GB1209905A - Long chain hydrocarbon amides and process for their production - Google Patents
Long chain hydrocarbon amides and process for their productionInfo
- Publication number
- GB1209905A GB1209905A GB5586068A GB5586068A GB1209905A GB 1209905 A GB1209905 A GB 1209905A GB 5586068 A GB5586068 A GB 5586068A GB 5586068 A GB5586068 A GB 5586068A GB 1209905 A GB1209905 A GB 1209905A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- hydrogen
- group
- alkoxy
- amides
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- -1 hydrocarbon amides Chemical class 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 title abstract 2
- 229930195733 hydrocarbon Natural products 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 150000001408 amides Chemical class 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 3
- 150000002118 epoxides Chemical class 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 1
- YFEXZJKJPFNYKB-UHFFFAOYSA-N 2-(oxolan-2-yloxy)oxolane Chemical class C1CCOC1OC1OCCC1 YFEXZJKJPFNYKB-UHFFFAOYSA-N 0.000 abstract 1
- MKMXIGGPMXDCPZ-UHFFFAOYSA-N 3,7,11-trimethyltrideca-2,6,10-trienamide Chemical compound CC(=CC(=O)N)CCC=C(CCC=C(CC)C)C MKMXIGGPMXDCPZ-UHFFFAOYSA-N 0.000 abstract 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- ZUEKVBFNKSYWLL-UHFFFAOYSA-N 7-ethyl-3,11-dimethyltrideca-2,6,10-trienamide Chemical compound CC(=CC(=O)N)CCC=C(CCC=C(CC)C)CC ZUEKVBFNKSYWLL-UHFFFAOYSA-N 0.000 abstract 1
- 241000238421 Arthropoda Species 0.000 abstract 1
- PVIAALKTNMNBNX-UHFFFAOYSA-K C1(=CC=CC=C1)[Hg](Br)(Cl)Cl Chemical compound C1(=CC=CC=C1)[Hg](Br)(Cl)Cl PVIAALKTNMNBNX-UHFFFAOYSA-K 0.000 abstract 1
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 230000036571 hydration Effects 0.000 abstract 1
- 238000006703 hydration reaction Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000005647 hydrohalogenation reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 abstract 1
- 230000035800 maturation Effects 0.000 abstract 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- ZHMUANACXUSCMY-UHFFFAOYSA-N trimethyl(trifluoromethyl)stannane Chemical compound C[Sn](C)(C)C(F)(F)F ZHMUANACXUSCMY-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/44—Halogenated alcohols containing saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,209,905. Long chain hydrocarbon amides. ZOECON CORP. 30 Aug., 1967 [29 Dec., 1966; 24 Feb., 1967], No. 55860/68. Divided out of 1,209,902. Heading C2C. [Also in Division A5] The invention comprises amides of the formula in which each of R<SP>7</SP> and R<SP>8</SP> is hydrogen, C 1-6 alkyl, C 1-5 -hydroxyalkyl, C 1-6 -alkoxy-C 1-6 -alkyl, phenyl or together represent pyrrolidino, morpholino, piperidino, piperazino or 4-C 1-6 -alkylpiperazino, each of R<SP>1-4</SP> is a C 1-6 alkyl group, Z<SP>2</SP> is H or OH, Z<SP>3</SP> is H, OH, Cl, Br, F or C 1-6 alkoxy or when taken together with Z<SP>2</SP> represents a carbon-carbon double bond, -O-, or -CH 2 -, Z<SP>6</SP> is H, OH, Br, Cl or F, Z' is H, OH, Br, Cl, F or C 1-6 alkoxy or when taken together with Z<SP>6</SP> represents a carbon-carbon double bond, -O-, -CH 2 -, -CCl 2 - or -CF 2 -, Z<SP>10</SP> is H, OH, Br, Cl or F and Z<SP>11</SP> is H, OH, Br, Cl, F or C 1-6 alkoxy or when taken together with Z<SP>10</SP> represents a carbon-carbon double bond, -O-, -CH 2 -, -CCl 2 - or -CF 2 -, and the carboxylic esters, tetrahydropyranyl ethers and tetrahydrofuranyl ethers of the compounds having a free OH group, provided that (1) when Z<SP>3</SP> is H, then Z<SP>2</SP> is H, when Z<SP>7</SP> is H, then Z<SP>6</SP> is H, when Z<SP>11</SP> is H, then Z<SP>10</SP> is H, (2) when Z<SP>2</SP> is hydrogen then Z<SP>3</SP> is not Br, Cl or F, (3) when Z<SP>2</SP> together with Z<SP>3</SP> and Z<SP>6</SP> together with Z<SP>7</SP> are double bonds, each of R<SP>1</SP> and R<SP>2</SP> is methyl and one of R<SP>3</SP> or R<SP>4</SP> is methyl, then Z<SP>11</SP> is not hydrogen or, together with Z<SP>10</SP>, a double bond, and (4) when R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are methyl, R<SP>4</SP> is 4- methylpentyl and Z<SP>3</SP>, Z<SP>7</SP> and Z<SP>11</SP> are hydrogen then at least one of R<SP>7</SP> and R<SP>8</SP> is other than hydrogen. The amides are prepared (A) by treating an ester of the formula in which R<SP>5</SP> is C 1-6 alkyl, with an alkali metal salt of the amine NHR<SP>7</SP>R<SP>8</SP> in an inert organic solvent, or (B) by treating the acid halide corresponding to the acid moiety of the above ester with an amine NHR<SP>7</SP>R<SP>8</SP> in a non-aqueous, inert solvent. Any double bonds at the Z<SP>2</SP>-Z<SP>3</SP>, Z<SP>6</SP>-Z<SP>7</SP> or Z<SP>10</SP>-Z<SP>11</SP> positions in the starting ester or product-amide may be subjected to various reactions to introduce the alternative values of the groups Z, e.g. hydrogenation, epoxidation (using m-chloroperbenzoic acid), addition of fused -CH 2 - group (using CH 2 I 2 and a Zn/Cu couple), addition of fused -CF 2 - group (using trimethyltrifluoromethyl tin in the presence of NaI), addition of fused -CCl 2 - group (using phenyldichlorobromo mercury), hydration (using aqueous formic acid or H 2 SO 4 ), halogenation or hydrohalogenation. Selective introduction of an epoxide or fused -CH 2 - group at the Z<SP>2</SP>-Z<SP>3</SP> position may be achieved using hydrogen peroxide in aqueous alkali or dimethylsulphoxonium methylide base in dimethyl sulphoxide, respectively. Other derivatives are obtained by, e.g., reduction of the epoxide to give the mono-hydroxy compounds, cleavage of the epoxide ring using HClO 4 to give the vic-dihydroxy compounds and treatment of the unsaturated compounds with N-Br- or N-Cl-succinimide in an aqueous solvent to give the vic-Cl or Br-hydroxy compounds. The ethers and esters of compounds containing -OH groups are made by conventional etherification and esterification processes. The C 1-6 alkoxy derivatives can also be prepared by conducting any of the above processes yielding -OH compounds in the presence of a C 1-6 alkanol. The examples relate to the preparation of a large number of compounds particularly, derivatives of 3,7,11 - trimethyldodeca - 2,6,10 - trieriamide, 3,7,11 -trimethyltrideca - 2,6,10 - trienamide and 3,11 - dimethyl - 7 - ethyltrideca - 2,6,10 - trienamide. The amides are used as arthropod maturation inhibitors (see Division A5).
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57949066A | 1966-09-15 | 1966-09-15 | |
| US59019566A | 1966-10-28 | 1966-10-28 | |
| US59232466A | 1966-11-07 | 1966-11-07 | |
| US59466466A | 1966-11-16 | 1966-11-16 | |
| US60557866A | 1966-12-29 | 1966-12-29 | |
| US60556666A | 1966-12-29 | 1966-12-29 | |
| US61832167A | 1967-02-24 | 1967-02-24 | |
| US61833967A | 1967-02-24 | 1967-02-24 | |
| US61835167A | 1967-12-24 | 1967-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1209905A true GB1209905A (en) | 1970-10-21 |
Family
ID=27578872
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5586068A Expired GB1209905A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon amides and process for their production |
| GB3960167A Expired GB1209902A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon phosphonates and processes for their preparation |
| GB3300469A Expired GB1209906A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon halides and process for their production |
| GB3314669A Expired GB1209907A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon amines and process for their production |
| GB5585968A Expired GB1209904A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon alcohols and esters and ethers and process for their production |
| GB1716770A Expired GB1209908A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon alcohols |
| GB5585868A Expired GB1209903A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon esters and acids and process for their production |
| GB2183870A Expired GB1209909A (en) | 1966-09-15 | 1967-08-30 | A long chain hydrocarbon ketone |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3960167A Expired GB1209902A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon phosphonates and processes for their preparation |
| GB3300469A Expired GB1209906A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon halides and process for their production |
| GB3314669A Expired GB1209907A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon amines and process for their production |
| GB5585968A Expired GB1209904A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon alcohols and esters and ethers and process for their production |
| GB1716770A Expired GB1209908A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon alcohols |
| GB5585868A Expired GB1209903A (en) | 1966-09-15 | 1967-08-30 | Long chain hydrocarbon esters and acids and process for their production |
| GB2183870A Expired GB1209909A (en) | 1966-09-15 | 1967-08-30 | A long chain hydrocarbon ketone |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH494728A (en) |
| DE (2) | DE1618946A1 (en) |
| FR (1) | FR1551052A (en) |
| GB (8) | GB1209905A (en) |
| NL (1) | NL6712568A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1648870A (en) * | 1969-07-09 | 1971-12-23 | Fmc Corporation | Method of controlling insects and compostion therefor |
| CH569684A5 (en) * | 1972-03-10 | 1975-11-28 | Givaudan & Cie Sa | |
| JPS52131507A (en) * | 1976-04-24 | 1977-11-04 | Sankyo Co Ltd | Polyprenyl derivatives |
| CH625676A5 (en) * | 1977-07-19 | 1981-10-15 | Ciba Geigy Ag | |
| US4230726A (en) * | 1979-06-29 | 1980-10-28 | The United States Of America As Represented By The Secretary Of Agriculture | Control of parasitic mites with alkyl amines |
| US4456603A (en) * | 1979-08-14 | 1984-06-26 | Eisai Co., Ltd. | Polyprenylcarboxylic acid amides useful for treating liver dysfunction |
| JPS57192342A (en) * | 1981-05-18 | 1982-11-26 | Nisshin Flour Milling Co Ltd | Isoprenylamine derivative |
| CN113999096B (en) * | 2021-11-29 | 2023-05-30 | 万华化学集团股份有限公司 | Method for synthesizing 6-methyl-5-octene-2-ketone by condensation hydrogenation |
-
1967
- 1967-08-30 GB GB5586068A patent/GB1209905A/en not_active Expired
- 1967-08-30 GB GB3960167A patent/GB1209902A/en not_active Expired
- 1967-08-30 GB GB3300469A patent/GB1209906A/en not_active Expired
- 1967-08-30 GB GB3314669A patent/GB1209907A/en not_active Expired
- 1967-08-30 GB GB5585968A patent/GB1209904A/en not_active Expired
- 1967-08-30 GB GB1716770A patent/GB1209908A/en not_active Expired
- 1967-08-30 GB GB5585868A patent/GB1209903A/en not_active Expired
- 1967-08-30 GB GB2183870A patent/GB1209909A/en not_active Expired
- 1967-09-13 DE DE19671618946 patent/DE1618946A1/en active Pending
- 1967-09-13 DE DE19671793729 patent/DE1793729A1/en active Pending
- 1967-09-14 NL NL6712568A patent/NL6712568A/xx unknown
- 1967-09-15 FR FR1551052D patent/FR1551052A/fr not_active Expired
- 1967-09-15 CH CH1292167A patent/CH494728A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL6712568A (en) | 1968-03-18 |
| FR1551052A (en) | 1968-11-18 |
| GB1209904A (en) | 1970-10-21 |
| GB1209902A (en) | 1970-10-21 |
| GB1209903A (en) | 1970-10-21 |
| DE1618946A1 (en) | 1972-06-08 |
| GB1209906A (en) | 1970-10-21 |
| GB1209907A (en) | 1970-10-21 |
| GB1209908A (en) | 1970-10-21 |
| CH494728A (en) | 1970-08-15 |
| GB1209909A (en) | 1970-10-21 |
| DE1793729A1 (en) | 1973-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |