GB677199A - Improvements in or relating to the preparation of organic compounds involving chain reaction mechanisms - Google Patents
Improvements in or relating to the preparation of organic compounds involving chain reaction mechanismsInfo
- Publication number
- GB677199A GB677199A GB18066/50A GB1806650A GB677199A GB 677199 A GB677199 A GB 677199A GB 18066/50 A GB18066/50 A GB 18066/50A GB 1806650 A GB1806650 A GB 1806650A GB 677199 A GB677199 A GB 677199A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- hydrocarbons
- esters
- carbon
- compounds
- 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
- 238000006243 chemical reaction Methods 0.000 title abstract 7
- 150000002894 organic compounds Chemical class 0.000 title abstract 4
- 230000007246 mechanism Effects 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 8
- 239000002253 acid Substances 0.000 abstract 6
- -1 vinyl aromatic compounds Chemical class 0.000 abstract 6
- 150000007513 acids Chemical class 0.000 abstract 5
- 229930195733 hydrocarbon Natural products 0.000 abstract 5
- 150000002430 hydrocarbons Chemical class 0.000 abstract 5
- 229920000642 polymer Polymers 0.000 abstract 5
- 229920002367 Polyisobutene Polymers 0.000 abstract 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001299 aldehydes Chemical class 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002170 ethers Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 2
- 206010001497 Agitation Diseases 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 2
- 238000013019 agitation Methods 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000026030 halogenation Effects 0.000 abstract 2
- 238000005658 halogenation reaction Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 abstract 2
- 229920001567 vinyl ester resin Polymers 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- VRWWJIACGVONTQ-UHFFFAOYSA-N 2-phenylethylsulfanylbenzene Chemical compound C=1C=CC=CC=1SCCC1=CC=CC=C1 VRWWJIACGVONTQ-UHFFFAOYSA-N 0.000 abstract 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 238000007259 addition reaction Methods 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000004651 carbonic acid esters Chemical class 0.000 abstract 1
- 230000021523 carboxylation Effects 0.000 abstract 1
- 238000006473 carboxylation reaction Methods 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 238000000227 grinding Methods 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000009775 high-speed stirring Methods 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 238000004898 kneading Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000003801 milling Methods 0.000 abstract 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000002905 orthoesters Chemical class 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000012258 stirred mixture Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/10—Cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- 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
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- 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
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- 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
- C07F9/50—Organo-phosphines
- C07F9/52—Halophosphines
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The preparation of organic compounds from dissimilar reactants capable of reacting through a chain reaction mechanism in the presence of free atoms or free radicals is effected by subjecting a mixture of the reactants with a linear polymer (including cellulose derivatives and condensation resins) having a molecular weight of at least 104 to an agitation treatment sufficient to degrade the polymer and thus form the free radicals necessary to initiate the desired reaction. The agitation, which may be carried out in the presence or absence of a solvent or diluent, may consist of intensive shaking, high-speed stirring, milling, kneading, grinding, the use of gear and piston pumps, treatment with ultrasonic radiation or passage through filters and capillaries. Suitable linear polymers, the molecular weight of which may range up to 9 X 106 but is preferably between 7.5 X 104 and 7 X 106, are cellulose esters and ethers, linear alkyd resins, linear polyamides and polymers of the carbonic acid esters of unsaturated diols (examples of all of which are given), linear phenol-aldehyde condensation products, and particularly homopolymers, copolymers and interpolymers of polymerizable olefinic compounds (e.g. of unsaturated acids and their derivatives, tetrahaloethylenes, butadienes, vinyl aromatic compounds and vinyl esters, ethers and ketones, and especially of vinylidene halides, acrylic acid and a -alkylacrylic acids in which the alkyl radical contains 1-4 carbon atoms, their esters with alkanols containing 1-6 carbon atoms in the molecule, and their nitriles, vinyl esters of saturated monocarboxylic acids containing 1-6 carbon atoms in the molecular and of halogen acids, isobutylene, styrene and a -methylstyrene). Chain reactions to which the process is applicable include: (a) addition reactions of halogens, hydrogen halides, polyhalogenated saturated aliphatic hydrocarbons, mercaptans, phosphorus trichloride or alkali metal bisulphites with ethylenically unsaturated organic compounds preferably containing at least one CH2=C< group (especially propene, butene-1, octene-1, styrene, ethyl acrylate, allyl alcohol, allyl chloride or vinyl chloride); (b) substitution halogenations (especially sidechain halogenation of araliphatic compounds); (c) sulphonation of hydrocarbons with sulphuryl chloride (usually in the side chain in the case of araliphatic hydrocarbons); (d) carboxylation of hydrocarbons by the action of oxalyl chloride; (e) reaction of carbon disulphide with hydrocarbons to produce thio-substituted products; (f) oxidation reactions (e.g. of alcohols to aldehydes, aldehydes to acids, acids to peracids, hydrocarbons to peroxides or sulphites to sulphates); (g) telomerization reactions, e.g. of olefines with aliphatic halogen-containing compounds, with hydrogen chloride or with saturated organic compounds containing only carbon, hydrogen and oxygen (e.g. alcohols, aldehydes, ketones, acids, esters, orthoesters, acid anhydrides, ethers or acetals). In examples: (1) carbon tetrabromide and styrene are shaken with polystyrene and carbon tetrachloride to produce 1 : 1 : 1 : 3-tetrabromo-3-phenylpropane; (2) carbon tetrachloride and octene-1 are rapidly stirred with polyisobutylene to form 1 : 1 : p 1 : 3 - tetrachlorononane; (3) toluene and bromine are shaken with polyisobutylene to give benzyl bromide; (4) oxygen is bubbled through a rapidly stirred mixture of cumene, polyisobutylene and cyclohexane, producing cumene hydroperoxide; (5) cyclohexane is chlorinated by shaking it with chlorine and polyisobutylene; (6) a mixture of phenyl mercaptan, styrene and methyl methacrylate polymer is repeatedly passed through a narrow orifice, yielding 1-phenyl-2-phenylmercaptoethane. Lists of additional starting materials for the various types of reaction enumerated above are given.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US677199XA | 1949-07-19 | 1949-07-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB677199A true GB677199A (en) | 1952-08-13 |
Family
ID=22077928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB18066/50A Expired GB677199A (en) | 1949-07-19 | 1950-07-19 | Improvements in or relating to the preparation of organic compounds involving chain reaction mechanisms |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE847150C (en) |
GB (1) | GB677199A (en) |
NL (1) | NL75849C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0995734A1 (en) * | 1998-10-20 | 2000-04-26 | Nippon Shokubai Co., Ltd. | Method for production of halogen-containing aromatic compound |
-
1950
- 1950-07-13 DE DEN1485A patent/DE847150C/en not_active Expired
- 1950-07-19 NL NL154908A patent/NL75849C/xx active
- 1950-07-19 GB GB18066/50A patent/GB677199A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0995734A1 (en) * | 1998-10-20 | 2000-04-26 | Nippon Shokubai Co., Ltd. | Method for production of halogen-containing aromatic compound |
US6288290B1 (en) | 1998-10-20 | 2001-09-11 | Nippon Shokubai, Co., Ltd. | Method for production of halogen-containing aromatic compound |
US6433231B2 (en) | 1998-10-20 | 2002-08-13 | Nippon Shokubai Co., Ltd. | Method for production of halogen-containing aromatic compound |
Also Published As
Publication number | Publication date |
---|---|
NL75849C (en) | 1954-04-15 |
DE847150C (en) | 1952-08-21 |
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