GB591632A - Synthesis of organic halogen compounds from a lower boiling tertiary compound and mono-olefinic compound both of which are halogenated - Google Patents
Synthesis of organic halogen compounds from a lower boiling tertiary compound and mono-olefinic compound both of which are halogenatedInfo
- Publication number
- GB591632A GB591632A GB22615/44A GB2261544A GB591632A GB 591632 A GB591632 A GB 591632A GB 22615/44 A GB22615/44 A GB 22615/44A GB 2261544 A GB2261544 A GB 2261544A GB 591632 A GB591632 A GB 591632A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- tert
- mono
- aluminium
- halogenated
- 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
- 150000001875 compounds Chemical group 0.000 title abstract 6
- 238000009835 boiling Methods 0.000 title abstract 3
- 150000002896 organic halogen compounds Chemical class 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 16
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 abstract 16
- 239000003054 catalyst Substances 0.000 abstract 10
- 239000001282 iso-butane Substances 0.000 abstract 8
- 150000004820 halides Chemical class 0.000 abstract 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 abstract 6
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 5
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 abstract 4
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 4
- 239000004411 aluminium Substances 0.000 abstract 4
- 229910052782 aluminium Inorganic materials 0.000 abstract 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 4
- -1 butyl halide Chemical group 0.000 abstract 4
- 150000002576 ketones Chemical class 0.000 abstract 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 150000001298 alcohols Chemical class 0.000 abstract 3
- 150000001299 aldehydes Chemical class 0.000 abstract 3
- 150000001336 alkenes Chemical class 0.000 abstract 3
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Substances Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 abstract 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 abstract 3
- 150000002366 halogen compounds Chemical class 0.000 abstract 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 3
- RQXXCWHCUOJQGR-UHFFFAOYSA-N 1,1-dichlorohexane Chemical compound CCCCCC(Cl)Cl RQXXCWHCUOJQGR-UHFFFAOYSA-N 0.000 abstract 2
- RJTBLHMOHNHTTP-UHFFFAOYSA-N 1,2-dichloro-4,4-dimethylpentane Chemical group CC(C)(C)CC(Cl)CCl RJTBLHMOHNHTTP-UHFFFAOYSA-N 0.000 abstract 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract 2
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 abstract 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 235000013844 butane Nutrition 0.000 abstract 2
- 150000001805 chlorine compounds Chemical class 0.000 abstract 2
- 150000001934 cyclohexanes Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 229910001507 metal halide Inorganic materials 0.000 abstract 2
- 150000005309 metal halides Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical group CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 abstract 2
- 238000004064 recycling Methods 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 238000006467 substitution reaction Methods 0.000 abstract 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 2
- YUHZIUAREWNXJT-UHFFFAOYSA-N (2-fluoropyridin-3-yl)boronic acid Chemical class OB(O)C1=CC=CN=C1F YUHZIUAREWNXJT-UHFFFAOYSA-N 0.000 abstract 1
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 abstract 1
- LEEOVPURCDWZOP-UHFFFAOYSA-N 1,1-dichloro-2,3,3-trimethylbutane Chemical compound ClC(Cl)C(C)C(C)(C)C LEEOVPURCDWZOP-UHFFFAOYSA-N 0.000 abstract 1
- BLRPQFOUUPCTED-UHFFFAOYSA-N 1,1-dichloro-3,3-dimethylbutane Chemical compound CC(C)(C)CC(Cl)Cl BLRPQFOUUPCTED-UHFFFAOYSA-N 0.000 abstract 1
- OQYNFBPKTVQOKO-UHFFFAOYSA-N 1,1-dichlorooctane Chemical class CCCCCCCC(Cl)Cl OQYNFBPKTVQOKO-UHFFFAOYSA-N 0.000 abstract 1
- MHIIWIBHPIGIAY-UHFFFAOYSA-N 1,2-dichloro-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(Cl)CCl MHIIWIBHPIGIAY-UHFFFAOYSA-N 0.000 abstract 1
- XUTRWWGNOKAEBC-UHFFFAOYSA-N 1,2-dichloro-4,4-dimethylhexane Chemical compound CCC(C)(C)CC(Cl)CCl XUTRWWGNOKAEBC-UHFFFAOYSA-N 0.000 abstract 1
- UOORRWUZONOOLO-UHFFFAOYSA-N 1,3-dichloropropene Chemical group ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 abstract 1
- JZIXDUBILJGMDD-UHFFFAOYSA-N 1-chloro-3,4-dimethylpentane Chemical compound CC(C)C(C)CCCl JZIXDUBILJGMDD-UHFFFAOYSA-N 0.000 abstract 1
- RKAMCQVGHFRILV-UHFFFAOYSA-N 1-chlorononane Chemical class CCCCCCCCCCl RKAMCQVGHFRILV-UHFFFAOYSA-N 0.000 abstract 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 abstract 1
- MJMQIMYDFATMEH-UHFFFAOYSA-N 2-chloro-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)Cl MJMQIMYDFATMEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- DLEUJDNDBMGGLN-UHFFFAOYSA-N 4,4-dichloroheptane Chemical class CCCC(Cl)(Cl)CCC DLEUJDNDBMGGLN-UHFFFAOYSA-N 0.000 abstract 1
- MGSGWAXIEMEWCQ-UHFFFAOYSA-N 4-chloroheptane Chemical compound CCCC(Cl)CCC MGSGWAXIEMEWCQ-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- USQOVYLRWBOSQC-HNNXBMFYSA-N CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O Chemical compound CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O USQOVYLRWBOSQC-HNNXBMFYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 abstract 1
- 239000012190 activator Substances 0.000 abstract 1
- 150000007824 aliphatic compounds Chemical class 0.000 abstract 1
- 150000001348 alkyl chlorides Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 abstract 1
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical class Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 abstract 1
- 150000001649 bromium compounds Chemical class 0.000 abstract 1
- KOYGZROXUOTUEE-UHFFFAOYSA-N butane;but-1-ene Chemical compound CCCC.CCC=C KOYGZROXUOTUEE-UHFFFAOYSA-N 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000010924 continuous production Methods 0.000 abstract 1
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 abstract 1
- 150000001925 cycloalkenes Chemical class 0.000 abstract 1
- 210000003298 dental enamel Anatomy 0.000 abstract 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 abstract 1
- 238000005108 dry cleaning Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 150000002222 fluorine compounds Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 150000004694 iodide salts Chemical class 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 238000005120 petroleum cracking Methods 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000098 polyolefin Polymers 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
- 239000005418 vegetable material Substances 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
-
- 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
- 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
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- 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
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
- C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US591632XA | 1943-10-12 | 1943-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB591632A true GB591632A (en) | 1947-08-25 |
Family
ID=22021235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22615/44A Expired GB591632A (en) | 1943-10-12 | 1944-11-15 | Synthesis of organic halogen compounds from a lower boiling tertiary compound and mono-olefinic compound both of which are halogenated |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB591632A (enrdf_load_stackoverflow) |
| NL (1) | NL67945C (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2610978A (en) * | 1949-12-02 | 1952-09-16 | Union Carbide & Carbon Corp | Production of halogen containing organic compounds of phosphorus |
| WO2000010954A1 (en) * | 1998-08-20 | 2000-03-02 | The Nutrasweet Company | Preparation of 3,3-dimethylbutyraldehyde from a tert-butyl cation precursor, vinyl chloride and an acidic catalyst |
| WO2000015592A1 (en) * | 1998-09-17 | 2000-03-23 | The Nutrasweet Company | Synthesis and purification of 3,3-dimethylbutyraldehyde via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane |
| WO2016044256A1 (en) * | 2014-09-16 | 2016-03-24 | Reaction35, LLC | Production of isobutylene, isoamylene, or alkylates from mixed alkanes |
-
0
- NL NL67945D patent/NL67945C/xx active
-
1944
- 1944-11-15 GB GB22615/44A patent/GB591632A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2610978A (en) * | 1949-12-02 | 1952-09-16 | Union Carbide & Carbon Corp | Production of halogen containing organic compounds of phosphorus |
| WO2000010954A1 (en) * | 1998-08-20 | 2000-03-02 | The Nutrasweet Company | Preparation of 3,3-dimethylbutyraldehyde from a tert-butyl cation precursor, vinyl chloride and an acidic catalyst |
| WO2000015592A1 (en) * | 1998-09-17 | 2000-03-23 | The Nutrasweet Company | Synthesis and purification of 3,3-dimethylbutyraldehyde via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane |
| WO2016044256A1 (en) * | 2014-09-16 | 2016-03-24 | Reaction35, LLC | Production of isobutylene, isoamylene, or alkylates from mixed alkanes |
| US10040734B2 (en) | 2014-09-16 | 2018-08-07 | Reaction 35, Llc | Production of isobutylene, isoamylene, or alkylates from mixed alkanes |
Also Published As
| Publication number | Publication date |
|---|---|
| NL67945C (enrdf_load_stackoverflow) |
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