DD153824A5 - Verfahren zur herstellung von 1,3-dibrom-2,2-dimethyl-propan-1,3-dicarbonsaeure-derivaten - Google Patents

Verfahren zur herstellung von 1,3-dibrom-2,2-dimethyl-propan-1,3-dicarbonsaeure-derivaten Download PDF

Info

Publication number: DD153824A5
Authority: DD; German Democratic Republic
Prior art keywords: dimethyl; propane; dicarboxylic acid; dibromo; chloride
Prior art date: 1979-06-12

Application number

DD80221760A

Other languages

German (de)

English (en)

Inventor

Fritz Maurer

Uwe Priesnitz

Hans-Jochen Riebel

Original Assignee

Bayer 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.)

1979-06-12

Filing date

1980-06-11

Publication date

1982-02-03

1980-06-11 Application filed by Bayer Ag filed Critical Bayer Ag

1982-02-03 Publication of DD153824A5 publication Critical patent/DD153824A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 20
OUTAAMNNNOHOGA-UHFFFAOYSA-N 2,4-dibromo-3,3-dimethylpentanedioic acid Chemical class OC(=O)C(Br)C(C)(C)C(Br)C(O)=O OUTAAMNNNOHOGA-UHFFFAOYSA-N 0.000 title abstract description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 19
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 19
229910052794 bromium Inorganic materials 0.000 claims abstract description 19
238000002360 preparation method Methods 0.000 claims abstract description 9
238000006243 chemical reaction Methods 0.000 claims abstract description 8
150000001805 chlorine compounds Chemical class 0.000 claims abstract description 8
239000003054 catalyst Substances 0.000 claims abstract description 7
150000001298 alcohols Chemical class 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
DUHQIGLHYXLKAE-UHFFFAOYSA-N 3,3-dimethylglutaric acid Chemical class OC(=O)CC(C)(C)CC(O)=O DUHQIGLHYXLKAE-UHFFFAOYSA-N 0.000 abstract description 4
238000007796 conventional method Methods 0.000 abstract description 3
XSMCAAWLIYVGNF-UHFFFAOYSA-N 2,4-dibromo-3,3-dimethylpentanedioyl dichloride Chemical class ClC(=O)C(Br)C(C)(C)C(Br)C(Cl)=O XSMCAAWLIYVGNF-UHFFFAOYSA-N 0.000 abstract 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000009835 boiling Methods 0.000 description 11
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
-1 chloride ester Chemical class 0.000 description 6
239000000203 mixture Substances 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000001294 propane Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 description 2
HIJQFTSZBHDYKW-UHFFFAOYSA-N 4,4-dimethyloxane-2,6-dione Chemical compound CC1(C)CC(=O)OC(=O)C1 HIJQFTSZBHDYKW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
150000008064 anhydrides Chemical class 0.000 description 2
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000000950 dibromo group Chemical group Br* 0.000 description 2
150000001990 dicarboxylic acid derivatives Chemical group 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 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
238000005292 vacuum distillation Methods 0.000 description 2
PBIJFSCPEFQXBB-UHFFFAOYSA-N 1,1-dimethylcyclopropane Chemical compound CC1(C)CC1 PBIJFSCPEFQXBB-UHFFFAOYSA-N 0.000 description 1
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
UDFXARMKNOKMTR-UHFFFAOYSA-N 2,4-dibromo-5-methoxy-3,3-dimethyl-5-oxopentanoic acid Chemical compound COC(=O)C(Br)C(C)(C)C(Br)C(O)=O UDFXARMKNOKMTR-UHFFFAOYSA-N 0.000 description 1
235000018185 Betula X alpestris Nutrition 0.000 description 1
235000018212 Betula X uliginosa Nutrition 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
235000011950 custard Nutrition 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
NPEAPWIQJBAJIO-UHFFFAOYSA-N dimethyl 3,3-dimethylpentanedioate Chemical compound COC(=O)CC(C)(C)CC(=O)OC NPEAPWIQJBAJIO-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/36—Acyl halides
- C07C55/40—Acyl halides containing halogen outside the carboxyl halide group

Landscapes

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

DD80221760A 1979-06-12 1980-06-11 Verfahren zur herstellung von 1,3-dibrom-2,2-dimethyl-propan-1,3-dicarbonsaeure-derivaten DD153824A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792923775 DE2923775A1 (de)	1979-06-12	1979-06-12	Verfahren zur herstellung von 1,3-dibrom-2,2-dimethyl-propan-1,3-dicarbonsaeure-derivaten sowie 1,3-dibrom- 2,2-dimethyl-propan-1,3-dicarbonsaeure- dichlorid- und -chlorid-ester als neue zwischenprodukte

Publications (1)

Publication Number	Publication Date
DD153824A5 true DD153824A5 (de)	1982-02-03

Family

ID=6073064

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80221760A DD153824A5 (de)	1979-06-12	1980-06-11	Verfahren zur herstellung von 1,3-dibrom-2,2-dimethyl-propan-1,3-dicarbonsaeure-derivaten

Country Status (9)

Country	Link
US (1)	US4321408A (da)
EP (1)	EP0021112A1 (da)
JP (1)	JPS562930A (da)
BR (1)	BR8003642A (da)
DD (1)	DD153824A5 (da)
DE (1)	DE2923775A1 (da)
DK (1)	DK251780A (da)
IL (1)	IL60264A0 (da)
PL (1)	PL224847A1 (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3624258A1 (de) *	1986-07-18	1988-01-21	Basf Ag	Verfahren zur herstellung von chlorcarbonsaeurechloriden
FR2606773B1 (fr) *	1986-11-14	1989-02-24	Rhone Poulenc Chimie	Procede de preparation de diesters de l'acide hexenedioique
CN103804191A (zh) *	2014-01-23	2014-05-21	安徽华润涂料有限公司	一种2-溴丙酸乙酯合成的生产工艺
CN107556189A (zh) *	2017-08-01	2018-01-09	新华制药（寿光）有限公司	一种2‑氯丙酸甲酯的制备方法

1979
- 1979-06-12 DE DE19792923775 patent/DE2923775A1/de not_active Withdrawn
1980
- 1980-05-27 US US06/153,297 patent/US4321408A/en not_active Expired - Lifetime
- 1980-05-30 EP EP80103020A patent/EP0021112A1/de not_active Withdrawn
- 1980-06-09 IL IL60264A patent/IL60264A0/xx unknown
- 1980-06-10 JP JP7726480A patent/JPS562930A/ja active Pending
- 1980-06-10 PL PL22484780A patent/PL224847A1/xx unknown
- 1980-06-11 DD DD80221760A patent/DD153824A5/de unknown
- 1980-06-11 BR BR8003642A patent/BR8003642A/pt unknown
- 1980-06-11 DK DK251780A patent/DK251780A/da unknown

Also Published As

Publication number	Publication date
JPS562930A (en)	1981-01-13
DE2923775A1 (de)	1980-12-18
BR8003642A (pt)	1981-01-05
PL224847A1 (da)	1981-03-27
DK251780A (da)	1980-12-13
EP0021112A1 (de)	1981-01-07
IL60264A0 (en)	1980-09-16
US4321408A (en)	1982-03-23

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