GB1106088A - Process for the preparation of phloroglucinol - Google Patents
Process for the preparation of phloroglucinolInfo
- Publication number
- GB1106088A GB1106088A GB3705864A GB3705864A GB1106088A GB 1106088 A GB1106088 A GB 1106088A GB 3705864 A GB3705864 A GB 3705864A GB 3705864 A GB3705864 A GB 3705864A GB 1106088 A GB1106088 A GB 1106088A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- trinitrobenzene
- phloroglucinol
- catalyst
- platinum
- 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
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-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 3
- 229960001553 phloroglucinol Drugs 0.000 title abstract 3
- 239000003054 catalyst Substances 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- KAQBNBSMMVTKRN-UHFFFAOYSA-N 2,4,6-trinitrobenzoic acid Chemical compound OC(=O)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KAQBNBSMMVTKRN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- RUOKPLVTMFHRJE-UHFFFAOYSA-N benzene-1,2,3-triamine Chemical compound NC1=CC=CC(N)=C1N RUOKPLVTMFHRJE-UHFFFAOYSA-N 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract 1
- 229910003445 palladium oxide Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 229910003446 platinum oxide Inorganic materials 0.000 abstract 1
- -1 trinitrobenzene compound Chemical class 0.000 abstract 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
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- 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
- C07C37/045—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 by substitution of a group bound to the ring by nitrogen
- C07C37/05—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 by substitution of a group bound to the ring by nitrogen by substitution of a NH2 group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Phloroglucinol is prepared by hydrogenating trinitrobenzene or trinitobenzoic acid, preferably under pressure, in a solution in a solvent containing at least 10% by weight of the trinitrobenzene compound and in the presence of a hydrogenation catalyst at a temperature of at least 40 DEG C., separating the catalyst and solvent from the hydrogenated mixture, hydrolysing the hydrogenated mixture with acid and recovering phloroglucinol from the resulting mixture. Suitable solvents are, for example, ketones, alcohols, esters and ethers. The preferred catalyst is Raney nickel but other catalysts may be used, e.g. platinum, palladium and platinum oxide. Triaminobenzene and triaminobenzoic acid are formed as intermediates by the catalytic hydrogenation of trinitrobenzene and trinitrobenzoic acid respectively.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3705864A GB1106088A (en) | 1964-09-10 | 1964-09-10 | Process for the preparation of phloroglucinol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3705864A GB1106088A (en) | 1964-09-10 | 1964-09-10 | Process for the preparation of phloroglucinol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1106088A true GB1106088A (en) | 1968-03-13 |
Family
ID=10393406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3705864A Expired GB1106088A (en) | 1964-09-10 | 1964-09-10 | Process for the preparation of phloroglucinol |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1106088A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2351076A1 (en) * | 1976-05-14 | 1977-12-09 | Akzo Nv | PROCESS FOR PREPARING THE PHLOROGLUCIN |
| US4296260A (en) * | 1978-09-18 | 1981-10-20 | Akzona Incorporated | Process for the preparation of phloroglucinol |
| US7217840B2 (en) | 2002-06-11 | 2007-05-15 | Phv Analytic | Method for preparing 1,3,5-triaminobenzene and hydrolyzing it into high-purity phloroglucinal |
| RU2389716C2 (en) * | 2008-04-03 | 2010-05-20 | Федеральное государственное унитарное предприятие "Государственный научно-исследовательский институт "Кристалл" | 1,3,5-trihydroxybezene synthesis method |
-
1964
- 1964-09-10 GB GB3705864A patent/GB1106088A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2351076A1 (en) * | 1976-05-14 | 1977-12-09 | Akzo Nv | PROCESS FOR PREPARING THE PHLOROGLUCIN |
| US4296260A (en) * | 1978-09-18 | 1981-10-20 | Akzona Incorporated | Process for the preparation of phloroglucinol |
| US7217840B2 (en) | 2002-06-11 | 2007-05-15 | Phv Analytic | Method for preparing 1,3,5-triaminobenzene and hydrolyzing it into high-purity phloroglucinal |
| RU2389716C2 (en) * | 2008-04-03 | 2010-05-20 | Федеральное государственное унитарное предприятие "Государственный научно-исследовательский институт "Кристалл" | 1,3,5-trihydroxybezene synthesis method |
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