JPS6021134B2 - Ｏ−ジアルキルアミノメチルフエノ−ル類の製造法 - Google Patents
Ｏ−ジアルキルアミノメチルフエノ−ル類の製造法Info
- Publication number
- JPS6021134B2 JPS6021134B2 JP52004477A JP447777A JPS6021134B2 JP S6021134 B2 JPS6021134 B2 JP S6021134B2 JP 52004477 A JP52004477 A JP 52004477A JP 447777 A JP447777 A JP 447777A JP S6021134 B2 JPS6021134 B2 JP S6021134B2
- Authority
- JP
- Japan
- Prior art keywords
- dialkylaminomethylphenols
- phenol
- reaction
- solvent
- formula
- Prior art date
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 6
- 229920002866 paraformaldehyde Polymers 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001983 dialkylethers Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- -1 methylbutyl Chemical group 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- NFVPEIKDMMISQO-UHFFFAOYSA-N 4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C=C1 NFVPEIKDMMISQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- HKGAHGXQFHBAOP-UHFFFAOYSA-N 2,3-bis(aminomethyl)phenol Chemical compound NCC1=CC=CC(O)=C1CN HKGAHGXQFHBAOP-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- VUENIEFVRKDJAS-UHFFFAOYSA-N 2,6-bis[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=CC(CN(C)C)=C1O VUENIEFVRKDJAS-UHFFFAOYSA-N 0.000 description 1
- IGXXOUGMPVOZFH-UHFFFAOYSA-N 2-(diethylaminomethyl)phenol Chemical compound CCN(CC)CC1=CC=CC=C1O IGXXOUGMPVOZFH-UHFFFAOYSA-N 0.000 description 1
- AUABZJZJXPSZCN-UHFFFAOYSA-N 2-(dimethylamino)phenol Chemical group CN(C)C1=CC=CC=C1O AUABZJZJXPSZCN-UHFFFAOYSA-N 0.000 description 1
- XYXBMCIMPXOBLB-UHFFFAOYSA-N 3,4,5-tris(dimethylamino)-2-methylphenol Chemical compound CN(C)C1=CC(O)=C(C)C(N(C)C)=C1N(C)C XYXBMCIMPXOBLB-UHFFFAOYSA-N 0.000 description 1
- AMKMYXVFAOJGGQ-UHFFFAOYSA-N 4-(methylaminomethyl)phenol Chemical compound CNCC1=CC=C(O)C=C1 AMKMYXVFAOJGGQ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 101000973623 Homo sapiens Neuronal growth regulator 1 Proteins 0.000 description 1
- 102100022223 Neuronal growth regulator 1 Human genes 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000007281 aminoalkylation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 238000005191 phase separation Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2601782A DE2601782C3 (de) | 1976-01-20 | 1976-01-20 | Verfahren zur Herstellung von o-Dialkylaminomethylphenolen |
| DE2601782.3 | 1976-01-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5289631A JPS5289631A (en) | 1977-07-27 |
| JPS6021134B2 true JPS6021134B2 (ja) | 1985-05-25 |
Family
ID=5967723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52004477A Expired JPS6021134B2 (ja) | 1976-01-20 | 1977-01-20 | Ｏ−ジアルキルアミノメチルフエノ−ル類の製造法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4212822A (en, 2012) |
| JP (1) | JPS6021134B2 (en, 2012) |
| AT (1) | AT345786B (en, 2012) |
| BE (1) | BE850525A (en, 2012) |
| BR (1) | BR7700286A (en, 2012) |
| CH (1) | CH626046A5 (en, 2012) |
| DE (1) | DE2601782C3 (en, 2012) |
| DK (1) | DK153140C (en, 2012) |
| FR (1) | FR2338924A1 (en, 2012) |
| GB (1) | GB1514694A (en, 2012) |
| IL (1) | IL51271A (en, 2012) |
| IT (1) | IT1076104B (en, 2012) |
| NL (1) | NL7700445A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4215229A (en) * | 1978-06-15 | 1980-07-29 | Koppers Company, Inc. | Process for alkylating phenolic compounds to produce ortho- and para-monoalkylated phenols and 2,4- and 2,6-dialkylated phenols |
| US4310592A (en) * | 1980-10-29 | 1982-01-12 | Akzona Incorporated | N-(2-Hydroxybenzyl)alkylamines as water-repellant agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3155704A (en) * | 1960-09-01 | 1964-11-03 | Ethyl Corp | O, o-dialkyl 3, 5-dialkyl 4-hydroxyphenylalkyl phosphonates and process for preparing same |
| US3969409A (en) * | 1972-05-11 | 1976-07-13 | Takeda Chemical Industries, Ltd. | 3-Anilino-5,5-disubstituted-2-aminomethyl-2-cyclohexen-1-ones and the salts thereof |
| DE2456935A1 (de) * | 1973-12-10 | 1975-06-12 | Ciba Geigy Ag | Trialkylsubstituierte hydroxybenzylmalonate und damit stabilisierte mischungen |
-
1976
- 1976-01-20 DE DE2601782A patent/DE2601782C3/de not_active Expired
- 1976-12-30 US US05/755,905 patent/US4212822A/en not_active Expired - Lifetime
-
1977
- 1977-01-17 BR BR7700286A patent/BR7700286A/pt unknown
- 1977-01-17 GB GB1686/77A patent/GB1514694A/en not_active Expired
- 1977-01-17 NL NL7700445A patent/NL7700445A/xx not_active Application Discontinuation
- 1977-01-17 CH CH55177A patent/CH626046A5/de not_active IP Right Cessation
- 1977-01-17 IL IL51271A patent/IL51271A/xx unknown
- 1977-01-18 IT IT19410/77A patent/IT1076104B/it active
- 1977-01-18 AT AT25177A patent/AT345786B/de not_active IP Right Cessation
- 1977-01-19 BE BE174197A patent/BE850525A/xx not_active IP Right Cessation
- 1977-01-19 DK DK019977A patent/DK153140C/da not_active IP Right Cessation
- 1977-01-20 FR FR7701569A patent/FR2338924A1/fr active Granted
- 1977-01-20 JP JP52004477A patent/JPS6021134B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR7700286A (pt) | 1977-09-20 |
| AT345786B (de) | 1978-10-10 |
| DE2601782A1 (de) | 1977-07-21 |
| DE2601782B2 (de) | 1978-11-30 |
| FR2338924B1 (en, 2012) | 1983-09-09 |
| ATA25177A (de) | 1978-02-15 |
| US4212822A (en) | 1980-07-15 |
| DK153140C (da) | 1988-10-31 |
| DK19977A (da) | 1977-07-21 |
| GB1514694A (en) | 1978-06-21 |
| IL51271A0 (en) | 1977-03-31 |
| JPS5289631A (en) | 1977-07-27 |
| BE850525A (fr) | 1977-07-19 |
| IT1076104B (it) | 1985-04-24 |
| DE2601782C3 (de) | 1979-08-02 |
| NL7700445A (nl) | 1977-07-22 |
| FR2338924A1 (fr) | 1977-08-19 |
| DK153140B (da) | 1988-06-20 |
| CH626046A5 (en, 2012) | 1981-10-30 |
| IL51271A (en) | 1979-10-31 |
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