CA2230272A1 - Isomerization of bisphenols - Google Patents
Isomerization of bisphenols Download PDFInfo
- Publication number
- CA2230272A1 CA2230272A1 CA002230272A CA2230272A CA2230272A1 CA 2230272 A1 CA2230272 A1 CA 2230272A1 CA 002230272 A CA002230272 A CA 002230272A CA 2230272 A CA2230272 A CA 2230272A CA 2230272 A1 CA2230272 A1 CA 2230272A1
- Authority
- CA
- Canada
- Prior art keywords
- tho
- acid
- produce
- compound
- isomerization
- 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.)
- Abandoned
Links
- 238000006317 isomerization reaction Methods 0.000 title claims description 34
- 229930185605 Bisphenol Natural products 0.000 title claims description 9
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 111
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 91
- -1 mercaptosulfonic acid compound Chemical class 0.000 claims abstract description 64
- 150000002576 ketones Chemical class 0.000 claims abstract description 24
- 238000009833 condensation Methods 0.000 claims abstract description 6
- 230000005494 condensation Effects 0.000 claims abstract description 6
- 239000007858 starting material Substances 0.000 claims abstract description 6
- 125000005647 linker group Chemical group 0.000 claims abstract 11
- 150000001299 aldehydes Chemical class 0.000 claims abstract 6
- 239000002253 acid Substances 0.000 claims description 232
- 239000000203 mixture Substances 0.000 claims description 130
- 238000006243 chemical reaction Methods 0.000 claims description 111
- 238000000034 method Methods 0.000 claims description 89
- 230000008569 process Effects 0.000 claims description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
- 229920000642 polymer Polymers 0.000 claims description 74
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 claims description 63
- 239000000047 product Substances 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 35
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims description 33
- 239000011541 reaction mixture Substances 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 25
- 239000011347 resin Substances 0.000 claims description 25
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 229910006069 SO3H Inorganic materials 0.000 claims description 22
- 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 22
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 239000012043 crude product Substances 0.000 claims description 18
- 238000005260 corrosion Methods 0.000 claims description 16
- 230000007797 corrosion Effects 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000008053 sultones Chemical class 0.000 claims description 10
- 239000003377 acid catalyst Substances 0.000 claims description 7
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 150000007944 thiolates Chemical class 0.000 claims description 5
- 239000011149 active material Substances 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000005275 alkylenearyl group Chemical group 0.000 claims 13
- 229920005990 polystyrene resin Polymers 0.000 claims 10
- 239000004793 Polystyrene Substances 0.000 claims 6
- 229920002223 polystyrene Polymers 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 229910001220 stainless steel Inorganic materials 0.000 claims 4
- 239000010935 stainless steel Substances 0.000 claims 4
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical group OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims 3
- 150000002989 phenols Chemical class 0.000 claims 3
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims 2
- 238000012935 Averaging Methods 0.000 claims 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000002198 insoluble material Substances 0.000 claims 2
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims 1
- YPLVPFUSXYSHJD-UHFFFAOYSA-N 11-bromoundec-1-ene Chemical compound BrCCCCCCCCCC=C YPLVPFUSXYSHJD-UHFFFAOYSA-N 0.000 claims 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 claims 1
- XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 claims 1
- XZBXAYCCBFTQHH-UHFFFAOYSA-N 3-chloropropylbenzene Chemical compound ClCCCC1=CC=CC=C1 XZBXAYCCBFTQHH-UHFFFAOYSA-N 0.000 claims 1
- OBDVFOBWBHMJDG-UHFFFAOYSA-N 3-mercapto-1-propanesulfonic acid Chemical compound OS(=O)(=O)CCCS OBDVFOBWBHMJDG-UHFFFAOYSA-N 0.000 claims 1
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 claims 1
- XPBQQAHIVODAIC-UHFFFAOYSA-N 4-bromobutylbenzene Chemical compound BrCCCCC1=CC=CC=C1 XPBQQAHIVODAIC-UHFFFAOYSA-N 0.000 claims 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 claims 1
- ISOQNEPBGIJCLU-UHFFFAOYSA-N 4-sulfanylbutane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCS ISOQNEPBGIJCLU-UHFFFAOYSA-N 0.000 claims 1
- LPNANKDXVBMDKE-UHFFFAOYSA-N 5-bromopent-1-ene Chemical compound BrCCCC=C LPNANKDXVBMDKE-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 239000003957 anion exchange resin Substances 0.000 claims 1
- 239000006286 aqueous extract Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000002638 heterogeneous catalyst Substances 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 description 88
- 238000005804 alkylation reaction Methods 0.000 description 48
- XXONZJKORUUFIZ-UHFFFAOYSA-N 3-sulfanylpyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=CC=C1S XXONZJKORUUFIZ-UHFFFAOYSA-N 0.000 description 46
- 238000004128 high performance liquid chromatography Methods 0.000 description 46
- 230000029936 alkylation Effects 0.000 description 42
- 238000004458 analytical method Methods 0.000 description 41
- 239000002002 slurry Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000011324 bead Substances 0.000 description 26
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 25
- 239000013078 crystal Substances 0.000 description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 24
- 241001167018 Aroa Species 0.000 description 22
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- 239000011734 sodium Substances 0.000 description 20
- 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 19
- 241001077660 Molo Species 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 10
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 10
- 241000282326 Felis catus Species 0.000 description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
- 241000283984 Rodentia Species 0.000 description 10
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 10
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 10
- 150000002085 enols Chemical class 0.000 description 10
- 229910052744 lithium Inorganic materials 0.000 description 10
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 10
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 9
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
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- 239000011521 glass Substances 0.000 description 8
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 8
- 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 7
- 230000002378 acidificating effect Effects 0.000 description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
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- 238000013461 design Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 102000004405 Collectins Human genes 0.000 description 5
- 108090000909 Collectins Proteins 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
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- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- 241000357297 Atypichthys strigatus Species 0.000 description 4
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- 125000003545 alkoxy group Chemical group 0.000 description 4
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- 101100537280 Caenorhabditis elegans ddp-1 gene Proteins 0.000 description 3
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- 101100077702 Escherichia coli (strain K12) mog gene Proteins 0.000 description 3
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- VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 238000006177 thiolation reaction Methods 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-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
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 2
- 241001527902 Aratus Species 0.000 description 2
- OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 101100480530 Danio rerio tal1 gene Proteins 0.000 description 2
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- YXHVCZZLWZYHSA-FPLPWBNLSA-N Ginkgoic acid Chemical compound CCCCCC\C=C/CCCCCCCC1=CC=CC(O)=C1C(O)=O YXHVCZZLWZYHSA-FPLPWBNLSA-N 0.000 description 2
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 101150115956 slc25a26 gene Proteins 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical group O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 229940028870 thiola Drugs 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 101150093555 treA gene Proteins 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0217—Mercaptans or thiols
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US275695P | 1995-08-24 | 1995-08-24 | |
| US60/002,756 | 1995-08-24 | ||
| PCT/US1996/013683 WO1997008122A1 (en) | 1995-08-24 | 1996-08-23 | Isomerization of bisphenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2230272A1 true CA2230272A1 (en) | 1997-03-06 |
Family
ID=21702352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002230272A Abandoned CA2230272A1 (en) | 1995-08-24 | 1996-08-23 | Isomerization of bisphenols |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0848693A4 (cs) |
| CN (1) | CN1200105A (cs) |
| CA (1) | CA2230272A1 (cs) |
| CZ (1) | CZ55698A3 (cs) |
| WO (1) | WO1997008122A1 (cs) |
| ZA (1) | ZA967195B (cs) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6620939B2 (en) | 2001-09-18 | 2003-09-16 | General Electric Company | Method for producing bisphenol catalysts and bisphenols |
| US6703530B2 (en) | 2002-02-28 | 2004-03-09 | General Electric Company | Chemical reactor system and process |
| US7112702B2 (en) | 2002-12-12 | 2006-09-26 | General Electric Company | Process for the synthesis of bisphenol |
| US7132575B2 (en) | 2003-07-01 | 2006-11-07 | General Electric Company | Process for the synthesis of bisphenol |
| US8735634B2 (en) | 2011-05-02 | 2014-05-27 | Sabic Innovative Plastics Ip B.V. | Promoter catalyst system with solvent purification |
| US9290618B2 (en) | 2011-08-05 | 2016-03-22 | Sabic Global Technologies B.V. | Polycarbonate compositions having enhanced optical properties, methods of making and articles comprising the polycarbonate compositions |
| US9490405B2 (en) | 2012-02-03 | 2016-11-08 | Sabic Innovative Plastics Ip B.V. | Light emitting diode device and method for production thereof containing conversion material chemistry |
| EP3284802A1 (en) | 2012-02-29 | 2018-02-21 | SABIC Global Technologies B.V. | Polycarbonate compositions containing conversion material chemistry and having enhanced optical properties, methods of making and articles comprising the same |
| WO2013130606A2 (en) | 2012-02-29 | 2013-09-06 | Sabic Innovative Plastics Ip B.V. | Polycarbonate made from low sulfur bisphenol a and containing converions material chemistry, and articles made therefrom |
| US9346949B2 (en) | 2013-02-12 | 2016-05-24 | Sabic Global Technologies B.V. | High reflectance polycarbonate |
| PL219656B1 (pl) | 2012-08-23 | 2015-06-30 | Inst Ciężkiej Syntezy Organicznej Blachownia | Sposób transformacji produktów ubocznych w procesie syntezy bisfenolu A |
| EP2912107B1 (en) | 2012-10-25 | 2018-03-28 | SABIC Global Technologies B.V. | Light emitting diode devices, method of manufacture, uses thereof |
| WO2014186548A1 (en) | 2013-05-16 | 2014-11-20 | Sabic Innovative Plastics Ip B.V. | Branched polycarbonate compositions having conversion material chemistry and articles thereof |
| CN105492519B (zh) | 2013-05-29 | 2018-03-09 | 沙特基础全球技术有限公司 | 具有颜色稳定的热塑性光传输制品的照明设备 |
| CN109790095A (zh) * | 2016-12-20 | 2019-05-21 | 沙特基础工业全球技术有限公司 | 制造双酚a的方法 |
| DE112020003083T5 (de) * | 2019-06-28 | 2022-03-10 | Ptt Global Chemical Public Company Limited | Verfahren zur isomerisierung eines produkts, das aus der bisphenolherstellung über eine kondensationsreaktion von keton und phenol erhalten wurde |
| CN118324607B (zh) * | 2024-04-11 | 2024-10-01 | 天津大学 | 一种降低双酚a反应系统中副产物的工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2923744A (en) * | 1960-02-02 | Preparation of bis-z | ||
| DE3439484A1 (de) * | 1984-10-27 | 1986-05-07 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von 9,9-bis-(4-hydroxyphenyl)-fluoren |
| DE3835204A1 (de) * | 1988-10-15 | 1990-04-19 | Bayer Ag | Verfahren zur herstellung von dihydroxidiarylalkanen |
| IT1243990B (it) * | 1990-10-30 | 1994-06-28 | Minnesota Mining & Mfg | Procedimento per preparare prodotti del bisfenolo fluorene |
| US5463140A (en) * | 1994-08-31 | 1995-10-31 | The Dow Chemical Company | Process for making polyphenols from ketones or aldehydes and phenols |
-
1996
- 1996-08-23 ZA ZA9607195A patent/ZA967195B/xx unknown
- 1996-08-23 CN CN96197659A patent/CN1200105A/zh active Pending
- 1996-08-23 CA CA002230272A patent/CA2230272A1/en not_active Abandoned
- 1996-08-23 WO PCT/US1996/013683 patent/WO1997008122A1/en not_active Application Discontinuation
- 1996-08-23 CZ CZ98556A patent/CZ55698A3/cs unknown
- 1996-08-23 EP EP96930593A patent/EP0848693A4/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CZ55698A3 (cs) | 1998-08-12 |
| EP0848693A4 (en) | 1999-03-17 |
| CN1200105A (zh) | 1998-11-25 |
| EP0848693A1 (en) | 1998-06-24 |
| ZA967195B (en) | 1998-02-23 |
| WO1997008122A1 (en) | 1997-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |