Check out Atomic Rocket for a tribute to Heinlein and Clarke and a repository of graphics and themes of space opera. Really a fantastic resource for science fiction writers.
Bruce Schneier interviews TSA Administrator Kip Hawley. Sounds like we’ll be taking our shoes off for quite a while.
Filipino prisoners do the Algorithm March. The Algorithm March at the airport.
I know it is hard to fathom, but as an undergrad the Gaussling wasn’t automatically the favorite of all the faculty in the chemistry department. I had been independent for 4 years prior to my matriculation into the fabulous world of chemistry. With independence comes a strong dash of unruliness, an attribute that irritates those around me to this day.
One faculty member who was especially irritated by a precocious bugger like me was a particular analytical professor. He was and is to this day a bit of a fuss budget. But, he was and is a pretty smart guy too. One day in an unusually tedious analytical lab he was expounding on what an analyst could expect to be doing out in the world. As a part of an attempt to clue us in to the “real world”, he pointed out that one day in the not-so-distant future we would be writing procedures for others to follow. His prophetic allusion to job descriptions struck me as an interesting comment.
Increasingly, I find myself synthesizing work structure and writing lab procedures for others to follow, just as this analyst had predicted.
Which brings up another point. One road rage trigger out in career space is the nimrod manager who himself cannot synthesize ideas or plans, but somehow has been blessed with veto power over those who do. Sometimes the only realistic solution is to leave the company.
It is possible to be so compliant in the corporate world that you labor against you own best interests. On the windward side we have HR ever turning the screws by more tightly narrowing job descriptions, freezing out degrees of freedom. Eventually they have the option of discontinuing narrow positions by eliminating specialists.
If you have ever taken a personality test battery as part of career advancement, you’ll see what psychologists have been up to since they collectively got bored with rat mazes and Skinner boxes and discovered marketing. In many corporations certain profiles are culled and steered up the ladder. There is logic to this, obviously, but I retain a conceit that merit is demonstrated by deeds. Organizations who apply scientific Human Resource management now presume to remove growth opportunity with psychological instruments that are sold to them by sales people. I have been told by straight-faced practitioners that they themselves do not understand the test theory or methodologies, much less profess a clue as to the statistical limitations.
Unfortunately, my dear old professor didn’t warn us about this aspect of career space.
Good lord. What a bad year for NASA. First astronaut Lisa Nowak goes non-linear in a fit of lunacy that even National Lampoon would claim is over the top. Now there is talk of sabotage and drunken astronauts.
Intrepid, hard drinking stick and rudder aviators have long been part of the lore of flight. Remember the Happy Bottom Riding Club? The image of the astronauts as a preening, squeeky clean corps of orbiting sunday school teachers is the result of years of pathetic NASA propaganda. It is an absurd fiction and it needs to stop.
There is no doubt that astronauts as a group are disinclined to do anything that would negatively affect their flight status and the likelihood an inebriated astronaut would adversely affect a mission is between slim and none. The buzz over Paris Hilton has run its course and the news business is looking for more titillation to maintain the national slack-jaw coefficient.
NASA should spend its resources trying to find more compelling reasons to maintain manned spaceflight rather than ginning up SOP‘s for greater oversight of astronaut blood alcohol levels.
The cover story of the latest issue of C&EN is concerned with the “Global Top 50” chemical companies. To nobody’s surprise, Dow, BASF, and Royal Dutch Shell occupy the top three positions again this year. The dollar numbers are impressive enough, but have a look at the column on the far right of the table on page 14- “Return on Chemical Assets”. This is an important column. It signals which operators can squeeze the greatest value out of their plants. The winner in this column is 11th ranked SABIC with a 30 % return on assets and reported 43 % operating profit margin. Compare that with 2nd ranked Shell (11 and 9 %) and 3rd ranked ExxonMobil (6 and 2 %). There has to be a story there.
On page 16 of the cover story, the figure titled “Narrowing In” shows the market coverage over several decades. It is clear that the big chemical players exited the pharmaceutical business in favor of chemicals. One of the euphamisms is that this is a return to core competencies. A more cynical comment might be that the players fled from core incompetencies. There is truth in both views.
Another table shows R&D spending as % of chemical sales. These numbers have been flat across the industry since Y2000. An investor might look at this and conclude that the players are conservative, and that would be right. Chemical industry does tend to be conservative. But a chemical catalog president would look at the numbers and proclaim that this is indicative of a cash cow for sales of specialty R&D chemicals. OK, the growth is flat. But it is safe.
One of the fun “burdens” of blogging is the constant pressure to write new posts with new content. Since I am not Jacques-Yves Cousteau or Henry Kissinger, I have to thrash around for ideas that are compelling yet not in conflict with confidentiality issues related to my career. I have much to say about many fascinating chemistries in diverse industries that, owing to confidentiality, I’ll have to take to the grave. No doubt there are many other bloggers out there who are in the same pickle.
As I get further into this activity I am constantly impressed with the number and variety of really bright people out there writing blogs. I have tried to highlight a few of them on the Blogroll of this site. The flow of good blogs, commercial or amateur(ish), continues to accelerate.
What is disappointing about blogging is the continued growth of snarky, half-assed commentary. I have been fortunate on this blog to receive very thoughtful and insightful comments, and for that I am grateful. I have only edited out a handful of inappropriate responses. I suspect this is due to the specialized nature of this blog, modest visitation rate, and its content. The blogs with the most negative or ill conceived comments seem to be those that are visited by a broader group of participants.
As we move forward with this form of communication, it becomes apparent to me that the need for edited content is as great as ever. Take this blog for example. I could easily take the encyclopedic approach and spend all of my efforts writing pedagogical content. Even if someone liked such content, there would always be the nagging issue of credibility. Without good editors and gate keepers, factual content and editorializing would inevitably meld into a dried brick of pedagogical poundcake that no one could trust. In fact, one could not even trust that the poundcake would be the same from one day to the next.
I’m not sure how we’ll deal whith the problem of unedited content. I am alarmed at the amount of reliance on the www content that I am hearing from university friends and from public school teachers. I think we should all revisit the library for an update on what makes information credible.
By 12:15 AM saturday we had copies of the latest and final installment of the J.K. Rowling franchise, Harry Potter and the Deathly Hallows. It was an evening of standing-room-only at the local Borders bookstore, elbow to elbow with muggle Potter enthusiasts. Many were in costume but all were anxious to get their copy of the book and once again enter the magical world of Harry Potter.
As we made our way to the parking lot it became apparent that flyers had been affixed under the wiper blades of cars outside the store. Under the orange afterglow of the evening we could see the colorful flyers festooned with Potter graphics and the congratulations to the reader on their early purchase of the book. Then the flyer went on to reveal the the fate of the characters! These flyers were SPOILERS!#&*@! It was an unthinkable act of desecration forced upon innocent followers of the story.
For the love of God!! What kind of fiendish mind could conceive of this heinous act?! Someone printed these flyers and then, when the moment was right, quietly planted them when anticipation was at its highest. What mothers child could do this? Who are these sick puppies, these bomb throwing literary terrorists who could execute such a felonious theft of innocence? Think of the children.
Well, anyway, we intercepted the flyer and tucked it away to protect some unsuspecting citizen from picking up this booby-trap from the ground and reading it. Unfortunately, Th’ Gaussling suffered some acute exposure to this bit of printed poison. Bummer.
This is a long and drawn out post on intellectual property, possibly not suitable for those with attention deficit disorder.
<<<< Warning! This post may cause somnolence or ED. >>>>
In this post, I have attempted to make a case that current practice in granting US patents contains a flaw that may be counter to the public interest. See what you think.
In my view, there is a curious discontinuity between the practice of determining obviousness and the allowance of Markush claims in US Patent law. A Markush claim in the context of chemistry refers to a claim of a generic chemical structure defined by symbols that represent sets of functionally related moieties or structures. Very often a core moiety is defined and one or more substructure symbols or other symbols representing various chemical elements are attached.
As an example of Markush claims, consider US 4,237,133, an expired Pfizer patent dated December 2, 1980. I “randomly” found this patent by searching under the key words “bromination” and “aromatics” at the USPTO website. This patent is illustrative of the point I want to make and my use here is not meant to defame or otherwise irritate Pfizer. I have no connection to this art in any sense.
The ‘133 patent is a fairly ordinary chemical patent. It contains 10 claims- two independent claims (claims 1 and 10) and 8 dependent claims that are ultimately based on claim 1. Claim 1 is a Markush claim that defines a set of chemical compositions that the PTO has allowed the assignee, Pfizer, to have a legal monopoly on. Basically, Pfizer was allowed two varieties of claims: a) a composition of matter, and b) the process of producing analgesia in mammals, based on the compounds in claim 1.
Claims 2 through 8 are a series of “necking down” refinements to more preferred embodiments that are especially meaningful to the assignee. Preferred embodiments are specific features that the assignee apparently wished to have clear definition to avoid ambiguity.
A patent must be “enabling”. That is, the patent must teach enough of the art to allow a Phosita the chance to see and avoid the patented art. This is the whole purpose of publishing a patent. If the state is to grant exclusive rights to a composition of matter or a process, then the public needs to have a fair chance to avoid infringement. The content ahead of the claim section is called the specification and it must contain information that, when combined with the claims, enable a reader to understand exactly what is being claimed and under what constraints. In the case of composition of matter, it is common to disclose the procedures used to make the composition so there is no doubt by Phosita as to what conditions lead to the claimed material.
The patent claims a tricyclic ring systen festooned with functionalities, some of which are variable. Variable groups are R1, R2, R3, R4, Z, and W. R1 is further subdivided into other moieties, some bearing variable groups R’ and R” and appended to a chain bearing p methylene units -(CH2)-, where p may range from 0 to 4 . Z and W are also comprised of features subject to variability.
The point is that the set of all claimed species is quite large. Not surprisingly, one could easily wander into claimed composition space because, ordinarily, CAS does not capture all of the compositions from the Markush claim.
It is not required that the applicant prove that they have prepared each permutation in the set of claims, nor is it required that the enabling procedures specifically address each claimed species. The ‘133 patent has 43 procedures, many of which are for intermediate compounds, at best a number that falls far short of the entire set of claimed compositions. Usually, it is sufficient for illustrative examples or preferred embodiments to be set forth in procedure.
If you think of each group as a spatial dimension, a generic core species with n variable groups essentially maps out a set of structures occupying a kind of n-dimensional space, subject to specific exclusions. When the variable groups are defined as alkyl, aryl, alkoxy, alkenyl, etc., the number of claimed species can be quite large due to the vast number of possible combinations of groups. Even limited ranges, i.e., R = C20 alkyl, etc., can result in huge collections of claimed species owing to structural isomerism.
The concept of obviousness in patent prosecution is one of the most vexing and mercurial ideas I can think of. The code is set forth in 35 USC 103. A patent attorney will caution that there is no hard and fast universal definition in advance of litigation because what really matters is how a judge decides the matter. In a practical sense, though, obviousness depends on how the examiners interpret the code.
On to the point of this posting. While it is possible for an applicant to claim compositions never made or compositions that should exist by reasonable extrapolation, claims in the reverse sense are more problematic. But what do I mean?
Consider US 7,235,700, a process patent claiming the preparation of a cyclohexenone functionalized on the beta carbon with an enol ether group. [Disclaimer: again, this patent was “randomly” chosen. I have no specific axe to grind with the assignees or the inventors. I do, however, have an axe to grind with US patent law.]
This process is a good piece of journeyman organic synthesis featuring the preparation of an alpha/omega functionalized fragment with a Grignard functional group on one end and a silyl-protected oxygen on the other. From Example 2 of the ‘700 patent, to the Grignard reagent, made in the customary fashion in diethyl ether with dibromoethane as an entrainment additive, was added a THF solution of the cyclohexenone enol ether. The Grignard added to the enone in 1,2 fashion to afford a tertiary alcohol which upon acid hydrolysis, the resulting alcohol eliminates and the 3-alkoxy enol ether hydrolyzes to afford the product cyclohexenone on workup.
The patent teaches that the inventors had a poor process before this patented process (column 1, line 37). So, this must be an improvement, right? It seems to be. But, should it receive a patent?
From my copy of Kharasch and Reinmuth, I see that 1,2-additions of Grignard reagents to cyclohexenone were reported as early as 1941 (Whitmore, Pedlow JACS, 1941, 63, 758-760). So the knowledge of 1,2- vs 1,4-additions by RMgX nucleophilic additions to cyclohexenones resulting in primarily 1,2-addition is not new.
The use of nucleophiles with protected incompatible functional groups is not new. The hydrolysis of enol ethers is not new. Indeed, nowhere in the description do the inventors state that the disclosed transformations were “surprising” or “unexpected” in their outcome. As a phosita myself, I look at this patent and see good solid organic synthesis. I see the results of workers who have undergone training in the usual graduate level chemistry curriculum. Advanced organic synthesis with attention to donors and acceptors, functional group transformations, and protection/deprotection schemes. They took known transformations and assembled the pieces into the desired molecule.
My objection is this. Under the convention that Markush claims are allowed under current practices, many compositions of matter can be claimed by virtue of simple declaration despite the fact that homologous series or the usual genus groups of radicals (alkyl, alkenyl, alkynyl, aryl, heteroaryl, etc.) may be rather obvious additions to the list. A Phosita would reasonably state that if methyl is feasible, then so is ethyl, propyl, butyl, …, alkyl. Markush claims invoke a kind of obviousness that is allowed.
However, the same principle may not apply in reverse. That aspect of the body of scientific work teaching that certain generalizations are possible does not seem to be allowed in determinations of obviousness.
In the instant example, the generalization is that Grignards as a class might be expected to add in the fashion claimed in the ‘700 patent. Or that enol ethers as a class would be expected to undergo acid catalyzed hydrolysis to ketones. In the ‘700 patent, elements of the claim are novel only by virtue of being obscure members of a very large set of possibilities.
So, on the novelty and obviousness side of examination, the fact that a claim uses known transformations or schemes on heretofore unreported substrates bearing known features seems to be sufficient to cause an examiner to allow the claim. The allowance of Markush claims then allows broad generalization into large sets of claimed structures.
But generalization from a broad area of knowledge may not necessarily bar an unreported claim element when acted upon by known influences resulting in transformations that are consistent with the broad knowledge, as in the case of the ‘700 patent.
A patent lawyer reading this might object that the novelty of the substrate and the lack of specific precedence confers novelty and non-obviousness under current precedent. That lawyers opinion might be internally consistent with precedent and most would leave it at that.
But the overarching concern that I want to draw attention to is that the current practice in relation to novelty and obviousness may not serve the public interest. I’m seeing far too many patents being allowed for the application of known transformations to substrates that are merely obscure. What passes for inventorship is often just good craftsmanship. Reacting a Grignard reagent with a ketone followed by elimination is a general process that we might teach to students in a classroom.
Indeed, the current practice of teaching chemists is to expose the student to systematic generalizations of reaction-types so that they can go out and put generalizations into practice rather that have to memorize countless specifics.
When these chemists apply their training by reducing generalizations to practice on specific substrates, however, it seems they can claim to have made an invention under US patent law.
The upshot is that a good deal of technology resulting from ordinary problem solving skills is barred from the public domain for 20 years. Not that I believe that privately developed inventions should be in the public domain. But I will point out that it is quite easy for a company to get clobbered by an infringement suit for stumbling into claimed art by practicing what their chemists learned to do in graduate school. Reducing general reactions to practice.
I suspect that it is common practice for companies to believe that if something is patentable, then a patent is manditory. Unfortunately, the current system seems over-generous in granting 20 year monopolies for dubious inventions. When the threshold for obtaining a patent is too low, when practices are too easily removed from the commons, others trying to practice the art are unreasonably restrained.
Reform of matters as basic as the definition of obviousness and novelty cannot come from the USPTO, the courts, or from patent attorneys. Applicants and their attorneys will continue to game the system to the extent allowed by the courts. Fundamental change must come from legislation.
I keep running into people who claim that atmospheric CO2 levels lag atmospheric temperature rises rather than lead them. That is, higher CO2 levels are a result of global temperature increases rather than a cause. I’m not a researcher in this area, so my opinion is approximately meaningless. But on basic principles, it would seem that the partial pressure (or mole fraction, really) of CO2 might be expected to increase in the atmosphere over a warming ocean containing carbonate.
Aqueous CO2 equilibria is complicated by its reaction with water, but one should still expect that the decrease in solubility of CO2 in surface waters might have some bearing on the present atmospheric CO2 levels. For a given dT of an aqueous system with dissolved CO2, how does the mole fraction of CO2 in the gas phase change? The last time I worked a problem like this Ronald Reagan was president. Sigh.
Th’ Gaussling has been on the road the last few days visiting one of the states shaped like an oven mit up along the north coast. This is my first visit to this area during the summer. It is very beautiful country.
We had an inflight medical emergency enroute to a stop in the Windy City. The call came over the PA “Is there a doctor on the plane?”. Two vacationing MD’s, one in a fishing vest, rendered aid to a fellow who had a seizure. They had the poor sod on the floor with a saline i.v. and O2 for 90 minutes. The guy was lucky that he had more than an Untied (Airline name purposely altered) Stewtron to look after him. A business associate had the same experience the same day on the same route, but on a different flight. Curious. [Note to self: Bring meds on trip.]
Now that we are well into tornado season in North America, I thought I’d dredge this old post up out of the cobwebs in the dungeon. As Uncle Al pointed out in the comments, Middle Easterners did have dust devils so a vortex of wind was not unknown there. These, however, are no match for a full-blown F4 tornado.
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One has to wonder what the original inhabitants of North America thought of the tornado (how do you say “WTF” in Lakota?). I have visited a few museums in my travels but have never seen any artifacts or heard of any references to Native American perceptions of the tornado phenomenon. Without a doubt, Native Americans were visited by tornadoes. The experience must have certainly left an impression. It would be interesting to hear any stories that may be out there. An internet search just offers a Mulligan stew of hits with tired references to Pecos Bill or to the odd disaster in Kansas.
North America is climatically privileged in that there is the possibility that overland southerly flows of cold dry air from the north can readily contact flows of warm moist air from the Pacific, Gulf of Mexico, or the Atlantic. Vertical mixing of unstable humid air results in convection cells that are further driven by the latent heat of condensation. These humid flows are spun up by the coriolis effect and wind shear to afford monster anvil storm cells that can tower to 50,000 ft or higher.
Like many places, here in Colorado we often see lines of isolated storm cells in the early evenings of summer, red in color at low altitude changing to a billowy yellow-white at altitude near sunset. Very often you can see mammatocumulous features signifying violent mixing activity. It’s no place for an airplane.
It is interesting to speculate as to how our modern mythologies and iconographies might have been different if the tornado phenomenon had been common in the Mediterranean and the middle east. Would Charleton Heston have summoned a tornado to smite Yule Brynner’s Egyptians rather than parting the Red Sea and drowning the buggers? Perhaps the Pharaohs might have built great stone helices rather than oblisks. Aristotle might have written a treatise on the handedness of helical flows or whether the air flowed radially into or out of a tornado.
If the tornado had been a common phenomenon in the middle east during the iron age would the “Big Three” Abrahamic religions today feature tornadic themes in their texts and monuments? If so, perhaps the great cathedrals of Europe might today have relief sculptures or stained glass windows portraying the Israelites or Philistines being driven hither and thither by the swirling wrath of the Almighty’s cyclone.
Well, that’s enough of that.
Lamentations on Chemistry 