DE3445416A1 - Verfahren zur herstellung von 2,4,5-trichlorphenoxyessigsaeure - Google Patents
Verfahren zur herstellung von 2,4,5-trichlorphenoxyessigsaeureInfo
- Publication number
- DE3445416A1 DE3445416A1 DE19843445416 DE3445416A DE3445416A1 DE 3445416 A1 DE3445416 A1 DE 3445416A1 DE 19843445416 DE19843445416 DE 19843445416 DE 3445416 A DE3445416 A DE 3445416A DE 3445416 A1 DE3445416 A1 DE 3445416A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- approx
- tcdd
- trichlorophenolate
- solvent
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 claims abstract description 15
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims abstract description 13
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012452 mother liquor Substances 0.000 claims abstract description 8
- KWFOMJTYKROHLX-UHFFFAOYSA-M sodium;2,4,5-trichlorophenolate Chemical compound [Na+].[O-]C1=CC(Cl)=C(Cl)C=C1Cl KWFOMJTYKROHLX-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 5
- 238000009833 condensation Methods 0.000 claims description 11
- 230000005494 condensation Effects 0.000 claims description 11
- 239000002351 wastewater Substances 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 4
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- NGWKGSCSHDHHAJ-YPFQVHCOSA-N Liquoric acid Chemical compound C1C[C@H](O)C(C)(C)C2CC[C@@]3(C)[C@]4(C)C[C@H]5O[C@@H]([C@](C6)(C)C(O)=O)C[C@@]5(C)[C@@H]6C4=CC(=O)C3[C@]21C NGWKGSCSHDHHAJ-YPFQVHCOSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- WPQWITCZLCIZNZ-UHFFFAOYSA-N sodium;2,4,5-trichlorophenol Chemical compound [Na].OC1=CC(Cl)=C(Cl)C=C1Cl WPQWITCZLCIZNZ-UHFFFAOYSA-N 0.000 claims 1
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000002156 mixing Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000003809 water extraction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- -1 2,4,5-trichlorophenoxy Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- UBDHSURDYAETAL-UHFFFAOYSA-N 8-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 UBDHSURDYAETAL-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000004065 wastewater treatment Methods 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843445416 DE3445416A1 (de) | 1984-12-13 | 1984-12-13 | Verfahren zur herstellung von 2,4,5-trichlorphenoxyessigsaeure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843445416 DE3445416A1 (de) | 1984-12-13 | 1984-12-13 | Verfahren zur herstellung von 2,4,5-trichlorphenoxyessigsaeure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3445416A1 true DE3445416A1 (de) | 1986-06-19 |
| DE3445416C2 DE3445416C2 (enrdf_load_stackoverflow) | 1990-03-15 |
Family
ID=6252635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843445416 Granted DE3445416A1 (de) | 1984-12-13 | 1984-12-13 | Verfahren zur herstellung von 2,4,5-trichlorphenoxyessigsaeure |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3445416A1 (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4345097A (en) * | 1980-01-21 | 1982-08-17 | Vertac Chemical Corporation | Chlorination of phenols and phenoxyacetic acids with sulfuryl chloride |
| US4346248A (en) * | 1980-02-20 | 1982-08-24 | Vertac Chemical Corporation | Preparation of 2,4,5-trichlorophenol and 2,4,5-trichlorophenoxyacetic acid free of 2,3,7,8-tetrachloro-dibenzo-p-dioxin contamination |
-
1984
- 1984-12-13 DE DE19843445416 patent/DE3445416A1/de active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4345097A (en) * | 1980-01-21 | 1982-08-17 | Vertac Chemical Corporation | Chlorination of phenols and phenoxyacetic acids with sulfuryl chloride |
| US4346248A (en) * | 1980-02-20 | 1982-08-24 | Vertac Chemical Corporation | Preparation of 2,4,5-trichlorophenol and 2,4,5-trichlorophenoxyacetic acid free of 2,3,7,8-tetrachloro-dibenzo-p-dioxin contamination |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3445416C2 (enrdf_load_stackoverflow) | 1990-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: FALENSKI, JOACHIM, 8390 PASSAU, DE |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |