BE606401A - - Google Patents
Info
- Publication number
- BE606401A BE606401A BE606401DA BE606401A BE 606401 A BE606401 A BE 606401A BE 606401D A BE606401D A BE 606401DA BE 606401 A BE606401 A BE 606401A
- Authority
- BE
- Belgium
- Prior art keywords
- phenols
- water
- extractant
- distillation
- column
- Prior art date
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 171
- 150000002989 phenols Chemical class 0.000 claims description 114
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 62
- 238000000605 extraction Methods 0.000 claims description 52
- 238000004821 distillation Methods 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 51
- 238000005406 washing Methods 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 23
- 238000009835 boiling Methods 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 238000003786 synthesis reaction Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 239000003643 water by type Substances 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 12
- 150000001241 acetals Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 230000001264 neutralization Effects 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 238000010504 bond cleavage reaction Methods 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 230000002378 acidificating Effects 0.000 claims description 2
- 238000005882 aldol condensation reaction Methods 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- 239000000571 coke Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 230000001747 exhibiting Effects 0.000 claims description 2
- 239000008262 pumice Substances 0.000 claims description 2
- 230000000717 retained Effects 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 241000132092 Aster Species 0.000 claims 1
- 239000003518 caustics Substances 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 36
- 239000000727 fraction Substances 0.000 description 32
- 239000003921 oil Substances 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- -1 aliphatic alcohols Chemical class 0.000 description 7
- 238000009434 installation Methods 0.000 description 7
- 238000004939 coking Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000002641 tar oil Substances 0.000 description 4
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 3
- 239000012223 aqueous fraction Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000011269 tar Substances 0.000 description 3
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-Hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-Dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- KSOWMDCLEHRQPH-UHFFFAOYSA-N 4-diazocyclohexa-1,5-dien-1-amine Chemical compound NC1=CCC(=[N+]=[N-])C=C1 KSOWMDCLEHRQPH-UHFFFAOYSA-N 0.000 description 1
- JRPPVSMCCSLJPL-UHFFFAOYSA-N 7-methyloctanal Chemical class CC(C)CCCCCC=O JRPPVSMCCSLJPL-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 210000000709 Aorta Anatomy 0.000 description 1
- 241000282322 Panthera Species 0.000 description 1
- 101710022641 SLC26A6 Proteins 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 235000019577 caloric intake Nutrition 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE606401A true BE606401A (de) |
Family
ID=192870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE606401D BE606401A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE606401A (de) |
-
0
- BE BE606401D patent/BE606401A/fr unknown
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