CS195273B2 - Method of producing monohalogene acylhalogenides by halogenation of ketenes - Google Patents
Method of producing monohalogene acylhalogenides by halogenation of ketenes Download PDFInfo
- Publication number
- CS195273B2 CS195273B2 CS745034A CS503474A CS195273B2 CS 195273 B2 CS195273 B2 CS 195273B2 CS 745034 A CS745034 A CS 745034A CS 503474 A CS503474 A CS 503474A CS 195273 B2 CS195273 B2 CS 195273B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- reaction
- solvent
- formula
- optionally substituted
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- 230000026030 halogenation Effects 0.000 title claims description 10
- 238000005658 halogenation reaction Methods 0.000 title claims description 10
- 150000002561 ketenes Chemical class 0.000 title abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 58
- 150000004820 halides Chemical class 0.000 claims abstract description 24
- 125000001174 sulfone group Chemical group 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000003457 sulfones Chemical class 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- -1 phosphorous ester Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 abstract description 14
- 230000015572 biosynthetic process Effects 0.000 abstract description 10
- 150000001266 acyl halides Chemical class 0.000 abstract description 4
- 239000007791 liquid phase Substances 0.000 abstract description 3
- 230000002363 herbicidal effect Effects 0.000 abstract description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000005691 triesters Chemical class 0.000 abstract 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical class ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 239000012346 acetyl chloride Chemical class 0.000 description 8
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 8
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical class CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical class N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical class CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 3
- HRSFRSLKOPFWMZ-UHFFFAOYSA-N (3,4,5-trifluorophenyl)methanol Chemical compound OCC1=CC(F)=C(F)C(F)=C1 HRSFRSLKOPFWMZ-UHFFFAOYSA-N 0.000 description 2
- VPCWSGCHQIRQHR-UHFFFAOYSA-N 2,2-diiodoacetyl chloride Chemical compound ClC(=O)C(I)I VPCWSGCHQIRQHR-UHFFFAOYSA-N 0.000 description 2
- BSVMPWANOMFSPR-UHFFFAOYSA-N 2-iodoacetyl chloride Chemical compound ClC(=O)CI BSVMPWANOMFSPR-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- GMMWYLWUQMPFBF-UHFFFAOYSA-N [Cl].[Cl].[Cl] Chemical compound [Cl].[Cl].[Cl] GMMWYLWUQMPFBF-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical class C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical compound CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical class ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 description 1
- JEXYCADTAFPULN-UHFFFAOYSA-N 1-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCC JEXYCADTAFPULN-UHFFFAOYSA-N 0.000 description 1
- IPKCHUGFUGHNRZ-UHFFFAOYSA-N 2,2-dichloropropanoyl chloride Chemical compound CC(Cl)(Cl)C(Cl)=O IPKCHUGFUGHNRZ-UHFFFAOYSA-N 0.000 description 1
- FGEAOSXMQZWHIQ-UHFFFAOYSA-N 2-chloro-2-phenylacetyl chloride Chemical compound ClC(=O)C(Cl)C1=CC=CC=C1 FGEAOSXMQZWHIQ-UHFFFAOYSA-N 0.000 description 1
- JEQDSBVHLKBEIZ-UHFFFAOYSA-N 2-chloropropanoyl chloride Chemical compound CC(Cl)C(Cl)=O JEQDSBVHLKBEIZ-UHFFFAOYSA-N 0.000 description 1
- IUVGGESEBFJHPK-UHFFFAOYSA-N 2-ethoxy-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound CCOP1(=O)OCCO1 IUVGGESEBFJHPK-UHFFFAOYSA-N 0.000 description 1
- NWXORMWIWGSYJJ-UHFFFAOYSA-N 2-ethylbut-1-en-1-one Chemical compound CCC(CC)=C=O NWXORMWIWGSYJJ-UHFFFAOYSA-N 0.000 description 1
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 1
- NIJIVTSERLDNCD-UHFFFAOYSA-N 2-methylpropylsulfonylcyclohexane Chemical compound C(C(C)C)S(=O)(=O)C1CCCCC1 NIJIVTSERLDNCD-UHFFFAOYSA-N 0.000 description 1
- RZGZTQYTDRQOEY-UHFFFAOYSA-N 2-phenylethenone Chemical compound O=C=CC1=CC=CC=C1 RZGZTQYTDRQOEY-UHFFFAOYSA-N 0.000 description 1
- SPJQDMKTFSPPLO-UHFFFAOYSA-N 2-tert-butylsulfonyl-2-methylpropane Chemical compound CC(C)(C)S(=O)(=O)C(C)(C)C SPJQDMKTFSPPLO-UHFFFAOYSA-N 0.000 description 1
- 101100126625 Caenorhabditis elegans itr-1 gene Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- JSEMCPMTAXQTJN-UHFFFAOYSA-N but-1-en-1-one Chemical compound CCC=C=O JSEMCPMTAXQTJN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- IHPUVAUZMHQZSK-UHFFFAOYSA-N diethyl propyl phosphate Chemical compound CCCOP(=O)(OCC)OCC IHPUVAUZMHQZSK-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZWJPCOALBPMBIC-UHFFFAOYSA-N diphenylketene Chemical compound C=1C=CC=CC=1C(=C=O)C1=CC=CC=C1 ZWJPCOALBPMBIC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- VNPZMCWUXKJOHF-UHFFFAOYSA-N ethene;methyl acetate Chemical compound C=C.COC(C)=O VNPZMCWUXKJOHF-UHFFFAOYSA-N 0.000 description 1
- CCCGCQZBATVVDB-UHFFFAOYSA-N ethenone Chemical compound C=C=O.C=C=O CCCGCQZBATVVDB-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- BOSMZFBHAYFUBJ-UHFFFAOYSA-N tris(4-methylphenyl) phosphate Chemical compound C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 BOSMZFBHAYFUBJ-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
- C07C51/58—Preparation of carboxylic acid halides
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US379899A US3883589A (en) | 1973-07-16 | 1973-07-16 | Preparation of monohaloacyl halides |
| US380785A US3882173A (en) | 1973-07-19 | 1973-07-19 | Preparation of monohaloacyl halides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195273B2 true CS195273B2 (en) | 1980-01-31 |
Family
ID=27008817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS745034A CS195273B2 (en) | 1973-07-16 | 1974-07-15 | Method of producing monohalogene acylhalogenides by halogenation of ketenes |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5537978B2 (ro) |
| BG (2) | BG24793A3 (ro) |
| BR (1) | BR7405806D0 (ro) |
| CA (1) | CA1024525A (ro) |
| CH (1) | CH614689A5 (ro) |
| CS (1) | CS195273B2 (ro) |
| DD (1) | DD112120A5 (ro) |
| DE (1) | DE2433943C3 (ro) |
| DK (1) | DK152647C (ro) |
| EG (1) | EG11430A (ro) |
| FR (1) | FR2237874B1 (ro) |
| GB (1) | GB1425304A (ro) |
| HU (1) | HU169590B (ro) |
| IL (1) | IL45270A (ro) |
| IT (1) | IT1017169B (ro) |
| NL (1) | NL181578C (ro) |
| RO (1) | RO73277A (ro) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789466A (fr) * | 1971-09-30 | 1973-03-29 | Monsanto Co | Procede de preparation d'halogenures de monohaloacetyles |
| BE789467A (fr) * | 1971-09-30 | 1973-03-29 | Monsanto Co | Procede de preparation d'halogenures de monohaloacetyles |
-
1974
- 1974-07-12 RO RO7479464A patent/RO73277A/ro unknown
- 1974-07-12 NL NLAANVRAGE7409443,A patent/NL181578C/xx not_active IP Right Cessation
- 1974-07-15 FR FR7424488A patent/FR2237874B1/fr not_active Expired
- 1974-07-15 DK DK379474A patent/DK152647C/da not_active IP Right Cessation
- 1974-07-15 DD DD179918A patent/DD112120A5/xx unknown
- 1974-07-15 CS CS745034A patent/CS195273B2/cs unknown
- 1974-07-15 IT IT25187/74A patent/IT1017169B/it active
- 1974-07-15 CA CA204,791A patent/CA1024525A/en not_active Expired
- 1974-07-15 CH CH974874A patent/CH614689A5/xx not_active IP Right Cessation
- 1974-07-15 HU HUMO907A patent/HU169590B/hu unknown
- 1974-07-15 BG BG029921A patent/BG24793A3/xx unknown
- 1974-07-15 JP JP8029774A patent/JPS5537978B2/ja not_active Expired
- 1974-07-15 GB GB3122774A patent/GB1425304A/en not_active Expired
- 1974-07-15 BR BR5806/74A patent/BR7405806D0/pt unknown
- 1974-07-15 IL IL45270A patent/IL45270A/xx unknown
- 1974-07-15 BG BG027243A patent/BG21205A3/xx unknown
- 1974-07-15 DE DE2433943A patent/DE2433943C3/de not_active Expired
- 1974-07-16 EG EG276/74A patent/EG11430A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| IL45270A (en) | 1978-07-31 |
| BG21205A3 (bg) | 1976-03-20 |
| NL7409443A (nl) | 1975-01-20 |
| RO73277B (ro) | 1983-07-30 |
| DK152647C (da) | 1988-08-29 |
| BR7405806D0 (pt) | 1975-05-20 |
| HU169590B (ro) | 1976-12-28 |
| RO73277A (ro) | 1983-08-03 |
| NL181578C (nl) | 1987-09-16 |
| FR2237874A1 (ro) | 1975-02-14 |
| CA1024525A (en) | 1978-01-17 |
| IT1017169B (it) | 1977-07-20 |
| BG24793A3 (en) | 1978-05-12 |
| DE2433943C3 (de) | 1978-06-08 |
| IL45270A0 (en) | 1974-11-29 |
| DK379474A (ro) | 1975-03-03 |
| DE2433943B2 (de) | 1977-10-13 |
| JPS5052023A (ro) | 1975-05-09 |
| FR2237874B1 (ro) | 1978-11-24 |
| DD112120A5 (ro) | 1975-03-20 |
| EG11430A (en) | 1977-05-31 |
| DK152647B (da) | 1988-04-05 |
| GB1425304A (en) | 1976-02-18 |
| DE2433943A1 (de) | 1975-02-06 |
| NL181578B (nl) | 1987-04-16 |
| CH614689A5 (en) | 1979-12-14 |
| AU7122374A (en) | 1976-01-15 |
| JPS5537978B2 (ro) | 1980-10-01 |
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