CA1219852A - Catalyseurs de resine, et leur preparation - Google Patents

Catalyseurs de resine, et leur preparation

Info

Publication number: CA1219852A
Authority: CA; Canada
Prior art keywords: metal; sulfonic acid; acid groups; mixtures; process according
Prior art date: 1983-07-25
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

Application number

CA000459561A

Other languages

English (en)

Inventor

Lawrence A. Smith, Jr.

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chemical Research and Licensing Co

Original Assignee

Chemical Research and Licensing Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-07-25

Filing date

1984-07-24

Publication date

1987-03-31

1984-07-24 Application filed by Chemical Research and Licensing Co filed Critical Chemical Research and Licensing Co

1987-03-31 Application granted granted Critical

1987-03-31 Publication of CA1219852A publication Critical patent/CA1219852A/fr

Status Expired legal-status Critical Current

Links

239000011347 resin Substances 0.000 title claims abstract description 58
229920005989 resin Polymers 0.000 title claims abstract description 58
238000000034 method Methods 0.000 title claims abstract description 53
239000003054 catalyst Substances 0.000 title abstract description 70
238000002360 preparation method Methods 0.000 title abstract description 4
239000000203 mixture Substances 0.000 claims abstract description 58
125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 46
229910021645 metal ion Inorganic materials 0.000 claims abstract description 36
229910052751 metal Inorganic materials 0.000 claims abstract description 32
239000002184 metal Substances 0.000 claims abstract description 32
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 25
-1 ammonium ions Chemical class 0.000 claims abstract description 23
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 16
229910052802 copper Inorganic materials 0.000 claims abstract description 16
229910052742 iron Inorganic materials 0.000 claims abstract description 16
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 15
229910052725 zinc Inorganic materials 0.000 claims abstract description 14
229910052782 aluminium Inorganic materials 0.000 claims abstract description 13
229910052759 nickel Inorganic materials 0.000 claims abstract description 12
239000007864 aqueous solution Substances 0.000 claims abstract description 10
150000001491 aromatic compounds Chemical class 0.000 claims abstract description 8
229920006216 polyvinyl aromatic Polymers 0.000 claims abstract description 8
150000002500 ions Chemical class 0.000 claims abstract description 7
230000008569 process Effects 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 22
239000011159 matrix material Substances 0.000 claims description 13
229910001413 alkali metal ion Inorganic materials 0.000 claims description 12
150000001340 alkali metals Chemical class 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 11
230000000737 periodic effect Effects 0.000 claims description 11
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 10
239000012808 vapor phase Substances 0.000 claims description 10
238000005661 deetherification reaction Methods 0.000 claims description 9
229910052708 sodium Inorganic materials 0.000 claims description 9
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
229910052791 calcium Inorganic materials 0.000 claims description 8
229910052749 magnesium Inorganic materials 0.000 claims description 8
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 claims description 8
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
239000007787 solid Substances 0.000 claims description 7
229910052700 potassium Inorganic materials 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
229910052788 barium Inorganic materials 0.000 claims description 5
150000002170 ethers Chemical class 0.000 claims description 4
229910052712 strontium Inorganic materials 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910052761 rare earth metal Inorganic materials 0.000 claims description 2
150000002910 rare earth metals Chemical class 0.000 claims description 2
239000011949 solid catalyst Substances 0.000 claims 16
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 3
229910052744 lithium Inorganic materials 0.000 claims 3
UPOMCDPCTBJJDA-UHFFFAOYSA-N 2-methyl-1-[(2-methylpropan-2-yl)oxy]propane Chemical group CC(C)COC(C)(C)C UPOMCDPCTBJJDA-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 abstract description 18
150000003863 ammonium salts Chemical class 0.000 abstract description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 14
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000010949 copper Substances 0.000 description 10
239000003729 cation exchange resin Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000007791 liquid phase Substances 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 8
150000001336 alkenes Chemical class 0.000 description 8
229940023913 cation exchange resins Drugs 0.000 description 8
239000012266 salt solution Substances 0.000 description 8
239000011701 zinc Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
239000008399 tap water Substances 0.000 description 7
235000020679 tap water Nutrition 0.000 description 7
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
238000006386 neutralization reaction Methods 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000008367 deionised water Substances 0.000 description 5
229910021641 deionized water Inorganic materials 0.000 description 5
238000010494 dissociation reaction Methods 0.000 description 5
230000005593 dissociations Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
238000006297 dehydration reaction Methods 0.000 description 4
230000036571 hydration Effects 0.000 description 4
238000006703 hydration reaction Methods 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
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 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
238000005342 ion exchange Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
JJNQHLLBFBGKEL-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]butane Chemical compound CCCCOC(C)(C)C JJNQHLLBFBGKEL-UHFFFAOYSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical group CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
ZQAYBCWERYRAMF-UHFFFAOYSA-N 1-methoxy-3-methylbutane Chemical compound COCCC(C)C ZQAYBCWERYRAMF-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052748 manganese Inorganic materials 0.000 description 2
239000011572 manganese Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000004005 microsphere Substances 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229910052709 silver Inorganic materials 0.000 description 2
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
229910000368 zinc sulfate Inorganic materials 0.000 description 2
229960001763 zinc sulfate Drugs 0.000 description 2
XGLHRCWEOMNVKS-ZCFIWIBFSA-N (2r)-1-methoxy-2-methylbutane Chemical group CC[C@@H](C)COC XGLHRCWEOMNVKS-ZCFIWIBFSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
BWRSHLROMAZEBM-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]pentane Chemical group CCCCCOC(C)(C)C BWRSHLROMAZEBM-UHFFFAOYSA-N 0.000 description 1
ZCKODQRJCONMMC-UHFFFAOYSA-N 1-[2,3-bis(ethenyl)phenoxy]-2,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(OC=2C(=C(C=C)C=CC=2)C=C)=C1C=C ZCKODQRJCONMMC-UHFFFAOYSA-N 0.000 description 1
VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 1
WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
FITVQUMLGWRKKG-UHFFFAOYSA-N 2-methyl-2-propoxypropane Chemical compound CCCOC(C)(C)C FITVQUMLGWRKKG-UHFFFAOYSA-N 0.000 description 1
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229910052693 Europium Inorganic materials 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910052779 Neodymium Inorganic materials 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
108091006629 SLC13A2 Proteins 0.000 description 1
229910052772 Samarium Inorganic materials 0.000 description 1
241001256311 Selenis Species 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000001450 anions Chemical group 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
NKQIMNKPSDEDMO-UHFFFAOYSA-L barium bromide Chemical compound [Br-].[Br-].[Ba+2] NKQIMNKPSDEDMO-UHFFFAOYSA-L 0.000 description 1
229910001620 barium bromide Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
238000011021 bench scale process Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
229910001622 calcium bromide Inorganic materials 0.000 description 1
229940059251 calcium bromide Drugs 0.000 description 1
WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
229910001431 copper ion Inorganic materials 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
238000010438 heat treatment Methods 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
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229910000358 iron sulfate Inorganic materials 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
239000001282 iso-butane Substances 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
GLNWILHOFOBOFD-UHFFFAOYSA-N lithium sulfide Chemical compound [Li+].[Li+].[S-2] GLNWILHOFOBOFD-UHFFFAOYSA-N 0.000 description 1
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
235000011285 magnesium acetate Nutrition 0.000 description 1
239000011654 magnesium acetate Substances 0.000 description 1
229940069446 magnesium acetate Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
229910052758 niobium Inorganic materials 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920001447 polyvinyl benzene Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
239000012508 resin bead Substances 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000004332 silver Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
YJPVTCSBVRMESK-UHFFFAOYSA-L strontium bromide Chemical compound [Br-].[Br-].[Sr+2] YJPVTCSBVRMESK-UHFFFAOYSA-L 0.000 description 1
229910001625 strontium bromide Inorganic materials 0.000 description 1
229940074155 strontium bromide Drugs 0.000 description 1
230000001180 sulfating effect Effects 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
238000005690 transetherification reaction Methods 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
238000004457 water analysis Methods 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Landscapes

Catalysts (AREA)

CA000459561A 1983-07-25 1984-07-24 Catalyseurs de resine, et leur preparation Expired CA1219852A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US51722083A	1983-07-25	1983-07-25
US517,220		1983-07-25

Publications (1)

Publication Number	Publication Date
CA1219852A true CA1219852A (fr)	1987-03-31

Family

ID=24058883

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000459561A Expired CA1219852A (fr)	1983-07-25	1984-07-24	Catalyseurs de resine, et leur preparation

Country Status (1)

Country	Link
CA (1)	CA1219852A (fr)

1984
- 1984-07-24 CA CA000459561A patent/CA1219852A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-07-24	MKEX	Expiry

Publication	Publication Date	Title
US4551567A (en)	1985-11-05	Deetherification process
US4629710A (en)	1986-12-16	Resin catalysts and method of preparation
US3409691A (en)	1968-11-05	Porous cation exchange resins as selective sorbents in organic systems
US4087471A (en)	1978-05-02	Fixed bed process for the production of t-butanol
PL114626B1 (en)	1981-02-28	Process for preparing pure methyl tert-butyl ether
CA1185273A (fr)	1985-04-09	Procede d'obtention de tert.-olefines pures
TW200301244A (en)	2003-07-01	Metal-doped sulfonated ion exchange resin catalysts
CA1219852A (fr)	1987-03-31	Catalyseurs de resine, et leur preparation
US5157162A (en)	1992-10-20	One step synthesis of methyl t-butyl ether from t-butanol using fluorosulfonic acid-modified clay catalysts
EP0579153B1 (fr)	1998-04-08	Procédé de préparation d'alcools tertiaires
US4861923A (en)	1989-08-29	Hydration of propylene to isopropyl alcohol over solid superacidic perfluorinated sulfonic acid catalysts
JP4095274B2 (ja)	2008-06-04	構造化多目的パッキングを用いる反応性精留におけるオレフィンの水和による第三級アルコールの製造方法
US5183947A (en)	1993-02-02	One step synthesis of methyl t-butyl ether from t-butanol using fluorophosphoric acid-modified clay catalysts
US5214218A (en)	1993-05-25	One step synthesis of methyl t-butyl ether from t-butanol using haloacid-modified clay catalysts
EP0047906B1 (fr)	1984-06-13	Procédé de préparation d'éthers aliphatiques
JPS6039330B2 (ja)	1985-09-05	オレフインの水和ならびにグライコ−ルのエ−テル化方法
US8492603B2 (en)	2013-07-23	Selectivated isoolefin dimerization using metalized resins
US5399788A (en)	1995-03-21	Two-stage process for producing diisopropyl ether using hydration
JPS6043049B2 (ja)	1985-09-26	ｎ−ブテンの精製方法
JPH0351693B2 (fr)	1991-08-07
JP3508164B2 (ja)	2004-03-22	第３級アルコールの製造法及びその触媒の製造法
JPS5938933B2 (ja)	1984-09-20	第三級アルキルエ−テルの連続的製造法
KR830002476B1 (ko)	1983-10-26	메틸 t-부틸 에테르의 제조방법
JP2000191566A (ja)	2000-07-11	アルコ―ルの製造方法
US4393249A (en)	1983-07-12	Process for removing alkynes from C4 hydrocarbon mixtures