DE1931964C3 - Verfahren zur Herstellung von Acetessigsäuren - Google Patents
Verfahren zur Herstellung von AcetessigsäurenInfo
- Publication number
- DE1931964C3 DE1931964C3 DE1931964A DE1931964A DE1931964C3 DE 1931964 C3 DE1931964 C3 DE 1931964C3 DE 1931964 A DE1931964 A DE 1931964A DE 1931964 A DE1931964 A DE 1931964A DE 1931964 C3 DE1931964 C3 DE 1931964C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- acetoacetic
- halogen
- hydrogen
- carried out
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 150000004720 acetoacetic acids Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 22
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 8
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 6
- PLMCCOPFYJURPS-UHFFFAOYSA-N gamma-bromoacetoacetic acid Natural products OC(=O)CC(=O)CBr PLMCCOPFYJURPS-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 4
- UCTNTYHJFWMUBD-UHFFFAOYSA-N 4-chloro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)CCl UCTNTYHJFWMUBD-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000010183 spectrum analysis Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- AXWKFRWLYPZEFQ-UHFFFAOYSA-N 3-oxobutanoyl chloride Chemical compound CC(=O)CC(Cl)=O AXWKFRWLYPZEFQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- -1 halogen Acetoacetic acid halides Chemical class 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical group Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003860 storage Methods 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
- C07C51/04—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid halides
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1003568A CH492668A (de) | 1968-07-04 | 1968-07-04 | Verfahren zur Herstellung von Acetessigsäuren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1931964A1 DE1931964A1 (de) | 1970-04-02 |
| DE1931964B2 DE1931964B2 (de) | 1977-11-24 |
| DE1931964C3 true DE1931964C3 (de) | 1978-08-10 |
Family
ID=4358628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1931964A Expired DE1931964C3 (de) | 1968-07-04 | 1969-06-24 | Verfahren zur Herstellung von Acetessigsäuren |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3701803A (member.php) |
| JP (1) | JPS4936210B1 (member.php) |
| AT (1) | AT289746B (member.php) |
| BE (1) | BE735594A (member.php) |
| BR (1) | BR6910405D0 (member.php) |
| CH (1) | CH492668A (member.php) |
| CS (1) | CS172313B2 (member.php) |
| DE (1) | DE1931964C3 (member.php) |
| DK (1) | DK127552B (member.php) |
| ES (1) | ES368929A1 (member.php) |
| FR (1) | FR2012304A1 (member.php) |
| GB (1) | GB1209725A (member.php) |
| NL (1) | NL164548C (member.php) |
| NO (1) | NO125972B (member.php) |
| SE (1) | SE366021B (member.php) |
| YU (1) | YU32501B (member.php) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950412A (en) * | 1971-06-08 | 1976-04-13 | Lonza Ltd. | Method for the production of haloacetoacetic acids |
| US4076911A (en) | 1975-11-05 | 1978-02-28 | Union Oil Company Of California | Ethylene-carbon monoxide copolymers |
| US4529704A (en) * | 1979-11-05 | 1985-07-16 | Miles Laboratories, Inc. | Device and method for preparation of a control solution for ketone determination. |
| CS221992B2 (en) * | 1980-11-19 | 1983-04-29 | Lonza Ag | Method of making the 2,2-dichloracetoacetylchloride |
| IL65246A (en) * | 1981-03-26 | 1985-11-29 | Lonza Ag | Process for the preparation of 2-chloroacetoacetamides |
| US4473508A (en) * | 1982-11-13 | 1984-09-25 | Lonza Ltd. | Process for the production of γ-chloroacetoacetic acid chloride |
| CH666483A5 (de) * | 1985-01-16 | 1988-07-29 | Lonza Ag | Verfahren zur herstellung von thiotetronsaeure. |
| US5417861A (en) * | 1990-11-30 | 1995-05-23 | N-Viro International Corporation | Process to stabilize bioorganic, raw or treated wastewater sludge |
| EP2518043A1 (en) | 2011-04-29 | 2012-10-31 | Lonza Ltd. | Process for the production of 4-chloroacetyl chloride, 4-chloroacetic acid esters, amides and imides |
-
1968
- 1968-07-04 CH CH1003568A patent/CH492668A/de not_active IP Right Cessation
-
1969
- 1969-06-24 DE DE1931964A patent/DE1931964C3/de not_active Expired
- 1969-06-28 ES ES368929A patent/ES368929A1/es not_active Expired
- 1969-06-30 YU YU1669/69A patent/YU32501B/xx unknown
- 1969-07-02 SE SE09427/69A patent/SE366021B/xx unknown
- 1969-07-02 US US838646A patent/US3701803A/en not_active Expired - Lifetime
- 1969-07-03 FR FR6922633A patent/FR2012304A1/fr not_active Withdrawn
- 1969-07-03 GB GB33606/69A patent/GB1209725A/en not_active Expired
- 1969-07-03 NO NO2788/69A patent/NO125972B/no unknown
- 1969-07-03 DK DK362469AA patent/DK127552B/da not_active IP Right Cessation
- 1969-07-03 BE BE735594D patent/BE735594A/xx not_active IP Right Cessation
- 1969-07-03 BR BR210405/69A patent/BR6910405D0/pt unknown
- 1969-07-04 AT AT646069A patent/AT289746B/de not_active IP Right Cessation
- 1969-07-04 JP JP44052995A patent/JPS4936210B1/ja active Pending
- 1969-07-04 CS CS4791A patent/CS172313B2/cs unknown
- 1969-07-04 NL NL6910304.A patent/NL164548C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL164548B (nl) | 1980-08-15 |
| SE366021B (member.php) | 1974-04-08 |
| NL164548C (nl) | 1981-01-15 |
| NO125972B (member.php) | 1972-12-04 |
| CS172313B2 (member.php) | 1976-12-29 |
| AT289746B (de) | 1971-05-10 |
| DE1931964B2 (de) | 1977-11-24 |
| CH492668A (de) | 1970-06-30 |
| US3701803A (en) | 1972-10-31 |
| BE735594A (member.php) | 1969-12-16 |
| YU166969A (en) | 1974-06-30 |
| DE1931964A1 (de) | 1970-04-02 |
| DK127552B (da) | 1973-11-26 |
| JPS4936210B1 (member.php) | 1974-09-28 |
| NL6910304A (member.php) | 1970-01-06 |
| YU32501B (en) | 1974-12-31 |
| ES368929A1 (es) | 1971-05-01 |
| GB1209725A (en) | 1970-10-21 |
| BR6910405D0 (pt) | 1973-01-09 |
| FR2012304A1 (member.php) | 1970-03-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |