NL8003199A - Werkwijze voor het bereiden van3,3-dimethylallylal- kohol. - Google Patents

Werkwijze voor het bereiden van3,3-dimethylallylal- kohol. Download PDF

Info

Publication number: NL8003199A
Authority: NL; Netherlands
Prior art keywords: dimethylallyl; alkali metal; process according; halide; ester
Prior art date: 1979-06-06

Application number

NL8003199A

Other languages

English (en)

Dutch (nl)

Original Assignee

Montedison Spa

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.)

1979-06-06

Filing date

1980-06-02

Publication date

1980-12-09

1980-06-02 Application filed by Montedison Spa filed Critical Montedison Spa

1980-12-09 Publication of NL8003199A publication Critical patent/NL8003199A/nl

Links

238000004519 manufacturing process Methods 0.000 title claims description 7
ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 claims abstract description 41
239000003444 phase transfer catalyst Substances 0.000 claims abstract description 18
239000007864 aqueous solution Substances 0.000 claims abstract description 12
238000006243 chemical reaction Methods 0.000 claims description 32
238000000034 method Methods 0.000 claims description 32
-1 alkali metal salt Chemical class 0.000 claims description 19
229910052783 alkali metal Inorganic materials 0.000 claims description 13
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 11
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
239000000243 solution Substances 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
238000003756 stirring Methods 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
XXIKYCPRDXIMQM-UHFFFAOYSA-N Isopentenyl acetate Chemical compound CC(C)=CCOC(C)=O XXIKYCPRDXIMQM-UHFFFAOYSA-N 0.000 claims description 5
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 5
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 claims description 4
239000003208 petroleum Substances 0.000 claims description 4
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
150000003983 crown ethers Chemical class 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
150000004714 phosphonium salts Chemical class 0.000 claims description 2
229920000642 polymer Polymers 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
239000004721 Polyphenylene oxide Substances 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
229910052753 mercury Inorganic materials 0.000 claims 1
229920000570 polyether Polymers 0.000 claims 1
239000012047 saturated solution Substances 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 3
159000000011 group IA salts Chemical class 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
239000012074 organic phase Substances 0.000 description 7
LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 6
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
238000006317 isomerization reaction Methods 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 4
239000000376 reactant Substances 0.000 description 4
HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical class CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
239000006227 byproduct Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 description 1
RGHQKFQZGLKBCF-UHFFFAOYSA-N 2-bromoethyl acetate Chemical compound CC(=O)OCCBr RGHQKFQZGLKBCF-UHFFFAOYSA-N 0.000 description 1
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
BKVIQODYSREJQH-UHFFFAOYSA-M [Br-].CC(C)=C[Mg+] Chemical compound [Br-].CC(C)=C[Mg+] BKVIQODYSREJQH-UHFFFAOYSA-M 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010233 benzoic acid Nutrition 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
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
ZJVWGOLNVKJRDF-UHFFFAOYSA-N dimethylallyl acetate Natural products CC(=O)OC(C)(C)C=C ZJVWGOLNVKJRDF-UHFFFAOYSA-N 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
- 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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8003199A 1979-06-06 1980-06-02 Werkwijze voor het bereiden van3,3-dimethylallylal- kohol. NL8003199A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2331679		1979-06-06
IT23316/79A IT1120780B (it)	1979-06-06	1979-06-06	Procedimento per la preparazione di alcool 3,3-dimetil-allilico

Publications (1)

Publication Number	Publication Date
NL8003199A true NL8003199A (nl)	1980-12-09

Family

ID=11205996

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8003199A NL8003199A (nl)	1979-06-06	1980-06-02	Werkwijze voor het bereiden van3,3-dimethylallylal- kohol.

Country Status (12)

Country	Link
JP (1)	JPS5612327A (fr)
BE (1)	BE883695A (fr)
CA (1)	CA1139788A (fr)
CH (1)	CH646677A5 (fr)
DE (1)	DE3021414A1 (fr)
FR (1)	FR2458529A1 (fr)
GB (1)	GB2051067B (fr)
IL (1)	IL60230A (fr)
IT (1)	IT1120780B (fr)
NL (1)	NL8003199A (fr)
SU (1)	SU1116977A3 (fr)
ZA (1)	ZA803402B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU185030B (en) *	1981-02-20	1984-11-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing isomere mixtures of pure dichloro-vinyl-cyclopropane-carboxylic acids
US5872277A (en) *	1997-03-10	1999-02-16	Loyola University Of Chicago	Methods for preparing prenyl alcohol
US6278016B1 (en)	1999-12-09	2001-08-21	Loyola University Of Chicago	Methods for conversion of isoprene to prenyl alcohol and related compounds

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2604482A (en) *	1949-04-28	1952-07-22	Pechiney Prod Chimiques Sa	Process of manufacturing organic acids, esters and alcohols
GB916772A (en) *	1960-08-18	1963-01-30	Distillers Co Yeast Ltd	Process for the production of a dicarboxylic acid ester
CH443264A (de) *	1964-01-30	1967-09-15	Alusuisse	Verfahren zur Herstellung von Diallylphthalat
GB1227144A (fr) *	1967-04-05	1971-04-07
US4152530A (en) *	1978-07-24	1979-05-01	Rhone-Poulenc Inc.	Process for preparing allylic alcohols from allylic halides
JPH1020777A (ja) *	1996-07-04	1998-01-23	Kokusai Gijutsu Kaihatsu Kk	暗号化方法、暗号通信方法、認証方法及びディジタル情報の暗号通信方法

1979
- 1979-06-06 IT IT23316/79A patent/IT1120780B/it active
1980
- 1980-06-02 NL NL8003199A patent/NL8003199A/nl not_active Application Discontinuation
- 1980-06-03 CH CH428180A patent/CH646677A5/it not_active IP Right Cessation
- 1980-06-03 FR FR8012274A patent/FR2458529A1/fr not_active Withdrawn
- 1980-06-04 IL IL60230A patent/IL60230A/xx unknown
- 1980-06-05 JP JP7502280A patent/JPS5612327A/ja active Pending
- 1980-06-05 GB GB8018497A patent/GB2051067B/en not_active Expired
- 1980-06-05 CA CA000353429A patent/CA1139788A/fr not_active Expired
- 1980-06-05 SU SU802932603A patent/SU1116977A3/ru active
- 1980-06-06 BE BE0/200937A patent/BE883695A/fr not_active IP Right Cessation
- 1980-06-06 ZA ZA00803402A patent/ZA803402B/xx unknown
- 1980-06-06 DE DE19803021414 patent/DE3021414A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
CH646677A5 (it)	1984-12-14
IT1120780B (it)	1986-03-26
FR2458529A1 (fr)	1981-01-02
IL60230A0 (en)	1980-09-16
CA1139788A (fr)	1983-01-18
DE3021414A1 (de)	1980-12-11
GB2051067A (en)	1981-01-14
ZA803402B (en)	1981-05-27
IL60230A (en)	1983-10-31
BE883695A (fr)	1980-12-08
JPS5612327A (en)	1981-02-06
SU1116977A3 (ru)	1984-09-30
IT7923316A0 (it)	1979-06-06
GB2051067B (en)	1983-06-22

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-02-02	BV	The patent application has lapsed

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JP2615780B2 (ja)	1997-06-04	２−シクロペンテノン誘導体の製造法
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