NO822134L - Fremgangsmaate for fremstilling av ortohydroksybensylalkoholer - Google Patents
Fremgangsmaate for fremstilling av ortohydroksybensylalkoholerInfo
- Publication number
- NO822134L NO822134L NO822134A NO822134A NO822134L NO 822134 L NO822134 L NO 822134L NO 822134 A NO822134 A NO 822134A NO 822134 A NO822134 A NO 822134A NO 822134 L NO822134 L NO 822134L
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- phenol
- catalyst
- formaldehyde
- aluminum
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- -1 HYDROXYBENZYL ALCOHOLS Chemical class 0.000 title claims abstract description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 230000003197 catalytic effect Effects 0.000 claims abstract description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 63
- 229910052782 aluminium Inorganic materials 0.000 claims description 23
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 18
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 238000004817 gas chromatography Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004811 liquid chromatography Methods 0.000 claims description 2
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 12
- 229920002866 paraformaldehyde Polymers 0.000 description 12
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000006482 condensation reaction Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 150000001638 boron Chemical class 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene 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
- C07C37/11—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
- C07C37/115—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 using acetals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8112470A FR2508440B1 (fr) | 1981-06-25 | 1981-06-25 | Procede de preparation d'alcools orthohydroxybenzyliques |
Publications (1)
Publication Number | Publication Date |
---|---|
NO822134L true NO822134L (no) | 1982-12-27 |
Family
ID=9259860
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO822134A NO822134L (no) | 1981-06-25 | 1982-06-24 | Fremgangsmaate for fremstilling av ortohydroksybensylalkoholer |
Country Status (10)
Country | Link |
---|---|
US (1) | US4460799A (de) |
EP (1) | EP0069016B1 (de) |
JP (1) | JPS5849327A (de) |
AT (1) | ATE15644T1 (de) |
CA (1) | CA1200254A (de) |
DE (1) | DE3266376D1 (de) |
DK (1) | DK284382A (de) |
ES (1) | ES513416A0 (de) |
FR (1) | FR2508440B1 (de) |
NO (1) | NO822134L (de) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK335086A (da) * | 1985-08-05 | 1987-02-06 | Michele Testa | Kemiske sammensaetninger og farmaceutiske praeparater til topisk brug indeholdende mindst en af de kemiske sammensaetninger i en terapeutiskvirksom maengde |
US5242914A (en) * | 1988-04-01 | 1993-09-07 | Sankyo Company, Limited | 2-(heterocyclylthio) carbapenem derivatives, their preparation and their use as antibiotics |
ES2067534T3 (es) * | 1988-04-01 | 1995-04-01 | Sankyo Co | Derivados de 2-(heterocicliltio)carbapenemo, su preparacion y su aplicacion como antibioticos. |
EP0485613B1 (de) * | 1990-05-25 | 1995-12-06 | Mitsubishi Chemical Corporation | Verfahren zur para-methylolierung einer phenolischen verbindung |
US5603929A (en) * | 1994-11-16 | 1997-02-18 | Alcon Laboratories, Inc. | Preserved ophthalmic drug compositions containing polymeric quaternary ammonium compounds |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB751845A (en) * | 1951-12-20 | 1956-07-04 | Howards Ilford Ltd | Manufacture of saligenin |
US2858342A (en) * | 1955-06-27 | 1958-10-28 | Union Carbide Corp | Preparation of bis-phenols |
US2909568A (en) * | 1957-09-05 | 1959-10-20 | Universal Oil Prod Co | Methylation of hydroxyaromatic compounds |
FR1270731A (fr) * | 1960-07-28 | 1961-09-01 | Shell Int Research | Procédé de préparation de composés phénoliques alcoylés |
FR1328945A (fr) * | 1962-03-28 | 1963-06-07 | Rhone Poulenc Sa | Procédé de préparation des alcools orthohydroxybenzyliques |
US3485797A (en) * | 1966-03-14 | 1969-12-23 | Ashland Oil Inc | Phenolic resins containing benzylic ether linkages and unsubstituted para positions |
FR2372182A1 (fr) * | 1976-11-29 | 1978-06-23 | Mo Khim T | Procede de preparation d'oligomeres phenol-formol de configuration reguliere ortho |
DE2729075A1 (de) * | 1977-06-28 | 1979-01-18 | Haarmann & Reimer Gmbh | Verfahren zur herstellung von reinem 2-hydroxybenzylalkohol, reinem 4-hydroxybenzylalkohol oder einem gemisch beider hydroxybenzylalkohole |
DE2915216A1 (de) * | 1979-04-14 | 1980-10-23 | Haarmann & Reimer Gmbh | Verfahren zur herstellung eines gemisches aus 2- und 4-hydroxybenzylalkohol |
-
1981
- 1981-06-25 FR FR8112470A patent/FR2508440B1/fr not_active Expired
-
1982
- 1982-06-23 CA CA000405828A patent/CA1200254A/fr not_active Expired
- 1982-06-23 ES ES513416A patent/ES513416A0/es active Granted
- 1982-06-23 US US06/391,467 patent/US4460799A/en not_active Expired - Fee Related
- 1982-06-24 DK DK284382A patent/DK284382A/da not_active Application Discontinuation
- 1982-06-24 NO NO822134A patent/NO822134L/no unknown
- 1982-06-25 AT AT82401173T patent/ATE15644T1/de not_active IP Right Cessation
- 1982-06-25 DE DE8282401173T patent/DE3266376D1/de not_active Expired
- 1982-06-25 JP JP57108641A patent/JPS5849327A/ja active Pending
- 1982-06-25 EP EP82401173A patent/EP0069016B1/de not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ES8304054A1 (es) | 1983-03-16 |
JPS5849327A (ja) | 1983-03-23 |
ATE15644T1 (de) | 1985-10-15 |
EP0069016B1 (de) | 1985-09-18 |
ES513416A0 (es) | 1983-03-16 |
DE3266376D1 (en) | 1985-10-24 |
FR2508440A1 (fr) | 1982-12-31 |
CA1200254A (fr) | 1986-02-04 |
US4460799A (en) | 1984-07-17 |
DK284382A (da) | 1982-12-26 |
EP0069016A1 (de) | 1983-01-05 |
FR2508440B1 (fr) | 1985-11-08 |
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