DE2837690C2 - - Google Patents
Info
- Publication number
- DE2837690C2 DE2837690C2 DE2837690A DE2837690A DE2837690C2 DE 2837690 C2 DE2837690 C2 DE 2837690C2 DE 2837690 A DE2837690 A DE 2837690A DE 2837690 A DE2837690 A DE 2837690A DE 2837690 C2 DE2837690 C2 DE 2837690C2
- Authority
- DE
- Germany
- Prior art keywords
- fluorination
- parts
- product
- hydrogen fluoride
- catalyst
- 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
- 238000003682 fluorination reaction Methods 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 41
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 26
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 24
- 239000007791 liquid phase Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 9
- XZQYTGKSBZGQMO-UHFFFAOYSA-I rhenium pentachloride Chemical compound Cl[Re](Cl)(Cl)(Cl)Cl XZQYTGKSBZGQMO-UHFFFAOYSA-I 0.000 claims description 6
- 229910015227 MoCl3 Inorganic materials 0.000 claims description 4
- ZSSVQAGPXAAOPV-UHFFFAOYSA-K molybdenum trichloride Chemical compound Cl[Mo](Cl)Cl ZSSVQAGPXAAOPV-UHFFFAOYSA-K 0.000 claims description 4
- 229910015218 MoCl4 Inorganic materials 0.000 claims description 3
- 229910019804 NbCl5 Inorganic materials 0.000 claims description 3
- 229910004537 TaCl5 Inorganic materials 0.000 claims description 3
- OYMJNIHGVDEDFX-UHFFFAOYSA-J molybdenum tetrachloride Chemical compound Cl[Mo](Cl)(Cl)Cl OYMJNIHGVDEDFX-UHFFFAOYSA-J 0.000 claims description 3
- YHBDIEWMOMLKOO-UHFFFAOYSA-I pentachloroniobium Chemical compound Cl[Nb](Cl)(Cl)(Cl)Cl YHBDIEWMOMLKOO-UHFFFAOYSA-I 0.000 claims description 3
- OEIMLTQPLAGXMX-UHFFFAOYSA-I tantalum(v) chloride Chemical compound Cl[Ta](Cl)(Cl)(Cl)Cl OEIMLTQPLAGXMX-UHFFFAOYSA-I 0.000 claims description 3
- 229910015255 MoF6 Inorganic materials 0.000 claims description 2
- 229910015686 MoOCl4 Inorganic materials 0.000 claims description 2
- 229910004546 TaF5 Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- ASLHVQCNFUOEEN-UHFFFAOYSA-N dioxomolybdenum;dihydrochloride Chemical compound Cl.Cl.O=[Mo]=O ASLHVQCNFUOEEN-UHFFFAOYSA-N 0.000 claims description 2
- RLCOZMCCEKDUPY-UHFFFAOYSA-H molybdenum hexafluoride Chemical compound F[Mo](F)(F)(F)(F)F RLCOZMCCEKDUPY-UHFFFAOYSA-H 0.000 claims description 2
- SFPKXFFNQYDGAH-UHFFFAOYSA-N oxomolybdenum;tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.[Mo]=O SFPKXFFNQYDGAH-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 claims description 2
- 150000003613 toluenes Chemical class 0.000 claims description 2
- 239000000047 product Substances 0.000 description 27
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 18
- 239000012808 vapor phase Substances 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 239000007789 gas Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- -1 Halocarbon compound Chemical class 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LVZPKYYPPLUECL-UHFFFAOYSA-N 1-chloro-4-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1 LVZPKYYPPLUECL-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical class Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000012025 fluorinating agent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GKGPLSQWIBJJPC-UHFFFAOYSA-N 1,2-dichloro-3-(trichloromethyl)benzene Chemical compound ClC1=CC=CC(C(Cl)(Cl)Cl)=C1Cl GKGPLSQWIBJJPC-UHFFFAOYSA-N 0.000 description 1
- DGRVQOKCSKDWIH-UHFFFAOYSA-N 1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Cl DGRVQOKCSKDWIH-UHFFFAOYSA-N 0.000 description 1
- 108010071778 Benzoylformate decarboxylase Proteins 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82984777A | 1977-09-01 | 1977-09-01 | |
| US05/829,846 US4129602A (en) | 1977-09-01 | 1977-09-01 | Liquid phase fluorination process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2837690A1 DE2837690A1 (de) | 1979-03-15 |
| DE2837690C2 true DE2837690C2 (enEXAMPLES) | 1988-03-17 |
Family
ID=27125304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782837690 Granted DE2837690A1 (de) | 1977-09-01 | 1978-08-29 | Fluorierungsverfahren in fluessiger phase |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5446726A (enEXAMPLES) |
| BR (1) | BR7805684A (enEXAMPLES) |
| CA (1) | CA1108651A (enEXAMPLES) |
| DE (1) | DE2837690A1 (enEXAMPLES) |
| FR (1) | FR2401892A1 (enEXAMPLES) |
| GB (1) | GB2003474B (enEXAMPLES) |
| IT (1) | IT1202766B (enEXAMPLES) |
| NL (1) | NL7808902A (enEXAMPLES) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7698217B2 (ja) * | 2022-08-02 | 2025-06-25 | ダイキン工業株式会社 | フッ素含有芳香族化合物の製造方法 |
| CN117964597A (zh) * | 2024-01-24 | 2024-05-03 | 景德镇富祥生命科技有限公司 | 一种氟代碳酸乙烯酯的制备方法 |
| CN117964490B (zh) | 2024-01-24 | 2024-12-20 | 景德镇富祥生命科技有限公司 | 一种三氟甲基芳香化合物的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1967244A (en) * | 1932-08-31 | 1934-07-24 | Kinetic Chemicals Inc | Production of organic fluorine compounds |
| US3258500A (en) * | 1959-08-17 | 1966-06-28 | Du Pont | Process for fluorinating halohydro-carbons |
| US3859372A (en) * | 1969-12-03 | 1975-01-07 | Hooker Chemicals Plastics Corp | Process for the preparation of organic fluorine compounds |
| US4098832A (en) * | 1976-11-01 | 1978-07-04 | Hooker Chemicals & Plastics Corp. | Fluorination process catalysed by molybdenum pentachloride |
-
1978
- 1978-08-24 CA CA310,012A patent/CA1108651A/en not_active Expired
- 1978-08-29 DE DE19782837690 patent/DE2837690A1/de active Granted
- 1978-08-30 JP JP10616578A patent/JPS5446726A/ja active Granted
- 1978-08-30 GB GB7834925A patent/GB2003474B/en not_active Expired
- 1978-08-30 FR FR7825044A patent/FR2401892A1/fr active Granted
- 1978-08-30 NL NL7808902A patent/NL7808902A/xx not_active Application Discontinuation
- 1978-08-31 BR BR7805684A patent/BR7805684A/pt unknown
- 1978-09-01 IT IT27262/78A patent/IT1202766B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB2003474B (en) | 1982-03-17 |
| BR7805684A (pt) | 1979-04-24 |
| DE2837690A1 (de) | 1979-03-15 |
| FR2401892A1 (fr) | 1979-03-30 |
| NL7808902A (nl) | 1979-03-05 |
| GB2003474A (en) | 1979-03-14 |
| IT1202766B (it) | 1989-02-09 |
| JPS5446726A (en) | 1979-04-12 |
| CA1108651A (en) | 1981-09-08 |
| IT7827262A0 (it) | 1978-09-01 |
| JPS6334128B2 (enEXAMPLES) | 1988-07-08 |
| FR2401892B1 (enEXAMPLES) | 1984-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: OCCIDENTAL CHEMICAL CORP. (EINE GESELLSCHAFT N.D.G |
|
| 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 |