DD143598A5 - Verfahren zur erniedrigung des 2,6-dialkylphenolgehaltes einer alkylphenolmischung - Google Patents
Verfahren zur erniedrigung des 2,6-dialkylphenolgehaltes einer alkylphenolmischung Download PDFInfo
- Publication number
- DD143598A5 DD143598A5 DD78211794A DD21179478A DD143598A5 DD 143598 A5 DD143598 A5 DD 143598A5 DD 78211794 A DD78211794 A DD 78211794A DD 21179478 A DD21179478 A DD 21179478A DD 143598 A5 DD143598 A5 DD 143598A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkylphenol
- mixture
- phenol
- reaction
- hours
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000008569 process Effects 0.000 title claims abstract description 18
- 238000010992 reflux Methods 0.000 claims abstract description 14
- 239000003377 acid catalyst Substances 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 21
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000011541 reaction mixture Substances 0.000 abstract description 6
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract description 4
- XGMDYIYCKWMWLY-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonic acid Chemical compound OS(=O)(=O)CC(F)(F)F XGMDYIYCKWMWLY-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 33
- 238000006317 isomerization reaction Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 150000001336 alkenes Chemical class 0.000 description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 8
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical class CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- -1 alkyl phenols Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- YYOQJBLGFMMRLJ-UHFFFAOYSA-N 3,5-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC(O)=CC(C(C)C)=C1 YYOQJBLGFMMRLJ-UHFFFAOYSA-N 0.000 description 2
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- LYCAGOQDEOWYGS-UHFFFAOYSA-N 1,2,2-trifluoroethenesulfonic acid Chemical compound OS(=O)(=O)C(F)=C(F)F LYCAGOQDEOWYGS-UHFFFAOYSA-N 0.000 description 1
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- MFFHOTWDYMNSLG-UHFFFAOYSA-N 2,3,4-tri(propan-2-yl)phenol Chemical compound CC(C)C1=CC=C(O)C(C(C)C)=C1C(C)C MFFHOTWDYMNSLG-UHFFFAOYSA-N 0.000 description 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 1
- FTOPRAYFWQEJPL-UHFFFAOYSA-N 2,6-di(propan-2-yl)phenol;phenol Chemical compound OC1=CC=CC=C1.CC(C)C1=CC=CC(C(C)C)=C1O FTOPRAYFWQEJPL-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- CDTSKWPVNCJNNT-UHFFFAOYSA-N phenol;2-propan-2-ylphenol Chemical compound OC1=CC=CC=C1.CC(C)C1=CC=CC=C1O CDTSKWPVNCJNNT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- 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
-
- 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
- C07C37/14—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 by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (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 |
|---|---|---|---|
| US84162577A | 1977-10-13 | 1977-10-13 | |
| US05/841,626 US4103096A (en) | 1977-10-13 | 1977-10-13 | Preparation of meta-alkylphenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD143598A5 true DD143598A5 (de) | 1980-09-03 |
Family
ID=27126276
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78211794A DD143598A5 (de) | 1977-10-13 | 1978-10-13 | Verfahren zur erniedrigung des 2,6-dialkylphenolgehaltes einer alkylphenolmischung |
| DD78208441A DD139252A5 (de) | 1977-10-13 | 1978-10-13 | Verfahren zur herstellung von alkylphenolen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78208441A DD139252A5 (de) | 1977-10-13 | 1978-10-13 | Verfahren zur herstellung von alkylphenolen |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0001698B1 (fr) |
| JP (1) | JPS5461131A (fr) |
| CA (1) | CA1113504A (fr) |
| DD (2) | DD143598A5 (fr) |
| DE (1) | DE2861212D1 (fr) |
| IL (1) | IL55707A (fr) |
| MX (1) | MX5126E (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4339614A (en) * | 1980-03-14 | 1982-07-13 | Pcuk Produits Chimiques Ugine Kuhlmann | Superacid catalyzed preparation of resorcinol from meta-isopropylphenol |
| JPS61152635A (ja) * | 1984-12-27 | 1986-07-11 | Mitsui Petrochem Ind Ltd | ３，５−ジイソプロピルフエノ−ルの製造方法 |
| GB9722719D0 (en) | 1997-10-29 | 1997-12-24 | Fmc Corp Uk Ltd | Production of phosphate esters |
| JP4643842B2 (ja) | 2000-09-21 | 2011-03-02 | 興和株式会社 | ３，５−ビスアルキルフェノールの製造法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL33439A (en) * | 1968-12-04 | 1973-01-30 | Hodogaya Chemical Co Ltd | Process for recovering m-alkylphenol from a mixture of alkylphenols |
| BE758526A (fr) * | 1969-11-10 | 1971-04-16 | Union Rheinische Braunkohlen | Procede d'isomerisation de 2,6-dimethylphenol |
| JPS5233620B2 (fr) * | 1972-01-10 | 1977-08-30 |
-
1978
- 1978-10-05 JP JP12311778A patent/JPS5461131A/ja active Pending
- 1978-10-10 DE DE7878300480T patent/DE2861212D1/de not_active Expired
- 1978-10-10 EP EP78300480A patent/EP0001698B1/fr not_active Expired
- 1978-10-10 IL IL55707A patent/IL55707A/xx unknown
- 1978-10-12 CA CA313,206A patent/CA1113504A/fr not_active Expired
- 1978-10-13 DD DD78211794A patent/DD143598A5/de unknown
- 1978-10-13 DD DD78208441A patent/DD139252A5/xx unknown
- 1978-10-13 MX MX787466U patent/MX5126E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL55707A0 (en) | 1978-12-17 |
| JPS5461131A (en) | 1979-05-17 |
| MX5126E (es) | 1983-03-24 |
| CA1113504A (fr) | 1981-12-01 |
| EP0001698B1 (fr) | 1981-10-21 |
| DD139252A5 (de) | 1979-12-19 |
| EP0001698A1 (fr) | 1979-05-02 |
| DE2861212D1 (en) | 1981-12-24 |
| IL55707A (en) | 1983-02-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD147664A5 (de) | Verfahren zur gleichzeitigen herstellung von reinem methyl-tert.-butylether | |
| EP0000165B1 (fr) | Procédé de préparation d'alcool 2-hydroxybenzylique pur et d'alcool 4-hydrobenzylique pur, ou d'un mélange de ces deux alcools | |
| DE4127230B4 (de) | Verfahren zur halbkontinuierlichen Herstellung von symmetrischen Dialkylethern | |
| DE3102304C2 (de) | Verfahren zur selektiven Herstellung von β-Isopropylnaphthalin | |
| DE1957167C3 (de) | Verfahren zur Herstellung von Carbonsäuren durch Umsetzung von Olefinen mit Kohlenmonoxid und Wasser in Gegenwart eines Katalysators, der aus Orthophosphorsäure, Bortrifluorid und Wasser erhältlich ist | |
| DD143598A5 (de) | Verfahren zur erniedrigung des 2,6-dialkylphenolgehaltes einer alkylphenolmischung | |
| DE2400260C3 (de) | Verfahren zur Abtrennung von Methacrolein aus einer Gasreaktionsmischung | |
| DE3152701C2 (de) | Verfahren zur Herstellung von im wesentlichen reinem m-Isopropylphenol | |
| DE69218185T2 (de) | Selektive hydroxylierung von phenol oder phenolischen äthern | |
| DE68906202T2 (de) | Verfahren zur Herstellung von Arylethylphenolen mit einem (oder mehreren) Alkyl-Substituenten in der Ethylgruppe und deren Verwendung. | |
| DE2937831C2 (fr) | ||
| DE2102476B2 (de) | Verfahren zur reinigung von o-hydroxydiphenyl | |
| EP0127087B1 (fr) | Procédé de séparation d'un mélange d'hydrocarbures en C4 contenant essentiellement des n-butènes et des butanes | |
| DE19782298B4 (de) | Kontinuierliches Verfahren zur Herstellung von Carbonsäureestern von Alkylenglycolmonoalkylethern | |
| DE2340218C2 (de) | Verfahren zur Gewinnung von 5-Isopropyl-m-kresol aus einem Gemisch von Isopropylkresolen | |
| DE2043689A1 (de) | Verfahren zum Entwässern von Essigsaure | |
| DE2005375C3 (de) | Verfahren zur Herstellung von Mercaptocarbonsäureestern | |
| DE2405283A1 (de) | Thermolyse von styroloxid | |
| CH631954A5 (de) | Verfahren zur herstellung von 2,6-di-tert.-butylphenol. | |
| DE2034369C (de) | Verfahren zur Herstellung von para-tert-Butylphenol | |
| DE2448231C2 (de) | Verfahren zur Herstellung von Alkylnaphthalinen | |
| DE1242592B (de) | Verfahren zur katalytischen Isomerisation von verzweigtkettigen Mono-Olefinen | |
| DE19547498B4 (de) | Verfahren zur kontinuierlichen Herstellung von Alkadienolen | |
| DE1468639C (de) | Verfahren zur Herstellung von bei Raumtemperatur flüssigen Gemischen von Äthylterphenylen | |
| DE925715C (de) | Verfahren zur Abtrennung von 2, 4-Dimethyl-6-tert.-butylphenol aus Gemischen |