GB623836A - Manufacture of terephthalic acid - Google Patents
Manufacture of terephthalic acidInfo
- Publication number
- GB623836A GB623836A GB1258447A GB1258447A GB623836A GB 623836 A GB623836 A GB 623836A GB 1258447 A GB1258447 A GB 1258447A GB 1258447 A GB1258447 A GB 1258447A GB 623836 A GB623836 A GB 623836A
- Authority
- GB
- United Kingdom
- Prior art keywords
- xylene
- terephthalic acid
- solid
- catalyst
- reaction medium
- 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
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
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
Terephthalic acid is manufactured by passing oxygen, air or other mixture of gases containing oxygen into liquid p-xylene at a temperature above 100 DEG C., said liquid containing as an oxidation catalyst a small proportion of an oil-soluble compound of cobalt, continuing the passage of gas until a substantial amount of solid separates from the reaction medium, and recovering this solid. The catalyst may be suspended or preferably dissolved in the p-xylene, advantageously in an amount corresponding to 0.002 to 0.02 per cent of metal, based on the weight of p-xylene. When working at atmospheric pressure, the temperature is conveniently 130-140 DEG C. at the outset and may later be raised to 145 DEG C. or higher. The process may be made continuous by continuously or periodically adding p-xylene and withdrawing the separated solid. The p-xylene should be free from antioxidants and catalyst poisons, but may contain minor proportions of hydrocarbon impurities such as benzene, toluene, ethylbenzene or o- or m-xylene, or inert diluents, e.g. chlorobenzenes. The oxidizing gas should be well distributed by injecting it through a sintered glass or porous ceramic disc, or preferably through high velocity jets, with or without the use of a high-speed agitator. The process is conveniently effected in plant constructed from glass, nickel, enamelled metal or anodized aluminium, or lined with tantalum. The presence of chromium, copper or alloys containing them is undesirable, though a measure of success can be achieved with stainless steel equipment if a small proportion of a lead or barium salt is present in the reaction medium. The product may be purified by washing with a hot lower aliphatic alcohol, e.g. methyl, ethyl or isopropyl alcohol, preferably with boiling methyl alcohol. Alternatively, the terephthalic acid may be isolated in the form of an ester by esterifying the separated solid with excess of a lower aliphatic alcohol, e.g. methyl (preferred), ethyl or isopropyl alcohol, with or without the aid of an esterification catalyst, and separating the terephthalic acid ester from the esterified solid. The residues from either method of purification may be returned to the reaction medium for further oxidation. Alternatively, partial oxidation products in the separated solid may be oxidized to terephthalic acid by the action of mild oxidative chemical reagents, e.g. dilute nitric acid, or permanganates in the presence of alkali. Examples illustrate various features of the invention.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1258447A GB623836A (en) | 1947-05-09 | 1947-05-09 | Manufacture of terephthalic acid |
ES0183560A ES183560A1 (en) | 1947-05-09 | 1948-05-04 | IMPROVEMENTS IN THE MANUFACTURE OF TEREPHTHALIC ACID |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1258447A GB623836A (en) | 1947-05-09 | 1947-05-09 | Manufacture of terephthalic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
GB623836A true GB623836A (en) | 1949-05-24 |
Family
ID=10007323
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1258447A Expired GB623836A (en) | 1947-05-09 | 1947-05-09 | Manufacture of terephthalic acid |
Country Status (2)
Country | Link |
---|---|
ES (1) | ES183560A1 (en) |
GB (1) | GB623836A (en) |
Cited By (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2656377A (en) * | 1951-01-16 | 1953-10-20 | California Research Corp | Process for the separation of isophthalic and terephthalic diesters |
US2673217A (en) * | 1951-09-21 | 1954-03-23 | Eastman Kodak Co | Selective oxidation of substituted aromatic compounds using aldehyde-activated catalysts |
US2696499A (en) * | 1952-07-01 | 1954-12-07 | Richfield Oil Corp | Preparation of toluic acids |
US2698865A (en) * | 1951-08-06 | 1955-01-04 | Imhausen & Compagnie G M B H | Process for production of aromatic polycarboxylic acids |
US2723994A (en) * | 1951-01-15 | 1955-11-15 | Shell Dev | Oxidation of xylene and toluic acid mixtures to phthalic acids |
US2727919A (en) * | 1952-08-21 | 1955-12-20 | Hercules Powder Co Ltd | Process for oxidizing polyalkylaromatic hydrocarbons and derivatives thereof using an acid anhydride catalyst |
US2732399A (en) * | 1956-01-24 | Process for separating isophthalic acid | ||
US2733266A (en) * | 1956-01-31 | mckinnis | ||
US2741633A (en) * | 1952-11-17 | 1956-04-10 | Union Oil Co | Separation of isophthalic and terephthalic acids |
US2742494A (en) * | 1952-09-26 | 1956-04-17 | Hercules Powder Co Ltd | Mixed esters of phthalic acids and process for production thereof |
US2746990A (en) * | 1953-02-02 | 1956-05-22 | Shell Dev | Preparation of terephthalic acid |
US2749363A (en) * | 1951-11-23 | 1956-06-05 | Shell Dev | Purification of aromatic acids |
DE949564C (en) * | 1951-04-13 | 1956-09-20 | Imhausen & Co G M B H | Process for the preparation of terephthalic acid monomethyl ester |
US2764611A (en) * | 1951-08-06 | 1956-09-25 | Imhausen Werke G M B H | Process for production of aromatic polycarboxylic acids |
US2772305A (en) * | 1952-08-26 | 1956-11-27 | California Research Corp | Oxidation of toluate esters and xylene mixtures |
US2785199A (en) * | 1952-07-01 | 1957-03-12 | Richfield Oil Corp | Purification of toluic acids |
US2788367A (en) * | 1953-03-05 | 1957-04-09 | Union Oil Co | Xylene oxidation process |
US2810750A (en) * | 1952-07-07 | 1957-10-22 | Imhausen Werke G M B H | Process for converting aromatic alcohols to aromatic carboxylic acids |
US2821551A (en) * | 1951-08-06 | 1958-01-28 | Imhausen Werke G M B H | Process for production of aromatic carboxylic acids |
US2833819A (en) * | 1957-06-14 | 1958-05-06 | Mid Century Corp | Process for the preparation of isophthalic and terephthalic acids |
US2833820A (en) * | 1957-06-14 | 1958-05-06 | Mid Century Corp | Process for the preparation of isophthalic and terephthalic acids |
DE1035642B (en) * | 1954-10-06 | 1958-08-07 | California Research Corp | Process for the preparation of benzene polycarboxylic acids |
DE969994C (en) * | 1951-04-14 | 1958-08-07 | Imhausen & Co G M B H | Process for the preparation of terephthalic acid esters by the oxidation of p-xylene |
US2850527A (en) * | 1952-03-31 | 1958-09-02 | Bayer Ag | Process for the production of aromatic dicarboxylic acids |
US2858334A (en) * | 1954-11-26 | 1958-10-28 | Mid Century Corp | Preparation of phthalic acids |
DE971420C (en) * | 1951-05-05 | 1959-01-29 | Imhausen Werke G M B H | Process for the preparation of isophthalic acid monomethyl ester |
DE971421C (en) * | 1951-06-27 | 1959-01-29 | Imhausen Werke G M B H | Process for the production of phthalic acid monomethyl ester |
US2879289A (en) * | 1956-06-27 | 1959-03-24 | Du Pont | Oxidation of alkyl benzenes in the presence of alkanols |
DE1053490B (en) * | 1954-12-08 | 1959-03-26 | Mid Century Corp | Process for the preparation of dimethyl terephthalate |
DE1055521B (en) * | 1953-10-19 | 1959-04-23 | California Research Corp | Process for the separation of mixtures of the dimethyl esters of iso- and terephthalic acid |
US2892864A (en) * | 1958-03-06 | 1959-06-30 | Hercules Powder Co Ltd | Esterification of terephthalic acid in presence of metal oxidation catalyst |
US2899466A (en) * | 1959-08-11 | Purification of terephthalic acid | ||
DE970794C (en) * | 1951-06-13 | 1959-09-10 | Imhausen Werke G M B H | Process for the production of terephthalic acid esters |
DE970795C (en) * | 1951-07-05 | 1959-09-10 | Imhausen Werke G M B H | Process for the production of pure terephthalic acid and isophthalic acid methyl ester |
US2920106A (en) * | 1957-07-26 | 1960-01-05 | Sun Oil Co | Partial oxidation of alkyl aromatics |
US2970164A (en) * | 1956-09-07 | 1961-01-31 | Sun Oil Co | Preparation of esters by partial oxidation of petroleum fractions |
DE975712C (en) * | 1951-08-07 | 1962-07-05 | Witten Gmbh Chem Werke | Process for the preparation of aromatic polycarboxylic acids or their esters by oxidation of alkyl aromatics |
DE1136688B (en) * | 1957-02-09 | 1962-09-20 | Robert Sancier Aries | Process for the preparation of benzene dicarboxylic acids |
DE1139827B (en) * | 1961-04-15 | 1962-11-22 | Chemische Werke Witten Gesell schaft mit beschrankter Haftung, Witten | Process for the improved work-up of mother liquors containing terephthalic acid dimethyl ester and isophthalic acid dimethyl ester. |
US3089907A (en) * | 1958-04-21 | 1963-05-14 | Mid Century Corp | Pressure controlled liquid phase oxidation process for aromatic acid production |
DE976866C (en) * | 1951-06-23 | 1964-07-16 | Witten Gmbh Chem Werke | Process for the production of terephthalic acid esters |
US3209024A (en) * | 1963-02-28 | 1965-09-28 | Sun Oil Co | Preparation of naphthalene-2, 6-dicarboxylic acid |
-
1947
- 1947-05-09 GB GB1258447A patent/GB623836A/en not_active Expired
-
1948
- 1948-05-04 ES ES0183560A patent/ES183560A1/en not_active Expired
Cited By (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2732399A (en) * | 1956-01-24 | Process for separating isophthalic acid | ||
US2899466A (en) * | 1959-08-11 | Purification of terephthalic acid | ||
US2733266A (en) * | 1956-01-31 | mckinnis | ||
US2723994A (en) * | 1951-01-15 | 1955-11-15 | Shell Dev | Oxidation of xylene and toluic acid mixtures to phthalic acids |
US2656377A (en) * | 1951-01-16 | 1953-10-20 | California Research Corp | Process for the separation of isophthalic and terephthalic diesters |
DE949564C (en) * | 1951-04-13 | 1956-09-20 | Imhausen & Co G M B H | Process for the preparation of terephthalic acid monomethyl ester |
DE969994C (en) * | 1951-04-14 | 1958-08-07 | Imhausen & Co G M B H | Process for the preparation of terephthalic acid esters by the oxidation of p-xylene |
DE971420C (en) * | 1951-05-05 | 1959-01-29 | Imhausen Werke G M B H | Process for the preparation of isophthalic acid monomethyl ester |
DE970794C (en) * | 1951-06-13 | 1959-09-10 | Imhausen Werke G M B H | Process for the production of terephthalic acid esters |
DE976866C (en) * | 1951-06-23 | 1964-07-16 | Witten Gmbh Chem Werke | Process for the production of terephthalic acid esters |
DE971421C (en) * | 1951-06-27 | 1959-01-29 | Imhausen Werke G M B H | Process for the production of phthalic acid monomethyl ester |
DE970795C (en) * | 1951-07-05 | 1959-09-10 | Imhausen Werke G M B H | Process for the production of pure terephthalic acid and isophthalic acid methyl ester |
US2821551A (en) * | 1951-08-06 | 1958-01-28 | Imhausen Werke G M B H | Process for production of aromatic carboxylic acids |
US2698865A (en) * | 1951-08-06 | 1955-01-04 | Imhausen & Compagnie G M B H | Process for production of aromatic polycarboxylic acids |
US2764611A (en) * | 1951-08-06 | 1956-09-25 | Imhausen Werke G M B H | Process for production of aromatic polycarboxylic acids |
DE975712C (en) * | 1951-08-07 | 1962-07-05 | Witten Gmbh Chem Werke | Process for the preparation of aromatic polycarboxylic acids or their esters by oxidation of alkyl aromatics |
US2673217A (en) * | 1951-09-21 | 1954-03-23 | Eastman Kodak Co | Selective oxidation of substituted aromatic compounds using aldehyde-activated catalysts |
US2749363A (en) * | 1951-11-23 | 1956-06-05 | Shell Dev | Purification of aromatic acids |
US2850527A (en) * | 1952-03-31 | 1958-09-02 | Bayer Ag | Process for the production of aromatic dicarboxylic acids |
US2785199A (en) * | 1952-07-01 | 1957-03-12 | Richfield Oil Corp | Purification of toluic acids |
US2696499A (en) * | 1952-07-01 | 1954-12-07 | Richfield Oil Corp | Preparation of toluic acids |
US2810750A (en) * | 1952-07-07 | 1957-10-22 | Imhausen Werke G M B H | Process for converting aromatic alcohols to aromatic carboxylic acids |
US2727919A (en) * | 1952-08-21 | 1955-12-20 | Hercules Powder Co Ltd | Process for oxidizing polyalkylaromatic hydrocarbons and derivatives thereof using an acid anhydride catalyst |
US2772305A (en) * | 1952-08-26 | 1956-11-27 | California Research Corp | Oxidation of toluate esters and xylene mixtures |
US2742494A (en) * | 1952-09-26 | 1956-04-17 | Hercules Powder Co Ltd | Mixed esters of phthalic acids and process for production thereof |
US2741633A (en) * | 1952-11-17 | 1956-04-10 | Union Oil Co | Separation of isophthalic and terephthalic acids |
US2746990A (en) * | 1953-02-02 | 1956-05-22 | Shell Dev | Preparation of terephthalic acid |
US2788367A (en) * | 1953-03-05 | 1957-04-09 | Union Oil Co | Xylene oxidation process |
DE1055521B (en) * | 1953-10-19 | 1959-04-23 | California Research Corp | Process for the separation of mixtures of the dimethyl esters of iso- and terephthalic acid |
DE1035642B (en) * | 1954-10-06 | 1958-08-07 | California Research Corp | Process for the preparation of benzene polycarboxylic acids |
US2858334A (en) * | 1954-11-26 | 1958-10-28 | Mid Century Corp | Preparation of phthalic acids |
DE1053490B (en) * | 1954-12-08 | 1959-03-26 | Mid Century Corp | Process for the preparation of dimethyl terephthalate |
US2879289A (en) * | 1956-06-27 | 1959-03-24 | Du Pont | Oxidation of alkyl benzenes in the presence of alkanols |
US2970164A (en) * | 1956-09-07 | 1961-01-31 | Sun Oil Co | Preparation of esters by partial oxidation of petroleum fractions |
DE1136688B (en) * | 1957-02-09 | 1962-09-20 | Robert Sancier Aries | Process for the preparation of benzene dicarboxylic acids |
US2833820A (en) * | 1957-06-14 | 1958-05-06 | Mid Century Corp | Process for the preparation of isophthalic and terephthalic acids |
US2833819A (en) * | 1957-06-14 | 1958-05-06 | Mid Century Corp | Process for the preparation of isophthalic and terephthalic acids |
US2920106A (en) * | 1957-07-26 | 1960-01-05 | Sun Oil Co | Partial oxidation of alkyl aromatics |
US2892864A (en) * | 1958-03-06 | 1959-06-30 | Hercules Powder Co Ltd | Esterification of terephthalic acid in presence of metal oxidation catalyst |
US3089907A (en) * | 1958-04-21 | 1963-05-14 | Mid Century Corp | Pressure controlled liquid phase oxidation process for aromatic acid production |
DE1139827B (en) * | 1961-04-15 | 1962-11-22 | Chemische Werke Witten Gesell schaft mit beschrankter Haftung, Witten | Process for the improved work-up of mother liquors containing terephthalic acid dimethyl ester and isophthalic acid dimethyl ester. |
US3209024A (en) * | 1963-02-28 | 1965-09-28 | Sun Oil Co | Preparation of naphthalene-2, 6-dicarboxylic acid |
Also Published As
Publication number | Publication date |
---|---|
ES183560A1 (en) | 1948-07-01 |
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