CH399436A - Verfahren zur Herstellung von Allylestern - Google Patents

Verfahren zur Herstellung von Allylestern

Info

Publication number: CH399436A
Authority: CH; Switzerland
Prior art keywords: allyl; reaction; chloride; diallyl; halide
Prior art date: 1960-03-30

Application number

CH366961A

Other languages

German (de)

English (en)

Inventor

Stange Hugo

Bruce Tuemmler William

Forrest Allen James

Original Assignee

Fmc Corp

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.)

1960-03-30

Filing date

1961-03-28

Publication date

1965-09-30

1960-03-30 Priority claimed from US18514A external-priority patent/US3086985A/en

1961-03-28 Application filed by Fmc Corp filed Critical Fmc Corp

1965-09-30 Publication of CH399436A publication Critical patent/CH399436A/fr

Links

XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 29
-1 allyl halide Chemical class 0.000 claims description 25
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 23
238000000034 method Methods 0.000 claims description 21
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 14
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 14
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 14
239000003054 catalyst Substances 0.000 claims description 11
229910000029 sodium carbonate Inorganic materials 0.000 claims description 10
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical class ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
150000003512 tertiary amines Chemical class 0.000 claims description 7
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 claims description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical class [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
150000003973 alkyl amines Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 10
239000004641 Diallyl-phthalate Substances 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 9
239000000047 product Substances 0.000 description 8
230000032050 esterification Effects 0.000 description 7
238000005886 esterification reaction Methods 0.000 description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
150000003022 phthalic acids Chemical class 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
GATVZVWABXPTPF-UHFFFAOYSA-M triethyl(prop-2-enyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC=C GATVZVWABXPTPF-UHFFFAOYSA-M 0.000 description 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000004808 allyl alcohols Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 1
229960000228 cetalkonium chloride Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
229960001826 dimethylphthalate Drugs 0.000 description 1
XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000178 monomer Substances 0.000 description 1
GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229940112041 peripherally acting muscle relaxants other quaternary ammonium compound in atc Drugs 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
238000010926 purge Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups

Landscapes

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

CH366961A 1960-03-30 1961-03-28 Verfahren zur Herstellung von Allylestern CH399436A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US1850860A	1960-03-30	1960-03-30
US18514A US3086985A (en)	1960-03-30	1960-03-30	Preparation of diallylic phthalates

Publications (1)

Publication Number	Publication Date
CH399436A true CH399436A (fr)	1965-09-30

Family

ID=26691190

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH366961A CH399436A (fr)	1960-03-30	1961-03-28	Verfahren zur Herstellung von Allylestern

Country Status (3)

Country	Link
CH (1)	CH399436A (fr)
ES (1)	ES264693A1 (fr)
GB (1)	GB945516A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0208783A4 (fr) *	1984-12-25	1987-04-28	Mitsui Toatsu Chemicals	Procede de preparation d'esters d'allyle.

1961
- 1961-02-07 ES ES0264693A patent/ES264693A1/es not_active Expired
- 1961-03-16 GB GB961961A patent/GB945516A/en not_active Expired
- 1961-03-28 CH CH366961A patent/CH399436A/fr unknown

Also Published As

Publication number	Publication date
ES264693A1 (es)	1961-04-16
GB945516A (en)	1964-01-02

Publication	Publication Date	Title
DE851496C (de)	1952-10-06	Verfahren zur Herstellung symmetrischer oder unsymmetrischer aliphatischer, ditertiaerer Peroxyde
DE2844637C2 (de)	1986-07-10	Verfahren zur Herstellung von 2,3- Dimethyl-2,3-butandiol
DE1191367B (de)	1965-04-22	Verfahren zur Herstellung von alpha, beta-ungesaettigten Carbonsaeuren aus alpha-Oxycarbonsaeuren
EP0087585A1 (fr)	1983-09-07	Méthode de préparation de 3-alcoxi-acrylonitriles
CH399436A (fr)	1965-09-30	Verfahren zur Herstellung von Allylestern
US3086985A (en)	1963-04-23	Preparation of diallylic phthalates
DE852851C (de)	1952-10-20	Verfahren zur Herstellung von Alkylestern ª‡, ª‰-ungesaettigter Monocarbonsaeuren
DE2443142C2 (de)	1985-10-03	Verfahren zur Herstellung von Cyclopropancarbonsäurenitril
AT226224B (de)	1963-03-11	Verfahren zur Herstellung von neutralen Estern aus Phthalsäuren und β,γ-ungesättigten aliphatischen Alkoholen
DE1643195C (fr)	1973-04-19
US3256305A (en)	1966-06-14	Process for the preparation of halo-aliphatic esters of carboxylic acids
DE1141276A (de)	1962-12-20	Verfahren zur Herstellung eines Diallylphthalats
DE2827323A1 (de)	1980-01-10	Verfahren zur herstellung von halogenbutenylacrylaten
DE2703640A1 (de)	1977-08-04	Verfahren zur herstellung von aromatischen methylendioxy-verbindungen
DE1001259C2 (de)	1957-07-11	Verfahren zur Herstellung von Derivaten des Nortricyclens
DE68907758T2 (de)	1993-12-16	Propanon-1,3-disulfonsäure als Veresterungskatalysator.
DE2513952C2 (de)	1977-02-17	Verfahren zur herstellung von monochlorbenzoesaeuren
DE2245827C3 (de)	1977-06-02	Verfahren zur Herstellung von 1,1,2-Trichlorbutadlen-i ,3
DE3102826A1 (de)	1982-08-26	"verfahren zur herstellung von 2,2,4-trimethyl-1,3-pentandioldiisobutyrat"
DE2024948A1 (en)	1971-01-07	Prepn of carboxylic acid esters from an - amine a halogenated hydrocarbon and
DE1141276B (de)	1966-02-03	Verfahren zur Herstellung eiües Diaililylphlhalats
DE1211625B (de)	1966-03-03	Verfahren zur Herstellung von Diallylestern carbocyclischer aromatischer Dicarbonsaeuren
DE3237620C2 (fr)	1991-06-06
DE923426C (de)	1955-02-14	Verfahren zur Herstellung von ª‡-substituierten ª‰-Oxypropionsaeuren
DE2050678C3 (de)	1976-10-21	Verfahren zur Herstellung von Estern