TWI297336B - Catalyst promoter for the manufacture of polyphenols - Google Patents
Catalyst promoter for the manufacture of polyphenols Download PDFInfo
- Publication number
- TWI297336B TWI297336B TW090123346A TW90123346A TWI297336B TW I297336 B TWI297336 B TW I297336B TW 090123346 A TW090123346 A TW 090123346A TW 90123346 A TW90123346 A TW 90123346A TW I297336 B TWI297336 B TW I297336B
- Authority
- TW
- Taiwan
- Prior art keywords
- compound
- catalyst
- dithioketal
- catalyst promoter
- reaction zone
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims description 155
- 235000013824 polyphenols Nutrition 0.000 title claims description 32
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 109
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 50
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 46
- 239000000047 product Substances 0.000 claims description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 32
- -1 carboxy compound Chemical class 0.000 claims description 32
- 150000002989 phenols Chemical class 0.000 claims description 28
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 239000000376 reactant Substances 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000011347 resin Substances 0.000 claims description 21
- 229920005989 resin Polymers 0.000 claims description 21
- 150000003573 thiols Chemical class 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 239000003377 acid catalyst Substances 0.000 claims description 18
- 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 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- 238000010494 dissociation reaction Methods 0.000 claims description 17
- 230000005593 dissociations Effects 0.000 claims description 17
- 238000009833 condensation Methods 0.000 claims description 16
- 230000005494 condensation Effects 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000001294 propane Substances 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000011084 recovery Methods 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000006482 condensation reaction Methods 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 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 claims description 6
- 229940106691 bisphenol a Drugs 0.000 claims description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 239000003729 cation exchange resin Substances 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- 238000005341 cation exchange Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 229930004069 diterpene Natural products 0.000 claims description 3
- 150000004141 diterpene derivatives Chemical class 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000013522 chelant Substances 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 2
- 239000003623 enhancer Substances 0.000 claims 4
- 241000894007 species Species 0.000 claims 3
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 1
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims 1
- 241000254173 Coleoptera Species 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 229920002098 polyfluorene Polymers 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 7
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- AVVVXUXMKWPKAJ-UHFFFAOYSA-N 2-ethyl-4-methylphenol Chemical compound CCC1=CC(C)=CC=C1O AVVVXUXMKWPKAJ-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CRSOQBOWXPBRES-QDNHWIQGSA-N 1,3-dideuterio-2,2-dimethylpropane Chemical compound CC(C[2H])(C[2H])C CRSOQBOWXPBRES-QDNHWIQGSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- PXSSNPBEHHJLDH-UHFFFAOYSA-N 2,3,4,5-tetramethylphenol Chemical compound CC1=CC(O)=C(C)C(C)=C1C PXSSNPBEHHJLDH-UHFFFAOYSA-N 0.000 description 1
- KDBZVULQVCUNNA-UHFFFAOYSA-N 2,5-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(O)=C1 KDBZVULQVCUNNA-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- SDJUKATYFRSDAS-UHFFFAOYSA-N 2-tert-butyl-3-methylphenol Chemical compound CC1=CC=CC(O)=C1C(C)(C)C SDJUKATYFRSDAS-UHFFFAOYSA-N 0.000 description 1
- YLBIOIADVQMNJP-UHFFFAOYSA-N 3-(propylamino)propane-1-thiol Chemical compound CCCNCCCS YLBIOIADVQMNJP-UHFFFAOYSA-N 0.000 description 1
- JNJMMVLVPLHOKD-UHFFFAOYSA-N 3-ethyl-2,4-dimethylphenol Chemical compound CCC1=C(C)C=CC(O)=C1C JNJMMVLVPLHOKD-UHFFFAOYSA-N 0.000 description 1
- ZPQAKYPOZRXKFA-UHFFFAOYSA-N 6-Undecanone Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- FECBQHOITGGWFK-UHFFFAOYSA-N acetyl chloride dimethyl sulfate Chemical compound CC(Cl)=O.COS(=O)(=O)OC FECBQHOITGGWFK-UHFFFAOYSA-N 0.000 description 1
- NEBFBVFMEJNMTO-UHFFFAOYSA-N acetylene;benzene Chemical group C#C.C1=CC=CC=C1 NEBFBVFMEJNMTO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 1
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 description 1
- 235000007746 carvacrol Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Natural products CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002601 lanthanoid compounds Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 229920005548 perfluoropolymer Polymers 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/834,460 US6465697B1 (en) | 2001-04-13 | 2001-04-13 | Catalyst promotor for the manufacture of polyphenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI297336B true TWI297336B (en) | 2008-06-01 |
Family
ID=25266994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090123346A TWI297336B (en) | 2001-04-13 | 2001-09-21 | Catalyst promoter for the manufacture of polyphenols |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6465697B1 (enExample) |
| EP (1) | EP1379490A1 (enExample) |
| JP (1) | JP2004532845A (enExample) |
| KR (1) | KR20030093309A (enExample) |
| CN (1) | CN1501902A (enExample) |
| TW (1) | TWI297336B (enExample) |
| WO (1) | WO2002083611A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2819805B1 (fr) * | 2001-01-23 | 2003-03-21 | Atofina | Procede de fabrication du bisphenol a |
| US20040249229A1 (en) * | 2003-06-06 | 2004-12-09 | Gee Jeffery C. | Isomerization of olefins with carboxylic acid |
| US7321069B2 (en) * | 2004-12-17 | 2008-01-22 | General Electric Company | Process for preparing bisphenols |
| KR20070102691A (ko) * | 2005-01-28 | 2007-10-19 | 다우 글로벌 테크놀로지스 인크. | 산 촉매로서 사용하기 전에 양이온 교환 수지를안정화시키는 방법, 및 화학 공정에서의 이러한 안정화된양이온 교환 수지의 용도 |
| ES2371413T3 (es) * | 2006-05-04 | 2012-01-02 | Badger Licensing Llc | Procedimiento mejorado para la fabricación de polifenoles. |
| TWI494163B (zh) | 2011-12-28 | 2015-08-01 | Rohm & Haas | 經處理、促進之離子交換樹脂觸媒之用途及製造方法 |
| TWI494296B (zh) | 2011-12-28 | 2015-08-01 | Rohm & Haas | 經處理、促進之離子交換樹脂觸媒之用途 |
| JP6922575B2 (ja) * | 2016-09-14 | 2021-08-18 | 三菱ケミカル株式会社 | 多価フェノール化合物およびその製造方法 |
| JP7648518B2 (ja) * | 2018-09-05 | 2025-03-18 | バジャー・ライセンシング・エルエルシー | ビスフェノールを製造するプロセス |
| CN115466204B (zh) * | 2022-03-22 | 2024-04-09 | 合肥江新化工科技有限公司 | 一种2,2-二甲硫基丙烷的连续化生产方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2730552A (en) | 1956-01-10 | williamson | ||
| US2229665A (en) * | 1939-08-14 | 1941-01-28 | Du Pont | Preparation of alkyl ketals from mercaptoles and alcohols |
| US2468982A (en) | 1946-10-19 | 1949-05-03 | Goodrich Co B F | Preparation of bis-phenols |
| US2602821A (en) * | 1951-07-23 | 1952-07-08 | Schell Dev Company | Production of bis (hydroxyphenyl) compounds |
| US3394089A (en) | 1964-12-02 | 1968-07-23 | Dow Chemical Co | Ion exchange catalyst for the preparation of bisphenols |
| AU474155B2 (en) * | 1972-12-29 | 1975-07-03 | Monsanto Australia Limited | Production of bis (hydroxyphenyl) alkanes |
| NL7410872A (nl) | 1974-08-14 | 1976-02-17 | Shell Int Research | Werkwijze voor het zuiveren van in polyhydroxy- verbindingen aanwezige ruwe bishydroxyarylver- bindingen. |
| JPS56131534A (en) * | 1980-03-17 | 1981-10-15 | Mitsubishi Chem Ind Ltd | Preparation of bisphenol |
| US4443635A (en) | 1982-12-06 | 1984-04-17 | Shell Oil Company | Removal of color bodies in bisphenol production |
| US4822923A (en) | 1987-10-19 | 1989-04-18 | Shell Oil Company | Isomerization of by-products of bis-phenol synthesis |
| US4859803A (en) | 1988-05-16 | 1989-08-22 | Shell Oil Company | Preparation of bisphenols |
| US5001281A (en) | 1989-08-11 | 1991-03-19 | Shell Oil Company | Isomerization of bis-phenols |
| US5493060A (en) * | 1994-09-16 | 1996-02-20 | Aristech Chemical Corporation | Method of making 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane |
| EP0876319B1 (en) | 1995-12-19 | 2001-06-20 | Shell Internationale Researchmaatschappij B.V. | Improved process for the production of bisphenols |
| ZA972382B (en) | 1996-03-21 | 1997-09-25 | Shell Int Research | Fixed bed reactor packing. |
-
2001
- 2001-04-13 US US09/834,460 patent/US6465697B1/en not_active Expired - Fee Related
- 2001-09-21 TW TW090123346A patent/TWI297336B/zh not_active IP Right Cessation
-
2002
- 2002-04-04 KR KR10-2003-7013343A patent/KR20030093309A/ko not_active Withdrawn
- 2002-04-04 WO PCT/NL2002/000228 patent/WO2002083611A1/en not_active Ceased
- 2002-04-04 CN CNA028081390A patent/CN1501902A/zh active Pending
- 2002-04-04 JP JP2002581369A patent/JP2004532845A/ja active Pending
- 2002-04-04 EP EP02718714A patent/EP1379490A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030093309A (ko) | 2003-12-06 |
| US6465697B1 (en) | 2002-10-15 |
| WO2002083611A1 (en) | 2002-10-24 |
| JP2004532845A (ja) | 2004-10-28 |
| CN1501902A (zh) | 2004-06-02 |
| EP1379490A1 (en) | 2004-01-14 |
| US20020177740A1 (en) | 2002-11-28 |
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| Date | Code | Title | Description |
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| MK4A | Expiration of patent term of an invention patent |