straight chain define, e.g. butene-1, isobutylene, pentene-1, hexene-1. The cuprous halide may be above 50% 10-600 m single particles or spherical macroparticles composed of continuously joined 5 m microparticles. The particles form especially active, complexing agents in the separation of compounds capable of forming a complex with curpous chloride or cuprous bromide, e.g. in the fluid bed recovery of butadiene from crude butadiene, ethylene separated from steam cracking a C2 stream, acrylonitrile from acetonitrile, carbon monoxide from hydrogen, allene from methyl acetylene, piperylenes from cyclopentene. Preferred complexing and decomplexing conditions in these separation processes are specified.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2556764A GB1074233A (en) | 1964-06-19 | 1964-06-19 | Cuprous chloride or bromide complexing agents |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2556764A GB1074233A (en) | 1964-06-19 | 1964-06-19 | Cuprous chloride or bromide complexing agents |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1074233A true GB1074233A (en) | 1967-07-05 |
Family
ID=10229786
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2556764A Expired GB1074233A (en) | 1964-06-19 | 1964-06-19 | Cuprous chloride or bromide complexing agents |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1074233A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112391543A (en) * | 2020-10-30 | 2021-02-23 | 衡阳市大宇锌业有限公司 | Device for removing chlorine from zinc sulfate solution and washing cuprous chloride precipitate by using absolute ethyl alcohol |
-
1964
- 1964-06-19 GB GB2556764A patent/GB1074233A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112391543A (en) * | 2020-10-30 | 2021-02-23 | 衡阳市大宇锌业有限公司 | Device for removing chlorine from zinc sulfate solution and washing cuprous chloride precipitate by using absolute ethyl alcohol |
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