FR2436124A1 - Procede pour la preparation de la phloroglucine a partir d'hexachlorobenzene - Google Patents
Procede pour la preparation de la phloroglucine a partir d'hexachlorobenzeneInfo
- Publication number
- FR2436124A1 FR2436124A1 FR7922996A FR7922996A FR2436124A1 FR 2436124 A1 FR2436124 A1 FR 2436124A1 FR 7922996 A FR7922996 A FR 7922996A FR 7922996 A FR7922996 A FR 7922996A FR 2436124 A1 FR2436124 A1 FR 2436124A1
- Authority
- FR
- France
- Prior art keywords
- hexachlorobenzene
- phloroglucin
- sodium
- preparation
- ether
- 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.)
- Withdrawn
Links
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 title abstract 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 title abstract 2
- 229960001553 phloroglucinol Drugs 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/24—Preparation of ethers by reactions not forming ether-oxygen bonds by elimination of halogens, e.g. elimination of HCl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Ce procédé est caractérisé par le fait qu'on transforme l'hexachlorobenzène à des températures allant de 50 à 250 degrés C, avec une quantité 3 à 20 fois molaire de propylate de sodium, ou d'isoropylate de sodium, dans un solvant aprotique, en trichlorophloroglucinetripropyléther, ou en trichlorophloroglucinetriisopropyléther, qu'on élimine le chlore de cet éther à l'aide du sodium métallique pour avoir le phlorogiucinetripropyléther, ou le phloroglucinetriisopropyléther, et qu'on hydrolyse ce nouvel éther d'une façon connue en phloroglucine. Ce procédé permet d'utiliser l'hexachlorobenzène qui à cause de sa toxicité constitue un sous-produit de certaines fabrications difficile à employer.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19782840597 DE2840597A1 (de) | 1978-09-18 | 1978-09-18 | Verfahren zur herstellung von phloroglucin |
Publications (1)
Publication Number | Publication Date |
---|---|
FR2436124A1 true FR2436124A1 (fr) | 1980-04-11 |
Family
ID=6049766
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7922996A Withdrawn FR2436124A1 (fr) | 1978-09-18 | 1979-09-14 | Procede pour la preparation de la phloroglucine a partir d'hexachlorobenzene |
Country Status (5)
Country | Link |
---|---|
US (1) | US4296260A (fr) |
JP (1) | JPS5540697A (fr) |
CA (1) | CA1154461A (fr) |
DE (1) | DE2840597A1 (fr) |
FR (1) | FR2436124A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2436125A1 (fr) * | 1978-09-18 | 1980-04-11 | Akzo Nv | Trichlorophloroglucinetripropylether, trichlorophloroglucinetriisopropylether, leur preparation et leur hydrolyse en trichlorophloroglucine |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3332955A1 (de) * | 1983-09-13 | 1985-03-28 | Merck Patent Gmbh, 6100 Darmstadt | Carbocyclische sechsringverbindungen |
ES2069461B1 (es) * | 1993-02-08 | 1996-02-16 | Marquinez Joxe I Aki Alava | Procedimiento para la determinacion y cuantificacion de ligninas. |
FR2840608B1 (fr) | 2002-06-11 | 2005-07-01 | Seranalis | Procede de preparation de 1,3,5-triaminobenzene et son hydrolyse en phloroglucinol de haute purete |
DE102009019902A1 (de) * | 2009-05-05 | 2010-11-11 | Merck Patent Gmbh | Mittel und Verfahren zur Bestimmung des Aldehyd-Gehalts |
CN103012069B (zh) * | 2012-12-30 | 2014-01-15 | 湖南尔康制药股份有限公司 | 一种药用级间苯三酚的生产工艺 |
PL3191438T3 (pl) | 2014-09-11 | 2022-02-14 | Pepsico, Inc. | Wzmacniacz słodkości |
RU2595782C1 (ru) * | 2015-07-07 | 2016-08-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Чувашский государственный университет имени И.Н. Ульянова" | Способ определения электрических параметров, характеризующих состояние подэлектродных пространств ванны трехфазной трехэлектродной руднотермической печи с расположением электродов в линию |
CN105622302B (zh) * | 2016-01-14 | 2017-08-01 | 常州大学 | 一种取代连苯三酚的合成方法 |
CN115260010B (zh) * | 2021-04-29 | 2023-11-24 | 新岸诺亚(北京)催化科技有限公司 | 一种由2,6-二氟苯腈制备间氟苯酚的方法 |
CN115925520A (zh) * | 2022-11-03 | 2023-04-07 | 江苏联环药业股份有限公司 | 一种间苯三酚的合成方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2174900A1 (fr) * | 1972-03-03 | 1973-10-19 | Dynamit Nobel Ag | |
GB1431501A (en) * | 1973-12-11 | 1976-04-07 | Oce Andeno Bv | Preparation of phloroglucinol and ethers thereof |
FR2436125A1 (fr) * | 1978-09-18 | 1980-04-11 | Akzo Nv | Trichlorophloroglucinetripropylether, trichlorophloroglucinetriisopropylether, leur preparation et leur hydrolyse en trichlorophloroglucine |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD24998A (fr) * | ||||
DE102358C (fr) * | ||||
US2461498A (en) * | 1943-12-08 | 1949-02-08 | Edwal Lab Inc | Preparation of symmetrical triaminobenzene compounds |
DE813709C (de) * | 1945-03-28 | 1951-09-17 | Ici Ltd | Verfahren zur Herstellung von aromatischen monocyclischen Triaminokohlenwasserstoffen |
US2799698A (en) * | 1954-12-30 | 1957-07-16 | Hercules Powder Co Ltd | Oxidation of alkyl-substituted aromatic compounds to phenolic compounds |
US3028410A (en) * | 1958-06-26 | 1962-04-03 | Hooker Chemical Corp | Synthesis of polyhydroxy aromatic compounds |
GB1012782A (en) * | 1960-12-07 | 1965-12-08 | Hoechst Ag | Process for the manufacture of phloroglucinol |
US3230266A (en) * | 1961-11-17 | 1966-01-18 | Morton Int Inc | Preparation of phloroglucinol |
DE1195327B (de) * | 1963-03-22 | 1965-06-24 | Kalle Ag | Verfahren zur Herstellung von symmetrischen Trihydroxybenzolen |
GB1022733A (en) * | 1964-05-19 | 1966-03-16 | Whiffen & Sons Ltd | Triaminobenzene |
GB1106088A (en) * | 1964-09-10 | 1968-03-13 | Fisons Ind Chemicals Ltd | Process for the preparation of phloroglucinol |
GB1274551A (en) * | 1969-02-18 | 1972-05-17 | Fisons Ind Chemicals Ltd | Improvements in a process for the production of triaminobenzene |
GB1388840A (en) * | 1971-06-24 | 1975-03-26 | Oce Andeno Bv | Preparation of phloroglucinol and its monomethyl ether |
US3959388A (en) * | 1972-06-23 | 1976-05-25 | Andeno B.V. | Preparation of phloroglucinol or its monomethyl ether |
GB1451317A (en) * | 1972-12-18 | 1976-09-29 | Oce Andeno Bv | Preparation of phloroglucinol or its monomethyl ether |
US3959399A (en) * | 1975-02-19 | 1976-05-25 | Nalco Chemical Company | Mono-alkylation of naphthalene |
DE2621431C3 (de) * | 1976-05-14 | 1980-05-29 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von Phloroglucin |
US4093667A (en) * | 1977-03-14 | 1978-06-06 | Continental Oil Company | Preparation of 4-n-hexylresorcinol |
-
1978
- 1978-09-18 DE DE19782840597 patent/DE2840597A1/de not_active Withdrawn
-
1979
- 1979-08-08 US US06/064,691 patent/US4296260A/en not_active Expired - Lifetime
- 1979-09-14 FR FR7922996A patent/FR2436124A1/fr not_active Withdrawn
- 1979-09-17 CA CA000335801A patent/CA1154461A/fr not_active Expired
- 1979-09-18 JP JP11887579A patent/JPS5540697A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2174900A1 (fr) * | 1972-03-03 | 1973-10-19 | Dynamit Nobel Ag | |
GB1431501A (en) * | 1973-12-11 | 1976-04-07 | Oce Andeno Bv | Preparation of phloroglucinol and ethers thereof |
FR2436125A1 (fr) * | 1978-09-18 | 1980-04-11 | Akzo Nv | Trichlorophloroglucinetripropylether, trichlorophloroglucinetriisopropylether, leur preparation et leur hydrolyse en trichlorophloroglucine |
Non-Patent Citations (1)
Title |
---|
HW1960 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2436125A1 (fr) * | 1978-09-18 | 1980-04-11 | Akzo Nv | Trichlorophloroglucinetripropylether, trichlorophloroglucinetriisopropylether, leur preparation et leur hydrolyse en trichlorophloroglucine |
Also Published As
Publication number | Publication date |
---|---|
US4296260A (en) | 1981-10-20 |
JPS5540697A (en) | 1980-03-22 |
CA1154461A (fr) | 1983-09-27 |
DE2840597A1 (de) | 1980-03-27 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |