DE1225164B - Verfahren zur kontinuierlichen Herstellung von Phthalsaeurediestern - Google Patents
Verfahren zur kontinuierlichen Herstellung von PhthalsaeurediesternInfo
- Publication number
- DE1225164B DE1225164B DEB75154A DEB0075154A DE1225164B DE 1225164 B DE1225164 B DE 1225164B DE B75154 A DEB75154 A DE B75154A DE B0075154 A DEB0075154 A DE B0075154A DE 1225164 B DE1225164 B DE 1225164B
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- parts
- phthalic
- excess
- container
- 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
- 150000005690 diesters Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 8
- 238000010924 continuous production Methods 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 14
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 11
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 238000005886 esterification reaction Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 5
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical class CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- -1 saturated aliphatic alcohols Chemical class 0.000 description 4
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical class CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical class CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- BJQHLKABXJIVAM-BGYRXZFFSA-N 1-o-[(2r)-2-ethylhexyl] 2-o-[(2s)-2-ethylhexyl] benzene-1,2-dicarboxylate Chemical compound CCCC[C@H](CC)COC(=O)C1=CC=CC=C1C(=O)OC[C@H](CC)CCCC BJQHLKABXJIVAM-BGYRXZFFSA-N 0.000 description 1
- IOPYVZVNUXHZCP-UHFFFAOYSA-N 2-(3-ethyloctan-3-yloxycarbonyl)benzoic acid Chemical compound CCCCCC(CC)(CC)OC(=O)C1=CC=CC=C1C(O)=O IOPYVZVNUXHZCP-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N Diethylhexyl phthalate Natural products CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT778269D IT778269A (enrdf_load_stackoverflow) | 1964-01-25 | ||
| DEB75154A DE1225164B (de) | 1964-01-25 | 1964-01-25 | Verfahren zur kontinuierlichen Herstellung von Phthalsaeurediestern |
| CH61565A CH438260A (de) | 1964-01-25 | 1965-01-15 | Verfahren zur kontinuierlichen Herstellung von o-Phthalsäureestern |
| NL6500721A NL142944B (nl) | 1964-01-25 | 1965-01-20 | Werkwijze voor de continue bereiding van o-ftaalzuurdiesters. |
| BE658725D BE658725A (enrdf_load_stackoverflow) | 1964-01-25 | 1965-01-22 | |
| SE89165A SE308514B (enrdf_load_stackoverflow) | 1964-01-25 | 1965-01-22 | |
| GB286765A GB1086132A (en) | 1964-01-25 | 1965-01-22 | Continuous production of o-phthalic esters |
| DK38465A DK112941B (da) | 1964-01-25 | 1965-01-23 | Fremgangsmåde til kontinuerlig fremstilling af o-phthalsyrediestere. |
| JP355965A JPS4935611B1 (enrdf_load_stackoverflow) | 1964-01-25 | 1965-01-25 | |
| FR3153A FR1421995A (fr) | 1964-01-25 | 1965-01-25 | Procédé pour la production en continu d'esters d'acide o-phtalique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB75154A DE1225164B (de) | 1964-01-25 | 1964-01-25 | Verfahren zur kontinuierlichen Herstellung von Phthalsaeurediestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1225164B true DE1225164B (de) | 1966-09-22 |
Family
ID=6978544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB75154A Pending DE1225164B (de) | 1964-01-25 | 1964-01-25 | Verfahren zur kontinuierlichen Herstellung von Phthalsaeurediestern |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4935611B1 (enrdf_load_stackoverflow) |
| BE (1) | BE658725A (enrdf_load_stackoverflow) |
| CH (1) | CH438260A (enrdf_load_stackoverflow) |
| DE (1) | DE1225164B (enrdf_load_stackoverflow) |
| DK (1) | DK112941B (enrdf_load_stackoverflow) |
| FR (1) | FR1421995A (enrdf_load_stackoverflow) |
| GB (1) | GB1086132A (enrdf_load_stackoverflow) |
| IT (1) | IT778269A (enrdf_load_stackoverflow) |
| NL (1) | NL142944B (enrdf_load_stackoverflow) |
| SE (1) | SE308514B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0024505A1 (en) * | 1979-08-27 | 1981-03-11 | Basf Wyandotte Corporation | Method of making mixed esters of phthalic acid |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5324853A (en) * | 1993-01-19 | 1994-06-28 | Exxon Chemical Patents Inc. | Process for the production of plasticizer and polyolesters |
| CN1326829C (zh) * | 2005-09-05 | 2007-07-18 | 吉化集团公司 | 一种邻苯二甲酸二异癸酯的生产方法 |
| CN101427678B (zh) * | 2008-07-05 | 2012-05-09 | 山西农业大学 | 一种植物源杀菌剂及其人工合成方法 |
| CN112955425B (zh) * | 2019-04-04 | 2023-12-26 | 株式会社Lg化学 | 酯类组合物的制备方法和制备系统 |
| US11512166B2 (en) | 2019-04-04 | 2022-11-29 | Lg Chem, Ltd. | Method and system for manufacturing ester-based composition |
| KR102797150B1 (ko) * | 2020-11-17 | 2025-04-21 | 주식회사 엘지화학 | 디에스터계 물질의 제조방법 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE631783C (de) * | 1931-12-10 | 1936-06-26 | Carbide & Carbon Chem Corp | Verfahren zur Herstellung gemischter Ester |
| DE844146C (de) * | 1947-10-06 | 1952-07-17 | Shell Refining & Marketing Com | Verfahren zur Herstellung neutraler Phthalsaeureester |
-
0
- IT IT778269D patent/IT778269A/it unknown
-
1964
- 1964-01-25 DE DEB75154A patent/DE1225164B/de active Pending
-
1965
- 1965-01-15 CH CH61565A patent/CH438260A/de unknown
- 1965-01-20 NL NL6500721A patent/NL142944B/xx unknown
- 1965-01-22 BE BE658725D patent/BE658725A/xx unknown
- 1965-01-22 SE SE89165A patent/SE308514B/xx unknown
- 1965-01-22 GB GB286765A patent/GB1086132A/en not_active Expired
- 1965-01-23 DK DK38465A patent/DK112941B/da unknown
- 1965-01-25 FR FR3153A patent/FR1421995A/fr not_active Expired
- 1965-01-25 JP JP355965A patent/JPS4935611B1/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE631783C (de) * | 1931-12-10 | 1936-06-26 | Carbide & Carbon Chem Corp | Verfahren zur Herstellung gemischter Ester |
| DE844146C (de) * | 1947-10-06 | 1952-07-17 | Shell Refining & Marketing Com | Verfahren zur Herstellung neutraler Phthalsaeureester |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0024505A1 (en) * | 1979-08-27 | 1981-03-11 | Basf Wyandotte Corporation | Method of making mixed esters of phthalic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| BE658725A (enrdf_load_stackoverflow) | 1965-07-22 |
| CH438260A (de) | 1967-06-30 |
| GB1086132A (en) | 1967-10-04 |
| JPS4935611B1 (enrdf_load_stackoverflow) | 1974-09-25 |
| IT778269A (enrdf_load_stackoverflow) | |
| FR1421995A (fr) | 1965-12-17 |
| DK112941B (da) | 1969-02-03 |
| NL6500721A (enrdf_load_stackoverflow) | 1965-07-26 |
| NL142944B (nl) | 1974-08-15 |
| SE308514B (enrdf_load_stackoverflow) | 1969-02-17 |
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