BE522565A - - Google Patents
Info
- Publication number
- BE522565A BE522565A BE522565DA BE522565A BE 522565 A BE522565 A BE 522565A BE 522565D A BE522565D A BE 522565DA BE 522565 A BE522565 A BE 522565A
- Authority
- BE
- Belgium
- Prior art keywords
- resorcinol
- meta
- phenol
- isopropenyl
- process according
- Prior art date
Links
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 171
- 238000004821 distillation Methods 0.000 claims description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 33
- 238000009835 boiling Methods 0.000 claims description 30
- 238000003776 cleavage reaction Methods 0.000 claims description 24
- 238000010438 heat treatment Methods 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-Methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000005712 crystallization Effects 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 3
- VUMCUSHVMYIRMB-UHFFFAOYSA-N 1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 VUMCUSHVMYIRMB-UHFFFAOYSA-N 0.000 claims description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-Chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims description 2
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000859 sublimation Methods 0.000 claims description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-Trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229960001755 resorcinol Drugs 0.000 description 70
- 239000000047 product Substances 0.000 description 42
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
- 238000000354 decomposition reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000003197 catalytic Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000002378 acidificating Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000998 batch distillation Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229910000634 wood's metal Inorganic materials 0.000 description 2
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011269 tar Substances 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
- C07C37/08—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE522565A true BE522565A (ja) |
Family
ID=157794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE522565D BE522565A (ja) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE522565A (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2405231A1 (fr) * | 1977-10-08 | 1979-05-04 | Mitsui Petrochemical Ind | Procede de preparation de la resorcine |
-
0
- BE BE522565D patent/BE522565A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2405231A1 (fr) * | 1977-10-08 | 1979-05-04 | Mitsui Petrochemical Ind | Procede de preparation de la resorcine |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR19990007242A (ko) | 아크릴산의 회수 방법 | |
| JP2018537443A (ja) | アルカンスルホン酸を再処理する方法 | |
| US2736753A (en) | Recovery of phenols | |
| US2506540A (en) | Vanillin purification by distillation | |
| FR2467185A1 (fr) | Procedes de separation et de purification du resorcinol et de l'hydroquinone | |
| US4049723A (en) | Method for separation and recovering hydroquinone | |
| RU2207334C2 (ru) | Способ производства метилметакрилата | |
| JPH0611732B2 (ja) | メタクリル酸メチルの精製法 | |
| US4504364A (en) | Phenol purification | |
| EP2222633B1 (fr) | Procede de preparation d'un sel de l'acide trifluoromethanesulfiniques. | |
| FR2470762A1 (fr) | Procede de traitement d'un residu de production d'acide adipique | |
| BE522565A (ja) | ||
| JPH11302224A (ja) | メタクリル酸メチルの精製法 | |
| EP0478428B1 (fr) | Procédé de préparation d'oxyde borique par hydrolyse du borate de méthyle et sa mise en oeuvre dans l'oxydation d'hydrocarbures saturées en alcools | |
| CH312187A (fr) | Procédé pour la production de résorcine. | |
| FR2810317A1 (fr) | Procede de separation d'un compose de type hydroxybenzonitrile | |
| EP0296990B1 (fr) | Procédé de fabrication de polybutadiène hydroxylé | |
| EP0222673B1 (fr) | Procédé de préparation de sels alcalins de l'acide trifluoroacétique à l'état anhydre et cristallisé | |
| US2785205A (en) | Recovery of phenols | |
| JPH10151301A (ja) | 混合液から晶析により物質を分離乃至精製する方法 | |
| JP2001521918A (ja) | アルキレングリコールモノアルキルエーテルのカルボン酸エステルを製造するための連続法 | |
| JP2001031643A (ja) | 水溶液から強酸を回収するための方法 | |
| CH288171A (fr) | Procédé de préparation du phénol. | |
| JPS60239430A (ja) | ヒドロキシアセトフエノン類の回収方法 | |
| BE678415A (ja) |