Coconut Oil Leads To Dementia?

[shepherdgirl]

@Travis - wouldn't platinum/copper persorb too though?
Why not do away with the screen altogether for something less...flaky? maybe cubes of catalyst would chip less?
What about filtration of the end product, is that a pipedream?

 

[Travis]

@Travis - wouldn't platinum/copper persorb too though?
Why not do away with the screen altogether for something less...flaky? maybe cubes of catalyst would chip less?
What about filtration of the end product, is that a pipedream?

I think you could have any shape catalyst, but an increase in surface are would reduce hydrogenation time; and since this occurs at a high temperature, a high surface area catalyst would also save energy.

I think you could certainly make hydrogenated coconut oil with zero particles. The reason why there's particles is probably just to cut costs, and the producers don't care much because the avoid becoming aware of information which could force them to acknowledge a problem. Robert Anton Wilson talks about the 'burden of omniscience,' what he takes to mean how information is withheld from powerful people out of fear. Nobody wants to be the bearer of bad news, and people who surround the CEOs tend to becomes 'yes men.'

Aluminum and nickel are cheap. I think you can be sure that every particle found in hydrogenated oil is balanced by energy and metal savings.

I really do think someone should start a business producing platinum‐catalyzed hydrogenated food oils to be sold to the health‐conscious. Not only would you have those customers, the yuppies would surely buy anything with the word 'platinum' on it (as long as it costs more.)

 

[shepherdgirl]

So...
CocoPlatinum™
and CocoZero™!

 

[yerrag]

Since the topic is on hydrogenation, would it be safe to say that all oils that undergo hydrogenation, be it partially or fully, is subject to the same contamination of aluminum and nickel? That this is not a problem with hydrogenated coconut oil only, but more so, of oils that are polyunsaturated, which requires a greater degree of hydrogenation in order to get fully hydrogenated?

 

[Travis]

Since the topic is on hydrogenation, would it be safe to say that all oils that undergo hydrogenation, be it partially or fully, is subject to the same contamination of aluminum and nickel? That this is not a problem with hydrogenated coconut oil only, but more so, of oils that are polyunsaturated, which requires a greater degree of hydrogenation in order to get fully hydrogenated?

I would guess the partially‐hydrogenated ones would have less since they are more fluid, with more particles drifting towards the bottom of the tank. It's hard to say. I think you could find data between oils, to look for a trend, but probably not enough to overcome the inter‐batch variation.

 

[yerrag]

I would guess the partially‐hydrogenated ones would have less since they are more fluid, with more particles drifting towards the bottom of the tank. It's hard to say. I think you could find data between oils, to look for a trend, but probably not enough to overcome the inter‐batch variation.

Fair enough, since the comparison would be between partially hydrogenated PUFAs and fully-hydrogenated coconut oil. But what if the comparison is between fully-hydrogenated PUFAs and fully-hydrogenated coconut oil?

Speaking of trans-fats, and sorry for being off-topic, how is it possible for many products these days made from PUFAs being labeled as trans-fat-free? Did they make them fully-hydrogenated?

If so, how could these oils/fats be fully-hydrogenated yet are liquid at room temperature?

 

[jb116]

Fair enough, since the comparison would be between partially hydrogenated PUFAs and fully-hydrogenated coconut oil. But what if the comparison is between fully-hydrogenated PUFAs and fully-hydrogenated coconut oil?

Speaking of trans-fats, and sorry for being off-topic, how is it possible for many products these days made from PUFAs being labeled as trans-fat-free? Did they make them fully-hydrogenated?

If so, how could these oils/fats be fully-hydrogenated yet are liquid at room temperature?

"Trans-fat free" is a marketing gimmick. Because "trans-fats" are another evil buzz word, technically something that doesn't contain it, can be touted as in fact being "trans-fat free."
And for the products that contained industrially made trans-fats, they simply stop putting them in the pufa foods.
Keep in mind, trans-fats are not the problem. It's the industrial process of creating them. Trans-fats from dairy for example are beneficial and have been shown to be so, directly opposite to industrial made trans-fats. The industry doesn't make this distinction and companies will surely jump on the buzz word bandwagons to sell.

Regarding the liquid at room temp, assuming the oil isn't fractionated, it's always otherwise about the ratio of saturated to unsat.

 

[yerrag]

"Trans-fat free" is a marketing gimmick. Because "trans-fats" are another evil buzz word, technically something that doesn't contain it, can be touted as in fact being "trans-fat free."
And for the products that contained industrially made trans-fats, they simply stop putting them in the pufa foods.
Keep in mind, trans-fats are not the problem. It's the industrial process of creating them. Trans-fats from dairy for example are beneficial and have been shown to be so, directly opposite to industrial made trans-fats. The industry doesn't make this distinction and companies will surely jump on the buzz word bandwagons to sell.

Regarding the liquid at room temp, assuming the oil isn't fractionated, it's always otherwise about the ratio of saturated to unsat.

So transfat-free could simply be PUFAs that aren't subjected to any degree of hydrogenation then?

Could it just be the PUFAs in the trans-fats that are harmful, and not the fat portion in the oil that has been hydrogenated?

What is the problem with the industrial process used to create trans-fats? Is it the use of nickel and aluminum catalysts? Or there's more to it?

 

[Travis]

Fair enough, since the comparison would be between partially hydrogenated PUFAs and fully-hydrogenated coconut oil. But what if the comparison is between fully-hydrogenated PUFAs and fully-hydrogenated coconut oil?

Speaking of trans-fats, and sorry for being off-topic, how is it possible for many products these days made from PUFAs being labeled as trans-fat-free? Did they make them fully-hydrogenated?

If so, how could these oils/fats be fully-hydrogenated yet are liquid at room temperature?

Interesting question. Perhaps chemists had figured out to selectively add both hydrogens to the same side of the double bond in all cases. I can see this happening.. .

Linstead, R. P. "The Stereochemistry of Catalytic Hydrogenation. I. The Stereochemistry of the Hydrogenation of Aromatic Rings." Journal of the American Chemical Society (1942)​

Now these are cyclic molecules with double=bonds:

'The catalytic hydrogenations were carried out over Adams platinum oxide in acetic acid unless otherwise stated.' ―Linstead

'There appears to be no other reasonable way of accounting for the regular occurrence of syn-hydrogenation over platinum.' ―Linstead

'There is a remarkable regularity in these results. All the hydrogenations studied have given largely cis- and syn-material. The only compound which gives a main per-hydrogenation product containing a trans-linkage is the trans-hexahydrodiphenic acid which already contains such a linkage.' ―Linstead​

The terms syn and anti are used when talking about cyclic carbon rings, and are completely analogous to the cis and trans of straight chain fatty acids and other alkenes.

'The abnormal mechanism is much more evident in hydrogenation over nickel, and may be presumed to account for the formation of predominantly trans-products in Preferred adsorption; Ring A clear of catalyst; syn-hydrogenations. In the somewhat milder hydrogenations over Raney nickel the orientations are irregular, and it appears certain that both mechanisms may function. Thus we see syn-cis over platinum at 25° and almost exclusively cis-syn-cis over nickel at 160°.' ―Linstead​

The metal does play a role. This must have something to do with the atomic spacing in the metal itself, or perhaps the speed in hydrogen transfer (perhaps dependent on reduction potential). Linstead does speculate a bit on the speed, or the possibility of the molecule moving before both hydrogens can be transferred—an event leading to the trans, or anti configuration.

'The regularity in these experiments invites a theoretical analysis. We propose three hypotheses to account for the results: (1) that when one or more aromatic rings are hydrogenated during a single period of adsorption, the hydrogen atoms add to one side of the molecule; (2) that the orientation of the adsorption of the aromatic molecule on the catalyst is affected by hindrance between the catalyst and the substrate ("catalyst hindrance") ; ( 3) that the derivatives of dipheriic acid which have been studied are hydrogenated in the coiled phase. These will now be considered in turn. (1) One-sided Addition. Willstatter in 1906 made the basic discovery that aromatic compounds could be hydrogenated at room temperatures over a platinum catalyst. It was some years before it was observed, mainly owing to the work of Skita and von Auwers, that, when two or more nuclear substituents were present, the products obtained by the use of platinum were isomeric but not identical with those obtained by Sabatier hydrogenations of the same compounds over nickel at high temperatures. As is well known, it was generally accepted that the products were geometrical isomers of the von Baeyer type, the compounds prepared over platinum being cis, and those by the Sabatier method being trans. Moreover, Skita, in particular, noted that in hydrogenations over platinum a cis orientation was favored in acid media, a trans orientation in neutral or basic media.' ―Linstead​

I think hydrogen‐transfer speed could play a role. You might think an acid media would have more hydrogen potential, more platinum‐adsorbed hydrogens, and would catalyze quicker for this reason—before any molecular shifting could lead to a trans configuration. You might also think that a basic media would have less hydrogens adsorbed.

'There is an increasing body of evidence that the adsorption of an organic molecule on a catalyst, and hence the ease of hydrogenation, is affected by stereochemical considerations. The recent work of Beeck, Smith and Wheelerz has shown the importance of the orientation of the metallic atoms in the lattice of the catalyst on its activity. It is possible that the catalytic hydrogenation of large aromatic molecules, which are planar and comparatively rigid, will be determined largely by the ability of the molecule to find an area in the catalyst which has sufficient size, suitable spacing of the metallic atoms, and sufficient flatness.' ―Linstead

'We suggest that the stages in the hydrogenation which determine that the product shall have a cis-configuration are : (1) the adsorption of the aromatic molecule upon a suitable part of the catalyst; and (3) the addition of the hydrogen to the molecule from the underside so that all the atoms appear on the same side of the asymmetric carbon atoms. This is illustrated diagrammatically below for the case of a phenanthrene nucleus. The arrows represent the approach of the hydrogen atoms from the catalyst.' ―Linstead​

​

'In the case of polynuclear compounds, there is little doubt that this is an oversimplification.' ―Linstead

'To the best of our knowledge, the proposal that there can be a steric hindrance between a metallic catalyst and its substrate is novel. There appears to be no other reasonable way of accounting for the regular occurrence of syn-hydrogenation over platinum. There is a philosophical connection with Bergmann’s explanationz of the selective action of proteolytic enzymes (peptidases) on polypeptides made from natural and unnatural amino acids, respectively.' ―Linstead​

He had carried out hydrogenation on rings with different substitutions leading to different results. He had determined that the substituents played a role in how the molecules were adsorbed onto the platinum. He had basically given a simple geometrical explanation for his observations.

'The stereochemistry of the hydrogenation of a number of derivatives of diphenic acid and of phenanthrene over a platinum catalyst is discussed. The nine compounds studied all hydrogenate cis and syn. The results are explained on the basis of three hypotheses. 1. When one or more aromatic rings are hydrogenated during a single period of adsorption, the hydrogen atoms add to one side of the molecule. 2. The orientation of the adsorption of the aromatic molecule on the catalyst is affected by hindrance between the catalyst and the substrate. 3. The open-chain derivatives of diphenic acid are hydrogenated in the coiled phase. Earlier work is discussed in the light of these views, and certain applications to related fields are indicated.' ―Linstead
​

Based on this, it appears it had been known a way to produce all cis‐fatty acids as far back as the 1942. I would think that the reduction potential could be modified to transfer both hydrogens to one side quickly before molecular wiggling can induce a trans‐fatty acid. Perhaps a little electricity applied to the catalyst screen, plate, or pipe, could change the speed of hydrogenation?

 

[managing]

"Trans-fat free" is a marketing gimmick. Because "trans-fats" are another evil buzz word, technically something that doesn't contain it, can be touted as in fact being "trans-fat free."
And for the products that contained industrially made trans-fats, they simply stop putting them in the pufa foods.
Keep in mind, trans-fats are not the problem. It's the industrial process of creating them. Trans-fats from dairy for example are beneficial and have been shown to be so, directly opposite to industrial made trans-fats. The industry doesn't make this distinction and companies will surely jump on the buzz word bandwagons to sell.Can

Regarding the liquid at room temp, assuming the oil isn't fractionated, it's always otherwise about the ratio of saturated to unsat.

Can you give an example of a dairy trans-fat?

 

[shepherdgirl]

how is it possible for many products these days made from PUFAs being labeled as trans-fat-free? Did they make them fully-hydrogenated?

In many cases no, they are simply allowed to list the trans fat content as zero if it contains less than 0.5 g of trans fat per serving. That is quite a bit of trans fat. Apparently this loophole is going to be changing this year.
http://www.berkeleywellness.com/healthy-eating/nutrition/article/labeling-trans-fats

would it be safe to say that all oils that undergo hydrogenation, be it partially or fully, is subject to the same contamination of aluminum and nickel?

I may be wrong, but it's my opinion that they use cheap catalysts to hydrogenate all kinds of edible oils, and as Travis mentioned, nickel and aluminum are very cheap, so they probably use them a lot. Even if it is not nickel or Al they are using, I think the product would still tend to be contaminated with tiny particles of catalyst that can cause serious problems in the bloodstream (due to persorption). It makes me wonder if trans fats have been taking the rap for nanoparticulate and pufa damage all along.

 

[Travis]

Can you give an example of a dairy trans-fat?

Vaccenic acid.

 

[managing]

Vaccenic acid.

interesting stuff. I wasn't aware of these. Thanks.

 

[Travis]

'Trans fatty acids compete with essential fatty acids and may exacerbate essential fatty acid deficiency.' ―Mayes

It makes me wonder if trans fats have been taking the rap for nanoparticulate and pufa damage all along.

This is certainly an interesting thought. The link between trans fatty acids and cancer appear to be just epidemiological associations with multiple confounders; trans fats could merely be a biomarker for a bad diet—and Raney particles?

Ip, Clement. "Review of the effects of trans fatty acids, oleic acid, n-3 polyunsaturated fatty acids, and conjugated linoleic acid on mammary carcinogenesis in animals." The American journal of clinical nutrition (1997)​

Since fatty acids are arranged on a triglyceride, a certain amount of care needs to be taken to ensure the control rats get the same lipids; it actually matters whether a fatty acid is in the sn‐1 or the sn‐2 position. The most popular trans fat is 18:1, so it's essentially the only one that had been studied. From reading this article, I'm getting the impression that these cancer test diets were custom‐made diets and perhaps free of Raney particles.

'...was a custom-prepared partially hydrogenated mixture of 50% soybean oil and 50% cottonseed oil. It contained 57.5% 18:1 (22.5% cis monoene and 35% trans monoene).' ―Clement Ip​

But you won't believe the results from the six cancer studies conducted on trans 18:1 before 1997:

'The dimethylbenz[a]anthracene (DMBA)-induced rat mammary tumor model was used in this study. Tumor incidences for the 20%-trans fat, 20%-cis fat, and 20%-corn oil groups (n = 25 per group) were 32%, 40%, and 80%, respectively. The corresponding total tumor numbers were 18, 27, and 72, respectively. Statistically, there was no difference in the tumor data between the trans and cis fat groups, but the corn oil group clearly produced more tumor-bearing animals and more tumors per rat than did the two other groups. The corn oil results are consistent with the stimulatory effect of l8:2 n−6 as discussed by Rose.' ―Clement Ip

'The same blended trans and cis fats were also used in a study by Erikson et al (9) to investigate the effects of these fats (at either 5% or 20% by weight in the diet) on the growth and metastasis of implanted mammary tumor cells. [...] However, in mice receiving the intravenous implants, the liver and spleen from those fed the cis fat diets contained significantly more viable radiolabeled tumor cells than did those from mice fed the trans fat diets. Thus, trans monoene fatty acid appeared to behave similarly as cis monoene fatty acid regarding influencing the growth of the primary mammary tumor at the local transplantation site but might be less effective than cis fatty acid in promoting the blood borne homing and survival of tumor cells at the distant organ sites.' ―Clement Ip

'It was found that neither tumor incidence nor tumor multiplicity at the two sites was affected by changing the ratio of dietary trans-18:1 to cis-18:1. For the low-, intermediate- and high-trans-fat diets, the incidences of colon tumors were 63%, 67%, and 57%, respectively, and the incidences of small intestinal tumors were 40%, 43%, and 37%, respectively. This study therefore confirmed that varying the intake of trans and cis monoenes had little effect on intestinal cancer risk.' ―Clement Ip​

He goes on to summarize two studies which had shown no difference, and then writes:

'Finally, Kritchevsky et al (13) studied the effect of hydrogenated soybean oil (containing 71 % trans unsaturated fatty acids) in the DMBA-induced mammary tumor model. Their data showed that compared with the unhydrogenated soybean oil, the hydrogenated soybean oil actually produced a slight reduction in tumor incidence and tumor multiplicity.' ―Clement Ip
​

So trans 18:1 appears slightly protective, perhaps by displacing linoleic and arachidonic acids from the cell membrane. Trans fatty acids are also straight‐chained, and might then confer a bit more membrane rigidity like stearic acid and cholesterol does.

He goes on to talk about oleic acid, conjugated linoleic acid, and ω−3 oils. He also talks plainly about the carcinogenic potential of linoleic acid:

'Consequently, the reduction of tumors in the animals fed olive oil might be due to an insufficient supply of 18:2 n−6 [linoleic acid]. Following this argument, it is reasonable to postulate that a certain amount of l8:2 n−6, by virtue of its role as a precursor of prostaglandins and other eicosanoids, is necessary for optimal promotion of mammary carcinogenesis.' ―Clement Ip​

'Depending on the source, commercially available olive oil can vary greatly in its content of l8:2 n−6. Such a discrepancy could explain the dichotomous results regarding the effect of olive oil on carcinogenesis. If a brand of olive oil that is relatively rich in l8:2 n−6 is used, no difference in tumorigenesis will likely be detected when this oil is compared with another oil that is also high in l8:2 n−6. However, if a brand of olive oil that is poor in l8:2 n−6 is used, a reduction in tumorigenesis will be expected to occur.' ―Clement Ip
​

Like David Rose, Clement Ip expects linoleic acid to cause tumors—and he's not afraid to say so.

 

[jb116]

So transfat-free could simply be PUFAs that aren't subjected to any degree of hydrogenation then?

Could it just be the PUFAs in the trans-fats that are harmful, and not the fat portion in the oil that has been hydrogenated?

What is the problem with the industrial process used to create trans-fats? Is it the use of nickel and aluminum catalysts? Or there's more to it?

"So transfat-free could simply be PUFAs that aren't subjected to any degree of hydrogenation then?"
YES. Or, simply a PUFA rich food boasting some "benefit" on the label.

Most evidence suggests that “natural” TFAs are not harmful and are actually beneficial where as industrially made TFAs are harmful. The question remains, is it the toxic and metal content of industrial TFAs or PUFA toxic remnants within the industrial TFA from the process? Either way, most conclusions, directly or indirectly, point to industrial TFA as harmful. I believe Dr. Peat touched on that aspect of industrial TFA, and mentioned metals.

WHO Report on Trans Fats: Effects of Industrial versus Ruminant Trans Fat | Dairy Nutrition


Highlights

• Industrial TFA consumption is believed to increase cardiovascular risk in multiple ways.
  
  
• Ruminant TFA consumption in the amounts normally consumed does not appear to increase CHD risk.
  
  
• Consumption of ruminant-derived vaccenic acid may impart health benefits beyond those associated with conjugated linoleic acid.

Ruminant and industrially produced trans fatty acids: health aspects

Conclusion
The intake of ruminant trans fatty acids is maximally 4–5 g/day, whereas the intake of industrially produced trans fat in some population groups far exceeds 5 g/day. Since there is evidence for harmful effects of industrially produced trans fatty acids at this level, but not for ruminant trans fatty acids, and since it is feasible to eliminate industrially produced trans fatty acids from the food supply without side effects in the population, this elimination can be considered a ‘low hanging fruit’ in the quest for a more healthy diet for the entire population in any given country. How to do it is a political issue. <--- lol astonishing.


Intake of saturated and trans unsaturated fatty acids and risk of all cause mortality, cardiovascular disease, and type 2 diabetes: systematic review and meta-analysis of observational studies
meta-analysis

Conclusions
Saturated fats are not associated with all cause mortality, CVD, CHD, ischemic stroke, or type 2 diabetes, but the evidence is heterogeneous with methodological limitations. Trans fats are associated with all cause mortality, total CHD, and CHD mortality, probably because of higher levels of intake of industrial trans fats than ruminant trans fats. Dietary guidelines must carefully consider the health effects of recommendations for alternative macronutrients to replace trans fats and saturated fats.

Consumption of <i>trans</i> fats and estimated effects on coronary heart disease in Iran

Conclusions
Intake of [industrial] TFAs is high in Iranian homes and contributes to a sizeable proportion of CHD events. Replacement of partially hydrogenated oils with unhydrogenated oils would likely produce substantial reductions in CHD incidence.

My Thoughts
This one is tricky, as it indirectly reveals the truth about industrial Trans Fats and confirms their detriment but with a conclusion of "if the TF was replaced with unhydrogenated oils it would reduce CHD." LOL I'm not particularly fond of the fact that this study mentions industrial TF assessment from the get-go but then continues to leave “industrial” out to focus more on promoting the use of unsaturated vegetable oils with omega 3. It's such a tricky play on what's apparent and what is actual. It progresses along to prove industrial TF is related to CHD and then establishes the assumption that yet another evil type fat (leaving pufa out) is killing us. If you aren't careful, you get sucked into acquiescence. But the point with trans fats is centered around how they're made. So the conclusion of industrially made trans fats being bad for us does not equate to "unhydrogenated oils must be good for us" like they imply, since that would mostly assume most vegetable oils that are not hydrogenated are good, invoking PUFAs once again. In addition, it should be noted that these were discovered to be mostly partially hydrogenated oils, which means these populations were already ingesting plenty of PUFA. In fact, plenty of PUFA and industrial TF. Not so good.


An exploration of socio-economic and food characteristics of high trans fatty acid consumers in the Dutch and UK national surveys after voluntary product reformulation
Again not the best studies but still confirming.

Trans fatty acids (TFAs) are linked to all-cause mortality and various chronic diseases, most notably coronary heart disease (CHD) [1]. CHD causes around 10,200 deaths in the Netherlands [2] and approximately 73,000 deaths in the UK annually, making it the largest cause of mortality [3]. In addition, for every 2% total energy gained from TFAs there is a corresponding 23% increase in CHD incidence [4]. Industrial trans fatty acids (iTFA) are artificially produced in processed foods by hydrogenating vegetable or fish oils [5] and are associated with CHD mortality and total CHD [1]. Bakery products, spreads, packaged snack foods and deep-fried fast foods have been identified as major sources of iTFA [6]. The UK Low Income Diet and Nutrition Survey found unequal consumption of TFA by socio-economic status, with the most deprived groups having higher intakes of processed foods and takeaways [7]. Pearson-Stuttard et al. [8] suggest that reducing iTFA intake could substantially reduce health inequalities in CHD mortality. They estimated that a 1% reduction in TFA of daily energy intake would result in five times fewer deaths and six times more life years in the most deprived quintile than the most affluent.

My thoughts: so again, we have a somewhat ambiguous account as to what truly causes all-cause mortality. Words like “linked to” scream correlation to me, not cause. This definitely sets up a scenario where we may be looking at PUFAs getting away with murder but also general poor dietary habits. Take note of the foods mentioned. But again, even with PUFAs removed from the equation, you are still looking at industrial TFAs vs. ruminant TFAs. It still reveals something to us. Of course, I can't see a study like this representing the U.S. Any longer because you'll be damned if you can find TFAs in food here. At least I can't, unless they are naturally occurring. I mention this because I think it's comical. It's just as comical as the push for PUFA because “its healthier for us” even though we've been over exposed to them for decades now. It boggles the mind.

Can you give an example of a dairy trans-fat?

In addition to what Travis mentioned, there's also trans-rumenic and conjugated linoleic acid.

 

[yerrag]

Interesting question. Perhaps chemists had figured out to selectively add both hydrogens to the same side of the double bond in all cases. I can see this happening.. .

Linstead, R. P. "The Stereochemistry of Catalytic Hydrogenation. I. The Stereochemistry of the Hydrogenation of Aromatic Rings." Journal of the American Chemical Society (1942)​

Now these are cyclic molecules with double=bonds:

'The catalytic hydrogenations were carried out over Adams platinum oxide in acetic acid unless otherwise stated.' ―Linstead

'There appears to be no other reasonable way of accounting for the regular occurrence of syn-hydrogenation over platinum.' ―Linstead

'There is a remarkable regularity in these results. All the hydrogenations studied have given largely cis- and syn-material. The only compound which gives a main per-hydrogenation product containing a trans-linkage is the trans-hexahydrodiphenic acid which already contains such a linkage.' ―Linstead​

The terms syn and anti are used when talking about cyclic carbon rings, and are completely analogous to the cis and trans of straight chain fatty acids and other alkenes.

'The abnormal mechanism is much more evident in hydrogenation over nickel, and may be presumed to account for the formation of predominantly trans-products in Preferred adsorption; Ring A clear of catalyst; syn-hydrogenations. In the somewhat milder hydrogenations over Raney nickel the orientations are irregular, and it appears certain that both mechanisms may function. Thus we see syn-cis over platinum at 25° and almost exclusively cis-syn-cis over nickel at 160°.' ―Linstead​

The metal does play a role. This must have something to do with the atomic spacing in the metal itself, or perhaps the speed in hydrogen transfer (perhaps dependent on reduction potential). Linstead does speculate a bit on the speed, or the possibility of the molecule moving before both hydrogens can be transferred—an event leading to the trans, or anti configuration.

'The regularity in these experiments invites a theoretical analysis. We propose three hypotheses to account for the results: (1) that when one or more aromatic rings are hydrogenated during a single period of adsorption, the hydrogen atoms add to one side of the molecule; (2) that the orientation of the adsorption of the aromatic molecule on the catalyst is affected by hindrance between the catalyst and the substrate ("catalyst hindrance") ; ( 3) that the derivatives of dipheriic acid which have been studied are hydrogenated in the coiled phase. These will now be considered in turn. (1) One-sided Addition. Willstatter in 1906 made the basic discovery that aromatic compounds could be hydrogenated at room temperatures over a platinum catalyst. It was some years before it was observed, mainly owing to the work of Skita and von Auwers, that, when two or more nuclear substituents were present, the products obtained by the use of platinum were isomeric but not identical with those obtained by Sabatier hydrogenations of the same compounds over nickel at high temperatures. As is well known, it was generally accepted that the products were geometrical isomers of the von Baeyer type, the compounds prepared over platinum being cis, and those by the Sabatier method being trans. Moreover, Skita, in particular, noted that in hydrogenations over platinum a cis orientation was favored in acid media, a trans orientation in neutral or basic media.' ―Linstead​

I think hydrogen‐transfer speed could play a role. You might think an acid media would have more hydrogen potential, more platinum‐adsorbed hydrogens, and would catalyze quicker for this reason—before any molecular shifting could lead to a trans configuration. You might also think that a basic media would have less hydrogens adsorbed.

'There is an increasing body of evidence that the adsorption of an organic molecule on a catalyst, and hence the ease of hydrogenation, is affected by stereochemical considerations. The recent work of Beeck, Smith and Wheelerz has shown the importance of the orientation of the metallic atoms in the lattice of the catalyst on its activity. It is possible that the catalytic hydrogenation of large aromatic molecules, which are planar and comparatively rigid, will be determined largely by the ability of the molecule to find an area in the catalyst which has sufficient size, suitable spacing of the metallic atoms, and sufficient flatness.' ―Linstead

'We suggest that the stages in the hydrogenation which determine that the product shall have a cis-configuration are : (1) the adsorption of the aromatic molecule upon a suitable part of the catalyst; and (3) the addition of the hydrogen to the molecule from the underside so that all the atoms appear on the same side of the asymmetric carbon atoms. This is illustrated diagrammatically below for the case of a phenanthrene nucleus. The arrows represent the approach of the hydrogen atoms from the catalyst.' ―Linstead​

View attachment 7894​

'In the case of polynuclear compounds, there is little doubt that this is an oversimplification.' ―Linstead

'To the best of our knowledge, the proposal that there can be a steric hindrance between a metallic catalyst and its substrate is novel. There appears to be no other reasonable way of accounting for the regular occurrence of syn-hydrogenation over platinum. There is a philosophical connection with Bergmann’s explanationz of the selective action of proteolytic enzymes (peptidases) on polypeptides made from natural and unnatural amino acids, respectively.' ―Linstead​

He had carried out hydrogenation on rings with different substitutions leading to different results. He had determined that the substituents played a role in how the molecules were adsorbed onto the platinum. He had basically given a simple geometrical explanation for his observations.

'The stereochemistry of the hydrogenation of a number of derivatives of diphenic acid and of phenanthrene over a platinum catalyst is discussed. The nine compounds studied all hydrogenate cis and syn. The results are explained on the basis of three hypotheses. 1. When one or more aromatic rings are hydrogenated during a single period of adsorption, the hydrogen atoms add to one side of the molecule. 2. The orientation of the adsorption of the aromatic molecule on the catalyst is affected by hindrance between the catalyst and the substrate. 3. The open-chain derivatives of diphenic acid are hydrogenated in the coiled phase. Earlier work is discussed in the light of these views, and certain applications to related fields are indicated.' ―Linstead
​

Based on this, it appears it had been known a way to produce all cis‐fatty acids as far back as the 1942. I would think that the reduction potential could be modified to transfer both hydrogens to one side quickly before molecular wiggling can induce a trans‐fatty acid. Perhaps a little electricity applied to the catalyst screen, plate, or pipe, could change the speed of hydrogenation?

I'm speechless.

I may be wrong, but it's my opinion that they use cheap catalysts to hydrogenate all kinds of edible oils, and as Travis mentioned, nickel and aluminum are very cheap, so they probably use them a lot. Even if it is not nickel or Al they are using, I think the product would still tend to be contaminated with tiny particles of catalyst that can cause serious problems in the bloodstream (due to persorption). It makes me wonder if trans fats have been taking the rap for nanoparticulate and pufa damage all along.

I'm also swayed that way as well.

"So transfat-free could simply be PUFAs that aren't subjected to any degree of hydrogenation then?"
YES. Or, simply a PUFA rich food boasting some "benefit" on the label.

Most evidence suggests that “natural” TFAs are not harmful and are actually beneficial where as industrially made TFAs are harmful. The question remains, is it the toxic and metal content of industrial TFAs or PUFA toxic remnants within the industrial TFA from the process? Either way, most conclusions, directly or indirectly, point to industrial TFA as harmful. I believe Dr. Peat touched on that aspect of industrial TFA, and mentioned metals.

WHO Report on Trans Fats: Effects of Industrial versus Ruminant Trans Fat | Dairy Nutrition


Highlights

• Industrial TFA consumption is believed to increase cardiovascular risk in multiple ways.
  
  
• Ruminant TFA consumption in the amounts normally consumed does not appear to increase CHD risk.
  
  
• Consumption of ruminant-derived vaccenic acid may impart health benefits beyond those associated with conjugated linoleic acid.

Ruminant and industrially produced trans fatty acids: health aspects

Conclusion
The intake of ruminant trans fatty acids is maximally 4–5 g/day, whereas the intake of industrially produced trans fat in some population groups far exceeds 5 g/day. Since there is evidence for harmful effects of industrially produced trans fatty acids at this level, but not for ruminant trans fatty acids, and since it is feasible to eliminate industrially produced trans fatty acids from the food supply without side effects in the population, this elimination can be considered a ‘low hanging fruit’ in the quest for a more healthy diet for the entire population in any given country. How to do it is a political issue. <--- lol astonishing.


Intake of saturated and trans unsaturated fatty acids and risk of all cause mortality, cardiovascular disease, and type 2 diabetes: systematic review and meta-analysis of observational studies
meta-analysis

Conclusions
Saturated fats are not associated with all cause mortality, CVD, CHD, ischemic stroke, or type 2 diabetes, but the evidence is heterogeneous with methodological limitations. Trans fats are associated with all cause mortality, total CHD, and CHD mortality, probably because of higher levels of intake of industrial trans fats than ruminant trans fats. Dietary guidelines must carefully consider the health effects of recommendations for alternative macronutrients to replace trans fats and saturated fats.

Consumption of <i>trans</i> fats and estimated effects on coronary heart disease in Iran

Conclusions
Intake of [industrial] TFAs is high in Iranian homes and contributes to a sizeable proportion of CHD events. Replacement of partially hydrogenated oils with unhydrogenated oils would likely produce substantial reductions in CHD incidence.

My Thoughts
This one is tricky, as it indirectly reveals the truth about industrial Trans Fats and confirms their detriment but with a conclusion of "if the TF was replaced with unhydrogenated oils it would reduce CHD." LOL I'm not particularly fond of the fact that this study mentions industrial TF assessment from the get-go but then continues to leave “industrial” out to focus more on promoting the use of unsaturated vegetable oils with omega 3. It's such a tricky play on what's apparent and what is actual. It progresses along to prove industrial TF is related to CHD and then establishes the assumption that yet another evil type fat (leaving pufa out) is killing us. If you aren't careful, you get sucked into acquiescence. But the point with trans fats is centered around how they're made. So the conclusion of industrially made trans fats being bad for us does not equate to "unhydrogenated oils must be good for us" like they imply, since that would mostly assume most vegetable oils that are not hydrogenated are good, invoking PUFAs once again. In addition, it should be noted that these were discovered to be mostly partially hydrogenated oils, which means these populations were already ingesting plenty of PUFA. In fact, plenty of PUFA and industrial TF. Not so good.


An exploration of socio-economic and food characteristics of high trans fatty acid consumers in the Dutch and UK national surveys after voluntary product reformulation
Again not the best studies but still confirming.

Trans fatty acids (TFAs) are linked to all-cause mortality and various chronic diseases, most notably coronary heart disease (CHD) [1]. CHD causes around 10,200 deaths in the Netherlands [2] and approximately 73,000 deaths in the UK annually, making it the largest cause of mortality [3]. In addition, for every 2% total energy gained from TFAs there is a corresponding 23% increase in CHD incidence [4]. Industrial trans fatty acids (iTFA) are artificially produced in processed foods by hydrogenating vegetable or fish oils [5] and are associated with CHD mortality and total CHD [1]. Bakery products, spreads, packaged snack foods and deep-fried fast foods have been identified as major sources of iTFA [6]. The UK Low Income Diet and Nutrition Survey found unequal consumption of TFA by socio-economic status, with the most deprived groups having higher intakes of processed foods and takeaways [7]. Pearson-Stuttard et al. [8] suggest that reducing iTFA intake could substantially reduce health inequalities in CHD mortality. They estimated that a 1% reduction in TFA of daily energy intake would result in five times fewer deaths and six times more life years in the most deprived quintile than the most affluent.

My thoughts: so again, we have a somewhat ambiguous account as to what truly causes all-cause mortality. Words like “linked to” scream correlation to me, not cause. This definitely sets up a scenario where we may be looking at PUFAs getting away with murder but also general poor dietary habits. Take note of the foods mentioned. But again, even with PUFAs removed from the equation, you are still looking at industrial TFAs vs. ruminant TFAs. It still reveals something to us. Of course, I can't see a study like this representing the U.S. Any longer because you'll be damned if you can find TFAs in food here. At least I can't, unless they are naturally occurring. I mention this because I think it's comical. It's just as comical as the push for PUFA because “its healthier for us” even though we've been over exposed to them for decades now. It boggles the mind.


In addition to what Travis mentioned, there's also trans-rumenic and conjugated linoleic acid.

I agree. In this con game of elimination, saturated and trans-fats are struck out, the only game left is PUFA.

It amuses me no end that people recommend ketogenic diets. They came to be in need of ketogenic diets because they had been suffering the effects of PUFA and can't metabolize sugar. After bedeviling sugar, they come full circle and embrace fats once again as their savior. Two wrongs don't make it right.

 

[Badger]

>It amuses me no end that people recommend ketogenic diets. They came to be in need of ketogenic diets because they had been suffering the effects of PUFA and can't metabolize sugar. After bedeviling sugar, they come full circle and embrace fats once again as their savior. Two wrongs don't make it right.
Well said!

I'm speechless.

I'm also swayed that way as well.



I agree. In this con game of elimination, saturated and trans-fats are struck out, the only game left is PUFA.

It amuses me no end that people recommend ketogenic diets. They came to be in need of ketogenic diets because they had been suffering the effects of PUFA and can't metabolize sugar. After bedeviling sugar, they come full circle and embrace fats once again as their savior. Two wrongs don't make it right.

 

[Wagner83]

me:
Hi Ray,
I don't know if other people warned you about it but there's a concern of aluminium contamination with hydrogenated CO:

Coconut Oil Leads To Dementia?


And more information here:

Coconut Oil Leads To Dementia?

[I posted the two posts in the mail to make sure he would see them]

Ray:
Neurology. 1985 Feb;35(2):193-8.
Disappearance of high-incidence amyotrophic lateral sclerosis and parkinsonism-dementia on Guam.
Garruto RM, Yanagihara R, Gajdusek DC.
The high incidence rates of amyotrophic lateral sclerosis (ALS) and parkinsonism-dementia (PD) occurring among the Chamorros of Guam have declined to rates only slightly higher than those observed in the continental United States. This decline has occurred principally among males, especially those born after 1920 and living in areas where calcium and magnesium levels are low in soil and water. The male-to-female ratio among affected patients now approaches unity, compared with ratios of 2 to 1 for ALS and 3 to 1 for PD three decades ago. These changes are consistent with the hypothesis that the previously high incidence resulted from defects in mineral metabolism and secondary hyperparathyroidism, provoked by nutritional deficiencies of calcium and magnesium, with resultant deposition of calcium and aluminum in neurons.

J Occup Environ Med. 2014 May;56(5 Suppl):S73-9.
Is the Aluminum Hypothesis dead?
Lidsky TI.
The Aluminum Hypothesis, the idea that aluminum exposure is involved in the etiology of Alzheimer disease, dates back to a 1965 demonstration that aluminum causes neurofibrillary tangles in the brains of rabbits. Initially the focus of intensive research, the AluminumHypothesis has gradually been abandoned by most researchers. Yet, despite this current indifference, the Aluminum Hypothesis continues to attract the attention of a small group of scientists and aluminum continues to be viewed with concern by some of the public. This review article discusses reasons that mainstream science has largely abandoned the Aluminum Hypothesis and explores a possible reason for some in the general public continuing to view aluminum with mistrust.
Free PMC Article

 

[SB4]

I don't understand much about the hydrogenation proccess but here goes anyway:
Natural fats are deuterium (hydrogen isotope) depleted (<140ppm) as compared to carbohydrates and regular water (155ppm). When you add in your own hydrogens, you might well be adding them in with a deuterium concentration of 155ppm, bringing the overall deuterium of the fat up.
This now higher deuterium fat goes into the TCA and over to complex 2 where the heavier and slower to react deuterium briefly stops the electron flow through the ECT and jams up the ATPase.
This leads to lower energy production and thus disease.

 

[haidut]

I don't understand much about the hydrogenation proccess but here goes anyway:
Natural fats are deuterium (hydrogen isotope) depleted (<140ppm) as compared to carbohydrates and regular water (155ppm). When you add in your own hydrogens, you might well be adding them in with a deuterium concentration of 155ppm, bringing the overall deuterium of the fat up.
This now higher deuterium fat goes into the TCA and over to complex 2 where the heavier and slower to react deuterium briefly stops the electron flow through the ECT and jams up the ATPase.
This leads to lower energy production and thus disease.

So...are you saying that basically no matter what we eat it will jam up TCA and ETC? Or is it just synthetic fats that do that?