CA1116630A - Preparation of chloroacetyl chloride - Google Patents
Preparation of chloroacetyl chlorideInfo
- Publication number
- CA1116630A CA1116630A CA000321297A CA321297A CA1116630A CA 1116630 A CA1116630 A CA 1116630A CA 000321297 A CA000321297 A CA 000321297A CA 321297 A CA321297 A CA 321297A CA 1116630 A CA1116630 A CA 1116630A
- Authority
- CA
- Canada
- Prior art keywords
- chloride
- chloroacetyl chloride
- glycolic acid
- catalyst
- reaction
- 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
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title description 11
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims abstract description 40
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 40
- -1 nitrogen-containing organic compound Chemical class 0.000 claims abstract description 29
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 235000013877 carbamide Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical group CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 2
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- GNGUMAGSNTVFLB-UHFFFAOYSA-N 3-butyloxolan-2-one Chemical compound CCCCC1CCOC1=O GNGUMAGSNTVFLB-UHFFFAOYSA-N 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- GSSHGHPBCWUHPB-UHFFFAOYSA-N 4-chloro-2-hydroxy-3-oxobutanoyl chloride Chemical compound ClC(=O)C(O)C(=O)CCl GSSHGHPBCWUHPB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GIPIDQABPPVVSH-UHFFFAOYSA-N n-methylacetamide Chemical compound [CH2]C(=O)NC GIPIDQABPPVVSH-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/891,429 US4129595A (en) | 1978-03-29 | 1978-03-29 | Preparation of chloroacetyl chloride |
| US891,429 | 1978-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1116630A true CA1116630A (en) | 1982-01-19 |
Family
ID=25398166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000321297A Expired CA1116630A (en) | 1978-03-29 | 1979-02-12 | Preparation of chloroacetyl chloride |
Country Status (7)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2943432A1 (de) * | 1979-10-26 | 1981-05-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von carbonsaeurehalogeniden |
| DE3019526A1 (de) * | 1980-05-22 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von chlorameisensaeurearylestern |
| JPS6030666B2 (ja) * | 1980-08-20 | 1985-07-17 | 鐘淵化学工業株式会社 | 光学活性メルカプトカルボン酸の製造法 |
| DE4116365A1 (de) * | 1991-05-18 | 1992-11-19 | Basf Ag | Verfahren zur herstellung von alkyl-, alkenyl- und alkinylchloriden |
| AU727200B2 (en) | 1996-03-15 | 2000-12-07 | Dow Agrosciences Llc | Halogenation catalyst |
| DE19753773A1 (de) * | 1997-12-04 | 1999-06-10 | Basf Ag | Verfahren zur Herstellung von Chlorcarbonsäurechloriden |
| US7435849B2 (en) | 2005-10-31 | 2008-10-14 | Hoffmann-La Roche Inc. | Process for the production of acid chlorides |
| ES2395167T3 (es) * | 2007-04-25 | 2013-02-08 | F. Hoffmann-La Roche Ag | Nuevo proceso para la obtención de cloruros de ácido |
| MX2010009876A (es) * | 2008-04-04 | 2010-09-28 | Hoffmann La Roche | Nuevo proceso para la preparacion de derivados de acido ciclohexanocarboxilico por medio del derivado de ciclohexanocarboxamida correspondiente. |
| CN101981001B (zh) * | 2008-04-04 | 2016-06-08 | 弗·哈夫曼-拉罗切有限公司 | 制备环己烷甲酸衍生物的新方法 |
| AU2009259495B2 (en) | 2008-06-17 | 2014-04-03 | F. Hoffmann-La Roche Ag | 1-(2-ethyl-butyl) -cyclohexanecarboxylic acid ester as an intermediate in the preparation of pharmaceutically active amides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899458A (en) * | 1959-08-11 | Process for producing oxy aromatic | ||
| US2889365A (en) * | 1957-06-27 | 1959-06-02 | Monsanto Chemicals | Process for producing monochloroacetyl chloride by chlorinating ketene in sulfur dioxide |
-
1978
- 1978-03-29 US US05/891,429 patent/US4129595A/en not_active Expired - Lifetime
-
1979
- 1979-02-12 CA CA000321297A patent/CA1116630A/en not_active Expired
- 1979-03-10 DE DE19792909444 patent/DE2909444A1/de active Granted
- 1979-03-12 CH CH234279A patent/CH637102A5/fr not_active IP Right Cessation
- 1979-03-22 FR FR7907258A patent/FR2421164A1/fr active Granted
- 1979-03-27 GB GB7910703A patent/GB2017696B/en not_active Expired
- 1979-03-28 JP JP3681779A patent/JPS54151911A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4129595A (en) | 1978-12-12 |
| GB2017696A (en) | 1979-10-10 |
| FR2421164A1 (fr) | 1979-10-26 |
| JPS5726657B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-06-05 |
| JPS54151911A (en) | 1979-11-29 |
| GB2017696B (en) | 1982-11-10 |
| DE2909444C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-02-23 |
| CH637102A5 (fr) | 1983-07-15 |
| FR2421164B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-01-07 |
| DE2909444A1 (de) | 1979-10-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |