Miscellaneous US Patents



This page has been set up differently from the first three patent collection pages. Rather than make a page for each group of patent numbers, a number of groups have been put into one page to make it easier to add more patents to the list later. An index of links to each group of patents is included in the same page. Patents are grouped according to US patent class/subclass where they were found during the search and/or computer database keywords used and/or by chemical process or other chemical subject matter of interest. More patents will be added to the list as I find them.


Index

1. Formation of epoxides, diols or ketones from olefins
2. Direct amination of olefins
3. Yeast
4. ArOR, Alternatives to dimethyl sulfate
5. NaBH4 patents
6. Patents disclosing Friedel-Crafts reactions

Patents

1. Formation of epoxides, diols or ketones from olefins, ie. Wacker, peracid, etc. and patents relating to those processes:

568/311

3028398 Peracetic acid process for making P2Ps from allyl benzenes, isoeugenol --> 4-hydroxy-3-methoxy-P2P in examples 1 and 3, isosafrole --> 3,4-MDP2P in example 2

3231620 Wacker process using palladium chloride and hydrogen peroxide



Other peracetic acid patents

4273943 Peracetic acid process, note use of NaHSO3 for destroying excess CH3COOOH

4337360 Peracetic acid process, note use of NaHSO3 for destroying excess CH3COOOH

4393242 Peracetic acid process, note use of NaHSO3 for destroying excess CH3COOOH


423/281

1076039 sodium perborate (NaBO3) + H2O --> NaBO2 + H2O2

5462692 sodium acetyl peroxyborate from sodium perborate and acetic acid. When sodium acetyl peroxyborate is contacted with water peracetic acid is formed



568/860

2701813 Wacker-like process using cobalt or manganous acetate catalyst and O2

1982545 I2 + H2O + ethylene --> glycol

2304064 CH3COOH + H2O2 --> peracetic acid + H2O at 80-85 degrees C 1 hr, cool, add alkene

2071395 I2, Mn salts, ferrous salts, persalts

2510905 use of ammonium persulfate and acetic acid for making diols from olefins

3928474 I2 + ethylene, autoclave

4008286 Cu and Fe, Br-

4045500 I2 + H2O + ethylene, autoclave

4195190 I2 + H2O + ethylene with Br compound

4202995 Fe, Cu, Br-, I-

4390738 Cu peroxide, from Cu salt and H2O

4562299 Na metabisulfate destroys H2O2

5210336 O2, CO2, CaI2, CuI, Cu2O on MnO2

5268493 CH3COOOH + catalyst

5850086 Fe complexes enhance bleaching and epoxidation



568/400

3432556 CH2=CH-CH3 + Hg(NO3)2 ---Fe3+---> CH3COCH3 + Hg + HNO3



568/401

3965185 Pd Wacker with NH4NO3 maintains catalyst active for continuous conversion of olefin to carbonyl compound

4419525 Regeneration of Wacker type catalysts



568/310

4731482 allyl benzene Wacker, safrole example 1



568/427

4929765 styrene oxide/glycol --> phenylacetaldehyde



568/458

2613223 WO3 or MoO3 and H2O2, Wacker-like



568/859

1594608 styrene --> glycol uses NaOCl and CO2



562/2

2802025 CH3COOH + H2O2 ---H2SO4---> peracetic acid, 12-16 hr equalibrium column 2 of patent

5098598 stability of peracetic acid



562/6

4168274 continuous process for the production of a peracid in an organic solvent; epoxidation


2. Direct amination of olefins

564/485

2984687 low pressure

2397705 NH3 + propylene, cobalt catalyst 650-800 degrees F

2518528 NaNHR + -C=C- ---> amine

4827031 NH4X catalyst 170-450 degrees C, 1 atm-8500 psi

4929758 zeolite catalysts

4937383 NH4(SO4) catalyst, autoclave, autogenous pressure

2501509 Na, isopropylamine

2501556 higher C's less reactive, Na

2627526 RR'NH ---H2O2---> RR'NOH possibly relevant to CAT

4454321 C 2-18 column 1 lines 41-42, salt/coordination compound Ru, Fe, Pd, Pt, Rh propylene column 2 line 6, salt can be halide, nitrate, sulfate, phosphate, formate, acetate or hydrates (see patent)

5107027 clay catalysts

5900508 zeolite catalysts



564/374

2449644 phenethylamines by direct amination


102/367

3889600 1-(2-(Phenyl-lower-alkyl)-Aziridines Munition Payload


3. Reactions involving yeast

568/315

1962476 benzaldehyde ---yeast---> phenyl-CHOH-CO-CH3

4. ArOR, Alternatives to dimethyl sulfate
from class 568 subclasses 628, 630, 648, 654 and 657 on methods of making aryl-alkyl ethers, and class 558 subclasses 20, 21, 38, 39, 40, 41 and 43 on various ways of making alkyl sulfates and alkyl hydrogen sulfates.

2490842 anisole from phenol and CH3MSO4 where M can be a metal such as sodium or potassium or it can be NH4+. Example 2 uses methyl sodium sulfate to make anisole from phenol.

2031719 on condensing phenol and alcohols with ZnCl2.

1411215 Na2SO4

2062454 RHSO4 + MCl --> RMSO4 + HCl (M = metal)

2176005 RCaSO4

2688035 use of alkali carbonates

3305578 R(amine)SO4, ie. R(R'NH2)SO4

4146551 Mg salt of RHSO4

3829457 RMSO4 from ROH & SO2 and O2

1599119 ferrous and cuprous catalyst for ethylene

1589372 ethylene catalysts

1574796 ethylene catalysts

1478498 ZnCl2

1484249

1641005 SO2Cl2 & alcohol --> alkyl sulfates

1998411 RMSO4

3024263 2NaHSO4 + C2H5OH = C2H5HSO4 + Na2SO4 + H2O ; Na2SO4 dehydration

3047604 Na2SO4

3232976 interesting aspirator pump apparatus

2052745 refining anethole

2233080 ArOH + RX + MOH --> ArOR + MX + H2O (M = metal)

2516412 syringaldehyde, Mep for MeO-

797024 CH3Cl

1801901 EtCl

2031719 ZnCl

2070848 RCl

2103736 phospho Mo/W catalyst

2487832 dimethyl ether used to make ArOMe

2490842 M(Me)SO4, (M = metal)

2727926 ØCOOH --> ØOH

3911022 ØOH + ester --> ØOR

5817886 phenol + MeOH + catalyst

4918241 aryl iodides --> phenols

4765455 phenols + alcohols, sulfated oxide of Cr/Mo/mixture catalyst

4675454 phenols + alcohols, sulfated oxide of Cr/Mo/mixture catalyst

4611084 phenols + alcohols, sulfated oxide of Mn/Re/mixture catalyst

4638098 phenols + alcohols, sulfated oxide of Zn/Cd/Hg/mixture catalyst

2067960 hydroquinone + RX in ROH

2235884 hydroquinone + RX in ROH

2439375 3,4-MD-phenyl --Ni--> phenol

2676947 dimethoxystyrene

2694736 Hg and Ni catalyst

2782239 alcohols & catalyst, hydroquinone and alumina-silicate catalyst 550º F

2847477 Hg acetate catalyst


5. NaBH4 patents
from US class 423 subclasses 286, 287 and 288

3734842 electrolytic synthesis of NaBH4 from NaBO2

2942935 MgB2 --> borohydrides

3077376 borax to borohydrides

2898184 apparatus with three neck flask, Wood's metal bath

3253884 borohydride H2 source

3379511 NaBH4

3458531 IR spectra

3637516 cyanoborohydride

3993732 recycling LiBH4

5294423 a mixture of an alkali metal hydride, boric anhydride and a hydrogenation catalyst such as Raney nickel is raised to a temperature of 250.degree. to 300.degree. C. under a hydrogen atmosphere.

6251349 Method of fabrication of complex alkali metal hydrides


Here's some boride patents. The first one is on an aluminothermic process.

3016288 aluminothermic process

1858413 calcium boride

2893841 MgB4

3253886 interesting apparatus

3379647 borides and carbides

3392059 Ni and NaBH4

4604368 AlB2


4038290 olefins to epoxides using a boride catalyst

6. Patents disclosing Friedel-Crafts reactions
from US patent class 585 subclasses 462, 446 and 467:

3676515 aluminum mercury alloy

3381050 aluminum copper alloy

1972956 hydrated ferric chloride as catalyst

3678122 use of allyl halide and copper halide catalyst

4551573 AlX3 and I2

1216174 AlCl3 and Fe turnings, appears to produce higher yield of monoalkylated benzene, ie. toluene in 97.5% yield

patents from class 502:

2542610 highly active Friedel-Crafts double salts

2853533 clay attenuated AlCl3

1941884 X --> HX, Al --> AlX3

2057306 Al --> AlCl3

2271299 AlCl3 and support

2309263 AlX3 and support

2370788 Al-Hg --> AlCl3, aluminum carbide --> AlCl3


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