DD203906A5 - Verfahren zur herstellung von 4-alkoxyacetessigestern - Google Patents

Verfahren zur herstellung von 4-alkoxyacetessigestern Download PDF

Info

Publication number: DD203906A5
Authority: DD; German Democratic Republic
Prior art keywords: ester; chloro; reaction; preparation; alkali metal
Prior art date: 1981-10-01

Application number

DD82243521A

Other languages

German (de)

English (en)

Inventor

Erich Greth

Original Assignee

Lonza Ag

Priority date (The priority date 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 date listed.)

1981-10-01

Filing date

1982-09-27

Publication date

1983-11-09

1982-09-27 Application filed by Lonza Ag filed Critical Lonza Ag

1983-11-09 Publication of DD203906A5 publication Critical patent/DD203906A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims description 6
150000002168 ethanoic acid esters Chemical class 0.000 title 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 23
229910052783 alkali metal Inorganic materials 0.000 claims description 11
150000001340 alkali metals Chemical class 0.000 claims description 6
150000002148 esters Chemical class 0.000 abstract description 22
239000003513 alkali Substances 0.000 abstract description 4
238000004519 manufacturing process Methods 0.000 abstract description 4
239000002253 acid Substances 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
-1 bromoacetic acid ester Chemical class 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
239000011734 sodium Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 7
239000011347 resin Substances 0.000 description 7
229920005989 resin Polymers 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 5
239000000047 product Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
HFLMYYLFSNEOOT-UHFFFAOYSA-N methyl 4-chloro-3-oxobutanoate Chemical compound COC(=O)CC(=O)CCl HFLMYYLFSNEOOT-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000003158 alcohol group Chemical group 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
229940089960 chloroacetate Drugs 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000008045 alkali metal halides Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000003287 bathing Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
OVYQSRKFHNKIBM-UHFFFAOYSA-N butanedioic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)CCC(O)=O OVYQSRKFHNKIBM-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
NNXMXUSTTDFBDE-UHFFFAOYSA-N octyl 2-chloroacetate Chemical compound CCCCCCCCOC(=O)CCl NNXMXUSTTDFBDE-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical compound [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- C07C69/72—Acetoacetic acid esters

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD82243521A 1981-10-01 1982-09-27 Verfahren zur herstellung von 4-alkoxyacetessigestern DD203906A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH632181		1981-10-01

Publications (1)

Publication Number	Publication Date
DD203906A5 true DD203906A5 (de)	1983-11-09

Family

ID=4307712

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82243521A DD203906A5 (de)	1981-10-01	1982-09-27	Verfahren zur herstellung von 4-alkoxyacetessigestern

Country Status (9)

Country	Link
US (1)	US4540808A (cs)
EP (1)	EP0076379B1 (cs)
JP (1)	JPS5869836A (cs)
AT (1)	ATE13289T1 (cs)
CA (1)	CA1187509A (cs)
CS (1)	CS233735B2 (cs)
DD (1)	DD203906A5 (cs)
DE (1)	DE3263545D1 (cs)
SU (1)	SU1213982A3 (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3443678A1 (de) *	1984-11-30	1986-06-05	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von 4-acyloxy-3-oxo-buttersaeureestern
FR2577924B1 (fr) *	1985-02-28	1987-03-06	Cortial	Nouvelle methode de fabrication de l'ester de p-chlorophenol de l'acide p-chlorophenoxyisobutyrique
FR2677023B1 (fr) *	1991-05-30	1994-02-25	Eurobio Laboratoires	Derives de coumarine hydrosolubles, leur preparation et leur utilisation comme substrat d'enzyme.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH570354A5 (cs) *	1972-04-21	1975-12-15	Lonza Ag
BE788516A (fr) *	1971-09-10	1973-03-07	Lonza Ag	Procede de fabrication d'esters alcoxyacetylacetiques
JPS5318485A (en) *	1976-08-04	1978-02-20	Mitsubishi Electric Corp	Twist nematic liquid crystal composition

1982
- 1982-08-24 AT AT82107753T patent/ATE13289T1/de not_active IP Right Cessation
- 1982-08-24 EP EP82107753A patent/EP0076379B1/de not_active Expired
- 1982-08-24 DE DE8282107753T patent/DE3263545D1/de not_active Expired
- 1982-09-27 DD DD82243521A patent/DD203906A5/de not_active IP Right Cessation
- 1982-09-27 US US06/423,568 patent/US4540808A/en not_active Expired - Lifetime
- 1982-09-29 CA CA000412418A patent/CA1187509A/en not_active Expired
- 1982-09-30 JP JP57173101A patent/JPS5869836A/ja active Pending
- 1982-09-30 CS CS826986A patent/CS233735B2/cs unknown
- 1982-09-30 SU SU823495516A patent/SU1213982A3/ru active

Also Published As

Publication number	Publication date
DE3263545D1 (en)	1985-06-20
EP0076379B1 (de)	1985-05-15
CS233735B2 (en)	1985-03-14
EP0076379A1 (de)	1983-04-13
ATE13289T1 (de)	1985-06-15
JPS5869836A (ja)	1983-04-26
CA1187509A (en)	1985-05-21
US4540808A (en)	1985-09-10
SU1213982A3 (ru)	1986-02-23

Legal Events

Date	Code	Title	Description
1995-03-30	ENJ	Ceased due to non-payment of renewal fee

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