CA1171377A - Epuration du phenol par consommation reduite d'energie - Google Patents

Epuration du phenol par consommation reduite d'energie

Info

Publication number: CA1171377A
Authority: CA; Canada
Prior art keywords: phenol; organic solvent; phase; impurities; aqueous
Prior art date: 1981-06-08
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.): Expired

Application number

CA000379263A

Other languages

English (en)

Inventor

Jerry R. Cochran

Thomas H. Insinger

Gerald E. Hollenbach

Ronald F. Piskorz

Addison M. Smith

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sunoco Inc R&M

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1981-06-08

Filing date

1981-06-08

Publication date

1984-07-24

1981-06-08 Application filed by Individual filed Critical Individual

1981-06-08 Priority to CA000379263A priority Critical patent/CA1171377A/fr

1984-07-24 Application granted granted Critical

1984-07-24 Publication of CA1171377A publication Critical patent/CA1171377A/fr

Status Expired legal-status Critical Current

Links

ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 156
238000000746 purification Methods 0.000 title abstract description 8
238000005265 energy consumption Methods 0.000 title abstract description 4
239000012535 impurity Substances 0.000 claims abstract description 69
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
239000012071 phase Substances 0.000 claims abstract description 34
239000003960 organic solvent Substances 0.000 claims abstract description 25
239000008346 aqueous phase Substances 0.000 claims abstract description 13
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 12
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 12
238000001256 steam distillation Methods 0.000 claims abstract description 12
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims abstract description 10
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims abstract description 8
238000003776 cleavage reaction Methods 0.000 claims abstract description 7
229920000768 polyamine Polymers 0.000 claims abstract description 7
230000007017 scission Effects 0.000 claims abstract description 7
150000008065 acid anhydrides Chemical class 0.000 claims abstract description 6
239000010410 layer Substances 0.000 claims description 27
238000000605 extraction Methods 0.000 claims description 26
RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 26
238000000034 method Methods 0.000 claims description 26
230000008569 process Effects 0.000 claims description 25
GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 claims description 16
238000010992 reflux Methods 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
239000012044 organic layer Substances 0.000 claims description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 claims 1
239000008096 xylene Substances 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 17
238000002156 mixing Methods 0.000 abstract description 15
239000000126 substance Substances 0.000 abstract description 15
239000002253 acid Substances 0.000 abstract description 7
239000012074 organic phase Substances 0.000 abstract description 7
230000015572 biosynthetic process Effects 0.000 abstract description 3
-1 phthalic anhydride Chemical class 0.000 abstract description 3
239000000047 product Substances 0.000 description 37
238000004821 distillation Methods 0.000 description 25
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
238000000926 separation method Methods 0.000 description 14
238000010533 azeotropic distillation Methods 0.000 description 12
239000002904 solvent Substances 0.000 description 11
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 10
239000000463 material Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002585 base Substances 0.000 description 9
239000013505 freshwater Substances 0.000 description 9
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
230000020477 pH reduction Effects 0.000 description 8
238000009835 boiling Methods 0.000 description 6
238000007792 addition Methods 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
239000003086 colorant Substances 0.000 description 3
SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000243 solution Substances 0.000 description 3
238000000638 solvent extraction Methods 0.000 description 3
BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
241001214257 Mene Species 0.000 description 1
241001594894 Mesites Species 0.000 description 1
206010041662 Splinter Diseases 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000000998 batch distillation Methods 0.000 description 1
239000004294 calcium hydrogen sulphite Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001907 coumarones Chemical class 0.000 description 1
NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000001139 pH measurement Methods 0.000 description 1
KSSNXJHPEFVKHY-UHFFFAOYSA-N phenol;hydrate Chemical compound O.OC1=CC=CC=C1 KSSNXJHPEFVKHY-UHFFFAOYSA-N 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
RGYOXKLCSIJDMU-UHFFFAOYSA-M sodium;phenoxide;hydrate Chemical compound [OH-].[Na+].OC1=CC=CC=C1 RGYOXKLCSIJDMU-UHFFFAOYSA-M 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
239000002351 wastewater 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

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000379263A 1981-06-08 1981-06-08 Epuration du phenol par consommation reduite d'energie Expired CA1171377A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000379263A CA1171377A (fr)	1981-06-08	1981-06-08	Epuration du phenol par consommation reduite d'energie

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000379263A CA1171377A (fr)	1981-06-08	1981-06-08	Epuration du phenol par consommation reduite d'energie

Publications (1)

Publication Number	Publication Date
CA1171377A true CA1171377A (fr)	1984-07-24

Family

ID=4120175

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000379263A Expired CA1171377A (fr)	1981-06-08	1981-06-08	Epuration du phenol par consommation reduite d'energie

Country Status (1)

Country	Link
CA (1)	CA1171377A (fr)

1981
- 1981-06-08 CA CA000379263A patent/CA1171377A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-07-24	MKEX	Expiry

Publication	Publication Date	Title
US4298765A (en)	1981-11-03	Purification of phenol with reduced energy consumption
US5064507A (en)	1991-11-12	Distillation process for recovery of high purity phenol
CA1167051A (fr)	1984-05-08	Methode pour la recuperation de furfural, d'acide formique, d'acide acetique et d'autres constituants organiques a partir d'hydrolysats acides de substances vegetales renfermant du pentosane
US4474994A (en)	1984-10-02	Purification of vanillin
US4209646A (en)	1980-06-24	Process for crystallizing an adduct of 2,2-di(4-hydroxyphenyl) propane and phenol
US4554054A (en)	1985-11-19	Methacrylic acid separation
US4374283A (en)	1983-02-15	Purification of aqueous effluent streams containing BPA and phenol
US3230156A (en)	1966-01-18	Purification of synthetic methanol by plural stage distillation
US4925565A (en)	1990-05-15	Process for extracting and disposing of nitrophenolic by-products
US4400553A (en)	1983-08-23	Recovery of BPA and phenol from aqueous effluent streams
US4737318A (en)	1988-04-12	Recovery of acetic anhydride
US4634796A (en)	1987-01-06	Production of high purity phenol
JPH0129780B2 (fr)	1989-06-14
EP1948595A1 (fr)	2008-07-30	Processus de recuperation par distillation de produits de decomposition d'hydroperoxyde de cumene
US3335070A (en)	1967-08-08	Phenol purification by base addition and plural distillation
US6844472B1 (en)	2005-01-18	Method and installation for separating and purifying diphenols in the phenol and phenol derivatives industry
US4349418A (en)	1982-09-14	Production of methylnaphthalenes and tar bases including indole
US3337423A (en)	1967-08-22	Process for recovering isophorone
US4851086A (en)	1989-07-25	Production of high purity phenol by steam distillation
US4504364A (en)	1985-03-12	Phenol purification
US4857151A (en)	1989-08-15	Phenol purification
US4208350A (en)	1980-06-17	Separating phenols from alkaline pulping spent liquors
WO1995004582A1 (fr)	1995-02-16	Recuperation de phenol a partir de faibles concentrations de sulfate de sodium
JP4224877B2 (ja)	2009-02-18	精製フェノールの製造方法
US4532012A (en)	1985-07-30	Production of high purity phenol by distillation with steam and a solvent