DE2128942A1 - - Google Patents
Info
- Publication number
- DE2128942A1 DE2128942A1 DE19712128942 DE2128942A DE2128942A1 DE 2128942 A1 DE2128942 A1 DE 2128942A1 DE 19712128942 DE19712128942 DE 19712128942 DE 2128942 A DE2128942 A DE 2128942A DE 2128942 A1 DE2128942 A1 DE 2128942A1
- Authority
- DE
- Germany
- Prior art keywords
- column
- steam
- acid
- ester
- alcohol
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000012535 impurity Substances 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001256 steam distillation Methods 0.000 claims description 6
- 210000000056 organ Anatomy 0.000 claims description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 150000003022 phthalic acids Chemical class 0.000 claims description 2
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- 239000008031 plastic plasticizer Substances 0.000 claims 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims 1
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical class CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 claims 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- -1 for example Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7028288A FR2098915A5 (enrdf_load_stackoverflow) | 1970-07-24 | 1970-07-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2128942A1 true DE2128942A1 (enrdf_load_stackoverflow) | 1972-11-30 |
| DE2128942B2 DE2128942B2 (de) | 1976-11-18 |
Family
ID=9059564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712128942 Pending DE2128942B2 (de) | 1970-07-24 | 1971-06-11 | Verfahren zum reinigen hochsiedender dicarbonsaeurediester |
Country Status (17)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3336601A1 (de) * | 1983-10-07 | 1985-04-25 | Sven-Gunnar Dipl.-Ing. Uetliburg Jacobson | Langgestreckte kardierplatte |
| CN107311860A (zh) * | 2017-06-22 | 2017-11-03 | 江苏飞翔化工股份有限公司 | 一种1,2‑环己烷二甲酸二元酯的制备方法 |
| CN109678712A (zh) * | 2019-01-29 | 2019-04-26 | 安徽力天环保科技股份有限公司 | 一种邻苯二甲酸二辛酯制备装置及其制备方法 |
| WO2020173818A1 (de) * | 2019-02-25 | 2020-09-03 | Basf Se | Verfahren zur aufarbeitung von benzolpolycarbonsäureestern und deren verwendung zur herstellung von cyclohexanpolycarbonsäureestern |
-
1970
- 1970-07-24 FR FR7028288A patent/FR2098915A5/fr not_active Expired
-
1971
- 1971-05-26 NO NO197771A patent/NO135981C/no unknown
- 1971-05-27 NL NL7107296A patent/NL7107296A/xx unknown
- 1971-06-11 DE DE19712128942 patent/DE2128942B2/de active Pending
- 1971-06-18 JP JP46043848A patent/JPS5117521B1/ja active Pending
- 1971-06-30 GB GB3076071A patent/GB1302146A/en not_active Expired
- 1971-07-14 FI FI200671A patent/FI52933C/fi active
- 1971-07-15 CA CA118,361A patent/CA960605A/en not_active Expired
- 1971-07-16 AT AT619271A patent/AT305311B/de not_active IP Right Cessation
- 1971-07-19 ES ES393411A patent/ES393411A1/es not_active Expired
- 1971-07-20 CS CS534571A patent/CS174821B2/cs unknown
- 1971-07-20 CH CH1065971A patent/CH540875A/fr not_active IP Right Cessation
- 1971-07-21 PL PL14958171A patent/PL81830B1/pl unknown
- 1971-07-21 RO RO6773571A patent/RO63616A/ro unknown
- 1971-07-22 HU HUME001401 patent/HU164794B/hu unknown
- 1971-07-23 BE BE770450A patent/BE770450A/xx not_active IP Right Cessation
- 1971-07-23 SE SE951871A patent/SE387627B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH540875A (fr) | 1973-08-31 |
| CS174821B2 (enrdf_load_stackoverflow) | 1977-04-29 |
| ES393411A1 (es) | 1974-09-16 |
| SE387627B (sv) | 1976-09-13 |
| BE770450A (fr) | 1972-01-24 |
| FI52933B (enrdf_load_stackoverflow) | 1977-09-30 |
| GB1302146A (enrdf_load_stackoverflow) | 1973-01-04 |
| NL7107296A (enrdf_load_stackoverflow) | 1972-01-26 |
| RO63616A (fr) | 1978-08-15 |
| FI52933C (enrdf_load_stackoverflow) | 1978-01-10 |
| NO135981B (enrdf_load_stackoverflow) | 1977-03-28 |
| FR2098915A5 (enrdf_load_stackoverflow) | 1972-03-10 |
| NO135981C (enrdf_load_stackoverflow) | 1977-07-06 |
| PL81830B1 (enrdf_load_stackoverflow) | 1975-10-31 |
| HU164794B (enrdf_load_stackoverflow) | 1974-04-11 |
| JPS5117521B1 (enrdf_load_stackoverflow) | 1976-06-03 |
| DE2128942B2 (de) | 1976-11-18 |
| AT305311B (de) | 1973-02-26 |
| CA960605A (en) | 1975-01-07 |
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