GB757455A - A process for the separation of tertiary-alkyl-substituted benzoic acids from mixtures containing said acids - Google Patents
A process for the separation of tertiary-alkyl-substituted benzoic acids from mixtures containing said acidsInfo
- Publication number
- GB757455A GB757455A GB21132/54A GB2113254A GB757455A GB 757455 A GB757455 A GB 757455A GB 21132/54 A GB21132/54 A GB 21132/54A GB 2113254 A GB2113254 A GB 2113254A GB 757455 A GB757455 A GB 757455A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tertiary
- butyl
- alkyl
- acids
- aqueous phase
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Tertiary-alkyl-substituted benzoic acids are separated from a crude oxidation product obtained by the oxidation of one or more aromatic hydrocarbons including a tertiary-alkyl-substituted benzene hydrocarbon having at least one tertiary-alkyl radical and at least one non-tertiary-alkyl radical as substituents in its benzene ring, by treating said crude oxidation product at a temperature above about 50 DEG C. with sufficient aqueous alkali-metal or ammonium base to form a mixture having a pH between 7 and 8, separating an aqueous phase therefrom, adding to said aqueous phase at a temperature above about 50 DEG C. sufficient concentrated strong mineral acid to form a mixture having a pH between 6 and 7 and separating therefrom a solid phase consisting of said tertiary-alkyl-substituted benzoic acid. The tertiary-alkyl-substituted benzene hydrocarbon may contain a tertiary-alkyl radical of 4 to 21 carbon atoms and a non-tertiary-alkyl radical of 1 to 4 carbon atoms and the following hydrocarbons are mentioned: o-, m- and p-tertiary-butyl toluene, o-, m- and p-tertiary-amyl toluene, the o-, m- and p-isomers of tertiary-nonyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl, eicosyl and heneicosyl toluenes, 3 : 5-di-tertiary-butyl toluene, the tertiary - butyl xylenes, the tertiary - heptyl xylenes and 2-propyl-4-tertiary-butyl ethyl benzene. These form the corresponding tertiary alkyl benzoic acids such as tertiary-butyl and tertiary-amyl benzoic acid, and 3 : 5-di-tertiary butyl benzoic acid. The alkali-metal or ammonium bases specified are hydroxides and carbonates such as sodium, potassium, lithium or ammonium hydroxides and sodium carbonate or bicarbonate. Strong mineral acids specified are sulphuric, hydrochloric and phosphoric acids. The process may be a batch, semicontinuous or continuous operation conducted at atmospheric or superatmospheric pressure. Separation between isomers of tertiary-alkyl benzoic acids may be effected by controlled stepwise acidification of the aqueous phase. With a mixture of m- and p-tertiary-butyl benzoic acids, acidification of the hot aqueous phase to a pH between 6 and 7 results in the separation of the p-isomer, further acidification to pH between 5.3 and 6 causes separation of the m-isomer. Phthalic acids such as terephthalic acid, separate on acidification of the aqueous phase to a pH below 5.3. In examples: (1) p-tertiary-butyl toluene is oxidized in the presence of a cobalt catalyst and the product treated with aqueous sodium hydroxide to bring the pH to 7.5, the aqueous phase is treated with concentrated sulphuric acid to a pH of 6.5 when p-tertiary-butyl benzoic acid separates; the colour of this acid on heating is compared with that of crude tertiary-butyl benzoic acid; (2) a mixture of m- and p-tertiary butyl toluene is oxidized as in (1) and treated with aqueous sodium hydroxide to a pH of 7.8, the aqueous phase acidified with sulphuric acid to pH 6.5 to give p-tertiary-butyl benzoic acid, further acidification of the mother-liquors gives a mixture of m-and p-tertiary butyl benzoic acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US757455XA | 1953-07-20 | 1953-07-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB757455A true GB757455A (en) | 1956-09-19 |
Family
ID=22127730
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB21132/54A Expired GB757455A (en) | 1953-07-20 | 1954-07-20 | A process for the separation of tertiary-alkyl-substituted benzoic acids from mixtures containing said acids |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1011411B (en) |
GB (1) | GB757455A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1112508B (en) * | 1957-05-06 | 1961-08-10 | Dow Chemical Co | Process for maintaining the catalytic effectiveness of cobalt salts during the oxygen oxidation of aromatic hydrocarbons |
US3050554A (en) * | 1958-07-07 | 1962-08-21 | Shell Oil Co | Catalytic oxidation of tertiary butyl toluene and recovery of oxygenated products |
FR2409252A1 (en) * | 1977-11-17 | 1979-06-15 | Dynamit Nobel Ag | PURIFICATION PROCESS OF P-TOLYLIC ACID OBTAINED BY OXIDATION OF P-XYLENE |
EP1131276A1 (en) * | 1998-11-24 | 2001-09-12 | Tsong-Dar Vincent Lin | Process of purifying and producing high purity aromatic polycarboxylic acids and derivatives thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1942826A (en) * | 1930-03-06 | 1934-01-09 | Dow Chemical Co | Method for separation of ortho-and para-halobenzoic acids |
US2578654A (en) * | 1950-01-28 | 1951-12-18 | Shell Dev | Preparation of tertiary-alkyl-substituted benzene carboxylic acids |
-
1954
- 1954-07-20 GB GB21132/54A patent/GB757455A/en not_active Expired
- 1954-07-20 DE DEN9228A patent/DE1011411B/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1112508B (en) * | 1957-05-06 | 1961-08-10 | Dow Chemical Co | Process for maintaining the catalytic effectiveness of cobalt salts during the oxygen oxidation of aromatic hydrocarbons |
US3050554A (en) * | 1958-07-07 | 1962-08-21 | Shell Oil Co | Catalytic oxidation of tertiary butyl toluene and recovery of oxygenated products |
FR2409252A1 (en) * | 1977-11-17 | 1979-06-15 | Dynamit Nobel Ag | PURIFICATION PROCESS OF P-TOLYLIC ACID OBTAINED BY OXIDATION OF P-XYLENE |
EP1131276A1 (en) * | 1998-11-24 | 2001-09-12 | Tsong-Dar Vincent Lin | Process of purifying and producing high purity aromatic polycarboxylic acids and derivatives thereof |
EP1131276A4 (en) * | 1998-11-24 | 2002-09-18 | Tsong-Dar Vincent Lin | Process of purifying and producing high purity aromatic polycarboxylic acids and derivatives thereof |
Also Published As
Publication number | Publication date |
---|---|
DE1011411B (en) | 1957-07-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB626095A (en) | Manufacture of phenols | |
GB1173958A (en) | Improvements in or relating to the Purification of Unsaturated Hydrocarbons | |
GB757455A (en) | A process for the separation of tertiary-alkyl-substituted benzoic acids from mixtures containing said acids | |
US2459540A (en) | Separation of alkyl-alkoxyphenol mixtures | |
GB1424370A (en) | Manufacture of dicarboxylic acid diesters with substantial waste water purification | |
GB1498995A (en) | Method for separating and recovering hydroquinone | |
US2050188A (en) | Method of producing derivatives of hydroxy aryl compounds | |
US1951747A (en) | Process for the manufacture of esters | |
US2695313A (en) | Oxidation of nonaromatic organic compounds | |
US2720549A (en) | Recovery of phenol | |
GB582057A (en) | Improvements in and relating to the separation of phenols | |
US2744149A (en) | Preparation of m- and p-cymene mixture by isomerization of cymene | |
GB706107A (en) | Improvements in or relating to the separation of dimethylphenols | |
US3987120A (en) | Recovery of mesitylene and ethyltoluenes from petroleum naphtha reformate | |
ES421209A1 (en) | Process for separating high purity aromatic hydrocarbons from mixtures containing them | |
GB660838A (en) | Improvements in or relating to the treatment of alcoholic organic material | |
US2713072A (en) | Production of bis | |
GB443151A (en) | Manufacture of organic acid anhydrides | |
US2626890A (en) | Sweetening gasoline | |
GB669756A (en) | Improvements in or relating to new methods of conducting the grignard synthesis | |
GB757658A (en) | A process for separating tertiary-alkyl substituted benzoic acids from mixtures containing said acids | |
GB1099784A (en) | Separating alkane sulphonic acids from mixtures | |
GB857098A (en) | Improvements in and relating to the oxidation of alkyl substituted aromatic compounds | |
Kaneyuki | The Reactions of Ester with Acyl Chloride in the Presence of Aluminum Chloride. V. Reaction Mechanism of the Benzoylation of Diethyl Malonate | |
Takahasi | The Action of Hydrogen Bromide and Oxygen on Various Ethenoid Compounds. II |