GB1044977A - Improvements in or relating to the production of acid anhydrides - Google Patents
Improvements in or relating to the production of acid anhydridesInfo
- Publication number
- GB1044977A GB1044977A GB2271463A GB2271463A GB1044977A GB 1044977 A GB1044977 A GB 1044977A GB 2271463 A GB2271463 A GB 2271463A GB 2271463 A GB2271463 A GB 2271463A GB 1044977 A GB1044977 A GB 1044977A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anhydride
- catalyst
- substituted
- acid anhydrides
- palmitic
- 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
- 150000008065 acid anhydrides Chemical class 0.000 title 1
- -1 ROhal Chemical class 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- OLENANGIJWDOPG-UHFFFAOYSA-N (2-chlorobenzoyl) 2-chlorobenzoate Chemical compound ClC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1Cl OLENANGIJWDOPG-UHFFFAOYSA-N 0.000 abstract 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- NGEZPLCPKXKLQQ-VOTSOKGWSA-N (e)-4-(3-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=CC(\C=C\C(C)=O)=C1 NGEZPLCPKXKLQQ-VOTSOKGWSA-N 0.000 abstract 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 abstract 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 abstract 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- 235000021314 Palmitic acid Nutrition 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid ester group Chemical group C(CCCCCCCCCCC)(=O)O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 1
- NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000002943 palmitic acids Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/04—Monocyclic monocarboxylic acids
- C07C63/06—Benzoic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/70—Monocarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Monobasic carboxylic acid anhydrides are prepared by the reaction of equimolar quantities of an acyl halide, ROhal, and an alkali metal salt or ammonium salt of a monobasic acid, R1COOH, wherein R and R1 may be the same or different and represent either a substituted or unsubstituted aryl radical or an alkyl radical containing at least 11 carbon atoms, in an aqueous medium in the presence of a tertiary base as catalyst and at ambient temperatures and pressures and separating the resulting solid anhydride from the liquid reaction mixture. Suitable starting materials are the acyl derivatives and salts of benzoic acid which may be substituted in the nucleus by, e.g., nitro-groups, halogen atoms or C1-C5 alkyl groups. Suitable aliphatic reactants are the appropriate derivatives of lauric and palmitic acids. The catalyst may be a trialkylamine, e.g. triethylamine, or a pyridine, e.g. 3-aminopyridine, picolines, lutidines or colidines. Examples describe the preparation of (1), (4), (5) and (5A) benzoic anhydride, (2) toluic anhydride, (3) 3: 5-dinitrobenzoic anhydride, (6) o - chlorobenzoic anhydride, (7) lauroyl anhydride and (8) palmitic anhydride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2271463A GB1044977A (en) | 1963-06-07 | 1963-06-07 | Improvements in or relating to the production of acid anhydrides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2271463A GB1044977A (en) | 1963-06-07 | 1963-06-07 | Improvements in or relating to the production of acid anhydrides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1044977A true GB1044977A (en) | 1966-10-05 |
Family
ID=10183929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2271463A Expired GB1044977A (en) | 1963-06-07 | 1963-06-07 | Improvements in or relating to the production of acid anhydrides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1044977A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029176A1 (en) * | 1979-11-20 | 1981-05-27 | BASF Aktiengesellschaft | Process for the production of carboxylic anhydrides |
| US4381266A (en) * | 1978-05-18 | 1983-04-26 | Ciba-Geigy Corporation | (N-Substituted benzoyl)halobenzoic acid anhydrides |
-
1963
- 1963-06-07 GB GB2271463A patent/GB1044977A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4381266A (en) * | 1978-05-18 | 1983-04-26 | Ciba-Geigy Corporation | (N-Substituted benzoyl)halobenzoic acid anhydrides |
| EP0029176A1 (en) * | 1979-11-20 | 1981-05-27 | BASF Aktiengesellschaft | Process for the production of carboxylic anhydrides |
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