NL193189C - Werkwijze voor het alkyleren van de methyleengroep van een organische verbinding met een actieve methyleengroep. - Google Patents

Werkwijze voor het alkyleren van de methyleengroep van een organische verbinding met een actieve methyleengroep. Download PDF

Info

Publication number: NL193189C
Authority: NL; Netherlands
Prior art keywords: isopropyl; mmhg; alkali metal; methyl; metal hydroxide
Prior art date: 1978-09-26

Application number

NL7907113A

Other languages

English (en)

Dutch (nl)

Other versions

NL193189B (nl

NL7907113A (nl

Original Assignee

Ihara Chemical Ind Co

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.)

1978-09-26

Filing date

1979-09-25

Publication date

1999-02-02

1978-09-26 Priority claimed from JP11850178A external-priority patent/JPS5547222A/ja

1978-10-30 Priority claimed from JP13338078A external-priority patent/JPS5559113A/ja

1978-10-30 Priority claimed from JP13337978A external-priority patent/JPS5559157A/ja

1979-09-25 Application filed by Ihara Chemical Ind Co filed Critical Ihara Chemical Ind Co

1980-03-28 Publication of NL7907113A publication Critical patent/NL7907113A/nl

1998-10-01 Publication of NL193189B publication Critical patent/NL193189B/xx

1999-02-02 Application granted granted Critical

1999-02-02 Publication of NL193189C publication Critical patent/NL193189C/nl

Links

238000000034 method Methods 0.000 title claims description 46
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 title claims description 14
230000002152 alkylating effect Effects 0.000 title claims description 4
150000002894 organic compounds Chemical class 0.000 title claims description 4
-1 α-isopropyl-4-t-butylphenylacetonitrile Chemical compound 0.000 claims description 62
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 51
239000006185 dispersion Substances 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 27
239000003960 organic solvent Substances 0.000 claims description 22
239000002245 particle Substances 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
238000009835 boiling Methods 0.000 claims description 9
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
238000002844 melting Methods 0.000 claims description 4
230000008018 melting Effects 0.000 claims description 4
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
HYXJXCNHNYUWAZ-UHFFFAOYSA-N 2-methoxy-2-phenylacetonitrile Chemical compound COC(C#N)C1=CC=CC=C1 HYXJXCNHNYUWAZ-UHFFFAOYSA-N 0.000 claims description 2
IZPUPXNVRNBDSW-UHFFFAOYSA-N 2-phenylbutanenitrile Chemical compound CCC(C#N)C1=CC=CC=C1 IZPUPXNVRNBDSW-UHFFFAOYSA-N 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
IAZOLAFPWWQXGU-UHFFFAOYSA-N 3-methyl-2-phenylbutanenitrile Chemical compound CC(C)C(C#N)C1=CC=CC=C1 IAZOLAFPWWQXGU-UHFFFAOYSA-N 0.000 claims 2
DIWVBIXQCNRCFE-QMMMGPOBSA-N (2s)-2-methoxy-2-phenylacetic acid Chemical compound CO[C@H](C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-QMMMGPOBSA-N 0.000 claims 1
HDTAUMIOSWQZRW-UHFFFAOYSA-N 2,2-dichloro-2-phenylacetonitrile Chemical compound N#CC(Cl)(Cl)C1=CC=CC=C1 HDTAUMIOSWQZRW-UHFFFAOYSA-N 0.000 claims 1
GSBAWTQJMFJVSW-UHFFFAOYSA-N 2-(2,3,4-trimethylphenyl)acetonitrile Chemical compound CC1=CC=C(CC#N)C(C)=C1C GSBAWTQJMFJVSW-UHFFFAOYSA-N 0.000 claims 1
PGQTYXFMSZUGOW-UHFFFAOYSA-N 2-methyl-2-phenylpropanenitrile Chemical compound N#CC(C)(C)C1=CC=CC=C1 PGQTYXFMSZUGOW-UHFFFAOYSA-N 0.000 claims 1
GTTJSBZHRDAELL-UHFFFAOYSA-N 3,3,3-trifluoro-2-phenylpropanenitrile Chemical compound FC(F)(F)C(C#N)C1=CC=CC=C1 GTTJSBZHRDAELL-UHFFFAOYSA-N 0.000 claims 1
HDLQGISFYDYWFJ-UHFFFAOYSA-N 3-methyl-2-phenylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=CC=C1 HDLQGISFYDYWFJ-UHFFFAOYSA-N 0.000 claims 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 1
229920005556 chlorobutyl Polymers 0.000 claims 1
125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 123
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
238000002360 preparation method Methods 0.000 description 31
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 19
238000003756 stirring Methods 0.000 description 19
239000008096 xylene Substances 0.000 description 19
239000007787 solid Substances 0.000 description 13
239000003381 stabilizer Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 11
229920001451 polypropylene glycol Polymers 0.000 description 11
239000002904 solvent Substances 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
235000014113 dietary fatty acids Nutrition 0.000 description 10
239000000194 fatty acid Substances 0.000 description 10
229930195729 fatty acid Natural products 0.000 description 10
150000003242 quaternary ammonium salts Chemical class 0.000 description 10
239000003054 catalyst Substances 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001350 alkyl halides Chemical class 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 6
229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
229920001213 Polysorbate 20 Polymers 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000002798 polar solvent Substances 0.000 description 5
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 5
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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150000004665 fatty acids Chemical class 0.000 description 4
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ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 4
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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150000001340 alkali metals Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000010419 fine particle Substances 0.000 description 3
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 3
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QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000002736 nonionic surfactant Substances 0.000 description 3
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239000007858 starting material Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
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ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
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HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000008045 alkali metal halides Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
XUHFBOUSHUEAQZ-UHFFFAOYSA-N bromobenzyl cyanide Chemical compound N#CC(Br)C1=CC=CC=C1 XUHFBOUSHUEAQZ-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
239000000539 dimer Substances 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
DTMBBJMZKOOEDO-UHFFFAOYSA-N ethyl 2-cyanoacetate;1-iodobutane Chemical compound CCCCI.CCOC(=O)CC#N DTMBBJMZKOOEDO-UHFFFAOYSA-N 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000005179 haloacetyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
229920001289 polyvinyl ether Polymers 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000243 solution Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
229940031953 sorbitan monopalmitate Drugs 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
229960005078 sorbitan sesquioleate Drugs 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
229960004129 sorbitan tristearate Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

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

NL7907113A 1978-09-26 1979-09-25 Werkwijze voor het alkyleren van de methyleengroep van een organische verbinding met een actieve methyleengroep. NL193189C (nl)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP11850178A JPS5547222A (en)	1978-09-26	1978-09-26	Production of alkali hydroxide fine grain
JP11850178		1978-09-26
JP13338078		1978-10-30
JP13338078A JPS5559113A (en)	1978-10-30	1978-10-30	Method of making alkylated product of active methylene compound
JP13337978		1978-10-30
JP13337978A JPS5559157A (en)	1978-10-30	1978-10-30	Production alpha-isopropyl-halo substituted phenylacetonitrile

Publications (3)

Publication Number	Publication Date
NL7907113A NL7907113A (nl)	1980-03-28
NL193189B NL193189B (nl)	1998-10-01
NL193189C true NL193189C (nl)	1999-02-02

Family

ID=27313598

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7907113A NL193189C (nl)	1978-09-26	1979-09-25	Werkwijze voor het alkyleren van de methyleengroep van een organische verbinding met een actieve methyleengroep.

Country Status (7)

Country	Link
US (1)	US4307034A (it)
CA (1)	CA1142961A (it)
CH (1)	CH646615A5 (it)
DE (1)	DE2937945A1 (it)
GB (2)	GB2082563B (it)
IT (1)	IT1165340B (it)
NL (1)	NL193189C (it)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4377531A (en) *	1981-10-07	1983-03-22	American Cyanamid Company	Method for the alkylation of phenylacetonitriles
US4736056A (en) *	1986-12-15	1988-04-05	Smith Oliver W	Process for the production of malonic acid derivative compounds
US6653355B1 (en) *	1999-03-03	2003-11-25	Hakugen Co., Ltd.	Treating agent for oil
JP4449246B2 (ja) *	2001-04-12	2010-04-14	トヨタ自動車株式会社	無電解めっき材の前処理方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3755412A (en) *	1969-07-07	1973-08-28	Exxon Research Engineering Co	Alkylation of acetonitriles
US4062968A (en) *	1972-07-11	1977-12-13	Sumitomo Chemical Company, Limited	Insecticidal substituted acetate compounds
JPS5163145A (en) *	1974-11-26	1976-06-01	Sumitomo Chemical Co	33 mechiru 22 * 44 harogenofueniru * buchironitoriruno seizoho

1979
- 1979-09-13 US US06/075,314 patent/US4307034A/en not_active Expired - Lifetime
- 1979-09-20 DE DE19792937945 patent/DE2937945A1/de active Granted
- 1979-09-25 CA CA000336278A patent/CA1142961A/en not_active Expired
- 1979-09-25 CH CH862079A patent/CH646615A5/de not_active IP Right Cessation
- 1979-09-25 NL NL7907113A patent/NL193189C/nl not_active IP Right Cessation
- 1979-09-26 GB GB8131017A patent/GB2082563B/en not_active Expired
- 1979-09-26 IT IT26018/79A patent/IT1165340B/it active
- 1979-09-26 GB GB7933248A patent/GB2033362B/en not_active Expired

Also Published As

Publication number	Publication date
IT7926018A0 (it)	1979-09-26
US4307034A (en)	1981-12-22
CA1142961A (en)	1983-03-15
DE2937945C2 (it)	1992-01-23
GB2033362B (en)	1982-10-13
DE2937945A1 (de)	1980-04-03
GB2082563A (en)	1982-03-10
GB2033362A (en)	1980-05-21
GB2082563B (en)	1983-03-02
NL193189B (nl)	1998-10-01
CH646615A5 (de)	1984-12-14
IT1165340B (it)	1987-04-22
NL7907113A (nl)	1980-03-28

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1986-08-01	BA	A request for search or an international-type search has been filed
1986-08-01	BB	A search report has been drawn up
1986-11-03	BC	A request for examination has been filed
1999-12-01	V4	Discontinued because of reaching the maximum lifetime of a patent	Free format text: 19990925

Publication	Publication Date	Title
NL193189C (nl)	1999-02-02	Werkwijze voor het alkyleren van de methyleengroep van een organische verbinding met een actieve methyleengroep.
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EP0076220B1 (fr)	1985-08-07	Procédé d'hydrolyse d'éthers aryl-aliphatiques
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JPH024580B2 (it)	1990-01-29
US4418017A (en)	1983-11-29	Preparation of phenylacetonitriles carrying basic substituents
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JPH07196600A (ja)	1995-08-01	２，２’−ジニトロジフエニルジスルフイドの改良された製法
JPS6323177B2 (it)	1988-05-16
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