JPH02719A - レゾルシノールの製造方法 - Google Patents
レゾルシノールの製造方法Info
- Publication number
- JPH02719A JPH02719A JP63324712A JP32471288A JPH02719A JP H02719 A JPH02719 A JP H02719A JP 63324712 A JP63324712 A JP 63324712A JP 32471288 A JP32471288 A JP 32471288A JP H02719 A JPH02719 A JP H02719A
- Authority
- JP
- Japan
- Prior art keywords
- dhp
- dipb
- diisopropylbenzene
- resorcinol
- hhp
- 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.)
- Granted
Links
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title claims abstract description 160
- 238000002360 preparation method Methods 0.000 title description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 129
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 66
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 238000000605 extraction Methods 0.000 claims abstract description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims abstract description 6
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 51
- 238000004519 manufacturing process Methods 0.000 claims description 40
- 229910015900 BF3 Inorganic materials 0.000 claims description 29
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical group CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 23
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- 238000004064 recycling Methods 0.000 claims description 9
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 6
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 239000002808 molecular sieve Substances 0.000 claims description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- IROSBXFYXRIPRU-UHFFFAOYSA-N 1,3-bis(2-hydroperoxypropan-2-yl)benzene Chemical compound OOC(C)(C)C1=CC=CC(C(C)(C)OO)=C1 IROSBXFYXRIPRU-UHFFFAOYSA-N 0.000 claims 9
- QBPHJWZNDSKPJL-UHFFFAOYSA-N m-diisopropylbenzene hydroxyhydroperoxide Chemical compound OOO.CC(C)C1=CC=CC(C(C)C)=C1 QBPHJWZNDSKPJL-UHFFFAOYSA-N 0.000 claims 3
- PMMDDCBKWIVAMR-UHFFFAOYSA-N benzene;hydrogen peroxide Chemical compound OO.OO.C1=CC=CC=C1 PMMDDCBKWIVAMR-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 238000007670 refining Methods 0.000 claims 1
- 101000648997 Homo sapiens Tripartite motif-containing protein 44 Proteins 0.000 abstract description 53
- 102100028017 Tripartite motif-containing protein 44 Human genes 0.000 abstract description 53
- 230000008569 process Effects 0.000 abstract description 17
- 239000003513 alkali Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- ADNTWSHRSHPGHG-UHFFFAOYSA-N 1,3-di(propan-2-yl)benzene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC(C(C)C)=C1 ADNTWSHRSHPGHG-UHFFFAOYSA-N 0.000 abstract 1
- VDKMFOYCLHRGJG-UHFFFAOYSA-N OOOO.CC(C)C1=CC=CC(C(C)C)=C1 Chemical compound OOOO.CC(C)C1=CC=CC(C(C)C)=C1 VDKMFOYCLHRGJG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 78
- 229960001755 resorcinol Drugs 0.000 description 78
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 73
- 235000011121 sodium hydroxide Nutrition 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 28
- 238000002474 experimental method Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 24
- 238000004128 high performance liquid chromatography Methods 0.000 description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000004448 titration Methods 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 13
- 238000006386 neutralization reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 238000001030 gas--liquid chromatography Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000003518 caustics Substances 0.000 description 5
- 239000013256 coordination polymer Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NHUDOXBAZXTOGS-UHFFFAOYSA-N 1,5,7-trimethyl-2,3-dihydro-1h-indene Chemical compound CC1=CC(C)=C2C(C)CCC2=C1 NHUDOXBAZXTOGS-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 101000572892 Homo sapiens Migration and invasion-inhibitory protein Proteins 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 102100026584 Migration and invasion-inhibitory protein Human genes 0.000 description 2
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- -1 ketone hydroperoxide Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 238000005502 peroxidation Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SBUBPFHJZHQNNT-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene hydrogen peroxide Chemical compound OO.OO.CC(C)C1=CC=CC=C1C(C)C SBUBPFHJZHQNNT-UHFFFAOYSA-N 0.000 description 1
- VCHOFVSNWYPAEF-UHFFFAOYSA-N 1-(3-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(C(C)=O)=C1 VCHOFVSNWYPAEF-UHFFFAOYSA-N 0.000 description 1
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 description 1
- CHKAAJMOZXVUCU-UHFFFAOYSA-N 2-propan-2-yloxypropan-2-ylbenzene Chemical compound CC(C)OC(C)(C)C1=CC=CC=C1 CHKAAJMOZXVUCU-UHFFFAOYSA-N 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 101150048270 DHPS gene Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000030781 Ippa Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000700647 Variola virus Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- 239000008380 degradant Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
- FOGHPENQGFYWSI-UHFFFAOYSA-N methyl 4-oxohexanoate Chemical compound CCC(=O)CCC(=O)OC FOGHPENQGFYWSI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 230000003319 supportive effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CILQKUOYIAVYFK-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1 CILQKUOYIAVYFK-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/12—Compounds containing six-membered aromatic rings with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring
-
- 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
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/136,317 US4849549A (en) | 1987-12-22 | 1987-12-22 | Process for preparation of resorcinol |
| US136317 | 1987-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02719A true JPH02719A (ja) | 1990-01-05 |
| JPH0587056B2 JPH0587056B2 (en, 2012) | 1993-12-15 |
Family
ID=22472324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63324712A Granted JPH02719A (ja) | 1987-12-22 | 1988-12-22 | レゾルシノールの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4849549A (en, 2012) |
| EP (1) | EP0322245B1 (en, 2012) |
| JP (1) | JPH02719A (en, 2012) |
| BR (1) | BR8806834A (en, 2012) |
| CA (1) | CA1319708C (en, 2012) |
| DE (1) | DE3887858T2 (en, 2012) |
| MX (1) | MX163596B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007223922A (ja) * | 2006-02-22 | 2007-09-06 | Sumitomo Chemical Co Ltd | フェノール類の製造方法 |
| JP2007246512A (ja) * | 2006-02-17 | 2007-09-27 | Sumitomo Chemical Co Ltd | ジヒドロキシベンゼン及びジイソプロピルベンゼンジカルビノールの製造方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6350921B1 (en) | 1998-02-24 | 2002-02-26 | Indspec Chemical Corporation | Process for the production of a dihydroxybenzene and dicarbinol from diisopropylbenzene |
| US6943270B2 (en) * | 2000-03-03 | 2005-09-13 | Illa International, Llc | High selective method of producing cumene hydroperoxide, phenol and acetone in an oxidation by-product conversion process |
| CN114426463B (zh) * | 2020-10-13 | 2024-05-28 | 中国石油化工股份有限公司 | 制备间苯二酚的方法 |
| CN113135819B (zh) * | 2021-04-29 | 2022-07-15 | 北京工业大学 | 一种提高间二异丙苯氧化制备间苯二酚的收率的方法 |
| CN115583906B (zh) * | 2021-07-05 | 2024-08-30 | 中国石油化工股份有限公司 | 间二异丙苯氧化液的处理方法和回用方法以及间苯二酚的生产方法 |
| CN115010582B (zh) * | 2022-06-29 | 2023-05-30 | 万华化学集团股份有限公司 | 一种间苯二酚的制备方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2856432A (en) * | 1953-09-04 | 1958-10-14 | Hercules Powder Co Ltd | Aromatic dihydroperoxide production |
| DE1134375B (de) * | 1959-07-13 | 1962-08-09 | Phenolchemie Ges Mit Beschraen | Verfahren zur Gewinnung von alkylaromatischen Dihydroperoxyden aus waessrigen Alkaliloesungen |
| US3497561A (en) * | 1967-06-08 | 1970-02-24 | Lummus Co | Decomposition of hydroperoxides |
| US4229596A (en) * | 1970-03-05 | 1980-10-21 | The Goodyear Tire & Rubber Company | Process for the continuous isolation of dihydric phenols |
| CA935441A (en) * | 1971-03-11 | 1973-10-16 | Union Carbide Corporation | Process for the purification and recovery of an aromatic hydroxyl compound |
| JPS5312499B2 (en, 2012) * | 1972-05-23 | 1978-05-01 | ||
| JPS5534777B2 (en, 2012) * | 1972-06-20 | 1980-09-09 | ||
| JPS5534778B2 (en, 2012) * | 1972-07-05 | 1980-09-09 | ||
| US3953521A (en) * | 1972-08-23 | 1976-04-27 | Sumitomo Chemical Company, Limited | Process for the continuous production of dihydroperoxides |
| JPS5146095B2 (en, 2012) * | 1972-09-08 | 1976-12-07 | ||
| JPS5136741B2 (en, 2012) * | 1972-11-21 | 1976-10-12 | ||
| JPS5312500B2 (en, 2012) * | 1972-11-21 | 1978-05-01 | ||
| JPS59489B2 (ja) * | 1972-11-21 | 1984-01-07 | 住友化学工業株式会社 | ジハイドロパ−オキサイドの分解法 |
| US3929920A (en) * | 1973-05-31 | 1975-12-30 | Daikin Ind Ltd | Process for continuous fluorination of carbon |
| JPS5129457A (en) * | 1974-09-03 | 1976-03-12 | Sumitomo Chemical Co | Jihaidoropaaokisaidonochushutsuho |
| JPS5852972B2 (ja) * | 1976-08-18 | 1983-11-26 | 三井化学株式会社 | 二価フエノ−ル類の製造方法 |
| JPS6017783B2 (ja) * | 1977-10-31 | 1985-05-07 | 三井化学株式会社 | ｍ−ジイソプロピルベンゼンの酸化方法 |
| JPS599532B2 (ja) * | 1978-05-30 | 1984-03-03 | 三井化学株式会社 | レゾルシンの回収方法 |
| JPS5511513A (en) * | 1978-07-10 | 1980-01-26 | Mitsui Petrochem Ind Ltd | Purification of resorcinol |
| JPS6024788B2 (ja) * | 1978-10-17 | 1985-06-14 | 三井化学株式会社 | 芳香族ヒドロペルオキシドの製造方法 |
| US4238417A (en) * | 1979-08-15 | 1980-12-09 | Gulf Research & Development Company | Decomposition of cumene hydroperoxide and recovery of boron trifluoride catalyst |
| US4308110A (en) * | 1979-10-09 | 1981-12-29 | Sumitomo Chemical Company Limited | Process for separation and purification of dihydric phenols |
| JPS6050171B2 (ja) * | 1979-11-12 | 1985-11-07 | 三井化学株式会社 | レゾルシンの製造方法 |
| CA1115733A (en) * | 1979-12-27 | 1982-01-05 | Hirohiko Nambu | Method for recovering resorcinol |
| US4339613A (en) * | 1980-03-14 | 1982-07-13 | Pcuk Produits Chimiques Ugine Kuhlmann | Superacid catalyzed preparation of resorcinol from meta-diisopropylbenzene |
| JPS5896034A (ja) * | 1981-12-01 | 1983-06-07 | Sumitomo Chem Co Ltd | フロログルシンの製造法 |
| US4670609A (en) * | 1982-09-29 | 1987-06-02 | The Goodyear Tire & Rubber Company | Dihydric phenol recovery process |
-
1987
- 1987-12-22 US US07/136,317 patent/US4849549A/en not_active Expired - Lifetime
-
1988
- 1988-12-21 CA CA000586672A patent/CA1319708C/en not_active Expired - Lifetime
- 1988-12-22 MX MX14293A patent/MX163596B/es unknown
- 1988-12-22 JP JP63324712A patent/JPH02719A/ja active Granted
- 1988-12-22 EP EP88312259A patent/EP0322245B1/en not_active Expired - Lifetime
- 1988-12-22 BR BR888806834A patent/BR8806834A/pt not_active IP Right Cessation
- 1988-12-22 DE DE3887858T patent/DE3887858T2/de not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007246512A (ja) * | 2006-02-17 | 2007-09-27 | Sumitomo Chemical Co Ltd | ジヒドロキシベンゼン及びジイソプロピルベンゼンジカルビノールの製造方法 |
| JP2007223922A (ja) * | 2006-02-22 | 2007-09-06 | Sumitomo Chemical Co Ltd | フェノール類の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0587056B2 (en, 2012) | 1993-12-15 |
| DE3887858T2 (de) | 1994-05-19 |
| EP0322245A3 (en) | 1991-04-10 |
| EP0322245B1 (en) | 1994-02-16 |
| MX163596B (es) | 1992-06-04 |
| BR8806834A (pt) | 1989-08-29 |
| EP0322245A2 (en) | 1989-06-28 |
| CA1319708C (en) | 1993-06-29 |
| US4849549A (en) | 1989-07-18 |
| DE3887858D1 (de) | 1994-03-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2737480A (en) | Recovery of acetone and phenol from cumene hydroperoxide decomposition product | |
| US4016213A (en) | Recovery of phenol, acetone and dimethyl phenyl carbinol from cumene oxidation product | |
| JPS5852972B2 (ja) | 二価フエノ−ル類の製造方法 | |
| US4331824A (en) | Process for preparation of high purity isobutylene | |
| JPS5814411B2 (ja) | フエノ−ル類の精製法 | |
| US7482493B2 (en) | Method for the production of phenol and acetone | |
| JPH02719A (ja) | レゾルシノールの製造方法 | |
| US4347393A (en) | Process for continuous production of cumene and/or diisopropylbenzene | |
| US2856432A (en) | Aromatic dihydroperoxide production | |
| EP1339661B1 (en) | Process for separating phenol from a mixture comprising at least hydroxyacetone, cumene, water and phenol | |
| US3308163A (en) | Process for preparing peroxy compounds | |
| US4283568A (en) | Process for the recovery of phenol from a reaction mixture resulting from the acid cleavage of cumene hydroperoxide | |
| US4339615A (en) | Process for producing resorcinol | |
| JPH09110766A (ja) | ビスフェノールａの製造方法 | |
| US2573947A (en) | Preparation of hydroperoxide compounds | |
| EP0322246B1 (en) | Oxidation and subsequent decomposition of dihydroperoxide | |
| EP0032255B1 (en) | Process for the direct neutralisation of a reaction mixture resulting from the acid cleavage of an alpha-hydroxy derivative of an alkyl-substituted aromatic hydrocarbon and the removal of the formed salt | |
| US20160008735A1 (en) | Process for purifying hydrocarbons | |
| US4847436A (en) | Decomposition of dihydroperoxide to resorcinol | |
| EP0323743B1 (en) | Hydroperoxidation of diisopropylbenzene | |
| US3996111A (en) | Recovering ethylphenol from decomposition products of diethylbenzene monohydroperoxide | |
| US2769844A (en) | Process for preparation of para-alphacumyl phenol | |
| US4302403A (en) | Process for reacting sulfuric acid and an aromatic hydrocarbon to purify a disulfonic acid product of an aromatic hydrocarbon | |
| JP2501603B2 (ja) | α−メチルスチレンの製造法 | |
| US3923909A (en) | Oxidation of diethylbenzenes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |