GB864106A - Preparation of phthalic acids by oxidation - Google Patents
Preparation of phthalic acids by oxidationInfo
- Publication number
- GB864106A GB864106A GB2982559A GB2982559A GB864106A GB 864106 A GB864106 A GB 864106A GB 2982559 A GB2982559 A GB 2982559A GB 2982559 A GB2982559 A GB 2982559A GB 864106 A GB864106 A GB 864106A
- Authority
- GB
- United Kingdom
- Prior art keywords
- xylene
- oxidation
- oxidate
- zone
- toluate
- 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
- 230000003647 oxidation Effects 0.000 title abstract 12
- 238000007254 oxidation reaction Methods 0.000 title abstract 12
- 150000003022 phthalic acids Chemical class 0.000 title abstract 2
- 239000008096 xylene Substances 0.000 abstract 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 11
- -1 alkyl toluate Chemical compound 0.000 abstract 6
- 239000007789 gas Substances 0.000 abstract 4
- 239000007800 oxidant agent Substances 0.000 abstract 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000007791 liquid phase Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 abstract 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 abstract 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 abstract 1
- 150000003738 xylenes Chemical class 0.000 abstract 1
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
<PICT:0864106/IV (b)/1> An oxidation process for the production of phthalic acids and esters comprises continuously introducing a xylene and a lower alkyl toluate into the first of a series of oxidation zones, continuously oxidising said xylene and said alkyl toluate in said zone in the liquid phase by passing an oxygen-containing gas p therethrough, continuously withdrawing oxidate containing unreacted alkyl toluate from said first zone, passing said withdrawn oxidate to a second oxidation zone while simultaneously introducing additional xylene to said second zone, continuing the oxidation of said withdrawn oxidate in the presence of said additional xylene in said second oxidation zone in the liquid phase by passing an oxygen-containing gas therethrough and continuously withdrawing oxidate containing a monoalkyl phthalate and a phthalic acid from said second oxidation zone, the amount of xylene introduced into each oxidation zone being proportioned to provide approximately equal rates of oxidation in each zone, in terms of acid number increase per hour, and the total amount of xylene introduced being in excess of that stoichiometrically equivalent to the amount of lower alkyl toluate introduced in the process. The terms "phthalic acid," "toluic acid" and "xylene" are intended to include all the various isomers and the term "lower alkyl" is defined as containing 1 to 4 carbon atoms. The oxidation may be carried out at 120-230 DEG C. and at elevated pressure in the presence of an oxidation catalyst e.g. cobalt toluate using air as the oxidising gas. In a preferred embodiment illustrated in Fig. 2 alkyl toluate is introduced into oxidiser No. 1 through A, residue from previous oxidations e.g. partially oxidised xylenes and toluates, is introduced through B, catalyst is introduced through C and the off gases from oxidiser No. 2 containing both oxygen and xylene are introduced through E. The oxidate is withdrawn from oxidiser No. 1 and passed to oxidiser No. 2 through D and additional xylene simultaneously introduced through F. The oxidate is withdrawn through G, unreacted xylene removed in the xylene stripper and the stripped oxidate esterified and then distilled to give an alkyl toluate which is recycled, a dialkyl phthalate and a high boiling residue. In examples p-xylene and methyl p-toluate are oxidised and the stripped oxidate esterified with methanol. Specification 809,730 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75932458A | 1958-09-05 | 1958-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB864106A true GB864106A (en) | 1961-03-29 |
Family
ID=25055227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2982559A Expired GB864106A (en) | 1958-09-05 | 1959-09-01 | Preparation of phthalic acids by oxidation |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE581049A (en) |
| CH (1) | CH377795A (en) |
| DE (1) | DE1114472B (en) |
| ES (1) | ES251660A1 (en) |
| GB (1) | GB864106A (en) |
| NL (1) | NL242734A (en) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998027029A1 (en) * | 1996-12-18 | 1998-06-25 | Twenty-First Century Research Corporation | Methods of preparing an intermediate oxidation product from a hydrocarbon by utilizing an activated initiator |
| US5877341A (en) * | 1996-08-21 | 1999-03-02 | Twenty-First Century Research Corporation | Methods and devices for controlling the reaction rate of a hydrocarbon to an intermediate oxidation product by pressure drop adjustments |
| US5908589A (en) * | 1997-12-08 | 1999-06-01 | Twenty-First Century Research Corporation | Methods for separating catalyst from oxidation mixtures containing dibasic acids |
| US5929277A (en) * | 1997-09-19 | 1999-07-27 | Twenty-First Century Research Corporation | Methods of removing acetic acid from cyclohexane in the production of adipic acid |
| US5939582A (en) * | 1996-01-17 | 1999-08-17 | Twenty-First Century Research Corporation | Reaction control by regulating internal condensation inside a reactor |
| US5998572A (en) * | 1996-11-12 | 1999-12-07 | Rpc Inc. | Methods and devices for controlling the oxidation of a hydrocarbon to an acid by regulating temperature/conversion relationship in multi-stage arrangements |
| US6037491A (en) * | 1997-07-25 | 2000-03-14 | Rpc Inc. | Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent to hydrocarbon ratio |
| US6039902A (en) * | 1996-06-24 | 2000-03-21 | Rpc Inc. | Methods of recycling catalyst in oxidations of hydrocarbons |
| US6129875A (en) * | 1998-02-19 | 2000-10-10 | Rpc Inc. | Process of separating catalyst from oxidation mixtures |
| US6143927A (en) * | 1996-06-24 | 2000-11-07 | Rpc Inc. | Methods for removing catalyst after oxidation of hydrocarbons |
| US6218573B1 (en) | 1998-07-02 | 2001-04-17 | Rpc Inc. | Methods of recovering catalyst in solution in the oxidation of cyclohexane to adipic acid |
| US6232495B1 (en) | 1998-02-09 | 2001-05-15 | Rpc Inc. | Methods for treating cobalt catalyst in oxidation mixtures resulting from oxidation of hydrocarbons to dibasic acids |
| US6288274B1 (en) | 1996-08-21 | 2001-09-11 | Rpc Inc. | Methods and devices for controlling the reaction rate and/or reactivity of hydrocarbon to an intermediate oxidation product by adjusting the oxidant consumption rate |
| US6288270B1 (en) | 1996-06-24 | 2001-09-11 | Rpc Inc. | Methods for controlling the reaction rate of a hydrocarbon to an acid by making phase-related adjustments |
| US6340420B1 (en) | 1998-07-06 | 2002-01-22 | Rpc Inc. | Methods of treating the oxidation mixture of hydrocarbons to respective dibasic acids |
| US6359173B1 (en) | 1996-06-24 | 2002-03-19 | Rpc Inc. | Methods and devices for oxidizing a hydrocarbon to form an acid |
| US6417128B1 (en) | 1999-04-20 | 2002-07-09 | Rpc, Inc. | Methods and replacing water and cyclohexanone with acetic acid in aqueous solutions of catalyst |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2010137C3 (en) * | 1970-03-04 | 1979-07-05 | Dynamit Nobel Ag, 5210 Troisdorf | Process for the preparation of dimethyl terephthalate |
| BE791138R (en) | 1971-12-18 | 1973-05-09 | Dynamit Nobel Ag | PROCESS FOR PREPARING THE DIMETHYL ESTER OF TEREPHTHALIC ACID |
-
0
- NL NL242734D patent/NL242734A/xx unknown
-
1959
- 1959-07-21 ES ES0251660A patent/ES251660A1/en not_active Expired
- 1959-07-25 BE BE581049A patent/BE581049A/en unknown
- 1959-08-27 DE DEH37285A patent/DE1114472B/en active Pending
- 1959-09-01 CH CH7764259A patent/CH377795A/en unknown
- 1959-09-01 GB GB2982559A patent/GB864106A/en not_active Expired
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5939582A (en) * | 1996-01-17 | 1999-08-17 | Twenty-First Century Research Corporation | Reaction control by regulating internal condensation inside a reactor |
| US6143927A (en) * | 1996-06-24 | 2000-11-07 | Rpc Inc. | Methods for removing catalyst after oxidation of hydrocarbons |
| US6359173B1 (en) | 1996-06-24 | 2002-03-19 | Rpc Inc. | Methods and devices for oxidizing a hydrocarbon to form an acid |
| US6294689B1 (en) | 1996-06-24 | 2001-09-25 | Rpc Inc. | Methods for removing catalyst after oxidation of hydrocarbons |
| US6288270B1 (en) | 1996-06-24 | 2001-09-11 | Rpc Inc. | Methods for controlling the reaction rate of a hydrocarbon to an acid by making phase-related adjustments |
| US6039902A (en) * | 1996-06-24 | 2000-03-21 | Rpc Inc. | Methods of recycling catalyst in oxidations of hydrocarbons |
| US5877341A (en) * | 1996-08-21 | 1999-03-02 | Twenty-First Century Research Corporation | Methods and devices for controlling the reaction rate of a hydrocarbon to an intermediate oxidation product by pressure drop adjustments |
| US6288274B1 (en) | 1996-08-21 | 2001-09-11 | Rpc Inc. | Methods and devices for controlling the reaction rate and/or reactivity of hydrocarbon to an intermediate oxidation product by adjusting the oxidant consumption rate |
| US6183698B1 (en) | 1996-08-21 | 2001-02-06 | Rpc Inc. | Devices for controlling the reaction rate of a hydrocarbon to an intermediate oxidation product by pressure drop adjustments |
| US5998572A (en) * | 1996-11-12 | 1999-12-07 | Rpc Inc. | Methods and devices for controlling the oxidation of a hydrocarbon to an acid by regulating temperature/conversion relationship in multi-stage arrangements |
| US5824819A (en) * | 1996-12-18 | 1998-10-20 | Twenty-First Century Research Corporation | Methods of preparing an intermediate oxidation product from a hydrocarbon by utilizing an activated initiator |
| WO1998027029A1 (en) * | 1996-12-18 | 1998-06-25 | Twenty-First Century Research Corporation | Methods of preparing an intermediate oxidation product from a hydrocarbon by utilizing an activated initiator |
| US6037491A (en) * | 1997-07-25 | 2000-03-14 | Rpc Inc. | Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent to hydrocarbon ratio |
| US6177053B1 (en) | 1997-09-19 | 2001-01-23 | Rpc Inc. | Devices for removing acetic acid from cyclohexane in the production of adipic acid |
| US5929277A (en) * | 1997-09-19 | 1999-07-27 | Twenty-First Century Research Corporation | Methods of removing acetic acid from cyclohexane in the production of adipic acid |
| US5908589A (en) * | 1997-12-08 | 1999-06-01 | Twenty-First Century Research Corporation | Methods for separating catalyst from oxidation mixtures containing dibasic acids |
| US6232495B1 (en) | 1998-02-09 | 2001-05-15 | Rpc Inc. | Methods for treating cobalt catalyst in oxidation mixtures resulting from oxidation of hydrocarbons to dibasic acids |
| US6326455B2 (en) | 1998-02-09 | 2001-12-04 | Rpc Inc. | Methods for treating cobalt catalyst in oxidation mixtures resulting from oxidation of hydrocarbons to dibasic acids |
| US6129875A (en) * | 1998-02-19 | 2000-10-10 | Rpc Inc. | Process of separating catalyst from oxidation mixtures |
| US6218573B1 (en) | 1998-07-02 | 2001-04-17 | Rpc Inc. | Methods of recovering catalyst in solution in the oxidation of cyclohexane to adipic acid |
| US6433221B1 (en) | 1998-07-02 | 2002-08-13 | Rpc Inc. | Methods of separating catalyst in solution from a reaction mixture produced by oxidation of cyclohexane to adipic acid |
| US6433220B1 (en) | 1998-07-02 | 2002-08-13 | Rpc Inc. | Methods of extracting catalyst from a reaction mixture in the oxidation of cyclohexane to adipic acid |
| US6340420B1 (en) | 1998-07-06 | 2002-01-22 | Rpc Inc. | Methods of treating the oxidation mixture of hydrocarbons to respective dibasic acids |
| US6417128B1 (en) | 1999-04-20 | 2002-07-09 | Rpc, Inc. | Methods and replacing water and cyclohexanone with acetic acid in aqueous solutions of catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| ES251660A1 (en) | 1960-01-01 |
| NL242734A (en) | |
| BE581049A (en) | 1959-11-16 |
| CH377795A (en) | 1964-05-31 |
| DE1114472B (en) | 1961-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB864106A (en) | Preparation of phthalic acids by oxidation | |
| ES482621A1 (en) | Process for the preparation of terephthalic acid by the hydrolysis of intermediate stage crude dimethyl terephthalate | |
| GB1130387A (en) | Ester interchange reactions | |
| GB948687A (en) | Process for producing acrylic acid and acrylic acid methyl ester | |
| GB655074A (en) | An improved process for the preparation of terephthalic acid | |
| GB978172A (en) | Improvements in or relating to the preparation of diesters of phthalic acids | |
| GB980196A (en) | Process for removing acetone and other carbonyl compounds from vinyl acetate | |
| ES453518A1 (en) | Process and apparatus for oxidizing cycloalkanes | |
| ES434949A1 (en) | Process for producing ethylphenols | |
| GB923595A (en) | Improvements in and relating to the production of acrylic esters | |
| JPS54119427A (en) | Preparation of benzenecarboxylic acid | |
| US3012066A (en) | Production of dimethyl terephthalate | |
| JPS54157536A (en) | Esterification process | |
| GB1030847A (en) | Process for the preparation of aromatic carboxylic acids | |
| GB878063A (en) | Improvements in the production of dimethyl terephthalate | |
| GB1429471A (en) | Process for the production of phthalic acids | |
| GB1423042A (en) | Preparation of monomethyl terephthalate and dimethyl tereph thalate | |
| GB1173077A (en) | Production of beta-Lactones | |
| GB892631A (en) | Process for the preparation of aliphatic peracids | |
| US3157691A (en) | Preparation of aromatic polycarboxylated compounds | |
| GB815198A (en) | Improvements in or relating to the production of aromatic acid esters | |
| GB1036159A (en) | Improvements in and relating to the oxidation of butane | |
| GB935610A (en) | 3ªá-amino-pregnane compounds | |
| GB890387A (en) | Improvements in the production of terephthalic acid | |
| ES430305A1 (en) | Cooxidation process for the production of dimethyl terephthalate |