NO118374B - - Google Patents
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- Publication number
- NO118374B NO118374B NO157303A NO15730365A NO118374B NO 118374 B NO118374 B NO 118374B NO 157303 A NO157303 A NO 157303A NO 15730365 A NO15730365 A NO 15730365A NO 118374 B NO118374 B NO 118374B
- Authority
- NO
- Norway
- Prior art keywords
- chlorination
- temperature
- methylphenoxyacetic acid
- boiling point
- acid
- Prior art date
Links
- 238000005660 chlorination reaction Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 claims description 17
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000003245 coal Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000003350 kerosene Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 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 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000002798 spectrophotometry method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WJQZZLQMLJPKQH-UHFFFAOYSA-N 2,4-dichloro-6-methylphenol Chemical compound CC1=CC(Cl)=CC(Cl)=C1O WJQZZLQMLJPKQH-UHFFFAOYSA-N 0.000 description 2
- SEGKFMXJNIEDQN-UHFFFAOYSA-N 2-(2,4-dichloro-6-methylphenoxy)acetic acid Chemical compound CC1=CC(Cl)=CC(Cl)=C1OCC(O)=O SEGKFMXJNIEDQN-UHFFFAOYSA-N 0.000 description 2
- WHLKFTSLSDHFMU-UHFFFAOYSA-N 2-(2-chloro-6-methylphenoxy)acetic acid Chemical compound CC1=CC=CC(Cl)=C1OCC(O)=O WHLKFTSLSDHFMU-UHFFFAOYSA-N 0.000 description 2
- YPNZJHFXFVLXSE-UHFFFAOYSA-N 2-chloro-6-methylphenol Chemical compound CC1=CC=CC(Cl)=C1O YPNZJHFXFVLXSE-UHFFFAOYSA-N 0.000 description 2
- WADQOGCINABPRT-UHFFFAOYSA-N 3-chloro-2-methylphenol Chemical compound CC1=C(O)C=CC=C1Cl WADQOGCINABPRT-UHFFFAOYSA-N 0.000 description 2
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940079920 digestives acid preparations Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
- C07D455/08—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems having an isoquinolyl-1, a substituted isoquinolyl-1 or an alkylenedioxyisoquinolyl-1 radical linked through only one carbon atom, attached in position 2, e.g. emetine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11809/64A GB1092287A (en) | 1964-03-20 | 1964-03-20 | Preparation of benzoquinolizinyl acetic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO118374B true NO118374B (xx) | 1969-12-22 |
Family
ID=9993091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO157303A NO118374B (xx) | 1964-03-20 | 1965-03-19 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3326922A (xx) |
| AT (1) | AT256842B (xx) |
| BE (1) | BE661295A (xx) |
| BR (1) | BR6567999D0 (xx) |
| CH (1) | CH525210A (xx) |
| CS (1) | CS167216B2 (xx) |
| DE (1) | DE1620705C3 (xx) |
| DK (1) | DK120343B (xx) |
| ES (1) | ES310666A1 (xx) |
| GB (1) | GB1092287A (xx) |
| IL (1) | IL23161A (xx) |
| LU (1) | LU48227A1 (xx) |
| MC (1) | MC520A1 (xx) |
| NL (1) | NL6503498A (xx) |
| NO (1) | NO118374B (xx) |
| SE (1) | SE326449B (xx) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3045020A (en) * | 1962-07-17 | x xcooa | ||
| US2877226A (en) * | 1959-03-10 | Novel quinolizine compounds and proc- |
-
1964
- 1964-03-20 GB GB11809/64A patent/GB1092287A/en not_active Expired
-
1965
- 1965-03-12 DE DE1620705A patent/DE1620705C3/de not_active Expired
- 1965-03-15 IL IL23161A patent/IL23161A/en unknown
- 1965-03-17 US US440609A patent/US3326922A/en not_active Expired - Lifetime
- 1965-03-17 ES ES0310666A patent/ES310666A1/es not_active Expired
- 1965-03-18 BE BE661295A patent/BE661295A/xx unknown
- 1965-03-19 CS CS1818A patent/CS167216B2/cs unknown
- 1965-03-19 CH CH385465A patent/CH525210A/de not_active IP Right Cessation
- 1965-03-19 MC MC549A patent/MC520A1/xx unknown
- 1965-03-19 DK DK142865AA patent/DK120343B/da unknown
- 1965-03-19 NO NO157303A patent/NO118374B/no unknown
- 1965-03-19 AT AT253065A patent/AT256842B/de active
- 1965-03-19 NL NL6503498A patent/NL6503498A/xx unknown
- 1965-03-20 LU LU48227D patent/LU48227A1/xx unknown
- 1965-03-20 SE SE03624/65A patent/SE326449B/xx unknown
- 1965-03-22 BR BR167999/65A patent/BR6567999D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1092287A (en) | 1967-11-22 |
| SE326449B (xx) | 1970-07-27 |
| DE1620705B2 (de) | 1974-06-06 |
| DE1620705C3 (de) | 1975-10-16 |
| AT256842B (de) | 1967-09-11 |
| NL6503498A (xx) | 1965-09-21 |
| CS167216B2 (xx) | 1976-04-29 |
| LU48227A1 (xx) | 1965-09-20 |
| CH525210A (de) | 1972-07-15 |
| US3326922A (en) | 1967-06-20 |
| DK120343B (da) | 1971-05-17 |
| DE1620705A1 (de) | 1970-06-04 |
| IL23161A (en) | 1969-02-27 |
| MC520A1 (fr) | 1965-10-26 |
| ES310666A1 (es) | 1965-09-01 |
| BE661295A (xx) | 1965-09-20 |
| BR6567999D0 (pt) | 1973-08-07 |
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