IES86989B2 - Medicine intermediates terephthalic acid synthesis method - Google Patents
Medicine intermediates terephthalic acid synthesis method Download PDFInfo
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- IES86989B2 IES86989B2 IES20180077A IES20180077A IES86989B2 IE S86989 B2 IES86989 B2 IE S86989B2 IE S20180077 A IES20180077 A IE S20180077A IE S20180077 A IES20180077 A IE S20180077A IE S86989 B2 IES86989 B2 IE S86989B2
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- IE
- Ireland
- Prior art keywords
- solution
- terephthalic acid
- mass fraction
- mol
- temperature
- Prior art date
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000000543 intermediate Substances 0.000 title claims abstract description 10
- 239000003814 drug Substances 0.000 title claims abstract description 9
- 238000001308 synthesis method Methods 0.000 title claims abstract description 9
- 229940079593 drug Drugs 0.000 title claims abstract description 6
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 claims abstract description 16
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims abstract description 12
- -1 4-ethyl-5-amino-benzyl Chemical group 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 claims abstract description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000018044 dehydration Effects 0.000 claims abstract description 6
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 6
- 239000010936 titanium Substances 0.000 claims abstract description 6
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000000243 solution Substances 0.000 description 36
- 239000004014 plasticizer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 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
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
Medicine intermediates terephthalic acid synthesis method, comprises the following steps: 2 mol 4-ethyl-5-amino-benzyl alcohol and 4-5 mol 2,5-dimethy1-2,5-hexanediol were added to the reaction vessel, raised the temperature of the solution to 60-67 V, controlled the stirring speed at 170-190 rpm, kept for 130-170 min, then add 3-4 mol dicyldiphenyl titanium in 6 to 9 times, raised the temperature of the solution to 80-86°C, kept for 70-90 min, precipitated solid, filtered, the solid washed with potassium bromide solution, washed with dipentyl ether solution, 4-heptanone solution, reduced solution temperature to 3-6°C , recrystallized in diisopropyl ether solution, dehydrated with dehydration, got the finished product terephthalic acid.
Description
Medicine intermediates terephthalic acid synthesis method
FIELD OF THE INVENTION
The present invention relates to medicine intermediates terephthalic acid synthesis method.
GENERAL BACKGROUND
Terephthalic acid is used to produce polyethylene terephthalate. Another important application of terephthalic acid is the production of plasticizers, which includes two categories: one is the dioctyl terephthalate, which is the product of terephthalic acid and 2-ethylhexanol esterification reaction, it is a high flash point, high specific resistance of high-quality plasticizer, especially for heat and insulation requirements of the production of high cable material; the second is a polyester plasticizer, it is a terephthalic acid and polyols, such as diethylene glycol, triethylene glycol, glycerol, propylene glycol, butanediol. Such as the product of the esterification polycondensation reaction, the relative molecular mass is generally between 1000 and 4000, and the relative molecular mass ratio of the polyester as a plasticizer is much smaller than that of the polyester for chemical and plastic packaging. However, most of the existing synthetic methods are using p-phenylethanone and potassium permanganate as reactant, it is complicated and the final yield is not very high. Therefore, it is necessary to propose a new synthetic method for further improving the quality and yield of the product and reducing the byproduct content, it has important economic significance.
SUMMARY
The purpose of the present invention is to provide medicine intermediates terephthalic acid synthesis method, comprises the following steps:
(i) 2 mol 4-ethyl-5-amino-benzyl alcohol and 4-5 mol
2,5-dimethyl-2,5-hexanediol were added to the reaction vessel, raised the temperature of the solution to 60-67 “C, controlled the stirring speed at 170-190 rpm, kept for 130-170 min, then add 3-4 mol dicyldiphenyl titanium in 6 to 9 times, raised the temperature of the solution to 80-86 °C, kept for 70-90 min, precipitated solid, filtered, the solid washed with potassium bromide solution, washed with dipentyl ether solution,
4-heptanone solution, reduced solution temperature to 3-6 °C, recrystallized in diisopropyl ether solution, dehydrated with dehydration, got the finished product terephthalic acid; wherein, the 2,5-dimethyl-2,5-hexanediol solution has a mass fraction of 80-85% as described in step (i), and the mass fraction of the potassium solut ion in step is 40-45%, the mass fraction of the dipentyl ether solution in step (i) is 75-83%, the mass fraction of the 4-heptanone solution in step (i) is 85-90%, the mass fraction of the diisopropyl ether solution is 92-96%.
Throughout the reaction process can be the following reaction formula:
Advantage of the present invention is that: reducing intermediate links reaction, decreasing the reaction time and improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated:
medicine intermediates terephthalic acid synthesis method.
Embodiment 1 mol 4-ethyl-5-amino-benzyl alcohol, 4 mol a 2,5-dimethyl-2,5-hexanediol solution with a mass fraction of 80% were added to the reaction vessel, and the temperature of the solution was raised to 60 °C, controlled the stirring speed at 170 rpm, kept it for 130 min, then added 3 mol dicyldiphenyl titanium in 6 times, raised the temperature of the solution to 80 °C for 70 min, precipitated solid, filter, filter cake washed with potassium bromide solution with mass fraction of 40%, washed with dipentyl ether solution with mass fraction of 75%, and washed with 4-heptanone solution with mass fraction of 85%, the solution temperature was reduced to 3 °C, recrystallized in diisopropyl ether solution with mass fraction of 92%, dehydrated with dehydration, got the finished terephthalic acid 288.36g, yield 89%.
Embodiment 2 mol 4-ethyl-5-amino-benzyl alcohol, 4.5 mol a 2,5-dimethyl-2,5-hexanediol solution with a mass fraction of 82% were added to the reaction vessel, and the temperature of the solution was raised to 63 °C, controlled the stirring speed at 180 rpm, kept it for 150 min, then added 3.5 mol dicyldiphenyl titanium in 7 steps, raised the temperature of the solution to 83 °C for 80 min, precipitated solid, filter, filter cake washed with potassium bromide solution with mass fraction of 42%, washed with dipentyl ether solution with mass fraction of 80%, and washed with 4-heptanone solution with mass fraction of 87%, the solution temperature was reduced to 4 °C, recrystallized in diisopropyl ether solution with mass fraction of 94%, dehydrated with dehydration, got the finished terephthalic acid 294.84g, yield 91%.
Embodiment 3 mol 4-ethyl-5-amino-benzyl alcohol, 5 mol a 2,5-dimethyl-2,5-hexanediol solution with a mass fraction of 85% were added to the reaction vessel, and the temperature of the solution was raised to 67 °C, controlled the stirring speed at 190 rpm, kept it for 170 min, then added 4 mol dicyldiphenyl titanium in 9 times, raised the temperature of the solution to 86 C for 90 min, precipitated solid, filter, filter cake washed with potassium bromide solution with mass fraction of 45%, washed with dipentyl ether solution with mass fraction of 83%, and washed with 4-heptanone solution with mass fraction of 90%, the solution temperature was reduced to 6°C, recrystallized in diisopropyl ether solution with mass fraction of 96%, dehydrated with dehydration, got the finished terephthalic acid 301,32g, yield 93%.
Claims (3)
1. Medicine intermediates terephthalic acid synthesis method, comprises the following steps: (i) 2 mol 4-ethyl-5-amino-benzyl alcohol and 4-5 mol 5 2,5-dimethyl-2,5-hexanediol were added to the reaction vessel, raised the temperature of the solution to 60-67 °C, controlled the stirring speed at 170-190 rpm, kept for 130-170 min, then add 3-4 mol dicyldiphenyl titanium in 6 to 9 times, raised the temperature of the solution to 80-86 °C, kept for 70-90 min, precipitated solid, filtered, the solid washed with potassium bromide solution, washed with dipentyl 10 ether solution, 4-heptanone solution, reduced solution temperature to 3-6 °C, recrystallized in diisopropyl ether solution, dehydrated with dehydration, got the finished product terephthalic acid; wherein, the 2,5-dimethyI-2,5-hexanediol solution has a mass fraction of 80-85% as described in step (i), and the mass fraction of the potassium solution in step is 40-45%, the mass fraction of the dipentyl ether solution 15 m step (i) is 75-83%.
2. Medicine intermediates terephthalic acid synthesis method according to claim 1 wherein the mass fraction of the 4-heptanone solution in step (i) is 85-90%. 20
3. Medicine intermediates terephthalic acid synthesis method according to claim 1 wherein the mass fraction of the diisopropyl ether solution is 92-96%.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710213308.8A CN108238899A (en) | 2017-04-02 | 2017-04-02 | A kind of synthetic method of medicine intermediate terephthalic acid (TPA) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IES20180077A2 IES20180077A2 (en) | 2019-04-03 |
| IES86989B2 true IES86989B2 (en) | 2019-05-01 |
Family
ID=58744574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IES20180077A IES86989B2 (en) | 2017-04-02 | 2018-03-27 | Medicine intermediates terephthalic acid synthesis method |
Country Status (4)
| Country | Link |
|---|---|
| CN (1) | CN108238899A (en) |
| AU (1) | AU2018100411A4 (en) |
| GB (1) | GB201705835D0 (en) |
| IE (1) | IES86989B2 (en) |
-
2017
- 2017-04-02 CN CN201710213308.8A patent/CN108238899A/en active Pending
- 2017-04-11 GB GBGB1705835.5A patent/GB201705835D0/en not_active Ceased
-
2018
- 2018-03-27 IE IES20180077A patent/IES86989B2/en unknown
- 2018-03-31 AU AU2018100411A patent/AU2018100411A4/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| GB201705835D0 (en) | 2017-05-24 |
| CN108238899A (en) | 2018-07-03 |
| IES20180077A2 (en) | 2019-04-03 |
| AU2018100411A4 (en) | 2018-05-10 |
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