JPS6116255B2 - - Google Patents
Info
- Publication number
- JPS6116255B2 JPS6116255B2 JP55110386A JP11038680A JPS6116255B2 JP S6116255 B2 JPS6116255 B2 JP S6116255B2 JP 55110386 A JP55110386 A JP 55110386A JP 11038680 A JP11038680 A JP 11038680A JP S6116255 B2 JPS6116255 B2 JP S6116255B2
- Authority
- JP
- Japan
- Prior art keywords
- acetone
- chlorine
- reaction
- hexachloroacetone
- phosphine
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 31
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 claims description 28
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 19
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 14
- 150000007530 organic bases Chemical class 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims 2
- 238000000034 method Methods 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000005660 chlorination reaction Methods 0.000 description 7
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 6
- 239000002250 absorbent Substances 0.000 description 5
- 230000002745 absorbent Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- RVSIFWBAGVMQKT-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropan-2-one Chemical compound ClC(Cl)C(=O)C(Cl)(Cl)Cl RVSIFWBAGVMQKT-UHFFFAOYSA-N 0.000 description 4
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- SMZHKGXSEAGRTI-UHFFFAOYSA-N 1,1,1-trichloropropan-2-one Chemical compound CC(=O)C(Cl)(Cl)Cl SMZHKGXSEAGRTI-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11038680A JPS5735537A (en) | 1980-08-13 | 1980-08-13 | Preparation of hexachloroacetone |
| IT23468/81A IT1138147B (it) | 1980-08-13 | 1981-08-11 | Procedimento per la preparazione di esacloroacetone usando un catalizzatore alla fosfina per completare la clorurazione |
| FR8115641A FR2488602B1 (fr) | 1980-08-13 | 1981-08-12 | Procede de preparation d'hexachloroacetone |
| DE3131895A DE3131895C2 (de) | 1980-08-13 | 1981-08-12 | Verfahren zur Herstellung von Hexachloraceton |
| GB8124769A GB2082180B (en) | 1980-08-13 | 1981-08-13 | Process of preparing hexachloroacetone using phosphine catalyst to complete chlorination |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11038680A JPS5735537A (en) | 1980-08-13 | 1980-08-13 | Preparation of hexachloroacetone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5735537A JPS5735537A (en) | 1982-02-26 |
| JPS6116255B2 true JPS6116255B2 (zh) | 1986-04-28 |
Family
ID=14534484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11038680A Granted JPS5735537A (en) | 1980-08-13 | 1980-08-13 | Preparation of hexachloroacetone |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5735537A (zh) |
| DE (1) | DE3131895C2 (zh) |
| FR (1) | FR2488602B1 (zh) |
| GB (1) | GB2082180B (zh) |
| IT (1) | IT1138147B (zh) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009072501A1 (ja) | 2007-12-03 | 2009-06-11 | Asahi Glass Co., Ltd. | カーボネート化合物の製造方法 |
| WO2009072502A1 (ja) | 2007-12-03 | 2009-06-11 | Asahi Glass Co., Ltd. | カーボネート化合物の製造方法 |
| WO2011062104A1 (ja) | 2009-11-17 | 2011-05-26 | 旭硝子株式会社 | ポリカーボネートの製造方法 |
| WO2014024891A1 (ja) | 2012-08-10 | 2014-02-13 | 旭硝子株式会社 | カーボネート化合物および芳香族ポリカーボネートの製造方法 |
| WO2014088029A1 (ja) | 2012-12-06 | 2014-06-12 | 旭硝子株式会社 | カーボネート化合物の製造方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6504059B2 (ja) * | 2014-01-08 | 2019-04-24 | Ａｇｃ株式会社 | ヘキサクロロアセトンの製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2635117A (en) * | 1949-05-12 | 1953-04-14 | Allied Chem & Dye Corp | Preparation of polychloroacetones |
| US3265740A (en) * | 1962-07-11 | 1966-08-09 | Du Pont | Process for chlorinating acetone and acetylacetone |
| US3988369A (en) * | 1974-09-26 | 1976-10-26 | Pearson Donald E | Process and reactant for halogenating organic compounds |
-
1980
- 1980-08-13 JP JP11038680A patent/JPS5735537A/ja active Granted
-
1981
- 1981-08-11 IT IT23468/81A patent/IT1138147B/it active
- 1981-08-12 FR FR8115641A patent/FR2488602B1/fr not_active Expired
- 1981-08-12 DE DE3131895A patent/DE3131895C2/de not_active Expired
- 1981-08-13 GB GB8124769A patent/GB2082180B/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009072501A1 (ja) | 2007-12-03 | 2009-06-11 | Asahi Glass Co., Ltd. | カーボネート化合物の製造方法 |
| WO2009072502A1 (ja) | 2007-12-03 | 2009-06-11 | Asahi Glass Co., Ltd. | カーボネート化合物の製造方法 |
| WO2011062104A1 (ja) | 2009-11-17 | 2011-05-26 | 旭硝子株式会社 | ポリカーボネートの製造方法 |
| WO2014024891A1 (ja) | 2012-08-10 | 2014-02-13 | 旭硝子株式会社 | カーボネート化合物および芳香族ポリカーボネートの製造方法 |
| WO2014088029A1 (ja) | 2012-12-06 | 2014-06-12 | 旭硝子株式会社 | カーボネート化合物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2082180A (en) | 1982-03-03 |
| IT8123468A0 (it) | 1981-08-11 |
| DE3131895A1 (de) | 1982-03-25 |
| DE3131895C2 (de) | 1984-10-31 |
| FR2488602A1 (fr) | 1982-02-19 |
| GB2082180B (en) | 1984-07-11 |
| JPS5735537A (en) | 1982-02-26 |
| IT1138147B (it) | 1986-09-17 |
| FR2488602B1 (fr) | 1985-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS60237030A (ja) | １，２，３‐トリクロル‐２‐メチループロンの製法 | |
| JPS6116255B2 (zh) | ||
| EP0004636B1 (en) | Process for preparing benzotrifluoride and its derivatives | |
| JP2006518734A (ja) | 重炭酸塩を触媒として用いるオキシジフタル酸無水物の製造方法 | |
| JPH0237342B2 (zh) | ||
| CA1037051A (en) | Continuous process for producing glycide | |
| CN113735680A (zh) | 一种2,4-二氯氯苄的合成方法 | |
| JPH0237343B2 (zh) | ||
| US4388251A (en) | Method for preparing 2-chlorobenzoyl chloride | |
| JPS5852267A (ja) | 不飽和スルホンの製造方法 | |
| JPH0660130B2 (ja) | １―ブロモエチルヒドロカルボニルカーボネートの製造方法 | |
| JPS608236A (ja) | イソブチリルフルオリドの製法 | |
| JPH09278704A (ja) | モノクロロピナコロンの製造方法 | |
| JPS6137748A (ja) | ヘミアセタールからフロラールの純粋水和物を製造する方法 | |
| JPS6052134B2 (ja) | ヘキサフルオロイソブテンの製造法 | |
| JPH0359907B2 (zh) | ||
| JPH0461862B2 (zh) | ||
| JPH0469362A (ja) | アセト酢酸ｌ―メンチルエステルの製造方法 | |
| JP3188519B2 (ja) | ｔｅｒｔ−ブチルクロライドの製造法 | |
| JP2539876B2 (ja) | ２，２，６，６−テトラメチル−４−オキソピペリジンの製造方法 | |
| JPS6312862B2 (zh) | ||
| KR830000207B1 (ko) | 케타진(ketazine)의 제조방법 | |
| JPH0366294B2 (zh) | ||
| JP3757478B2 (ja) | ２，４，５−トリフルオロ−３−ヨ−ド安息香酸の製造法 | |
| JPS6219544A (ja) | ２，３−ジクロル−１−プロパノ−ルの製法 |