CA1263669A - Procede de preparation de sels alcalins de l'acide trifluoroacetique a l'etat anhydre et cristallise - Google Patents
Procede de preparation de sels alcalins de l'acide trifluoroacetique a l'etat anhydre et cristalliseInfo
- Publication number
- CA1263669A CA1263669A CA000520632A CA520632A CA1263669A CA 1263669 A CA1263669 A CA 1263669A CA 000520632 A CA000520632 A CA 000520632A CA 520632 A CA520632 A CA 520632A CA 1263669 A CA1263669 A CA 1263669A
- Authority
- CA
- Canada
- Prior art keywords
- alkaline
- toluene
- alcohol
- trifluoroacetic acid
- anhydrous
- 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 10
- 159000000011 group IA salts Chemical class 0.000 title claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000004821 distillation Methods 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000013078 crystal Substances 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 11
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 10
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 10
- 238000010533 azeotropic distillation Methods 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 118
- 239000000203 mixture Substances 0.000 claims description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 150000004679 hydroxides Chemical class 0.000 claims description 4
- 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 description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- -1 alkali metal salts Chemical class 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 235000017550 sodium carbonate Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- UYCAUPASBSROMS-UHFFFAOYSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)F UYCAUPASBSROMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical class [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JZVUAOCDNFNSGQ-UHFFFAOYSA-N 7-methoxy-2-phenyl-1h-quinolin-4-one Chemical compound N=1C2=CC(OC)=CC=C2C(O)=CC=1C1=CC=CC=C1 JZVUAOCDNFNSGQ-UHFFFAOYSA-N 0.000 description 1
- TVPCWVGCAIGIDP-UHFFFAOYSA-K FCC(=O)[O-].[Na+].[Na+].[Na+].FCC(=O)[O-].FCC(=O)[O-] Chemical compound FCC(=O)[O-].[Na+].[Na+].[Na+].FCC(=O)[O-].FCC(=O)[O-] TVPCWVGCAIGIDP-UHFFFAOYSA-K 0.000 description 1
- 238000001159 Fisher's combined probability test Methods 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 230000008034 disappearance Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-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
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8515462 | 1985-10-18 | ||
| FR8515462A FR2588863B1 (fr) | 1985-10-18 | 1985-10-18 | Procede de preparation de sels alcalins de l'acide trifluoroacetique a l'etat anhydre et cristallise |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1263669A true CA1263669A (fr) | 1989-12-05 |
Family
ID=9323952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000520632A Expired CA1263669A (fr) | 1985-10-18 | 1986-10-16 | Procede de preparation de sels alcalins de l'acide trifluoroacetique a l'etat anhydre et cristallise |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4760177A (en, 2012) |
| EP (1) | EP0222673B1 (en, 2012) |
| JP (1) | JPS6299340A (en, 2012) |
| AT (1) | ATE51219T1 (en, 2012) |
| CA (1) | CA1263669A (en, 2012) |
| DE (1) | DE3669710D1 (en, 2012) |
| ES (1) | ES2013719B3 (en, 2012) |
| FR (1) | FR2588863B1 (en, 2012) |
| GR (1) | GR3000405T3 (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04136933U (ja) * | 1991-06-14 | 1992-12-21 | 日産車体株式会社 | スライド式シートのシート台座構造 |
| GB2519787B (en) * | 2013-10-30 | 2018-08-29 | Rotam Agrochem Int Co Ltd | Process for the preparation of herbicidal carboxylic acid salts |
| KR20230064618A (ko) * | 2020-09-08 | 2023-05-10 | 다이킨 고교 가부시키가이샤 | 불소 함유 카르복실산염 화합물 |
| CN117623908B (zh) * | 2023-11-28 | 2024-08-02 | 云南弘盛铂业新材料科技有限公司 | 一种制备三氟醋酸钯的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2920086A (en) * | 1955-08-25 | 1960-01-05 | Minnesota Mining & Mfg | Chemical compounds and methods for the preparation thereof |
| GB891858A (en) * | 1958-07-17 | 1962-03-21 | Ghent Sa | Improvements in or relating to oil-soluble soaps of polyvalent metals |
| US3997599A (en) * | 1972-08-31 | 1976-12-14 | The Dow Chemical Company | Extraction of carboxylic acids from dilute aqueous solutions |
| US4049681A (en) * | 1975-12-18 | 1977-09-20 | Akademie Der Wissenschaften Der D D R | Processes for the separation of potassium salts of perfluoroalkanoic acids from aqueous solutions thereof |
-
1985
- 1985-10-18 FR FR8515462A patent/FR2588863B1/fr not_active Expired
-
1986
- 1986-10-16 AT AT86420256T patent/ATE51219T1/de not_active IP Right Cessation
- 1986-10-16 CA CA000520632A patent/CA1263669A/fr not_active Expired
- 1986-10-16 JP JP61244306A patent/JPS6299340A/ja active Granted
- 1986-10-16 EP EP86420256A patent/EP0222673B1/fr not_active Expired - Lifetime
- 1986-10-16 ES ES86420256T patent/ES2013719B3/es not_active Expired - Lifetime
- 1986-10-16 DE DE8686420256T patent/DE3669710D1/de not_active Expired - Fee Related
- 1986-10-20 US US06/920,596 patent/US4760177A/en not_active Expired - Fee Related
-
1990
- 1990-03-23 GR GR90400168T patent/GR3000405T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2013719B3 (es) | 1990-06-01 |
| EP0222673A1 (fr) | 1987-05-20 |
| DE3669710D1 (de) | 1990-04-26 |
| ATE51219T1 (de) | 1990-04-15 |
| FR2588863B1 (fr) | 1987-12-11 |
| GR3000405T3 (en) | 1991-06-28 |
| FR2588863A1 (fr) | 1987-04-24 |
| JPH0210134B2 (en, 2012) | 1990-03-06 |
| JPS6299340A (ja) | 1987-05-08 |
| US4760177A (en) | 1988-07-26 |
| EP0222673B1 (fr) | 1990-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |